WO1993019128A2 - Polymers and polymer blends modified with poly(phenylene ether) - Google Patents
Polymers and polymer blends modified with poly(phenylene ether) Download PDFInfo
- Publication number
- WO1993019128A2 WO1993019128A2 PCT/US1993/002176 US9302176W WO9319128A2 WO 1993019128 A2 WO1993019128 A2 WO 1993019128A2 US 9302176 W US9302176 W US 9302176W WO 9319128 A2 WO9319128 A2 WO 9319128A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- poly
- composition
- alkyl
- copolymer
- compound
- Prior art date
Links
- -1 poly(phenylene ether) Polymers 0.000 title claims abstract description 454
- 229920000642 polymer Polymers 0.000 title claims description 78
- 229920002959 polymer blend Polymers 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 324
- 229920001577 copolymer Polymers 0.000 claims abstract description 190
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 147
- 239000004417 polycarbonate Substances 0.000 claims abstract description 71
- 229920000515 polycarbonate Polymers 0.000 claims abstract description 67
- 229920000728 polyester Polymers 0.000 claims abstract description 61
- 239000004793 Polystyrene Substances 0.000 claims abstract description 44
- 229920002223 polystyrene Polymers 0.000 claims abstract description 43
- 239000004952 Polyamide Substances 0.000 claims abstract description 38
- 229920002647 polyamide Polymers 0.000 claims abstract description 38
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims abstract description 21
- 239000004926 polymethyl methacrylate Substances 0.000 claims abstract description 21
- 229920001603 poly (alkyl acrylates) Polymers 0.000 claims abstract description 20
- 239000004609 Impact Modifier Substances 0.000 claims abstract description 19
- 239000004814 polyurethane Substances 0.000 claims abstract description 18
- 229920002635 polyurethane Polymers 0.000 claims abstract description 18
- 238000009757 thermoplastic moulding Methods 0.000 claims abstract description 14
- 239000000654 additive Substances 0.000 claims abstract description 13
- 239000000049 pigment Substances 0.000 claims abstract description 11
- 229920000098 polyolefin Polymers 0.000 claims abstract description 11
- 229920000915 polyvinyl chloride Polymers 0.000 claims abstract description 11
- 239000004800 polyvinyl chloride Substances 0.000 claims abstract description 11
- 229930182556 Polyacetal Natural products 0.000 claims abstract description 10
- 229920006324 polyoxymethylene Polymers 0.000 claims abstract description 10
- 239000000975 dye Substances 0.000 claims abstract description 8
- 239000000178 monomer Substances 0.000 claims description 98
- 229920001971 elastomer Polymers 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 53
- 238000000465 moulding Methods 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 150000001993 dienes Chemical class 0.000 claims description 42
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 31
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 28
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 claims description 26
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 26
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 25
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 23
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 229920006285 olefinic elastomer Polymers 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 229920002725 thermoplastic elastomer Polymers 0.000 claims description 16
- 239000011258 core-shell material Substances 0.000 claims description 15
- 239000000806 elastomer Substances 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 150000002118 epoxides Chemical group 0.000 claims description 14
- 238000002844 melting Methods 0.000 claims description 14
- 230000008018 melting Effects 0.000 claims description 14
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 13
- 150000001336 alkenes Chemical class 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 229910052751 metal Chemical class 0.000 claims description 8
- 239000002184 metal Chemical class 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 229910000410 antimony oxide Inorganic materials 0.000 claims description 7
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 7
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical class [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 229940058344 antitrematodals organophosphorous compound Drugs 0.000 claims description 5
- 150000008282 halocarbons Chemical class 0.000 claims description 5
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 5
- IYMZEPRSPLASMS-UHFFFAOYSA-N 3-phenylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C=2C=CC=CC=2)=C1 IYMZEPRSPLASMS-UHFFFAOYSA-N 0.000 claims description 4
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 claims description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 claims description 3
- 150000005840 aryl radicals Chemical group 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000000306 component Substances 0.000 abstract description 56
- 239000011159 matrix material Substances 0.000 abstract description 16
- 239000011347 resin Substances 0.000 abstract description 11
- 229920005989 resin Polymers 0.000 abstract description 11
- 229920000058 polyacrylate Polymers 0.000 abstract description 8
- 239000012141 concentrate Substances 0.000 abstract description 6
- 239000012778 molding material Substances 0.000 abstract 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 106
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 46
- 239000005060 rubber Substances 0.000 description 38
- 150000001875 compounds Chemical class 0.000 description 35
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 34
- 239000003054 catalyst Substances 0.000 description 29
- 239000012071 phase Substances 0.000 description 29
- 239000000126 substance Substances 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 28
- 125000003118 aryl group Chemical group 0.000 description 27
- 238000006116 polymerization reaction Methods 0.000 description 23
- 238000002156 mixing Methods 0.000 description 22
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 20
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 19
- 239000002253 acid Substances 0.000 description 19
- 229920001169 thermoplastic Polymers 0.000 description 19
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 18
- 229920001400 block copolymer Polymers 0.000 description 18
- 230000008569 process Effects 0.000 description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
- 239000004721 Polyphenylene oxide Substances 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 17
- 239000004416 thermosoftening plastic Substances 0.000 description 17
- 150000002009 diols Chemical class 0.000 description 16
- 238000009472 formulation Methods 0.000 description 15
- 239000003999 initiator Substances 0.000 description 15
- 229920005862 polyol Polymers 0.000 description 15
- 229920000638 styrene acrylonitrile Polymers 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000002245 particle Substances 0.000 description 14
- 150000003077 polyols Chemical class 0.000 description 14
- 239000005977 Ethylene Substances 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 229920000126 latex Polymers 0.000 description 12
- 229920000139 polyethylene terephthalate Polymers 0.000 description 12
- 239000005020 polyethylene terephthalate Substances 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 229910045601 alloy Inorganic materials 0.000 description 11
- 239000000956 alloy Substances 0.000 description 11
- 229920001903 high density polyethylene Polymers 0.000 description 11
- 239000004700 high-density polyethylene Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 239000002585 base Substances 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- 239000002243 precursor Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 229910019142 PO4 Inorganic materials 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 229920000578 graft copolymer Polymers 0.000 description 9
- 239000004816 latex Substances 0.000 description 9
- 235000021317 phosphate Nutrition 0.000 description 9
- 229920001228 polyisocyanate Polymers 0.000 description 9
- 239000005056 polyisocyanate Substances 0.000 description 9
- 239000002002 slurry Substances 0.000 description 9
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 8
- 239000003085 diluting agent Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- 238000007720 emulsion polymerization reaction Methods 0.000 description 8
- 150000002334 glycols Chemical class 0.000 description 8
- 238000010557 suspension polymerization reaction Methods 0.000 description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 7
- 125000002947 alkylene group Chemical group 0.000 description 7
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 7
- 229920001198 elastomeric copolymer Polymers 0.000 description 7
- 229920001684 low density polyethylene Polymers 0.000 description 7
- 239000004702 low-density polyethylene Substances 0.000 description 7
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 238000012662 bulk polymerization Methods 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 6
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 229920001519 homopolymer Polymers 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- 150000003440 styrenes Chemical class 0.000 description 6
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 5
- 239000005062 Polybutadiene Substances 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 5
- 239000006229 carbon black Substances 0.000 description 5
- 239000012986 chain transfer agent Substances 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 150000002431 hydrogen Chemical group 0.000 description 5
- 238000001746 injection moulding Methods 0.000 description 5
- 229920000092 linear low density polyethylene Polymers 0.000 description 5
- 239000004707 linear low-density polyethylene Substances 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 5
- 229920002857 polybutadiene Polymers 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical class CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 239000012670 alkaline solution Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 150000004072 triols Chemical class 0.000 description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 3
- WAEOXIOXMKNFLQ-UHFFFAOYSA-N 1-methyl-4-prop-2-enylbenzene Chemical group CC1=CC=C(CC=C)C=C1 WAEOXIOXMKNFLQ-UHFFFAOYSA-N 0.000 description 3
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 3
- ISRGONDNXBCDBM-UHFFFAOYSA-N 2-chlorostyrene Chemical compound ClC1=CC=CC=C1C=C ISRGONDNXBCDBM-UHFFFAOYSA-N 0.000 description 3
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- 229920001634 Copolyester Polymers 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 3
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- NSBGJRFJIJFMGW-UHFFFAOYSA-N trisodium;stiborate Chemical compound [Na+].[Na+].[Na+].[O-][Sb]([O-])([O-])=O NSBGJRFJIJFMGW-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L69/00—Compositions of polycarbonates; Compositions of derivatives of polycarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes
- C08L53/025—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes modified
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08L71/12—Polyphenylene oxides
- C08L71/123—Polyphenylene oxides not modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2555/00—Characteristics of bituminous mixtures
- C08L2555/40—Mixtures based upon bitumen or asphalt containing functional additives
Definitions
- this invention involves a method of molding an article comprising (I) forming a composition by melting in a molding machine components (a/a) and (b/a) which have not previously been melted together, said components (a/a) and (b/a) comprising
- compositions of this invention are useful, for example, in the production of films, fibers, extruded sheets, multi-layer laminates and molded or shaped articles of virtually all varieties, especially appliance and instrument housings, motor vehicle body panels and other parts and components for use in the automotive and electronics industries, such as radios and pagers.
- the methods of this invention are useful for preparing compositions and molded articles having applications which are the same as or similar to the foregoing.
- compositions of this invention also include those in which (a/b) polycarbonate has been admixed in a composition with (b/b) a poly(phenylene ether) blend.
- the compositions of this invention may optionally contain one or more of the following: (c/b) a vinyl aromatic copolymer, (d/b) an elastomeric impact modifier, and (e/b) a thermoplastic molding polymer selected from polystyrene, polyolefin, polyamide, poly(vinyl chloride), polyurethane and polyacetal.
- Suitable ranges of content for components (a/b) to (e/b) in the compositions of this invention, expressed in parts by weight of the total composition are as follows:
- (a/b) polycarbonate from about 10 parts to about 98 parts, advantageously from about 15 parts to about 95 parts, preferably from about 25 parts to about 93 parts, more preferably from about 35 parts to about 90 parts, and most preferably from about 45 parts to about 90 parts,
- the resulting poly(phenylene ether) content in the final composition is from about 0.2 part to about 30 parts, advantageously from about 0.2 part to about 20 parts, preferably from about 0.2 part to about 15 parts, more preferably from about 0.2 part to about 10 parts, and most preferably from about 0.2 part to about 5 parts,
- thermoplastic molding polymer up to about 95 parts, and preferably from about 1 to about 70 parts.
- compositions of this invention may optionally contain one or more of the following: (c/c) an elastomeric impact modifier, and (d/c) a thermoplastic molding polymer selected from polyester, polystyrene, polyolefin, polyamide, poly(vinyl chloride), polyurethane and polyacetal- Suitable ranges of content for components (a/c) to (d/c) in the compositions of this invention, expressed in parts by weight of the total composition, are as follows:
- thermoplastic molding polymer up to about 95 parts
- compositions of this invention also include those in which (a/d) an acrylate polymer has been admixed in a composition with (b/d) (i) poly(phenylene ether) and/or (ii) a poly(phenylene ether) blend.
- the compositions of this invention may optionally contain one or more of the following: (c/d) a vinyl aromatic copolymer, (d/d) an elastomeric impact modifier, and (e/d) a thermoplastic molding polymer selected from polycarbonate, polyester, polystyrene, polyolefin, polyamide, poly(vinyl chloride), polyurethane and polyacetal.
- Suitable ranges of content for components (a/d) to (e/d) in the compositions of this invention, expressed in parts by weight of the total composition are as follows:
- poly(phenylene ether) blend from about 0.5 part to about 60 parts, advantageously from about 1 part to about 40 parts, preferably from about 1 part to about 30 parts, more preferably from about 1 part to about 25 parts, and most preferably from about 1 part to about 20 parts, provided the resulting poly(phenylene ether) content in the final composition is as set forth in (b)(i), above,
- reaction products if any, of the above named components when admixed in the compositions of this invention.
- the number of parts by weight of the various components which make up the compositions of this invention may, but need not, total to 100.
- compositions of this invention can be accomplished by any suitable mixing means known in the art.
- the substances to be admixed with the polycarbonate/polyester blend are dry blended in particulate form with sufficient agitation to obtain thorough distribution thereof.
- the dry-blended formulation can further be melt mixed, for example in an extruder with or without a vacuum, or otherwise compounded with additional substances.
- Apparatus which can be used in the blending process include, for example, mixing rolls, a dough-mixer or a Banbury mixer.
- compositions of this invention can undergo fabrication and can therein be formed or molded using conventional techniques such as compression, injection molding, gas assisted injection molding, calendering, vacuum forming, thermoforming, extrusion and/or blow molding techniques, alone or in combination.
- the compositions can also be formed, spun or drawn into films, fibers, multi-layer laminates or extruded sheets, or can be compounded with one or more organic or inorganic substances, on any machine suitable for such purpose.
- Articles molded from compositions prepared within the ranges of content stated above exhibit a desirably low level of gloss.
- a polycarbonate such as an aromatic polycarbonate
- an aromatic dihydroxy compound such as a bisphenol
- a carbonate precursor such as a disubstituted carbonic acid derivative, a haloformate (such as a bishaloformate of a glycol or dihydroxy benzene) or a carbonate ester.
- tetrachloroethane tetrachloroethane, chlorobenzene, and chloroform
- tetrahydrofuran, dioxane, nitrobenzene, dimethyl sulfoxide, xylene,cresol or anisole may be added, if desired.
- Caustic soda or other base is then added to the reaction mixture to adjust the pH of the mixture to a level at which the dihydroxy compound is activated to dianionic form.
- a reducing agent such as sodium sulfite or sodium dithionite can also be advantageously added to the reaction mixture as well.
- a carbonate precursor is contacted with an agitated mixture of the aqueous alkaline solution of the dihydroxy compound, and, for such purpose, the carbonate presursor can be bubbled into the reaction mixture in the form of a gas, or can be dissolved and introduced in solution form.
- the mixture is agitated in a manner which is sufficient to disperse or suspend droplets of the solvent containing the carbonate precursor in the aqueous alkaline solution. Reaction at the interface of the organic and aqueous phases created by such agitation yields the bis(carbonate precursor) ester of the dihydroxy compound.
- a coupling catalyst of which the following are representative: a tertiary amine such as triethyl amine or dimethyl amino pyridine; a hindered secondary amine such as diisopropyl amine; a cyclic aza compound such as 2,2,6,6-tetramethyl piperidine or 1 ,2-dimethylimidazole; an amidine or aminoamidine compound such as 1-methyl-2-phenyliminopyrrolidine; an isourea compound such as N,N-dibutyl-N'-phenyl-o-methylisourea; an iminoether or iminocarboxylate compound such as 1-aza-2-methoxy-1-cycloheptene ort-butyl-cyclohexyliminoacetate; or a phosphonium, sulfonium, arson
- the reaction can be run at a pH of 7.01 to 14, and at a temperature between 0°C-100°C, although usually not in excess of the boiling point (reflux temperature) of the solvent used. Frequently, the reaction is run at a temperature of about 0°C to about 45°C.
- the organic and aqueous phases are separated to allow purification of the organic phase and recovery of the polycarbonate product therefrom.
- the organic phase is washed as needed in a centrifuge with dilute base, water and/or dilute acid until free of unreacted monomer, residual process chemicals and/or other electrolytes.
- Recovery of the polycarbonate product can be effected by spray drying, steam devolatilization, direct devolitization in a vented extruder, or precipitation by use of an anti-solvent such as toluene, cyclohexane, heptane, methanol, hexanol, or methyl ethyl ketone.
- aromatic diesters of carbonic acid are condensed with an aromatic dihydroxy compound in a transesterification reaction in the presence of a basic catalyst such as sodium methylate, sodium bisphenolate, calcium acetate, phenyl benzoate, N-stearoylphenothiazine, quaternary ammonium chloride, an alkaline(hydroxy)fluoroborte, an alkali metal salt of benzoic acid, an iminocarboxylic acid, or basic metal oxides such as zinc, lead or antimony oxide.
- the reaction is typically run at 250°C-300°C under vacuum at a progressively reduced pressure of 1-100 mm Hg.
- Aromatic polycarbonate can also be prepared in a homogeneous solution through a process in which a carbonare presursor, such as phosgene, is contacted with a solution containing an aromatic dihydroxy compound, a chlorinated hydrocarbon solvent and a substance, such as pyridine, dimethyl aniline or CaOH, which acts as both acid acceptor and condensation catalyst. Washing with acidified water removes the pyridine and its
- hydrochloride and precipitation and repulping with an antisolvent such as heptane followed by filitration and distillation removes oligomers and unreacted monomer.
- an antisolvent such as heptane
- Yet another process for the preparation of aromatic polycarbonate is the polymerization of cyclic oligomers having a weight average molecular weight of approximately 1,300 at 200°C-300°C, using a catalyst such as lithium stearate ortetramethylammonium tetraphenylborate.
- dihydroxy compounds suitable for the preparation of aromatic polycarbonate include variously bridged, substituted or unsubstituted aromatic diols (or mixtures thereof) represented by the formula
- branched, cyclic or bicyclic (ii) aliphatic or aromatic, and/or (iii) unsaturated, said divalent radical being composed of 1-35 carbon atoms together with up to five oxygen, nitrogen, sulfur, phosphorous and/or halogen (such asfluroine, chlorine and/or bromine) atoms; or (B) S, S 2 , SO, SO 2 , O or CO; or (C) a single bond; and
- each X is independently hydrogen, a halogen (such as fluroine, chlorine and/or bromine), a C 1 -C 12 linear or cyclic alkyl, aikoxy, aryl or aryioxy radical, such as methyl, ethyl, isopropyl, cyclopentyl, cyclohexyl, methoxy, ethoxy, benzyl, tolyl, xylyl, phenoxy and/or xylynoxy.
- a halogen such as fluroine, chlorine and/or bromine
- a C 1 -C 12 linear or cyclic alkyl such as methyl, ethyl, isopropyl, cyclopentyl, cyclohexyl, methoxy, ethoxy, benzyl, tolyl, xylyl, phenoxy and/or xylynoxy.
- the bridging radical represented by Z in the above formula can be a carbon atom to which is bonded one or more groups such as CH 3 , C 2 H 5 , C 3 H 7 , n-C 3 H 7 , i-C 3 H 7 , cyclohexyl, bicyclo[2.2.1]heptyl, benzyl, CF 2 , CF 3 CCI 3 , CF 2 CI, CN, (CH 2 ) 2 COOCH 3 , or PO(OCH 3 ) 2 .
- groups such as CH 3 , C 2 H 5 , C 3 H 7 , n-C 3 H 7 , i-C 3 H 7 , cyclohexyl, bicyclo[2.2.1]heptyl, benzyl, CF 2 , CF 3 CCI 3 , CF 2 CI, CN, (CH 2 ) 2 COOCH 3 , or PO(OCH 3 ) 2 .
- a polycarbonate product can be obtained having a weight average molecular weight, as determined by light scattering or gel permeation chromatography, of 8,000 to 200,000 and preferably 15,000 to 40,000, although values outside these ranges are permitted as well.
- the preferred process of this invention is that in which an aromatic polycarbonate is prepared.
- An aromatic polycarbonate is defined herein with reference to the oxygen atoms, of the one or more dihydroxy compounds present in the polycarbonate chain, which are bonded to a carbonyl carbon. In an aromatic polycarbonate, all such oxygen atoms are bridged by a dihydroxy compound residue some portion of which is an aromatic ring.
- polycarbonate as used herein, are various copolycarbonates, certain of which can be prepared by incorporating one or more different dihydroxy compounds into the reaction mixture. This can be accomplished by charging the dihydroxy compounds themselves to the reaction mixture either simultaneously or
- oligocarbonates are formed separately from one or more different dihydroxy compounds, the oligocarbonates can then be coupled in a condensation reaction to yield a segmented or block copolycarbonate.
- a dicarboxylic acid (or derivative) or a hydroxycarboxylic acid is used in the reaction mixture, or to form an oligomeric prepolymer, instead of one of the different dihydroxy compounds mentioned above, a poly(ester/carbonate) is obtained.
- Copolycarbonates can also be prepared, for example, by reaction of one or more dihydroxy compounds with a carbonate precursor in the presence of a chlorine- or amino-terminated polysiloxane, with a hydroxy-terminated poly(phenylene oxide) or poly(methyl methacrylate), or with phosphonyl dichloride or an aromatic ester of a phosphonic acid.
- Siloxane/carbonate block copolymers are discussed in greater detail in Paul, U.S. Pat. No. 4,596,970 and poly(ester/carbonate)s are discussed in greater detail in Swart, U-S. Pat. No. 4,105,533.
- a polyester may be made by the self-esterif ication of hydroxycarboxylic acids, or direct esterification, which involves the reaction of a diol with a dicarboxylic acid with the resulting elimination of water, giving an -[-AABB-]- polyester. Temperatures applied exceed the melting points of the reactants and typically approach the boiling point of the diol being used, and usually range from about 150oC to about 280°C An excess of the diol is typically used, and once all of the acid has reacted with diol, the excess diol is removed by distillation with the application of additional heat under reduced pressure.
- ester-forming derivatives of a dicarboxylic acid can be heated with a diol to obtain polyesters in an ester interchange reaction.
- Suitable acid derivatives for such purpose are esters, halides, salts or anhydrides of the acid.
- the ester interchange reaction is typically run in the presence of a diluent, for example, an inert organic solvent such as chloroform ortetrachioroethane, and in the presence of a base, for example a tertiary organic base.such as pyridine.
- Typical catalysts used when ester interchange involves alcoholysis are weak bases such as carbonates or alkoxides of sodium, lithium, zinc, calcium, magnesium or aluminum, whereas catalysts such as antimony oxide, titanium butoxide or sodium acetate are often used when acidolysis occurs in the interchange reaction.
- Diol derivatives such as an acetate can be used effectively when it is desired to conduct acidolysis.
- polyester product of intermediate weight can be heated in a vacuum or stream of inert gas, first to a temperature where it crystallizes and then to a temperature close to its melting point.
- Polyesters can also be produced by a ring-opening reaction of cyclic esters or lactones, for which organic tertiary bases and alkali and alkaline earth metals, hydrides and alkoxides can be used as initiators.
- Whether a polyester is crystalline or amorphous is typically a function of the symmetry of the starting materials from which it is made.
- the intermolecular spacing of the resulting molecules may be disrupted if the presence of the substituent creates asymmetric or irregularly shaped molecules.
- the component containing the substituent may also be combined into the polyester molecule in random orientation, resulting in structural irregularity in the polymer chain.
- Factors which can influence crystallization of ring-containing polyesters are the directionality of the ester groups, the stereochemistry of the rings and variations in symmetry where the rings are bridged. For example, a poly(alkylene isophthalate) crystallizes only with difficulty, and a polyester prepared from phthalic acid typically does not crystallize at all.
- a crystalline material may be identified by the endotherm it displays on a differential scanning calorimeter.
- a preferred polyester for use in this invention is a crystalline polyester having a melting point of 254-260°C.
- Suitable reactants for making the polyester used in this invention, in addition to hydroxycarboxylic acids, are diols and dicarboxylic acids either or both of which can be aliphatic or aromatic.
- a polyester which is a poly(alkylene alkanedicarboxylate), a poly(alkylene phenylenedicarboxylate), a poly(phenylene alkanedicarboxylate), or a poly(phenylene phenylenedicarboxylate) is therefore appropriate for use herein.
- Alkyl portions of the polymer chain can be substituted with, for example, halogens, alkoxy groups or alkyl side chains and can contain divalent heteroatomic groups (such as -O-, -S- or-SO 2 -) in the paraffinic segment of the chain.
- the chain can also contain unsaturation and non-aromatic rings.
- Aromatic rings can contain substituents such as halogens, alkoxy or alkyl groups, and can be joined to the polymer backbone in any ring position and directly to the alcohol or acid functionality or to intervening atoms.
- Typical alkylene diols used in ester formation are the C 2 -C 10 glycols, such as ethylene-, propylene-, and butylene glycol.
- Alkanedicarboxylic acids frequently used are oxalic acid, adipic acid and sebacic acid.
- Diols which contain rings can be, for example, a 1,4-cyclohexylenyl glycol or a 1,4-cyclohexane-dimethylene glycol, resorcinol, hydroquinone, 4,4'-thiodiphenol, bis-(4-hydroxyphenyl)sulfone, a dihydroxynaphthalene, a xylylene diol, or can be one of the many bisphenols such as 2,2-bis-(4-hydroxyphenyl)propane.
- Aromatic diacids include, for example, terephthalic acid, isophthalic acid, naphthalenedicarboxylic acid, diphenyletherdicarboxylic acid, diphenyldicarboxylic acid, diphenylsulfonedicarboxylic acid, diphenoxyethanedicarboxylic acid.
- polyester in addition to polyesters formed from one diol and one diacid only, the term "polyester” as used herein includes random, patterned or block copolyesters, for example those formed from two or more different diols and/or two or more different diacids, and/or from other divalent heteroatomic groups. Mixtures of such copolyesters, mixtures of polyesters derived from one diol and diacid only, and mixtures of members from both of such groups, are also all suitable for use in this invention, and are all included in the term "polyester”.
- PETG clear, amorphous copolyester
- PCTG liquid crystalline polyesters derived from mixtures of 4-hydroxybenzoic acid and 2-hydroxy-6-naphthoic acid; or mixtures of terephthalic acid, 4-hydroxybenzoicacid and ethylene glycol; or mixtures of terephthalic acid, 4-hydroxybenzoic acid and 4,4'-dihydroxybiphenyl.
- a poly(phenylene ether) [also known as a poly(phenylene oxide)] is a polymer comprising a plurality of structural units described generally by the formula
- each Q 1 is independently hydrogen, halogen, primary or secondary
- each Q 2 is independently hydrogen, halogen, primary or secondary C 1 - C 8 lower alkyl, phenyl, haloalkyl, hydrocarbonoxy or halohydrocarbonoxy as defined for Q 1 .
- Suitable primary lower alkyl groups are methyl, ethyl, n-propyl, n-butyl, isobutyl, n-amyl, isoamyl, 2-methyl butyl, n-hexyl, 2,3-dimethylbutyI, 2-, 3- or 4-methylpentyl and the corresponding heptyl groups.
- secondary lower alkyl groups are isopropyl, sec-butyl and 3-pentyl. It is preferred that any alkyl radicals are straight chain rather than branched. Most often, each Q 1 is alkyl or phenyl, especially C 1 -4 alkyl, and each Q 2 is hydrogen. Both homopolymer and copolymer poly(phenylene ether)s are included, as well as mixtures or blends thereof. Suitable homopolymers are those containing, for example, 2,6-dimethyl-1,4-phenylene ether units. Suitable copolymers include random copolymers containing such units in combination with, for example, 2,3,6-trimethyl-1 ,4-phenylene ether units.
- poly(phenylene ether)s containing moieties which modify properties such as molecular weight, melt viscosity and/or impact strength.
- Such polymers may be prepared by copolymerizing with or grafting onto the poly(phenylene ether), in known manner, such vinyl monomers as vinyl nitrile compounds (e.g. acrylonitrile) and vinyl aromatic compounds (e.g., styrene), or such polymers as polystyrenes and elastomers.
- the product typically contains both grafted and ungrafted moieties.
- Suitable polymers are the coupled poly(phenylene ether)s in which the coupling agent is reacted, in known manner, with the hydroxy groups of two poly(phenylene ether) chains to produce a higher molecular weight polymer containing the reaction product of the hydroxy groups and the coupling agent.
- Illustrative coupling agents are low molecular weight polycarbonates, quinones, heterocycles, formals and poly(phenylene sulfide)s.
- poly(phenylene ether)/polycarbonate copolymers are known and are discussed in U.S. Pat. No. 5,010,143, which is incorporated herein.
- the poly(phenylene ether) typically has a number average molecular weight within the range of about 3,000-40,000, and a weight average molecular weight within the range of about 20,000-80,000, as determined by gel permeation chromatography. Its intrinsic viscosity is typically in the range of about 0.15-0.6, and preferably at least 0.25, dL/g, as measured in chloroform at 25°C. However, values outside these ranges are permitted as well.
- the poly(phenylene ether)s are typically prepared by the oxidative coupling of at least one corresponding monohydroxyaromatic compound.
- Particularly useful and readily available monohydroxyaromatic compounds are 2,6-xylenol (wherein each Q' is methyl and each Q 2 is hydrogen), whereupon the polymer may be characterized as a poly(2,6-dimethyl-1 ,4-phenylene ether), and 2,3,6-trimethylphenol (wherein each Q 1 and one Q 2 is methyl and the other Q 2 is hydrogen).
- catalyst systems are known for the preparation of poly(phenylene ether)s by oxidative coupling. For the most part, they contain at least one heavy metal compound such as a copper, manganese or cobalt compound, usually in combination with various other materials.
- a first class of preferred catalyst systems consists of those containing a copper compound, such as are disclosed, for example, in U.S. Pat. Nos. 3,306,874, 3,306,875, 3,914,266 and 4,028,341, each of which is incorporated herein. They are usually combinations of cuprous or cupric ions, halide (i.e., chloride, bromide or iodide) ions and at least one amine.
- Catalyst systems containing manganese compounds constitute a second preferred class. They are generally alkaline systems in which divalent manganese is combined with such anions as halide, alkoxide or phenoxide. Most often, the manganese is present as a complex with one or more complexing and/or chelating agents such as dialkylamines, alkanolamines, alkylenediamines,
- ⁇ -hydroxyoximes (monomeric and polymeric), o-hydroxyaryl oximes and ⁇ -diketones. Also useful are known cobalt-containing catalyst systems.
- a poly(phenylene ether) blend may be prepared by blending a poly(phenylene ether) with polystyrene, a vinyl aromatic copolymer, and/or with other non-styrenic polymers as specified below.
- the poly(phenylene ether) blend made up of about 20 to about 99 parts poly(phenylene ether), and preferably about 30 to 90 parts poly(phenylene ether), by weight, with the balance being made up of polystyrene, a vinyl aromatic copolymer, and/or the non-styrenic polymers, in addition to additives such as dyes and pigments.
- a preferred formulation of the poly(phenylene ether) blend contains about 30 to about 85 weight parts poly(phenylene ether), about 15 to about 70 weight parts selected from one or more of the following:
- polystyrene high impact polystyrene, styrene/butadiene/styrene and/or styrene/ethylene- butylene/styrene block copolymer, and about 0.1 to about 20 weight parts pigments and/or dyes.
- a polystyrene includes polymers prepared by bulk, suspension or emulsion polymerization which contain at least 25 percent by weight structural units derived from a monomer described generally by the formula
- PZ 5 (where Z is H, halogen, O, -OH, -CO 2 H, -SH, -CN, -NO 2 oran epoxide ring; or a C 1 - C 10 linear or branched, saturated or unsaturated, alkyl radical or a C 6 - C 14 aryl radical substituted with halogen, -OH, -CO 2 H, -SH,
- SAN styrene/acrylonitrile copolymer
- SAN which has been rubber modified is also suitable for use as a blend material, and an example of a rubber modified SAN is a vinyl
- ABS an elastomeric-thermoplastic composite
- ABS is typically formed by the grafting of an SAN copolymer onto a polybutadiene substrate latex.
- the polybutadiene forms particles of rubber - the elastomeric component - which are dispersed as a discrete phase in a thermoplastic matrix formed by the SAN.
- the rubber content of a rubber-modified styrene/acrylonitrile copolymer employed in the compositions of this invention can be up to 80 percent, but is preferably less than 40 percent.
- the preferred ratio of styrene to acrylonitrile in the styrene-acrylonitrile solution is about 99/1 to about 60/40, and in the preferred recipe the rubber component constitutes from about 4% to less than about 40% of the product.
- numerous other vinyl aromatic compounds will function in a manner equivalent to that of styrene, to-wit: alphamethyl styrene, vinyl-toluene, vinylxylene, vinylethyl benzene or vinylchloro benzene.
- Methacrylonitrile is but one of many other other vinyl nitrile monomers which will serve in the place of, or in conjunction with, acrylonitrile.
- a vinyl aromatic copolymer for blending with poly(phenylene ether), is a block copolymer which can be either linear, branched, radial or teleblock, and can be either a di-block (“A-B”) copolymer, tri-biock (“A-B-A”) copolymer, or radial teleblock copolymer with or without tapered sections, i.e. portions of the polymer where the monomers alternate or are in random order close to the point of transition between the A and B blocks.
- the A portion is made by polymerizing one or more vinyl aromatic hydrocarbon monomers, and has an average molecular weight of about 4,000 to about 115,000, and a weight preferably of about 8,000 to about 60,000.
- the block copolymers used herein can also desirably be hydrogenated to reduce the degree of unsaturation on the polymer chain and on the pendant aromatic rings.
- the block copolymer may be selectively hydrogenated by hydrogenating only the elastomeric block B.
- Typical hydrogenation catalysts utilized are Raney nickel, molybdenum sulfide, finely divided palladium and platinum oxide. The hydrogenation reaction is typically run at75-450°Fand at 100-1,000 psig for 10-25 hours.
- the most preferred vinyl aromatic block copolymers are vinyl
- a PPE Blend represents a poly(phenylene ether) concentrate because poly(phenylene ether) is typically present in the PPE Blend at a higher level of content than it will be in the final composition of which the PPE Blend itself becomes a part.
- the desired level of content of poly(phenylene ether) in a composition of this invention is reached by diluting the amount of poly(phenylene ether) in the concentrate by the admixture of other
- polystyrene and/or a vinyl aromatic copolymer in a PPE Blend imparts to the poly(phenylene ether) concentrate a processing temperature and/or viscosity which are lower than that of poly(phenylene ether) by itself, the concentrate may be added to the final composition directly at the molding machine rather than in the pre-molding extruded mixture.
- an -[-AABB-]- type polyamide is obtained wherein the diamine and diacid units alternate.
- a monomer such as an amino acid or a cyclic lactam
- an -[-AB-]- type polyamide results from a regular head-to-tail polymerization, similar to an addition mechanism.
- nylon-6 heat is applied to raise the temperature of the caprolactam to 240-280oC, and catalysts such as water and phosphoric acid are added to the system. Hydrolysis ensues, the ring opens and polymerization takes place while unreacted monomer is removed from the system and recycled. Polycondensation and growth of the polymer chain results from the removal of water from the system.
- the acrylate When an acrylate and a methacrylate are copolymerized, the acrylate, each can be used in the mix of reactants from which the copolymer results in an amount of up to about 99.0 parts by weight, based on the total weight of the copolymer.
- the acrylate polymer in a poly(phenylene ether) blend takes the form of a copolymer of an acrylate and a methacrylate
- the copolymer may be a random, alternate, block or grafted copolymer.
- An acrylate copolymer may be prepared using the methods described above by copolymerization of an alkyl acrylate, an alkyl methacrylate, or a mixture thereof, with one or more other copolymerizable, ethylenically unsaturated monomers.
- the term "acrylate copolymer” as used herein is not therefore intended to limit the content of such copolymer, which, as described in the preceding sentence, includes copolymers which can contain methacrylates in additon to other copolymerizable monomers, and which are copolymers by reason of being prepared from more than one monomer.
- any ethylenically unsaturated monomer capable of homopolymerization underthe conditions described above can be copolymerized with an acrylate, a methacrylate, or both.
- -CO 2 Z (11) -CO 2 NZ 2 ; (12) -OZ; (13) -SZ; (14) -SOZ; (15) -SO 2 Z; (16) -NZ 2 ; or (17) - PZ 5 (where Z is H, halogen, O, -OH, -CO 2 H, -SH, -CN, -NO 2 , oran epoxide ring; or a C 1 - C 10 linear or branched, saturated or unsaturated, alkyl radical or a C 6 - C 14 aryl radical substituted with halogen, -OH, -CO 2 H, -SH,
- Monomers of particular interest for copolymerization with an acrylate and/or a methacrylate include phenyl maleimide, styrene or a C 1 -C 10 alkyl or halogen substituted styrene, acrylonitrile or a C 1 -C 10 alkyl or halogen substituted acrylonitrile, maleic anhydride, a C 1 -C 12 diene, or a mixture thereof.
- compositions of this invention may be used in the compositions of this invention.
- elastomeric impact modifiers useful in the compositions of this invention are thermoplastic elastomers, emulsion-type, core-shell graft copolymer elastomers, and olefinic elastomers.
- Thermoplastic elastomers are those which are characterized, for example, in that they can be melted and recooled, or dissolved and reformed upon removal of the solvent, without undergoing any significant change in properties.
- Thermoplastic elastomers are also characterized by the randomness of the shape and size they take on when mixed by shearing forces with the other components making up the compositions of this invention, especially when heat is applied during such mixing.
- thermoplastic elastomer is typically a long chain molecule, segments of a thermoplastic elastomer in the polymer composition matrix are generally elongated, linear ribbons or bands. The molecules tend to fuse and flow together in a continuous structure. However, chain coiling can yield globule-shaped segments of thermoplastic elastomer in the matrix.
- the random shape and size assumed in the polymer compositon matrix by a thermoplastic elastomer is to be distinguished from the shape and size assumed by a core-shell graft copolymer.
- a core-shell graft copolymer is typically present in the polymer matrix in a bead shape both before and after mixing by application of shearing forces, whether heat is used or not, and is usually present in a rather narrow size range, for example 0.05-0.8 microns.
- the retention of this core-shell, or spherical, shape by the graft polymer, even after heating and mixing, results from the fact that the outer layers, which surround the core, are formed by grafting appropriate monomers onto the core.
- a core-shell graft copolymer typically cannot be melted and recooled without a significant change in properties because the graft polymer will tend to decompose or crosslink, and the bead-shaped segments of graft polymer will tend to agglomerate upon melting, making dispersion of them by mixing difficult.
- Linear, branched, radial or teleblock A-B-A or A-B block copolymer thermoplastic elastomers can also be prepared from materials other then vinyl aromatic systems. These other copolymers also have a rigid block "A" having a T g above room temperature (approximately 23-25°C) and a rubbery block "B” having a T g below room temperature. Examples of typical pairings of the various materials used to form the respective A and B blocks of such other block copolymerthermoplastic elastomers are shown below in Table
- Block copolymerthermoplastic elastomers can be prepared, for example, by anionic polymerization using an alkyl-lithium initiator.
- Thermoplastic elastomers based on urethane arediscussed in greater detail in Schollenberger, USP 3,015,650 and Saunders, USP 3,214,411 ; and those based on copolyester-etherare discussed in Witsiepe, USP 3,651,014, each of which is incorporated herein.
- core-shell graft copolymer elastomers suitable for use herein are those which can be based on either a diene rubber, an acrylate rubber or on mixtures thereof.
- a diene rubber contains a substrate latex, or core, which is made by polymerizing a diene, preferably a conjugated diene, or by copolymerizing a diene with a mono-olefin or polar vinyl compound, such as styrene, acrylonitrile, or an alkyl ester of an unsaturated carboxylic acid such as methyl methacrylate.
- the substrate latex is typically made up of about 40-85% diene, preferably a conjugated diene, and about 15-60% of the mono-olefin or polar vinyl compound.
- the elastomeric core phase should have a glass transition temperature ("T g ") of less than about 10°C, and preferably less than about -20oC.
- a mixture of ethylenically unsaturated monomers is then graft polymerized to the substrate latex.
- monomers such as vinyl toluene or vinyl chloride; vinyl aromatics such as styrene, alpha-methyl styrene or haloge ⁇ ated styrene; acrylonitrile, methacrylonitrile oralpha-halogenated acrylonitrile; a C 1 -C 8 alkyl acrylate such as ethyl acrylate or hexyl acrylate; a C 1 -C 8 alkyl methacrylate such as methyl methacrylate or hexyl methacrylate; glycidyl methacrylate; acrylic or methacrylic acid; and the like or a mixture of two or more thereof.
- the grafting monomers may be added to the reaction mixture simultaneously or in sequence, and, when added in sequence, layers, shells or wart-like appendages can be built up around the substrate latex, or core.
- the monomers can be added in various ratios to each other although, when just two are used, they are frequently utilized in equal amounts.
- a typical weight ratio for methyl methacrylate/butadiene/styrene copolymer (“MBS" rubber) is about 60-80 parts by weight substrate latex, about 10-20 parts by weight of each of the first and second monomer shells.
- a preferred formulation for an MBS rubber is one having a core built up from about 71 parts of butadiene, about 3 parts of styrene, about 4 parts of methyl methacrylate and about 1 part of divinyl benzene; a second phase of about 1 1 parts of styrene; and a shell phase of about 1 1 parts of methyl methacrylate and about 0.1 part of 1,3-butylene glycol di methacrylate, where the parts are by weight of the total composition.
- a diene-based, core-shell graft copolymer elastomer and methods for making same, as described above, are discussed in greater detail in Saito, USP 3,287,443, Curfman, USP 3,657,391, and Fromuth, USP 4,180,494.
- An acrylate rubber has a first phase forming an elastomeric core and a second phase forming a rigid thermoplastic phase about said elastomeric core.
- the elastomeric core is formed by emulsion or suspension polymerization of monomers which consist of at least about 50 weight percent alkyl and/or aralkyl acrylates having up to fifteen carbon atoms, and, although longer chains may be used, the alkyls are preferably C 2 -C 6 , most preferably butyl acrylate.
- the elastomeric core phase should have a T g of less than about 10°C, and preferably less than about -20°C.
- a portion of the chains which make up the rigid thermoplastic phase are chemically bonded to the elastomeric core. It is preferred that there be at least about 20% bonding of the rigid thermoplastic phase to the elastomeric core.
- a preferred acrylate rubber is made up of more than about 40% to about 95% by weight of an elastomeric core and about 60% to about 5% of a rigid thermoplastic phase.
- the elastomeric core can be polymerized from about 75% to about 99.8% by weight C 1 -C 6 acrylate, preferably n-butyl acrylate.
- the rigid thermoplastic phase can be polymerized from at least 50% by weight of C 1 -C 8 alkyl methacrylate, preferably methyl methacrylate. Acrylate rubbers and methods for making same, as described above, are discussed in greater detail in Owens, USP 3,808,180 and Witman, USP 4,299,928.
- Core-shell grafted copolymeric elastomers also include a vinyl nitrile/diene/vinyl aromatic copolymer, as described above with relation to the vinyl aromatic copolymers includable in a poly(phenylene ether) blend, having an elastomeric core which is greater than 40 percent by weight of the copolymer.
- Olefinic elastomers useful as an impact modifier in the compositions of this invention are based generally on a long-chain, hydrocarbon backbone, which may or may not be grafted with one or more vinyl monomers.
- Representative examples ofa few olefinic elastomers which illustrate the variation in the known substances which would suffice for such purpose are as follows: butyl rubber; chlorosulfonated polyethylene rubber;
- polytetrafluoroethylene polytetrafluoroethylene
- neoprene rubber nitrile rubber
- polybutadiene polyisoprene
- the olefinic elastomer used herein may also contain reactive moieties.
- a reactive olefinic elastomer may, for example, be a polymer which has a glass transition temperature (T g ) less than 0°C formed from (I) (A) at least one olefin monomer such as ethylene, propylene, isopropylene, butylene or isobutylene, or at least one conjugated diene such as butadiene, and the like, or mixtures thereof, or (B) a copolymer of one or more olefin monomers, such as described above, with other vinyl monomer(s), but containing a sufficient amount of the olefin monomer(s) to impart a T g of less than 0°C to the reactive olefinic elastomer; (II) at least one vinyl (i.e.
- vinyl (i.e. olefinically unsaturated, including vinylidene) monomers useful as the optional component (III) in forming the polymeric reactive olefinic elastomer useful in this invention include the following: vinyl compounds (especially when they bear a polar, electronegative group or functionality) such as vinyl toluene, alphamethyl styrene, halogenated styrene; those containing nitrile groups such as copolymers of acrylonitrile, methacrylonitrile or alpha-haiogenated acrylonitrile; a C 1 -C 8 alkyl acrylate or methacrylate such as ethyl acrylate, butyl acrylate, hexyl acrylate, hydroxy ethyl acrylate, methyl methacrylate or hexyl methacrylate; acrylic or methacrylic acid; the vinylidene monomers, especially when they bear a polar, electronegative group or functionality such as a
- vinyl and vinylidene monomers from groups such as the vinyl and vinylidene -esters, -ethers, -organic acids, -aromatics, -alcohols, -anhydrides, -halides, -nitriles and -amides; or mixtures of any of the foregoing may be used. Additionally, any one or more of the foregoing monomers may be copolymerized with carbon monoxide.
- Vinyl monomers such as the foregoing may also be copolymerized as part of the olefin copolymer described above as component (l)(B); or, when carrying an epoxide group, may be used as the component (II). Or, the epoxide group may be carried on an olefin monomer.
- Suitable olefinically unsaturated monomers containing epoxide groups for use as component (II) of the terpolymeric reactive olefinic elastomer include, for example, glycidyl esters of unsaturated carboxylic acids (glycidyl methacrylate); glycidyl ethers of unsaturated alcohols (allyl-glycidyl-ether) and of alkenyl phenols (isopropenylphenyl-glycidylether); and vinyl and allyl esters of epoxycarboxylic acids (vinyl esters of epoxidized oleic acid).
- all compounds which contain both a polymerizable unsaturated group and reactive epoxide groups in the molecule can be used for preparation of the reactive olefinic elastomer of the invention.
- Copolymers of 1-25 percent (by weight) of glycidyl methacrylate, 40-95 percent of ethylene, and
- Copolymers containing epoxide groups may be obtained according to known processes, for example by radical polymerization in chlorobenzene at 80°C in 50% strength solution.
- monomers such as listed above are dissolved in an appropriate solvent, such as benzene, chlorobenzene or toluene, and polymerized at a temperature of about 80°C by adding azobisisobutyronitrile, whereby oxygen is excluded.
- the solvent used is distilled off (e.g., chlorobenzene at 100°C and 20 torr) and the residue is dried in vacuum at 100°C and then powdered.
- the terpolymeric reactive olefinic elastomer of this invention can also be prepared in gas phase under conditions suitable for polymerizing an olefin.
- the terpolymer can be made in either a tubular reactor or a stirred autoclave, where heated, pressurized feed streams of olefin or vinyl monomer gas, peroxide free-radical initiator and chain transfer agent are injected into the reaction device.
- the reaction of formation usually occurs at 1 ,500-3,000 atm (152-304 MPa) and at a temperature usually not exceeding 300°C, as known in the art.
- the molecular weight of the reactive olefinic elastomer is typically between about 10,000 and about 500,000, preferably between about 30,000 and about 200,000, and it typially contains about 5 to about 1 ,000, preferably about 20 to about 500, epoxide groups per macromolecule.
- thermoplastic molding polymers may optionally be included as components in the compositions of this invention. These polymers include polystyrene, polyamide, polyolefin, poly(vinyl chloride), polyurethane, poly(methyl methacrylate) and polyacetal, ora mixture of any of same. Polystyrene, poly(methyl methacrylate) and polyamide have been described above.
- a polyolefin may be any of the several different kinds mentioned below including, for example, linear low density polyethylene (“LLDPE”).
- LLDPE is formed under the kind of low oressure conditions which are usually employed for forming high density polyethylene (“HDPE”).
- HDPE high density polyethylene
- a low density product (0.910 - 0.940 g/cm 3 ) results because, ratherthan forming a homopolymer, ethylene is copolymerized with one or more ⁇ -olefins, which in the final product take on the form and function of short side chains.
- LDPE low density polyethylene
- LLDPE can be formed in a slurry using a light hydrocarbon diluent and a supported chromium catalyst, or it can be formed as a slurry in hexane using organometal-titanium type catalysts. It can also be formed in cyclohexane in solution at a relatively high temperature, approximately 250°C, using as a catalyst a combination of tributyl aluminum, titanium tetrachloride and vanadium oxychioride. LLDPE can also be formed in gas phase using a fluidized bed of growing polymer particles to which a supported chrominum oxide catalyst modified with titanium and fluoride is charged, as described in Levine, USP 4,011 ,382
- LDPE is typically thought of as that which is made under high pressure conditions and has a density between about 0.916 to about 0.930 g/cm 3 . This low density results from the many zones of amorphous arrangement which are characteristic of LDPE because of its long chain branches, which can contain thousands of carbon atoms.
- LDPE can be made in either a tubular reactor or a stirred autoclave, where heated, pressurized feed streams of ethylene gas, peroxide free-radical initiator and chain transfer agent are injected into the reaction device. The reaction of formation usually occurs at 1,500-3,000 atm (152-304 MPa) and at a temperature usually not exceeding 300°C, as known in the art.
- LDPE can be copolymerized with monomers such vinyl acetate, ethyl acrylate, acrylic acid or other polar vinyl monomers.
- An HDPE homopolymer is typically about 94% crystalline and has a density of about 0.950 to about 0.970 g/cm 3 .
- HDPE because of its much greater crystallinity and density, has a higher melting point than LDPE - 135°C vs. 115°C.
- the molecular weight of HDPE usually ranges from 50,000 to 1 ,000,000 or more.
- ZPE Ziegler process polyethylene
- ZPE has great versatility because of the wide range of molecular weights in which it can be prepared using the versatile Ziegler catalyst.
- ZPE can include, for example, waxes ranging in molecular weight from 10,000 to ultrahigh molecular weight HDPE having a molecular weight of several million.
- ZPE has a density of about 0.940 to about 0.965 g/cm 3 .
- Both supported and non-supported magnesium-titanium catalyst systems find wide use in the manufacture of ZPE, for example the magnesium dialkyls described in Birkelbach, USP 4,120,820 (Dow).
- Ziegler catalysts useful in making polyethylene are those formed by the reaction of organosilols with chromium trioxide, such as described in Baker, USP 3,324,101 (Union Carbide).
- Ziegler catalysts can be successfully used in suspension, or slurry, systems where the temperature is kept below 110°C and is run at about 0.5 to 2 MPa to avoid solution in the diluent. In solution polymerization, the system is operated at about 150 - 250°C and at about 2 - 4 MPa. Gas-phase polymerization, which is run at 70 - 1 10°C and at 2 - 3 MPa, does not use a hydrocarbon solvent or diluent.
- the preparation of polypropylene also involves the use of Ziegler catalysts, which allows the stereo regular polymerization of propylene to form isotactic polypropylene.
- the catalyst used is typically a titanium trichloride in combination with aluminum
- Polymercaptans and other isocyanate-reactive compounds are also suitable in the present invention.
- Polyisocyanate polyaddition active hydrogen containing compounds are particularly preferred for use with the present invention.
- PIPA compounds are typically the reaction produrts of TDI and triethanolamine.
- a method for preparing PIPA compounds can be found in, for example. United States Patent 4,374,209, issued to Rowlands.
- copolymer polyols are base polyols containing stably dispersed polymers such as acrylonitrile-styrene copolymers.
- copolymer polyols can be from reaction mixtures comprising a variety of other materials, including, for example, catalysts such as azobisisobutyronitrile; copolymer polyol stabilizers; and chain transfer agents such as isopropanol.
- catalysts such as azobisisobutyronitrile
- copolymer polyol stabilizers such as polystyrene
- chain transfer agents such as isopropanol.
- Polyurethane formulations containing the above compounds are commonly commercially available.
- a polyacetal is a polymer which arises by the bond opening and polymerization of the carbonyl group of an aldehyde.
- a variety of flame or ignition resistance additives may be advantageously include in the compositions of this invention.
- Representative examples thereof include antimony oxides; sodium antimonate; metal borates (particularly zinc); boric acid; alumina trihydrate; ammonium fluoroborate; molybdenum oxide; halogenated hydrocarbons;
- decabromomdiphenyl oxide 1,2-bis(2,4,6-tribromophenoxy) ethane; halogenated carbonate oligomers; halogenated diglycidyl ethers; tetrabromo phthalic anhydride; inorganic phosphorous compounds such as ammonium phosphates; organophosphorous compounds such as alkyl acid phosphates, trialkyl phosphates (such astriethyl), dimethyl methyl phosphonate, halogenated alkyl phosphates and phosphonates such as 1 ,3-dichloro-2-propanol phosphate, diphosphates, 3,9-tribromoneopentoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro(5.5)undecane-3,9-dioxide, oligomeric cyclic and phenyl phosphonates (including halogenated), trisaryl phosphates (including halogenated),
- compositions of this invention for protection against thermal, oxidative and ultra-violet degradation.
- thermal and oxidative stabilizers which can be advantageously utilized are hindered phenols, hydroquinones, phosphites, including substituted members of those groups and/or mixtures of more than one thereof.
- a preferred phenolic anti-oxidant is IrganoxTM 1076 anti-oxidant, available from Ciba-Geigy Corp.
- Ultra-violet stabilizers such as various substituted resorcinols, salicylates, benzotriazoles, benzophines, hindered amines and hindered phenols can also be usefully included in the compositions hereof, as can be lubricants, colorants, fillers such as talc, clay, phosphate, metal, inorganic or graphite fibers, or mica, dyes, pigments, mold release agents, and reinforcement agents such as fiberglass or phosphate, metal, inorganic or graphite fibers. Additives and stabilizers of the same or a similar kind as the foregoing are known, and the use and selection thereof is within the skill in the art. However, such additives, if used, typically do not exceed 15 percent by weight of the total composition, except fillers or reinforcing agents, which may constitute up to 40 percent of the composition.
- the polycarbonate/polyester compositions prepared in Controls Aa to La and Examples 1a to 26a are made by dry blending the ingredients thereof and agitating same in a paint shaker for 7 minutes. The dry blended formulations are then melt mixed in a vented 30mm Werner-Pffeiderer co-rotating, twin screw extruder using a 240 rpm speed and a set temperature of 290°C. Each extruded composition is passed through a water bath, chopped into granules and collected for molding. Granules are thoroughly dried in a circulated air oven at 120°Cfor4to 6 hours priorto molding. All testing samples are prepared by injection molding on a 75 ton (6.8 ⁇ 10 4 kg) Arburg molding machine. Molding temperatures for the barrel and mold are set at 290°C and 175°F, respectively. Testing samples for gloss
- PC is a polycarbonate having a meltflow rate of 13, as determined according to ASTM Designation D 1238-89, Condition 300/1.2, available from The Dow Chemical Company;
- PET I is TratufTM 9506 polyethylene terephthalate) having an 0.95 intrinsic viscosity, available from Goodyear Tire and Rubber Company;
- PPE IV is unalloyed poly(phenylene ether), available from Aldrich;
- PPE/PMMA blend is a 50/50 weight ratio blend of poly(phenylene ether) and poly(methyl methacrylate), prepared by melt mixing a dry mix of the two polymers at 300°C, the poly(methyl methacrylate) having a heat deflection temperature under load at 264 psi of 199°F, determined according to ASTM Designation D648-82, and being available from Rohm & Haas Company;
- “KratonTMG 1702" copolymer is a hydrogenated styrene/butadiene di-block thermoplastic elastomeric copolymer, available from Shell Oil Company;
- ABS 19 is mass produced acrylonitrile/butadiene/styrene copolymer having approximately 20 percent rubber, available from The Dow Chemical Company;
- Reactive PS is a polystyrene which incorporates 1 weight percent C 3 NOH 4 oxazoline ring onto the polystyrene backbone, available from The Dow Chemical Company;
- VistalonTM 3708 copolymer is an ethylene/propylene/diene monomer thermoplastic elastomer, available from Exxon Corp.;
- Carbon black is powdered black pigment
- IR 1076 is phenolic anti-oxidant stabilizer, available from Ciba-Geigy Corporation;
- BC-52 is Tetrabromo Bisphenol-A carbonate oligomer, available from Great Lakes Chemical, Inc.;
- TPP istriphenyl phosphate, available from Akzo Chemicals, Inc.
- Control La and Example 26a polycarbonate, polyester and KratonTMG 1651 copolymer were pre-extruded and added to the poly(phenylene ether) alloy (PPE III) at the molding machine as a salt-and-pepper blend.
- PPE III poly(phenylene ether) alloy
- Gloss measurements are performed on testing samples according to ASTM Designation D 523-85 using a Dr. Lange Reflectometer RB3 available from Hunter Assocaiates.
- Controls Aa to La are indicated by C-Aa, C-Ba, C-Ca etc.
- Examples 1 a to 26a are indicated by E-1 a, E-2a, E-3a etc.
- poly(phenylene ether) Small quantities of poly(phenylene ether), 5 weight percent of the composition or less (for example 4.5 weight percent or less, or 3 weight percent or less), are typically sufficient to achieve this effect.
- the presence of poly(phenylene ether) does not detract from the effect of ignition resistance additives in the blend, as shown by Example 9a.
- the samples molded from Examples 1a to 26a also showed uniform color with reduced pearlescence, high weldline strength and were characterized by reduced delamination effects.
- the composition of Example 1a had reduced die swell which indicates fine dispersion of the two phases and results in enhanced processibility.
- Examples of several preferred embodiments wherein a vinyl aromatic copolymer is the matrix resin in the compositions of this invention are setforth below. It is not intended, however, that these examples (Examples 1 c to 27c) should in any manner restrict the scope of this invention. Some of the particularly desirable features of this invention may be seen by contrasting the characteristics of Examples 1 c to 27c with those of various controlled formulations (Controls Ac to Kc) which do not possess the features of, and are not therefore embodiments of, this invention.
- the vinyl aromatic copolymer compositions prepared in Controls Ac to Kc and Examples 1c to 27c are made by dry blending the ingredients thereof and agitating same in a paint shaker for 7 minutes. The dry blended formulations are then melt mixed in a vented 30mm Werner-Pfieiderer co-rotating, twin screw extruder using a 250 rpm speed and a set temperature of 240-280°C. Each extruded composition is passed through a water bath, chopped into granules and collected for molding. Granules are thoroughly dried in a circulated air oven at85°Cfor4to 6 hours prior to molding. All testing samples are prepared by injection molding on a 75 ton (6.8 ⁇ 10 4 kg) Arburg molding machine. Molding temperatures for the barrel and moid are setat240-260°Cand 130-150°F, respectively. Testing samples for gloss measurement are molded in the form ofa 2.5 in ⁇ 6.5 in plaque.
- Carbon black is powdered black pigment
- PET is TratufTM 9506 poly(ethylene terephthalate) having an 0.95 intrinsic viscosity, available from Goodyear Tire and Rubber Company.
- Controls Ac to Kc are indicated by C-Ac, C-Bc, C-Cc etc.
- Examples 1c to 27c are indicated by E-1c, E-2c, E-3c etc.
- the results of the tests performed on the plaques molded from the compositions of Controls Ac to Kc and Examples 1 c to 23c demonstrate the lower level of gloss, particularly at 20°, which characterizes the plaques molded from the compositions containing poly(phenylene ether).
- Examples 24c to 27c demonstrate lower gloss levels of compositions containing blends of styrenic copolymers with other thermoplastic resins and low levels of poly(phenylene ether). Small quantities of poly(phenylene ether), 5 weight percent of the composition or less (for example 4.5 weight percent or less, or 3 weight percent or less), are typically sufficient to achieve this effect. The presence of poly(phenylene ether) does not detract from the effect of ignition resistance additives in the blend.
- the samples molded from Examples 1c to 27c showed uniform color with reduced pearlescence and were characterized by reduced gloss.
- PPE/ABS blend is a 50/50 weight ratio blend of poly(phenylene ether) and the acrylonitrile/butadiene/styrene copolymer used as component 2, prepared by melt mixing a dry mix of the two polymers at 300°C; and
- (6) Vectra"' DPX-518" copolymer is a styrene/butadiene/styrenetriblock elastomer, available from Dexco;
- (12) TinuvinTM 327 stabilizer is a phenolic ultra violet light stabilizer, available from Ciba-Geigy Corporation;
- (13) ChimassorbTM 944 FL stabilizer is a polymeric hindered amine ultra violet light stabilizer, available from Ciba-Geigy Corporation;
- (15) BC-52 is Tetrabromo Bisphenol-A carbonate oligomer, available from Great Lakes Chemical, Inc.;
- TPP istriphenyl phosphate, available from Akzo Chemicals, Inc.; and "(17) TeflonTM 6C” polymer is a fibril form of polytetrafluoroethylene), available from E.l. duPontde Nemours & Co.
- Examples 7d to 10d are indicated by E-7d, E-8d, E-9d and E-10d. Gloss measurements are also performed on the testing samples molded from the compositions of Examples 7d to 10d, and the U.L.94 burn test is performed on the sample molded from
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JP5516607A JPH07507080A (en) | 1992-03-10 | 1993-03-10 | Polyphenylene ether modified polymers and polymer blends |
EP93907391A EP0630392A1 (en) | 1992-03-10 | 1993-03-10 | Polymers and polymer blends modified with poly(phenylene ether) |
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US85032992A | 1992-03-10 | 1992-03-10 | |
US07/851,371 US5270386A (en) | 1992-03-10 | 1992-03-10 | Styrenic copolymers modified with poly (phenylene ether) |
US07/850,329 | 1992-03-10 | ||
US07/850,324 | 1992-03-10 | ||
US07/850,335 | 1992-03-10 | ||
US07/851,371 | 1992-03-10 | ||
US07/850,324 US5286790A (en) | 1992-03-10 | 1992-03-10 | Acrylate polymers modified with poly(phenylene ether) |
US07/850,335 US5262476A (en) | 1992-03-10 | 1992-03-10 | Polycarbonate/polyester blends modified with poly(phenylene ether) |
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Cited By (5)
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EP0681002A2 (en) * | 1994-05-03 | 1995-11-08 | General Electric Company | Low gloss blends of polycarbonate and graft polymer |
EP0816433A2 (en) * | 1996-07-05 | 1998-01-07 | Daicel Chemical Industries, Ltd. | Thermoplastic polycarbonate composition |
WO2005035660A3 (en) * | 2003-10-10 | 2005-08-18 | Gen Electric | Poly(arylene ether) composition and method of molding |
WO2007073399A1 (en) * | 2005-12-22 | 2007-06-28 | General Electric Company | Low gloss thermoplastic articles |
US8084550B2 (en) | 2005-05-23 | 2011-12-27 | Sabic Innovative Plastics Ip B.V. | Low gloss thermoplastic composition |
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JP2001247751A (en) * | 1999-12-28 | 2001-09-11 | Daicel Chem Ind Ltd | Flame retardant resin composition |
JP5268566B2 (en) * | 2007-11-09 | 2013-08-21 | キヤノン株式会社 | Method for producing thermoplastic resin structure and thermoplastic resin composition |
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US4804700A (en) * | 1985-07-11 | 1989-02-14 | General Electric Company | Resinous compositions |
JPH07736B2 (en) * | 1985-08-02 | 1995-01-11 | ゼネラル・エレクトリック・カンパニイ | Solvent resistant compatible blend of polyphenylene ether and linear polyester |
US4710534A (en) * | 1985-12-09 | 1987-12-01 | General Electric Company | Low gloss, flame reterdant, impact resistant polycarbonate composition |
US4916185A (en) * | 1987-09-09 | 1990-04-10 | Yates Iii John B | Olefinic impact modifiers for compatible blends of polyphenylene ethers and linear polyester resins |
NL8800799A (en) * | 1988-03-30 | 1989-10-16 | Gen Electric | POLYMER MIXTURE WITH AROMATIC POLYCARBONATE, POLYESTER AND FLAME RETARDANT. |
JP2674181B2 (en) * | 1989-02-09 | 1997-11-12 | 住友化学工業株式会社 | Thermoplastic resin composition |
US5196479A (en) * | 1991-02-27 | 1993-03-23 | The Dow Chemical Company | Impact resistant blends of high heat polycarbonate and aromatic polyester |
-
1993
- 1993-03-10 JP JP5516607A patent/JPH07507080A/en active Pending
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Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0681002A2 (en) * | 1994-05-03 | 1995-11-08 | General Electric Company | Low gloss blends of polycarbonate and graft polymer |
EP0681002A3 (en) * | 1994-05-03 | 1996-04-10 | Gen Electric | Low gloss blends of polycarbonate and graft polymer. |
EP0816433A2 (en) * | 1996-07-05 | 1998-01-07 | Daicel Chemical Industries, Ltd. | Thermoplastic polycarbonate composition |
EP0816433A3 (en) * | 1996-07-05 | 1998-08-26 | Daicel Chemical Industries, Ltd. | Thermoplastic polycarbonate composition |
US6066686A (en) * | 1996-07-05 | 2000-05-23 | Daicel Chemical Industries, Ltd. | Polycarbonate compositions |
WO2005035660A3 (en) * | 2003-10-10 | 2005-08-18 | Gen Electric | Poly(arylene ether) composition and method of molding |
US7205342B2 (en) | 2003-10-10 | 2007-04-17 | General Electric Company | Poly(arylene ether) composition and method of molding |
US8084550B2 (en) | 2005-05-23 | 2011-12-27 | Sabic Innovative Plastics Ip B.V. | Low gloss thermoplastic composition |
US8592523B2 (en) | 2005-05-23 | 2013-11-26 | Sabic Innovative Plastics Ip B.V. | Low gloss thermoplastic articles |
WO2007073399A1 (en) * | 2005-12-22 | 2007-06-28 | General Electric Company | Low gloss thermoplastic articles |
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