WO1998039388A1 - Naphtalenedicarboxylate contenant un melange de polyamide/polyester a propriete de retention de saveur amelioree - Google Patents
Naphtalenedicarboxylate contenant un melange de polyamide/polyester a propriete de retention de saveur amelioree Download PDFInfo
- Publication number
- WO1998039388A1 WO1998039388A1 PCT/US1998/004311 US9804311W WO9839388A1 WO 1998039388 A1 WO1998039388 A1 WO 1998039388A1 US 9804311 W US9804311 W US 9804311W WO 9839388 A1 WO9839388 A1 WO 9839388A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- polyamide
- molecular weight
- nylon
- diol
- Prior art date
Links
- 229920002647 polyamide Polymers 0.000 title claims abstract description 57
- 239000004952 Polyamide Substances 0.000 title claims abstract description 55
- 239000000203 mixture Substances 0.000 title claims abstract description 53
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 239000000796 flavoring agent Substances 0.000 title claims abstract description 5
- 235000019634 flavors Nutrition 0.000 title claims abstract description 5
- 229920006149 polyester-amide block copolymer Polymers 0.000 title description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 40
- 229920000728 polyester Polymers 0.000 claims abstract description 30
- 150000002009 diols Chemical class 0.000 claims abstract description 26
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 21
- -1 poly(hexamethylene isophthalamide) Polymers 0.000 claims description 26
- 239000012141 concentrate Substances 0.000 claims description 19
- 229920005989 resin Polymers 0.000 claims description 19
- 239000011347 resin Substances 0.000 claims description 19
- 239000004677 Nylon Substances 0.000 claims description 16
- 229920001778 nylon Polymers 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 229920006012 semi-aromatic polyamide Polymers 0.000 claims description 15
- 239000004953 Aliphatic polyamide Substances 0.000 claims description 14
- 229920003231 aliphatic polyamide Polymers 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 12
- 238000002844 melting Methods 0.000 claims description 9
- 230000008018 melting Effects 0.000 claims description 9
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 8
- 229920002302 Nylon 6,6 Polymers 0.000 claims description 7
- 239000001361 adipic acid Substances 0.000 claims description 6
- 235000011037 adipic acid Nutrition 0.000 claims description 6
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 6
- 229920002292 Nylon 6 Polymers 0.000 claims description 5
- 229920000305 Nylon 6,10 Polymers 0.000 claims description 4
- 239000004760 aramid Substances 0.000 claims description 4
- 229920003235 aromatic polyamide Polymers 0.000 claims description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 4
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 claims description 3
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 claims description 3
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 2
- YQPCHPBGAALCRT-UHFFFAOYSA-N 2-[1-(carboxymethyl)cyclohexyl]acetic acid Chemical compound OC(=O)CC1(CC(O)=O)CCCCC1 YQPCHPBGAALCRT-UHFFFAOYSA-N 0.000 claims description 2
- CPHURRLSZSRQFS-UHFFFAOYSA-N 3-[4-[2-[4-(3-hydroxypropoxy)phenyl]propan-2-yl]phenoxy]propan-1-ol Chemical compound C=1C=C(OCCCO)C=CC=1C(C)(C)C1=CC=C(OCCCO)C=C1 CPHURRLSZSRQFS-UHFFFAOYSA-N 0.000 claims description 2
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 claims description 2
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 claims description 2
- 229920000571 Nylon 11 Polymers 0.000 claims description 2
- 229920000299 Nylon 12 Polymers 0.000 claims description 2
- 229920003189 Nylon 4,6 Polymers 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 229920006131 poly(hexamethylene isophthalamide-co-terephthalamide) Polymers 0.000 claims description 2
- 229920000768 polyamine Polymers 0.000 claims description 2
- 229920006123 polyhexamethylene isophthalamide Polymers 0.000 claims description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 70
- 229920000139 polyethylene terephthalate Polymers 0.000 description 10
- 239000005020 polyethylene terephthalate Substances 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 7
- 239000004609 Impact Modifier Substances 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000001125 extrusion Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000013329 compounding Methods 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- 238000007792 addition Methods 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 239000000026 Pentaerythritol tetranitrate Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229920005601 base polymer Polymers 0.000 description 2
- 235000013361 beverage Nutrition 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- ICPXIRMAMWRMAD-UHFFFAOYSA-N 2-[3-[2-[3-(2-hydroxyethoxy)phenyl]propan-2-yl]phenoxy]ethanol Chemical compound C=1C=CC(OCCO)=CC=1C(C)(C)C1=CC=CC(OCCO)=C1 ICPXIRMAMWRMAD-UHFFFAOYSA-N 0.000 description 1
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- XDOLZJYETYVRKV-UHFFFAOYSA-N 7-Aminoheptanoic acid Chemical compound NCCCCCCC(O)=O XDOLZJYETYVRKV-UHFFFAOYSA-N 0.000 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- 229920000577 Nylon 6/66 Polymers 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- TZYHIGCKINZLPD-UHFFFAOYSA-N azepan-2-one;hexane-1,6-diamine;hexanedioic acid Chemical compound NCCCCCCN.O=C1CCCCCN1.OC(=O)CCCCC(O)=O TZYHIGCKINZLPD-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical class NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- DFFZOPXDTCDZDP-UHFFFAOYSA-N naphthalene-1,5-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1C(O)=O DFFZOPXDTCDZDP-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- DJZKNOVUNYPPEE-UHFFFAOYSA-N tetradecane-1,4,11,14-tetracarboxamide Chemical compound NC(=O)CCCC(C(N)=O)CCCCCCC(C(N)=O)CCCC(N)=O DJZKNOVUNYPPEE-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
Classifications
-
- 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
Definitions
- acetaldehyde acetaldehyde
- AA acetaldehyde
- the container market for carbonated and still mineral water requires exceptionally low levels of acetaldehyde (AA) in the container side wall in order to avoid the diffusion of the AA into the water leading to an undesirable water taste.
- AA is an inherent side product which is generated during the polymerization melt phase and subsequent processing steps.
- variables such as catalyst selection influence the amount of residual AA.
- this level of AA is still perceived to be too high for some applications.
- taste testing has indicated that humans can taste 20 ppb differences in AA. Consequently, there has been significant interest in reducing the residual AA content as low as possible.
- the present invention involves naphthalenedicarboxylate polyester/polyamide blends having surprisingly low AA.
- the present invention further discloses naphthalenedicarboxylate containing polyester/polyamide blends which are formed by mixing a polyester base resin with a concentrate containing the polyamide.
- polyester (A), of the present invention is selected from polyethylene naphthalenedicarboxylate (PEN) or copolyesters thereof.
- the acid component of polyester (A) contains repeat units from at least about 50 mole percent naphthlenedicarboxylic acid and at least about 50 mole percent ethylene glycol, based on 100 mole percent dicarboxylic acid and 100 mole percent diol.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Abstract
La présente invention concerne des compositions à mélange de polyesters présentant des propriétés de rétention de saveur et de couleur améliorées comprenant (A) 98,0 % à 99,95 % en poids d'un polyester constitué (1) d'un composant d'acide dicarboxylique comprenant des unités de répétition d'au moins 50 % en moles d'acide naphtalénedicarboxylique; et (2) un composant de diol comprenant des unités de répétition d'au moins 50 % en moles d'éthylène glycol sur la base de 100 % en moles d'acide dicarboxylique et de 100 % en moles de diol; et (B) 2,0 % à 0,05 % en poids d'un polyamide dans lequel les poids associés de (A) et (B) font un total de 100 %.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP53880698A JP2001514681A (ja) | 1997-03-05 | 1998-03-05 | 風味保持性の改良されたナフタレンジカルボキシレート含有ポリエステル／ポリアミドブレンド |
| EP98908969A EP0964893A1 (fr) | 1997-03-05 | 1998-03-05 | Naphtalenedicarboxylate contenant un melange de polyamide/polyester a propriete de retention de saveur amelioree |
| BR9808301-5A BR9808301A (pt) | 1997-03-05 | 1998-03-05 | Composições de poliéster tendo propriedades melhoradas de retenção de sabor, e, processo para formação de uma mistura |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3600897P | 1997-03-05 | 1997-03-05 | |
| US60/036,008 | 1997-03-05 | ||
| US3398998A | 1998-03-03 | 1998-03-03 | |
| US09/033,989 | 1998-03-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1998039388A1 true WO1998039388A1 (fr) | 1998-09-11 |
Family
ID=26710414
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1998/004311 WO1998039388A1 (fr) | 1997-03-05 | 1998-03-05 | Naphtalenedicarboxylate contenant un melange de polyamide/polyester a propriete de retention de saveur amelioree |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0964893A1 (fr) |
| JP (1) | JP2001514681A (fr) |
| BR (1) | BR9808301A (fr) |
| WO (1) | WO1998039388A1 (fr) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000022043A1 (fr) * | 1998-10-09 | 2000-04-20 | Eastman Chemical Company | Melanges de polyester/polyamide a couleur amelioree |
| WO2001009245A1 (fr) * | 1999-07-30 | 2001-02-08 | Eastman Chemical Company | Melanges de polyester-polyamide caracterises par une faible permeabilite aux gaz et par un trouble limite |
| US6191209B1 (en) * | 1999-06-30 | 2001-02-20 | Ciba Specialty Chemicals Corporation | Polyester compositions of low residual aldehyde content |
| EP1167447A3 (fr) * | 2000-06-28 | 2002-11-20 | SINCO RICERCHE S.p.A. | Mélange maítre de polyarylène-amide pour la préparation de résines polyester |
| WO2004020519A1 (fr) * | 2002-08-30 | 2004-03-11 | The Coca-Cola Company | Polyester a teneur reduite en acetaldehyde et procede mettant en oeuvre un catalyseur d'hydrogenation |
| US6790499B2 (en) | 2000-12-29 | 2004-09-14 | Ciba Speicalty Chemicals Corporation | Polyester compositions of low residual aldehyde content |
| US6908650B2 (en) | 2001-03-02 | 2005-06-21 | Ciba Specialty Chemicals Corporation | Polyester and polyamide compositions of low residual aldehyde content |
| US6916881B2 (en) | 1999-09-27 | 2005-07-12 | Ciba Specialty Chemicals Corporation | Polyester compositions of low residual aldehyde content |
| US7138457B2 (en) | 2001-08-13 | 2006-11-21 | Ciba Specialty Chemicals Corporation | Polyester compositions of low residual aldehyde content |
| WO2007001574A1 (fr) * | 2005-06-17 | 2007-01-04 | Eastman Chemical Company | Procede de preparation d'articles en forme transparents de polyesters comprenant du cyclobutanediol |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA200505735B (en) * | 2003-01-31 | 2006-09-27 | M & G Polimeri Italia Spa | Article comprising light absorbent composition to mask visual haze and related methods |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5340884A (en) * | 1992-04-02 | 1994-08-23 | Eastman Kodak Company | Polyamide concentrate useful for producing blends having improved flavor retaining property and clarity |
| WO1997015629A1 (fr) * | 1995-10-25 | 1997-05-01 | Eastman Chemical Company | Melange de polyester/polyamides ameliore en maintien de saveur et en transparence |
-
1998
- 1998-03-05 EP EP98908969A patent/EP0964893A1/fr not_active Withdrawn
- 1998-03-05 WO PCT/US1998/004311 patent/WO1998039388A1/fr not_active Application Discontinuation
- 1998-03-05 BR BR9808301-5A patent/BR9808301A/pt not_active Application Discontinuation
- 1998-03-05 JP JP53880698A patent/JP2001514681A/ja active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5340884A (en) * | 1992-04-02 | 1994-08-23 | Eastman Kodak Company | Polyamide concentrate useful for producing blends having improved flavor retaining property and clarity |
| WO1997015629A1 (fr) * | 1995-10-25 | 1997-05-01 | Eastman Chemical Company | Melange de polyester/polyamides ameliore en maintien de saveur et en transparence |
Non-Patent Citations (2)
| Title |
|---|
| "POLY(ETHYLENE NAPHTHALENEDICARBOXYLATE)/POLYAMIDE BLENDS", RESEARCH DISCLOSURE, no. 283, November 1987 (1987-11-01), pages 661/662, XP000026955 * |
| "POLY(ETHYLENE NAPHTHALENEDICARBOXYLATE)/POLYAMIDE BLENDS", RESEARCH DISCLOSURE, no. 294, 1 October 1988 (1988-10-01), pages 780 - 784, XP000112386 * |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6239233B1 (en) | 1998-10-09 | 2001-05-29 | Eastman Chemical Company | Polyester/polyamide blends with improved color |
| WO2000022043A1 (fr) * | 1998-10-09 | 2000-04-20 | Eastman Chemical Company | Melanges de polyester/polyamide a couleur amelioree |
| US6191209B1 (en) * | 1999-06-30 | 2001-02-20 | Ciba Specialty Chemicals Corporation | Polyester compositions of low residual aldehyde content |
| WO2001009245A1 (fr) * | 1999-07-30 | 2001-02-08 | Eastman Chemical Company | Melanges de polyester-polyamide caracterises par une faible permeabilite aux gaz et par un trouble limite |
| US6444283B1 (en) | 1999-07-30 | 2002-09-03 | Eastman Chemical Company | Polyester-polyamide blends with reduced gas permeability and low haze |
| US6916881B2 (en) | 1999-09-27 | 2005-07-12 | Ciba Specialty Chemicals Corporation | Polyester compositions of low residual aldehyde content |
| AU777598B2 (en) * | 2000-06-28 | 2004-10-21 | APG Polytech, LLC | Preparation of polyester resins using a masterbatch of polyaryleneamide |
| EP1167447A3 (fr) * | 2000-06-28 | 2002-11-20 | SINCO RICERCHE S.p.A. | Mélange maítre de polyarylène-amide pour la préparation de résines polyester |
| US6630542B2 (en) | 2000-06-28 | 2003-10-07 | Sinco Ricerche S.P.A. | Preparation of polyester resins using a masterbatch of polyaryleneamide |
| US6790499B2 (en) | 2000-12-29 | 2004-09-14 | Ciba Speicalty Chemicals Corporation | Polyester compositions of low residual aldehyde content |
| US6908650B2 (en) | 2001-03-02 | 2005-06-21 | Ciba Specialty Chemicals Corporation | Polyester and polyamide compositions of low residual aldehyde content |
| US7022390B2 (en) | 2001-03-02 | 2006-04-04 | Ciba Specialty Chemicals Corporation | Polyester and polyamide compositions of low residual aldehyde content |
| US7138457B2 (en) | 2001-08-13 | 2006-11-21 | Ciba Specialty Chemicals Corporation | Polyester compositions of low residual aldehyde content |
| WO2004020519A1 (fr) * | 2002-08-30 | 2004-03-11 | The Coca-Cola Company | Polyester a teneur reduite en acetaldehyde et procede mettant en oeuvre un catalyseur d'hydrogenation |
| US7041350B1 (en) | 2002-08-30 | 2006-05-09 | The Coca-Cola Company | Polyester composition and articles with reduced acetaldehyde content and method using hydrogenation catalyst |
| WO2007001574A1 (fr) * | 2005-06-17 | 2007-01-04 | Eastman Chemical Company | Procede de preparation d'articles en forme transparents de polyesters comprenant du cyclobutanediol |
| WO2007001551A1 (fr) * | 2005-06-17 | 2007-01-04 | Eastman Chemical Company | Melanges de polymeres transparents contenant du polyester comprenant un cyclobutanediol, articles produits a partir de ces derniers |
Also Published As
| Publication number | Publication date |
|---|---|
| BR9808301A (pt) | 2000-05-16 |
| JP2001514681A (ja) | 2001-09-11 |
| EP0964893A1 (fr) | 1999-12-22 |
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