JPH08231681A - Tackifier - Google Patents
TackifierInfo
- Publication number
- JPH08231681A JPH08231681A JP7038927A JP3892795A JPH08231681A JP H08231681 A JPH08231681 A JP H08231681A JP 7038927 A JP7038927 A JP 7038927A JP 3892795 A JP3892795 A JP 3892795A JP H08231681 A JPH08231681 A JP H08231681A
- Authority
- JP
- Japan
- Prior art keywords
- blocked
- polyisocyanate
- diisocyanate
- acid
- type
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 35
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 229920001944 Plastisol Polymers 0.000 claims abstract description 16
- 239000004999 plastisol Substances 0.000 claims abstract description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 239000002318 adhesion promoter Substances 0.000 claims description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 abstract description 14
- 239000000203 mixture Substances 0.000 abstract description 14
- 239000002981 blocking agent Substances 0.000 abstract description 10
- 239000004014 plasticizer Substances 0.000 abstract description 10
- 229920005989 resin Polymers 0.000 abstract description 8
- 239000011347 resin Substances 0.000 abstract description 8
- 239000003054 catalyst Substances 0.000 abstract description 6
- 229920000642 polymer Polymers 0.000 abstract description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 4
- 238000004383 yellowing Methods 0.000 abstract description 4
- 229910052725 zinc Inorganic materials 0.000 abstract description 4
- 239000011701 zinc Substances 0.000 abstract description 4
- 230000000903 blocking effect Effects 0.000 abstract description 3
- 239000003085 diluting agent Substances 0.000 abstract description 3
- 239000000945 filler Substances 0.000 abstract description 3
- 239000002562 thickening agent Substances 0.000 abstract description 3
- 239000003086 colorant Substances 0.000 abstract description 2
- 239000000470 constituent Substances 0.000 abstract description 2
- 150000003512 tertiary amines Chemical class 0.000 abstract description 2
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 abstract 2
- 125000002524 organometallic group Chemical group 0.000 abstract 1
- -1 hydrogen compound Chemical class 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 125000005442 diisocyanate group Chemical group 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 229920005862 polyol Polymers 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 150000003077 polyols Chemical class 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 5
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 5
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 5
- 229920000768 polyamine Polymers 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- GJYCVCVHRSWLNY-UHFFFAOYSA-N ortho-butylphenol Natural products CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 229920000962 poly(amidoamine) Polymers 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 150000002483 hydrogen compounds Chemical class 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- BYLSIPUARIZAHZ-UHFFFAOYSA-N 2,4,6-tris(1-phenylethyl)phenol Chemical compound C=1C(C(C)C=2C=CC=CC=2)=C(O)C(C(C)C=2C=CC=CC=2)=CC=1C(C)C1=CC=CC=C1 BYLSIPUARIZAHZ-UHFFFAOYSA-N 0.000 description 2
- RRKBRXPIJHVKIC-UHFFFAOYSA-N 2-(2-ethylhexyl)phenol Chemical compound CCCCC(CC)CC1=CC=CC=C1O RRKBRXPIJHVKIC-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 2
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000004070 electrodeposition Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- UMKARVFXJJITLN-UHFFFAOYSA-N lead;phosphorous acid Chemical compound [Pb].OP(O)O UMKARVFXJJITLN-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 125000005498 phthalate group Chemical class 0.000 description 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920005906 polyester polyol Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DDKMFQGAZVMXQV-UHFFFAOYSA-N (3-chloro-2-hydroxypropyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CCl DDKMFQGAZVMXQV-UHFFFAOYSA-N 0.000 description 1
- GCYUJISWSVALJD-UHFFFAOYSA-N 1,1-diethylcyclohexane Chemical compound CCC1(CC)CCCCC1 GCYUJISWSVALJD-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- HYGLETVERPVXOS-UHFFFAOYSA-N 1-bromopyrene Chemical compound C1=C2C(Br)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 HYGLETVERPVXOS-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- XXCVIFJHBFNFBO-UHFFFAOYSA-N 1-ethenoxyoctane Chemical compound CCCCCCCCOC=C XXCVIFJHBFNFBO-UHFFFAOYSA-N 0.000 description 1
- BGUIZQYQWQACDW-ARJAWSKDSA-N 1-o-ethyl 4-o-(2-hydroxyethyl) (z)-but-2-enedioate Chemical compound CCOC(=O)\C=C/C(=O)OCCO BGUIZQYQWQACDW-ARJAWSKDSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- JKTAIYGNOFSMCE-UHFFFAOYSA-N 2,3-di(nonyl)phenol Chemical compound CCCCCCCCCC1=CC=CC(O)=C1CCCCCCCCC JKTAIYGNOFSMCE-UHFFFAOYSA-N 0.000 description 1
- NSENZNPLAVRFMJ-UHFFFAOYSA-N 2,3-dibutylphenol Chemical compound CCCCC1=CC=CC(O)=C1CCCC NSENZNPLAVRFMJ-UHFFFAOYSA-N 0.000 description 1
- IXKVYSRDIVLASR-UHFFFAOYSA-N 2,3-dioctylphenol Chemical compound CCCCCCCCC1=CC=CC(O)=C1CCCCCCCC IXKVYSRDIVLASR-UHFFFAOYSA-N 0.000 description 1
- HRQPPTDGMMGDKC-UHFFFAOYSA-N 2,3-dipropylphenol Chemical compound CCCC1=CC=CC(O)=C1CCC HRQPPTDGMMGDKC-UHFFFAOYSA-N 0.000 description 1
- SKDGWNHUETZZCS-UHFFFAOYSA-N 2,3-ditert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(O)=C1C(C)(C)C SKDGWNHUETZZCS-UHFFFAOYSA-N 0.000 description 1
- FHTGJZOULSYEOB-UHFFFAOYSA-N 2,6-di(butan-2-yl)phenol Chemical compound CCC(C)C1=CC=CC(C(C)CC)=C1O FHTGJZOULSYEOB-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- JZQLRTAGAUZWRH-UHFFFAOYSA-N 2-aminoethanol;hydrate Chemical class [OH-].[NH3+]CCO JZQLRTAGAUZWRH-UHFFFAOYSA-N 0.000 description 1
- ABMULKFGWTYIIK-UHFFFAOYSA-N 2-hexylphenol Chemical compound CCCCCCC1=CC=CC=C1O ABMULKFGWTYIIK-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
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- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 1
- 239000011135 tin Chemical class 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- NQISDOIAJWWPGA-UHFFFAOYSA-N triethyl(3-hydroxypropyl)azanium Chemical compound CC[N+](CC)(CC)CCCO NQISDOIAJWWPGA-UHFFFAOYSA-N 0.000 description 1
- GZBUMTPCIKCWFW-UHFFFAOYSA-N triethylcholine Chemical compound CC[N+](CC)(CC)CCO GZBUMTPCIKCWFW-UHFFFAOYSA-N 0.000 description 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
【0001】[0001]
【産業上の利用分野】本発明はプラスチゾルの接着性付
与剤、更に詳しくは自動車産業等の金属塗装面にプラス
チゾルを強固に接着させるための接着性付与剤に関す
る。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a plastisol adhesiveness imparting agent, and more particularly to an adhesiveness imparting agent for firmly adhering plastisol to a metal coated surface in the automobile industry and the like.
【0002】[0002]
【従来の技術】プラスチゾル例えば塩化ビニル系プラス
チゾルは金属塗装面への接着性を向上させるために接着
性付与剤を添加する方法が用いられている。接着性付与
剤構成成分としては例えばブロックポリイソシアナート
やポリアミドアミン化合物等が使用されている。これら
の技術として、例えば特公昭59−52901号公報で
はポリオール類と有機ジイソシアナートからのイソシア
ナート基を有するウレタンプレポリマーのブロック剤に
よるブロック化ウレタンプレポリマーとポリアミド系化
合物が、特公昭62−41278号公報では平均分子量
が1000〜10000のジイソシアネート重合体の長
鎖アルキルフェノールブロック体が、特開平1−170
633号公報ではポリアミンとイソシアヌレート型ポリ
イソシアナートのブロツク化ウレタンプレポリマーが、
特開平3−29257号公報では2種以上のアルキルフ
ェノールブロック剤でランダムブロツクした芳香族ジイ
ソシアナートの重合体等が開示されている。2. Description of the Related Art For plastisols such as vinyl chloride type plastisols, a method of adding an adhesiveness-imparting agent is used in order to improve the adhesiveness to a metal coated surface. For example, block polyisocyanate, polyamidoamine compound and the like are used as the adhesion imparting agent constituent component. As these techniques, for example, in JP-B-59-52901, a blocked urethane prepolymer with a blocking agent of a urethane prepolymer having an isocyanate group from a polyol and an organic diisocyanate and a polyamide compound are disclosed in JP-B-62-62. In JP 41278, a long chain alkylphenol block of a diisocyanate polymer having an average molecular weight of 1,000 to 10,000 is disclosed in JP-A-1-170.
No. 633 discloses a blocked urethane prepolymer of polyamine and isocyanurate type polyisocyanate,
Japanese Unexamined Patent Publication (Kokai) No. 3-29257 discloses a polymer of aromatic diisocyanate randomly blocked with two or more alkylphenol blocking agents.
【0003】ポリアミドアミン化合物は接着性付与の効
果は優れているものの、耐水性、黄変性性等に課題を有
している。また、ブロックポリイソシアナートは耐水性
等に優れているものの、塩化ビニルの可塑剤との相溶性
が悪く、低温での接着性が劣っていた。Although polyamidoamine compounds are excellent in the effect of imparting adhesiveness, they have problems in water resistance, yellowing resistance and the like. Although the block polyisocyanate is excellent in water resistance and the like, its compatibility with vinyl chloride plasticizers is poor and its adhesion at low temperatures is poor.
【0004】[0004]
【発明が解決しようとする課題】本発明は、耐水性、黄
変性、低温での接着性に優れたプラスチゾルの接着性付
与剤を提供することにある。SUMMARY OF THE INVENTION It is an object of the present invention to provide a plastisol adhesion-imparting agent which is excellent in water resistance, yellowing, and low-temperature adhesion.
【0005】[0005]
【課題を解決するための手段】本発明者らが誠意検討し
た結果、ブロックポリイソシアナートのブロツク剤とし
てアルキルフェノール及びそれ以外のブロック剤を併用
することによりブロックポリイソシアナートの、可塑剤
に対する相溶性が向上することを見いだし本発明を完成
するに至った。Means for Solving the Problems As a result of sincere investigations by the present inventors, the compatibility of a block polyisocyanate with a plasticizer by using an alkylphenol and another blocking agent together as a block agent of the block polyisocyanate Therefore, the present invention has been completed and the present invention has been completed.
【0006】本発明は、イソシアナート基の5以上70
%以下がアルキルフェノール系化合物でブロックされた
ブロックポリイソシアナートを含有することを特徴とす
るプラスチゾルの接着性付与剤であり、ブロックポリイ
ソシアナートは脂肪族及び/または脂環族ジイソシアナ
ートことが好ましい。以下、本発明を詳細に説明する。The present invention has five or more isocyanate groups 70
% Or less is a plastisol adhesiveness-imparting agent characterized by containing a block polyisocyanate blocked with an alkylphenol compound, and the block polyisocyanate is preferably an aliphatic and / or alicyclic diisocyanate. . Hereinafter, the present invention will be described in detail.
【0007】本発明に用いるポリイソシアナートは、例
えばジイソシアナートから得ることができる。芳香族ジ
イソシアナートとしては、トリレンジイソシアナート、
ジフェニルメタンジソイシアナート、ナフチレンジイソ
シアナート、キシリレンジイソシアナート、脂肪族ジイ
ソシアナートとしては、炭素数4〜30のものが、脂環
族ジイソシアナートとしては、炭素数8〜30のものが
好ましく、例えば、1,4−テトラメチレンジイソシア
ナート、1,5−ペンタメチレンジイソシアナート、
1,6−ヘキサメチレンジイソシアナート、2,2,4
(または2,4,4)−トリメチル−1,6−ヘキサメ
チレンジイソシアナート、リジンジイソシアナート、イ
ソホロンジイソシアナート、1,3−ビス(イソシアナ
ートメチル)−シクロヘキサン、4,4’−ジシクロヘ
キシルメタンジイソシアナート、キシリレンジイソシア
ナート、テトラメチルキシレンジイソシアナート等が挙
られる。中でも外観、工業的入手の容易さから、1,6
−ヘキサメチレンジイソシアナート(以下HMDIと称
す)、イソホロンジイソシアナート(以下IPDIと称
す)が好ましい。これらは、単独でも、2種以上混合し
て使用してもよい。The polyisocyanate used in the present invention can be obtained, for example, from diisocyanate. As the aromatic diisocyanate, tolylene diisocyanate,
The diphenylmethane diisocyanate, naphthylene diisocyanate, xylylene diisocyanate, and aliphatic diisocyanate preferably have 4 to 30 carbon atoms, and the alicyclic diisocyanate preferably have 8 to 30 carbon atoms. , For example, 1,4-tetramethylene diisocyanate, 1,5-pentamethylene diisocyanate,
1,6-hexamethylene diisocyanate, 2,2,4
(Or 2,4,4) -trimethyl-1,6-hexamethylene diisocyanate, lysine diisocyanate, isophorone diisocyanate, 1,3-bis (isocyanatomethyl) -cyclohexane, 4,4'-dicyclohexyl Examples include methane diisocyanate, xylylene diisocyanate, and tetramethyl xylene diisocyanate. Among them, 1,6 in terms of appearance and industrial availability
-Hexamethylene diisocyanate (hereinafter referred to as HMDI) and isophorone diisocyanate (hereinafter referred to as IPDI) are preferable. These may be used alone or in combination of two or more.
【0008】これらのジイソシアナートから得られるポ
リイソシアナートとしては、活性水素化合物と反応させ
て得られるウレタン変性ポリイソシアナート、ビウレッ
ト型ポリイソシアナート、イソシアナート基の重合で得
られるイソシアヌレート型ポリイソシアナート等があ
る。これらはジイソシアナートが除去されたポリイソシ
アナートであり、実質的にジイソシアナートを含んでい
ない。Polyisocyanates obtained from these diisocyanates include urethane-modified polyisocyanates obtained by reacting with active hydrogen compounds, biuret-type polyisocyanates, and isocyanurate-type polyisocyanates obtained by polymerization of isocyanate groups. Isocyanate, etc. These are polyisocyanates from which diisocyanate has been removed and are substantially free of diisocyanate.
【0009】ウレタン変性ポリイソシアナートはジイソ
シアナートと分子内に2個以上の活性水素を有する化合
物を反応させて得られる。この様な活性水素を有する化
合物は低分子活性水素量化合物及び高分子量活性水素化
合物がある。低分子量活性水素化合物としては、エチレ
ングリコール、1,2−または1,3−ブロピレングリ
コール、1,3−または1,4−または2,3−ブチレ
ングリコール、1,6−ヘキサンジオール、ネオペンチ
ルグリコール、2−メチル−2,4−ペンタンジオー
ル、2,2,4−トリメチル−1,3−ペンタンジオー
ル、トリメチロールプロパン、グリセリン、、ペンタエ
リトリトールなどがある。The urethane-modified polyisocyanate is obtained by reacting a diisocyanate with a compound having two or more active hydrogens in the molecule. Compounds having such active hydrogen include low molecular weight active hydrogen compounds and high molecular weight active hydrogen compounds. As the low molecular weight active hydrogen compound, ethylene glycol, 1,2- or 1,3-bromopyrene glycol, 1,3- or 1,4- or 2,3-butylene glycol, 1,6-hexanediol, neopentyl Examples include glycol, 2-methyl-2,4-pentanediol, 2,2,4-trimethyl-1,3-pentanediol, trimethylolpropane, glycerin, and pentaerythritol.
【0010】高分子量活性水素化合物としては、脂肪族
炭化水素ポリオール類、ポリエーテルポリオール類、ポ
リエステルポリオール類、エポキシ樹脂類が挙げられ
る。脂肪族炭化水素ポリオール類としては、例えば、末
端水酸基化ポリブタジエンやその水素添加物等が挙げら
れる。またポリエーテルポリオール類としては、例えば
グリセリンやプロピレングリコール等の多価アルコール
の単独または混合物に、エチレンオキサイド、プロピレ
ンオキサイドなどのアルキレンオキサイドの単独または
混合物を付加して得られるポリエーテルポリオール類、
ポリテトラメチレングリコール類、更にアルキレンオキ
サイドにエチレンジアミン、エタノールアミン類などの
多官能化合物を反応させて得られるポリエーテルポリオ
ール類及び、これらポリエーテル類を媒体としてアクリ
ルアミド等を重合して得られる、いわゆるポリマーポリ
オール類等が含まれる。Examples of the high molecular weight active hydrogen compound include aliphatic hydrocarbon polyols, polyether polyols, polyester polyols and epoxy resins. Examples of the aliphatic hydrocarbon polyols include terminal hydroxylated polybutadiene and hydrogenated products thereof. As the polyether polyols, for example, polyether polyols obtained by adding a single or a mixture of polyhydric alcohols such as glycerin and propylene glycol to ethylene oxide, and alkylene oxide such as propylene oxide.
Polytetramethylene glycols, polyether polyols obtained by further reacting alkylene oxide with a polyfunctional compound such as ethylenediamine and ethanolamine, and a so-called polymer obtained by polymerizing acrylamide or the like using these polyethers as a medium Polyols and the like are included.
【0011】ポリエステルポリオール類としては、例え
ばコハク酸、アジピン酸、セバシン酸、ダイマー酸、無
水マレイン酸、無水フタル酸、イソフタル酸、テレフタ
ル酸等のカルボン酸の群から選ばれた二塩基酸の単独ま
たは混合物と、エチレングリコール、プロピレングリコ
ール、ジエチレングリコール、ネオペンチルグリコー
ル、トリメチロールプロパン、グリセリンなどの群から
選ばれた多価アルコールの単独または混合物との縮合反
応によって得られる。As the polyester polyols, for example, a dibasic acid alone selected from the group of carboxylic acids such as succinic acid, adipic acid, sebacic acid, dimer acid, maleic anhydride, phthalic anhydride, isophthalic acid and terephthalic acid. Alternatively, it can be obtained by a condensation reaction of a mixture with a polyhydric alcohol selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, neopentyl glycol, trimethylolpropane, glycerin and the like, alone or in a mixture.
【0012】また、例えばε−カプロラクトンを多価ア
ルコールを用いて開環重合して得られるようなポリカプ
ロラクトン類等が挙げられる。エポキシ樹脂類として
は、ノボラック型、β−メチルエピクロ型、環状オキシ
ラン型、グリシジルエーテル型、グリコールエーテル
型、脂肪族不飽和化合物のエポキシ型、エポキシ化脂肪
酸エステル型、多価カルボン酸エステル型、アミノグリ
シジル型、ハロゲン化型、レゾルシン型等が挙げられ
る。Further, for example, polycaprolactones obtained by ring-opening polymerization of ε-caprolactone using a polyhydric alcohol can be mentioned. Epoxy resins include novolac type, β-methyl epichloro type, cyclic oxirane type, glycidyl ether type, glycol ether type, epoxy type of aliphatic unsaturated compound, epoxidized fatty acid ester type, polycarboxylic acid ester type, aminoglycidyl type. Type, halogenated type, resorcin type and the like.
【0013】イソシアヌレート型ポリイソシアネートを
得るためのイソシアヌレート化反応は触媒が用いられ
る。ここで用いられる触媒は、一般に塩基性を有するも
のが好ましく、例えばテトラメチルアンモニウム、テ
トラエチルアンモニウム等のテトラアルキルアンモニウ
ムのハイドロオキサイドや例えば酢酸、カプリン酸等の
有機弱酸塩、例えばトリメチルヒドロキシプロピルア
ンモニウム、トリメチルヒドロキシエチルアンモニウ
ム、トリエチルヒドロキシプロピルアンモニウム、トリ
エチルヒドロキシエチルアンモニウム等のヒドロキシア
ルキルアンモニウムのハイドロオキサイドや例えば酢
酸、カプリン酸等の有機弱酸塩、アルキルカルボン酸
の例えば錫、亜鉛、鉛等のアルキル金属塩、例えばナ
トリウム、カリウム等の金属アルコラート、ヘキサメ
チルジシラザン等のアミノシリル基含有化合物、マン
ニッヒ塩基類、第二アミン類とエポキシ化合物との併
用、例えばトリブチルホスフィン等の燐系化合物等が
ある。A catalyst is used in the isocyanurate-forming reaction for obtaining an isocyanurate type polyisocyanate. The catalyst used here is generally preferably basic, for example, tetramethylammonium, tetraalkylammonium hydroxide such as tetraethylammonium and organic weak acid salts such as acetic acid and capric acid, such as trimethylhydroxypropylammonium and trimethyl. Hydroxyethylammonium hydroxides such as hydroxyethylammonium, triethylhydroxypropylammonium and triethylhydroxyethylammonium, weak organic acid salts such as acetic acid and capric acid, and alkyl metal salts of alkylcarboxylic acids such as tin, zinc and lead, for example, Metal alcoholates such as sodium and potassium, aminosilyl group-containing compounds such as hexamethyldisilazane, Mannich bases, secondary amines and epoxies Combination with compounds, for example, a phosphorus-based compounds such as tributyl phosphine.
【0014】触媒濃度は、イソシアネート化合物に対し
て10ppm〜1.0%の範囲から選択される。反応は
溶媒を用いても、用いなくてもよい。溶媒を用いる場合
は、イソシアネート基に対して不活性な溶剤を用いるべ
きである。反応温度は通常20〜160℃、好ましくは
40〜130℃である。反応終点は用いる多価アルコー
ルにより異なるが、収率が概ね30%以上となる。The catalyst concentration is selected from the range of 10 ppm to 1.0% based on the isocyanate compound. The reaction may or may not use a solvent. If a solvent is used, it should be inert to the isocyanate groups. The reaction temperature is generally 20 to 160 ° C, preferably 40 to 130 ° C. The reaction end point varies depending on the polyhydric alcohol used, but the yield is about 30% or more.
【0015】反応が目的の収率に達したならば、例え
ば、スルホン酸、燐酸等により触媒を失活させ、反応を
停止する。未反応ジイソシアネートおよび溶剤を除去し
イソシアヌレート構造を有するイソシアヌレート型ポリ
イソシアネートを得ることができる。またイソシアヌレ
ート化反応に先立ちあるいは同時に低分子量活性水素化
合物とジイソシアナートのウレタン化反応を行っても良
い。低分子量活性水素化合物とは前記以外にモノアルコ
ールである例えば炭素数1から13のメタノール、エタ
ノール、ブタノール、ヘプタノール、2−エチルヘキサ
ノール、ノナノール、デカノール、ウンデカノール、ト
リデカノール等がある。When the reaction reaches the target yield, the catalyst is deactivated by, for example, sulfonic acid, phosphoric acid or the like to stop the reaction. Unreacted diisocyanate and solvent can be removed to obtain an isocyanurate type polyisocyanate having an isocyanurate structure. Further, the urethane-forming reaction of the low-molecular weight active hydrogen compound and diisocyanate may be carried out prior to or simultaneously with the isocyanurate-forming reaction. In addition to the above, the low-molecular weight active hydrogen compound includes monoalcohols such as methanol, ethanol, butanol, heptanol, 2-ethylhexanol, nonanol, decanol, undecanol, and tridecanol having 1 to 13 carbon atoms.
【0016】この様にして得られたポリイソシアナート
のイソシアナート基をブロック剤と反応させ、ブロック
ポリイソシアナートが得られる。ブロック剤としては、
アルキルフェノール系、フェノール系、活性メチレン、
メルカプタン系、酸アミド系、酸イミド系、イミダゾー
ル系、尿素系、オキシム系、アミン系、イミド系、ピラ
ゾール系化合物等がある。具体的には、(1)アルキル
フェノール系;炭素原子数4以上のアルキル基を置換基
として有するモノおよびジアルキルフェノール類であっ
て、例えばn−プロピルフェノール、i−プロピルフェ
ノール、n−ブチルフェノール、sec−ブチルフェノ
ール、t−ブチルフェノール、n−ヘキシルフェノー
ル、2−エチルヘキシルフェノール、n−オクチルフェ
ノール、n−ノニルフェノール等のモノアルキルフェノ
ール類、ジ−n−プロピルフェノール、ジイソプロピル
フェノール、イソプロピルクレゾール、ジ−n−ブチル
フェノール、ジ−t−ブチルフェノール、ジ−sec−
ブチルフェノール、ジ−n−オクチルフェノール、ジ−
2−エチルヘキシルフェノール、ジ−n−ノニルフェノ
ール等のジアルキルフェノール類、(2)フェノール
系;フェノール、クレゾール、エチルフェノール、スチ
レン化フェノール、ヒドロキシ安息香酸エステル等、
(3)活性メチレン系;マロン酸ジメチル、マロン酸ジ
エチル、アセト酢酸メチル、アセト酢酸エチル、アセチ
ルアセトン等、(4)メルカプタン系;ブチルメルカプ
タン、ドデシルメルカプタン等、(5)酸アミド系;ア
セトアニリド、酢酸アミド、ε−カプロラクタム、δ−
バレロラクタム、γ−ブチロラクタム等、(6)酸イミ
ド系;コハク酸イミド、マレイン酸イミド等、(7)イ
ミダゾール系;イミダゾール、2−メチルイミダゾール
等、(8)尿素系;尿素、チオ尿素、エチレン尿素等、
(9)オキシム系;ホルムアルドオキシム、アセトアル
ドオキシム、アセトオキシム、メチルエチルケトオキシ
ム、シクロヘキサノンオキシム等、(10)アミン系;
ジフェニルアミン、アニリン、カルバゾール等、(1
1)イミン系;エチレンイミン、ポリエチレンイミン
等、(12)重亜硫酸塩;重亜硫酸ソーダ等、(13)
ピラゾール系;ピラゾール、3−メチルピラゾール、
3,5−ジメチルピラゾール等がある。The isocyanate group of the polyisocyanate thus obtained is reacted with a blocking agent to obtain a blocked polyisocyanate. As a blocking agent,
Alkylphenol type, phenol type, active methylene,
Examples include mercaptan-based, acid amide-based, acid imide-based, imidazole-based, urea-based, oxime-based, amine-based, imide-based, and pyrazole-based compounds. Specifically, (1) alkylphenol-based; mono- and dialkylphenols having an alkyl group having 4 or more carbon atoms as a substituent, such as n-propylphenol, i-propylphenol, n-butylphenol, sec- Monoalkylphenols such as butylphenol, t-butylphenol, n-hexylphenol, 2-ethylhexylphenol, n-octylphenol, n-nonylphenol, di-n-propylphenol, diisopropylphenol, isopropylcresol, di-n-butylphenol, di- t-butylphenol, di-sec-
Butylphenol, di-n-octylphenol, di-
Dialkylphenols such as 2-ethylhexylphenol and di-n-nonylphenol, (2) phenolic compounds; phenol, cresol, ethylphenol, styrenated phenol, hydroxybenzoic acid ester, etc.
(3) Active methylene type; dimethyl malonate, diethyl malonate, methyl acetoacetate, ethyl acetoacetate, acetylacetone, etc. (4) Mercaptan type; butyl mercaptan, dodecyl mercaptan, etc., (5) Acid amide type; acetanilide, acetic amide , Ε-caprolactam, δ-
Valerolactam, γ-butyrolactam, etc., (6) acid imide type; succinimide, maleic acid imide, etc., (7) imidazole type; imidazole, 2-methylimidazole, etc., (8) urea type; urea, thiourea, ethylene Urea, etc.
(9) oxime system; formaldoxime, acetoaldoxime, acetoxime, methylethylketoxime, cyclohexanone oxime, etc. (10) amine system;
Diphenylamine, aniline, carbazole, etc. (1
1) imine type; ethyleneimine, polyethyleneimine, etc., (12) bisulfite; sodium bisulfite, etc., (13)
Pyrazoles; pyrazole, 3-methylpyrazole,
3,5-dimethylpyrazole and the like.
【0017】本発明ではポリイソシアナートのイソシア
ナート基の5%以上70%以下がアルキルフェノール系
化合物でブロックされる。5%未満で有ればブロックポ
リイソシアナートの可塑剤への相溶性が充分でなく、7
0%を越えると低温密着性等アルキルフェノール系化合
物以外のブロック剤でブロックされたブロックポリイソ
シアナートの機能が発揮されない。アルキルフェノール
系化合物でブロックされない残りのイソシアナート基に
対するブロック剤は、前記のアルキルフェノール系以外
の化合物が挙げられるが、フェノール系、オキシム系、
酸アミド系、活性メチレン系が好ましく、特にスチレン
化フェノール、アセトオキシム、メチルエチルケトオキ
シム、ε−カプロラクタム、アセト酢酸エチル、マロン
酸エチルが好ましく、2種以上混合しても良い。In the present invention, not less than 5% and not more than 70% of the isocyanate groups of the polyisocyanate are blocked with the alkylphenol compound. If it is less than 5%, the compatibility of the block polyisocyanate with the plasticizer is insufficient, and 7
If it exceeds 0%, the function of the block polyisocyanate blocked with a blocking agent other than the alkylphenol compound such as low temperature adhesion cannot be exhibited. Examples of the blocking agent for the remaining isocyanate group that is not blocked by the alkylphenol compound include compounds other than the above-mentioned alkylphenol compounds, but phenol compounds, oxime compounds,
Acid amide type and active methylene type are preferable, and styrenated phenol, acetoxime, methyl ethyl ketoxime, ε-caprolactam, ethyl acetoacetate and ethyl malonate are particularly preferable, and two or more kinds may be mixed.
【0018】アルキルフェノール系化合物を必須とする
2種以上のブロック剤のブロック化反応は同時に行って
も良いし、逐次に行っても良い。また、別々にブロック
化を行った後、混合しても良い。ポリイソシアナートと
ブロック剤との反応は溶剤の存在の有無に関わらず行う
ことができる。溶剤を用いる場合、イソシアナート基に
対して不活性な溶剤を用いる必要がある。The blocking reaction of two or more kinds of blocking agents, which essentially requires an alkylphenol compound, may be carried out simultaneously or sequentially. Alternatively, the blocks may be separately formed and then mixed. The reaction between the polyisocyanate and the blocking agent can be carried out with or without the presence of a solvent. When using a solvent, it is necessary to use a solvent which is inactive to the isocyanate group.
【0019】ブロック化反応に際して、錫、亜鉛、鉛等
の有機金属塩及び3級アミン等を触媒として用いてもよ
い。反応は、一般に−20〜150℃で行うことが出来
るが、好ましくは0〜100℃である。100℃以上で
は副反応を起こす可能性があり、他方、あまり低温にな
ると反応速度が小さくなり不利である。In the blocking reaction, an organic metal salt of tin, zinc, lead or the like and a tertiary amine may be used as a catalyst. The reaction can be generally carried out at -20 to 150 ° C, preferably 0 to 100 ° C. If the temperature is 100 ° C. or higher, a side reaction may occur. On the other hand, if the temperature is too low, the reaction rate becomes slow, which is disadvantageous.
【0020】ブロックポリイソシアナートは活性水素含
有アミノ基を有するモノもしくはポリアミドアミン化合
物、ポリアミン等の化合物、ブロックポリイソシアナー
ト反応促進剤と併用できる。前記モノもしくはポリアミ
ド化合物のアミン価は30以上、好ましくは100〜4
50である。アミン価が30未満の場合、相溶性が低下
する。分子量は200〜5000、好ましくは500〜
3000である。The block polyisocyanate can be used in combination with a mono- or polyamidoamine compound having an active hydrogen-containing amino group, a compound such as polyamine, and a block polyisocyanate reaction accelerator. The amine value of the mono- or polyamide compound is 30 or more, preferably 100 to 4
50. If the amine value is less than 30, the compatibility will decrease. The molecular weight is 200-5000, preferably 500-
It is 3000.
【0021】前記ポリアミンとしては、例えば脂肪族、
脂環族ポリアミンであるエチレンジアミン、プロピレン
ジアミン、ジエチレントリアミン、トリエチレンテトラ
ミン、イソホロンジアミン、シクロヘキサンジアミン
等、芳香族ポリアミンであるキシリレンジアミン、トリ
レンジアミン、フェニレンジアミン等がある。前記ブロ
ックポリイソシアナート反応促進剤は例えば、アルカリ
金属化合物として、炭素原子数8〜18の脂肪酸、アル
キル硫酸、アルキルスルホン酸またはこれらのポリオキ
シエチレン付加物のカリウム塩、ナトリウム塩等があ
り、更に鉛白、塩基性ケイ酸鉛、三塩基性硫酸鉛、三塩
基性亜リン酸鉛、シリカゲル共沈ケイ酸鉛、亜鉛華等の
無機金属化合物、炭素数2〜18の脂肪酸とカドミウ
ム、バリウム、カルシウム、亜鉛、鉛、錫、マグネシウ
ム等の金属塩等があり、2種以上併用することもでき
る。Examples of the polyamine include aliphatic compounds,
Alicyclic polyamines such as ethylenediamine, propylenediamine, diethylenetriamine, triethylenetetramine, isophoronediamine, and cyclohexanediamine, and aromatic polyamines such as xylylenediamine, tolylenediamine, and phenylenediamine. Examples of the block polyisocyanate reaction accelerator include, as an alkali metal compound, a fatty acid having 8 to 18 carbon atoms, an alkyl sulfuric acid, an alkyl sulfonic acid, or a potassium salt or sodium salt of a polyoxyethylene adduct thereof, and the like. Inorganic metal compounds such as lead white, basic lead silicate, tribasic lead sulfate, tribasic lead phosphite, silica gel co-precipitated lead silicate, zinc white, fatty acids having 2 to 18 carbon atoms and cadmium, barium, There are metal salts of calcium, zinc, lead, tin, magnesium and the like, and two or more kinds can be used in combination.
【0022】ブロックポリイソシアナートは可塑剤によ
り希釈され接着性付与剤となる。可塑剤としては、塩化
ビニル系重合体に用いられるものであれば特に制限され
るものではなく、例えば、フタル酸ジ−n−ブチル、フ
タル酸ジ−n−オクチル、フタル酸ジ−2−エチルヘキ
シル(以下DOPと称す)、フタル酸ジイソオクチル、
フタル酸ジイソデシル、フタル酸ブチルベンジル、イソ
フタル酸ジ−2−エチルヘキシル等のフタル酸系、アジ
ピン酸ジ−2−エチルヘキシル、アジピン酸−n−デシ
ル、アジピン酸ジイソデシル、アゼライン酸ジ−2−エ
チルヘキシル、セバシン酸ジブチル、セバシン酸ジ−2
−エチルヘキシル等の脂肪酸エステル系、リン酸トリブ
チル、リン酸トリ−2−エチルヘキシル、リン酸−2−
エチルヘキシルジフェニル、リン酸トリクレジル等のリ
ン酸エステル系、エポキシ化大豆油、エポキシ化トール
油脂肪酸−2−エチルヘキシル等のエポキシ系等があ
り、これらの1種または2種以上を混合して使用するこ
とができる。フタル酸系が広く使用されている。The block polyisocyanate is diluted with a plasticizer to serve as an adhesion promoter. The plasticizer is not particularly limited as long as it is used for vinyl chloride polymers, and examples thereof include di-n-butyl phthalate, di-n-octyl phthalate, and di-2-ethylhexyl phthalate. (Hereinafter referred to as DOP), diisooctyl phthalate,
Phthalates such as diisodecyl phthalate, butylbenzyl phthalate and di-2-ethylhexyl isophthalate, di-2-ethylhexyl adipate, n-decyl adipate, diisodecyl adipate, di-2-ethylhexyl azelate, sebacine Acid dibutyl, sebacic acid di-2
-Fatty acid ester such as ethylhexyl, tributyl phosphate, tri-2-ethylhexyl phosphate, phosphoric acid-2-
There are phosphoric ester type such as ethylhexyl diphenyl and tricresyl phosphate, epoxidized soybean oil, epoxy type such as epoxidized tall oil fatty acid-2-ethylhexyl and the like, and one kind or a mixture of two or more kinds of them may be used. You can Phthalates are widely used.
【0023】接着性付与剤中の可塑剤濃度は20〜80
%が好ましい。この様な接着性付与剤は可塑剤に分散さ
れた塩化ビニル系重合体組成物に添加される。塩化ビニ
ル系重合体は、塩化ビニルまたは塩化ビニルとそれに共
重合可能なコモノマーとの混合物とを乳化剤及び水溶性
重合開始剤の存在下に乳化重合して製造される粒径5μ
以下、好ましくは0.05〜3μ程度のベースレジン、
または分散剤及び油溶性重合開始剤の存在下、塩化ビニ
ルまたは塩化ビニルとそれに共重合可能なコモノマーと
の混合物の全量または一部を機械的に微分散した後重合
する微懸濁重合法によって製造されるペーストレジンま
たはペーストレジン混合用のレジンである。また、通常
の懸濁重合によって製造された粒径の大きな塩化ビニー
ル樹脂または塩化ビニル共重合樹脂をペーストゾルの粘
度、流動性、加工性等に悪影響を及ぼさない範囲で併用
しても良い。塩化ビニルに共重合可能なコモノマーとし
ては、例えば酢酸ビニル、プロピオン酸ビニル、ラウリ
ン酸ビニル等のビニルエステル類、メチルアクリレー
ト、エチルアクリレート、ブチルアクリレート、2−ヒ
ドロキシエチルアクリレート、2−ヒドロキシプロピル
アクリレート、3−ヒドロキシブチルアクリレート等の
アクリル酸エステル類、メチルメタクリレート、エチル
メタクリレート、2−ヒドロキシエチルメタクリレー
ト、2−ヒドロキシプロピルメタクリレート、3−クロ
ロ−2−ヒドロキシプロピルメタクリレート等のメタク
リル酸エステル、ジブチルマレエート、ジエチルマレエ
ート、エチル・2−ヒドロキシエチルマレエート等のマ
レイン酸エステル類、ジブチルフマレート、ジエチルフ
マレート等のフマルート酸エステル類、ビニルメチルエ
ーテル、ビニルブチルエーテル、ビニルヒドロキシブチ
ルエーテル、ビニルオクチルエーテル類のビニルエーテ
ル類、アクリロニトリル、メタクリロニトリル等のシア
ン化ビニル類、エチレン、プロピレン、スチレン等のα
−オレフィン類、塩化ビニリデン、臭化ビニル等の塩化
ビニル以外のハロゲン化ビニリデンまたはハロゲン化ビ
ニル類、n−メチロール−アクリルアミドが挙げられ
る。The concentration of the plasticizer in the adhesion-imparting agent is 20-80.
% Is preferred. Such an adhesion promoter is added to the vinyl chloride polymer composition dispersed in the plasticizer. The vinyl chloride-based polymer is produced by emulsion polymerization of vinyl chloride or a mixture of vinyl chloride and a comonomer copolymerizable therewith in the presence of an emulsifier and a water-soluble polymerization initiator.
Below, preferably about 0.05 ~ 3μ base resin,
Alternatively, it is produced by a fine suspension polymerization method in which, in the presence of a dispersant and an oil-soluble polymerization initiator, all or part of vinyl chloride or a mixture of vinyl chloride and a comonomer copolymerizable therewith is mechanically finely dispersed and then polymerized. It is a paste resin or a resin for mixing paste resin. Further, a vinyl chloride resin or a vinyl chloride copolymer resin having a large particle size produced by ordinary suspension polymerization may be used in combination within a range that does not adversely affect the viscosity, fluidity, processability and the like of the paste sol. Examples of comonomers copolymerizable with vinyl chloride include vinyl esters such as vinyl acetate, vinyl propionate and vinyl laurate, methyl acrylate, ethyl acrylate, butyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, and 3 -Acrylic acid esters such as hydroxybutyl acrylate, methacrylic acid esters such as methyl methacrylate, ethyl methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 3-chloro-2-hydroxypropyl methacrylate, dibutyl maleate, diethyl male Maleates such as acrylate and ethyl 2-hydroxyethyl maleate, and fumaric acid esters such as dibutyl fumarate and diethyl fumarate. , Vinyl methyl ether, vinyl butyl ether, vinyl hydroxybutyl ether, vinyl ethers of vinyl octyl ether, acrylonitrile, vinyl cyanides such as methacrylonitrile, ethylene, propylene, styrene and the like α
-Vinylidene halides or vinyl halides other than vinyl chloride such as olefins, vinylidene chloride and vinyl bromide, and n-methylol-acrylamide.
【0024】最終的プラスチゾル組成物は上記成分以外
に、希釈剤、充填剤、増粘剤、着色剤等を添加できる。
希釈剤としては脂肪族系溶剤例えば、ヘキサン、ヘプタ
ン、オクタンねノナン、デカン等、ナフテン系炭化水素
溶剤としてはシクロヘキサン、メチルシクロヘキサン、
ジメチルシクロヘキサン、ジエチルシクロヘキサン等、
芳香族系溶剤としてはトルエン、キシレン、エチルベン
ゼン、ソレベッソ#100(エッソ化学製)、ソルベッ
ソ#150(エッソ化学製)、充填剤としては、例えば
軽質または重質炭酸カルシウム、タルク、ケイソウ土、
カオリン、硫酸バリウム等の無機充填剤、セルロース
粉、粉末ゴム、再生ゴム等の有機系充填剤を挙げること
ができる。増粘剤としては、無水シリカ、有機ベントナ
イト、金属石鹸等が挙げられる。In the final plastisol composition, diluents, fillers, thickeners, colorants and the like can be added in addition to the above components.
Aliphatic solvents such as diluents, such as hexane, heptane, octane-nonane, decane, etc., and naphthene hydrocarbon solvents such as cyclohexane and methylcyclohexane,
Dimethylcyclohexane, diethylcyclohexane, etc.,
As the aromatic solvent, toluene, xylene, ethylbenzene, Soleveso # 100 (manufactured by Esso Chemical), Solvesso # 150 (manufactured by Esso Chemical), and as the filler, for example, light or heavy calcium carbonate, talc, diatomaceous earth,
Examples thereof include inorganic fillers such as kaolin and barium sulfate, and organic fillers such as cellulose powder, powder rubber and recycled rubber. Examples of the thickener include anhydrous silica, organic bentonite, metal soap and the like.
【0025】この様に調整されたプラスチゾル組成物の
塗布量は150〜3000g/m2であり、塗布膜厚は
0.15〜3mmが好ましい。塗布後焼付が行われる。
その場合の温度は110〜150℃、焼付時間は20〜
40分が好ましい。塗装方法は例えば、スプレー塗布、
ハケ塗り、浸漬、注入、流し込み、エアスプレー等の方
法を用いることができる。The coating amount of the plastisol composition thus prepared is 150 to 3000 g / m 2 , and the coating film thickness is preferably 0.15 to 3 mm. Baking is performed after coating.
In that case, the temperature is 110 to 150 ° C., and the baking time is 20 to
40 minutes is preferred. The coating method is, for example, spray coating,
Methods such as brush coating, dipping, pouring, pouring, and air spray can be used.
【0026】本発明の接着性付与剤はプラスチゾル組成
物に添加され、シーリング剤、アンダーコート剤、耐チ
ッピング剤として各種工業用途に応用される。特に自動
車工業においてカチオン電着塗装が施された自動車車体
の上に、防錆、飛び小石等の接触の際の緩衝を目的とし
て、さらにはピンホール、隙間等の目止めを目的とし
て、例えばポリエステル樹脂塗料、エポキシ樹脂塗料、
アクリル樹脂塗料等の下地塗料として利用される。The adhesiveness-imparting agent of the present invention is added to a plastisol composition and applied to various industrial uses as a sealing agent, an undercoating agent and a chipping-resistant agent. Particularly, in the automobile industry, for example, polyester is used on a car body that has been subjected to cationic electrodeposition coating for the purpose of rust prevention, buffering at the time of contact with flying pebbles, and for the purpose of sealing pinholes and gaps. Resin paint, epoxy resin paint,
Used as a base paint for acrylic resin paints.
【0027】[0027]
【実施例】実施例及び比較例中の「部」は重量基準であ
る。プラスチゾルを下記のように調整し、接着性を評価
した。プラスチゾルの組成を「塩化ビニルストレートレ
ジン(鐘淵化学工業の商品名「カネビニルPSL−1
0」)70部、塩化ビニル共重合体(鐘淵化学工業の商
品名「カネビニルPCH−12」)30部、ジオクチル
フタレート110部、炭酸カルシウム150部、2塩基
性亜燐酸鉛3部、ポリアミドアミン(ヘンケル社の商品
名バーサミド140)3部、接着性付与剤3部」とし、
カチオン電着塗装板を被着体として、ゾル厚さ0.5m
m、120℃×30分で焼付後、せん断接着強度を引張
速度5mm/分で測定した。EXAMPLES "Parts" in Examples and Comparative Examples are based on weight. The plastisol was prepared as follows and the adhesiveness was evaluated. The composition of the plastisol is “vinyl chloride straight resin (Kanefuchi Chemical Industry's trade name“ Kanevinyl PSL-1
0 ") 70 parts, vinyl chloride copolymer (Kanefuchi Chemical Industry's trade name" Kanevinyl PCH-12 ") 30 parts, dioctyl phthalate 110 parts, calcium carbonate 150 parts, dibasic lead phosphite 3 parts, polyamidoamine (Henkel brand name Versamide 140) 3 parts, adhesiveness imparting agent 3 parts ",
With a cation electrodeposition coated plate as the adherend, the sol thickness is 0.5 m
m, after baking at 120 ° C. for 30 minutes, the shear adhesive strength was measured at a pulling speed of 5 mm / minute.
【0028】15kg/cm2以上を○、未満を×とし
て評価した。The evaluation was made such that 15 kg / cm 2 or more was evaluated as ◯ and less than 15 kg / cm 2 was evaluated as x.
【0029】[0029]
【実施例1】撹拌機、温度計、還流冷却管を取り付けた
4ツ口フラスコにHMDIを原料としたイソシアヌレー
ト型ポリイソシアナート化合物(旭化成工業(株)の商
品名「デュラネートTPA」)100部をDOP182
部に溶解した後、ノニルフェノール65部を添加し80
℃、2時間保持した。温度を下げ、メチルエチルケトオ
キシム(以下MEKオキシムと称す)25部を40〜5
0℃の範囲で、1時間かけ添加した。赤外スペクトルに
よるイソシアナート基の吸収が消失した事を確認しブロ
ックポリイソシアナートを得た。この溶液を20℃、2
4時間放置後も均一透明溶液であり、相溶性が良好であ
った。この場合の全イソシアナート基に対するノニルフ
ェノールでブロックされたイソシアナート基の割合は5
0%であった。Example 1 100 parts of isocyanurate type polyisocyanate compound (trade name "Duranate TPA" manufactured by Asahi Kasei Co., Ltd.) using HMDI as a raw material in a four-necked flask equipped with a stirrer, a thermometer and a reflux condenser. To DOP182
65 parts of nonylphenol was added to
The temperature was kept at 2 ° C for 2 hours. The temperature is lowered and 25 parts of methyl ethyl ketoxime (hereinafter referred to as MEK oxime) is added to 40 to 5 parts.
In the range of 0 ° C., it was added over 1 hour. It was confirmed by infrared spectrum that the absorption of the isocyanate group had disappeared, and a block polyisocyanate was obtained. This solution at 20 ℃, 2
Even after standing for 4 hours, it was a uniform transparent solution and had good compatibility. In this case, the ratio of nonylphenol-blocked isocyanate groups to the total isocyanate groups is 5
It was 0%.
【0030】[0030]
【実施例2〜3、比較例1〜2】メチルエチルケトオキ
シムとノニルフェノールの添加量を表1とした以外は実
施例1と同様に行った。結果を表1に示す。Examples 2-3, Comparative Examples 1-2 The same procedure as in Example 1 was carried out except that the amounts of methylethylketoxime and nonylphenol added were changed to those shown in Table 1. The results are shown in Table 1.
【0031】[0031]
【表1】 [Table 1]
【0032】[0032]
【発明の効果】それまで限定されたブロックポリイソシ
アナートしか使用できなかったが、本発明はプラスチゾ
ルの可塑剤とブロックポリイソシアナートの相溶性が改
善されたことにより、プラスチゾル組成物の設計が多様
になり、用途に応じ例えば低温焼付での接着性が向上、
黄変の低下等ができる。Although only a limited number of block polyisocyanates can be used so far, the present invention provides a variety of plastisol composition designs due to the improved compatibility of plastisol plasticizers and block polyisocyanates. Depending on the application, for example, the adhesiveness in low temperature baking is improved,
Yellowing can be reduced.
Claims (2)
アルキルフェノール系化合物でブロックされたブロック
ポリイソシアナートを含有することを特徴とするプラス
チゾルの接着性付与剤。1. An adhesiveness-imparting agent for plastisol, characterized in that 5 to 70% of an isocyanate group contains a block polyisocyanate blocked with an alkylphenol compound.
び/または脂環族ジイソシアナートから誘導されること
を特徴とする請求項1記載のプラスチゾルの接着性付与
剤。2. The plastisol adhesion promoter according to claim 1, wherein the block polyisocyanate is derived from an aliphatic and / or alicyclic diisocyanate.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7038927A JPH08231681A (en) | 1995-02-28 | 1995-02-28 | Tackifier |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7038927A JPH08231681A (en) | 1995-02-28 | 1995-02-28 | Tackifier |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH08231681A true JPH08231681A (en) | 1996-09-10 |
Family
ID=12538871
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP7038927A Withdrawn JPH08231681A (en) | 1995-02-28 | 1995-02-28 | Tackifier |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH08231681A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008502774A (en) * | 2004-06-18 | 2008-01-31 | ヘンケル・コマンディットゲゼルシャフト・アウフ・アクチエン | Blocked polyurethane prepolymers useful in coating compositions |
JP2008103756A (en) * | 1996-09-20 | 2008-05-01 | Siemens Ag | Casting material, manufacturing method thereof, and light emitting device |
JP2014076563A (en) * | 2012-10-10 | 2014-05-01 | Hiraoka & Co Ltd | Transparent incombustible sheet |
US9196800B2 (en) | 1996-06-26 | 2015-11-24 | Osram Gmbh | Light-radiating semiconductor component with a luminescence conversion element |
-
1995
- 1995-02-28 JP JP7038927A patent/JPH08231681A/en not_active Withdrawn
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9196800B2 (en) | 1996-06-26 | 2015-11-24 | Osram Gmbh | Light-radiating semiconductor component with a luminescence conversion element |
JP2008103756A (en) * | 1996-09-20 | 2008-05-01 | Siemens Ag | Casting material, manufacturing method thereof, and light emitting device |
JP2009071336A (en) * | 1996-09-20 | 2009-04-02 | Siemens Ag | LED chip |
JP2012238909A (en) * | 1996-09-20 | 2012-12-06 | Osram Ag | Casting material, method of manufacturing the same, and light emitting element |
JP2008502774A (en) * | 2004-06-18 | 2008-01-31 | ヘンケル・コマンディットゲゼルシャフト・アウフ・アクチエン | Blocked polyurethane prepolymers useful in coating compositions |
JP2014076563A (en) * | 2012-10-10 | 2014-05-01 | Hiraoka & Co Ltd | Transparent incombustible sheet |
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Legal Events
Date | Code | Title | Description |
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A300 | Withdrawal of application because of no request for examination |
Free format text: JAPANESE INTERMEDIATE CODE: A300 Effective date: 20020507 |