JPH04255780A - Resin composition for tacky agent - Google Patents
Resin composition for tacky agentInfo
- Publication number
- JPH04255780A JPH04255780A JP3802291A JP3802291A JPH04255780A JP H04255780 A JPH04255780 A JP H04255780A JP 3802291 A JP3802291 A JP 3802291A JP 3802291 A JP3802291 A JP 3802291A JP H04255780 A JPH04255780 A JP H04255780A
- Authority
- JP
- Japan
- Prior art keywords
- tacky
- resin composition
- group
- meth
- anhydride
- 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.)
- Pending
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 22
- -1 cyclic acid anhydride Chemical class 0.000 claims abstract description 39
- 229920000728 polyester Polymers 0.000 claims abstract description 19
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 14
- 150000002118 epoxides Chemical class 0.000 claims abstract description 13
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 11
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 11
- 239000006087 Silane Coupling Agent Substances 0.000 claims abstract description 7
- 230000001070 adhesive effect Effects 0.000 claims description 35
- 239000000853 adhesive Substances 0.000 claims description 29
- 229910010272 inorganic material Inorganic materials 0.000 abstract description 9
- 239000011147 inorganic material Substances 0.000 abstract description 9
- 239000011256 inorganic filler Substances 0.000 abstract description 6
- 229910003475 inorganic filler Inorganic materials 0.000 abstract description 6
- 239000012784 inorganic fiber Substances 0.000 abstract description 5
- 238000002156 mixing Methods 0.000 abstract description 5
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 20
- 239000000203 mixture Substances 0.000 description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 125000000524 functional group Chemical group 0.000 description 11
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 7
- 229920006223 adhesive resin Polymers 0.000 description 7
- 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 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000000123 paper Substances 0.000 description 6
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 125000001302 tertiary amino group Chemical group 0.000 description 4
- 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 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZPQAUEDTKNBRNG-UHFFFAOYSA-N 2-methylprop-2-enoylsilicon Chemical compound CC(=C)C([Si])=O ZPQAUEDTKNBRNG-UHFFFAOYSA-N 0.000 description 3
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000002560 nitrile group Chemical group 0.000 description 3
- 239000004745 nonwoven fabric Substances 0.000 description 3
- 239000002985 plastic film Substances 0.000 description 3
- 229920006255 plastic film Polymers 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 3
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- 229920000298 Cellophane Polymers 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical group OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 125000004018 acid anhydride group Chemical group 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000004840 adhesive resin Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 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 2
- 239000000919 ceramic Substances 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 2
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- LTVUCOSIZFEASK-MPXCPUAZSA-N (3ar,4s,7r,7as)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methano-2-benzofuran-1,3-dione Chemical compound C([C@H]1C=C2)[C@H]2[C@H]2[C@]1(C)C(=O)OC2=O LTVUCOSIZFEASK-MPXCPUAZSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- AFENDNXGAFYKQO-VKHMYHEASA-N (S)-2-hydroxybutyric acid Chemical compound CC[C@H](O)C(O)=O AFENDNXGAFYKQO-VKHMYHEASA-N 0.000 description 1
- KYPOHTVBFVELTG-OWOJBTEDSA-N (e)-but-2-enedinitrile Chemical compound N#C\C=C\C#N KYPOHTVBFVELTG-OWOJBTEDSA-N 0.000 description 1
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 1
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 1
- 150000000190 1,4-diols Chemical class 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 1
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 1
- LZMNXXQIQIHFGC-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C(C)=C LZMNXXQIQIHFGC-UHFFFAOYSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- BJEMXPVDXFSROA-UHFFFAOYSA-N 3-butylbenzene-1,2-diol Chemical compound CCCCC1=CC=CC(O)=C1O BJEMXPVDXFSROA-UHFFFAOYSA-N 0.000 description 1
- RDFQSFOGKVZWKF-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O RDFQSFOGKVZWKF-UHFFFAOYSA-N 0.000 description 1
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 1
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 1
- KNDQHSIWLOJIGP-UHFFFAOYSA-N 826-62-0 Chemical compound C1C2C3C(=O)OC(=O)C3C1C=C2 KNDQHSIWLOJIGP-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- XSDCTSITJJJDPY-UHFFFAOYSA-N chloro-ethenyl-dimethylsilane Chemical compound C[Si](C)(Cl)C=C XSDCTSITJJJDPY-UHFFFAOYSA-N 0.000 description 1
- PLMTWHZZBPGADP-UHFFFAOYSA-N chloro-ethenyl-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C=C)(Cl)C1=CC=CC=C1 PLMTWHZZBPGADP-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- NKKMVIVFRUYPLQ-NSCUHMNNSA-N crotononitrile Chemical compound C\C=C\C#N NKKMVIVFRUYPLQ-NSCUHMNNSA-N 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- STZIXLPVKZUAMV-UHFFFAOYSA-N cyclopentane-1,1,2,2-tetracarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC1(C(O)=O)C(O)=O STZIXLPVKZUAMV-UHFFFAOYSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- MAYIDWCWWMOISO-UHFFFAOYSA-N dichloro-bis(ethenyl)silane Chemical compound C=C[Si](Cl)(Cl)C=C MAYIDWCWWMOISO-UHFFFAOYSA-N 0.000 description 1
- YCEQUKAYVABWTE-UHFFFAOYSA-N dichloro-methyl-prop-2-enylsilane Chemical compound C[Si](Cl)(Cl)CC=C YCEQUKAYVABWTE-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- WHGNXNCOTZPEEK-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)CCCOCC1CO1 WHGNXNCOTZPEEK-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- WCASXYBKJHWFMY-UHFFFAOYSA-N gamma-methylallyl alcohol Natural products CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FLBJFXNAEMSXGL-UHFFFAOYSA-N het anhydride Chemical compound O=C1OC(=O)C2C1C1(Cl)C(Cl)=C(Cl)C2(Cl)C1(Cl)Cl FLBJFXNAEMSXGL-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 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 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- AYLRODJJLADBOB-QMMMGPOBSA-N methyl (2s)-2,6-diisocyanatohexanoate Chemical compound COC(=O)[C@@H](N=C=O)CCCCN=C=O AYLRODJJLADBOB-QMMMGPOBSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- AWGZKFQMWZYCHF-UHFFFAOYSA-N n-octylprop-2-enamide Chemical compound CCCCCCCCNC(=O)C=C AWGZKFQMWZYCHF-UHFFFAOYSA-N 0.000 description 1
- XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- JUVGLPRIQOJMIR-UHFFFAOYSA-N oxiran-2-ylmethyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OCC1CO1 JUVGLPRIQOJMIR-UHFFFAOYSA-N 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- YQUVCSBJEUQKSH-UHFFFAOYSA-N protochatechuic acid Natural products OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical compound S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- JEEPFAKTJAOOQX-UHFFFAOYSA-N trichloro-(4-ethenylphenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=C(C=C)C=C1 JEEPFAKTJAOOQX-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 description 1
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
【0001】0001
【産業上の利用分野】本発明は,粘着力,凝集力などの
粘着特性に非常に優れ,無機材料への接着性が良好で,
無機フィラーや無機繊維との混和性にも優れた粘着剤用
樹脂組成物に関する。[Industrial Application Field] The present invention has excellent adhesive properties such as adhesive force and cohesive force, and has good adhesion to inorganic materials.
The present invention relates to a resin composition for adhesives that has excellent miscibility with inorganic fillers and inorganic fibers.
【0002】0002
【従来の技術】従来から一般的に用いられているアクリ
ル系粘着剤は,ブチルアクリレート,2−エチルヘキシ
ルアクリレートなどの,ポリマーにおけるガラス転移温
度が室温以下であるアクリル酸またはメタクリル酸のア
ルキルエステルを主要なモノマーとし,凝集力や粘着力
を高めるために,酢酸ビニル,アクリロニトリルなどの
ポリマーのガラス転移温度を上昇させるモノマーや,水
酸基,カルボキシル基,アミド基などの官能基を有する
モノマーを共重合させたポリマーを主成分としている。[Prior Art] Acrylic adhesives that have been commonly used in the past are mainly made of alkyl esters of acrylic acid or methacrylic acid, such as butyl acrylate and 2-ethylhexyl acrylate, whose glass transition temperature is below room temperature. In order to increase cohesion and adhesive strength, we copolymerized monomers that raise the glass transition temperature of polymers, such as vinyl acetate and acrylonitrile, and monomers that have functional groups such as hydroxyl, carboxyl, and amide groups. The main component is polymer.
【0003】しかし,ポリマーのみでは凝集力と粘着力
のバランスをとったり,耐熱性を持たせたりすることが
難しく,実際の粘着剤では,フェノール樹脂,ロジン樹
脂,石油系樹脂や,これらの変性樹脂である粘着付与剤
を添加したり,ポリイソシアネートなどの架橋剤とアク
リルポリマー中の官能基との反応によって,凝集力を向
上させている。[0003] However, it is difficult to balance cohesive force and adhesive force or to provide heat resistance using only polymers, and in actual adhesives, phenolic resins, rosin resins, petroleum resins, or modified resins of these are used. The cohesive force is improved by adding a tackifier such as polyisocyanate or by reacting a crosslinking agent such as polyisocyanate with a functional group in the acrylic polymer.
【0004】そこで,前発明(特願平02−26918
5)により,粘着力,凝集力などの粘着特性に優れた樹
脂組成物を開発したが,セラミック,ガラス,金属など
無機材料への接着性が良好ではなく,無機フィラーや無
機繊維との混和性も不十分であった。[0004] Therefore, the previous invention (Japanese Patent Application No. 02-26918)
5), we have developed a resin composition with excellent adhesive properties such as adhesive strength and cohesive strength, but it does not have good adhesion to inorganic materials such as ceramics, glass, and metals, and has poor compatibility with inorganic fillers and inorganic fibers. was also insufficient.
【0005】[0005]
【発明が解決しようとする課題】 本発明は,従来の
粘着剤用樹脂組成物における上記のような問題点,即ち
無機材料への適性が悪いという欠点をシランカップリン
グ剤の添加によって改良し,粘着力,凝集力などの粘着
特性に非常に優れ,無機材料への接着性が良好で,無機
フィラーや無機繊維との混和性にも優れた粘着剤用樹脂
組成物を提供するものである。[Problems to be Solved by the Invention] The present invention improves the above-mentioned problems of conventional resin compositions for pressure-sensitive adhesives, namely their poor suitability for inorganic materials, by adding a silane coupling agent. The present invention provides a resin composition for pressure-sensitive adhesives that has excellent adhesive properties such as adhesive force and cohesive force, has good adhesion to inorganic materials, and has excellent miscibility with inorganic fillers and inorganic fibers.
【0006】[0006]
【課題を解決するための手段】 本発明は,環状酸無
水物(a)およびエポキシド(b)を主原料として得ら
れるポリエステルオリゴマー(A),粘着性アクリルポ
リマー(B),ポリイソシアネート(C),シランカッ
プリング剤(D)を含むことを特徴とする粘着剤用樹脂
組成物である。[Means for Solving the Problems] The present invention provides a polyester oligomer (A), a sticky acrylic polymer (B), and a polyisocyanate (C) obtained using a cyclic acid anhydride (a) and an epoxide (b) as main raw materials. , a silane coupling agent (D).
【0007】本発明においてポリエステルオリゴマー(
A)を得る際には,初期反応の円滑な進行と生成するポ
リエステルオリゴマー(A)の分子量の調整のために,
水酸基または一級,二級,三級アミノ基など,反応の起
点となる官能基を有する化合物を用いる必要がある。こ
の中でも,原料および生成物の性状や反応時の管理のし
やすさなどから,一般的には水酸基を有する化合物を用
いるのが好ましい。[0007] In the present invention, polyester oligomer (
When obtaining A), in order to smooth the initial reaction and adjust the molecular weight of the polyester oligomer (A) to be produced,
It is necessary to use a compound that has a functional group that serves as a starting point for the reaction, such as a hydroxyl group or a primary, secondary, or tertiary amino group. Among these, it is generally preferable to use a compound having a hydroxyl group in view of the properties of the raw materials and products and ease of control during the reaction.
【0008】水酸基を有する化合物としてはメタノール
,エタノール,1−プロパノール,2−プロパノール,
1−ブタノール,2−ブタノール,ペンタノール,ヘキ
サノールなどの脂肪族飽和アルコール,アリルアルコー
ル,クロチルアルコール,プロパギルアルコールなどの
脂肪族不飽和アルコール,2−ヒドロキシエチル(メタ
)アクリレート,2−ヒドロキシプロピル(メタ)アク
リレート,3−ヒドロキシプロピル(メタ)アクリレー
ト,4−ヒドロキシブチル(メタ)アクリレート,N−
メチロールアクリルアミドなどの水酸基を有する(メタ
)アクリレートまたは(メタ)アクリルアミドなど,シ
クロペンタノール,シクロヘキサノールなどの脂環式ア
ルコール,ベンジルアルコール,シンナミルアルコール
などの芳香族アルコール,フルフリルアルコール,テト
ラヒドロフルフリルアルコールなどの複素環アルコール
,エチレングリコール,プロピレングリコール,1,4
−ブチレングリコール,ブテンジオール,ヘキサンジオ
ール,シクロヘキサンジオール,ビスフェノールA,ジ
エチレングリコールなどのジオール,グリセリン,トリ
メチロールプロパンなどのトリオール,フェノール,o
−クレゾール,m−クレゾール,p−クレゾールなどの
フェノール類などのアルコール性またはフェノール性の
水酸基を有する化合物であればよい。Compounds having hydroxyl groups include methanol, ethanol, 1-propanol, 2-propanol,
Aliphatic saturated alcohols such as 1-butanol, 2-butanol, pentanol, hexanol, aliphatic unsaturated alcohols such as allyl alcohol, crotyl alcohol, propargyl alcohol, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, N-
(meth)acrylates with hydroxyl groups such as methylol acrylamide or (meth)acrylamide; alicyclic alcohols such as cyclopentanol and cyclohexanol; aromatic alcohols such as benzyl alcohol and cinnamyl alcohol; furfuryl alcohol and tetrahydrofurfuryl. Heterocyclic alcohols such as alcohol, ethylene glycol, propylene glycol, 1,4
- Diols such as butylene glycol, butenediol, hexanediol, cyclohexanediol, bisphenol A, diethylene glycol, triols such as glycerin, trimethylolpropane, phenol, o
- Any compound having an alcoholic or phenolic hydroxyl group such as phenols such as -cresol, m-cresol, and p-cresol may be used.
【0009】しかしこの中でも,前出のジオールや,2
−ヒドロキシ−n−酪酸,3−ヒドロキシ−n−酪酸,
p−ヒドロキシ安息香酸,ヒドロキシピバリン酸,サリ
チル酸,バニリン酸,12−ヒドロキシステアリン酸な
どのカルボキシル基と水酸基を同時に有する化合物,あ
るいはエタノールアミン,1−アミノ−2−プロパノー
ル,o−アミノフェノール,m−アミノフェノール,p
−アミノフェノールなどのアミノ基と水酸基を同時に有
する化合物など,2つ以上の官能基を有する化合物が好
ましい。However, among these, the above-mentioned diol and 2
-Hydroxy-n-butyric acid, 3-hydroxy-n-butyric acid,
Compounds having both a carboxyl group and a hydroxyl group such as p-hydroxybenzoic acid, hydroxypivalic acid, salicylic acid, vanillic acid, 12-hydroxystearic acid, or ethanolamine, 1-amino-2-propanol, o-aminophenol, m- aminophenol, p
Compounds having two or more functional groups, such as compounds having both an amino group and a hydroxyl group such as -aminophenol, are preferred.
【0010】本発明において環状酸無水物(a)として
は多価カルボン酸の分子内無水物であり,飽和または不
飽和の脂肪族多価カルボン酸無水物,脂環式多価カルボ
ン酸無水物,芳香族多価カルボン酸無水物など,あるい
はこれらの一部が飽和または不飽和の炭化水素基,芳香
環基,ハロゲン原子,複素環基などで置換されたものが
あり,これらの具体例としては,無水こはく酸,無水フ
タル酸,無水マレイン酸,無水イタコン酸,無水グルタ
ル酸,無水ドデセニルこはく酸,無水クロレンデック酸
,無水ピロメリット酸,無水トリメリット酸,シクロペ
ンタンテトラカルボン酸二無水物,ヘキサヒドロ無水フ
タル酸,メチルヘキサヒドロ無水フタル酸,テトラメチ
レン無水マレイン酸,テトラヒドロ無水フタル酸,メチ
ルテトラヒドロ無水フタル酸,エンドメチレンテトラヒ
ドロ無水フタル酸,メチルエンドメチレンテトラヒドロ
無水フタル酸,5−(2,5−ジオキソテトラヒドロキ
シフリル)−3−メチル−3−シクロヘキセン−1,2
−ジカルボン酸無水物,無水メチルナジック酸,無水ベ
ンゾフェノンテトラカルボン酸,グリセロールトリス(
アンヒドロトリメリテート),エチレングリコールビス
(アンヒドロトリメリテート)などがある。これらの中
でも,架橋構造を作らないジカルボン酸またはトリカル
ボン酸の無水物を用いることが好ましい。[0010] In the present invention, the cyclic acid anhydride (a) is an intramolecular anhydride of a polycarboxylic acid, such as a saturated or unsaturated aliphatic polycarboxylic acid anhydride, an alicyclic polycarboxylic acid anhydride. , aromatic polyhydric carboxylic acid anhydrides, etc., or those in which a part of these is substituted with a saturated or unsaturated hydrocarbon group, an aromatic ring group, a halogen atom, a heterocyclic group, etc. Specific examples of these include: are succinic anhydride, phthalic anhydride, maleic anhydride, itaconic anhydride, glutaric anhydride, dodecenylsuccinic anhydride, chlorendic anhydride, pyromellitic anhydride, trimellitic anhydride, cyclopentanetetracarboxylic dianhydride, Hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, tetramethylene maleic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, endomethylenetetrahydrophthalic anhydride, methylendomethylenetetrahydrophthalic anhydride, 5-(2,5 -dioxotetrahydroxyfuryl)-3-methyl-3-cyclohexene-1,2
-Dicarboxylic anhydride, methylnadic anhydride, benzophenonetetracarboxylic anhydride, glycerol tris (
These include ethylene glycol bis(anhydrotrimellitate) and ethylene glycol bis(anhydrotrimellitate). Among these, it is preferable to use dicarboxylic acid or tricarboxylic acid anhydrides that do not form a crosslinked structure.
【0011】本発明において,エポキシド(b)として
は,エピクロルヒドリン,フェニルグリシジルエーテル
,スチレンオキサイド,シクロヘキセンオキサイド,ブ
テンオキサイド,グリシジル(メタ)アクリレート,グ
リシジルシンナメート,アリルグリシジルエーテル,ビ
ニルシクロヘキセンモノエポキサイド,1,3−ブタジ
エンモノエポキサイドなどがあり,これらは飽和もしく
は不飽和の炭化水素基,芳香環基,ハロゲン原子,複素
環基などで置換されていてもよい。In the present invention, the epoxide (b) includes epichlorohydrin, phenylglycidyl ether, styrene oxide, cyclohexene oxide, butene oxide, glycidyl (meth)acrylate, glycidyl cinnamate, allyl glycidyl ether, vinylcyclohexene monoepoxide, 1, Examples include 3-butadiene monoepoxide, which may be substituted with saturated or unsaturated hydrocarbon groups, aromatic ring groups, halogen atoms, heterocyclic groups, etc.
【0012】上記水酸基を有する化合物,環状酸無水物
(a)およびエポキシド(b)の中のそれぞれ1種また
は2種以上を反応させて,ポリエステルオリゴマー(A
)が得られる。反応は,適当な溶媒の存在下あるいは不
存在下,N,N−ジメチルベンジルアミン,トリエチル
アミン,トリブチルアミン,N,N−ジエチルアニリン
,N,N−ジメチルアニリンなどの三級アミンなどを必
要に応じて触媒として用い,エチレン性不飽和基を持つ
化合物を用いる場合には,その保護のために,ハイドロ
キノン,ハイドロキノンモノメチルエーテル,tert
−ブチルカテコール,p−ベンゾキノンなどのラジカル
重合禁止剤を添加した状態で行なうことができる。[0012] Polyester oligomer (A
) is obtained. The reaction is carried out in the presence or absence of a suitable solvent using a tertiary amine such as N,N-dimethylbenzylamine, triethylamine, tributylamine, N,N-diethylaniline, N,N-dimethylaniline, etc. as necessary. When a compound with an ethylenically unsaturated group is used as a catalyst, hydroquinone, hydroquinone monomethyl ether, tert.
-It can be carried out in a state in which a radical polymerization inhibitor such as butylcatechol or p-benzoquinone is added.
【0013】反応は,水酸基を有する化合物の水酸基と
,環状酸無水物(a)の酸無水物基とが先ず優先的に反
応し,次いで,この反応により生じたカルボキシル基と
エポキシド(b)のエポキシ基とが反応し,二級の水酸
基を生じる。さらに,生じた水酸基と環状酸無水物(a
)の酸無水物基とが反応するというように,以下,順次
,上記と同様の反応を進行させることができる。In the reaction, the hydroxyl group of the compound having a hydroxyl group and the acid anhydride group of the cyclic acid anhydride (a) first react preferentially, and then the carboxyl group produced by this reaction reacts with the epoxide (b). Reacts with epoxy groups to produce secondary hydroxyl groups. Furthermore, the resulting hydroxyl group and cyclic acid anhydride (a
) can be reacted with the acid anhydride group, and the same reactions as above can proceed in sequence.
【0014】この反応において,水酸基を有する化合物
の量に対して反応させられる環状酸無水物(a)および
エポキシド(b)の量を調整することにより,水酸基を
有する化合物を末端とする,所望の長さのポリエステル
オリゴマー(A)をつくることができるIn this reaction, by adjusting the amounts of the cyclic acid anhydride (a) and epoxide (b) to be reacted with respect to the amount of the compound having a hydroxyl group, the desired compound having a hydroxyl group as a terminal can be obtained. Polyester oligomers (A) of length can be made.
【0015】そ
れぞれの化合物の割合は,環状酸無水物(a)がジカル
ボン酸無水物である場合には, 水酸基を有する化合物
1モルに対して環状酸無水物(a)1〜20モル,およ
びエポキシド(b)1〜20モルの割合で,また,環状
酸無水物(a)とエポキシド(b)とはほぼ等モルの割
合で反応させることが好ましい。環状酸無水物(a)が
トリカルボン酸である場合には,水酸基を有する化合物
1モルに対して環状酸無水物(a)1〜10モルおよび
エポキシド(b)1〜20モルの割合で,また,環状酸
無水物(a)1モルに対してエポキシド(b)をほぼ1
〜2モルの割合で反応させることが好ましい。[0015] When the cyclic acid anhydride (a) is a dicarboxylic acid anhydride, the ratio of each compound is 1 to 20 mol of the cyclic acid anhydride (a) to 1 mol of the compound having a hydroxyl group, and It is preferable that the epoxide (b) is reacted in a proportion of 1 to 20 moles, and the cyclic acid anhydride (a) and the epoxide (b) are reacted in a substantially equimolar proportion. When the cyclic acid anhydride (a) is a tricarboxylic acid, the ratio of 1 to 10 moles of the cyclic acid anhydride (a) and 1 to 20 moles of the epoxide (b) per 1 mole of the compound having a hydroxyl group; , approximately 1 mol of epoxide (b) to 1 mol of cyclic acid anhydride (a)
It is preferable to react at a ratio of ~2 moles.
【0016】水酸基を有する化合物1モルに対して反応
させられる環状酸無水物(a)またはエポキシド(b)
の量が1モル未満の場合には,得られるポリエステルオ
リゴマー(A)の分子量が低かったり,水酸基を有する
化合物の残留があって,必要な特性が得られない。逆に
,環状酸無水物(a)またはエポキシド(b)の量が2
0モルを超える場合には,反応のコントロールが難しく
なったり,分子量が高くなりすぎて,やはり必要な特性
が得られなくなる傾向がある。Cyclic acid anhydride (a) or epoxide (b) reacted with 1 mole of a compound having a hydroxyl group
If the amount is less than 1 mol, the resulting polyester oligomer (A) may have a low molecular weight or a compound having a hydroxyl group may remain, making it impossible to obtain the necessary properties. Conversely, if the amount of cyclic acid anhydride (a) or epoxide (b) is 2
If the amount exceeds 0 mol, it becomes difficult to control the reaction or the molecular weight becomes too high, making it difficult to obtain the necessary properties.
【0017】ここで得られるポリエステルオリゴマー(
A)は前記のように,水酸基を有する化合物,環状酸無
水物(a),エポキシド(b)についてそれぞれ多種の
化合物を原料として用いることができる上に,その割合
を変えることで比較的分子量の揃った任意の長さのもの
をつくることができる。また,それぞれの化合物につい
て2種以上のものを混ぜて用いることも可能である。
このため,使用する目的に応じて多種多様の特性をもつ
オリゴマーをつくることができる。よって,粘着剤に添
加する場合には,粘着付与剤として働くものから,充填
剤的な作用をするものまで,用途によってオリゴマーの
種類とその配合比を変えることにより,必要な特性を組
成物に与えることが可能である。The polyester oligomer obtained here (
As mentioned above, for A), a wide variety of compounds can be used as raw materials for compounds having hydroxyl groups, cyclic acid anhydrides (a), and epoxides (b), and by changing their proportions, it is possible to obtain compounds with relatively low molecular weights. You can make any length you want. Moreover, it is also possible to use a mixture of two or more types of each compound. Therefore, oligomers with a wide variety of properties can be created depending on the purpose of use. Therefore, when adding oligomers to adhesives, the desired properties can be imparted to the composition by changing the type of oligomer and its blending ratio depending on the application, ranging from those that act as tackifiers to those that act like fillers. It is possible to give.
【0018】本発明において,粘着性アクリルポリマー
(B)とは水酸基,三級アミノ基,カルボキシル基,ア
ミド基,N−置換アミド基,ニトリル基などの官能基を
有するものであり,一般に粘着剤用アクリル樹脂として
用いられているものである。また,ポリマー単独では粘
着性に劣っていても,ポリエステルオリゴマー(A)や
その他の樹脂を加えることにより,良好な粘着特性を示
すようなポリマーは本発明のポリマー(B)として用い
ることができる。これらの官能基を有するアクリルポリ
マーは,水酸基,三級アミノ基,カルボキシル基,アミ
ド基,N−置換アミド基,ニトリル基などを有するモノ
マーのうちの1種以上,好ましくは2種以上と,アルキ
ル(メタ)アクリレート,酢酸ビニル,プロピオン酸ビ
ニル,ビニルエーテル,スチレンなどのモノマーとの共
重合体などである。In the present invention, the adhesive acrylic polymer (B) is one having functional groups such as a hydroxyl group, a tertiary amino group, a carboxyl group, an amide group, an N-substituted amide group, and a nitrile group, and is generally used as an adhesive. It is used as an acrylic resin. Further, even if the polymer alone has poor adhesiveness, a polymer that exhibits good adhesive properties by adding polyester oligomer (A) or other resin can be used as the polymer (B) of the present invention. Acrylic polymers having these functional groups are composed of one or more, preferably two or more, monomers having a hydroxyl group, a tertiary amino group, a carboxyl group, an amide group, an N-substituted amide group, a nitrile group, etc., and an alkyl group. These include copolymers with monomers such as (meth)acrylate, vinyl acetate, vinyl propionate, vinyl ether, and styrene.
【0019】水酸基を有するモノマーとしては,2−ヒ
ドロキシエチル(メタ)アクリレート,2−ヒドロキシ
プロピル(メタ)アクリレート,3−ヒドロキシプロピ
ル(メタ)アクリレート,4−ヒドロキシブチル(メタ
)アクリレート,N−メチロールアクリルアミド,アリ
ルアルコールなどがあり,三級アミノ基を有するモノマ
ーとしては,ジメチルアミノエチル(メタ)アクリレー
ト,ジエチルアミノエチル(メタ)アクリレート,ジメ
チルアミノプロピル(メタ)アクリルアミドなどをあげ
ることができる。カルボキシル基を有するモノマーとし
ては,アクリル酸,メタクリル酸,クロトン酸,マレイ
ン酸,フマル酸,イタコン酸,シトラコン酸などがある
。アミド基,N−置換アミド基を有するモノマーとして
は,アクリルアミド,メタクリルアミド,N−メチル(
メタ)アクリルアミド,N−エチル(メタ)アクリルア
ミド,N−メトキシメチル(メタ)アクリルアミド,N
−エトキシメチル(メタ)アクリルアミド,N−プロポ
キシメチル(メタ)アクリルアミド,N−ブトキシメチ
ル(メタ)アクリルアミド,N−tert−ブチルアク
リルアミド,N−オクチルアクリルアミド,ジアセトン
アクリルアミドなどがある。ニトリル基を有するモノマ
ーとしては,アクリロニトリル,メタクリロニトリル,
クロトノニトリル,フマロニトリルなどがある。また,
アルキル(メタ)アクリレートとしては,メチル(メタ
)アクリレート,エチル(メタ)アクリレート,ブチル
(メタ)アクリレート,2−エチルヘキシル(メタ)ア
クリレート,オクチル(メタ)アクリレートなどのアル
キル(メタ)アクリレートがある。その他,シクロヘキ
シル(メタ)アクリレート,ベンジル(メタ)アクリレ
ート,テトラヒドロフルフリル(メタ)アクリレートな
どやアルキル基が芳香環基,複素環基,ハロゲン原子な
どで置換されているアルキル(メタ)アクリレートなど
,一般にアクリルポリマーの合成に用いられるモノマー
を本発明のポリマーの合成にも用いることができる。Examples of monomers having a hydroxyl group include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and N-methylolacrylamide. , allyl alcohol, etc. Examples of monomers having a tertiary amino group include dimethylaminoethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, and dimethylaminopropyl (meth)acrylamide. Examples of monomers having a carboxyl group include acrylic acid, methacrylic acid, crotonic acid, maleic acid, fumaric acid, itaconic acid, and citraconic acid. Examples of monomers having an amide group or an N-substituted amide group include acrylamide, methacrylamide, and N-methyl (
meth)acrylamide, N-ethyl(meth)acrylamide, N-methoxymethyl(meth)acrylamide, N
Examples include -ethoxymethyl (meth)acrylamide, N-propoxymethyl (meth)acrylamide, N-butoxymethyl (meth)acrylamide, N-tert-butylacrylamide, N-octylacrylamide, diacetone acrylamide, and the like. Monomers with nitrile groups include acrylonitrile, methacrylonitrile,
Examples include crotononitrile and fumaronitrile. Also,
Examples of alkyl (meth)acrylates include alkyl (meth)acrylates such as methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, and octyl (meth)acrylate. In addition, cyclohexyl (meth)acrylate, benzyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, etc., and alkyl (meth)acrylates in which the alkyl group is substituted with an aromatic ring group, a heterocyclic group, a halogen atom, etc. Monomers used in the synthesis of acrylic polymers can also be used in the synthesis of the polymers of the present invention.
【0020】反応は通常のラジカル重合であり,反応方
法に何等制限はなく,溶液重合,塊状重合,乳化重合な
どの公知の重合法で行なうことができるが,反応のコン
トロールが容易であることや直接次の操作に移れること
から溶液重合が好ましい。溶媒としては,メチルエチル
ケトン,メチルイソブチルケトン,トルエン,セロソル
ブ,酢酸エチル,酢酸ブチルなど本発明の樹脂が溶解す
るものであれば何でもよく,単独でも,複数の溶媒を混
合してもよい。また,重合反応の際に使用される重合開
始剤もベンゾイルパーオキサイド,アセチルパーオキサ
イド,メチルエチルケトンパーオキサイド,ラウロイル
パーオキサイドなどの有機過酸化物,アゾビスイソブチ
ロニトリルなどのアゾ系開始剤など,とくに制限はない
。The reaction is a normal radical polymerization, and there are no restrictions on the reaction method, and it can be carried out using known polymerization methods such as solution polymerization, bulk polymerization, and emulsion polymerization. Solution polymerization is preferred because it allows the process to proceed directly to the next operation. Any solvent may be used as long as it dissolves the resin of the present invention, such as methyl ethyl ketone, methyl isobutyl ketone, toluene, cellosolve, ethyl acetate, butyl acetate, etc., and it may be used alone or in combination of multiple solvents. In addition, polymerization initiators used during polymerization reactions include organic peroxides such as benzoyl peroxide, acetyl peroxide, methyl ethyl ketone peroxide, and lauroyl peroxide, and azo initiators such as azobisisobutyronitrile. There are no particular restrictions.
【0021】それぞれの反応によって得られたポリエス
テルオリゴマー(A)と粘着性アクリルポリマー(B)
を混合することにより,樹脂組成物を得ることができる
。混合は,室温で見かけ上均一になる程度まで撹拌すれ
ば十分であるが,相互の混合の状態をより高めるために
,溶媒の沸点以下の温度での加熱撹拌を行なってもよい
。Polyester oligomer (A) and adhesive acrylic polymer (B) obtained by each reaction
A resin composition can be obtained by mixing. For mixing, it is sufficient to stir the materials at room temperature until they become apparently homogeneous, but in order to further improve the state of mutual mixing, heating and stirring may be performed at a temperature below the boiling point of the solvent.
【0022】以上のようにして得られた組成物は,ポリ
エステルオリゴマー(A)と粘着性アクリルポリマー(
B)との相溶性があまり良くないために,おそらくミク
ロ相分離構造をとっていると考えられる。それは,特に
高濃度の溶液や,この組成物をフィルム上に塗工した場
合には白濁を生じるものがあることからもわかる。しか
し,静置状態で分離することはなく,均一な状態を保っ
ている。一般的に相溶性のよいオリゴマーを添加した場
合には,粘着力を向上させることができても凝集力,特
に高温での凝集力が低下してしまうのに対して,本発明
のようにミクロ相分離構造をとる樹脂組成の場合には,
添加するポリエステルオリゴマー(A)の組成にも大き
く影響されるが,概ね凝集力を低下させないことが特徴
である。特に,粘度や軟化点の高いオリゴマーを用いた
ときには,充填剤としての働きに近い効果を示し,凝集
力を大きく向上させることができる。The composition obtained as described above contains the polyester oligomer (A) and the adhesive acrylic polymer (A).
It is thought that because the compatibility with B) is not very good, it probably has a microphase-separated structure. This can be seen from the fact that some solutions, especially those with high concentrations, or when this composition is coated onto a film, produce white turbidity. However, it does not separate when left standing and remains uniform. In general, when oligomers with good compatibility are added, the cohesive force, especially at high temperatures, decreases even though the adhesion can be improved. In the case of a resin composition with a phase-separated structure,
Although it is greatly influenced by the composition of the polyester oligomer (A) to be added, it is characterized in that it generally does not reduce the cohesive force. In particular, when oligomers with high viscosity and softening points are used, they exhibit an effect similar to that of a filler and can significantly improve cohesive force.
【0023】また,粘着特性を改善し,特に凝集力を高
めるために,ポリイソシアネート(C)を添加して,粘
着性アクリルポリマー(B)を部分架橋させる。このよ
うなポリイソシアネートとしてはトリレンジイソシアネ
ート,4,4´−ジフェニルメタンジイソシアネート,
ヘキサメチレンジイソシアネート,m−キシレンジイソ
シアネート,p−キシレンジイソシアネート,1,5−
ナフタレンジイソシアネート,イソホロンジイソシアネ
ート,リジンジイソシアネート,水添4,4´−ジフェ
ニルメタンジイソシアネート,水添トリレンジイソシア
ネートなどのジイソシアネート類,あるいはこれらとグ
リコール類またはジアミン類との両末端イソシアネート
アダクト体,あるいはこれらの混合物があり,必要に応
じてトリフェニルメタントリイソシアネート,ポリメチ
レンポリフェニルイソシアネートなどの3官能以上のポ
リイソシアネート類もジイソシアネート類と混合して用
いることができる。ここで,アクリルポリマー(B)が
官能基を2種以上有する場合には,ポリイソシアネート
(C)との反応性の差により,主に架橋に寄与する官能
基と残存する官能基にわかれ,粘着性を十分に保ったま
ま,凝集力を著しく向上させることができる。また,ポ
リエステルオリゴマー(A)も1分子中に1個以上の官
能基を有するので,これがポリイソシアネート(C)と
反応して凝集力を高める効果を示すことも期待できる。In order to improve the adhesive properties and in particular to increase the cohesive strength, polyisocyanates (C) are also added to partially crosslink the adhesive acrylic polymer (B). Such polyisocyanates include tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate,
Hexamethylene diisocyanate, m-xylene diisocyanate, p-xylene diisocyanate, 1,5-
Diisocyanates such as naphthalene diisocyanate, isophorone diisocyanate, lysine diisocyanate, hydrogenated 4,4'-diphenylmethane diisocyanate, and hydrogenated tolylene diisocyanate, or double-terminated isocyanate adducts of these with glycols or diamines, or mixtures thereof. If necessary, tri- or higher functional polyisocyanates such as triphenylmethane triisocyanate and polymethylene polyphenylisocyanate can also be used in combination with diisocyanates. Here, when the acrylic polymer (B) has two or more types of functional groups, due to the difference in reactivity with the polyisocyanate (C), it is divided into functional groups that mainly contribute to crosslinking and functional groups that remain, resulting in adhesiveness. The cohesive force can be significantly improved while maintaining sufficient properties. Moreover, since the polyester oligomer (A) also has one or more functional groups in one molecule, it can be expected that this will react with the polyisocyanate (C) and exhibit the effect of increasing cohesive force.
【0024】さらに,セラミック,ガラス,金属などと
の接着性を向上させるため,および無機フィラーや無機
繊維との混和性を改善するためため,シランカップリン
グ剤(D)を加える。シランカップリング剤(D)は,
一般にX〜Si(OR)3の化学式で表わされる化合物
で,分子中に2個以上の異なった官能基を有している。
このうちのXは,ビニル基,アクリル基,メタクリル基
,アミノ基,エポキシ基,メルカプト基など有機質と反
応する基,もう一つのORはメトキシ基,エトキシ基,
ヒドロキシ基などのような加水分解可能な基である。ま
た,ORの代わりに水素原子,ハロゲン原子の場合もあ
る。いずれにしても,有機材料と無機材料のバインダー
としての働きをもっている。Furthermore, a silane coupling agent (D) is added to improve adhesion to ceramics, glass, metals, etc., and to improve miscibility with inorganic fillers and inorganic fibers. The silane coupling agent (D) is
Generally, it is a compound represented by the chemical formula of X to Si(OR)3, and has two or more different functional groups in the molecule. Among these, X is a group that reacts with organic substances such as vinyl group, acrylic group, methacrylic group, amino group, epoxy group, mercapto group, and the other OR is a methoxy group, ethoxy group,
A hydrolyzable group such as a hydroxy group. Also, a hydrogen atom or a halogen atom may be used instead of OR. In any case, it functions as a binder between organic and inorganic materials.
【0025】これらの中でビニルシラン,エポキシシラ
ン,メタクリルシラン,アミノシランおよびメルカプト
シランが使用可能であるが,発明者の実験結果によると
,とりわけビニルシラン,エポキシシラン,メタクリル
シランが前述の性能改善に効果があることが確認されて
いる。Among these, vinylsilane, epoxysilane, methacrylsilane, aminosilane, and mercaptosilane can be used, but according to the inventor's experimental results, vinylsilane, epoxysilane, and methacrylsilane are particularly effective in improving the above-mentioned performance. It has been confirmed that there is.
【0026】ビニルシランとしては,ビニルトリクロロ
シラン,ジビニルジクロロシラン,ビニルジメチルクロ
ロシラン,ビニルトリメトキシシラン,ビニルトリエト
キシシラン,ビニルトリス−(β−メトキシエトキシ)
シラン,p−アリルフェニルエチルジクロロシラン,p
−ビニルフェニルトリクロロシラン,アリルメチルジク
ロロシラン,ビニルジフェニルクロロシランなどが挙げ
られる。エポキシシランとしては,γ−グリシドキシプ
ロピルトリメトキシシラン,γ−グリシドキシプロピル
メチルジメトキシシラン,β−(3,4−エポキシシク
ロヘキシル)エチルトリメトキシシランなどが挙げられ
る。メタクリルシランとしては,γ−メタクリロキシプ
ロピルトリメトキシシラン,γ−メタクリロキシプロピ
ルメチルジメトキシシランなどが挙げられる。これらの
一種または二種以上が配合され,粘着剤用樹脂組成物と
される。Examples of the vinylsilane include vinyltrichlorosilane, divinyldichlorosilane, vinyldimethylchlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, and vinyltris-(β-methoxyethoxy).
Silane, p-allylphenylethyldichlorosilane, p
-Vinylphenyltrichlorosilane, allylmethyldichlorosilane, vinyldiphenylchlorosilane and the like. Examples of the epoxysilane include γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropylmethyldimethoxysilane, and β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane. Examples of methacrylsilane include γ-methacryloxypropyltrimethoxysilane and γ-methacryloxypropylmethyldimethoxysilane. One or more of these are blended to form a pressure-sensitive adhesive resin composition.
【0027】本発明の樹脂組成物には,その性能を阻害
しない範囲で,必要に応じて顔料,染料,無機充填剤,
有機溶剤,銀粉,銅粉,ニッケル粉などの金属粉,カー
ボンブラック,グラファイト,前出のポリエステルオリ
ゴマー(A)以外のオリゴマー類,キシレン樹脂やロジ
ン系樹脂などの粘着付与剤などを加えることができる。[0027] The resin composition of the present invention may contain pigments, dyes, inorganic fillers,
Organic solvents, metal powders such as silver powder, copper powder, and nickel powder, carbon black, graphite, oligomers other than the aforementioned polyester oligomer (A), and tackifiers such as xylene resin and rosin resin can be added. .
【0028】本発明の樹脂組成物は,通常の粘着テープ
,シートなどの製造法と同様,プラスチックフィルム,
紙,セロハン,布,不織布,金属箔などのフィルム,シ
ート,テープなどに塗工するか,シリコーン処理を施し
た紙や布,ポリエチレンテレフタレートフィルムラミネ
ート紙などの,低接着性の樹脂により加工を施した紙や
布,金属箔,プラスチックフィルムなどの剥離性の高い
フィルム,シートあるいはテープなどの上に塗工し,必
要があれば乾燥により有機溶剤を除去し,必要があれば
裁断し,両面または片面の粘着シートあるいはテープの
形にされる。また,補強や衝撃緩和のために,レーヨン
,ナイロンなどの不織布や寒冷紗などの布類,紙,セロ
ハン,ポリエチレンテレフタレートフィルムなどのプラ
スチックフィルム類,金属箔,ウレタン,アクリルなど
のフォーム類などでライニングしたり,これらの布類,
フィルム類,フォーム類などを芯材としてこれに本発明
の樹脂組成物を塗布または含浸させて用いることもでき
る。[0028] The resin composition of the present invention can be used in plastic films,
It is coated on films, sheets, tapes, etc. such as paper, cellophane, cloth, non-woven fabrics, and metal foils, or processed with low-adhesive resins such as silicone-treated paper or cloth, polyethylene terephthalate film laminated paper, etc. Coat it on a highly releasable film, sheet, or tape such as paper, cloth, metal foil, or plastic film, remove the organic solvent by drying if necessary, cut it if necessary, and apply it on both sides or Formed into a single-sided adhesive sheet or tape. In addition, for reinforcement and impact mitigation, linings are made of nonwoven fabrics such as rayon and nylon, fabrics such as cheesecloth, paper, cellophane, plastic films such as polyethylene terephthalate film, and foams such as metal foil, urethane, and acrylic. or these cloths,
It is also possible to use films, foams, etc. as core materials by coating or impregnating them with the resin composition of the present invention.
【0029】[0029]
【実施例】以下,実施例により本発明を説明する。例中
,部とは重量部を,%とは重量%を,それぞれ表わす。EXAMPLES The present invention will be explained below with reference to Examples. In the examples, "part" means part by weight, and "%" means percent by weight.
【0030】ポリエステルオリゴマーの合成Synthesis of polyester oligomer
【0031
】
オリゴマー1
p−ヒドロキシ安息香酸
4.3部ヘキサヒドロ無水フタル酸
48.5部フェニルグリシジルエーテル
47.2部N,N−ジメチルベンジル
アミン 0.9部酢酸エチル
25.0
部上記組成物を混合し,空気雰囲気中,80℃で10時
間反応させ,冷却後,酢酸エチル125部を加えて,ポ
リエステルオリゴマー1の溶液(固形分40%)を得た
。0031
] Oligomer 1 p-hydroxybenzoic acid
4.3 parts hexahydrophthalic anhydride
48.5 parts phenyl glycidyl ether
47.2 parts N,N-dimethylbenzylamine 0.9 parts ethyl acetate
25.0
The above compositions were mixed and reacted in an air atmosphere at 80° C. for 10 hours. After cooling, 125 parts of ethyl acetate was added to obtain a solution of polyester oligomer 1 (solid content: 40%).
【0032】
オリゴマー2
エチレングリコール
2.0部ヘキサヒドロ無水フタル酸
51.0部グリシジルメタクリレート
47.0部N,N−ジメチルベ
ンジルアミン 0.9部ハイドロキノン
0
.2部酢酸エチル
25.0部上記組成物を混合し,空
気雰囲気中,80℃で10時間反応させ,冷却後,酢酸
エチル125部を加えて,ポリエステルオリゴマー2の
溶液(固形分40%)を得た。Oligomer 2 Ethylene glycol
2.0 parts hexahydrophthalic anhydride
51.0 parts glycidyl methacrylate
47.0 parts N,N-dimethylbenzylamine 0.9 parts Hydroquinone 0
.. 2 parts ethyl acetate
25.0 parts of the above composition were mixed and reacted in an air atmosphere at 80° C. for 10 hours. After cooling, 125 parts of ethyl acetate was added to obtain a solution of polyester oligomer 2 (solid content: 40%).
【0033】
オリゴマー3
p−ヒドロキシ安息香酸
4.5部ヘキサヒドロ無水フタル酸
49.7部グリシジルメタクリレート
45.8部N,N−ジメチルベンジ
ルアミン 0.9部ハイドロキノン
0.2
部酢酸エチル
25.0部Oligomer 3 p-hydroxybenzoic acid
4.5 parts hexahydrophthalic anhydride
49.7 parts glycidyl methacrylate
45.8 parts N,N-dimethylbenzylamine 0.9 part hydroquinone
0.2
ethyl acetate
25.0 copies
【0034】上記組成物を混
合し,空気雰囲気中,80℃で10時間反応させ,冷却
後,酢酸エチル125部を加えて,ポリエステルオリゴ
マー3の溶液(固形分40%)を得た。The above compositions were mixed and reacted in an air atmosphere at 80° C. for 10 hours. After cooling, 125 parts of ethyl acetate was added to obtain a solution of polyester oligomer 3 (solid content: 40%).
【0035】アクリルポリマーの合成Synthesis of acrylic polymer
【0036】
ポリマー1
ブチルアクリレート
93.5部アクリル酸
1.4部2−ヒドロキ
シエチルメタクリレート 5.1部アゾビスイソ
ブチロニトリル 0.2部酢酸
エチル
150.0部80℃に加熱した上記の組成の混合物
125部に,上記の同組成の混合物125部を滴下し,
滴下終了後,12時間加熱還流させ,冷却し,アクリル
ポリマー1の溶液(固形分40%)を得た。Polymer 1 Butyl acrylate
93.5 parts acrylic acid
1.4 parts 2-hydroxyethyl methacrylate 5.1 parts azobisisobutyronitrile 0.2 parts ethyl acetate
150.0 parts To 125 parts of the mixture with the above composition heated to 80°C, 125 parts of the above mixture with the same composition was added dropwise,
After the dropwise addition was completed, the mixture was heated under reflux for 12 hours and cooled to obtain a solution of acrylic polymer 1 (solid content: 40%).
【0037】
ポリマー2
ブチルアクリレート
92.0部アクリルアミド
2.8部2−ヒドロキシエ
チルメタクリレート 5.2部アゾビスイソブチ
ロニトリル 0.2部酢酸エチ
ル
150.0部Polymer 2 Butyl acrylate
92.0 parts acrylamide
2.8 parts 2-hydroxyethyl methacrylate 5.2 parts azobisisobutyronitrile 0.2 parts ethyl acetate
150.0 copies
【0038】80℃に加熱した上記の組成
の混合物125部に,上記の同組成の混合物125部を
滴下し,滴下終了後,12時間加熱還流させ,冷却し,
アクリルポリマー2の溶液(固形分40%)を得た。To 125 parts of the mixture having the above composition heated to 80°C, 125 parts of the above mixture having the same composition was added dropwise, and after the addition was completed, the mixture was heated to reflux for 12 hours, cooled,
A solution of acrylic polymer 2 (solid content 40%) was obtained.
【0039】[0039]
【実施例1】オリゴマー1の溶液27.3部,ポリマー
1の溶液72.7部を十分に混合し,さらにトリレンジ
イソシアネート0.3部,γ−グリシドキシプロピルト
リメトキシシラン0.1部を添加し、粘着剤用樹脂組成
物を得た。得られた粘着剤用樹脂組成物を,2枚の離型
紙上に乾燥後の厚さが30μmとなるように塗布し,6
0℃で3分間乾燥後,それぞれを厚さ50μmのレーヨ
ン不織布の両面に貼り合わせて樹脂を含浸させて両面粘
着シートを得た。さらにこれを50℃で3日間熟成させ
,片側に50μmのポリエチレンテレフタレートフィル
ムを貼り着け,得られた粘着シートついて,剥離接着力
,タック,保持力を測定した。結果を表1に示す。なお
,測定は次のようにして行なった。[Example 1] 27.3 parts of a solution of oligomer 1 and 72.7 parts of a solution of polymer 1 were thoroughly mixed, and further 0.3 part of tolylene diisocyanate and 0.1 part of γ-glycidoxypropyltrimethoxysilane were mixed. was added to obtain a pressure-sensitive adhesive resin composition. The resulting pressure-sensitive adhesive resin composition was applied onto two pieces of release paper so that the thickness after drying was 30 μm.
After drying at 0° C. for 3 minutes, each was pasted on both sides of a 50 μm thick rayon nonwoven fabric and impregnated with resin to obtain a double-sided adhesive sheet. This was further aged at 50° C. for 3 days, a 50 μm polyethylene terephthalate film was attached to one side, and the resulting pressure-sensitive adhesive sheet was measured for peel adhesion, tack, and holding power. The results are shown in Table 1. Note that the measurements were performed as follows.
【0040】(1)剥離接着力
得られた粘着シートを幅25mmに切断し,表面をトル
エンで洗浄した厚さ10mmのガラス板に貼着し,30
分間放置した後,25℃,相対湿度65%の条件下,剥
離速度300mm/分で180度剥離接着力を測定した
。(1) Peel Adhesive Strength The adhesive sheet obtained was cut to a width of 25 mm, and was pasted on a 10 mm thick glass plate whose surface had been cleaned with toluene.
After standing for a minute, the adhesive strength was measured at 180° peeling at a peeling rate of 300 mm/min at 25° C. and 65% relative humidity.
【0041】(2)タック
傾斜角30度の斜面に得られた粘着シートをセットして
,25℃,相対湿度65%の条件下,助走距離10cm
で,ステンレススチール製ボールを転がし,粘着面10
cm以内のところで停止する最大のボールの番号を測定
した。ボールの番号は1/16から1まで31種類ある
「ボールの呼称」の32倍の数値で表示した。(2) The obtained adhesive sheet was set on a slope with a tack angle of 30 degrees, and the run-up distance was 10 cm under conditions of 25° C. and 65% relative humidity.
, roll the stainless steel ball, sticky side 10
The number of the largest ball that stopped within cm was measured. The ball numbers are 32 times the number of the 31 types of ball names, ranging from 1/16 to 1.
【0042】(3)保持力
得られた粘着シートを幅25mm,長さ100mmの大
きさに切断し,粘着面のうち,たて25mm,横25m
mの部分をトルエンで洗浄した厚さ10mmのガラス板
に貼着し,所定温度,荷重1kgで粘着シートがガラス
板より落下するまでの時間(秒)を測定した。(3) Cut the obtained adhesive sheet into pieces with a width of 25 mm and a length of 100 mm.
The part m was attached to a glass plate with a thickness of 10 mm that had been cleaned with toluene, and the time (seconds) until the adhesive sheet fell from the glass plate at a predetermined temperature and a load of 1 kg was measured.
【0043】[0043]
【実施例2】オリゴマー2の溶液37.7部,ポリマー
2の溶液62.3部を十分に混合し,さらにコロネート
L(日本ポリウレタン工業(株)製ポリイソシアネート
)0.5部,γ−グリシドキシプロピルトリメトキシシ
ラン0.1部を添加し、粘着剤用樹脂組成物を得た。
得られた粘着剤用樹脂組成物を,厚さ50μmのポリエ
チレンテレフタレートフィルム上に乾燥後の厚さが30
μmとなるように塗布し,60℃で3分間乾燥して粘着
シートを得た。得られた粘着シートについて,実施例1
と同様にして剥離接着力,タック,保持力を測定した。
結果を表1に示す。[Example 2] 37.7 parts of a solution of oligomer 2 and 62.3 parts of a solution of polymer 2 were thoroughly mixed, and 0.5 part of Coronate L (polyisocyanate manufactured by Nippon Polyurethane Industries, Ltd.) and γ-glyceride were added. 0.1 part of sidoxypropyltrimethoxysilane was added to obtain a resin composition for an adhesive. The resulting pressure-sensitive adhesive resin composition was placed on a polyethylene terephthalate film with a thickness of 50 μm to a thickness of 30 μm after drying.
It was coated to a thickness of μm and dried at 60° C. for 3 minutes to obtain a pressure-sensitive adhesive sheet. Regarding the obtained adhesive sheet, Example 1
Peel adhesion, tack, and holding power were measured in the same manner as above. The results are shown in Table 1.
【0044】[0044]
【実施例3】オリゴマー3の溶液38.0部,ポリマー
1の溶液62.0部を十分に混合し,さらにトリレンジ
イソシアネート0.5部,γ−グリシドキシプロピルト
リメトキシシラン0.1部を添加し、粘着剤用樹脂組成
物を得た。得られた粘着剤用樹脂組成物を,実施例2と
同様にして両面粘着シートを得,測定を行なった。結果
を表1に示す。[Example 3] 38.0 parts of a solution of oligomer 3 and 62.0 parts of a solution of polymer 1 were thoroughly mixed, and further 0.5 part of tolylene diisocyanate and 0.1 part of γ-glycidoxypropyltrimethoxysilane were mixed. was added to obtain a pressure-sensitive adhesive resin composition. A double-sided adhesive sheet was obtained from the obtained adhesive resin composition in the same manner as in Example 2, and measurements were performed. The results are shown in Table 1.
【0045】[0045]
【比較例1】γ−グリシドキシプロピルトリメトキシシ
ラン0.1部を全く加えずに,実施例1と同様にフィル
ム上に塗布して,粘着シートを得,測定を行なった。[Comparative Example 1] A pressure-sensitive adhesive sheet was obtained by coating on a film in the same manner as in Example 1 without adding any 0.1 part of γ-glycidoxypropyltrimethoxysilane, and measurements were performed.
【0046】[0046]
【比較例2】γ−グリシドキシプロピルトリメトキシシ
ラン0.1部を全く加えずに,実施例2と同様にフィル
ム上に塗布して,粘着シートを得,測定を行なった。Comparative Example 2 A pressure-sensitive adhesive sheet was obtained by coating on a film in the same manner as in Example 2, without adding any 0.1 part of γ-glycidoxypropyltrimethoxysilane, and measurements were performed.
【0047】[0047]
【比較例3】γ−グリシドキシプロピルトリメトキシシ
ラン0.1部を全く加えずに,実施例3と同様にフィル
ム上に塗布して,粘着シートを得,測定を行なった。以
上の結果を表1に示す。[Comparative Example 3] A pressure-sensitive adhesive sheet was obtained by coating on a film in the same manner as in Example 3 without adding any 0.1 part of γ-glycidoxypropyltrimethoxysilane, and measurements were performed. The above results are shown in Table 1.
【0048】[0048]
【表1】[Table 1]
【0049】[0049]
【発明の効果】本発明の樹脂組成物は,示されたように
剥離接着力が2000g/25mm以上,タックが7以
上,保持力が24時間以上であり,粘着特性およびその
バランスにも優れている。また,シランカップリング剤
を添加することにより,無機材料への接着性が向上して
いる。このように,本発明により,粘着力,凝集力とそ
のバランスが良好で,無機材料への接着性にも優れた粘
着剤用樹脂組成物が得られるようになった。Effects of the Invention As shown, the resin composition of the present invention has a peel adhesion of 2000 g/25 mm or more, a tack of 7 or more, a holding power of 24 hours or more, and has excellent adhesive properties and balance thereof. There is. Furthermore, the adhesion to inorganic materials is improved by adding a silane coupling agent. As described above, the present invention has made it possible to obtain a resin composition for adhesives that has good adhesive force, cohesive force, and a good balance thereof, and also has excellent adhesiveness to inorganic materials.
Claims (1)
(b)を反応させて得られるポリエステルオリゴマー(
A),粘着性アクリルポリマー(B),ポリイソシアネ
ート(C),シランカップリング剤(D)を含むことを
特徴とする粘着剤用樹脂組成物。Claim 1: A polyester oligomer obtained by reacting a cyclic acid anhydride (a) and an epoxide (b) (
A resin composition for an adhesive, comprising: A), an adhesive acrylic polymer (B), a polyisocyanate (C), and a silane coupling agent (D).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3802291A JPH04255780A (en) | 1991-02-07 | 1991-02-07 | Resin composition for tacky agent |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3802291A JPH04255780A (en) | 1991-02-07 | 1991-02-07 | Resin composition for tacky agent |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH04255780A true JPH04255780A (en) | 1992-09-10 |
Family
ID=12513953
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP3802291A Pending JPH04255780A (en) | 1991-02-07 | 1991-02-07 | Resin composition for tacky agent |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH04255780A (en) |
-
1991
- 1991-02-07 JP JP3802291A patent/JPH04255780A/en active Pending
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