JP2007523979A - 放射線硬化性接着剤組成物 - Google Patents
放射線硬化性接着剤組成物 Download PDFInfo
- Publication number
- JP2007523979A JP2007523979A JP2006554148A JP2006554148A JP2007523979A JP 2007523979 A JP2007523979 A JP 2007523979A JP 2006554148 A JP2006554148 A JP 2006554148A JP 2006554148 A JP2006554148 A JP 2006554148A JP 2007523979 A JP2007523979 A JP 2007523979A
- Authority
- JP
- Japan
- Prior art keywords
- acrylate
- methacrylate
- curable adhesive
- adhesive composition
- radiation curable
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 310
- 239000000853 adhesive Substances 0.000 title claims abstract description 219
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 219
- 230000005855 radiation Effects 0.000 title claims abstract description 209
- 239000011347 resin Substances 0.000 claims abstract description 373
- 229920005989 resin Polymers 0.000 claims abstract description 373
- 239000000178 monomer Substances 0.000 claims abstract description 213
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 119
- 125000003118 aryl group Chemical group 0.000 claims abstract description 64
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 108
- NJVOHKFLBKQLIZ-UHFFFAOYSA-N (2-ethenylphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1C=C NJVOHKFLBKQLIZ-UHFFFAOYSA-N 0.000 claims description 56
- -1 2-methylheptyl Chemical group 0.000 claims description 54
- 229920006243 acrylic copolymer Polymers 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 46
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 35
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 35
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 26
- 239000003999 initiator Substances 0.000 claims description 24
- 229920000058 polyacrylate Polymers 0.000 claims description 22
- 238000006116 polymerization reaction Methods 0.000 claims description 20
- 239000000758 substrate Substances 0.000 claims description 19
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 18
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical group COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 18
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 claims description 17
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 15
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 claims description 15
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 12
- LVGFPWDANALGOY-UHFFFAOYSA-N 8-methylnonyl prop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C=C LVGFPWDANALGOY-UHFFFAOYSA-N 0.000 claims description 12
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 11
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 10
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000010894 electron beam technology Methods 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 10
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 9
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 claims description 9
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 claims description 9
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 9
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 9
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 9
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 claims description 9
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 claims description 9
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 9
- ZWEDFBKLJILTMC-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-3-hydroxybutanoate Chemical compound CCOC(=O)CC(O)C(F)(F)F ZWEDFBKLJILTMC-UHFFFAOYSA-N 0.000 claims description 9
- DOULWWSSZVEPIN-UHFFFAOYSA-N isoproturon-monodemethyl Chemical compound CNC(=O)NC1=CC=C(C(C)C)C=C1 DOULWWSSZVEPIN-UHFFFAOYSA-N 0.000 claims description 9
- KCAMXZBMXVIIQN-UHFFFAOYSA-N octan-3-yl 2-methylprop-2-enoate Chemical compound CCCCCC(CC)OC(=O)C(C)=C KCAMXZBMXVIIQN-UHFFFAOYSA-N 0.000 claims description 9
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 claims description 9
- 229940065472 octyl acrylate Drugs 0.000 claims description 9
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 claims description 9
- 229920001451 polypropylene glycol Polymers 0.000 claims description 9
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 claims description 9
- 101000771640 Homo sapiens WD repeat and coiled-coil-containing protein Proteins 0.000 claims description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 8
- 102100029476 WD repeat and coiled-coil-containing protein Human genes 0.000 claims description 8
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 8
- 229940119545 isobornyl methacrylate Drugs 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 239000013557 residual solvent Substances 0.000 claims description 8
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims description 7
- COCLLEMEIJQBAG-UHFFFAOYSA-N 8-methylnonyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCCCOC(=O)C(C)=C COCLLEMEIJQBAG-UHFFFAOYSA-N 0.000 claims description 7
- 239000012298 atmosphere Substances 0.000 claims description 7
- 239000003431 cross linking reagent Substances 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 150000002924 oxiranes Chemical class 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 5
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 239000006188 syrup Substances 0.000 claims description 5
- 235000020357 syrup Nutrition 0.000 claims description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 4
- 206010073306 Exposure to radiation Diseases 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 239000011127 biaxially oriented polypropylene Substances 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 4
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 4
- FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical compound CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 claims description 3
- CEXQWAAGPPNOQF-UHFFFAOYSA-N 2-phenoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=CC=CC=C1 CEXQWAAGPPNOQF-UHFFFAOYSA-N 0.000 claims description 3
- YHSYGCXKWUUKIK-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC(=O)C=C YHSYGCXKWUUKIK-UHFFFAOYSA-N 0.000 claims description 3
- FHPDNLOSEWLERE-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCOC(=O)C(C)=C FHPDNLOSEWLERE-UHFFFAOYSA-N 0.000 claims description 3
- FJKZPONBPMKPLO-UHFFFAOYSA-N 3-prop-2-enoyloxypropyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCCOC(=O)C=C FJKZPONBPMKPLO-UHFFFAOYSA-N 0.000 claims description 3
- NUXLDNTZFXDNBA-UHFFFAOYSA-N 6-bromo-2-methyl-4h-1,4-benzoxazin-3-one Chemical compound C1=C(Br)C=C2NC(=O)C(C)OC2=C1 NUXLDNTZFXDNBA-UHFFFAOYSA-N 0.000 claims description 3
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 claims description 3
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 claims description 3
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 claims description 3
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 claims description 3
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 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 claims description 3
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 claims description 3
- RZFODFPMOHAYIR-UHFFFAOYSA-N oxepan-2-one;prop-2-enoic acid Chemical compound OC(=O)C=C.O=C1CCCCCO1 RZFODFPMOHAYIR-UHFFFAOYSA-N 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 3
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 claims description 3
- KEROTHRUZYBWCY-UHFFFAOYSA-N tridecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C(C)=C KEROTHRUZYBWCY-UHFFFAOYSA-N 0.000 claims description 3
- XOALFFJGWSCQEO-UHFFFAOYSA-N tridecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C=C XOALFFJGWSCQEO-UHFFFAOYSA-N 0.000 claims description 3
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims description 3
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical class C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 claims description 2
- LRTOHSLOFCWHRF-UHFFFAOYSA-N 1-methyl-1h-indene Chemical class C1=CC=C2C(C)C=CC2=C1 LRTOHSLOFCWHRF-UHFFFAOYSA-N 0.000 claims description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 claims description 2
- FTALTLPZDVFJSS-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl prop-2-enoate Chemical compound CCOCCOCCOC(=O)C=C FTALTLPZDVFJSS-UHFFFAOYSA-N 0.000 claims description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical class O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 claims description 2
- FUWWLJDRAHEFLI-UHFFFAOYSA-N 8-methylnonyl hydrogen sulfate Chemical compound CC(C)CCCCCCCOS(O)(=O)=O FUWWLJDRAHEFLI-UHFFFAOYSA-N 0.000 claims description 2
- 239000004641 Diallyl-phthalate Chemical class 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical class C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 2
- 150000003926 acrylamides Chemical class 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 2
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical class C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 claims description 2
- 239000000919 ceramic Substances 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims description 2
- 239000012933 diacyl peroxide Substances 0.000 claims description 2
- TVWTZAGVNBPXHU-NXVVXOECSA-N dioctyl (z)-but-2-enedioate Chemical compound CCCCCCCCOC(=O)\C=C/C(=O)OCCCCCCCC TVWTZAGVNBPXHU-NXVVXOECSA-N 0.000 claims description 2
- 239000003822 epoxy resin Substances 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 239000003063 flame retardant Substances 0.000 claims description 2
- 239000004088 foaming agent Substances 0.000 claims description 2
- 239000011888 foil Substances 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- 239000004745 nonwoven fabric Substances 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims description 2
- 239000000123 paper Substances 0.000 claims description 2
- 125000005634 peroxydicarbonate group Chemical group 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims description 2
- 239000004014 plasticizer Substances 0.000 claims description 2
- 229920000647 polyepoxide Polymers 0.000 claims description 2
- 229920000570 polyether Polymers 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 claims description 2
- 239000012779 reinforcing material Substances 0.000 claims description 2
- 229920006132 styrene block copolymer Polymers 0.000 claims description 2
- 229920001897 terpolymer Polymers 0.000 claims description 2
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims description 2
- 239000013008 thixotropic agent Substances 0.000 claims description 2
- 239000002759 woven fabric Substances 0.000 claims description 2
- IBDVWXAVKPRHCU-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC(=O)C(C)=C IBDVWXAVKPRHCU-UHFFFAOYSA-N 0.000 claims 2
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 claims 2
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 claims 2
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical group CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 claims 1
- 239000004721 Polyphenylene oxide Substances 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 229920006378 biaxially oriented polypropylene Polymers 0.000 claims 1
- 238000003847 radiation curing Methods 0.000 claims 1
- 229920005700 acResin® Polymers 0.000 description 50
- 239000000047 product Substances 0.000 description 37
- 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 36
- 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 36
- 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 36
- 150000002148 esters Chemical class 0.000 description 35
- 238000010521 absorption reaction Methods 0.000 description 33
- 239000002904 solvent Substances 0.000 description 31
- 238000000576 coating method Methods 0.000 description 24
- 238000009472 formulation Methods 0.000 description 22
- 239000011248 coating agent Substances 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- 230000000694 effects Effects 0.000 description 13
- 238000007757 hot melt coating Methods 0.000 description 12
- 238000001723 curing Methods 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- 206010070835 Skin sensitisation Diseases 0.000 description 10
- 231100000370 skin sensitisation Toxicity 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 239000004698 Polyethylene Substances 0.000 description 7
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 7
- 229910000831 Steel Inorganic materials 0.000 description 7
- 230000003247 decreasing effect Effects 0.000 description 7
- 239000010959 steel Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 238000001879 gelation Methods 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- 231100000220 OECD 429 (LLNA) Skin Sensitisation Toxicity 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 230000006870 function Effects 0.000 description 5
- 239000012943 hotmelt Substances 0.000 description 5
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 4
- 229920000178 Acrylic resin Polymers 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 210000001165 lymph node Anatomy 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 239000004006 olive oil Substances 0.000 description 3
- 235000008390 olive oil Nutrition 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- QUBBAXISAHIDNM-UHFFFAOYSA-N 1-ethyl-2,3-dimethylbenzene Chemical class CCC1=CC=CC(C)=C1C QUBBAXISAHIDNM-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 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
- 239000004831 Hot glue Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 206010070834 Sensitisation Diseases 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- GUUHFMWKWLOQMM-NTCAYCPXSA-N alpha-hexylcinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 description 2
- GUUHFMWKWLOQMM-UHFFFAOYSA-N alpha-n-hexylcinnamic aldehyde Natural products CCCCCCC(C=O)=CC1=CC=CC=C1 GUUHFMWKWLOQMM-UHFFFAOYSA-N 0.000 description 2
- 238000000540 analysis of variance Methods 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000013642 negative control Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical class CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000008313 sensitization Effects 0.000 description 2
- 238000010998 test method Methods 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
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- YQZBFMJOASEONC-UHFFFAOYSA-N 1-Methyl-2-propylbenzene Chemical class CCCC1=CC=CC=C1C YQZBFMJOASEONC-UHFFFAOYSA-N 0.000 description 1
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical class CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
- ZKEUVTROUPQVTM-UHFFFAOYSA-N 1-pentylperoxypentane Chemical compound CCCCCOOCCCCC ZKEUVTROUPQVTM-UHFFFAOYSA-N 0.000 description 1
- WBELHNUIWMNAFH-UHFFFAOYSA-N 12-prop-2-enoyloxydodecyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCCCCCCCOC(=O)C=C WBELHNUIWMNAFH-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- MCNPOZMLKGDJGP-QPJJXVBHSA-N 2-[(e)-2-(4-methoxyphenyl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=CC(OC)=CC=C1\C=C\C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 MCNPOZMLKGDJGP-QPJJXVBHSA-N 0.000 description 1
- JSLWEMZSKIWXQB-UHFFFAOYSA-N 2-dodecylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CCCCCCCCCCCC)=CC=C3SC2=C1 JSLWEMZSKIWXQB-UHFFFAOYSA-N 0.000 description 1
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 1
- 238000010600 3H thymidine incorporation assay Methods 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 241000157855 Cinchona Species 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 239000013032 Hydrocarbon resin Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 229920001890 Novodur Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- 239000003522 acrylic cement Substances 0.000 description 1
- 239000002313 adhesive film Substances 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 239000013566 allergen Substances 0.000 description 1
- 230000002009 allergenic effect Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000004054 benzoquinones Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical group CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002224 dissection Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- KFVBEPXIRVYOGP-UHFFFAOYSA-N dodecyl prop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CCCCCCCCCCCCOC(=O)C=C KFVBEPXIRVYOGP-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000009459 flexible packaging Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 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 1
- 229920006270 hydrocarbon resin Polymers 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000013383 initial experiment Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012939 laminating adhesive Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 210000004698 lymphocyte Anatomy 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
- 230000000873 masking effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100001083 no cytotoxicity Toxicity 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000010399 physical interaction Effects 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 125000003410 quininyl group Chemical group 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 231100000489 sensitizer Toxicity 0.000 description 1
- 231100000051 skin sensitiser Toxicity 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
- Y10T428/2852—Adhesive compositions
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
- Y10T428/2852—Adhesive compositions
- Y10T428/2878—Adhesive compositions including addition polymer from unsaturated monomer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
- Y10T428/2852—Adhesive compositions
- Y10T428/2878—Adhesive compositions including addition polymer from unsaturated monomer
- Y10T428/2891—Adhesive compositions including addition polymer from unsaturated monomer including addition polymer from alpha-beta unsaturated carboxylic acid [e.g., acrylic acid, methacrylic acid, etc.] Or derivative thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/780,996 US7238732B2 (en) | 2004-02-18 | 2004-02-18 | Radiation-curable adhesive compositions |
| PCT/US2005/004519 WO2005080518A1 (en) | 2004-02-18 | 2005-02-14 | Radiation-curable adhesive compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007523979A true JP2007523979A (ja) | 2007-08-23 |
| JP2007523979A5 JP2007523979A5 (enExample) | 2008-04-03 |
Family
ID=34838665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006554148A Pending JP2007523979A (ja) | 2004-02-18 | 2005-02-14 | 放射線硬化性接着剤組成物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7238732B2 (enExample) |
| EP (1) | EP1725626B1 (enExample) |
| JP (1) | JP2007523979A (enExample) |
| AT (1) | ATE366292T1 (enExample) |
| DE (1) | DE602005001556T2 (enExample) |
| WO (1) | WO2005080518A1 (enExample) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006144017A (ja) * | 2004-11-24 | 2006-06-08 | Natl Starch & Chem Investment Holding Corp | 医療用途用ホトメルト接着剤 |
| JP2010074165A (ja) * | 2008-09-18 | 2010-04-02 | Tesa Se | 電子的装置のカプセル化方法 |
| WO2010134521A1 (ja) * | 2009-05-22 | 2010-11-25 | 日東電工株式会社 | 紫外線硬化型粘着剤組成物、粘着剤層、粘着シートおよびその製造方法 |
| KR101353331B1 (ko) * | 2009-03-03 | 2014-01-17 | 히다치 막셀 가부시키가이샤 | 방사선 경화성 점착제 조성물, 그것을 사용한 다이싱용 점착 필름 및 절단편의 제조방법 |
| KR20180049032A (ko) * | 2015-09-08 | 2018-05-10 | 테사 소시에타스 유로파에아 | 접착제-수지-개질된 접착제 물질 |
| KR20190043102A (ko) * | 2017-10-17 | 2019-04-25 | 테사 소시에타스 유로파에아 | 비닐방향족 블록 코폴리머를 기반으로 한 경화 가능한 감압 접착제 스트립 |
| JP2020525601A (ja) * | 2017-06-27 | 2020-08-27 | サートプラスト・テヒニシェ・クレーベベンダー・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 接着テープの製造方法 |
| KR102352247B1 (ko) * | 2021-03-14 | 2022-01-18 | 주식회사 엘에스이피에스파주 | 단열효과를 향상시킨 준불연 eps 내외장 다중 합치판넬 및 그 제조방법 |
| JP2022511052A (ja) * | 2018-12-05 | 2022-01-28 | ハンワ ソリューションズ コーポレイション | ジシクロペンタジエン系樹脂、ジシクロペンタジエン系水添樹脂およびこれを含む接着樹脂組成物 |
| JPWO2022230027A1 (enExample) * | 2021-04-26 | 2022-11-03 |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10201420A1 (de) * | 2002-01-15 | 2003-07-24 | Basf Ag | Strahlungshärtbare Beschichtungen mit verbesserter Haftung |
| US7262242B2 (en) * | 2004-02-18 | 2007-08-28 | Eastman Chemical Company | Aromatic/acrylate tackifier resin and acrylic polymer blends |
| US7332540B2 (en) * | 2004-02-18 | 2008-02-19 | Eastman Chemical Company | Aromatic-acrylate tackifier resins |
| US20080041520A1 (en) * | 2006-08-18 | 2008-02-21 | Dentsply Research And Development Corp. | Adhesive and method for binding artificial plastic teeth |
| WO2007038322A1 (en) * | 2005-09-23 | 2007-04-05 | National Starch And Chemical Investment Holding Corporation | Acrylic polymer-based adhesives |
| US7754327B2 (en) * | 2006-05-11 | 2010-07-13 | Henkel Ag & Co. Kgaa | Absorbent articles comprising a radiation cured hot melt positioning adhesive |
| US20080026662A1 (en) * | 2006-07-25 | 2008-01-31 | Ecology Coatings, Inc. | Flexible Surface Having a UV Curable Waterproofing Composition |
| US20080027154A1 (en) * | 2006-07-25 | 2008-01-31 | Ecology Coatings, Inc. | Uv curable compositions for use in adhesion, repair and architectural enhancement |
| EP2082004B1 (en) * | 2006-11-07 | 2017-01-18 | Henkel AG & Co. KGaA | Antistatic protective hot melt adhesives |
| JP5016296B2 (ja) * | 2006-11-22 | 2012-09-05 | 東京応化工業株式会社 | 接着剤組成物、及び接着フィルム |
| JP4976829B2 (ja) * | 2006-11-29 | 2012-07-18 | 東京応化工業株式会社 | 接着剤組成物、及び接着フィルム |
| DE102007030407A1 (de) * | 2007-06-29 | 2009-01-02 | Henkel Ag & Co. Kgaa | Etiketten mit wasserlösbaren UV-härtenden Klebstoffen |
| CN102216375B (zh) * | 2008-10-03 | 2013-11-06 | 乌波诺尔创新股份公司 | 用于涂覆管道的方法和组合物 |
| DE102009006591A1 (de) * | 2009-01-29 | 2010-08-05 | Tesa Se | Haftklebemasse |
| JP5235001B2 (ja) * | 2009-07-16 | 2013-07-10 | 日東電工株式会社 | 粘着シート |
| JP5731137B2 (ja) * | 2010-06-15 | 2015-06-10 | 電気化学工業株式会社 | エキシマ光照射による接着体の解体方法 |
| US9358576B2 (en) | 2010-11-05 | 2016-06-07 | International Paper Company | Packaging material having moisture barrier and methods for preparing same |
| US9365980B2 (en) | 2010-11-05 | 2016-06-14 | International Paper Company | Packaging material having moisture barrier and methods for preparing same |
| JP2014517857A (ja) * | 2011-04-27 | 2014-07-24 | ヘンケル・ユーエス・アイピー・リミテッド・ライアビリティ・カンパニー | 低温シーリング機能を備える硬化性エラストマー組成物 |
| TWI490299B (zh) * | 2011-05-05 | 2015-07-01 | Eternal Materials Co Ltd | 丙烯酸系黏著組合物及其用途 |
| US8871827B2 (en) * | 2011-06-07 | 2014-10-28 | Basf Se | Hotmelt adhesive comprising radiation-crosslinkable poly(meth)acrylate and oligo(meth)acrylate with nonacrylic C-C double bonds |
| JP6230233B2 (ja) * | 2012-04-23 | 2017-11-15 | 日東電工株式会社 | 表面保護フィルム |
| CN104272370B (zh) | 2012-05-09 | 2016-12-07 | 迪睿合电子材料有限公司 | 图像显示装置的制造方法 |
| CN102732159B (zh) * | 2012-06-25 | 2014-04-09 | 烟台开发区泰盛精化新材料有限公司 | 一种可剥性防焊紫外固化胶及其制备和使用方法 |
| US10541183B2 (en) * | 2012-07-19 | 2020-01-21 | Texas Instruments Incorporated | Spectral reflectometry window heater |
| WO2014065126A1 (ja) * | 2012-10-22 | 2014-05-01 | 三菱樹脂株式会社 | 透明両面粘着シート及びこれを用いた画像表示装置 |
| EP2924092A4 (en) * | 2012-11-21 | 2016-10-12 | Alcare Co Ltd | HAFFET COMPOSITION, HAIR SKIN AND HAIR SKIN |
| CN102965037A (zh) * | 2012-11-26 | 2013-03-13 | 山东天鼎丰非织造布有限公司 | 非织造布胶粘剂 |
| CN102965067B (zh) * | 2012-12-13 | 2014-07-23 | 东莞市贝特利新材料有限公司 | 一种紫外光固化液态光学胶 |
| WO2014111292A1 (en) | 2013-01-18 | 2014-07-24 | Basf Se | Acrylic dispersion-based coating compositions |
| EP2803712A1 (en) | 2013-05-17 | 2014-11-19 | 3M Innovative Properties Company | Multilayer Pressure Sensitive Adhesive Assembly |
| CN104163884B (zh) * | 2013-05-20 | 2016-12-28 | 3M创新有限公司 | 可固化的丙烯酸类组合物、丙烯酸类胶带、丙烯酸类胶辊以及制备该丙烯酸类胶辊的方法 |
| DE102013106576A1 (de) * | 2013-06-24 | 2014-12-24 | Coroplast Fritz Müller Gmbh & Co. Kg | "Klebeband, insbesondere doppelseitiges Klebeband, und dessen Verwendung zum Bekleben unpolarer Oberflächen" |
| WO2015042258A1 (en) | 2013-09-18 | 2015-03-26 | Firestone Building Products Co., LLC | Peel and stick roofing membranes with cured pressure-sensitive adhesives |
| CN103740286B (zh) * | 2013-12-09 | 2016-02-24 | 北京保利世达科技有限公司 | 一种可见光固化胶黏剂及其制备方法 |
| CN103820037A (zh) * | 2014-03-12 | 2014-05-28 | 深圳市中显微电子有限公司 | 一种耐黄变液态光学胶粘剂及其制备方法 |
| CN103820038A (zh) * | 2014-03-12 | 2014-05-28 | 深圳市中显微电子有限公司 | 一种高耐候性液态光学胶粘剂及其制备方法 |
| EP3122833B1 (en) | 2014-03-26 | 2020-01-01 | 3M Innovative Properties Company | Ultraviolet cured (meth)acrylate pressure-sensitive adhesive composition and process for producing thereof |
| EP2957303A1 (en) | 2014-06-20 | 2015-12-23 | Nitto Denko Corporation | Curable composition and skin adhesive |
| WO2017165868A1 (en) | 2016-03-25 | 2017-09-28 | Firestone Building Products Co., LLC | Fully-adhered roof system adhered and seamed with a common adhesive |
| WO2017165870A1 (en) | 2016-03-25 | 2017-09-28 | Firestone Building Products Co., LLC | Fabric-backed roofing membrane composite |
| US20200299967A1 (en) | 2016-03-25 | 2020-09-24 | Firestone Building Products Company, Llc | Method of reroofing |
| US12006692B2 (en) | 2016-03-25 | 2024-06-11 | Holcim Technology Ltd | Fully-adhered roof system adhered and seamed with a common adhesive |
| DE102017114266B9 (de) * | 2017-06-27 | 2020-09-17 | Certoplast Technische Klebebänder Gmbh | Verfahren zur Herstellung eines Wickelbandes |
| DE102017221702A1 (de) * | 2017-12-01 | 2019-06-06 | Tesa Se | Chemikalienbeständiges Polyacrylat und darauf basierende Haftklebmasse |
| DE102018118972B4 (de) * | 2018-08-03 | 2024-02-01 | Lohmann Gmbh & Co. Kg | Klebeband zur Verklebung von PTFE, PE, PP und Autolacken und Verfahren zur Herstellung |
| CN109705751A (zh) * | 2018-12-10 | 2019-05-03 | 江阴美源实业有限公司 | 溶剂型双面胶带、胶带用胶黏剂及制备方法 |
| WO2020180435A1 (en) * | 2019-03-01 | 2020-09-10 | Dow Global Technologies Llc | Tackifier composition |
| WO2021026208A1 (en) * | 2019-08-06 | 2021-02-11 | Henkel IP & Holding GmbH | Radiation transmissive fillers improving the depth of cure in high optical density light curable materials |
| CN111205777B (zh) * | 2020-03-03 | 2020-12-29 | 深圳市勇泰运科技有限公司 | 三官能团树脂及紫外光和加热双重固化胶粘剂的制备方法 |
| WO2021225870A1 (en) * | 2020-05-07 | 2021-11-11 | Washington State University | Aliphatic amine and nitrile synthesis through catalytic co hydrogenation in the presence of ammonia |
| EP4083104B1 (en) | 2021-04-28 | 2023-08-16 | Lawter, Inc. | Tackifier for adhesive composition |
| CN114853939A (zh) * | 2022-05-11 | 2022-08-05 | 苏州德佑新材料科技股份有限公司 | 一种溶剂型丙烯酸酯压敏胶粘剂及其制备方法 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS543136A (en) * | 1977-06-08 | 1979-01-11 | Arakawa Chem Ind Co Ltd | Pressure-sensitive adhesives |
| JP2001049200A (ja) * | 1999-08-11 | 2001-02-20 | Soken Chem & Eng Co Ltd | アクリル系粘着剤組成物、該組成物を用いた粘着テープの製造方法および粘着テープ |
| JP2001055405A (ja) * | 1999-06-24 | 2001-02-27 | Wacker Polymer Systems Gmbh & Co Kg | 水性ビニルアロマート−1,3−ジエン−コポリマー分散液および該分散液から得られる再分散粉末の臭気放出を減少させるための方法、および該方法により得られた生成物の使用 |
| WO2001088052A1 (fr) * | 2000-05-15 | 2001-11-22 | Toagosei Co., Ltd. | Agent collant et composition adhesive |
| WO2003068280A1 (en) * | 2002-02-14 | 2003-08-21 | Lintec Corporation | Medical pressure-sensitive adhesive composition, process for producing the same, and medical tape |
Family Cites Families (99)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3203935A (en) | 1962-05-07 | 1965-08-31 | O Brien Corp | Polymeric compositions of terpolymers reacted with aminohydroxy compounds |
| DE1965740C3 (de) | 1969-12-31 | 1979-11-22 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von pulverisierbaren Acryl-Harzen |
| US4077926A (en) | 1970-11-12 | 1978-03-07 | Rohm And Haas Company | Pressure sensitive adhesive containing polymerized alkoxyalkyl ester of unsaturated carboxylic acid |
| NL173538C (nl) | 1973-04-09 | 1984-02-01 | Monsanto Co | Werkwijze voor de bereiding van een oplossing in organisch oplosmiddel van een drukgevoelige, kruipvaste, permanent kleverige hars en gevormde voortbrengselen, vervaardigd onder toepassing van de aldus bereide oplossing. |
| US3991136A (en) | 1975-04-02 | 1976-11-09 | Monsanto Company | Method of producing ABS polyblends having a low residual monomer content |
| CA1068047A (en) | 1976-11-23 | 1979-12-11 | George F. Adams | Reaction process and apparatus for continuous polymerization |
| DE2703311A1 (de) | 1977-01-27 | 1978-08-03 | Bayer Ag | Niedermolekulare acrylatharze und ein verfahren zu ihrer herstellung |
| US4537734A (en) | 1977-10-07 | 1985-08-27 | Radiation Dynamics, Inc. | Method for reducing the monomer content in acrylonitrile containing polymers |
| US4305854A (en) | 1978-07-31 | 1981-12-15 | Polychrome Corporation | Radiation curable pressure sensitive adhesive |
| US4243500A (en) | 1978-12-04 | 1981-01-06 | International Coatings, Co., Inc. | Pressure sensitive adhesives |
| US4483951A (en) | 1979-06-06 | 1984-11-20 | The Standard Products Company | Radiation curable adhesive compositions and composite structures |
| US4303485A (en) | 1979-08-20 | 1981-12-01 | Minnesota Mining And Manufacturing Company | Ultraviolet polymerization of acrylate monomers using oxidizable tin compounds |
| US4391687A (en) | 1980-02-14 | 1983-07-05 | Minnesota Mining And Manufacturing Company | Photoactive mixture of acrylic monomers and chromophore-substituted halomethyl-1-triazine |
| US4329384A (en) | 1980-02-14 | 1982-05-11 | Minnesota Mining And Manufacturing Company | Pressure-sensitive adhesive tape produced from photoactive mixture of acrylic monomers and polynuclear-chromophore-substituted halomethyl-2-triazine |
| US4330590A (en) | 1980-02-14 | 1982-05-18 | Minnesota Mining And Manufacturing Company | Photoactive mixture of acrylic monomers and chromophore-substituted halomethyl-2-triazine |
| JPS56149481A (en) | 1980-04-21 | 1981-11-19 | Hitachi Chem Co Ltd | Adhesive composition for self-adhesive film |
| IT1198338B (it) | 1980-07-02 | 1988-12-21 | Montedison Spa | Processo per produrre copolimeri di monomeri vinil-aromatici con nitrili etilenicamente insaturi |
| DE3039268A1 (de) | 1980-10-17 | 1982-05-19 | Bayer Ag, 5090 Leverkusen | Gegen thermolyse stabilisierte formmassen mit geringem monomerengehalt |
| FR2497518A1 (fr) | 1981-01-05 | 1982-07-09 | Ato Chimie | Compositions adhesives thermofusibles a base de copolyetheramides sequences |
| US4529787A (en) | 1982-06-15 | 1985-07-16 | S. C. Johnson & Son, Inc. | Bulk polymerization process for preparing high solids and uniform copolymers |
| FR2533577B1 (fr) | 1982-09-27 | 1986-02-28 | Norton Sa | Compositions thermoplastiques adhesives |
| JPS60144303A (ja) | 1983-12-27 | 1985-07-30 | Dainippon Ink & Chem Inc | ビニル重合体の製造法 |
| US4540739A (en) | 1984-04-10 | 1985-09-10 | Polysar Limited | Adhesive polymer latex |
| US4533566A (en) | 1984-07-05 | 1985-08-06 | Minnesota Mining And Manufacturing Company | Electron-beam adhesion-promoting treatment of polyester film base for silicone release liners |
| US4968559A (en) | 1985-02-14 | 1990-11-06 | Bando Chemical Industries. Ltd. | Pressure sensitive adhesive film with barrier layer |
| US5100963A (en) | 1985-03-14 | 1992-03-31 | Avery Dennison Corporation | Pressure-sensitive adhesives based on similar polymers |
| FR2579612A1 (fr) | 1985-03-29 | 1986-10-03 | Atochem | Procede d'assemblage de surfaces par application d'un joint en polyurethanne ou en polyetheramide, fusion superficielle de ce joint et refroidissement |
| EP0197460A3 (en) | 1985-04-02 | 1987-08-05 | HENKEL CORPORATION (a Delaware corp.) | Acrylic polyols having low residual monomer content |
| US4952435A (en) | 1985-10-03 | 1990-08-28 | Fuji Photo Film Co., Ltd. | Adhesive for a base-mounted flexible magnetic disc |
| US4695621A (en) | 1985-12-23 | 1987-09-22 | The Dow Chemical Company | Method for reducing residual monomers from oversized fat imbibing copolymer beads |
| US5236991A (en) | 1987-01-14 | 1993-08-17 | The Dow Chemical Company | In-situ tackified structured latex composition |
| US4968740A (en) | 1987-01-20 | 1990-11-06 | The Dow Chemical Company | Latex based adhesive prepared by emulsion polymerization |
| US5115008A (en) | 1987-06-03 | 1992-05-19 | Avery Dennison Corporation | Curable film forming compositions |
| US4948825A (en) | 1987-06-03 | 1990-08-14 | Avery International Corporation | Curable film forming compositions |
| DE3724709A1 (de) | 1987-07-25 | 1989-02-02 | Stockhausen Chem Fab Gmbh | Verfahren zur herstellung von polymerisaten mit niedrigem restmonomergehalt |
| ES2048202T3 (es) | 1987-08-14 | 1994-03-16 | Minnesota Mining & Mfg | Adhesivo sensible a la presion. |
| US5028484A (en) * | 1987-08-14 | 1991-07-02 | Minnesota Mining And Manufacturing Company | Pressure-sensitive adhesive |
| US4912169A (en) | 1987-10-14 | 1990-03-27 | Rohm And Haas Company | Adhesive compositions containing low molecular weight polymer additives |
| US5227213A (en) | 1987-11-30 | 1993-07-13 | Sunstar Giken Kabushiki Kaisha | Hot melt adhesive crosslinkable by ultraviolet irradiation, optical disc using the same and process for preparing thereof |
| US5104921A (en) | 1988-02-17 | 1992-04-14 | Shell Oil Company | Radiation cured polymer composition |
| FR2627499B1 (fr) | 1988-02-24 | 1990-08-03 | Hoechst France | Dispersion aqueuse de polymeres du type styrene-acrylique et son application pour l'obtention de compositions adhesives resistant a l'eau convenant notamment dans le domaine du carrelage |
| AU3313689A (en) | 1988-05-18 | 1989-11-23 | Minnesota Mining And Manufacturing Company | Tackified pressure sensitive adhesive |
| EP0354521A3 (de) | 1988-08-10 | 1990-03-07 | RXS Schrumpftechnik-Garnituren GmbH | Abrutschfester Schmelzkleber,insbesondere für Beschichtungen bei Schrumpfprodukten |
| US4988742A (en) | 1988-09-02 | 1991-01-29 | Minnesota Mining And Manufacturing Company | Tackified terpolymer adhesives |
| CA2001397A1 (en) | 1988-10-28 | 1990-04-28 | Tadao Shimomura | Method for production of acrylate and acrylate-containing polymer |
| US5112882A (en) | 1989-09-06 | 1992-05-12 | Minnesota Mining And Manufacturing Company | Radiation curable polyolefin pressure sensitive adhesive |
| US5244962A (en) | 1989-12-01 | 1993-09-14 | Avery Dennison Corporation | Olefin polymer based pressure-sensitive adhesives |
| US5242980A (en) | 1990-02-06 | 1993-09-07 | Exxon Chemical Patents Inc. | Ethylene-unsaturated alcohol or acid copolymer and epoxy crosslinker |
| US5373041A (en) | 1990-08-27 | 1994-12-13 | E. I. Du Pont De Nemours And Company | Hot melt pressure sensitive adhesives |
| DE69229680T2 (de) | 1991-11-27 | 2000-02-10 | Minnesota Mining And Mfg. Co., Saint Paul | Strahlenhaertbarer, druckempfindlicher klebstoff auf der basis gesaettigter polyolefine |
| TW274086B (enExample) | 1992-06-04 | 1996-04-11 | Shell Internat Res Schappej Bv | |
| DE69332400T2 (de) | 1992-07-02 | 2003-07-10 | H.B. Fuller Licensing & Financing, Inc. | Heisschmelzklebemasse |
| FR2694757B1 (fr) | 1992-08-12 | 1994-10-07 | Atochem Elf Sa | Procédé pour la préparation de polyacrylates superabsorbants à faible teneur en monomères résiduels. |
| DE4232472A1 (de) | 1992-09-28 | 1994-03-31 | Lohmann Gmbh & Co Kg | Haftschmelzkleber, Verfahren zu ihrer Herstellung und ihre Verwendung |
| SG49755A1 (en) | 1992-12-07 | 1998-06-15 | Minnesota Mining & Mfg | Adhesive for polycarbonate |
| CA2118777A1 (en) | 1993-04-13 | 1994-10-14 | Gaddam N. Babu | Radiation-curable poly(alpha-olefin) adhesives |
| US5859088A (en) | 1993-04-13 | 1999-01-12 | Minnesota Mining And Manufacturing Company | Radiation-curable poly(α-olefin) adhesives |
| IT1270356B (it) | 1993-05-17 | 1997-05-05 | P & G Spa | Composizione adesiva, relativi procedimenti ed impiego |
| DE69433554T2 (de) | 1993-11-10 | 2004-12-23 | Minnesota Mining & Manufacturing Company, St. Paul | Klebriggemachtes druckempfindliches Klebemittel |
| JP3539765B2 (ja) | 1994-07-19 | 2004-07-07 | 三井化学株式会社 | 粘着付与樹脂組成物 |
| DE69511491T2 (de) | 1994-07-22 | 2000-03-23 | National Starch And Chemical Investment Holding Corp., Wilmington | Verfahren zur Herstellung eines Polymers durch Lösungspolymerisation |
| EP0699800A2 (en) | 1994-08-31 | 1996-03-06 | National Starch and Chemical Investment Holding Corporation | Hot melt coatings for paper and paperboard |
| DE4432368A1 (de) | 1994-09-12 | 1996-03-14 | Lohmann Gmbh & Co Kg | Bei hoher Temperatur scherfeste, wasserlösliche Haftklebemasse |
| US5747551A (en) | 1994-12-05 | 1998-05-05 | Acheson Industries, Inc. | UV curable pressure sensitive adhesive composition |
| US5695837A (en) | 1995-04-20 | 1997-12-09 | Minnesota Mining And Manufacturing Company | Tackified acrylic adhesives |
| EP0824551A4 (en) | 1995-05-10 | 1999-04-28 | Avery Dennison Corp | PIGMENTED, UV-CURED, ACRYLIC-BASED, PRESSURE-SENSITIVE ADHESIVES AND METHOD FOR THE PRODUCTION THEREOF |
| JPH08333425A (ja) | 1995-06-07 | 1996-12-17 | Mitsui Petrochem Ind Ltd | 変性炭化水素樹脂及びその用途 |
| JP2896331B2 (ja) | 1995-08-30 | 1999-05-31 | 奇美実業股▲分▼有限公司 | ゴム変性スチレン系樹脂組成物 |
| DE19601697A1 (de) | 1996-01-18 | 1997-07-24 | Wacker Chemie Gmbh | Redispergierbare Tackifierpulver |
| US5777039A (en) | 1996-02-09 | 1998-07-07 | Shell Oil Company | Vinyl aromatic block copolymers and compositions containing them |
| US5874143A (en) | 1996-02-26 | 1999-02-23 | Minnesota Mining And Manufacturing Company | Pressure sensitive adhesives for use on low energy surfaces |
| US5837749A (en) | 1996-04-26 | 1998-11-17 | Shell Oil Company | Non-aqueous solvent free process for making UV curable adhesives and sealants from epoxidized monohydroxylated diene polymers (III) |
| US6160059A (en) | 1996-07-26 | 2000-12-12 | Cook Composites And Polymers Co. | Bulk polymerization process for preparing solid acrylic resin |
| US5852124A (en) | 1996-08-06 | 1998-12-22 | Chi Mei Corporation | Rubber-modified styrenic resin composition |
| DE19632203A1 (de) | 1996-08-09 | 1998-02-12 | Basf Ag | Haftklebstoffe mit geringen Mengen Styrol |
| US6339112B1 (en) | 1997-11-13 | 2002-01-15 | H.B. Fuller Licensing & Financing Inc. | Radiation curable compositions comprising metallocene polyolefins |
| DE19752127A1 (de) | 1997-11-25 | 1999-07-29 | Stockhausen Chem Fab Gmbh | Verfahren zur Herstellung von synthetischen Polymerisaten mit sehr niedrigem Restmonomergehalt, danach hergestellte Produkte und deren Verwendung |
| DE19824965A1 (de) | 1998-06-04 | 1999-12-09 | Metallgesellschaft Ag | Schmelzklebstoff zur Randabdichtung von Verbundglas, Verfahren zur Herstellung des Schmelzklebstoffs und seine Verwendung |
| EP0963760A1 (en) | 1998-06-09 | 1999-12-15 | The Procter & Gamble Company | Low viscosity thermoplastic compositions for moisture vapour permeable structures and the utilisation thereof in absorbent articles |
| AU6472099A (en) | 1998-10-09 | 2000-05-01 | Kraton Polymers Research B.V. | Radiation-curable adhesive |
| WO2000027942A1 (en) | 1998-11-10 | 2000-05-18 | Ato Findley, Inc. | Radiation curable pressure sensitive hot melt adhesive |
| US6294270B1 (en) | 1998-12-23 | 2001-09-25 | 3M Innovative Properties Company | Electronic circuit device comprising an epoxy-modified aromatic vinyl-conjugated diene block copolymer |
| GB9904897D0 (en) | 1999-03-03 | 1999-04-28 | Nova Chemicals Europ Limited | Polymer devlatilisation process |
| US6210517B1 (en) | 1999-04-13 | 2001-04-03 | Diversified Chemical Technologies, Inc. | Radiation-cured, non-blocking heat activated label adhesive and coatings and method for using same |
| US6429235B1 (en) | 1999-08-27 | 2002-08-06 | Cognis Corporation | Energy-curable composition for making a pressure sensitive adhesive |
| JP5135494B2 (ja) | 1999-12-22 | 2013-02-06 | 綜研化学株式会社 | アクリル系粘着テープおよびその製造方法 |
| US6502621B2 (en) | 1999-12-29 | 2003-01-07 | Styrochem Delaware, Inc. | Processes for forming styrene/methyl methacrylate copolymers |
| CA2398758C (en) | 2000-01-31 | 2011-04-19 | H.B. Fuller Licensing & Financing, Inc. | Radiation curable adhesive compositions comprising block copolymers having vinyl functionalized polydiene blocks |
| US6649259B1 (en) | 2000-02-29 | 2003-11-18 | National Starch And Chemical Investment Holding Corporation | Adhesives for thermally shrinkable films or labels |
| EP1146057A1 (en) | 2000-04-15 | 2001-10-17 | Givaudan SA | Polymeric nanoparticles including olfactive molecules |
| US6482878B1 (en) | 2000-04-21 | 2002-11-19 | National Starch And Chemical Investment Holding Corporation | Polyurethane hotmelt adhesives with acrylic copolymers and thermoplastic resins |
| EP1193289A1 (en) | 2000-10-02 | 2002-04-03 | The Procter & Gamble Company | Improved thermoplastic hydrophilic polymeric compositions for moisture vapour permeable structures |
| EP1180533A1 (en) | 2000-08-10 | 2002-02-20 | The Procter & Gamble Company | Thermoplastic hydrophilic, polymeric compostions with improved adhesive properties for moisture vapour permeable structures |
| DE10063018B4 (de) | 2000-12-16 | 2008-06-19 | Tesa Ag | Beidseitig klebende Klebfolie |
| US6461728B2 (en) | 2000-12-29 | 2002-10-08 | 3M Innovative Properties Company | Gamma radiation polymerized emulsion-based (meth)acrylate pressure sensitive adhesives and methods of making and using same |
| DE10122747A1 (de) | 2001-05-10 | 2002-11-28 | Tesa Ag | Klebfolienstreifen |
| DE10123978A1 (de) | 2001-05-17 | 2003-01-16 | Tesa Ag | Klebestreifen |
| BR0211556A (pt) | 2001-08-01 | 2004-07-13 | Fuller H B Licensing Financ | Composição respirável biodegradável fundida por calor |
| JP5046446B2 (ja) | 2001-08-02 | 2012-10-10 | 電気化学工業株式会社 | 共重合樹脂及びその製造方法 |
-
2004
- 2004-02-18 US US10/780,996 patent/US7238732B2/en not_active Expired - Fee Related
-
2005
- 2005-02-14 AT AT05723006T patent/ATE366292T1/de not_active IP Right Cessation
- 2005-02-14 DE DE602005001556T patent/DE602005001556T2/de not_active Expired - Lifetime
- 2005-02-14 JP JP2006554148A patent/JP2007523979A/ja active Pending
- 2005-02-14 WO PCT/US2005/004519 patent/WO2005080518A1/en not_active Ceased
- 2005-02-14 EP EP05723006A patent/EP1725626B1/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS543136A (en) * | 1977-06-08 | 1979-01-11 | Arakawa Chem Ind Co Ltd | Pressure-sensitive adhesives |
| JP2001055405A (ja) * | 1999-06-24 | 2001-02-27 | Wacker Polymer Systems Gmbh & Co Kg | 水性ビニルアロマート−1,3−ジエン−コポリマー分散液および該分散液から得られる再分散粉末の臭気放出を減少させるための方法、および該方法により得られた生成物の使用 |
| JP2001049200A (ja) * | 1999-08-11 | 2001-02-20 | Soken Chem & Eng Co Ltd | アクリル系粘着剤組成物、該組成物を用いた粘着テープの製造方法および粘着テープ |
| WO2001088052A1 (fr) * | 2000-05-15 | 2001-11-22 | Toagosei Co., Ltd. | Agent collant et composition adhesive |
| WO2003068280A1 (en) * | 2002-02-14 | 2003-08-21 | Lintec Corporation | Medical pressure-sensitive adhesive composition, process for producing the same, and medical tape |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006144017A (ja) * | 2004-11-24 | 2006-06-08 | Natl Starch & Chem Investment Holding Corp | 医療用途用ホトメルト接着剤 |
| JP2010074165A (ja) * | 2008-09-18 | 2010-04-02 | Tesa Se | 電子的装置のカプセル化方法 |
| US9627646B2 (en) | 2008-09-18 | 2017-04-18 | Tesa Se | Method for encapsulating an electronic arrangement |
| KR101353331B1 (ko) * | 2009-03-03 | 2014-01-17 | 히다치 막셀 가부시키가이샤 | 방사선 경화성 점착제 조성물, 그것을 사용한 다이싱용 점착 필름 및 절단편의 제조방법 |
| WO2010134521A1 (ja) * | 2009-05-22 | 2010-11-25 | 日東電工株式会社 | 紫外線硬化型粘着剤組成物、粘着剤層、粘着シートおよびその製造方法 |
| KR20180049032A (ko) * | 2015-09-08 | 2018-05-10 | 테사 소시에타스 유로파에아 | 접착제-수지-개질된 접착제 물질 |
| US10808146B2 (en) | 2015-09-08 | 2020-10-20 | Tesa Se | Adhesive-resin-modified adhesive mass |
| KR102132321B1 (ko) * | 2015-09-08 | 2020-07-09 | 테사 소시에타스 유로파에아 | 접착제-수지-개질된 접착제 물질 |
| JP2020525601A (ja) * | 2017-06-27 | 2020-08-27 | サートプラスト・テヒニシェ・クレーベベンダー・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 接着テープの製造方法 |
| JP7198784B2 (ja) | 2017-06-27 | 2023-01-04 | サートプラスト・テヒニシェ・クレーベベンダー・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 接着テープの製造方法 |
| KR20190043102A (ko) * | 2017-10-17 | 2019-04-25 | 테사 소시에타스 유로파에아 | 비닐방향족 블록 코폴리머를 기반으로 한 경화 가능한 감압 접착제 스트립 |
| KR102183036B1 (ko) | 2017-10-17 | 2020-11-25 | 테사 소시에타스 유로파에아 | 비닐방향족 블록 코폴리머를 기반으로 한 경화 가능한 감압 접착제 스트립 |
| JP2022511052A (ja) * | 2018-12-05 | 2022-01-28 | ハンワ ソリューションズ コーポレイション | ジシクロペンタジエン系樹脂、ジシクロペンタジエン系水添樹脂およびこれを含む接着樹脂組成物 |
| JP7387737B2 (ja) | 2018-12-05 | 2023-11-28 | ハンワ ソリューションズ コーポレイション | ジシクロペンタジエン系樹脂、ジシクロペンタジエン系水添樹脂およびこれを含む接着樹脂組成物 |
| US11866534B2 (en) | 2018-12-05 | 2024-01-09 | Hanwha Solutions Corporation | Dicyclopentadiene-based resin, dicyclopentadiene-based hydrogenated resin, and adhesive resin composition comprising same |
| KR102352247B1 (ko) * | 2021-03-14 | 2022-01-18 | 주식회사 엘에스이피에스파주 | 단열효과를 향상시킨 준불연 eps 내외장 다중 합치판넬 및 그 제조방법 |
| JPWO2022230027A1 (enExample) * | 2021-04-26 | 2022-11-03 | ||
| WO2022230027A1 (ja) * | 2021-04-26 | 2022-11-03 | リンテック株式会社 | エネルギー線架橋性粘着剤組成物、架橋粘着剤及び粘着シート、並びにこれらの製造方法 |
| JP7704844B2 (ja) | 2021-04-26 | 2025-07-08 | リンテック株式会社 | エネルギー線架橋性粘着剤組成物、架橋粘着剤及び粘着シート、並びにこれらの製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE602005001556T2 (de) | 2008-03-13 |
| US20050182150A1 (en) | 2005-08-18 |
| EP1725626B1 (en) | 2007-07-04 |
| EP1725626A1 (en) | 2006-11-29 |
| DE602005001556D1 (de) | 2007-08-16 |
| WO2005080518A1 (en) | 2005-09-01 |
| ATE366292T1 (de) | 2007-07-15 |
| US7238732B2 (en) | 2007-07-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7238732B2 (en) | Radiation-curable adhesive compositions | |
| US7723466B2 (en) | Aromatic-acrylate tackifier resins | |
| US7262242B2 (en) | Aromatic/acrylate tackifier resin and acrylic polymer blends | |
| JP5475439B2 (ja) | 紫外線重合性組成物類 | |
| JP4154512B2 (ja) | 粘着付与アクリル接着剤 | |
| MX2011010409A (es) | Adhesivo acrilico sensible a la presion curable con radiacion ultravioleta. | |
| MXPA97008641A (en) | Adhesives sensitive to pressure, based on acrylic, pigmented, cured with ultraviolet radiation, and method for the manufacture of mis | |
| KR101789557B1 (ko) | 이중 가교 점착부여된 감압 접착제 | |
| US9371471B2 (en) | Acrylic hot melt adhesives | |
| CA2555094C (en) | Aromatic/acrylate tackifier resin and acrylic polymer blends | |
| WO2013003198A1 (en) | Hot melt adhesive compositions that include a modified propylene-alpha-olefin polymer and exhibit low bleed through | |
| KR101980385B1 (ko) | 방사선 경화성 조성물의 제조 방법 | |
| JP7618310B1 (ja) | 無溶剤型アクリル系粘着剤組成物及び粘着シート | |
| KR20170097105A (ko) | 결합된 비닐기를 갖는 아크릴 중합체를 포함하는 전자 빔 경화성 감압성 접착제 | |
| US12163069B2 (en) | Post-polymerization functionalization of pendant functional groups | |
| JP2003277695A (ja) | Uv硬化型アクリル系粘着剤組成物 | |
| JP2023108686A (ja) | 粘着剤、ホットメルト粘着剤及びラベル | |
| PL246954B1 (pl) | Sposób wytwarzania krzemowo-(met)akrylanowego kleju samoprzylepnego o podwyższonej odporności termicznej | |
| JP2003165958A (ja) | Uv硬化型アクリル系粘着剤組成物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080214 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20080214 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20110317 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110405 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20110704 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20110711 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20111129 |