JP2619868C - - Google Patents

Info

Publication number

JP2619868C

JP2619868C JP2619868C JP 2619868 C JP2619868 C JP 2619868C JP 2619868 C JP2619868 C JP 2619868C

Authority

JP

Japan

Prior art keywords

tackifier

vinyl

phenol

substituted aromatic

terpolymer

Prior art date

1999-09-27

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.)

Expired - Lifetime

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• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 78
• 229920001897 terpolymer Polymers 0.000 claims description 40
• 238000006243 chemical reaction Methods 0.000 claims description 37
• 239000000203 mixture Substances 0.000 claims description 36
• PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 35
• 239000003054 catalyst Substances 0.000 claims description 31
• GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 claims description 26
• 239000000853 adhesive Substances 0.000 claims description 24
• 230000001070 adhesive Effects 0.000 claims description 24
• 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 20
• 125000003118 aryl group Chemical class 0.000 claims description 17
• 239000002904 solvent Substances 0.000 claims description 14
• 150000003505 terpenes Chemical class 0.000 claims description 14
• 235000007586 terpenes Nutrition 0.000 claims description 14
• 229930006725 alpha-pinene Natural products 0.000 claims description 13
• -1 monoterpene hydrocarbons Chemical class 0.000 claims description 12
• 229930003658 monoterpenes Natural products 0.000 claims description 12
• 235000002577 monoterpenes Nutrition 0.000 claims description 12
• 150000002989 phenols Chemical class 0.000 claims description 12
• 229910052739 hydrogen Inorganic materials 0.000 claims description 11
• 239000001257 hydrogen Substances 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 125000004432 carbon atoms Chemical group C* 0.000 claims description 7
• 125000000217 alkyl group Chemical group 0.000 claims description 6
• 239000004215 Carbon black (E152) Substances 0.000 claims description 5
• 238000006116 polymerization reaction Methods 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
• 239000003849 aromatic solvent Substances 0.000 description 15
• 238000000034 method Methods 0.000 description 12
• 239000000047 product Substances 0.000 description 12
• 239000000178 monomer Substances 0.000 description 10
• 229910052757 nitrogen Inorganic materials 0.000 description 10
• 238000007792 addition Methods 0.000 description 9
• 235000008733 Citrus aurantifolia Nutrition 0.000 description 8
• 235000015450 Tilia cordata Nutrition 0.000 description 8
• 240000006909 Tilia x europaea Species 0.000 description 8
• 235000011941 Tilia x europaea Nutrition 0.000 description 8
• 239000003963 antioxidant agent Substances 0.000 description 8
• 239000004571 lime Substances 0.000 description 8
• YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
• 239000012299 nitrogen atmosphere Substances 0.000 description 7
• 235000013824 polyphenols Nutrition 0.000 description 7
• 239000011541 reaction mixture Substances 0.000 description 7
• MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 6
• 230000003078 antioxidant Effects 0.000 description 6
• 229920001971 elastomer Polymers 0.000 description 6
• 229920000642 polymer Polymers 0.000 description 6
• 239000004820 Pressure-sensitive adhesive Substances 0.000 description 5
• 239000000806 elastomer Substances 0.000 description 5
• 238000001914 filtration Methods 0.000 description 5
• 239000012074 organic phase Substances 0.000 description 5
• 238000003756 stirring Methods 0.000 description 5
• 229920003048 styrene butadiene rubber Polymers 0.000 description 5
• MTAZNLWOLGHBHU-UHFFFAOYSA-N Butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 4
• 239000002174 Styrene-butadiene Substances 0.000 description 4
• BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 4
• 239000003381 stabilizer Substances 0.000 description 4
• XMGQYMWWDOXHJM-UHFFFAOYSA-N (+-)-(RS)-limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 3
• 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 3
• 229920002799 BoPET Polymers 0.000 description 3
• 239000004831 Hot glue Substances 0.000 description 3
• 239000005041 Mylar™ Substances 0.000 description 3
• 238000001816 cooling Methods 0.000 description 3
• 238000010438 heat treatment Methods 0.000 description 3
• 229930007650 limonene Natural products 0.000 description 3
• 238000002156 mixing Methods 0.000 description 3
• 150000002773 monoterpene derivatives Chemical class 0.000 description 3
• 238000003860 storage Methods 0.000 description 3
• 239000011115 styrene butadiene Substances 0.000 description 3
• XYLMUPLGERFSHI-UHFFFAOYSA-N α-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 3
• WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 2
• WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 2
• IGFHQQFPSIBGKE-UHFFFAOYSA-N 1-Nonyl-4-phenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
• JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 2
• VSKJLJHPAFKHBX-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical compound CC(=C)C=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 VSKJLJHPAFKHBX-UHFFFAOYSA-N 0.000 description 2
• GHKOFFNLGXMVNJ-UHFFFAOYSA-N Dilauryl thiodipropionate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 2
• 239000003508 Dilauryl thiodipropionate Substances 0.000 description 2
• 240000008528 Hevea brasiliensis Species 0.000 description 2
• QWVGKYWNOKOFNN-UHFFFAOYSA-N O-Cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
• 125000001931 aliphatic group Chemical group 0.000 description 2
• 230000000111 anti-oxidant Effects 0.000 description 2
• 150000001491 aromatic compounds Chemical class 0.000 description 2
• 229930006722 beta-pinene Natural products 0.000 description 2
• CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
• 235000011089 carbon dioxide Nutrition 0.000 description 2
• 239000003518 caustics Substances 0.000 description 2
• 239000000498 cooling water Substances 0.000 description 2
• 229920001577 copolymer Polymers 0.000 description 2
• 235000019304 dilauryl thiodipropionate Nutrition 0.000 description 2
• KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
• 239000007788 liquid Substances 0.000 description 2
• 229920001194 natural rubber Polymers 0.000 description 2
• 239000012188 paraffin wax Substances 0.000 description 2
• HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 2
• 239000012429 reaction media Substances 0.000 description 2
• 230000035484 reaction time Effects 0.000 description 2
• 238000005096 rolling process Methods 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
• GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-Trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 1
• HIACAHMKXQESOV-UHFFFAOYSA-N 1,2-bis(prop-1-en-2-yl)benzene Chemical compound CC(=C)C1=CC=CC=C1C(C)=C HIACAHMKXQESOV-UHFFFAOYSA-N 0.000 description 1
• JLBJTVDPSNHSKJ-UHFFFAOYSA-N 1-ethenyl-4-methylbenzene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
• JRLPEMVDPFPYPJ-UHFFFAOYSA-N 1-ethyl-4-methylbenzene Chemical compound CCC1=CC=C(C)C=C1 JRLPEMVDPFPYPJ-UHFFFAOYSA-N 0.000 description 1
• HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
• ZLCSFXXPPANWQY-UHFFFAOYSA-N 3-ethyltoluene Chemical compound CCC1=CC=CC(C)=C1 ZLCSFXXPPANWQY-UHFFFAOYSA-N 0.000 description 1
• QAPVYZRWKDXNDK-UHFFFAOYSA-N 4-octyl-N-(4-octylphenyl)aniline Chemical compound C1=CC(CCCCCCCC)=CC=C1NC1=CC=C(CCCCCCCC)C=C1 QAPVYZRWKDXNDK-UHFFFAOYSA-N 0.000 description 1
• IVSZLXZYQVIEFR-UHFFFAOYSA-N M-Xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
• 239000002313 adhesive film Substances 0.000 description 1
• 230000032683 aging Effects 0.000 description 1
• 125000005466 alkylenyl group Chemical group 0.000 description 1
• 239000008346 aqueous phase Substances 0.000 description 1
• 125000003710 aryl alkyl group Chemical group 0.000 description 1
• 229920001400 block copolymer Polymers 0.000 description 1
• 238000009835 boiling Methods 0.000 description 1
• 230000005591 charge neutralization Effects 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 150000001896 cresols Chemical class 0.000 description 1
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 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
• 235000019441 ethanol Nutrition 0.000 description 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
• 239000011521 glass Substances 0.000 description 1
• KETWBQOXTBGBBN-UHFFFAOYSA-N hex-1-enylbenzene Chemical group CCCCC=CC1=CC=CC=C1 KETWBQOXTBGBBN-UHFFFAOYSA-N 0.000 description 1
• 150000002431 hydrogen Chemical class 0.000 description 1
• 230000001939 inductive effect Effects 0.000 description 1
• 239000004615 ingredient Substances 0.000 description 1
• 239000000976 ink Substances 0.000 description 1
• 235000001510 limonene Nutrition 0.000 description 1
• 229940087305 limonene Drugs 0.000 description 1
• 238000011068 load Methods 0.000 description 1
• AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
• 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
• 239000003607 modifier Substances 0.000 description 1
• 230000001264 neutralization Effects 0.000 description 1
• 238000006386 neutralization reaction Methods 0.000 description 1
• 230000003472 neutralizing Effects 0.000 description 1
• 238000005121 nitriding Methods 0.000 description 1
• CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
• 230000003647 oxidation Effects 0.000 description 1
• 238000007254 oxidation reaction Methods 0.000 description 1
• URLKBWYHVLBVBO-UHFFFAOYSA-N p-xylene Chemical compound CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
• 239000004033 plastic Substances 0.000 description 1
• 239000004014 plasticizer Substances 0.000 description 1
• 230000000379 polymerizing Effects 0.000 description 1
• 239000005060 rubber Substances 0.000 description 1
• 125000002298 terpene group Chemical group 0.000 description 1
• WEHDCBONCFYXKK-UHFFFAOYSA-N tert-butyl 3-(4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)OC(=O)CCC1=CC=C(O)C=C1 WEHDCBONCFYXKK-UHFFFAOYSA-N 0.000 description 1
• XTXRWKRVRITETP-UHFFFAOYSA-N vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
• 239000004034 viscosity adjusting agent Substances 0.000 description 1
• 239000003039 volatile agent Substances 0.000 description 1
• 238000005406 washing Methods 0.000 description 1
• 239000001993 wax Substances 0.000 description 1
• 239000008096 xylene Substances 0.000 description 1