JPWO2015147298A1 - 粘着付与樹脂、これを含む粘接着剤組成物、ホットメルト型粘接着剤用粘着付与樹脂、ホットメルト型粘接着剤組成物、スチレン−共役ジエン系ブロック共重合体系粘接着剤組成物及びスチレン−共役ジエン系ブロック共重合体系ホットメルト型粘接着剤組成物 - Google Patents
粘着付与樹脂、これを含む粘接着剤組成物、ホットメルト型粘接着剤用粘着付与樹脂、ホットメルト型粘接着剤組成物、スチレン−共役ジエン系ブロック共重合体系粘接着剤組成物及びスチレン−共役ジエン系ブロック共重合体系ホットメルト型粘接着剤組成物 Download PDFInfo
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- JPWO2015147298A1 JPWO2015147298A1 JP2016510570A JP2016510570A JPWO2015147298A1 JP WO2015147298 A1 JPWO2015147298 A1 JP WO2015147298A1 JP 2016510570 A JP2016510570 A JP 2016510570A JP 2016510570 A JP2016510570 A JP 2016510570A JP WO2015147298 A1 JPWO2015147298 A1 JP WO2015147298A1
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- Prior art keywords
- adhesive composition
- weight
- rosin
- styrene
- tackifying resin
- Prior art date
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- Granted
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- 239000000203 mixture Substances 0.000 title claims abstract description 85
- 239000011347 resin Substances 0.000 title claims abstract description 63
- 229920005989 resin Polymers 0.000 title claims abstract description 63
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 48
- 239000000853 adhesive Substances 0.000 title claims abstract description 47
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 title claims description 47
- 239000004831 Hot glue Substances 0.000 title claims description 31
- 229920001400 block copolymer Polymers 0.000 title claims description 27
- 150000001993 dienes Chemical class 0.000 title claims description 21
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims abstract description 105
- 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 claims abstract description 105
- 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 claims abstract description 105
- 150000002148 esters Chemical class 0.000 claims abstract description 47
- -1 phosphorous acid triester Chemical class 0.000 claims abstract description 29
- 125000001424 substituent group Chemical group 0.000 claims abstract description 28
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 12
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 9
- 239000011574 phosphorus Substances 0.000 claims abstract description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- BLDLRWQLBOJPEB-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfanylphenol Chemical group OC1=CC=CC=C1SC1=CC=CC=C1O BLDLRWQLBOJPEB-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000002989 phenols Chemical class 0.000 claims abstract description 5
- 238000000354 decomposition reaction Methods 0.000 claims description 7
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- 239000007857 degradation product Substances 0.000 abstract description 16
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- 238000000034 method Methods 0.000 description 15
- 125000001931 aliphatic group Chemical group 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
- 229920000058 polyacrylate Polymers 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
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- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
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- 238000004519 manufacturing process Methods 0.000 description 6
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 230000000694 effects Effects 0.000 description 5
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- 238000005259 measurement Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 5
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
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- 239000002904 solvent Substances 0.000 description 4
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 4
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 3
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical group C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
- 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 3
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- 239000000843 powder Substances 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 125000004079 stearyl 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])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])[H] 0.000 description 3
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
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- PSCMBQDCFUMROV-UHFFFAOYSA-N OC1(CC=CC=C1)SC1(CC=CC=C1)O Chemical group OC1(CC=CC=C1)SC1(CC=CC=C1)O PSCMBQDCFUMROV-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
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- 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 description 2
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- 238000012662 bulk polymerization Methods 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
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940105990 diglycerin Drugs 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 238000012812 general test Methods 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- BQZGVMWPHXIKEQ-UHFFFAOYSA-L iron(ii) iodide Chemical compound [Fe+2].[I-].[I-] BQZGVMWPHXIKEQ-UHFFFAOYSA-L 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
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- NCPHGZWGGANCAY-UHFFFAOYSA-N methane;ruthenium Chemical compound C.[Ru] NCPHGZWGGANCAY-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
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002742 polystyrene-block-poly(ethylene/propylene) -block-polystyrene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229920001935 styrene-ethylene-butadiene-styrene Polymers 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 238000009489 vacuum treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
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- 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
- C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J153/02—Vinyl aromatic monomers and conjugated dienes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L93/00—Compositions of natural resins; Compositions of derivatives thereof
- C08L93/04—Rosin
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
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Abstract
Description
該ロジンエステル組成物が、式(1):
該ロジンエステル組成物中に含まれるロジン分解物の含有量が1.6重量%以下である
粘着付与樹脂。
(RO)2−P−O−Ph−C(CH3)2−Ph−(R:炭素数10以上の脂肪族炭化水素基、Ph:フェニル)等が挙げられる。ここで、Rとして、例えば、デシル基、ラウリル基、ステアリル基等の飽和脂肪族炭化水素基、ミリストレイル基、パルミトレイル基、オレイル基等の不飽和肪族炭化水素基等が挙げられる。
・分析装置名:HLC−8220(東ソー株式会社製)
・溶離液:THF
・サンプル濃度:0.2%
・測定温度:40℃
・カラム種:TSKgel G2000H XL、TSKgel G1000H XL (東ソー株式会社製)
・流速:1.0ml/min
・検出器:RI
撹拌装置、分水器、及び窒素導入管を備えた反応装置に精製ロジン700gを仕込み、窒素気流下で溶融撹拌し、205℃でペンタエリスリトール64g、4,4’−チオビス(6−tert−ブチル−m−クレゾール)(a)を2.8g加えた。その後、275℃まで昇温し、同温度で8時間エステル化反応を行い、トリス(2,4−ジ−tert−ブチルフェニル)フォスファイト2.2g、4,4’−イソプロピリデンジフェノール C12−15アルコールフォスファイト2.1g(b)を計4.3g添加し、4時間減圧処理を行った。その後、2時間水蒸気蒸留を行い、3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオン酸ステアリル1.8g、2、5−ジ−tert−ブチルハイドロキノン1.1g(c)を計2.9g加えて表1記載のロジンエステル1を得た。
ロジンエステル2〜32は、上記(a)、(b)及び(c)成分の種類、配合量及びロジン種を表1及び表2に記載のように変更したこと、並びにフマル酸又はアクリル酸の添加の有無以外は製造例1と同様の工程にて調製した。フマル酸又はアクリル酸を添加する場合は、205℃に昇温する途中の180℃到達時に加えた。
製造例1で得られたロジンエステル1を50重量部、市販のSBSであるKraton D1102 JSZ(スチレン−ブタジエンブロック共重合体、Kraton社製)を20重量部、PW−90(出光興産株式会社製)を30重量部、IRGANOX1010(BASF社製)を0.25重量部溶融下で混練し、ホットメルト型粘接着剤組成物を得た。このホットメルト型粘接着剤組成物を用いて下記臭気評価を行った。
粘接着剤組成物を一般的な試験管の半分まで入れ、アルミ箔でふたをし、180℃定温乾燥機に保管し、24時間加熱した。その後下記の基準で官能評価を行った。結果を表1に示す。なお、臭気評価結果はすべて相対比較によるものである。
臭気判定基準
1:ほとんど無臭
2:弱い臭気がする
3:臭気がする
4:強い臭気がする
5:強烈な臭気がする
各ロジンエステル組成物をJIS K 0071に準じて、ガードナー単位で測定した。
各ロジンエステル組成物を180℃の定温乾燥機に保管し、24時間後の色調をJIS K 0071に準じて、ガードナー単位で色調を測定することで、耐熱性を評価した。
ロジン分解物は、GPC(ゲルパーミエーションクロマトグラフ)により、算出した。図1に示すように、ロジン分解物は、ロジンエステル組成物の分子量分布を測定した際にロジン酸を示す分子量分布のピークの溶出時間より後に溶出するピークを示す物質すべてを指す。ロジンエステル組成物中のロジン分解物の含有量は、GPCにおいて全体のピーク面積に占めるロジン分解物を示すピークの面積の割合として、計算式:ロジン分解物のピーク面積/全体のピーク面積から求めた。
・分析装置名:HLC−8220(東ソー株式会社製)
・溶離液:THF
・サンプル濃度:0.2%
・測定温度:40℃
・カラム種:TSKgel G2000H XL、TSKgel G1000H XL (東ソー株式会社製)
・流速:1.0ml/min
・検出器:RI
各粘接着剤組成物の水酸基価は、JIS K 0070に準じて測定した。
・ノクラック300:4,4’−チオビス(6−tert−ブチル−m−クレゾール)、大内新興化学工業株式会社製
・IRGAFOS 168:トリス(2,4−ジ−tert−ブチルフェニル)フォスファイト、BASF社製
・アデカスタブ1500:4,4’−イソプロピリデンジフェノール C12−15アルコールフォスファイト、株式会社ADEKA製
・アデカスタブ1178:トリス(ノニルフェニル)フォスファイト、株式会社ADEKA製
・IRGANOX 1076:3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオン酸ステアリル、BASF社製
・ノクラックNS−7:2,5−ジ−tert−ブチルハイドロキノン、大内新興化学工業株式会社製
・アデカスタブAO−40:4,4’−ブチリデンビス(6−tert−ブチル−m−クレゾール)、株式会社ADEKA製
・IRGAFOS 168:トリス(2,4−ジ−tert−ブチルフェニル)フォスファイト、BASF社製
・アデカスタブ1500:4,4’−イソプロピリデンジフェノール C12−15アルコールフォスファイト、株式会社ADEKA製
・IRGANOX 1076:3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオン酸ステアリル、BASF社製
・ノクラックNS−7:2,5−ジ−tert−ブチルハイドロキノン、大内新興化学工業株式会社製
・エタノックス323:ノニルフェノール ジスルフィドオリゴマー、アルベマール社製
・ロジノックス:ポリ−tert−ブチルフェノールジスルフィド、アルケマ社製
・アデカスタブAO412−S:ビス[3−(ドデシルチオ)プロピオン酸]2,2−ビス[[3−(ドデシルチオ)−1−オキソプロピルオキシ]メチル]−1,3−プロパンジイル、株式会社ADEKA製
・アデカスタブPEP−36:3,9−ビス(2,6−ジ−tert−ブチル−4−メチルフェノキシ)−2,4,8,10−テトラオキサ−3,9−ジホスファスピロ[5.5]ウンデカン、株式会社ADEKA製
・アデカスタブTPP:トリフェニルホスファイト、株式会社ADEKA製
・IRGANOX 1010:ペンタエリスリトール テトラキス[3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート]、BASF社製
Claims (8)
- ロジンエステル組成物を含む粘着付与樹脂であって、
該ロジンエステル組成物が、式(1):
該ロジンエステル組成物中に含まれるロジン分解物の含有量が1.6重量%以下である
粘着付与樹脂。 - 水酸基価が10以下である請求項1記載の粘着付与樹脂。
- ガードナー色調が1以下である請求項1又は2記載の粘着付与樹脂。
- 請求項1〜3のいずれかに記載の粘着付与樹脂がホットメルト型粘接着剤用であるホットメルト型粘接着剤用粘着付与樹脂。
- 請求項1〜3のいずれかに記載の粘着付与樹脂を含有する粘接着剤組成物。
- 請求項4記載のホットメルト型粘接着剤用粘着付与樹脂を含有するホットメルト型粘接着剤組成物。
- 請求項1〜3のいずれかに記載の粘着付与樹脂及びスチレン−共役ジエン系ブロック共重合体を含むスチレン−共役ジエン系ブロック共重合体系粘接着剤組成物。
- 請求項4記載のホットメルト型粘接着剤用粘着付与樹脂及びスチレン−共役ジエン系ブロック共重合体を含むスチレン−共役ジエン系ブロック共重合体系ホットメルト型粘接着剤組成物。
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PCT/JP2015/059767 WO2015147298A1 (ja) | 2014-03-28 | 2015-03-27 | 粘着付与樹脂、これを含む粘接着剤組成物、ホットメルト型粘接着剤用粘着付与樹脂、ホットメルト型粘接着剤組成物、スチレン-共役ジエン系ブロック共重合体系粘接着剤組成物及びスチレン-共役ジエン系ブロック共重合体系ホットメルト型粘接着剤組成物 |
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JP6477689B2 (ja) | 2019-03-06 |
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