CN112210325B - Adhesive composition - Google Patents
Adhesive composition Download PDFInfo
- Publication number
- CN112210325B CN112210325B CN201910621800.8A CN201910621800A CN112210325B CN 112210325 B CN112210325 B CN 112210325B CN 201910621800 A CN201910621800 A CN 201910621800A CN 112210325 B CN112210325 B CN 112210325B
- Authority
- CN
- China
- Prior art keywords
- meth
- acrylate
- adhesive composition
- adhesive
- composition according
- 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.)
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- 230000001070 adhesive effect Effects 0.000 title claims abstract description 209
- 239000000853 adhesive Substances 0.000 title claims abstract description 208
- 239000000203 mixture Substances 0.000 title claims abstract description 107
- 230000008859 change Effects 0.000 claims abstract description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 147
- 239000000178 monomer Substances 0.000 claims description 106
- -1 2-ethylhexyl Chemical group 0.000 claims description 57
- 239000003431 cross linking reagent Substances 0.000 claims description 56
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 44
- 229920005601 base polymer Polymers 0.000 claims description 36
- 239000012948 isocyanate Substances 0.000 claims description 23
- 150000002513 isocyanates Chemical class 0.000 claims description 23
- 239000004593 Epoxy Substances 0.000 claims description 20
- 229920005989 resin Polymers 0.000 claims description 19
- 239000011347 resin Substances 0.000 claims description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 6
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 3
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 claims description 3
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 3
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 claims description 3
- 229940018557 citraconic acid Drugs 0.000 claims description 3
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 3
- 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 3
- 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 3
- 239000001530 fumaric acid Substances 0.000 claims description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical compound C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-N 0.000 claims description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 3
- 125000002960 margaryl 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])[H] 0.000 claims description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 3
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 3
- 125000001421 myristyl 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])[H] 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001196 nonadecyl 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])C([H])([H])[H] 0.000 claims description 3
- 125000001400 nonyl 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])[H] 0.000 claims description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000913 palmityl 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])[H] 0.000 claims description 3
- 125000002958 pentadecyl 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])[H] 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 229920001610 polycaprolactone Polymers 0.000 claims description 3
- 239000004632 polycaprolactone Substances 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 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 claims description 3
- 125000002889 tridecyl 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])[H] 0.000 claims description 3
- 125000002948 undecyl 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])[H] 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000004065 semiconductor Substances 0.000 abstract description 14
- 238000004519 manufacturing process Methods 0.000 abstract description 10
- 239000003292 glue Substances 0.000 abstract description 4
- 238000004806 packaging method and process Methods 0.000 abstract description 2
- 239000012790 adhesive layer Substances 0.000 description 31
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 25
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 18
- 239000000758 substrate Substances 0.000 description 17
- 238000005259 measurement Methods 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 239000013522 chelant Substances 0.000 description 11
- 238000004132 cross linking Methods 0.000 description 11
- 229920000058 polyacrylate Polymers 0.000 description 11
- 238000005538 encapsulation Methods 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000005056 polyisocyanate Substances 0.000 description 8
- 229920001228 polyisocyanate Polymers 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000003505 polymerization initiator Substances 0.000 description 7
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 239000004814 polyurethane Substances 0.000 description 5
- 229920002635 polyurethane Polymers 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- 238000004220 aggregation Methods 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 4
- 238000011109 contamination Methods 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 3
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- FKAWETHEYBZGSR-UHFFFAOYSA-N 3-methylidenepyrrolidine-2,5-dione Chemical compound C=C1CC(=O)NC1=O FKAWETHEYBZGSR-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- 239000002313 adhesive film Substances 0.000 description 2
- 239000002390 adhesive tape Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000012466 permeate Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical group O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 229920001567 vinyl ester resin Polymers 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- AURYLBASVGNSON-UHFFFAOYSA-N (2,5-dioxopyrrolidin-3-ylidene)methyl prop-2-enoate Chemical compound C=CC(=O)OC=C1CC(=O)NC1=O AURYLBASVGNSON-UHFFFAOYSA-N 0.000 description 1
- PEVRKKOYEFPFMN-UHFFFAOYSA-N 1,1,2,3,3,3-hexafluoroprop-1-ene;1,1,2,2-tetrafluoroethene Chemical compound FC(F)=C(F)F.FC(F)=C(F)C(F)(F)F PEVRKKOYEFPFMN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical class O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 1
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
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- 238000004381 surface treatment Methods 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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
- 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
-
- 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
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/062—Copolymers with monomers not covered by C09J133/06
- C09J133/066—Copolymers with monomers not covered by C09J133/06 containing -OH groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1515—Three-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
-
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- 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
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
-
- 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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Adhesive Tapes (AREA)
Abstract
The present invention relates to adhesive compositions. The invention provides an adhesive composition which can prevent the rise of adhesive force with time, has excellent stripping property and operability, and can improve packaging reliability and avoid residual glue pollution when used in the manufacture of semiconductor devices. In the adhesive composition of the present invention, the change rate y of the adhesive force calculated from the following formula (1) is 200% or less, preferably 150% or less, and y=fb/Fa (1) formula (1) indicates the change rate of the adhesive force; fa represents the adhesion of the adhesive composition at room temperature; fb represents the adhesive force of the adhesive composition heated at 100 to 180 ℃, preferably 120 to 150 ℃ for 3 to 60 minutes, preferably 5 to 30 minutes.
Description
Technical Field
The present invention relates to an adhesive composition, and more particularly, to an adhesive composition which can prevent an increase in adhesive force with time and is excellent in releasability and handleability.
Background
In recent years, CSP (Chip Size Package) technology has been attracting attention as a mounting technology of LSI. In this technology, a package in a form using only chips without using a substrate, which is represented by WLP (wafer level package ), is one of package forms of particular interest in terms of size reduction and high integration. According to the production method of WLP, a plurality of semiconductor Si wafer chips arranged in an orderly manner without using a substrate are integrally encapsulated with an encapsulation resin, and then separated into individual structures by cutting, whereby a package of a smaller size than a conventional package using a substrate can be efficiently produced.
The production process of such WLPs requires that the chips conventionally fixed on the substrate are fixed on separate supports. In addition, the fixation must be released after molding into individual packages by resin encapsulation. The support should not be permanently bonded but must be removable. From this point of view, there is a technique of using a pressure-sensitive adhesive tape as a support for temporarily fixing chips.
Disclosure of Invention
Problems to be solved by the invention
However, at the time of releasing the pressure-sensitive adhesive tape, the adhesive force becomes strong due to curing and heating of the encapsulating resin, so that there is a problem that release becomes difficult, and a residual adhesive or a release electrification occurs. When peeling becomes difficult, peeling time is prolonged, and productivity is deteriorated due to the difficulty in peeling. In the case where the residual glue occurs, the subsequent steps such as formation of an electrode cannot be performed. Further, in the case where the peeling discharge is generated, a disadvantage occurs in the subsequent step due to adhesion of dust or the like.
In addition, in the method of producing a substrate-less semiconductor package using a pressure-sensitive adhesive tape as a support for temporary fixation, the chip is not supported by the tape due to the pressure at the time of encapsulation with a resin, and is shifted from a prescribed position. Further, the pressure-sensitive adhesive tape becomes strongly adhered to the chip surface due to curing and heating of the encapsulating resin, and the package may be broken when the tape is peeled off.
The present invention has been made in view of the above circumstances, and an object thereof is to provide an adhesive composition which can prevent an increase in adhesive force with time and is excellent in peelability and handleability. The adhesive composition of the present invention can be suitably used in a pressure-sensitive adhesive tape as a support for temporarily fixing chips in the production of semiconductor devices.
Solution for solving the problem
The present inventors have conducted intensive studies to solve the above problems, and as a result, have found that the above problems can be solved by controlling the rate of change of the adhesive force of an adhesive composition within a specific range, and have completed the present invention.
Namely, the present invention is as follows.
[1] An adhesive composition having a change rate y of an adhesive force calculated by the following formula (1) of 200% or less, preferably 150% or less,
y＝Fb/Fa (1)
in the formula (1), y represents a rate of change of the adhesive force;
fa represents the adhesion of the adhesive composition at room temperature;
fb represents the adhesive force of the adhesive composition at 100 to 180 ℃, preferably 120 to 150 ℃ for 3 to 60 minutes, preferably 5 to 30 minutes.
[2] The adhesive composition according to [1], wherein the adhesive force Fa of the adhesive composition at room temperature is 0.1 to 3.0N/20mm, preferably 0.4 to 2.0N/20mm.
[3] The adhesive composition according to [1], which comprises a base polymer comprising, based on 100 parts by weight of the entire monomer components of the base polymer: 90 to 95 parts by weight of adhesive monomer, 0.1 to 5 parts by weight of hydroxyl-containing monomer and/or 1 to 5 parts by weight of carboxyl-containing monomer.
[4] The adhesive composition according to [3], which further comprises a crosslinking agent;
preferably, the crosslinking agent comprises 1 to 5 parts by weight of an isocyanate-based crosslinking agent and/or 0.1 to 2 parts by weight of an epoxy-based crosslinking agent based on 100 parts by weight of the base polymer;
preferably, the isocyanate-based crosslinking agent has an NCO content of 7 to 15% and the epoxy-based crosslinking agent has an epoxy equivalent of 80 to 120g/eq.
[5] The adhesive composition according to any one of [1] to [4], which does not contain a tackifying resin.
[6] The adhesive composition according to [3], wherein the tacky monomer comprises an alkyl (meth) acrylate having an alkyl group with 4 to 20 carbon atoms;
preferably, the alkyl (meth) acrylate having 4 to 20 carbon atoms of the alkyl group contains at least one selected from the group consisting of n-butyl (meth) acrylate, isobutyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, pentyl (meth) acrylate, isopentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isooctyl (meth) acrylate, nonyl (meth) acrylate, isononyl (meth) acrylate, decyl (meth) acrylate, isodecyl (meth) acrylate, undecyl (meth) acrylate, dodecyl (meth) acrylate, tridecyl (meth) acrylate, tetradecyl (meth) acrylate, pentadecyl (meth) acrylate, hexadecyl (meth) acrylate, heptadecyl (meth) acrylate, octadecyl (meth) acrylate, nonadecyl (meth) acrylate and eicosyl (meth) acrylate.
[7] The adhesive composition according to [3], wherein the hydroxyl group-containing monomer is contained in an amount of 2 to 4 parts by weight;
preferably, the hydroxyl-containing monomer comprises a hydroxyl-containing monomer having a primary hydroxyl group and/or a hydroxyl-containing monomer having a secondary hydroxyl group.
[8] The adhesive composition according to [3], wherein the hydroxyl group-containing monomer comprises a hydroxyl group-containing (meth) acrylate and/or an unsaturated alcohol;
preferably, the hydroxyl group-containing (meth) acrylate contains at least one selected from the group consisting of 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, hydroxyoctyl (meth) acrylate, hydroxydecyl (meth) acrylate, hydroxylauryl (meth) acrylate, 4-hydroxymethylcyclohexyl (meth) acrylate and polycaprolactone acrylate.
[9] The adhesive composition according to [3], wherein the content of the carboxyl group-containing monomer is 2 to 4 parts by weight;
preferably, the carboxyl group-containing monomer comprises an ethylenically unsaturated monocarboxylic acid and/or an ethylenically unsaturated dicarboxylic acid and anhydrides thereof;
Preferably, the ethylenically unsaturated monocarboxylic acid comprises at least one selected from the group consisting of acrylic acid, methacrylic acid, carboxyethyl (meth) acrylate, carboxypentyl (meth) acrylate, crotonic acid and isocrotonic acid;
preferably, the ethylenically unsaturated dicarboxylic acid and its anhydride comprise at least one selected from the group consisting of fumaric acid, itaconic acid, maleic acid, citraconic acid, maleic anhydride and itaconic anhydride.
[10] The adhesive composition according to any one of [1] to [9], wherein the gel fraction of the adhesive composition is 60 to 98%, preferably 70 to 95%;
the weight average molecular weight of the soluble portion of the adhesive composition is 80,000 or less, preferably 50,000 or less.
ADVANTAGEOUS EFFECTS OF INVENTION
According to the present invention, an adhesive composition which is excellent in releasability and handleability, can be provided while preventing an increase in adhesive force with time. In addition, the invention also provides an adhesive layer formed by the adhesive composition. The present invention also provides an adhesive sheet comprising the adhesive layer, which is capable of reducing chip offset from a predetermined position when used as an adhesive tape for temporarily fixing a support for chips, and which is gently releasable after use without causing residual adhesive contamination to an adherend.
Drawings
Fig. 1 is a cross-sectional view schematically showing the structure of an adhesive sheet according to the present embodiment.
Description of the reference numerals
1. Pressure-sensitive adhesive sheet
10. Substrate material
20. Adhesive layer
Detailed Description
[ adhesive composition ]
In the adhesive composition of the present invention, the change rate y of the adhesive force calculated by the following formula (1) is 200% or less, preferably 150% or less,
y＝Fb/Fa (1)
in the formula (1), y represents a rate of change of the adhesive force;
fa represents the adhesion of the adhesive composition at room temperature;
fb represents the adhesive force of the adhesive composition when heated at 100 to 180 ℃, preferably 120 to 150 ℃ for 3 to 60 minutes, preferably 5 to 30 minutes.
In the present invention, the adhesive force Fa of the adhesive composition at room temperature is preferably 3.0N/20mm or less, more preferably 2.0N/20mm or less. The lower limit value of the adhesive force Fa of the adhesive composition at room temperature is preferably 0.1N/20mm or more, more preferably 0.4N/20mm or more. By making the adhesive force Fa of the adhesive composition at room temperature within the above-described range, excellent adhesion can be achieved. When the adhesive force Fa exceeds 3.0N/20mm, peeling from the adherend is difficult, peeling workability is poor, and residual adhesive contamination is likely to occur. The adhesive force Fa of the adhesive composition at room temperature was measured as described in the following examples.
In the present invention, the adhesive composition has an adhesive force Fb of 0.1 to 6.0N/20mm, preferably 0.5 to 3.0N/20mm when heated at 100 to 180 ℃, preferably 120 to 150 ℃, more preferably 130 ℃ for 3 to 60 minutes, preferably 5 to 30 minutes, more preferably 5 minutes. By setting the adhesive force Fb within the above range, excellent adhesion reliability after time can be achieved. When the adhesive force Fb is too small or too large, peeling is caused by insufficient adhesion, peeling is difficult due to too strong adhesive force, and further, the adherend is damaged or the like due to the peeling step. The measurement of the adhesive force Fb is described in the following examples.
In the adhesive composition of the present invention, the change rate y of the adhesive force calculated by the above formula (1) is 200% or less, preferably 150% or less. When the change rate y of the adhesive force calculated by the above formula (1) is set in the above range, excellent adhesive performance can be maintained, and further, an increase in adhesive force with time can be prevented, and peelability and handleability are excellent. In addition, when the adhesive composition of the present invention is used in the production of semiconductor devices, it is possible to reduce the displacement of chips from a specified position and to peel off lightly after use without causing residual adhesive contamination to an adherend when used as a pressure-sensitive adhesive tape for temporarily fixing a support for chips. When the change rate y of the adhesive force calculated from the above formula (1) is more than 200%, the adhesive force to the adherend increases, the peeling operability is poor, and the adherend is easily broken at the time of peeling, and the residual adhesive stain is generated after peeling.
Hereinafter, each component of the adhesive composition will be described in detail.
The adhesive composition of the present invention comprises a base polymer. Preferably, the adhesive composition comprises an acrylic polymer as a base polymer.
The content of the base polymer is not particularly limited, but is preferably 60 mass% or more, more preferably 70 mass% or more, and even more preferably 80 mass% or more, based on the total amount of the adhesive composition (total weight, 100 mass%) from the viewpoint of obtaining sufficient adhesion reliability. By adjusting the content of the base polymer in the adhesive composition to be within the above range, an adhesive composition which is more excellent in structural stress relaxation property and durability and excellent in adhesion to an adherend can be provided.
The base polymer in the technology disclosed herein is preferably a polymer of the following monomer components: the monomer component contains a tacky monomer as a main monomer, and may further contain other monomers (copolymerizable monomers) having copolymerizability with the main monomer as required. The main monomer herein means a main component among monomer components constituting the base polymer, that is, a component contained in the monomer component in an amount exceeding 50% by weight.
In a preferred embodiment, the adhesive monomer comprises an alkyl (meth) acrylate. In the present specification, the term alkyl (meth) acrylate refers to alkyl acrylate and/or alkyl methacrylate.
The alkyl (meth) acrylate is preferably an alkyl (meth) acrylate having an alkyl group with 4 to 20 carbon atoms. Specific examples of the alkyl (meth) acrylate in which the alkyl group has 4 to 20 carbon atoms include, but are not particularly limited to: n-butyl (meth) acrylate, isobutyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, pentyl (meth) acrylate, isopentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isooctyl (meth) acrylate, nonyl (meth) acrylate, isononyl (meth) acrylate, decyl (meth) acrylate, isodecyl (meth) acrylate, undecyl (meth) acrylate, dodecyl (meth) acrylate, tridecyl (meth) acrylate, tetradecyl (meth) acrylate, pentadecyl (meth) acrylate, hexadecyl (meth) acrylate, heptadecyl (meth) acrylate, octadecyl (meth) acrylate, nonadecyl (meth) acrylate and eicosyl (meth) acrylate. Of these, n-Butyl Acrylate (BA) and 2-ethylhexyl acrylate (2 EHA) are preferred. The alkyl (meth) acrylate may be used alone or in combination of two or more.
The content of the tacky monomer is preferably 90 to 95 parts by weight based on 100 parts by weight of the entire monomer components of the base polymer. When the content of the tacky monomer is within the above range, excellent adhesive retention can be obtained.
As the copolymerizable monomer, a monomer having a polar group can be suitably used. Monomers having polar groups are useful for introducing crosslinking points into the base polymer or for improving the cohesion of the base polymer. The copolymerizable monomer may be used singly or in combination of 2 or more.
Specific non-limiting examples of the copolymerizable monomer include hydroxyl group-containing monomers (hydroxyl group-containing monomers), carboxyl group-containing monomers (hydroxyl group-containing monomers), sulfonic acid group-containing monomers, phosphoric acid group-containing monomers, epoxy group-containing monomers, cyano group-containing monomers, isocyanate group-containing monomers, amide group-containing monomers, monomers having a nitrogen atom-containing ring, monomers having a succinimide skeleton, maleimides, itaconimides, aminoalkyl (meth) acrylates, alkoxyalkyl (meth) acrylates, vinyl esters, vinyl ethers, aromatic vinyl compounds, olefins, and the like. Of these, at least 1 selected from hydroxyl group-containing monomers and carboxyl group-containing monomers is preferable.
The hydroxyl group-containing monomer means a monomer having at least one hydroxyl group in the molecule. In the case where the monomer component used to constitute the base polymer contains a hydroxyl group-containing monomer, that is, the base polymer contains a monomer unit derived from a hydroxyl group-containing monomer, since a secondary bond such as a hydrogen bond with an adherend is formed, the cohesive force of the base polymer (preferably an acrylic polymer) is improved, the change in adhesive force with time can be more effectively suppressed, and the adhesive residue to the adherend after peeling is less, and the adhesive composition has a higher aggregation property. In addition, when a crosslinking agent is used, a crosslinking reaction with the crosslinking agent can be effectively performed by adding a hydroxyl group-containing monomer to a raw material monomer of the base polymer, and the effect as a binder can be sufficiently exhibited. In addition, breakage of the adherend at the time of peeling operation can also be effectively prevented. The base polymer of the present embodiment may use 1 kind of hydroxyl group-containing monomer, or may use 2 or more kinds of hydroxyl group-containing monomers.
In a preferred embodiment, the hydroxyl-containing monomer preferably comprises a hydroxyl-containing monomer having a primary hydroxyl group and/or a hydroxyl-containing monomer having a secondary hydroxyl group.
In a preferred embodiment, the hydroxyl group-containing monomer comprises a hydroxyl group-containing (meth) acrylate and/or an unsaturated alcohol.
Examples of the hydroxyl group-containing (meth) acrylate include: 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, hydroxyoctyl (meth) acrylate, hydroxydecyl (meth) acrylate, hydroxylauryl (meth) acrylate, 4-hydroxymethylcyclohexyl (meth) methyl acrylate, polycaprolactone, and the like.
Examples of the unsaturated alcohol include: vinyl alcohol, allyl alcohol, and the like.
The content of the hydroxyl group-containing monomer is not particularly limited, and for example, the content of the hydroxyl group-containing monomer is 0.1 to 5 parts by weight, preferably 0.5 to 3 parts by weight, based on 100 parts by weight of the entire monomer components of the base polymer. When the content of the hydroxyl group-containing monomer is within the above range, since secondary bonds such as hydrogen bonds with an adherend are formed, the cohesive force of the base polymer (preferably, the acrylic polymer) is improved, the change in adhesive force with time can be more effectively suppressed, and the residual adhesive to the adherend after peeling is less, and the adhesive film has higher aggregation. When the content of the hydroxyl group-containing monomer is less than 0.1 part by weight, sufficient adhesion is not obtained. When the content of the hydroxyl group-containing monomer is more than 5 parts by weight, the adhesive force becomes excessive, and there is a fear that blocking is easily generated. In addition, there is a concern that breakage of the adherend is likely to occur at the time of the peeling operation.
Carboxyl group-containing monomer means a monomer having at least one carboxyl group in the molecule. By including the carboxyl group-containing monomer in the raw material monomer of the base polymer, the cohesive force of the base polymer (preferably, the acrylic polymer) is improved due to the formation of a secondary bond such as a hydrogen bond with the adherend, whereby the change in adhesive force with time can be more effectively suppressed, and the adhesive residue after peeling is less to the adherend, and the adhesive composition has higher aggregation. In addition, by containing the carboxyl group-containing monomer in the raw material monomer of the base polymer, when the crosslinking agent is used, a crosslinking reaction with the crosslinking agent can be effectively performed, the effect as the adhesive can be sufficiently exhibited, and the breakage of the adherend at the time of the peeling operation can be effectively prevented.
As carboxyl group-containing monomers, preference is given to ethylenically unsaturated monocarboxylic acids and/or ethylenically unsaturated dicarboxylic acids and their anhydrides. Examples of the ethylenically unsaturated monocarboxylic acid include: acrylic acid, methacrylic acid, carboxyethyl (meth) acrylate, carboxypentyl (meth) acrylate, crotonic acid, isocrotonic acid, and the like. Examples of the ethylenically unsaturated dicarboxylic acid and the anhydride thereof include: fumaric acid, itaconic acid, maleic acid, citraconic acid, maleic anhydride, itaconic anhydride, and the like. Among these, acrylic acid, methacrylic acid and maleic acid are preferable. The above carboxyl group-containing monomers may be used singly or in combination of any of 1 or more of 2.
The content of the carboxyl group-containing monomer is not particularly limited, and is, for example, preferably 1 to 5 parts by weight, more preferably 1 to 3 parts by weight, based on 100 parts by weight of the total monomer components of the base polymer. When the content of the carboxyl group-containing monomer in the raw material monomer is within the above range, since secondary bonds such as hydrogen bonds with the adherend are formed, the cohesive force of the base polymer (preferably the acrylic polymer) is improved, the change in adhesive force with time can be more effectively suppressed, and the residual adhesive on the adherend after peeling is less, and the aggregation is higher. When the content of the carboxyl group-containing monomer in the raw material monomer is more than 5 parts by weight, the adhesive force becomes excessive, and there is a concern that blocking is easily generated. In addition, there is a concern that breakage of the adherend is likely to occur at the time of the peeling operation. When the content of the carboxyl group-containing monomer is less than 1 part by weight, sufficient adhesion is not obtained.
Examples of the sulfonic acid group-containing monomer include: styrene sulfonic acid, allyl sulfonic acid, sodium vinyl sulfonate, 2- (meth) acrylamide-2-methylpropanesulfonic acid, (meth) acrylamide propane sulfonic acid, sulfopropyl (meth) acrylate, acryloxynaphthalene sulfonic acid, and the like.
Examples of the monomer containing a phosphate group include: 2-hydroxyethyl acryloyl phosphate, and the like.
Examples of the epoxy group-containing monomer include: glycidyl (meth) acrylate, epoxy group-containing acrylates such as 2-ethyl glycidyl (meth) acrylate, allyl glycidyl ether, glycidyl (meth) acrylate, and the like.
Examples of the cyano group-containing monomer include: acrylonitrile, methacrylonitrile, and the like.
Examples of the isocyanate group-containing monomer include: 2-isocyanatoethyl (meth) acrylate, and the like.
Examples of the amide group-containing monomer include: (meth) acrylamide; n, N-dialkyl (meth) acrylamides such as N, N-dimethyl (meth) acrylamide, N-diethyl (meth) acrylamide, N-dipropyl (meth) acrylamide, N-diisopropyl (meth) acrylamide, N-di (N-butyl) (meth) acrylamide, N-di (t-butyl) (meth) acrylamide, and the like; n-alkyl (meth) acrylamides such as N-ethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, N-butyl (meth) acrylamide, and N-N-butyl (meth) acrylamide; n-vinylcarboxylic acid amides such as N-vinylacetamide; n, N-dimethylaminopropyl (meth) acrylamide, hydroxyethyl acrylamide, N-hydroxymethyl (meth) acrylamide, N-hydroxyethyl (meth) acrylamide, N-methylolpropane (meth) acrylamide, N-methoxymethyl (meth) acrylamide, N-methoxyethyl (meth) acrylamide, N-butoxymethyl (meth) acrylamide, N- (meth) acryloylmorpholine, and the like.
Examples of the monomer having a ring containing a nitrogen atom include: n-vinyl-2-pyrrolidone, N-methyl vinyl pyrrolidone, N-vinyl pyridine, N-vinyl piperidone, N-vinyl pyrimidine, N-vinyl piperazine, N-vinyl pyrazine, N-vinyl pyrrole, N-vinyl imidazole, N-vinyl oxazole, N- (meth) acryl-2-pyrrolidone, N- (meth) acryl piperidine, N- (meth) acryl pyrrolidine, N-vinyl morpholine, N-vinyl-3-morpholinone, N-vinyl-2-caprolactam, N-vinyl-1, 3-oxazin-2-one, N-vinyl-3, 5-morpholinedione, N-vinyl pyrazole, N-vinyl isoxazole, N-vinyl thiazole, N-vinyl isothiazole, N-vinyl pyridazine, and the like.
Examples of the monomer having a succinimide skeleton include: n- (meth) acryloyloxymethylene succinimide, N- (meth) acryl-6-oxahexamethylenesuccinimide, N- (meth) acryl-8-oxahexamethylenesuccinimide, and the like.
Examples of maleimide compounds include: n-cyclohexylmaleimide, N-isopropylmaleimide, N-laurylmaleimide, N-phenylmaleimide, and the like.
Examples of the itaconimides include: n-methyl itaconimide, N-ethyl itaconimide, N-butyl itaconimide, N-octyl itaconimide, N-2-ethylhexyl itaconimide, N-cyclohexyl itaconimide, N-month Gui Jiyi itaconimide and the like.
Examples of the aminoalkyl (meth) acrylate include: aminoethyl (meth) acrylate, N-dimethylaminoethyl (meth) acrylate, N-diethylaminoethyl (meth) acrylate, t-butylaminoethyl (meth) acrylate.
Examples of the alkoxyalkyl (meth) acrylate include: methoxyethyl (meth) acrylate, ethoxyethyl (meth) acrylate, propoxyethyl (meth) acrylate, butoxyethyl (meth) acrylate, ethoxypropyl (meth) acrylate, and the like.
Examples of vinyl esters include: vinyl acetate, vinyl propionate, vinyl laurate, and the like.
Examples of vinyl ethers include: vinyl alkyl ethers such as methyl vinyl ether and ethyl vinyl ether.
Examples of the aromatic vinyl compound include: styrene, alpha-methylstyrene, vinyltoluene, chlorostyrene, chloromethylstyrene, and the like.
Examples of the olefins include: ethylene, butadiene, isoprene, isobutylene, and the like.
The method for obtaining the base polymer is not particularly limited, and various known polymerization methods such as a solution polymerization method, an emulsion polymerization method, a bulk polymerization method, a suspension polymerization method, and a photopolymerization method can be suitably used. For example, a solution polymerization method can be preferably employed. As a monomer supply method in the case of performing solution polymerization, a batch type in which all monomer raw materials are supplied at once, a continuous supply (drop wise) type, a split supply (drop wise) type, or the like can be suitably employed. The polymerization temperature in the solution polymerization may be appropriately selected depending on the types of monomers and solvents used, the types of polymerization initiators, and the like, and may be set to about 20 to 170℃for example (typically about 40 to 140 ℃).
The solvent (polymerization solvent) used in the solution polymerization may be appropriately selected from conventionally known organic solvents. For example, an aromatic compound (typically, aromatic hydrocarbon) selected from toluene and the like can be used; acetate esters such as ethyl acetate; aliphatic or alicyclic hydrocarbons such as hexane and cyclohexane; halogenated alkanes such as 1, 2-dichloroethane; lower alcohols such as isopropyl alcohol (for example, monohydric alcohols having 1 to 4 carbon atoms); ethers such as t-butyl methyl ether; any one or a mixture of two or more solvents selected from ketones such as methyl ethyl ketone.
The initiator used in the polymerization may be appropriately selected from conventionally known polymerization initiators depending on the kind of the polymerization method. For example, one or two or more azo polymerization initiators such as 2,2' -Azobisisobutyronitrile (AIBN) may be preferably used. As other examples of the polymerization initiator, there may be mentioned: persulfates such as potassium persulfate; peroxide initiators such as benzoyl peroxide and hydrogen peroxide; substituted ethane initiators such as phenyl substituted ethane; aromatic carbonyl compounds, and the like. As still other examples of the polymerization initiator, there are cited redox-type initiators obtained by combining a peroxide with a reducing agent. Such polymerization initiators may be used singly or in combination of two or more. The amount of the polymerization initiator to be used may be a usual amount, and for example, may be selected from the range of about 0.005 to about 1 part by weight (typically about 0.01 to about 1 part by weight) based on 100 parts by weight of the entire monomer components.
The weight average molecular weight (Mw) of the base polymer (suitably, the acrylic polymer) in the technology disclosed herein is not particularly limited, and may be, for example, 1,000,000 or less, preferably 400,000 or more. In general, when the weight average molecular weight Mw exceeds 1,000,000, the cohesive force tends to increase due to the effect of entanglement of the polymer, and the fluidity tends to decrease, and a sufficient adhesive area may not be obtained, and the adherend may not be fixed.
On the other hand, the weight average molecular weight (Mw) of the soluble portion of the base polymer (preferably an acrylic polymer) is preferably 80,000 or less, more preferably 5,000 or more. When the weight average molecular weight Mw of the soluble portion of the base polymer is greater than 80,000, the adhesive residue tends to occur after peeling after application heat due to insufficient cohesion of the polymer. When the weight average molecular weight Mw of the soluble portion of the base polymer is less than 5,000, the adhesive is hard due to the higher gelation of the polymer, and the adherend is not coated, resulting in infiltration of other substances.
The weight average molecular weight (Mw) herein refers to a value in terms of standard polystyrene obtained by Gel Permeation Chromatography (GPC).
As a GPC apparatus, for example, model name "HLC-8320GPC" (column: TSKgelGMH-H (S), manufactured by Tosoh Co., ltd.) may be used.
In the present invention, the adhesive composition preferably contains a crosslinking agent for the purpose of adjusting cohesion and the like. As the crosslinking agent, a conventionally used crosslinking agent can be used, and examples thereof include epoxy crosslinking agents, isocyanate crosslinking agents, aziridine crosslinking agents, melamine crosslinking agents, metal chelate crosslinking agents, and the like. These crosslinking agents may be used alone or in combination of two or more.
In a preferred embodiment, the crosslinking agent preferably comprises an epoxy-based crosslinking agent and/or an isocyanate-based crosslinking agent. By using these two crosslinking agents, a proper crosslinking reaction can be generated, the cohesive force can be sufficiently improved, good adhesion can be ensured, and breakage of an adherend at the time of peeling operation can be effectively prevented.
As the epoxy-based crosslinking agent, a compound having two or more epoxy groups in one molecule can be used without particular limitation. Preferably an epoxy-based crosslinking agent having 3 to 5 epoxy groups in one molecule. The epoxy crosslinking agent may be used singly or in combination of two or more.
Specific examples of the epoxy-based crosslinking agent include, but are not particularly limited to: n, N, N ', N' -tetraglycidyl m-xylylenediamine, 1, 3-bis (N, N-diglycidyl aminomethyl) cyclohexane, 1, 6-hexanediol diglycidyl ether, polyethylene glycol diglycidyl ether, polyglycidyl ether, and the like. Examples of the commercial products of the epoxy-based crosslinking agent include trade names "tetra-C" and "tetra-X" manufactured by Mitsubishi gas chemical corporation, trade name "EPICLONCR-5L" manufactured by DIC corporation, trade name "DENACOL EX-512" manufactured by Daikovia chemical corporation, and trade name "TEPIC-G" manufactured by Nissan chemical industry corporation.
The amount of the epoxy-based crosslinking agent used is not particularly limited, and is, for example, preferably 0.1 to 2 parts by weight based on 100 parts by weight of the base polymer.
In the embodiment containing the epoxy-based crosslinking agent, the epoxy equivalent of the epoxy-based crosslinking agent is preferably 80 to 120g/eq.
As the isocyanate-based crosslinking agent, polyfunctional isocyanates (meaning compounds having an average of two or more isocyanate groups per molecule, including compounds having an isocyanurate structure) can be preferably used. The isocyanate-based crosslinking agent may be used singly or in combination of two or more.
Examples of the polyfunctional isocyanate include aliphatic polyisocyanates, alicyclic polyisocyanates, aromatic polyisocyanates, and the like.
Specific examples of the aliphatic polyisocyanate include: 1, 2-ethylene diisocyanate; 1, 2-butanediisocyanate, 1, 3-butanediisocyanate, 1, 4-butanediisocyanate and other butanediisocyanates; hexamethylene diisocyanate such as 1, 2-hexamethylene diisocyanate, 1, 3-hexamethylene diisocyanate, 1, 4-hexamethylene diisocyanate, 1, 5-hexamethylene diisocyanate, 1, 6-hexamethylene diisocyanate and 2, 5-hexamethylene diisocyanate; 2-methyl-1, 5-pentanediisocyanate, 3-methyl-1, 5-pentanediisocyanate, lysine diisocyanate, and the like.
Specific examples of the alicyclic polyisocyanate include: isophorone diisocyanate; cyclohexyl diisocyanate such as 1, 2-cyclohexyl diisocyanate, 1, 3-cyclohexyl diisocyanate, and 1, 4-cyclohexyl diisocyanate; cyclopentyl diisocyanate such as 1, 2-cyclopentyl diisocyanate and 1, 3-cyclopentyl diisocyanate; hydrogenated xylylene diisocyanate, hydrogenated toluene diisocyanate, hydrogenated diphenylmethane diisocyanate, hydrogenated tetramethylxylylene diisocyanate, 4' -dicyclohexylmethane diisocyanate, and the like.
Specific examples of the aromatic polyisocyanate include: 2, 4-toluene diisocyanate, 2, 6-toluene diisocyanate, 4' -diphenylmethane diisocyanate, 2' -diphenylmethane diisocyanate, 4' -diphenyl ether diisocyanate, 2-nitrobiphenyl-4, 4' -diisocyanate, 2' -diphenylpropane-4, 4' -diisocyanate 3,3' -dimethyldiphenylmethane-4, 4' -diisocyanate, 4' -diphenylpropane diisocyanate, isophthalate diisocyanate, p-phenylene diisocyanate, naphthalene-1, 4-diisocyanate, naphthalene-1, 5-diisocyanate, 3' -dimethoxybiphenyl-4, 4' -diisocyanate, xylylene-1, 4-diisocyanate, xylylene-1, 3-diisocyanate, and the like.
As the preferable polyfunctional isocyanate, polyfunctional isocyanates having an average of 3 or more isocyanate groups per molecule can be exemplified. The trifunctional or higher isocyanate may be a polymer (typically a dimer or trimer) of a difunctional or higher isocyanate, a derivative (e.g., an addition reaction product of a polyol and two or more polyfunctional isocyanates), a polymer, or the like. Examples may include: dimers or trimers of diphenylmethane diisocyanate, isocyanurate forms of hexamethylene diisocyanate (isocyanurate-structured trimer adducts), reaction products of trimethylol propane and toluene diisocyanate, reaction products of trimethylol propane and hexamethylene diisocyanate, polymethylene polyphenyl isocyanates, polyether polyisocyanates, polyester polyisocyanates, and other polyfunctional isocyanates. Examples of the commercial products of the polyfunctional isocyanate include "DURANATE TPA-100" manufactured by Asahi chemical Co., ltd., and "CORONATE L" manufactured by Japanese polyurethane Industrial Co., ltd., and "CORONATE HL" manufactured by Japanese polyurethane Industrial Co., ltd., and "CORONATE HK" manufactured by Japanese polyurethane Industrial Co., ltd., and "CORONATE HX" manufactured by Japanese polyurethane Industrial Co., ltd., and "CORONATE2096" manufactured by Japanese polyurethane Industrial Co., ltd.
In the embodiment containing the isocyanate-based crosslinking agent, the isocyanate group content (NCO content) in the isocyanate-based crosslinking agent is preferably 7 to 15%.
The amount of the isocyanate-based crosslinking agent used is not particularly limited, and is, for example, preferably 1 to 5 parts by weight based on 100 parts by weight of the base polymer.
As the crosslinking agent, an isocyanate-based crosslinking agent and an epoxy-based crosslinking agent are preferably used in combination. By using the above-described amount of the isocyanate-based crosslinking agent in combination with the above-described amount of the epoxy-based crosslinking agent, both the adhesiveness to an adherend and the cohesive force can be achieved at a high level. This can realize a good retention property (cohesive force of the adhesive layer).
Examples of the aziridine crosslinking agent include: trimethylolpropane tris [3- (1-aziridinyl) propionate ], trimethylolpropane tris [3- (1- (2-methyl) aziridinylpropionate) ]. As the aziridine crosslinking agent, commercially available ones can be used. For example, chemitite series (Nippon Shokubai Co., ltd.) such as Chemitite PZ-33 and Chemitite DZ-22E can be used.
Examples of melamine-based crosslinking agents include: hexamethylol melamine, butylated melamine resins (e.g., trade name "SUPER BECKAMINE J-820-60N" available from DIC Co., ltd.), and the like.
Examples of the metal chelate crosslinking agent include: aluminum chelate compounds, titanium chelate compounds, zinc chelate compounds, zirconium chelate compounds, iron chelate compounds, cobalt chelate compounds, nickel chelate compounds, tin chelate compounds, manganese chelate compounds, chromium chelate compounds, and the like.
In order to more effectively perform the above-mentioned crosslinking reaction, a crosslinking catalyst may also be used. As the crosslinking catalyst, for example, a tin catalyst (e.g., dioctyltin dilaurate) can be preferably used. The amount of the crosslinking catalyst used is not particularly limited, and is, for example, preferably 0.0001 to 1 part by weight based on 100 parts by weight of the base polymer.
In a preferred embodiment, the adhesive composition is substantially free of tackifying resins.
In addition to the above components, the adhesive composition of the present invention may contain various additives, as necessary, which are usual in the adhesive field, such as leveling agents, crosslinking aids, plasticizers, softeners, antistatic agents, antioxidants, and the like, within a range that does not impair the effects of the present invention. Regarding such various additives, conventionally known additives can be used by a conventional method.
In a preferred embodiment, the gel fraction of the adhesive composition is preferably 60 to 98%, more preferably 70 to 95%. When the gel fraction is within the above range, excellent adhesive properties can be obtained. The gel fraction can be adjusted, for example, by the composition of the base polymer, the molecular weight, the presence or absence of the use of the crosslinking agent, the choice of the type and amount of the crosslinking agent, and the like. The gel fraction was determined as follows:
about 0.1g of an adhesive sample (weight W g1 ) With a porous polytetrafluoroethylene membrane having an average pore diameter of 0.2 μm (weight W g2 ) Is packed in a bag shape, and the kite string for the mouth (weight W g3 ) And (5) binding tightly. The packet was immersed in 50mL of ethyl acetate, held at room temperature (typically 23 ℃) for 7 days, the ethyl acetate adhered to the outer surface was wiped off the packet, the packet was dried at 130℃for 2 hours, and the weight (W) g4 ). The gel fraction was obtained by substituting each value into the following formula.
Gel fraction (%) = [ (W) g4 -W g2 -W g3 )/W g1 ]×100
[ adhesive layer ]
An adhesive layer formed using the aforementioned adhesive composition is described below. That is, the adhesive layer includes an adhesive composition having the above composition.
The method for forming the pressure-sensitive adhesive layer is not particularly limited, and may be formed by a conventionally known method. For example, a method (direct method) of forming an adhesive layer by directly applying (typically, coating) an adhesive composition onto a substrate to be described later and drying the same can be employed. In addition, a method (transfer method) of forming an adhesive layer on a surface (release surface) having releasability by applying the adhesive composition to the surface and drying the surface, and transferring the adhesive layer to a substrate described later may be employed. The release surface may be a surface of a release liner, a back surface of a substrate subjected to a release treatment, or the like. The pressure-sensitive adhesive layer disclosed herein is typically formed continuously, but is not limited to such a form, and may be formed in a regular or irregular pattern such as a dot shape or a stripe shape.
The adhesive composition may be applied by using a conventionally known coater such as a gravure roll coater, a die coater, or a bar coater. Alternatively, the adhesive composition may be applied by impregnation, curtain coating, or the like.
Drying of the adhesive composition is preferably performed under heating from the viewpoints of promoting the crosslinking reaction, improving the production efficiency, and the like. The drying temperature can be set, for example, at about 40 to 150℃and is usually preferably set at about 60 to 130 ℃. After drying the adhesive composition, aging may be further performed for the purpose of adjusting migration of components in the adhesive layer, progress of crosslinking reaction, relaxation of strain that may exist in the substrate film or the adhesive layer, and the like.
The thickness of the pressure-sensitive adhesive layer is not particularly limited, but is preferably 5 to 50 μm from the viewpoint of achieving good adhesion.
The adhesive layer has a storage modulus of 0.5X10 at 20 to 25deg.C, preferably 23 deg.C 5 ～12×10 5 Pa, preferably 2X 10 5 ～9×10 5 Pa. The storage modulus can be determined by dynamic viscoelasticity spectroscopy.
[ adhesive sheet ]
The adhesive sheet having the aforementioned adhesive layer will be described below. That is, the adhesive sheet includes the above adhesive layer.
The pressure-sensitive adhesive sheet of the present embodiment may be a pressure-sensitive adhesive sheet with a base material having the form of the pressure-sensitive adhesive layer on one side or both sides of a base material (support), or may be a pressure-sensitive adhesive sheet without a base material such as a form in which the pressure-sensitive adhesive layer is held by a release sheet (the base material having a release surface may be used). In the concept of the adhesive sheet described herein, an adhesive sheet called an adhesive tape, an adhesive label, an adhesive film, or the like may be included.
The pressure-sensitive adhesive layer is typically formed continuously, but is not limited to the above-described method, and may be formed in a regular or random pattern such as a dot pattern, a stripe pattern, or the like.
The adhesive sheet of the present embodiment may be manufactured to have a cross-sectional structure schematically shown in fig. 1, for example. As shown in fig. 1, an adhesive layer 20 is provided on one side of the substrate 10.
As the kind of the base material, a base material having heat resistance under heating conditions when encapsulated with a resin is preferably used. The resin encapsulation step typically requires a temperature of about 175 ℃. From this point, it is preferable to use a material having such heat resistance that no significant shrinkage occurs or the substrate itself does not collapse under such temperature conditions. For this reason, the material preferably has a linear thermal expansion coefficient of 0.8Xl0 at a temperature of 50 to 250 DEG C -5 ～5.6×l0 -5 /K。
Examples of the substrate are preferably at least one selected from the group consisting of polyester films, polyamide films, polyimide films, polyphenylene sulfide films, polyetherimide films, polyamide imide films, polysulfone films, polyetherketone films, polytetrafluoroethylene films, ethylene-tetrafluoroethylene copolymer films, perfluoroethylene-propylene copolymer films, polyvinylidene fluoride films, polytrifluoroethylene films, alternating copolymer films of ethylene and trifluorochloroethylene in a molar ratio of 1:1, paper substrates (such as cellophane, high quality paper and japanese paper), nonwoven fabric substrates (such as cellulose) and metal film substrates (such as aluminum foil, SUS foil and Ni foil).
The thickness of the base material is not particularly limited, but is preferably 5 to 200 μm, more preferably 10 to 150 μm, and even more preferably 20 to 100 μm, from the viewpoint of handling (handling) and workability of the adhesive sheet.
The surface of the substrate may be subjected to conventionally known surface treatments such as release treatment with a release agent such as silicone, fluorine, and long-chain alkyl, antifouling treatment, acid treatment, alkali treatment, primer treatment, corona treatment, and plasma treatment, as required.
The adhesive sheet of the present embodiment can be produced by a general production method. For example, an adhesive composition for constituting an adhesive layer is dissolved in a given solvent to prepare a coating liquid, the coating liquid is applied to a substrate so as to obtain an adhesive sheet, and then the resulting coating layer is heated and dried under given conditions.
The pressure-sensitive adhesive sheet of the present embodiment has the feature of being capable of effectively preventing an increase in adhesive force with time, being gently releasable after use, and not causing residual adhesive contamination after release. Therefore, the adhesive sheet of the present embodiment can be suitably used for, for example, component fixing use in a semiconductor device, and for example, can be suitably used as an adhesive sheet for temporarily fixing a chip in a production method of a semiconductor package. The adhesive sheet of the present embodiment can support the chip so that the chip is not transferred during the resin encapsulation step, reduce the offset of the chip from the designated position, and can be gently peeled off after use without occurrence of adhesive residue for the encapsulation resin and the chip after encapsulation.
The present invention will be described in more detail with reference to examples, but it should be noted that the present invention is not construed as being limited to the examples.
Examples
Example 1
94 parts by weight of n-Butyl Acrylate (BA) (manufactured by Zhejiang satellite), 1 part by weight of Acrylic Acid (AA), 5 parts by weight of 2-hydroxyethyl acrylate (HEA) (manufactured by Osaka organic Co., ltd.), and 60 parts by weight of ethyl acetate as a polymerization solvent were charged into a reaction vessel equipped with a stirrer, a thermometer, a nitrogen inlet pipe, and a reflux condenser, stirred at 60 to 65℃for 1 hour under a nitrogen atmosphere, and then 0.15 part of 2,2' -Azobisisobutyronitrile (AIBN) was charged as a thermal polymerization initiator, and a reaction was carried out at 60 to 65℃for 6 hours to obtain a solution of acrylic polymer A1. The Mw of the acrylic polymer A1 was 64 ten thousand.
To the acrylic polymer solution, 5 parts by weight of an isocyanate-based crosslinking agent (L75 (C), manufactured by koku corporation) and 2 parts by weight of an epoxy-based crosslinking agent (T/C, manufactured by CVC, usa) were added to 100 parts by weight of the acrylic polymer contained in the solution, and stirred and mixed to prepare an adhesive composition C1.
Examples 2 to 10
In the preparation of the adhesive composition of example 1, the types and amounts of the monomer components and the crosslinking agent were set as shown in table 1, and the adhesive compositions C2 to C10 of examples 2 to 10 were prepared in the same manner as in example 1, respectively.
Comparative examples 1 to 4
In the preparation of the adhesive composition of example 1, the types and amounts of the monomer components and the crosslinking agent were set as shown in table 2, and the adhesive compositions D1 to D4 of comparative examples 1 to 4 were prepared in the same manner as in example 1, respectively.
[ measurement of adhesive force ]
The adhesive sheets formed from the adhesive compositions of examples and comparative examples were cut to 20mm in width by 150mm in length as test pieces. The adhesion force Fa and the adhesion force Fb were measured by the following procedure using a SUS plate (SUS 430BA plate) cleaned with toluene as an adherend.
(adhesive force Fa)
The release liner covering the adhesive surface of each test piece was peeled off under a standard atmosphere of 50% RH at 23℃and a 2kg roller was reciprocated 1 time to press the exposed adhesive surface against the adherend. After the test piece thus pressed against the adherend under the above-described standard environment was left for 30 minutes, a tensile tester (product name "ten" manufactured by shimadzu corporation) was used at a tensile rate according to JIS Z0237: 300 mm/min, peel angle: peeling was performed at 180℃and the force required for the peeling (180℃peeling adhesion) (N/20 mm) was measured. The results are shown in tables 1 and 2.
(adhesive force Fb)
The test piece pressed against the adherend in the same manner as the measurement of the adhesive force Fa was heated at 130 ℃ for 5 minutes, and then left under the above-mentioned standard environment for 30 minutes, and then 180 ° peel adhesive force was measured in the same manner. The results are shown in tables 1 and 2.
[ storage modulus measurement ]
The adhesive compositions of examples and comparative examples were used to prepare adhesive layers (thickness: 50 μm) for measurement. Then, the adhesive layer was punched out to have a diameter of 7.9mm, and the resultant sample was used as a measurement sample by holding it with a parallel plate. For the above measurement samples, dynamic viscoelasticity was measured using a dynamic viscoelasticity measuring apparatus (product name "ARES" manufactured by Rheometric company) under the following conditions, and storage modulus at 23 ℃. The results are shown in tables 1 and 2.
Storage modulus measurement conditions
Measurement mode: shear mode
Temperature range: -70-150 DEG C
Heating rate: 5 ℃/min
Measuring frequency: 1Hz
[ coating Property ]
Pressure-sensitive adhesive sheets for measurement were produced from the pressure-sensitive adhesive compositions of examples and comparative examples. The surface of the semiconductor device on the side having the electrode was placed in a vacuum press (manufactured by TOWA Co., ltd.) and was placed on the adhesive layer of the adhesive sheet in order, a liquid sealing resin was injected into the cavity of the mold, and after heating at a pressure of 1MPa and 130℃for 5 minutes, the adhesive sheet was removed, and the surface of the semiconductor device on the electrode side was observed by a microscope (manufactured by KEYENCE CORPORATION, trade name: VHX-100, magnification: 200 times) for the penetration of the liquid sealing resin, and the evaluation was performed according to the following criteria.
O: the liquid encapsulation resin permeates the electrode of the semiconductor device to an extent of less than 0.1%
Delta: the quantity of the liquid encapsulation resin permeated into the electrode of the semiconductor device is 0.1-1%
X: the liquid packaging resin permeates the electrode number of the semiconductor device to be more than 1 percent
[ residual tackiness ]
Pressure-sensitive adhesive sheets for measurement were produced from the pressure-sensitive adhesive compositions of examples and comparative examples. The surface of the chip on the side having the electrode was bonded to the adhesive layer of the adhesive sheet thus produced, and the adhesive sheet was placed in an oven and heated at 150℃for 4 hours, after which the chip was peeled off from the adhesive sheet, and the bonding surface of the chip was observed with a microscope (trade name: VHX-100, magnification: 200 times), and the presence or absence of adhesive residue on the chip electrode was visually confirmed, and evaluated according to the following criteria.
O: no residual adhesive was confirmed
X: confirm the residual glue
[ immobilization ]
Pressure-sensitive adhesive sheets for measurement were produced from the pressure-sensitive adhesive compositions of examples and comparative examples. The surfaces of the chips on the electrode sides were bonded to the adhesive layer of the produced adhesive sheet in order, and after the surfaces were sealed together with a sealing resin in the cavity of the mold, whether or not the relative positions of the chips on the adhesive layer were changed was observed by a two-dimensional measuring instrument (model: "YVM-3020VT", manufactured by Guangdong Heng-Chen Seisaku Co., ltd.), and if the amount of change in position exceeded 0.005mm, the positional deviation was considered to be generated, and the evaluation was made according to the following criteria.
O: the number of positional deviations of the chips on the adhesive layer of the adhesive sheet is less than 0.1%
Delta: the number of positional deviations of the chips on the adhesive layer of the adhesive sheet is 0.1 to 1%
X: the number of positional deviations of the chips on the adhesive layer of the adhesive sheet is greater than 1%
[ Repeaability ]
Pressure-sensitive adhesive sheets for measurement were produced from the pressure-sensitive adhesive compositions of examples and comparative examples. The surfaces of the chips on the sides having the electrodes were bonded to the adhesive layer of the adhesive sheet prepared as described above, and after heating at 150℃for 4 hours, a PVC single-sided tape (trade name: SPV-224, manufactured by Nito electric Co., ltd.) was attached to the other side of the chip, and the adhesive sheet was peeled at 180℃to see whether or not the chips were transferred from the adhesive layer to the PVC single-sided tape, and the evaluation was performed according to the following criteria.
O: the number of chips remaining in the adhesive layer is less than 0.1%
Delta: the number of chips remaining in the adhesive layer is 0.1 to 1%
X: the number of chips remaining in the adhesive layer is more than 1%
[ comprehensive evaluation ]
Based on the above evaluation results, comprehensive evaluation was performed according to the following criteria.
O: excellent comprehensive effect
Delta: good comprehensive effect
X: poor overall effect
TABLE 1
TABLE 2
As can be seen from table 1, the adhesive composition of the present invention can effectively prevent the increase of adhesive force with time, and is excellent in coating property, fixing property and re-peeling property. And the surface of the adherend after stripping is basically free of residual glue, so that the yield and reliability of the product can be obviously improved.
However, in comparative examples 1 to 4, as shown in table 2, since the change rate of the adhesive force was more than 200%, peeling was difficult, and after peeling, residual adhesive was generated, fixing was poor, and the chip was liable to shift from the specified position.
Industrial applicability
The adhesive composition of the present invention can effectively prevent the increase of adhesive force with time and is excellent in peelability and handleability. In addition, the adhesive composition of the present invention can be suitably used in the production of semiconductor devices, for example, in an adhesive sheet for temporarily fixing chips in a production method of semiconductor packages, can reduce the chip from shifting from a specified position, and does not cause adhesive residue to the encapsulating resin and chips after encapsulation by light peeling after use.
Claims (18)
1. An adhesive composition characterized in that the change rate y of the adhesive force calculated by the following formula (1) is 200% or less,
y ＝ Fb/Fa (1)
In the formula (1), y represents a rate of change of the adhesive force;
fa represents the adhesion of the adhesive composition at room temperature;
fb represents the adhesive force of the adhesive composition when heated at 100 to 180 ℃ for 3 to 60 minutes,
the adhesive composition comprises a base polymer comprising, based on 100 parts by weight of the total monomer components of the base polymer: 90 to 95 weight parts of adhesive monomer, 0.5 to 3 weight parts of hydroxyl-containing monomer and 1 to 5 weight parts of carboxyl-containing monomer,
the adhesive composition further includes a crosslinking agent comprising 1 to 5 parts by weight of an isocyanate-based crosslinking agent and 0.1 to 2 parts by weight of an epoxy-based crosslinking agent based on 100 parts by weight of the base polymer.
2. The adhesive composition according to claim 1, wherein the change rate y of the adhesive force calculated from the formula (1) is 150% or less.
3. The adhesive composition according to claim 1, wherein the adhesive force Fa at room temperature of the adhesive composition is 0.1 to 3.0N/20mm.
4. The adhesive composition according to claim 3, wherein the adhesive force Fa of the adhesive composition at room temperature is 0.4 to 2.0N/20mm.
5. The adhesive composition according to claim 1, wherein the isocyanate-based crosslinking agent has an NCO content of 7 to 15% and the epoxy-based crosslinking agent has an epoxy equivalent of 80 to 120g/eq.
6. The adhesive composition according to any one of claims 1 to 5, wherein the adhesive composition is free of tackifying resins.
7. The adhesive composition according to claim 1, wherein the tacky monomer comprises an alkyl (meth) acrylate having an alkyl group with a carbon number of 4 to 20.
8. The adhesive composition according to claim 7, wherein the alkyl (meth) acrylate having 4 to 20 carbon atoms contains at least one selected from the group consisting of n-butyl (meth) acrylate, isobutyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, pentyl (meth) acrylate, isopentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isooctyl (meth) acrylate, nonyl (meth) acrylate, isononyl (meth) acrylate, decyl (meth) acrylate, isodecyl (meth) acrylate, undecyl (meth) acrylate, dodecyl (meth) acrylate, tridecyl (meth) acrylate, tetradecyl (meth) acrylate, pentadecyl (meth) acrylate, hexadecyl (meth) acrylate, heptadecyl (meth) acrylate, octadecyl (meth) acrylate, nonadecyl (meth) acrylate and eicosyl (meth) acrylate.
9. The adhesive composition according to claim 1, wherein the hydroxyl group-containing monomer is contained in an amount of 2 to 3 parts by weight.
10. The adhesive composition according to claim 1, wherein the hydroxyl-containing monomer comprises a hydroxyl-containing monomer having a primary hydroxyl group and/or a hydroxyl-containing monomer having a secondary hydroxyl group.
11. The adhesive composition according to claim 1, wherein the hydroxyl group-containing monomer comprises a hydroxyl group-containing (meth) acrylate and/or an unsaturated alcohol.
12. The adhesive composition according to claim 11, wherein the hydroxyl group-containing (meth) acrylate comprises at least one selected from the group consisting of 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, hydroxyoctyl (meth) acrylate, hydroxydecyl (meth) acrylate, hydroxylauryl (meth) acrylate, 4-hydroxymethylcyclohexyl) methyl (meth) acrylate and polycaprolactone acrylate.
13. The adhesive composition according to claim 1, wherein the content of the carboxyl group-containing monomer is 2 to 4 parts by weight.
14. The adhesive composition according to claim 1, wherein the carboxyl group containing monomer comprises an ethylenically unsaturated monocarboxylic acid and/or an ethylenically unsaturated dicarboxylic acid and anhydrides thereof.
15. The adhesive composition of claim 14, wherein the ethylenically unsaturated monocarboxylic acid comprises at least one selected from the group consisting of acrylic acid, methacrylic acid, carboxyethyl (meth) acrylate, carboxypentyl (meth) acrylate, crotonic acid, and isocrotonic acid.
16. The adhesive composition according to claim 14, wherein the ethylenically unsaturated dicarboxylic acid and its anhydride comprise at least one selected from the group consisting of fumaric acid, itaconic acid, maleic acid, citraconic acid, maleic anhydride and itaconic anhydride.
17. The adhesive composition according to any one of claims 1 to 5, wherein the adhesive composition has a gel fraction of 60 to 98%;
the soluble portion of the adhesive composition has a weight average molecular weight of 80,000 or less.
18. The adhesive composition according to claim 17, wherein the adhesive composition has a gel fraction of 70 to 95%;
the soluble portion of the adhesive composition has a weight average molecular weight of 50,000 or less.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910621800.8A CN112210325B (en) | 2019-07-10 | 2019-07-10 | Adhesive composition |
| KR1020200064698A KR20210007827A (en) | 2019-07-10 | 2020-05-29 | Adhesive composition |
| TW109121141A TWI842916B (en) | 2019-07-10 | 2020-06-22 | Adhesive composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910621800.8A CN112210325B (en) | 2019-07-10 | 2019-07-10 | Adhesive composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN112210325A CN112210325A (en) | 2021-01-12 |
| CN112210325B true CN112210325B (en) | 2023-11-17 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910621800.8A Active CN112210325B (en) | 2019-07-10 | 2019-07-10 | Adhesive composition |
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| Country | Link |
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| KR (1) | KR20210007827A (en) |
| CN (1) | CN112210325B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115404011B (en) * | 2022-10-31 | 2023-03-03 | 四川省众望科希盟科技有限公司 | Method for bonding aircraft box section and expanded polytetrafluoroethylene in medium environment |
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| CN103360974A (en) * | 2012-03-30 | 2013-10-23 | 日东电工株式会社 | Adhesive sheet |
| CN103360975A (en) * | 2012-03-30 | 2013-10-23 | 日东电工株式会社 | Pressure-sensitive adhesive sheet and optical member |
| CN103627351A (en) * | 2012-08-21 | 2014-03-12 | Dic株式会社 | Pressure sensitive adhesive composition and binder |
| CN104130726A (en) * | 2013-07-19 | 2014-11-05 | 日东电工株式会社 | Re-peeling adhesive composition, adhesive sheet, and processing method for cutting electronic component |
| CN104419339A (en) * | 2013-08-28 | 2015-03-18 | 藤森工业株式会社 | Bonding film and surface protecting film for chemical grinding |
| CN106255733A (en) * | 2014-04-16 | 2016-12-21 | 日东电工株式会社 | Adhesive sheet and optics |
| CN106916555A (en) * | 2015-11-25 | 2017-07-04 | 东洋油墨Sc控股株式会社 | Sticker, the adhesive sheet using it, Polarizer adhesive sheet and liquid crystal cells component |
-
2019
- 2019-07-10 CN CN201910621800.8A patent/CN112210325B/en active Active
-
2020
- 2020-05-29 KR KR1020200064698A patent/KR20210007827A/en unknown
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103360974A (en) * | 2012-03-30 | 2013-10-23 | 日东电工株式会社 | Adhesive sheet |
| CN103360975A (en) * | 2012-03-30 | 2013-10-23 | 日东电工株式会社 | Pressure-sensitive adhesive sheet and optical member |
| CN103627351A (en) * | 2012-08-21 | 2014-03-12 | Dic株式会社 | Pressure sensitive adhesive composition and binder |
| CN104130726A (en) * | 2013-07-19 | 2014-11-05 | 日东电工株式会社 | Re-peeling adhesive composition, adhesive sheet, and processing method for cutting electronic component |
| CN104419339A (en) * | 2013-08-28 | 2015-03-18 | 藤森工业株式会社 | Bonding film and surface protecting film for chemical grinding |
| CN106255733A (en) * | 2014-04-16 | 2016-12-21 | 日东电工株式会社 | Adhesive sheet and optics |
| CN106916555A (en) * | 2015-11-25 | 2017-07-04 | 东洋油墨Sc控股株式会社 | Sticker, the adhesive sheet using it, Polarizer adhesive sheet and liquid crystal cells component |
Also Published As
| Publication number | Publication date |
|---|---|
| CN112210325A (en) | 2021-01-12 |
| TW202111067A (en) | 2021-03-16 |
| KR20210007827A (en) | 2021-01-20 |
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