JP2021152122A - Film-formative silicone composition and method for producing the same - Google Patents
Film-formative silicone composition and method for producing the same Download PDFInfo
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- JP2021152122A JP2021152122A JP2020053454A JP2020053454A JP2021152122A JP 2021152122 A JP2021152122 A JP 2021152122A JP 2020053454 A JP2020053454 A JP 2020053454A JP 2020053454 A JP2020053454 A JP 2020053454A JP 2021152122 A JP2021152122 A JP 2021152122A
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- silicone composition
- component
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- silicone
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- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 155
- 239000000203 mixture Substances 0.000 title claims abstract description 133
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 25
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 56
- 239000002904 solvent Substances 0.000 claims abstract description 50
- 229920005989 resin Polymers 0.000 claims abstract description 30
- 239000011347 resin Substances 0.000 claims abstract description 30
- 238000009835 boiling Methods 0.000 claims abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 150000002430 hydrocarbons Chemical group 0.000 claims abstract description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 40
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 16
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 14
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002537 cosmetic Substances 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- XWURDDJCDLBZCW-UHFFFAOYSA-N [dimethyl(silyloxy)silyl]oxy-dimethyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[SiH3] XWURDDJCDLBZCW-UHFFFAOYSA-N 0.000 claims description 3
- 150000001451 organic peroxides Chemical class 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 230000001877 deodorizing effect Effects 0.000 claims 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 90
- 239000000853 adhesive Substances 0.000 description 27
- 230000001070 adhesive effect Effects 0.000 description 27
- -1 3Aminopropyl group Chemical group 0.000 description 22
- 239000002390 adhesive tape Substances 0.000 description 19
- 238000000034 method Methods 0.000 description 17
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 208000010201 Exanthema Diseases 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 201000005884 exanthem Diseases 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000123 paper Substances 0.000 description 5
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- 239000000758 substrate Substances 0.000 description 5
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 239000003849 aromatic solvent Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000013329 compounding Methods 0.000 description 4
- 238000006482 condensation reaction Methods 0.000 description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 230000007794 irritation Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 206010040880 Skin irritation Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 239000013464 silicone adhesive Substances 0.000 description 3
- 230000036556 skin irritation Effects 0.000 description 3
- 231100000475 skin irritation Toxicity 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 125000006038 hexenyl group Chemical group 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000011085 pressure filtration Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 150000003384 small molecules Chemical group 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- AVMSWPWPYJVYKY-UHFFFAOYSA-N 2-Methylpropyl formate Chemical compound CC(C)COC=O AVMSWPWPYJVYKY-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
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- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
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- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
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- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
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- 229950005228 bromoform Drugs 0.000 description 1
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- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
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- 230000008020 evaporation Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 210000000245 forearm Anatomy 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical group C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
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- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
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- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
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- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
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- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- IALUUOKJPBOFJL-UHFFFAOYSA-N potassium oxidosilane Chemical compound [K+].[SiH3][O-] IALUUOKJPBOFJL-UHFFFAOYSA-N 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 230000008786 sensory perception of smell Effects 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
本発明は、芳香族炭化水素溶剤を含まないシリコーン組成物、及びその製造方法、並びにその使用方法に関する。 The present invention relates to a silicone composition containing no aromatic hydrocarbon solvent, a method for producing the same, and a method for using the same.
シリコーン粘着剤を使用した粘着テープや粘着ラベルは、シリコーン粘着剤層が耐熱性、耐寒性、耐候性、電気絶縁性及び耐薬品性に優れることから、アクリル系粘着剤、ゴム系粘着剤、などの有機系粘着剤では変質・劣化してしまうような厳しい環境下で使用されている。また、種々の被着体に対しても良好に粘着することから、アクリル系粘着剤、ゴム系粘着剤、などの有機系粘着剤では粘着が困難なポリオレフィン樹脂、シリコーン樹脂、フッ素樹脂、水分を含有する表面に対して使用されている。 Adhesive tapes and adhesive labels that use silicone adhesives have excellent heat resistance, cold resistance, weather resistance, electrical insulation, and chemical resistance, so acrylic adhesives, rubber adhesives, etc. Organic adhesives are used in harsh environments where they deteriorate and deteriorate. In addition, since it adheres well to various adherends, polyolefin resins, silicone resins, fluororesins, and moisture that are difficult to adhere with organic adhesives such as acrylic adhesives and rubber adhesives can be used. Used for containing surfaces.
一方，特にシリコーンは皮膚に刺激性が少ないため，皮膚に適応することが必要な用途，たとえば、絆創膏などの人間の皮膚に貼り付ける用途や、マスカラ等の化粧料を皮膚に固定する皮膜を形成する用途でシリコーン粘着剤組成物が用いられる場合がある。 On the other hand, since silicone is less irritating to the skin, it is used for applications that need to be adapted to the skin, such as adhesive plasters and other applications that are attached to human skin, and it forms a film that fixes cosmetics such as mascara to the skin. Silicone pressure-sensitive adhesive compositions may be used for such purposes.
シリコーン粘着剤の原料の一つであるＭＱレジンは、Ｒ１ ３ＳｉＯ０．５単位およびＳｉＯ２単位を含有する。Ｒ１ ３ＳｉＯ０．５単位／ＳｉＯ２単位のモル比は例えば０．６〜１．７である（Ｒ１は炭素数１から１０の１価炭化水素基）。該ＭＱレジンは、トルエンまたはキシレンを溶剤とする反応系中で製造される。該ＭＱレジンは、溶剤を除去すると固体になるため、工業的にはトルエンまたはキシレン溶液として取り扱われる。シリコーン粘着剤を製造する場合も、ＭＱレジンはトルエンまたはキシレンなどの溶液として使用されるため、このようなＭＱレジンを含む公知のシリコーン粘着剤組成物は、芳香族炭化水素溶剤を含有する。 MQ resin is one of the raw materials of silicone pressure-sensitive adhesive contains R 1 3 SiO 0.5 units and SiO 2 units. The molar ratio of R 1 3 SiO 0.5 unit / SiO 2 unit is, for example, 0.6 to 1.7 (R 1 is a monovalent hydrocarbon group having 1 to 10 carbon atoms). The MQ resin is produced in a reaction system using toluene or xylene as a solvent. Since the MQ resin becomes a solid when the solvent is removed, it is industrially treated as a toluene or xylene solution. Since the MQ resin is also used as a solution of toluene, xylene, etc. in the production of the silicone pressure-sensitive adhesive, a known silicone pressure-sensitive adhesive composition containing such an MQ resin contains an aromatic hydrocarbon solvent.
特開２００６−１９３５９８に記載のように、芳香族系溶剤を使用して製造されたＭＱレジンを含むシリコーン組成物を用いて製造した粘着テープにおいて、芳香族溶剤の残留をなくすことは困難であった。また芳香族系溶剤を用いて製造されたＭＱレジンから加熱、減圧により溶剤を除去する方法でも微量の芳香族溶剤が残留するという問題があった。シリコーン粘着剤を用いた粘着テープや粘着ラベルを、貼付薬、絆創膏、サージカルテープ、スポーツ用テーピングテープなど、直接、皮膚に貼り付けるような用途や，直接シリコーン粘着剤を皮膚に適応し皮膜を形成する場合に、芳香族炭化水素溶剤の残留があると、皮膚への刺激が問題になる。 As described in JP-A-2006-193598, it is difficult to eliminate the residual aromatic solvent in the adhesive tape produced by using the silicone composition containing MQ resin produced by using the aromatic solvent. rice field. Further, there is a problem that a small amount of aromatic solvent remains even in the method of removing the solvent by heating and reducing the pressure from the MQ resin produced by using the aromatic solvent. Adhesive tapes and adhesive labels that use silicone adhesives can be applied directly to the skin, such as adhesives, adhesive plasters, surgical tapes, and sports taping tapes, or the silicone adhesives can be applied directly to the skin to form a film. In some cases, the residual aromatic hydrocarbon solvent makes skin irritation a problem.
そこで、芳香族炭化水素溶剤を用いずにＭＱレジンを得る方法として、特開２００６−１９３５９８には、芳香族炭化水素溶剤のかわりに脂肪族炭化水素系溶剤を用いてＭＱレジンを用いる方法が記載されている。 Therefore, as a method for obtaining an MQ resin without using an aromatic hydrocarbon solvent, Japanese Patent Application Laid-Open No. 2006-193598 describes a method in which an aliphatic hydrocarbon solvent is used instead of an aromatic hydrocarbon solvent and an MQ resin is used. Has been done.
しかし、芳香族炭化水素溶剤を用いた場合と脂肪族炭化水素溶剤を用いた場合では、生成するＭＱレジンの重合度や分子量といった組成が異なる。脂肪族系炭化水素溶剤を用いて得られるＭＱレジンを用いた場合、低分子成分が多く得られるため、得られる皮膜の強度が十分でなく、想定した皮膜形成性を得ることができない。また、芳香族炭化水素溶剤を用いることで、脂肪族炭化水素溶剤を用いる方法と比較して安価に製造することができるという利点もあるため、芳香族炭化水素溶剤を用いてＭＱレジンを製造することが望まれている。 However, the composition such as the degree of polymerization and the molecular weight of the produced MQ resin is different between the case where the aromatic hydrocarbon solvent is used and the case where the aliphatic hydrocarbon solvent is used. When an MQ resin obtained by using an aliphatic hydrocarbon solvent is used, a large amount of low molecular weight components can be obtained, so that the strength of the obtained film is not sufficient and the expected film forming property cannot be obtained. In addition, since the use of an aromatic hydrocarbon solvent has an advantage that it can be produced at a lower cost than the method using an aliphatic hydrocarbon solvent, an MQ resin is produced using an aromatic hydrocarbon solvent. Is desired.
本発明は、上記事情に鑑みなされたものであり、芳香族炭化水素溶剤を用いて製造されたＭＱレジンを含むシリコーン組成物であって、芳香族炭化水素溶剤の含有量を低減することにより、該芳香族炭化水素溶剤の残留及び揮発によりもたらされる人体への影響、特には皮膚への刺激を防ぐことを目的とする。また、本発明は、当該シリコーン組成物を簡便に提供する製造方法を提供することを目的とする。 The present invention has been made in view of the above circumstances, and is a silicone composition containing an MQ resin produced by using an aromatic hydrocarbon solvent by reducing the content of the aromatic hydrocarbon solvent. The purpose is to prevent the effects on the human body caused by the residual and volatilization of the aromatic hydrocarbon solvent, particularly irritation to the skin. Another object of the present invention is to provide a production method for easily providing the silicone composition.
本発明者は、鋭意検討を行った結果、芳香族炭化水素溶剤を用いて製造したＭＱレジンを含むシリコーン組成物において、特定の沸点を有する揮発性シリコーンを用いた下記製造方法により芳香族炭化水素溶剤の残留量を１００ｐｐｍ以下にすることができ、それにより人体への影響、特には皮膚への刺激を防ぐことができ、上記目的を達成できることを知見した。本発明は、芳香族炭化水素溶剤の残留量が１００ｐｐｍ以下であるシリコーン組成物を簡便な方法で提供する。 As a result of diligent studies, the present inventor has made an aromatic hydrocarbon by the following production method using a volatile silicone having a specific boiling point in a silicone composition containing an MQ resin produced using an aromatic hydrocarbon solvent. It has been found that the residual amount of the solvent can be reduced to 100 ppm or less, thereby preventing the influence on the human body, particularly the irritation to the skin, and the above-mentioned object can be achieved. The present invention provides a silicone composition having a residual amount of an aromatic hydrocarbon solvent of 100 ppm or less by a simple method.
すなわち本発明は、
下記（Ａ）〜（Ｃ）成分
（Ａ）末端に水酸基を有するポリジオルガノシロキサン
該（Ａ）成分と下記（Ｂ）成分の合計１００質量部に対し２０〜８０質量部
（Ｂ）Ｒ１ ３ＳｉＯ０．５単位およびＳｉＯ２単位を含有し、Ｒ１ ３ＳｉＯ０．５単位／ＳｉＯ２単位のモル比が０．６〜１．７であり、芳香族炭化水素溶剤中にて製造されたポリオルガノシロキサン樹脂（前記Ｒ１は、炭素数１〜１０の１価炭化水素基である）
前記（Ａ）成分と該（Ｂ）成分の合計１００質量部に対し８０〜２０質量部、及び
（Ｃ）常圧で１５０℃〜２００℃の範囲にある沸点を有する揮発性シリコーン
前記（Ａ）成分及び（Ｂ）成分の合計１００質量部に対して２５〜９００質量部
を含むシリコーン組成物であり、該シリコーン組成物における芳香族炭化水素の含有量が０〜１００重量ｐｐｍであることを特徴とする、前記シリコーン組成物の製造方法であって、
該製造方法は、前記（Ａ）成分、前記（Ｂ）成分、及び前記（Ｃ）成分を混合する工程と、該工程で得た生成物を減圧留去することで芳香族炭化水素含有量を０〜１００重量ｐｐｍとする工程とを含むことを特徴とする、前記製造方法を提供する。
また本発明は、該芳香族炭化水素の含有量が１００重量ｐｐｍ以下である、又は芳香族炭化水素を含まないことを特徴とするシリコーン組成物、該シリコーン組成物からなる皮膜、医療用粘着剤、及び化粧料用粘着剤を提供する。なお、本発明において芳香族炭化水素の含有量ｐｐｍは重量ｐｐｍを意味する。
That is, the present invention
Polydiorganosiloxane having a hydroxyl group at the end of components (A) below (A) to (C)
20 to 80 parts by mass (B) R 1 3 SiO 0.5 unit and SiO 2 unit are contained with respect to a total of 100 parts by mass of the component (A) and the component (B) below , and R 1 3 SiO 0.5 unit. / is the molar ratio of SiO 2 units 0.6 to 1.7, polyorganosiloxane resin prepared by an aromatic hydrocarbon solvent (the R 1 is a monovalent hydrocarbon group having 1 to 10 carbon atoms Is)
Volatile silicone having a boiling point in the range of 80 to 20 parts by mass and (C) 150 ° C. to 200 ° C. under normal pressure with respect to 100 parts by mass of the total of the component (A) and the component (B). It is a silicone composition containing 25 to 900 parts by mass with respect to a total of 100 parts by mass of the component and the component (B), and the content of aromatic hydrocarbons in the silicone composition is 0 to 100 parts by mass. This is a method for producing the silicone composition.
The production method comprises a step of mixing the component (A), the component (B), and the component (C), and distilling off the product obtained in the step under reduced pressure to reduce the aromatic hydrocarbon content. The production method is provided, which comprises a step of 0 to 100 ppm by weight.
The present invention also comprises a silicone composition having an aromatic hydrocarbon content of 100 wtppm or less or no aromatic hydrocarbon, a film composed of the silicone composition, and a medical pressure-sensitive adhesive. , And a cosmetic adhesive. In the present invention, the content ppm of aromatic hydrocarbons means ppm by weight.
本発明の製造方法によれば、芳香族炭化水素含有量を低減した、特には芳香族炭化水素を含まないシリコーン組成物を簡便に提供することができる。また、本発明のシリコーン組成物は、架橋による硬化を行わずに乾燥のみで皮膜を形成することが可能である。該シリコーン組成物は、優れた皮膜形成剤として特に人間の皮膚に適応するのに有用である。 According to the production method of the present invention, it is possible to easily provide a silicone composition having a reduced aromatic hydrocarbon content, particularly not containing an aromatic hydrocarbon. Further, the silicone composition of the present invention can form a film only by drying without curing by crosslinking. The silicone composition is useful as an excellent film-forming agent, especially for adaptation to human skin.
以下、本発明のシリコーン組成物及びその製造方法についてさらに詳しく説明する。 Hereinafter, the silicone composition of the present invention and a method for producing the same will be described in more detail.
（Ａ）成分は末端に水酸基を有するポリジオルガノシロキサンである。該ポリジオルガノシロキサンは特に制限されず、従来公知のものであればよい。例えば、下記式（１）で示される。
上記式（１）においてＲ２は、互いに独立に、置換又は非置換の、炭素数１〜１０の一価炭化水素基であり、好ましくは炭素数１〜６の一価炭化水素基である。例えば、メチル基、エチル基、プロピル基、ブチル基などのアルキル基、シクロヘキシル基などのシクロアルキル基、フェニル基、トリル基などのアリール基、ビニル基、アリル基、ヘキセニル基などのアルケニル基などが挙げられ、これらの基の炭素原子に結合した水素原子の一部または全部を他の基で置換した、３−アミノプロピル基、３，３，３−トリフロロプロピル基、３−ヒドロキシプロピル基なども例示される。特にメチル基、及びフェニル基が好ましい。 In the above formula (1), R 2 is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, preferably a monovalent hydrocarbon group having 1 to 6 carbon atoms. For example, an alkyl group such as a methyl group, an ethyl group, a propyl group or a butyl group, a cycloalkyl group such as a cyclohexyl group, an aryl group such as a phenyl group or a trill group, an alkenyl group such as a vinyl group, an allyl group or a hexenyl group may be used. 3Aminopropyl group, 3,3,3-trifluoropropyl group, 3-hydroxypropyl group, etc., in which a part or all of the hydrogen atom bonded to the carbon atom of these groups is replaced with another group. Is also exemplified. Particularly, a methyl group and a phenyl group are preferable.
該ポリジオルガノシロキサンはオイル状、又は生ゴム状であればよい。（Ａ）成分の粘度は２５℃において、オイル状のものであれば５，０００ｍＰａ・ｓ以上であるのがよく、好ましくは１０，０００ｍＰａ・ｓ以上であるのがよい。粘度が５，０００ｍＰａ・ｓ未満では凝集力（保持力）が低下する。また、生ゴム状のものであれば、３０％の濃度となるようにトルエンで溶解したときの粘度が２，０００ｍＰａ・ｓ以下が好ましい。２，０００ｍＰａ・ｓを超えると、組成物が高粘度となりすぎて製造時の撹拌が困難になる。さらに（Ａ）成分は２種以上を併用してもよい。後述する活性炭処理を行うのに好ましい範囲は、オイル状で１０，０００〜２００，０００ｍＰａ・ｓであり、特に好ましい範囲は２０，０００〜１００，０００ｍＰａ・ｓである。 The polydiorganosiloxane may be in the form of oil or raw rubber. The viscosity of the component (A) is preferably 5,000 mPa · s or more, preferably 10,000 mPa · s or more, if it is in the form of an oil at 25 ° C. If the viscosity is less than 5,000 mPa · s, the cohesive force (holding force) decreases. Further, in the case of a raw rubber-like material, the viscosity when dissolved in toluene so as to have a concentration of 30% is preferably 2,000 mPa · s or less. If it exceeds 2,000 mPa · s, the composition becomes too viscous and it becomes difficult to stir during production. Further, the component (A) may be used in combination of two or more. The preferred range for performing the activated carbon treatment described later is 10,000 to 200,000 mPa · s in oil form, and a particularly preferable range is 20,000 to 100,000 mPa · s.
（Ａ）成分は、通常、オクタメチルシクロテトラシロキサンなどのモノマーを、触媒を用いて開環重合させて製造するが、重合後は環状の低分子シロキサンを含有しているため、この環状低分子シロキサンを加熱および／または減圧下で不活性気体を通気させながら、留去したものを用いることが好ましい。 The component (A) is usually produced by ring-opening polymerization of a monomer such as octamethylcyclotetrasiloxane using a catalyst, but since it contains a cyclic low molecular weight siloxane after polymerization, this cyclic low molecular weight molecule is contained. It is preferable to use the siloxane obtained by distilling off the siloxane while aerating an inert gas under heating and / or reduced pressure.
（Ｂ）成分は、Ｒ１ ３ＳｉＯ０．５単位（Ｍ単位）およびＳｉＯ２単位（Ｑ単位）を有し、Ｒ１ ３ＳｉＯ０．５単位／ＳｉＯ２単位のモル比が０．６〜１．７、さらに好ましくは０．７〜０．９であるポリオルガノシロキサン樹脂（以下、ＭＱ樹脂ということがある）である。Ｒ１ ３ＳｉＯ０．５単位／ＳｉＯ２単位のモル比が上記下限値未満では粘着力やタックが低下することがあり、上記上限値を超えると粘着力や保持力が低下することがある。上記において、Ｒ１は、置換又は非置換の、炭素数１〜１０の、好ましくは１〜６の一価炭化水素基であり、例えば、メチル基、エチル基、プロピル基、及びブチル基などのアルキル基、シクロアルキル基、フェニル基、ビニル基、アリル基、及びヘキセニル基が挙げられる。さらに、これらの基の炭素原子に結合した水素原子の一部または全部を他の基で置換した、３−アミノプロピル基、３，３，３−トリフロロプロピル基、３−ヒドロキシプロピル基なども例示される。中でも、メチル基が好ましい。 Component (B), has a R 1 3 SiO 0.5 unit (M unit) and SiO 2 units (Q units), the molar ratio of R 1 3 SiO 0.5 units / SiO 2 units 0.6 It is a polyorganosiloxane resin (hereinafter, may be referred to as MQ resin) which is 1.7, more preferably 0.7 to 0.9. The molar ratio of R 1 3 SiO 0.5 units / SiO 2 units is less than the above lower limit may cause the adhesive strength and tackiness is lowered, exceeds the upper limit value and the adhesive strength and holding power may be lowered. In the above, R 1 is a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, such as a methyl group, an ethyl group, a propyl group, and a butyl group. Examples thereof include an alkyl group, a cycloalkyl group, a phenyl group, a vinyl group, an allyl group, and a hexenyl group. Furthermore, 3-aminopropyl group, 3,3,3-trifluoropropyl group, 3-hydroxypropyl group, etc., in which a part or all of the hydrogen atom bonded to the carbon atom of these groups is replaced with another group, etc. Illustrated. Of these, a methyl group is preferable.
（Ｂ）成分はＯＨ基を含有していてもよいが、（Ｂ）成分の質量に対してＯＨ基の含有量は０．０１〜４．０質量％が好ましい。ＯＨ基が上記下限値未満では粘着剤の凝集力が低くなることがある。また、上記上限値を超えるものは粘着剤のタックが低下する恐れがあるため好ましくない。また（Ｂ）成分は、本発明の特性を損なわない範囲で、Ｒ１ＳｉＯ１．５単位及び／又はＲ１ ２ＳｉＯ単位を（Ｂ）成分中に含有してもよい。なお（Ｂ）成分は２種以上を併用してもよい。（Ｂ）成分は、好ましくは重量平均分子量１５００〜１０，０００を有する。重量平均分子量は、例えば、ゲルパーミュエーションクロマトグラフィー（ＧＰＣ）分析（溶媒：ＴＨＦ、ポリスチレン換算、２５℃）により測定される。 The component (B) may contain an OH group, but the content of the OH group is preferably 0.01 to 4.0% by mass with respect to the mass of the component (B). If the OH group is less than the above lower limit, the cohesive force of the pressure-sensitive adhesive may be low. Further, a material exceeding the above upper limit value is not preferable because the tack of the adhesive may decrease. The component (B), within a range not to impair the characteristics of the present invention may contain R 1 SiO 1.5 units and / or R 1 2 SiO units (B) component. The component (B) may be used in combination of two or more. The component (B) preferably has a weight average molecular weight of 1500 to 10,000. The weight average molecular weight is measured, for example, by gel permeation chromatography (GPC) analysis (solvent: THF, polystyrene equivalent, 25 ° C.).
本発明において（Ｂ）成分は、芳香族炭化水素溶剤を用いて製造されたＭＱ樹脂である。特には、本発明の（Ｂ）成分は、芳香族炭化水素溶剤を用いて製造されたＭＱ樹脂であり、脂肪族炭化水素溶剤を用いずに製造されたものである。上記Ｍ単位及びＱ単位を有し、Ｍ単位／Ｑ単位のモル比０．６〜１．７である。該ＭＱ樹脂は、公知の方法に従い製造すればよい。芳香族炭化水素溶剤を用いて製造することにより、安価に目的とするポリオルガノシロキサン樹脂を得ることができる。 In the present invention, the component (B) is an MQ resin produced by using an aromatic hydrocarbon solvent. In particular, the component (B) of the present invention is an MQ resin produced using an aromatic hydrocarbon solvent, and is produced without using an aliphatic hydrocarbon solvent. It has the above M units and Q units, and has a molar ratio of M units / Q units of 0.6 to 1.7. The MQ resin may be produced according to a known method. By producing using an aromatic hydrocarbon solvent, the desired polyorganosiloxane resin can be obtained at low cost.
芳香族炭化水素溶剤を用いて上記ＭＱ樹脂を製造する方法としては、例えば、米国特許第２６７６１８２号、米国特許第２８１４６０１号、日本特許３７７２２５８号、特開昭６１−１９５１２９号、特公平６−２３２５３号、及び特公平６−３３３３５号に記載の方法などが挙げられる。例えば、特開昭６１−１９５１２９号では，塩化水素を５重量％以上含む塩酸水溶液と、式（Ｒ１Ｒ２Ｒ３Ｓｉ）２Ｏおよび式Ｒ１Ｒ２Ｒ３ＳｉＸ（式中、Ｒ１、Ｒ２、Ｒ３は水素原子および一価炭化水素基から選ばれる基、Ｘはハロゲン原子、アルコキシ基または水酸基である。）から選択される有機ケイ素化合物との混合系に、０℃〜９０℃の温度で撹拌しながら、アルキルシリケートもしくはその部分加水分解縮合物を滴下することによって、［Ｒ２Ｒ３ＳｉＯ１／２］ａ［ＳｉＯ４／２］ｂ（式中、Ｒ１、Ｒ２、Ｒ３は前述の通りであり、ａ／ｂ比率が０．２〜４である。）で示されるＭＱ樹脂を製造することができる。尚、特開昭６１−１９５１２９号記載の方法においては、塩酸とジシロキサンの混合系には反応に直接関与しない有機溶媒を、反応系を希釈するため、あるいは水相と有機相の混合を良くするために、配合させることもできる。それらの有機溶媒としては、例えば、メタノール、エタノール、イソプロパノール、アセトン、メチルエチルケトン、ベンゼン、トルエン、及びキシレンなどが挙げられる。 Examples of the method for producing the MQ resin using an aromatic hydrocarbon solvent include US Pat. No. 2,676,182, US Pat. No. 2814601, Japanese Patent No. 3772258, Japanese Patent Application Laid-Open No. 61-195129, and Japanese Patent Application Laid-Open No. 6-23253. No. and the method described in Tokusho No. 6-33335 can be mentioned. For example, in Japanese Patent Application Laid-Open No. 61-195129, a hydrochloric acid aqueous solution containing 5% by weight or more of hydrogen chloride, a formula (R 1 R 2 R 3 Si) 2 O and a formula R 1 R 2 R 3 SiX (in the formula, R 1) , R 2 and R 3 are groups selected from hydrogen atoms and monovalent hydrocarbon groups, and X is a halogen atom, alkoxy group or hydroxyl group) in a mixed system with an organic silicon compound selected from 0 ° C. to 90 ° C. [R 2 R 3 SiO 1/2 ] a [SiO 4/2 ] b (in the formula, R 1 , R 2 ) by dropping an alkyl silicate or a partially hydrolyzed condensate thereof while stirring at a temperature of ° C. , R 3 is as described above, and the MQ resin represented by the a / b ratio of 0.2 to 4) can be produced. In the method described in JP-A-61-195129, an organic solvent that is not directly involved in the reaction in the mixed system of hydrochloric acid and disiloxane is used to dilute the reaction system, or the aqueous phase and the organic phase are mixed well. It can also be blended to do so. Examples of these organic solvents include methanol, ethanol, isopropanol, acetone, methyl ethyl ketone, benzene, toluene, xylene and the like.
本発明のシリコーン組成物の製造方法において（Ｂ）ＭＱ樹脂は芳香族炭化水素溶剤に溶解されて配合される。該芳香族炭化水素溶剤とは、例えばベンゼン、トルエン、キシレン、エチルベンゼン、及びスチレンである。（Ｂ）ＭＱ樹脂の濃度は４０〜８０％が好ましく、より好ましくは５０〜７０％である。 In the method for producing a silicone composition of the present invention, the MQ resin (B) is dissolved in an aromatic hydrocarbon solvent and blended. The aromatic hydrocarbon solvent is, for example, benzene, toluene, xylene, ethylbenzene, and styrene. The concentration of the MQ resin (B) is preferably 40 to 80%, more preferably 50 to 70%.
（Ａ）成分及び（Ｂ）成分の質量比は、（Ａ）成分及び（Ｂ）成分の合計１００質量部に対して、（Ａ）成分の量が２０〜８０質量部、好ましくは３０〜７０質量部であり、（Ｂ）成分の量が８０〜２０質量部、好ましくは７０〜３０質量部であるのがよい。（Ａ）成分の量が上記下限値より低いと粘着力や保持力が低下する恐れがあり、上記上限値を超えると粘着力やタックが低下する恐れがある。 The mass ratio of the component (A) and the component (B) is such that the amount of the component (A) is 20 to 80 parts by mass, preferably 30 to 70, based on 100 parts by mass of the total of the component (A) and the component (B). It is by mass, and the amount of the component (B) is preferably 80 to 20 parts by mass, preferably 70 to 30 parts by mass. If the amount of the component (A) is lower than the above lower limit value, the adhesive strength and the holding power may decrease, and if the amount exceeds the above upper limit value, the adhesive strength and the tack may decrease.
本発明のシリコーン組成物は（Ｃ）沸点が常圧で１５０℃〜２００℃の範囲にある揮発性シリコーンを含む。該（Ｃ）揮発性シリコーンを蒸発させることで、シリコーン組成物は付着性を有する皮膜を形成する。そのため、本発明のシリコーン組成物は、通常用いられる硬化触媒である有機過酸化物硬化剤を用いて硬化する必要がない。 The silicone composition of the present invention contains (C) volatile silicone having a boiling point in the range of 150 ° C. to 200 ° C. at normal pressure. By evaporating the (C) volatile silicone, the silicone composition forms an adhesive film. Therefore, the silicone composition of the present invention does not need to be cured using an organic peroxide curing agent which is a commonly used curing catalyst.
（Ｃ）成分は沸点が常圧で１５０℃〜２００℃の範囲にある揮発性シリコーンである。当該沸点は一般的な芳香族炭化水素溶剤の沸点よりも高い。そのため、（Ａ）成分及び（Ｂ）成分と（Ｃ）成分との混合物を減圧留去することで、（Ｂ）成分に付随して含まれる残留芳香族炭化水素溶剤を揮発性シリコーンで置換し、組成物中に含まれる芳香族炭化水素を除去又は量を低減することができる。すなわち、シリコーン組成物中に含まれる芳香族炭化水素量を１００ｐｐｍ以下、好ましくは５０ｐｐｍ以下にすることができる。下限値は０ｐｐｍ以上であるのが好ましく、０．１ｐｐｍ以上、５ｐｍｍ以上であってもよいが、少なければ少ないほどよい。シリコーン組成物中における（Ｃ）成分の量は（Ａ）成分及び（Ｂ）成分の合計１００質量部に対して２５〜９００質量部、好ましくは３０〜７００質量部、より好ましくは４０〜５００質量部であればよい。減圧留去により揮発性シリコーンとともに芳香族炭化水素を留去し、その後留去した量に相当する量の揮発性シリコーンを添加することにより、固形分３０〜８０％を有するシリコーン組成物を得るのが好ましい。 The component (C) is a volatile silicone having a boiling point in the range of 150 ° C. to 200 ° C. at normal pressure. The boiling point is higher than the boiling point of a general aromatic hydrocarbon solvent. Therefore, by distilling off the component (A) and the mixture of the component (B) and the component (C) under reduced pressure, the residual aromatic hydrocarbon solvent contained in the component (B) is replaced with volatile silicone. , Aromatic hydrocarbons contained in the composition can be removed or the amount can be reduced. That is, the amount of aromatic hydrocarbons contained in the silicone composition can be 100 ppm or less, preferably 50 ppm or less. The lower limit is preferably 0 ppm or more, and may be 0.1 ppm or more and 5 pmm or more, but the smaller the value, the better. The amount of the component (C) in the silicone composition is 25 to 900 parts by mass, preferably 30 to 700 parts by mass, and more preferably 40 to 500 parts by mass with respect to 100 parts by mass of the total of the components (A) and (B). It may be a department. Aromatic hydrocarbons are distilled off together with volatile silicone by distillation under reduced pressure, and then a silicone composition having a solid content of 30 to 80% is obtained by adding an amount of volatile silicone corresponding to the amount distilled off. Is preferable.
揮発性シリコーンの沸点が上記上限値超では、皮膜形成の際の蒸発速度が遅く皮膜とならない場合がある。沸点が上記下限値未満では、芳香族炭化水素溶剤を溶剤置換できないため不適である。当該揮発性シリコーンとしては、例えば、オクタメチルトリシロキサン、及びヘプタメチルテトラシロキサンが用いられる。 If the boiling point of the volatile silicone exceeds the above upper limit, the evaporation rate at the time of film formation may be slow and the film may not be formed. If the boiling point is less than the above lower limit, the aromatic hydrocarbon solvent cannot be replaced with a solvent, which is unsuitable. As the volatile silicone, for example, octamethyltrisiloxane and heptamethyltetrasiloxane are used.
また本発明のシリコーン組成物には、その他の溶剤として、ヘキサン、ヘプタン、オクタン、イソオクタン、イソパラフィンなどの脂肪族炭化水素系溶剤、アセトン、メチルエチルケトン、２−ペンタノン、３−ペンタノン、２−ヘキサノン、２−ヘプタノン、４−ヘプタノン、メチルイソブチルケトン、ジイソブチルケトン、及びシクロヘキサノンなどのケトン系溶剤、ギ酸エチル、ギ酸プロピル、ギ酸ブチル、ギ酸イソブチル、ギ酸ペンチル、酢酸エチル、酢酸プロピル、酢酸イソプロピル、酢酸ブチルなどのエステル系溶剤、ジエチルエーテル、ジプロピルエーテル、ジイソプロピルエーテル、ジブチルエーテル、などのエーテル系溶剤、エタノール、イソプロパノール、ブタノール、イソブタノール、などのアルコール系溶剤、またはこれらの混合溶剤などを含んでもよい。但し、ベンゼン、トルエン、キシレン、エチルベンゼン、及びスチレン等の芳香族炭化水素溶剤は含まない。さらに、ジクロロメタン、クロロホルム、四塩化炭素、トリクロロエタン、ブロモホルム、フロン類などのハロゲン系溶剤も含まないのがよい。該その他の溶剤の配合量は特に制限されるものでないが、例えば、シリコーン組成物１００質量部に対して２５〜２００質量部、好ましくは４０〜１５０質量部であればよい。 Further, in the silicone composition of the present invention, as other solvents, aliphatic hydrocarbon solvents such as hexane, heptane, octane, isooctane and isoparaffin, acetone, methyl ethyl ketone, 2-pentanone, 3-pentanone, 2-hexanone, 2 -Ketone solvents such as heptanone, 4-heptanone, methylisobutylketone, diisobutylketone, and cyclohexanone, ethyl formate, propyl formate, butyl formate, isobutyl formate, pentyl formate, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, etc. It may contain an ester solvent, an ether solvent such as diethyl ether, dipropyl ether, diisopropyl ether, dibutyl ether, an alcohol solvent such as ethanol, isopropanol, butanol, isobutanol, or a mixed solvent thereof. However, aromatic hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, and styrene are not included. Furthermore, it is preferable that halogen-based solvents such as dichloromethane, chloroform, carbon tetrachloride, trichloroethane, bromoform, and chlorofluorocarbons are not contained. The blending amount of the other solvent is not particularly limited, but may be, for example, 25 to 200 parts by mass, preferably 40 to 150 parts by mass with respect to 100 parts by mass of the silicone composition.
本発明のシリコーン組成物は（Ａ）成分、芳香族炭化水素溶剤にて製造された（Ｂ）成分、及び（Ｃ）成分の一部または全部を混合溶解し、該混合物を減圧留去して、シリコーン組成物に含まれる残留芳香族炭化水素溶剤を除去することにより製造される。減圧留去の条件は、例えば３０〜１００℃、好ましくは４０℃〜７０℃の範囲にある温度、及び、１３．３〜１３３．３ｈＰａの範囲にある圧力であればよい。上述した通り、減圧留去により揮発性シリコーンとともに芳香族炭化水素溶剤を留去し、その後留去した量に相当する量の揮発性シリコーンを添加することにより、固形分３０〜８０％を有するシリコーン組成物を得る。得られた組成物は、通常、不揮発分の濃度を、例えば３０〜８０質量％に調整し、保管、輸送のために容器に充填される。粘着テープ、粘着シート、粘着ラベルなどを製造する際は、必要に応じて溶剤で希釈し、後に示す種々の基材に塗工される。また直接皮膚に塗り広げても良い。 In the silicone composition of the present invention, a component (A), a component (B) prepared with an aromatic hydrocarbon solvent, and a part or all of the component (C) are mixed and dissolved, and the mixture is distilled off under reduced pressure. , Manufactured by removing the residual aromatic hydrocarbon solvent contained in the silicone composition. The conditions for distillation under reduced pressure may be, for example, a temperature in the range of 30 to 100 ° C., preferably 40 ° C. to 70 ° C., and a pressure in the range of 13.3 to 133.3 hPa. As described above, the aromatic hydrocarbon solvent is distilled off together with the volatile silicone by distillation under reduced pressure, and then a silicone having a solid content of 30 to 80% is added by adding an amount of volatile silicone corresponding to the amount of the distilled silicone. Obtain the composition. The obtained composition is usually adjusted in concentration of non-volatile content to, for example, 30 to 80% by mass, and filled in a container for storage and transportation. When producing an adhesive tape, an adhesive sheet, an adhesive label, etc., it is diluted with a solvent, if necessary, and coated on various substrates shown later. It may also be spread directly on the skin.
本発明のシリコーン組成物は、（Ａ）成分、（Ｂ）成分及び（Ｃ）成分の一部または全部を、好ましくは塩基触媒存在下で、室温または加熱下で混合して製造される。好ましくは、該塩基触媒存在下で縮合反応させるのがよい。従って、本発明のシリコーン組成物の好ましい一態様としては、上記（Ａ）成分と（Ｂ）成分との縮合反応物を含む。当該混合及び縮合反応後、必要に応じて揮発性シリコーンをさらに添加し、減圧留去することにより、シリコーン組成物に含まれる芳香族炭化水素を除去することができる。混合及び反応温度は、例えば２０〜１５０℃とすることができる。通常は、室温ないし有機溶剤の還流温度でおこなえばよい。時間は特に限定されないが、０．５時間〜１０時間、好ましくは１時間〜６時間とすればよい。 The silicone composition of the present invention is produced by mixing a part or all of the component (A), the component (B) and the component (C), preferably in the presence of a base catalyst, at room temperature or under heating. Preferably, the condensation reaction is carried out in the presence of the base catalyst. Therefore, a preferred embodiment of the silicone composition of the present invention includes a condensation reaction product of the above-mentioned component (A) and component (B). After the mixing and condensation reaction, if necessary, volatile silicone is further added and distilled off under reduced pressure to remove aromatic hydrocarbons contained in the silicone composition. The mixing and reaction temperatures can be, for example, 20-150 ° C. Usually, it may be carried out at room temperature or the reflux temperature of the organic solvent. The time is not particularly limited, but may be 0.5 hours to 10 hours, preferably 1 hour to 6 hours.
塩基触媒としては、水酸化リチウム、水酸化ナトリウム、水酸化カリウム、水酸化カルシウムなどの金属水酸化物、炭酸ナトリウム、炭酸カリウムなどの炭酸塩、炭酸水素ナトリウムなどの炭酸水素塩、ナトリウムメトキシド、カリウムブトキシドなどの金属アルコキシド、ブチルリチウムなどの有機金属、カリウムシラノレート、アンモニアガス、アンモニア水、メチルアミン、トリメチルアミン、トリエチルアミンなどの窒素化合物などがあげられる。中でも、アンモニアガス、及びアンモニア水が好ましい。 Examples of the base catalyst include metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, carbonates such as sodium carbonate and potassium carbonate, hydrogen carbonates such as sodium hydrogencarbonate, and sodium alkoxide. Examples thereof include metal alkoxides such as potassium butoxide, organic metals such as butyl lithium, potassium silanolate, ammonia gas, aqueous ammonia, nitrogen compounds such as methylamine, trimethylamine and triethylamine. Of these, ammonia gas and ammonia water are preferable.
上記縮合反応後、必要に応じて、塩基触媒を中和する中和剤を添加しても良い。中和剤としては、二酸化炭素などの酸性ガス、酢酸、オクチル酸、クエン酸などの有機酸、リン酸などの鉱酸、などが挙げられる。 After the condensation reaction, a neutralizing agent that neutralizes the base catalyst may be added, if necessary. Examples of the neutralizing agent include acid gases such as carbon dioxide, organic acids such as acetic acid, octyl acid and citric acid, and mineral acids such as phosphoric acid.
シリコーン組成物は、通常、保管、輸送のために容器に充填される。粘着テープ、粘着シート、粘着ラベルなどを製造する際は、シリコーン組成物を必要に応じて、芳香族炭化水素溶剤を除く有機溶剤で希釈し、後に示す種々の基材に塗工される。本発明のシリコーン組成物は、乾燥することで皮膜を形成することができる。 Silicone compositions are usually filled in containers for storage and transportation. When producing an adhesive tape, an adhesive sheet, an adhesive label, etc., the silicone composition is diluted with an organic solvent other than an aromatic hydrocarbon solvent, if necessary, and coated on various substrates described later. The silicone composition of the present invention can form a film by drying.
通常、芳香族炭化水素溶剤を用いて製造された（Ｂ）成分を含むシリコーン組成物から形成された皮膜を有する粘着テープには、芳香族炭化水素が残留する。本発明は、シリコーン組成物に上述した特定沸点を有する揮発性シリコーンを添加して減圧留去を行うことで、シリコーン組成物中の芳香族炭化水素量を１００ｐｐｍ以下とすることができる。また、シリコーン組成物から皮膜を形成する際に加熱することにより、得られる皮膜中の芳香族炭化水素の量を１０ｐｐｍ以下とすることができる。 Usually, aromatic hydrocarbons remain on the adhesive tape having a film formed from the silicone composition containing the component (B) produced by using an aromatic hydrocarbon solvent. According to the present invention, the amount of aromatic hydrocarbons in the silicone composition can be reduced to 100 ppm or less by adding the above-mentioned volatile silicone having a specific boiling point to the silicone composition and distilling off under reduced pressure. Further, by heating when forming a film from the silicone composition, the amount of aromatic hydrocarbons in the obtained film can be reduced to 10 ppm or less.
ここで、シリコーン組成物から芳香族炭化水素を留去すると異臭が確認される。当該異臭は（Ｂ）オルガノポリシロキサン樹脂中に含まれる低分子成分であると推察される。芳香族炭化水素が多く残存するシリコーン組成物では、芳香族炭化水素の臭いが強いため、低分子成分の異臭は確認できない。しかし、本発明の方法により芳香族炭化水素を除去又は低減したシリコーン組成物では、低分子成分由来の異臭が確認される。当該シリコーン組成物を皮膚に適応する場合には、臭いを低減する必要がある。そのため本発明の製造方法は、シリコーン組成物を活性炭で処理する工程をさらに含むのが好ましい。シリコーン組成物を活性炭で処理することにより異臭を取り除くことができる。 Here, when the aromatic hydrocarbon is distilled off from the silicone composition, an offensive odor is confirmed. It is presumed that the offensive odor is a small molecule component contained in the (B) organopolysiloxane resin. In the silicone composition in which a large amount of aromatic hydrocarbons remains, the odor of aromatic hydrocarbons is strong, so that no offensive odor of low molecular weight components can be confirmed. However, in the silicone composition from which aromatic hydrocarbons have been removed or reduced by the method of the present invention, an offensive odor derived from a small molecule component is confirmed. When applying the silicone composition to the skin, it is necessary to reduce the odor. Therefore, the production method of the present invention preferably further includes a step of treating the silicone composition with activated carbon. The offensive odor can be removed by treating the silicone composition with activated carbon.
シリコーン組成物を活性炭処理する方法としては、シリコーン組成物に活性炭を加え、常温で撹拌したのち、活性炭をろ過等で除去する方法、シリコーン組成物を活性炭フィルターに通して処理する方法がある。 As a method for treating the silicone composition with activated carbon, there are a method in which activated carbon is added to the silicone composition, the mixture is stirred at room temperature, and then the activated carbon is removed by filtration or the like, or the silicone composition is treated by passing it through an activated carbon filter.
活性炭処理をする際、シリコーン組成物の粘度が高いと、ろ過速度、あるいはフィルター通過速度が遅すぎて工業的に生産することが困難となる場合がある。そのため、シリコーン組成物の粘度を一定以下に抑えることで、シリコーン組成物の生産性向上が可能となる。 When the activated carbon treatment is performed, if the viscosity of the silicone composition is high, the filtration rate or the filter passing rate may be too slow to produce industrially. Therefore, by suppressing the viscosity of the silicone composition to a certain level or less, the productivity of the silicone composition can be improved.
シリコーン組成物の粘度を下げるには、シリコーン組成物に配合する（Ａ）成分の粘度を所定の範囲内に抑える、あるいは、シリコーン組成物に含まれるシリコーン成分量を下げるという方法がある。活性炭処理を行うのに好ましい（Ａ）成分の粘度範囲は、５，０００ｍＰａ・ｓ以上であるのがよく、特には１０，０００ｍＰａ・ｓ以上が好ましく、１０，０００〜２００，０００ｍＰａ・ｓであるのがよく、特に好ましい範囲は２０，０００〜１００，０００ｍＰａ・ｓである。粘度が上記下限値未満では凝集力（保持力）が低下する恐れがある。粘度が上記上限値を超えると、ろ過速度が低下しすぎて工業的生産に不利となる恐れがある。シリコーン組成物の２５℃における粘度は、好ましくは２０〜５００ｍＰａ・ｓ、より好ましくは３０〜４００ｍＰａ・ｓである。 In order to reduce the viscosity of the silicone composition, there is a method of suppressing the viscosity of the component (A) blended in the silicone composition within a predetermined range, or reducing the amount of the silicone component contained in the silicone composition. The viscosity range of the component (A) preferable for the activated carbon treatment is preferably 5,000 mPa · s or more, particularly preferably 10,000 mPa · s or more, and 10,000 to 200,000 mPa · s. A particularly preferable range is 20,000 to 100,000 mPa · s. If the viscosity is less than the above lower limit, the cohesive force (holding force) may decrease. If the viscosity exceeds the above upper limit, the filtration rate may be too low, which may be disadvantageous for industrial production. The viscosity of the silicone composition at 25 ° C. is preferably 20 to 500 mPa · s, more preferably 30 to 400 mPa · s.
また、シリコーン組成物中のシリコーン成分量を減らすことで、シリコーン組成物の粘度を低減することができる。なお、ここでいうシリコーン成分量とは不揮発性のシリコーン成分量であり、特には、上述した（Ａ）成分及び（Ｂ）成分の合計量を意味する。シリコーン組成物中のシリコーン成分量としては、好ましくはシリコーン組成物１００質量部に対して、シリコーン成分量は１０〜７０質量部が好ましい。より好ましくは２０〜６０質量部であり、特に好ましくは２５〜５０質量部である。シリコーン成分量が上記下限値未満では、シリコーン組成物の流動性が高すぎて十分な皮膜を形成することができない恐れがある。また、シリコーン成分量が上記上限を超えると、シリコーン組成物の粘度が高くなりすぎ活性炭処理し難く、好ましくない。 Further, by reducing the amount of the silicone component in the silicone composition, the viscosity of the silicone composition can be reduced. The amount of the silicone component referred to here is the amount of the non-volatile silicone component, and in particular, means the total amount of the above-mentioned components (A) and (B). The amount of the silicone component in the silicone composition is preferably 10 to 70 parts by mass with respect to 100 parts by mass of the silicone composition. It is more preferably 20 to 60 parts by mass, and particularly preferably 25 to 50 parts by mass. If the amount of the silicone component is less than the above lower limit, the fluidity of the silicone composition may be too high to form a sufficient film. Further, if the amount of the silicone component exceeds the above upper limit, the viscosity of the silicone composition becomes too high and it is difficult to treat with activated carbon, which is not preferable.
本発明のシリコーン組成物は、種々の基材に塗工し、所定の条件にて乾燥させることにより皮膜層を得ることができる。基材としては、ポリウレタン、ポリエステル、ポリテトラフルオロエチレン、ポリイミド、ポリフェニレンスルフィド、ポリアミド、ポリカーボネート、ポリスチレン、ポリプロピレン、ポリエチレン、ポリ塩化ビニルなどのプラスチックフィルム、アルミニウム箔、銅箔などの金属箔、和紙、合成紙、ポリエチレンラミネート紙などの紙、布、ガラス繊維、これらのうちの複数を積層してなる複合基材が挙げられる。 The silicone composition of the present invention can be applied to various substrates and dried under predetermined conditions to obtain a film layer. Base materials include polyurethane, polyester, polytetrafluoroethylene, polyimide, polyphenylene sulfide, polyamide, polycarbonate, polystyrene, polypropylene, polyethylene, plastic films such as polyvinyl chloride, metal foils such as aluminum foil and copper foil, Japanese paper, and synthetic paper. Examples thereof include paper such as paper and polyethylene-laminated paper, cloth, glass fiber, and a composite base material obtained by laminating a plurality of these.
上記基材と本発明のシリコーン組成物から成る皮膜の密着性を向上させるために、表面をプライマー処理、コロナ処理、エッチング処理、プラズマ処理、又はサンドブラスト処理された基材を用いてもよい。 In order to improve the adhesion between the base material and the film composed of the silicone composition of the present invention, a base material whose surface is primed, corona-treated, etched, plasma-treated, or sandblasted may be used.
本発明のシリコーン組成物を基材に塗工する方法は特に制限されるものでない。公知の塗工方式を用いればよく、コンマコーター、リップコーター、ロールコーター、ダイコーター、ナイフコーター、ブレードコーター、ロッドコーター、キスコーター、グラビアコーター、スクリーン塗工、浸漬塗工、及びキャスト塗工などが挙げられる。 The method of applying the silicone composition of the present invention to the substrate is not particularly limited. A known coating method may be used, such as comma coater, lip coater, roll coater, die coater, knife coater, blade coater, rod coater, kiss coater, gravure coater, screen coating, immersion coating, and cast coating. Can be mentioned.
シリコーン組成物を基材に塗工する量は、乾燥したあとの粘着剤層の厚みが２〜２００μｍ、特には３〜１００μｍとなるようにするのがよい。基材に塗工した後の乾燥条件は特に制限されないが、例えば８０〜２００℃の範囲にある温度で、３０秒から１０分程度加熱すればよい。 The amount of the silicone composition applied to the substrate is preferably such that the thickness of the pressure-sensitive adhesive layer after drying is 2 to 200 μm, particularly 3 to 100 μm. The drying conditions after coating the base material are not particularly limited, but for example, heating may be performed at a temperature in the range of 80 to 200 ° C. for about 30 seconds to 10 minutes.
また本発明のシリコーン組成物を直接皮膚に塗ることもできる。塗布後、揮発性シリコーンの揮発とともに皮膚上に皮膜を形成できる。皮膚に適用させる場合には、シリコーン組成物に補強成分、美容成分、通常の化粧料に用いられる体質顔料、着色顔料などをさらに配合することができる。 The silicone composition of the present invention can also be applied directly to the skin. After application, a film can be formed on the skin as the volatile silicone volatilizes. When applied to the skin, a reinforcing component, a beauty component, an extender pigment used in ordinary cosmetics, a coloring pigment, and the like can be further added to the silicone composition.
本発明のシリコーン組成物は、上記のように基材に直接塗工して皮膜を形成し、粘着テープ、シート、及びラベルなどを製造することができる。または、皮膚に直接塗布しても良い。本発明のシリコーン粘着剤組成物から成る皮膜を有する粘着テープ、シート、又はラベルなどを貼り合わせる被着体は特に限定されない。各種基材であってもよいが、特に好ましくは人間の皮膚用に用いることができる。 The silicone composition of the present invention can be directly applied to a base material to form a film as described above, and an adhesive tape, a sheet, a label, or the like can be produced. Alternatively, it may be applied directly to the skin. The adherend to which the pressure-sensitive adhesive tape, sheet, label, or the like having a film made of the silicone pressure-sensitive adhesive composition of the present invention is attached is not particularly limited. Various base materials may be used, but it can be particularly preferably used for human skin.
以下、実施例及び比較例を示し、本発明をより詳細に説明するが、本発明は下記の実施例に制限されるものではない。なお、例中の部は質量部を示したものであり、Ｍｅはメチル基を表す。 Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited to the following Examples. The part in the example indicates a mass part, and Me represents a methyl group.
［実施例１］
２５℃での粘度が５０，０００ｍＰａ・ｓであり、分子鎖末端がＯＨ基で封鎖されたポリジメチルシロキサンＩ（４０部）、トルエン中で製造されたＭｅ３ＳｉＯ０．５単位及びＳｉＯ２単位からなるポリシロキサンＩＩ（Ｍｅ３ＳｉＯ０．５単位／ＳｉＯ２単位＝０．８５、重量平均分子量３５００）の６０％トルエン溶液（１００部）、及びオクタメチルトリシロキサン（６６．７部、常圧での沸点１９４℃）の混合物、２８％アンモニア水（０．５部）を添加し室温で６時間撹拌し混合した。その後、還流させながら４時間加熱してアンモニアガスと水とトルエンを留去したのち放冷した。得られた生成物はシロキサン分約６０％であった。該生成物を、５０℃、４０ｈＰａの条件下でストリッピングし、トルエンとオクタメチルトリシロキサンの混合物を留去した後、留出したトルエンとオクタメチルトリシロキサンに相当する量のオクタメチルトリシロキサンを加えて、シロキサン分約４０％のシリコーン組成物を得た。
[Example 1]
Polydimethylsiloxane I (40 parts) with a viscosity at 25 ° C. of 50,000 mPa · s and the end of the molecular chain sealed with an OH group, Me 3 SiO 0.5 units and SiO 2 units produced in toluene. A 60% toluene solution (100 parts) of polysiloxane II (Me 3 SiO 0.5 unit / SiO 2 unit = 0.85, weight average molecular weight 3500), and octamethyltrisiloxane (66.7 parts, normal pressure). A mixture having a boiling point of 194 ° C. (194 ° C.) and 28% aqueous ammonia (0.5 part) were added, and the mixture was stirred and mixed at room temperature for 6 hours. Then, it was heated for 4 hours while refluxing to distill off ammonia gas, water and toluene, and then allowed to cool. The product obtained had a siloxane content of about 60%. The product was stripped under the conditions of 50 ° C. and 40 hPa to distill off a mixture of toluene and octamethyltrisiloxane, and then an amount of octamethyltrisiloxane corresponding to the distilled toluene and octamethyltrisiloxane was added. In addition, a silicone composition having a siloxane content of about 40% was obtained.
［実施例２］
上記実施例１において、ポリジメチルシロキサンＩの配合量を３０部とし、上記ポリシロキサンＩＩの６０％トルエン溶液の配合量を１１７部としたほかは、実施例１の工程を繰り返して、シロキサン分約４０％のシリコーン組成物を得た。
[Example 2]
In Example 1, the compounding amount of polydimethylsiloxane I was 30 parts, and the compounding amount of the 60% toluene solution of polysiloxane II was 117 parts. The steps of Example 1 were repeated to reduce the siloxane content. A 40% silicone composition was obtained.
［実施例３］
上記実施例１において、ポリジメチルシロキサンＩの配合量を７０部とし、上記ポリシロキサンＩＩの６０％トルエン溶液の配合量を５０部としたほかは、実施例１の工程を繰り返して、シロキサン分約４０％のシリコーン組成物を得た。
[Example 3]
In Example 1, the compounding amount of polydimethylsiloxane I was 70 parts, and the compounding amount of the 60% toluene solution of polysiloxane II was 50 parts. The steps of Example 1 were repeated to reduce the siloxane content. A 40% silicone composition was obtained.
［実施例４］
実施例１で作成したシリコーン組成物１００部に活性炭白鷺Ａ（大阪ガスケミカル（株）製）１部を添加し、室温で４時間撹拌した。その後、濾過板としてＮＡ−１０（アドバンテック東洋（株）製）を用いて０．３ＭＰａの圧力で加圧濾過を行い、活性炭を除去して、シロキサン分約６０％を有するシリコーン組成物を得た。
[Example 4]
To 100 parts of the silicone composition prepared in Example 1, 1 part of activated carbon Shirasagi A (manufactured by Osaka Gas Chemical Co., Ltd.) was added, and the mixture was stirred at room temperature for 4 hours. Then, using NA-10 (manufactured by Advantech Toyo Co., Ltd.) as a filtration plate, pressure filtration was performed at a pressure of 0.3 MPa to remove activated carbon to obtain a silicone composition having a siloxane content of about 60%. ..
［実施例５］
上記実施例１において、オクタメチルトリシロキサンをヘキサメチルジシロキサン（常圧での沸点１５３℃）に替えたほかは、実施例１の工程を繰り返して、シロキサン分約４０％のシリコーン組成物を得た。
[Example 5]
In Example 1 above, the steps of Example 1 were repeated except that octamethyltrisiloxane was replaced with hexamethyldisiloxane (boiling point at normal pressure of 153 ° C.) to obtain a silicone composition having a siloxane content of about 40%. rice field.
［実施例６］
上記実施例５で得たシリコーン組成物に活性炭白鷺Ａ（大阪ガスケミカル（株）製）１部を添加し、室温で４時間撹拌した。その後、濾過板としてＮＡ−１０（アドバンテック東洋（株）製）を用いて０．３ＭＰａの圧力で加圧濾過を行い、活性炭を除去して、シロキサン分約６０％を有するシリコーン組成物を得た。
[Example 6]
To the silicone composition obtained in Example 5 above, 1 part of activated carbon Shirasagi A (manufactured by Osaka Gas Chemical Co., Ltd.) was added, and the mixture was stirred at room temperature for 4 hours. Then, using NA-10 (manufactured by Advantech Toyo Co., Ltd.) as a filtration plate, pressure filtration was performed at a pressure of 0.3 MPa to remove activated carbon to obtain a silicone composition having a siloxane content of about 60%. ..
［実施例７］
上記実施例１において（Ａ）成分を、３０％の濃度となるようにトルエンで溶解したときの粘度が１，４００ｍＰａ・ｓであり、末端基がＯＨ基であるポリジメチルシロキサンＩ（４０部）に替え、得られる組成物のシリコーン分が２５質量％となるようにオクタメチルトリシロキサンを添加した他は、実施例１の工程を繰り返してシリコーン組成物を得た。
[Example 7]
Polydimethylsiloxane I (40 parts) having a viscosity of 1,400 mPa · s and an OH group as a terminal group when the component (A) was dissolved in toluene so as to have a concentration of 30% in Example 1 above. A silicone composition was obtained by repeating the steps of Example 1 except that octamethyltrisiloxane was added so that the silicone content of the obtained composition was 25% by mass.
［比較例１］
２５℃での粘度が５０，０００ｍＰａ・ｓであり、分子鎖末端がＯＨ基で封鎖されたポリジメチルシロキサンＩ（４０部）、Ｍｅ３ＳｉＯ０．５単位及びＳｉＯ２単位からなるポリシロキサンＩＩ（Ｍｅ３ＳｉＯ０．５単位／ＳｉＯ２単位＝０．８５）の６０％トルエン溶液（１００部）、及びトルエン（６６．７部）からなる溶液に、２８％アンモニア水（０．５部）を添加し室温で６時間撹拌した。その後、還流させながら４時間加熱してアンモニアガスと水を留去したのち放冷した。得られた生成物はシロキサン分約６０％であった。該生成物に含まれるトルエン量は２０〜２５％であった。該生成物にシロキサン分約４０％となるようにトルエンを追加して、シリコーン組成物を得た。
[Comparative Example 1]
Polysiloxane II (40 parts) having a viscosity at 25 ° C. of 50,000 mPa · s and having a molecular chain end sealed with an OH group, Me 3 SiO 0.5 unit and SiO 2 unit. 28% aqueous ammonia (0.5 parts) was added to a solution consisting of a 60% toluene solution (100 parts) of Me 3 SiO 0.5 units / SiO 2 units = 0.85) and toluene (66.7 parts). It was added and stirred at room temperature for 6 hours. Then, the mixture was heated for 4 hours while refluxing to distill off ammonia gas and water, and then allowed to cool. The product obtained had a siloxane content of about 60%. The amount of toluene contained in the product was 20 to 25%. Toluene was added to the product so that the siloxane content was about 40% to obtain a silicone composition.
［比較例２］
実施例１で得たシリコーン組成物を実施例４の工程を繰り返して活性炭処理を行い、シリコーン組成物を得た。該シリコーン組成物に含まれるトルエン量は３５ｐｐｍであった。該シリコーン組成物にトルエンが５００ｐｐｍとなるよう添加し、よく撹拌した。
[Comparative Example 2]
The silicone composition obtained in Example 1 was treated with activated carbon by repeating the steps of Example 4 to obtain a silicone composition. The amount of toluene contained in the silicone composition was 35 ppm. Toluene was added to the silicone composition so as to be 500 ppm, and the mixture was thoroughly stirred.
上記実施例１〜７及び比較例１及び２で得たシリコーン組成物の皮膜形成性、シリコーン組成物の残留トルエン量、粘着テープの残留トルエン量、臭いレベル、及び皮膚刺激性を下記の方法に従い評価した。結果を表１に示す。 The film-forming properties of the silicone compositions obtained in Examples 1 to 7 and Comparative Examples 1 and 2, the amount of residual toluene in the silicone composition, the amount of residual toluene in the adhesive tape, the odor level, and the skin irritation were determined according to the following methods. evaluated. The results are shown in Table 1.
皮膜形成性
シリコーン組成物溶液を、厚み２５μｍ、幅２５ｍｍのポリエチレンテレフタレートフィルムに乾燥後の厚みが３０μｍとなるようにアプリケータを用いて塗工した後、１３０℃、２分の条件で加熱し乾燥させ、粘着テープを作成した。この粘着テープの表面を触診することで皮膜形成性を確認した。得られた粘着テープ表面を触った際に、指に粘着剤残渣及びぬめり（ぬるっとした感じ）が確認されないものを良好と評価し、粘着剤残渣又はぬめりが確認されたものを不良と評価した。
The film-forming silicone composition solution is applied to a polyethylene terephthalate film having a thickness of 25 μm and a width of 25 mm using an applicator so that the thickness after drying is 30 μm, and then heated at 130 ° C. for 2 minutes and dried. And made an adhesive tape. The film-forming property was confirmed by palpating the surface of this adhesive tape. When the surface of the obtained adhesive tape is touched, those in which no adhesive residue and sliminess (slimy feeling) are confirmed on the finger are evaluated as good, and those in which adhesive residue or sliminess is confirmed are evaluated as defective. bottom.
シリコーン組成物の残留トルエン量
オクタメチルトリシロキサンにトルエン濃度が、それぞれ１０ｐｐｍ、１００ｐｐｍ、１０００ｐｐｍとなるように配合し、波長２６７．６ｎｍから２７０．６ｎｍに確認される紫外吸収量を測定し検量線を得た。各シリコーン組成物の紫外吸収スペクトルを波長２６７．６ｎｍから２７０．６ｎｍにて測定し、残留トルエン量を確認した。
Amount of Residual Toluene in Silicone Composition Octamethyltrisiloxane was blended with toluene concentrations of 10 ppm, 100 ppm, and 1000 ppm, respectively, and the amount of ultraviolet absorption confirmed at wavelengths from 267.6 nm to 270.6 nm was measured and a calibration curve was obtained. Obtained. The ultraviolet absorption spectrum of each silicone composition was measured at a wavelength of 267.6 nm to 270.6 nm, and the amount of residual toluene was confirmed.
粘着テープの残留トルエン量
皮膜形成性評価と同じ方法で粘着テープを作成した。この粘着テープの約１０ｃｍを秤量したのち、バイアルびんに封入した。このバイアルびんを２６０℃１時間加熱したのち、バイアルびん中の気体をガスクロマトグラフィーにより分析して発生した単位テープ質量あたりのトルエン量を定量した。
The amount of residual toluene of the adhesive tape The adhesive tape was prepared by the same method as the evaluation of film formation. About 10 cm of this adhesive tape was weighed and then sealed in a vial. After heating this vial at 260 ° C. for 1 hour, the gas in the vial was analyzed by gas chromatography to quantify the amount of toluene per unit tape mass generated.
臭いレベル
シリコーン組成物溶液の臭いの強さを嗅覚で判定した。判定は５名で行い，無，微，中，強の４段階で判定した。
Odor level The intensity of the odor of the silicone composition solution was determined by the sense of smell. The judgment was made by 5 people, and the judgment was made in 4 stages of none, fine, medium, and strong.
［参考例１］
実施例１において（Ｂ）成分を、イソパラフィン中で製造したＭｅ３ＳｉＯ０．５単位及びＳｉＯ２単位からなるポリシロキサン（Ｍｅ３ＳｉＯ０．５単位／ＳｉＯ２単位＝０．８５、重量平均分子量２８００）の６０％イソパラフィン溶液（１００部）に替えたほかは、実施例１の工程を繰り返してシリコーン組成物を得た。上記と同じ方法にて皮膜形成性を評価したところ、皮膜の強度が弱く、粘着テープ表面に粘着剤残渣及びぬめりが確認され、皮膜形成性は不良であった。また臭いレベルを測定したところ強い臭いが確認された。
[Reference example 1]
In Example 1, the component (B) is a polysiloxane (Me 3 SiO 0.5 unit / SiO 2 unit = 0.85, weight average molecular weight) composed of 0.5 unit of Me 3 SiO and 2 units of SiO produced in isoparaffin. A silicone composition was obtained by repeating the steps of Example 1 except that the solution was replaced with a 60% isoparaffin solution (100 parts) of 2800). When the film-forming property was evaluated by the same method as above, the strength of the film was weak, adhesive residue and sliminess were confirmed on the surface of the adhesive tape, and the film-forming property was poor. Moreover, when the odor level was measured, a strong odor was confirmed.
［皮膚刺激性］
上記皮膜形成性評価と同様の方法で粘着テープを作成した。該粘着テープを１ｃｍ×０．５ｃｍに切り出した後、１０人の前腕部に貼り付けた。４時間後にテープを剥がし，貼り付け部のかぶれを確認した。かぶれの発生強度（赤く変色した強度）を目視で観察し、下記に従い評価した。１０人のパネラーによる評価点数の平均値を算出した。結果を表２に示す。
かぶれが無い：１点、
かぶれが少しある：２点
かぶれが強い：３点
[Skin irritation]
An adhesive tape was prepared in the same manner as in the above film formability evaluation. The adhesive tape was cut into 1 cm × 0.5 cm and then attached to the forearms of 10 people. After 4 hours, the tape was peeled off and a rash on the pasted part was confirmed. The intensity of rash occurrence (intensity of discoloration to red) was visually observed and evaluated according to the following. The average value of the evaluation points by 10 panelists was calculated. The results are shown in Table 2.
No rash: 1 point,
Slight rash: 2 points Strong rash: 3 points
上記表２に示す通り、比較例１及び２のシリコーン組成物から成る皮膜を有する粘着テープは、トルエンを含むため皮膚に対する刺激を生じた。これに対し、本発明のシリコーン組成物から成る皮膜を有する粘着テープは皮膚に対する刺激がない。また表１に示す通り、本発明のシリコーン組成物は皮膜形成性が良好である。特に活性炭で脱臭処理した実施例４及び６のシリコーン組成物から得られる皮膜は臭いがほとんどなく、医療用及び化粧料用の粘着剤組成物として、より好適に用いることができる。 As shown in Table 2 above, the adhesive tape having a film made of the silicone compositions of Comparative Examples 1 and 2 caused irritation to the skin because it contained toluene. On the other hand, the adhesive tape having a film made of the silicone composition of the present invention is not irritating to the skin. Further, as shown in Table 1, the silicone composition of the present invention has good film-forming property. In particular, the films obtained from the silicone compositions of Examples 4 and 6 deodorized with activated carbon have almost no odor, and can be more preferably used as an adhesive composition for medical use and cosmetics.
本発明のシリコーン組成物は皮膜形成が良好であり、皮膚への刺激を抑制された皮膜を形成することができる。従って、本発明のシリコーン組成物は、医療用粘着剤、及び化粧料用粘着剤の皮膜を形成するのに好適であり、絆創膏などの人間の皮膚に適応する医療用粘着剤や、マスカラ等の化粧料用粘着剤として好適である。
The silicone composition of the present invention has good film formation and can form a film in which irritation to the skin is suppressed. Therefore, the silicone composition of the present invention is suitable for forming a film of a medical pressure-sensitive adhesive and a cosmetic pressure-sensitive adhesive, and is suitable for a medical pressure-sensitive adhesive such as an adhesive plaster and a mascara. Suitable as a cosmetic adhesive.
Claims (16)
（Ａ）末端に水酸基を有するポリジオルガノシロキサン
該（Ａ）成分と下記（Ｂ）成分の合計１００質量部に対し２０〜８０質量部
（Ｂ）Ｒ１ ３ＳｉＯ０．５単位およびＳｉＯ２単位を含有し、Ｒ１ ３ＳｉＯ０．５単位／ＳｉＯ２単位のモル比が０．６〜１．７であり、芳香族炭化水素溶剤中にて製造されたポリオルガノシロキサン樹脂（前記Ｒ１は、炭素数１〜１０の１価炭化水素基である）
前記（Ａ）成分と該（Ｂ）成分の合計１００質量部に対し８０〜２０質量部、及び
（Ｃ）常圧で１５０℃〜２００℃の範囲にある沸点を有する揮発性シリコーン
前記（Ａ）成分及び（Ｂ）成分の合計１００質量部に対して２５〜９００質量部
を含むシリコーン組成物であり、該シリコーン組成物における芳香族炭化水素の含有量が０〜１００重量ｐｐｍであることを特徴とする、前記シリコーン組成物の製造方法であって、
該製造方法は、前記（Ａ）成分、前記（Ｂ）成分、及び前記（Ｃ）成分を混合する工程と、該工程で得た生成物を減圧留去することで芳香族炭化水素含有量を０〜１００重量ｐｐｍとする工程とを含むことを特徴とする、前記製造方法。 Polydiorganosiloxane having a hydroxyl group at the end of components (A) below (A) to (C)
20 to 80 parts by mass (B) R 1 3 SiO 0.5 unit and SiO 2 unit are contained with respect to a total of 100 parts by mass of the component (A) and the component (B) below , and R 1 3 SiO 0.5 unit. / is the molar ratio of SiO 2 units 0.6 to 1.7, polyorganosiloxane resin prepared by an aromatic hydrocarbon solvent (the R 1 is a monovalent hydrocarbon group having 1 to 10 carbon atoms Is)
Volatile silicone having a boiling point in the range of 80 to 20 parts by mass and (C) 150 ° C. to 200 ° C. under normal pressure with respect to 100 parts by mass of the total of the component (A) and the component (B). It is a silicone composition containing 25 to 900 parts by mass with respect to a total of 100 parts by mass of the component and the component (B), and the content of aromatic hydrocarbons in the silicone composition is 0 to 100 parts by mass. This is a method for producing the silicone composition.
The production method comprises a step of mixing the component (A), the component (B), and the component (C), and distilling off the product obtained in the step under reduced pressure to reduce the aromatic hydrocarbon content. The production method, which comprises a step of 0 to 100 ppm by weight.
（Ａ）末端に水酸基を有するポリジオルガノシロキサン
該（Ａ）成分と下記（Ｂ）成分の合計１００質量部に対し２０〜８０質量部
（Ｂ）Ｒ１ ３ＳｉＯ０．５単位およびＳｉＯ２単位を含有し、Ｒ１ ３ＳｉＯ０．５単位／ＳｉＯ２単位のモル比が０．６〜１．７であるポリオルガノシロキサン樹脂（前記Ｒ１は、炭素数１〜１０の１価炭化水素基である）
前記（Ａ）成分と該（Ｂ）成分の合計１００質量部に対し８０〜２０質量部、及び
（Ｃ）常圧で１５０℃〜２００℃の範囲にある沸点を有する揮発性シリコーン
前記（Ａ）成分及び（Ｂ）成分の合計１００質量部に対して２５〜９００質量部
かつ、前記シリコーン組成物は芳香族炭化水素の含有量が０〜１００重量ｐｐｍであることを特徴とする、前記シリコーン組成物。 A silicone composition containing the following components (A) to (C).
(A) Polydiorganosiloxane having a hydroxyl group at the end
20 to 80 parts by mass (B) R 1 3 SiO 0.5 unit and SiO 2 unit are contained with respect to a total of 100 parts by mass of the component (A) and the component (B) below , and R 1 3 SiO 0.5 unit. / molar ratio of SiO 2 units is 0.6 to 1.7 polyorganosiloxane resin (wherein R 1 is a monovalent hydrocarbon group having 1 to 10 carbon atoms)
Volatile silicone having a boiling point in the range of 80 to 20 parts by mass and (C) 150 ° C. to 200 ° C. under normal pressure with respect to 100 parts by mass of the total of the component (A) and the component (B). The silicone composition is 25 to 900 parts by mass with respect to a total of 100 parts by mass of the component and the component (B), and the silicone composition has an aromatic hydrocarbon content of 0 to 100% by weight. thing.
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Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09137150A (en) * | 1995-06-06 | 1997-05-27 | General Electric Co <Ge> | Pressure-sensitive silicone adhesive composition and its production |
| JP2001011423A (en) * | 1999-06-29 | 2001-01-16 | Ge Toshiba Silicones Co Ltd | Silicone adhesive composition for pressure-sensitive adhesive tape |
| JP2005504165A (en) * | 2001-10-01 | 2005-02-10 | ダウ・コーニング・コーポレーション | Silicone pressure sensitive adhesive composition |
| JP2006193598A (en) * | 2005-01-13 | 2006-07-27 | Shin Etsu Chem Co Ltd | Silicone adhesive composition containing no aromatic solvent, adhesive tape, sheet or label coated with the same |
| WO2011087146A1 (en) * | 2010-01-13 | 2011-07-21 | 東レ・ダウコーニング株式会社 | Re-adherable silicone-based adhesive composition, sheet-shaped base material having re-adherable adhesive layer obtained by curing said composition, and use of said base material as protective film or affixing sheet |
| JP2013245280A (en) * | 2012-05-25 | 2013-12-09 | Shin-Etsu Chemical Co Ltd | Radiation-curable silicone composition and release sheet |
| JP2014043505A (en) * | 2012-08-27 | 2014-03-13 | Mitsubishi Chemicals Corp | Liquid polysiloxane composition, kit for producing polysiloxane cured product, and production method of the same |
| JP2018002874A (en) * | 2016-07-01 | 2018-01-11 | 信越化学工業株式会社 | Aminoalkyl group-containing siloxane, an aminoalkyl group-and polyoxyalkylene group-containing siloxane, and method for producing them |
-
2020
- 2020-03-24 JP JP2020053454A patent/JP2021152122A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09137150A (en) * | 1995-06-06 | 1997-05-27 | General Electric Co <Ge> | Pressure-sensitive silicone adhesive composition and its production |
| JP2001011423A (en) * | 1999-06-29 | 2001-01-16 | Ge Toshiba Silicones Co Ltd | Silicone adhesive composition for pressure-sensitive adhesive tape |
| JP2005504165A (en) * | 2001-10-01 | 2005-02-10 | ダウ・コーニング・コーポレーション | Silicone pressure sensitive adhesive composition |
| JP2006193598A (en) * | 2005-01-13 | 2006-07-27 | Shin Etsu Chem Co Ltd | Silicone adhesive composition containing no aromatic solvent, adhesive tape, sheet or label coated with the same |
| WO2011087146A1 (en) * | 2010-01-13 | 2011-07-21 | 東レ・ダウコーニング株式会社 | Re-adherable silicone-based adhesive composition, sheet-shaped base material having re-adherable adhesive layer obtained by curing said composition, and use of said base material as protective film or affixing sheet |
| JP2013245280A (en) * | 2012-05-25 | 2013-12-09 | Shin-Etsu Chemical Co Ltd | Radiation-curable silicone composition and release sheet |
| JP2014043505A (en) * | 2012-08-27 | 2014-03-13 | Mitsubishi Chemicals Corp | Liquid polysiloxane composition, kit for producing polysiloxane cured product, and production method of the same |
| JP2018002874A (en) * | 2016-07-01 | 2018-01-11 | 信越化学工業株式会社 | Aminoalkyl group-containing siloxane, an aminoalkyl group-and polyoxyalkylene group-containing siloxane, and method for producing them |
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