JP2004275213A - Silicone adhesive composition for dermal pasting material and dermal pasting material using the same - Google Patents
Silicone adhesive composition for dermal pasting material and dermal pasting material using the same Download PDFInfo
- Publication number
- JP2004275213A JP2004275213A JP2003066950A JP2003066950A JP2004275213A JP 2004275213 A JP2004275213 A JP 2004275213A JP 2003066950 A JP2003066950 A JP 2003066950A JP 2003066950 A JP2003066950 A JP 2003066950A JP 2004275213 A JP2004275213 A JP 2004275213A
- Authority
- JP
- Japan
- Prior art keywords
- mass
- dermal
- skin
- parts
- silicone
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 22
- 239000000463 material Substances 0.000 title claims abstract description 15
- 239000013464 silicone adhesive Substances 0.000 title claims abstract description 14
- 230000002500 effect on skin Effects 0.000 title abstract 5
- 230000001070 adhesive effect Effects 0.000 claims abstract description 31
- 239000000853 adhesive Substances 0.000 claims abstract description 25
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 17
- 125000005375 organosiloxane group Chemical group 0.000 claims abstract description 17
- 229920000642 polymer Polymers 0.000 claims abstract description 16
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 9
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 26
- 229920001296 polysiloxane Polymers 0.000 claims description 14
- 239000007933 dermal patch Substances 0.000 claims description 11
- 238000004132 cross linking Methods 0.000 claims description 9
- 239000010410 layer Substances 0.000 claims description 9
- 239000012790 adhesive layer Substances 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- -1 isocyanate compound Chemical class 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- 239000000178 monomer Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 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 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 239000002250 absorbent Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000004745 nonwoven fabric Substances 0.000 description 3
- 230000035699 permeability Effects 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000011505 plaster Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 229920002050 silicone resin Polymers 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 206010040880 Skin irritation Diseases 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 230000036556 skin irritation Effects 0.000 description 2
- 231100000475 skin irritation Toxicity 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- HYYJOCXNESGFSB-UHFFFAOYSA-N 1-(oxiran-2-yl)-n-(oxiran-2-ylmethyl)methanamine Chemical compound C1OC1CNCC1CO1 HYYJOCXNESGFSB-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- KQSMCAVKSJWMSI-UHFFFAOYSA-N 2,4-dimethyl-1-n,1-n,3-n,3-n-tetrakis(oxiran-2-ylmethyl)benzene-1,3-diamine Chemical compound CC1=C(N(CC2OC2)CC2OC2)C(C)=CC=C1N(CC1OC1)CC1CO1 KQSMCAVKSJWMSI-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 1
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 description 1
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
- NQSLZEHVGKWKAY-UHFFFAOYSA-N 6-methylheptyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C(C)=C NQSLZEHVGKWKAY-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Chemical class 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
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- 230000002745 absorbent Effects 0.000 description 1
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- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Chemical class 0.000 description 1
- 229910000389 calcium phosphate Chemical class 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920002678 cellulose Chemical class 0.000 description 1
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- 238000009833 condensation Methods 0.000 description 1
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- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
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- 238000009472 formulation Methods 0.000 description 1
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- 235000011187 glycerol Nutrition 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
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- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
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- SJPFBRJHYRBAGV-UHFFFAOYSA-N n-[[3-[[bis(oxiran-2-ylmethyl)amino]methyl]phenyl]methyl]-1-(oxiran-2-yl)-n-(oxiran-2-ylmethyl)methanamine Chemical compound C1OC1CN(CC=1C=C(CN(CC2OC2)CC2OC2)C=CC=1)CC1CO1 SJPFBRJHYRBAGV-UHFFFAOYSA-N 0.000 description 1
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- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
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- 231100000046 skin rash Toxicity 0.000 description 1
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- 239000008107 starch Chemical class 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Abstract
Description
【0001】
【発明の属する技術分野】
本発明は皮膚貼付材用シリコーン粘着剤組成物及びこれを用いた皮膚貼付材に関するものである。
【0002】
【従来の技術】
シリコーン粘着剤は、通気性、低皮膚刺激性から人体貼付用途に使用されている。これらは貼付時の粘着物性を考慮し、過酸化物、白金触媒を用いて架橋させて使用することがあり、また架橋しないで使用されることもある(例えば、特許文献1)。
【0003】
しかしながら、前記のような方法で架橋させた場合、十分な保持力を発現するが、シリコーン粘着剤が本来有する粘着物性(タック、粘着力)が低下し、人体貼付用粘着剤としての適性が低下することがある。一方、架橋を行わない場合、保持力が不十分となり、剥離後に粘着剤が皮膚面に残存するようになる。
【特許文献1】
特開平3−200885号公報
【0004】
【発明が解決しようとする課題】
本発明の課題は、シリコーン粘着剤が本来有する粘着物性(皮膚への高い接着性、タック)を維持したまま、保持力を向上させた皮膚貼付材用シリコーン粘着剤組成物及び皮膚貼付材を提供することにある。
【0005】
【課題を解決するための手段】
本発明者は、前記の課題を解決すべく鋭意研究を重ねた結果、末端に水酸基を有するオルガノシロキサン系ポリマーを、前記水酸基と反応しうる架橋剤と反応させることにより、前記オルガノシロキサン系ポリマーの分子鎖のフレキシビリティーを維持したまま適度に架橋することができ、その結果、シリコーン粘着剤が本来有する粘着物性を維持しつつ、保持力を向上させることができることを見出し、本発明を完成するに至った。
【0006】
即ち、本発明は、以下の発明を包含する。
(1)末端に水酸基を有するオルガノシロキサン系ポリマー100質量部、及び前記水酸基と反応しうる架橋剤0.1〜15質量部を含有し、更に必要に応じてアクリル系ポリマー0〜10質量部を含有する皮膚貼付材用シリコーン粘着剤組成物。
(2)支持体の片面に皮膚貼着用の粘着剤層を積層してなる皮膚貼付材であって、粘着剤層が、前記(1)に記載のシリコーン粘着剤組成物を架橋することにより形成されたものである皮膚貼付材。
(3)前記(2)に記載の皮膚貼付材における粘着剤層表面の中央域に吸液性パッドを設けてなる救急絆創膏。
【0007】
【発明の実施の形態】
本発明は、オルガノシロキサン系ポリマーを、水酸基と反応しうる架橋剤と反応させることにより、適度に架橋することを特徴とする。
【0008】
本発明に用いるオルガノシロキサン系ポリマーとしては、例えば特開平3−200885号公報、特開2001−11423号公報、特開2002−200160号公報に記載されたものが挙げられる。
具体的には、一般式(I):
【0009】
【化1】
(式中、R1及びR2はそれぞれメチル基又はフェニル基、nは整数を表す。)
で示されるオルガノシロキサン系のゴム成分に一般式(II):
【0010】
【化2】
(式中、mは整数を表す。)
で示されるシリコーンレジンを配合して脱水縮合することにより得られるオルガノシロキサン系ポリマーが挙げられる。
【0011】
また、一般式(II)以外のシリコーンレジンとして、ケイ素原子に結合した水酸基を分子中に3個以上有する分岐状ポリオルガノシロキサンを単独又は併用することも好ましい。
【0012】
前記一般式(I)において、R1及びR2はそれぞれメチル基又はフェニル基であるが、粘着剤層に耐熱性などを付与するためには、メチル基とフェニル基のモル比(メチル基/フェニル基)は、25/75〜98/2、特に85/15〜95/5であることが好ましい。
【0013】
また、前記式(I)で示されるオルガノシロキサン系のゴム成分(以下「(1)成分」という。)と、前記式(II)で示されるシリコーンレジン又は前記ケイ素原子に結合した水酸基を分子中に3個以上有する分岐状ポリオルガノシロキサン(以下「(2)成分」という。)との部分縮合反応によって得られたシリコーン粘着剤が、ケイ素原子に結合した水酸基を、分子中に0.1〜0.9質量%含有することが好ましい。更に好ましくは、0.2〜0.7質量%である。この範囲では特に粘着特性の経時安定性が優れている。
【0014】
このようなシリコーン粘着剤として、例えばダウ・コーニング社製355;ゼネラル・エレクトリック社製PSA518、PSA590、PSA595、PSA6574;GE東芝シリコーン(株)製YR3340、XR37−B6722などが市販されており、これらの市販品を用いることができる。
【0015】
本発明のシリコーン粘着剤組成物は、前記オルガノシロキサン系ポリマーの末端水酸基と反応しうる架橋剤を含有する。このような架橋剤としては、末端水酸基と反応しうる官能基を2個以上有する多官能架橋剤が挙げられる。有機過酸化物のような水酸基を介した架橋に一般には用いられない架橋剤は、本発明における水酸基と反応しうる架橋剤には該当しない。
【0016】
前記オルガノシロキサン系ポリマーの末端水酸基と反応しうる官能基としては、例えばイソシアナト基、グリシジル基、カルボキシル基が挙げられる。
前記多官能架橋剤の具体例としては、イソシアナート化合物、エポキシ化合物、カルボン酸化合物等が挙げられる。
【0017】
前記イソシアナート化合物としては、トリレンジイソシアナート、水素化トリレンジイソシアナート、トリメチロールプロパンのトリレンジイソシアナートアダクト、トリメチロールプロパンのキシリレンジイソシアナートアダクト、トリフェニルメタントリイソシアナート、メチレンビス(4−フェニルメタン)トリイソシアナート、イソホロンジイソシアナート等、及びこれらのケトオキシムブロック物又はフェノールブロック物あるいはイソシアヌレート等が挙げられる。
【0018】
前記エポキシ化合物としては、ビスフェノールA・エピクロルヒドリン型のエポキシ樹脂、エチレングリコールジグリシジルエーテル、ポリエチレングリコールジグリシジルエーテル、グリセリンジ又はトリグリシジルエーテル、1,6−ヘキサンジオールジグリシジルエーテル、トリメチロールプロパントリグリシジルエーテル、ジグリシジルアニリン、ジグリシジルアミン、N,N,N′,N′−テトラグリシジル−m−キシレンジアミン、1,3−ビス(N,N′−ジグリシジルアミノメチル)シクロヘキサン等が挙げられる。
前記カルボン酸化合物としては、アジピン酸、セバシン酸、フマル酸、マレイン酸、フタル酸等が挙げられる。
【0019】
前記架橋剤の配合量は前記オルガノシロキサン系ポリマー100質量部に対して0.1〜15質量部、好ましくは0.2〜13質量部、更に好ましくは0.4〜12質量部である。前記配合量が0.1質量部未満では、前記オルガノシロキサン系ポリマーの架橋構造の形成が充分になされず、保持力向上の効果が得られず、一方15質量部を超えると、保持力は向上するが、過度の架橋により粘着力、タックが低下することがある。
【0020】
本発明のシリコーン粘着剤組成物には、必要に応じてアクリル系ポリマーを配合することができる。その配合量は、前記オルガノシロキサン系ポリマー100質量部に対して10質量部以下であることが好ましい。アクリル系ポリマーの配合量が10質量部を超えると、層分離によるシリコーン粘着剤の物性低下や耐水性が低下する不具合がある。
【0021】
前記アクリル系ポリマーの原料単量体の主成分として用いられる(メタ)アクリル酸アルキルエステルとしては、特に制限はないが、通常、エステル基を構成するアルキル基が炭素数1〜18のアルキル基である各種のアクリル酸アルキルエステル又はメタクリル酸アルキルエステルを使用でき、具体的にはアクリル酸メチル、アクリル酸エチル、アクリル酸プロピル、アクリル酸n−ブチル、アクリル酸イソブチル、アクリル酸2−エチルヘキシル、アクリル酸イソオクチル、メタクリル酸メチル、メタクリル酸エチル、メタクリル酸プロピル、メタクリル酸n−ブチル、メタクリル酸イソブチル、メタクリル酸2−エチルヘキシル、メタクリル酸イソオクチル等を挙げることができる。
【0022】
本発明において、アクリル系ポリマーを構成する単量体としては、前記(メタ)アクリル酸アルキルエステルを単独で又は2種以上組み合わせて用いてもよいし、更に共重合可能な他の単量体を併用してもよい。共重合可能な他の単量体としては、酢酸ビニル、スチレン、アクリロニトリル、アクリルアミド、ジメチルアクリルアミド、アクリル酸、メタクリル酸、アクリル酸2−ヒドロキシエチル、メタクリル酸グリシジル、アクリル酸4−ヒドロキシブチル、N−ビニルピロリドン等のアクリル系粘着剤の改質用単量体として知られる各種の単量体をいずれも使用可能である。
【0023】
これらの単量体の重合は、溶液重合、エマルジヨン重合、塊状重合等の通常の重合方法によって行われる。重合の反応温度は、通常50〜85℃、好ましくは60〜80℃である。
【0024】
溶液重合を行う場合には、アセトン、ベンゼン、トルエン、酢酸エチル、ヘキサン、ヘプタン、メタノール、エタノール、イソプロパノール等の溶媒中で、固形分濃度通常0.5〜60質量%、好ましくは5〜50質量%で、アゾビスイソブチロニトリル、ベンゾイルペルオキシド等の重合開始剤を用いて行われる。
重合開始剤の配合量(固形分)は、アクリル系ポリマー(固形分)100質量部に対して、通常0.05〜1質量部である。
【0025】
本発明の粘着剤組成物には、必要に応じて、プロセスオイル、ポリイソブチレン、ポリブテン等の軟化剤;酸化チタン、酸化亜鉛、メタケイ酸アルミニウム、炭酸カルシウム、リン酸カルシウム等の充填剤;デンプン、セルロース誘導体、ポリビニルアルコール等の保水機能付与剤;流動パラフィンなどを配合することができる。
【0026】
本発明の粘着剤組成物の使用に際しては、トルエン、酢酸エチル、メチルエチルケトン、アセトン等の有機溶剤に溶解したものを支持体又は剥離フィルム等のフィルムに塗布した後、30〜170℃、好ましくは40〜150℃の乾燥温度で乾燥することにより架橋され、その粘着特性が得られる。
【0027】
本発明の皮膚貼付材又は救急絆創膏に用いる支持体は、前記粘着剤組成物からなる粘着剤層を片面に積層保持するものである。具体的な材質としては、ポリスチレン系の熱可塑性エラストマーフィルムや、ポリエチレン、ポリプロピレン、エチレン/メタクリル酸共重合体、エチレン/メタクリル酸メチルなどのポリオレフィン系フィルム、ポリウレタン系フィルム、ポリエステル系フィルム、各種プラスチック材料からなる織布や不織布、編布、紙、その他これらのフィルム同士の積層体、紙同士の積層体などを用いることができる。
【0028】
前記支持体の厚みは材質によって任意であるが、通常、フィルムを支持体とする場合には15〜250μm、好ましくは30〜100μm程度とし、織布、不織布、紙などを支持体とする場合には50〜500μm、好ましくは100〜300μm程度とする。
【0029】
本発明の皮膚貼付材及び救急絆創膏は、支持体の片面に特定の組成を有する粘着剤層を積層してなるものである。積層は、前記粘着剤組成物を塗工することにより行うことができ、この塗工は一般の塗工方式に従って直接又は転写塗工方式により行うことができる。
【0030】
また、本発明に用いる支持体として、透湿性がない材質のフィルムを用いた場合には、皮膚面に長時間貼付すると貼付部位にムレを生じて、その結果、皮膚カブレなどを起こすことがある。従って、このような支持体を用いる場合や透湿性を有する支持体を用いる場合であっても、更に透湿性を付与したい場合には、支持体及び粘着剤層に穿孔処理を施すことが好ましい。穿孔処理を施すには穿孔ロールによる方法や、パンチング、レーザー照射などの方法を用いることができ、孔径は0.2〜2mm程度とする。
【0031】
更に、本発明においては、前記のようにして得られる皮膚貼付材の粘着剤層表面の中央域に吸液性パッドを設けて救急絆創膏とすることもできる。吸液性パッドとしては、例えばガーゼや綿布、不織布、脱脂綿と不織布との複合品、脱脂綿と編ネットとの複合品などを用いることができ、創傷部からの滲出液を吸収し、しかも創傷部の保護を行うことができて好ましい。
【0032】
本発明の皮膚貼付材及び救急絆創膏は、粘着剤層の表面の汚染を防ぐために、使用するまで粘着剤層表面を剥離材にて被覆しておくことが好ましい。この場合、使用する剥離材は紙、ポリオレフィンラミネート紙、ポリエステルフィルムなどにオルガノシロキサン系ポリマーを含有する粘着剤層との離型性を良好とするために剥離材用のフッ素系シリコーンやメチル系シリコーンを塗布したものを用いることが好適である。
【0033】
【実施例】
以下、実施例及び比較例により本発明を更に具体的に説明するが、これらは本発明の範囲を何ら制限するものではない。以下において、部とは質量部を意味し、%とは質量%を意味する。
[実施例1]
メチルフェニル系シリコーン粘着剤(XR37−B6722、GE東芝シリコーン製)100部(固形分量)に3官能イソシアナート系架橋剤(コロネートHL、日本ポリウレタン製)を3部(固形分量)加え、十分に攪拌した。次に、シリコーン粘着剤用剥離紙(バイナシート70XT−032HK−H、藤森工業製)の上に乾燥後の塗布量が40g/m2になるようにコートし、100℃で3分間温風により乾燥した。乾燥後、厚さ25μmのポリエチレンテレフタレート(PET)フィルム(ルミラー、東レ製)を貼りあわせ、粘着シートを作成した。[実施例2]
架橋剤配合量を6部とした以外は、実施例1と同様の方法にて粘着シートを作成した。
[実施例3]
架橋剤配合量を12部とした以外は、実施例1と同様の方法にて粘着シートを作成した。
[実施例4]
架橋剤としてN,N,N’,N’−テトラグリシジル−m−キシレンジアミン(TETRAD−X、三菱ガス化学製)を用い、配合量0.4部(固形分量)とした以外は実施例1と同様の方法にて粘着シートを作成した。
[実施例5]
架橋剤として3官能イソシアナート系架橋剤(コロネートHL、日本ポリウレタン製)を用い、配合量3部(固形分量)としたものに、さらにアクリル系ポリマー(アクリル酸n−ブチル99質量部、アクリル酸4−ヒドロキシブチル1質量部、アゾビスイソブチロニトリル0.25質量部、酢酸エチル130質量部の混合液を窒素ガス雰囲気下、65℃にて12時間重合したもの)10質量部(固形分量)を加えた以外は、実施例1と同様の方法にて粘着シートを作成した。
【0034】
[比較例1]
架橋剤を加えない以外は、実施例1と同様の方法にて粘着シートを作成した。実施例1〜5及び比較例1の粘着シートについて、被着体をフェノール樹脂板とし、JIS Z0237に従い粘着力とプローブタックを測定した。また、クリープテスターにより40℃下での保持力(被着体SUS)をおもりの落下時間として測定した。それぞれの配合、測定結果を表1に示す。表1から、未架橋のもの(比較例1)と比較し、いずれも保持力が高くなり(架橋による凝集力の向上に基づく)、粘着力、プローブタックはほぼ維持されていることがわかる。
【0035】
次に、これらのサンプルを5人のパネラーの前腕内側部に貼付し、3時間経過後に剥離し粘着剤の皮膚への残存状況について確認した。結果を表1にあわせて示す。
架橋剤を添加した場合、いずれの配合も高分子鎖の凝集性の向上により皮膚への糊残りが減少し、良好な結果を示した。これは保持力測定の結果からもサポートされると考えられる。
【0036】
【表1】
【0037】
【発明の効果】
本発明によれば、シリコーン粘着剤が本来有する粘着物性を維持したまま、保持力を向上させた皮膚貼付材用シリコーン粘着剤組成物及び皮膚貼付材を提供することができる。
【0038】
本発明は、従来の過酸化物によるオルガノシロキサン系ポリマーの架橋などと比較し、皮膚刺激の原因となる分解物(安息香酸など)の発生がない。また、本発明では、オルガノシロキサン系ポリマーの末端を架橋するので、分子鎖のフレキシビリティーが維持され、粘着物性の変化が少ない。この結果、従来の未架橋シリコーン粘着剤でも良好であった粘着性、タックを維持したまま、問題である保持力を向上させることができ、皮膚貼付材用シリコーン粘着剤としてバランスのとれた組成物となる。[0001]
TECHNICAL FIELD OF THE INVENTION
TECHNICAL FIELD The present invention relates to a silicone adhesive composition for a skin patch and a skin patch using the same.
[0002]
[Prior art]
Silicone pressure-sensitive adhesives are used for application to the human body because of their breathability and low skin irritation. In consideration of the adhesive properties at the time of sticking, these may be used by being crosslinked using a peroxide or a platinum catalyst, or may be used without being crosslinked (for example, Patent Document 1).
[0003]
However, when crosslinked by the method described above, sufficient holding power is exhibited, but the adhesive physical properties (tack, adhesive strength) originally possessed by the silicone adhesive are reduced, and the suitability as a pressure sensitive adhesive for human body is reduced. Sometimes. On the other hand, when the crosslinking is not performed, the holding power is insufficient, and the adhesive remains on the skin surface after peeling.
[Patent Document 1]
JP-A-3-200885
[Problems to be solved by the invention]
An object of the present invention is to provide a silicone adhesive composition for a skin adhesive and a skin adhesive having an improved holding force while maintaining the inherent adhesive properties (high adhesiveness to the skin and tackiness) inherent in the silicone adhesive. Is to do.
[0005]
[Means for Solving the Problems]
The present inventor has conducted intensive studies to solve the above problems, and as a result, by reacting an organosiloxane polymer having a hydroxyl group at a terminal with a crosslinking agent capable of reacting with the hydroxyl group, the It has been found that cross-linking can be appropriately performed while maintaining the flexibility of the molecular chain, and as a result, it is possible to improve the holding power while maintaining the inherent adhesive properties of the silicone adhesive, thereby completing the present invention. Reached.
[0006]
That is, the present invention includes the following inventions.
(1) It contains 100 parts by mass of an organosiloxane polymer having a hydroxyl group at a terminal, and 0.1 to 15 parts by mass of a crosslinking agent capable of reacting with the hydroxyl group, and further contains 0 to 10 parts by mass of an acrylic polymer as required. A silicone pressure-sensitive adhesive composition for a skin patch containing the composition.
(2) A skin adhesive material comprising a support and a skin adhesive layer laminated on one surface of the support, wherein the adhesive layer is formed by crosslinking the silicone adhesive composition according to (1). A skin patch that has been made.
(3) An emergency bandage which is provided with a liquid-absorbent pad in a central region of the surface of the pressure-sensitive adhesive layer in the skin patch according to (2).
[0007]
BEST MODE FOR CARRYING OUT THE INVENTION
The present invention is characterized in that an organosiloxane polymer is appropriately crosslinked by reacting with a crosslinking agent capable of reacting with a hydroxyl group.
[0008]
Examples of the organosiloxane-based polymer used in the present invention include those described in JP-A-3-200885, JP-A-2001-11423, and JP-A-2002-200160.
Specifically, general formula (I):
[0009]
Embedded image
(In the formula, R 1 and R 2 each represent a methyl group or a phenyl group, and n represents an integer.)
The organosiloxane rubber component represented by the general formula (II):
[0010]
Embedded image
(In the formula, m represents an integer.)
And an organosiloxane-based polymer obtained by blending a silicone resin represented by the following formula and subjecting it to dehydration condensation.
[0011]
It is also preferable to use, as the silicone resin other than the general formula (II), a branched polyorganosiloxane having three or more hydroxyl groups bonded to a silicon atom in a molecule, alone or in combination.
[0012]
In the general formula (I), R 1 and R 2 are each a methyl group or a phenyl group. However, in order to impart heat resistance or the like to the pressure-sensitive adhesive layer, the molar ratio between the methyl group and the phenyl group (methyl group / Phenyl group) is preferably 25/75 to 98/2, particularly preferably 85/15 to 95/5.
[0013]
In addition, an organosiloxane rubber component represented by the above formula (I) (hereinafter referred to as “component (1)”) and a silicone resin represented by the above formula (II) or a hydroxyl group bonded to the silicon atom are contained in a molecule. The silicone pressure-sensitive adhesive obtained by a partial condensation reaction with a branched polyorganosiloxane having three or more (hereinafter, referred to as "component (2)") has a hydroxyl group bonded to a silicon atom in a molecule of 0.1 to 0.1%. The content is preferably 0.9% by mass. More preferably, it is 0.2 to 0.7% by mass. In this range, the adhesive property is particularly excellent in stability over time.
[0014]
As such a silicone pressure-sensitive adhesive, for example, 355 manufactured by Dow Corning Co .; PSA518, PSA590, PSA595, PSA6574 manufactured by General Electric; YR3340 and XR37-B6722 manufactured by GE Toshiba Silicone Co., Ltd. are commercially available. Commercial products can be used.
[0015]
The silicone pressure-sensitive adhesive composition of the present invention contains a crosslinking agent capable of reacting with a terminal hydroxyl group of the organosiloxane polymer. Examples of such a crosslinking agent include a polyfunctional crosslinking agent having two or more functional groups capable of reacting with a terminal hydroxyl group. A crosslinking agent that is not generally used for crosslinking via a hydroxyl group such as an organic peroxide does not correspond to the crosslinking agent capable of reacting with a hydroxyl group in the present invention.
[0016]
Examples of the functional group capable of reacting with the terminal hydroxyl group of the organosiloxane polymer include an isocyanato group, a glycidyl group, and a carboxyl group.
Specific examples of the polyfunctional crosslinking agent include an isocyanate compound, an epoxy compound, and a carboxylic acid compound.
[0017]
Examples of the isocyanate compound include tolylene diisocyanate, hydrogenated tolylene diisocyanate, tolylene diisocyanate adduct of trimethylolpropane, xylylene diisocyanate adduct of trimethylolpropane, triphenylmethane triisocyanate, and methylene bis (4- (Phenylmethane) triisocyanate, isophorone diisocyanate, and the like, and ketoxime blocks, phenol blocks, and isocyanurates thereof.
[0018]
Examples of the epoxy compound include bisphenol A / epichlorohydrin type epoxy resin, ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, glycerin di or triglycidyl ether, 1,6-hexanediol diglycidyl ether, and trimethylolpropane triglycidyl ether. , Diglycidylaniline, diglycidylamine, N, N, N ', N'-tetraglycidyl-m-xylenediamine, 1,3-bis (N, N'-diglycidylaminomethyl) cyclohexane and the like.
Examples of the carboxylic acid compound include adipic acid, sebacic acid, fumaric acid, maleic acid, and phthalic acid.
[0019]
The compounding amount of the crosslinking agent is 0.1 to 15 parts by mass, preferably 0.2 to 13 parts by mass, more preferably 0.4 to 12 parts by mass based on 100 parts by mass of the organosiloxane polymer. When the amount is less than 0.1 part by mass, the crosslinked structure of the organosiloxane polymer is not sufficiently formed, and the effect of improving the holding power cannot be obtained. On the other hand, when the amount exceeds 15 parts by mass, the holding power is improved. However, the adhesive strength and tackiness may decrease due to excessive crosslinking.
[0020]
The silicone pressure-sensitive adhesive composition of the present invention may optionally contain an acrylic polymer. The compounding amount is preferably 10 parts by mass or less based on 100 parts by mass of the organosiloxane polymer. When the blending amount of the acrylic polymer exceeds 10 parts by mass, there is a problem that physical properties and water resistance of the silicone pressure-sensitive adhesive decrease due to layer separation.
[0021]
The alkyl (meth) acrylate used as the main component of the raw material monomer of the acrylic polymer is not particularly limited, but usually, the alkyl group constituting the ester group is an alkyl group having 1 to 18 carbon atoms. Certain types of alkyl acrylates or alkyl methacrylates can be used, and specifically, methyl acrylate, ethyl acrylate, propyl acrylate, n-butyl acrylate, isobutyl acrylate, 2-ethylhexyl acrylate, acrylic acid Examples thereof include isooctyl, methyl methacrylate, ethyl methacrylate, propyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, 2-ethylhexyl methacrylate, and isooctyl methacrylate.
[0022]
In the present invention, as the monomer constituting the acrylic polymer, the above-mentioned (meth) acrylic acid alkyl ester may be used alone or in combination of two or more kinds, and other copolymerizable monomers may be used. You may use together. Other copolymerizable monomers include vinyl acetate, styrene, acrylonitrile, acrylamide, dimethylacrylamide, acrylic acid, methacrylic acid, 2-hydroxyethyl acrylate, glycidyl methacrylate, 4-hydroxybutyl acrylate, N- Any of various monomers known as monomers for modifying acrylic pressure-sensitive adhesives such as vinylpyrrolidone can be used.
[0023]
The polymerization of these monomers is carried out by ordinary polymerization methods such as solution polymerization, emulsion polymerization, bulk polymerization and the like. The polymerization reaction temperature is usually 50 to 85 ° C, preferably 60 to 80 ° C.
[0024]
When performing solution polymerization, the solid content is usually 0.5 to 60% by mass, preferably 5 to 50% by mass in a solvent such as acetone, benzene, toluene, ethyl acetate, hexane, heptane, methanol, ethanol and isopropanol. % By using a polymerization initiator such as azobisisobutyronitrile and benzoyl peroxide.
The amount (solid content) of the polymerization initiator is usually 0.05 to 1 part by mass based on 100 parts by mass of the acrylic polymer (solid content).
[0025]
The pressure-sensitive adhesive composition of the present invention may contain, if necessary, a softener such as process oil, polyisobutylene, or polybutene; a filler such as titanium oxide, zinc oxide, aluminum metasilicate, calcium carbonate, or calcium phosphate; starch, or a cellulose derivative. , A water retention function imparting agent such as polyvinyl alcohol; and liquid paraffin.
[0026]
When using the pressure-sensitive adhesive composition of the present invention, a solution dissolved in an organic solvent such as toluene, ethyl acetate, methyl ethyl ketone, or acetone is applied to a support or a film such as a release film, and then 30 to 170 ° C., preferably 40 to 170 ° C. Crosslinking by drying at a drying temperature of ~ 150 ° C gives its adhesive properties.
[0027]
The support used for the skin patch or the first-aid adhesive plaster of the present invention has an adhesive layer comprising the above-mentioned adhesive composition laminated and held on one surface. Specific materials include polystyrene-based thermoplastic elastomer films, polyolefin-based films such as polyethylene, polypropylene, ethylene / methacrylic acid copolymer, and ethylene / methyl methacrylate, polyurethane-based films, polyester-based films, and various plastic materials. , A nonwoven fabric, a knitted fabric, a paper, a laminate of these films, a laminate of papers, or the like.
[0028]
The thickness of the support is arbitrary depending on the material. Usually, when the film is used as the support, the thickness is 15 to 250 μm, preferably about 30 to 100 μm. Is about 50 to 500 μm, preferably about 100 to 300 μm.
[0029]
The skin patch and the emergency plaster of the present invention are obtained by laminating an adhesive layer having a specific composition on one surface of a support. Lamination can be performed by applying the pressure-sensitive adhesive composition, and this coating can be performed directly or by a transfer coating method according to a general coating method.
[0030]
Further, when a film made of a material having no moisture permeability is used as the support used in the present invention, when the film is applied to the skin surface for a long time, the applied portion may be moistened, and as a result, skin rash may occur. . Therefore, even when such a support is used or when a support having moisture permeability is used, it is preferable to perforate the support and the pressure-sensitive adhesive layer in order to further impart moisture permeability. To perform the perforation treatment, a method using a perforation roll, a method such as punching or laser irradiation can be used, and the hole diameter is about 0.2 to 2 mm.
[0031]
Further, in the present invention, an emergency adhesive plaster can be provided by providing a liquid-absorbent pad in the central region of the surface of the pressure-sensitive adhesive layer of the skin patch obtained as described above. As the absorbent pad, for example, gauze, cotton cloth, nonwoven fabric, a composite product of absorbent cotton and nonwoven fabric, a composite product of absorbent cotton and a knitted net, and the like can be used to absorb exudate from the wound site and furthermore, Is preferred.
[0032]
In order to prevent contamination of the surface of the pressure-sensitive adhesive layer, the surface of the pressure-sensitive adhesive layer is preferably coated with a release material until the surface of the pressure-sensitive adhesive layer is used in the skin adhesive material and the first-aid bandage of the present invention. In this case, the release material used is a fluorine-based silicone or a methyl-based silicone for the release material in order to improve the releasability from the adhesive layer containing the organosiloxane polymer on paper, polyolefin laminated paper, polyester film, or the like. It is preferable to use one coated with.
[0033]
【Example】
Hereinafter, the present invention will be described more specifically with reference to Examples and Comparative Examples, but these do not limit the scope of the present invention at all. In the following, parts mean parts by mass, and% means mass%.
[Example 1]
To 100 parts (solid content) of a methylphenyl silicone pressure-sensitive adhesive (XR37-B6722, manufactured by GE Toshiba Silicone), 3 parts (solid content) of a trifunctional isocyanate-based cross-linking agent (Coronate HL, manufactured by Nippon Polyurethane) is added, followed by sufficient stirring. did. Next, it is coated on a release paper for silicone adhesive (Binasheet 70XT-032HK-H, manufactured by Fujimori Kogyo Co., Ltd.) so that the coating amount after drying is 40 g / m 2, and dried with hot air at 100 ° C. for 3 minutes. did. After drying, a 25 μm-thick polyethylene terephthalate (PET) film (Lumirror, manufactured by Toray Industries, Inc.) was laminated to form an adhesive sheet. [Example 2]
An adhesive sheet was prepared in the same manner as in Example 1 except that the amount of the crosslinking agent was changed to 6 parts.
[Example 3]
An adhesive sheet was prepared in the same manner as in Example 1 except that the amount of the crosslinking agent was changed to 12 parts.
[Example 4]
Example 1 except that N, N, N ', N'-tetraglycidyl-m-xylylenediamine (TETRAD-X, manufactured by Mitsubishi Gas Chemical) was used as a crosslinking agent and the blending amount was 0.4 part (solid content). An adhesive sheet was prepared in the same manner as described above.
[Example 5]
A trifunctional isocyanate-based cross-linking agent (Coronate HL, manufactured by Nippon Polyurethane) was used as the cross-linking agent, and a compounding amount of 3 parts (solid content) was further added to an acrylic polymer (n-butyl acrylate 99 parts by mass, acrylic acid 10 parts by mass (solid content) of a mixture of 1 part by mass of 4-hydroxybutyl, 0.25 parts by mass of azobisisobutyronitrile and 130 parts by mass of ethyl acetate polymerized at 65 ° C. for 12 hours in a nitrogen gas atmosphere. ) Was added to prepare an adhesive sheet in the same manner as in Example 1.
[0034]
[Comparative Example 1]
An adhesive sheet was prepared in the same manner as in Example 1 except that no crosslinking agent was added. With respect to the pressure-sensitive adhesive sheets of Examples 1 to 5 and Comparative Example 1, the adherend was a phenol resin plate, and the pressure-sensitive adhesive strength and probe tack were measured according to JIS Z0237. Further, the holding force at 40 ° C. (substrate to be adhered SUS) was measured as the falling time of the weight using a creep tester. Table 1 shows the composition and measurement results. From Table 1, it can be seen that, as compared with the uncrosslinked one (Comparative Example 1), the holding power was higher (based on the improvement of the cohesive force due to crosslinking), and the adhesive strength and the probe tack were almost maintained.
[0035]
Next, these samples were affixed to the inner parts of the forearms of five panelists, peeled off after 3 hours, and the state of the adhesive remaining on the skin was confirmed. The results are shown in Table 1.
In the case where a crosslinking agent was added, in any of the formulations, adhesive residue on the skin was reduced due to improvement in the cohesiveness of the polymer chains, and good results were obtained. This is considered to be supported by the results of the holding force measurement.
[0036]
[Table 1]
[0037]
【The invention's effect】
ADVANTAGE OF THE INVENTION According to this invention, the silicone adhesive composition for skin adhesives and the skin adhesives which improved holding power can be provided, maintaining the adhesive physical property which a silicone adhesive has originally.
[0038]
The present invention does not generate decomposition products (such as benzoic acid) that cause skin irritation, as compared with conventional crosslinking of an organosiloxane polymer with a peroxide. In the present invention, the terminal of the organosiloxane polymer is crosslinked, so that the flexibility of the molecular chain is maintained and the change in the adhesive properties is small. As a result, while maintaining the tackiness and tackiness which were good even with the conventional non-crosslinked silicone pressure-sensitive adhesive, the problematic holding power can be improved, and the composition is well-balanced as a silicone pressure-sensitive adhesive for skin patches. It becomes.
Claims (3)
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JP2007031333A (en) * | 2005-07-26 | 2007-02-08 | Hisamitsu Pharmaceut Co Inc | Pressure-sensitive adhesive and plaster |
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