JPH03220120A - Acrylic gel material and acrylic gel preparation - Google Patents
Acrylic gel material and acrylic gel preparationInfo
- Publication number
- JPH03220120A JPH03220120A JP2237382A JP23738290A JPH03220120A JP H03220120 A JPH03220120 A JP H03220120A JP 2237382 A JP2237382 A JP 2237382A JP 23738290 A JP23738290 A JP 23738290A JP H03220120 A JPH03220120 A JP H03220120A
- Authority
- JP
- Japan
- Prior art keywords
- acrylic
- parts
- liquid component
- gel
- acrylic acid
- 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
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 238000002360 preparation method Methods 0.000 title claims abstract description 38
- 239000000463 material Substances 0.000 title claims abstract description 28
- 239000007788 liquid Substances 0.000 claims abstract description 36
- 229920000642 polymer Polymers 0.000 claims abstract description 36
- 229940079593 drug Drugs 0.000 claims abstract description 33
- 239000003814 drug Substances 0.000 claims abstract description 33
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 20
- 238000004132 cross linking Methods 0.000 claims description 15
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 239000003431 cross linking reagent Substances 0.000 claims description 9
- 239000012948 isocyanate Substances 0.000 claims description 7
- 150000002513 isocyanates Chemical class 0.000 claims description 7
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- -1 acrylic ester Chemical class 0.000 abstract description 23
- 239000000178 monomer Substances 0.000 abstract description 16
- 206010040880 Skin irritation Diseases 0.000 abstract description 9
- 231100000475 skin irritation Toxicity 0.000 abstract description 9
- 230000036556 skin irritation Effects 0.000 abstract description 9
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 4
- 229920001577 copolymer Polymers 0.000 abstract description 3
- 150000002334 glycols Chemical class 0.000 abstract description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 2
- 239000000758 substrate Substances 0.000 abstract 2
- 239000003925 fat Substances 0.000 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- 239000010410 layer Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 25
- 230000000052 comparative effect Effects 0.000 description 22
- 229920006222 acrylic ester polymer Polymers 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 238000009472 formulation Methods 0.000 description 11
- 239000000523 sample Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 9
- 239000000853 adhesive Substances 0.000 description 8
- 230000001070 adhesive effect Effects 0.000 description 8
- OQILCOQZDHPEAZ-UHFFFAOYSA-N octyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OCCCCCCCC OQILCOQZDHPEAZ-UHFFFAOYSA-N 0.000 description 8
- 239000004745 nonwoven fabric Substances 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 6
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 238000004299 exfoliation Methods 0.000 description 5
- 229920002367 Polyisobutene Polymers 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 238000004873 anchoring Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 229920002635 polyurethane Polymers 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
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- 102000011782 Keratins Human genes 0.000 description 3
- 108010076876 Keratins Proteins 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 210000000736 corneocyte Anatomy 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 239000005001 laminate film Substances 0.000 description 3
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 3
- 229960001597 nifedipine Drugs 0.000 description 3
- 150000001451 organic peroxides Chemical class 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002759 woven fabric Substances 0.000 description 3
- GLXBPZNFNSLJBS-UHFFFAOYSA-N 11-methyldodecyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCCCCCCCCCCC(C)C GLXBPZNFNSLJBS-UHFFFAOYSA-N 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- KANZWHBYRHQMKZ-UHFFFAOYSA-N 2-ethenylpyrazine Chemical compound C=CC1=CN=CC=N1 KANZWHBYRHQMKZ-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 229920001342 Bakelite® Polymers 0.000 description 2
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 230000037374 absorbed through the skin Effects 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 239000004637 bakelite Substances 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229960002896 clonidine Drugs 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical compound CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 2
- 229960000991 ketoprofen Drugs 0.000 description 2
- 229940105132 myristate Drugs 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 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 2
- 239000000123 paper Substances 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000012192 staining solution Substances 0.000 description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- CTWLAMKOJQOQLN-UHFFFAOYSA-N tridecyl tetradecanoate Chemical compound CCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC CTWLAMKOJQOQLN-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 1
- DCRYNQTXGUTACA-UHFFFAOYSA-N 1-ethenylpiperazine Chemical compound C=CN1CCNCC1 DCRYNQTXGUTACA-UHFFFAOYSA-N 0.000 description 1
- PBGPBHYPCGDFEZ-UHFFFAOYSA-N 1-ethenylpiperidin-2-one Chemical compound C=CN1CCCCC1=O PBGPBHYPCGDFEZ-UHFFFAOYSA-N 0.000 description 1
- BFYSJBXFEVRVII-UHFFFAOYSA-N 1-prop-1-enylpyrrolidin-2-one Chemical compound CC=CN1CCCC1=O BFYSJBXFEVRVII-UHFFFAOYSA-N 0.000 description 1
- VFFDVELHRCMPLY-UHFFFAOYSA-N 12-methyltridecan-1-amine Chemical compound CC(C)CCCCCCCCCCCN VFFDVELHRCMPLY-UHFFFAOYSA-N 0.000 description 1
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- PGMMQIGGQSIEGH-UHFFFAOYSA-N 2-ethenyl-1,3-oxazole Chemical compound C=CC1=NC=CO1 PGMMQIGGQSIEGH-UHFFFAOYSA-N 0.000 description 1
- MZNSQRLUUXWLSB-UHFFFAOYSA-N 2-ethenyl-1h-pyrrole Chemical compound C=CC1=CC=CN1 MZNSQRLUUXWLSB-UHFFFAOYSA-N 0.000 description 1
- ZDHWTWWXCXEGIC-UHFFFAOYSA-N 2-ethenylpyrimidine Chemical compound C=CC1=NC=CC=N1 ZDHWTWWXCXEGIC-UHFFFAOYSA-N 0.000 description 1
- GASMGDMKGYYAHY-UHFFFAOYSA-N 2-methylidenehexanamide Chemical compound CCCCC(=C)C(N)=O GASMGDMKGYYAHY-UHFFFAOYSA-N 0.000 description 1
- SKVCWXRLKHBEKW-UHFFFAOYSA-N 2-methylpropyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCC(C)C SKVCWXRLKHBEKW-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- MXRGSJAOLKBZLU-UHFFFAOYSA-N 3-ethenylazepan-2-one Chemical compound C=CC1CCCCNC1=O MXRGSJAOLKBZLU-UHFFFAOYSA-N 0.000 description 1
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- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ONKUXPIBXRRIDU-UHFFFAOYSA-N Diethyl decanedioate Chemical compound CCOC(=O)CCCCCCCCC(=O)OCC ONKUXPIBXRRIDU-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000004129 EU approved improving agent Substances 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 206010016322 Feeling abnormal Diseases 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
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- 229920003182 Surlyn® Polymers 0.000 description 1
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- 125000002723 alicyclic group Chemical group 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 230000000147 hypnotic effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical class CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920006298 saran Polymers 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 231100001068 severe skin irritation Toxicity 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000004962 sulfoxyl group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は皮膚面に貼付して皮膚面の保護なとに用いるア
クリル系ゲル材、および皮膚を通して薬物を生体内へ連
続的に投与するためのアクリル系ゲル製剤に関する。[Detailed Description of the Invention] <Industrial Application Field> The present invention relates to an acrylic gel material that is applied to the skin surface and used to protect the skin surface, and for continuous administration of drugs into living bodies through the skin. The present invention relates to an acrylic gel formulation.
〈従来の技術〉
近年、薬物を皮膚面を通して生体内へ投与するための経
皮吸収製剤としてハップ剤やテープ剤なとの皮膚面貼付
型の外用剤が種々開発されている。<Prior Art> In recent years, various skin-applied external preparations such as poultices and tapes have been developed as transdermal absorption preparations for administering drugs into living bodies through the skin.
このような貼付型製剤は適用皮膚面に製剤を確実に固定
させる目的で、通常、製剤の皮膚接触部分に比較的強接
着力を有する皮膚面固定用の粘着剤層が設けられていた
り、強接着性の粘着シートで製剤全体をオーバーコート
し、このシートの接着力によって皮膚固定を行なってい
る。In order to securely fix the preparation to the skin surface to which it is applied, such patch-type preparations usually have an adhesive layer on the skin-contacting part of the preparation that has a relatively strong adhesion force for fixation to the skin surface. The entire formulation is overcoated with an adhesive sheet, and the adhesive force of this sheet is used to fix it on the skin.
〈発明が解決しようとする課題〉
しかし、貼付型の経皮吸収製剤は、薬物の皮膚移行を良
好にするために確実に皮膚面に固定する必要がある反面
、皮膚接着力があまり大きすぎると、使用後に皮膚面か
ら製剤を剥離除去するときに物理的刺激による痛みや角
質剥離を生し、時には著しい皮膚刺激を生しる場合もあ
る。<Problem to be solved by the invention> However, patch-type transdermal absorption preparations need to be firmly fixed to the skin surface in order to improve the transdermal transfer of the drug, but on the other hand, if the skin adhesive force is too large, When the preparation is peeled off and removed from the skin after use, physical irritation may cause pain and exfoliation, and sometimes severe skin irritation may occur.
従って、皮膚接着性は貼付撃の経皮吸収製剤を開発する
に当たって実用上、重要な検討項目ではあるか、皮膚刺
激性についての検討も重要であり、皮膚刺激性か小さく
かつ製剤の皮膚固定も良好な製剤の開発か望まれている
のか実情である。Therefore, skin adhesion is an important consideration from a practical point of view when developing patch transdermal absorption preparations, and skin irritation is also important. The actual situation is whether the development of good formulations is desired.
〈課題を解決するための手段〉
そこで、本発明者らは上記課題を解決するために鋭意研
究を重ねた結果、アクリル酸エステル系ポリマーに該ポ
リマーと相溶する液体成分を通常の使用量よりも過剰に
含有させた場合、皮膚への接着においてはソフト感か付
与できる反面、凝集力か極度に低下するのて、著しい凝
集破壊か生して皮膚面から剥離する際に剥離不可能とな
ったり、皮膚刺激を起こすことを見い出し、実用に耐え
ないことか判明した。そこで、液体成分を過剰量含有さ
せたポリマー層を架橋処理してゲル化させ、所謂油性ゲ
ル状態にしたところ、凝集力の低下か防げると共に製剤
の剥離時に皮膚面にかかる応力を緩和・分散でき、皮膚
接着性と皮膚刺激性のバランスか良好となることを見い
出し、本発明を完成するに至った。<Means for Solving the Problems> Therefore, the present inventors have conducted extensive research to solve the above problems, and have found that a liquid component compatible with the acrylic ester polymer is added to the acrylic ester polymer in a larger amount than the usual amount. If it is added in excess, it can give a soft feel when adhering to the skin, but the cohesive force is extremely reduced, leading to significant cohesive failure and making it impossible to peel off from the skin surface. It was also found that the product caused skin irritation, making it impractical for practical use. Therefore, by cross-linking a polymer layer containing an excessive amount of a liquid component to form a so-called oily gel, it is possible to prevent the cohesive force from decreasing and also to alleviate and disperse the stress applied to the skin surface when the preparation is peeled off. The present inventors have discovered that a good balance between skin adhesion and skin irritation can be achieved, leading to the completion of the present invention.
即ち、本発明はアクリル酸エステル系ポリマーおよび該
ポリマーと相溶する液体成分とを含む架橋ゲル層か支持
体の少なくとも片面に形成されてなるアクリル系ゲル材
、および該ゲル材に薬物を含有させてなるアクリル系ゲ
ル製剤を提供するものである。That is, the present invention provides an acrylic gel material formed on at least one side of a crosslinked gel layer or support containing an acrylic acid ester polymer and a liquid component compatible with the polymer, and a drug contained in the gel material. The present invention provides an acrylic gel formulation consisting of:
本発明のアクリル系ゲル材およびゲル製剤に用いる支持
体は、特に限定されないか、架橋ゲル層に含有される液
体成分や薬物が支持体中を通って背面から失われて含量
低下を起こさないもの、即ちこれらの成分か不透過性の
材質からなるものが好ましい。具体的にはポリエステル
、ナイロン、サラン、ポリエチレン、ポリプロピレン、
エチレン−酢酸ビニル共重合体、ポリ塩化ビニル、エチ
レン−アクリル酸エチル共重合体、ポリテトラフルオロ
エチレン、サーリン、金属箔なとの単独フィルムまたは
これらのラミネートフィルムなとを用いることかできる
。これらのうち、支持体と後述の架橋ゲル層との間の接
着性（投錨力）を向上させるために、支持体を上記材質
からなる無孔ソートと多孔フィルムとのラミネートフィ
ルムとし、多孔ソート側に架橋ゲル層を形成することか
好ましい。The support used for the acrylic gel material and gel formulation of the present invention is not particularly limited, or it is one that does not cause a content reduction due to the liquid component or drug contained in the crosslinked gel layer passing through the support and being lost from the back side. That is, it is preferable that these components are made of impermeable materials. Specifically, polyester, nylon, saran, polyethylene, polypropylene,
A single film of ethylene-vinyl acetate copolymer, polyvinyl chloride, ethylene-ethyl acrylate copolymer, polytetrafluoroethylene, Surlyn, metal foil or a laminate film of these can be used. Among these, in order to improve the adhesion (anchoring force) between the support and the crosslinked gel layer described below, the support is made of a laminate film of a non-porous sort made of the above material and a porous film, and the porous sort side is It is preferable to form a crosslinked gel layer.
このような多孔フィルムとしては、架橋ゲル層との投錨
力か向上するものであれば特に限定されず、例えば紙、
織布、不織布、機械的に穿孔処理したシートなどが挙げ
られ、特に紙、織布、不織布か好ましい。多孔フィルム
の厚みは投錨力向上およびゲル材やゲル製剤全体の柔軟
性を考慮すると１０〜５００μｍ、プラスタータイプや
粘着テープタイプのような薄手の製剤の場合は１０〜２
００μｍの範凹とする。Such a porous film is not particularly limited as long as it can improve the anchoring force with the cross-linked gel layer, such as paper,
Examples include woven fabrics, nonwoven fabrics, mechanically perforated sheets, and paper, woven fabrics, and nonwoven fabrics are particularly preferred. The thickness of the porous film is 10 to 500 μm considering the improvement of anchoring ability and the flexibility of the gel material and gel preparation as a whole, and 10 to 2 μm for thin preparations such as plaster type or adhesive tape type.
The range concavity is 00 μm.
また、多孔フィルムとして織布や不織布を用いる場合、
目付量を５〜３０ｇ／ｒｒｌ、好ましくは８〜２０ｇ／
ｉとすることか投錨力の向上の点から好ましいものであ
る。In addition, when using woven fabric or non-woven fabric as the porous film,
The basis weight is 5 to 30 g/rrl, preferably 8 to 20 g/rrl.
It is preferable to set it to i from the point of view of improving the anchoring power.
本発明において上記支持体の片面に形成される架橋ゲル
層は、アクリル酸エステル系ポリマーおよび該ポリマー
と相溶する液体成分および製剤としてはさらに薬物を含
有した架橋構造を存する層であり、適度な皮膚接着力と
凝集力とを備えている。接着力としてはベークライト板
への接着力（測定方法は後述する）で７０〜２５０ｇ／
１２ｍｍ幅、プローブタック試験で２０〜８０ｇ程度の
値を示すものである。In the present invention, the crosslinked gel layer formed on one side of the support is a layer having a crosslinked structure containing an acrylic acid ester polymer, a liquid component compatible with the polymer, and a drug as a preparation. It has skin adhesive strength and cohesive strength. The adhesive strength to Bakelite plate is 70 to 250 g/g (measurement method will be described later).
It has a width of 12 mm and exhibits a value of about 20 to 80 g in a probe tack test.
アクリル酸エステル系ポリマーは後述の液体成分と共に
架橋ゲル層を構成する主基材となるものであって、液体
成分と相溶状態を維持して皮膚面への良好な接着性と保
型性を発揮するものである。The acrylic ester polymer is the main base material that constitutes the crosslinked gel layer together with the liquid component described below, and maintains a compatible state with the liquid component to provide good adhesion and shape retention to the skin surface. It is something that can be demonstrated.
なお、天然ゴムや合成ゴムなどのゴム系、シリコーン系
のポリマーでは本発明に用いる液体成分との相溶性が充
分でなかったり、薬物の溶解性や放出性が著しく低かっ
たりするので好ましくない。Note that rubber-based polymers such as natural rubber and synthetic rubber, and silicone-based polymers are not preferred because they do not have sufficient compatibility with the liquid component used in the present invention or have extremely low drug solubility and release properties.
また、このようなポリマーはアクリル酸エステル系ポリ
マーと比べて架橋反応に関与する官能基量などの調整が
難しく、再現性のある架橋処理を行ない難いという問題
があり、本発明に適したちのとは云えない。In addition, compared to acrylic acid ester polymers, such polymers have the problem that it is difficult to adjust the amount of functional groups involved in the crosslinking reaction, and it is difficult to perform crosslinking treatment with reproducibility. I can't say that.
本発明に用いるアクリル酸エステル系ポリマーとしては
、アルキル基の炭素数か４以上の（メタ）アクリル酸ア
ルキルエステルの重合体か好ましく、特に架橋処理のし
易さの点からは該（メタ）アクリル酸アルキルエステル
を主成分として共重合した共重合体を用いることが望ま
しい。The acrylic acid ester polymer used in the present invention is preferably a polymer of (meth)acrylic acid alkyl ester having an alkyl group with a carbon number of 4 or more. It is desirable to use a copolymer copolymerized with an acid alkyl ester as a main component.
（メタ）アクリル酸アルキルエステルとしては、具体的
にはアルキル基かブチル、ペンチル、ヘキシル、ヘプチ
ル、オクチル、ノニル、デシル、ウンデシル、ドデシル
、トリデシルなとの直鎖アルキル基や分岐アルキル基な
とを有する（メタ）アクリル酸アルキルエステルか挙げ
られ、これらは一種もしくは二種以上用いることかでき
る。また、上記（メタ）アクリル酸アルキルエステルと
共重合するモノマーとしては、例えば（メタ）アクリル
酸、イタコン酸、マレイン酸、無水マレイン酸なとのカ
ルボキシル基含有モノマー、スチレンスルホン酸、了り
ルスルホン酸、スルホプロピル（メタ）アクリレート、
（メタ）アクリロイルオキシナフタレンスルホン酸、ア
クリルアミドメチルプロパンスルホン酸などのスルホキ
シル基含有モノマー （メタ）アクリル酸ヒドロキシエ
チルエステル、（メタ）アクリル酸ヒドロキシプロピル
エステルなとのヒドロキシル基含有モノマー （メタ）
アクリルアミド、ジメチル（メタ）アクリルアミド、Ｎ
−ブチルアクリルアミド、Ｎ−メチロール（メタ）アク
リルアミド、Ｎ−メチロールプロパン（メタ）アクリル
アミドなとのアミド基含有モノマー （メタ）アクリル
酸アミノエチルエステル、（メタ）アクリル酸ジメチル
アミノエチルエステル、（メタ）アクリル酸ｔｅｒｔ−
ブチルアミノエチルエステルなとのアルキルアミノアル
キル基含有モノマー （メタ）アクリル酸メトキシエチ
ルエステル、（メタ）アクリル酸エトキシエチルエステ
ルなとの（メタ）アクリル酸アルコキシアルキルエステ
ル、（メタ）アクリル酸テトラヒドロフルフリルエステ
ル、（メタ）アクリル酸メトキシエチレングリコールエ
ステル、（メタ）アクリル酸メトキシジエチレングリコ
ールエステル、（メタ）アクリル酸メトキシポリエチレ
ングＪコールエステル、（メタ）アクリル酸メトキシポ
リプロピレングリコールエステルなとのアルコキン基（
または側鎖にエーテル結合）含有（メタ）アクリル酸エ
ステル、（メタ）アクリロニトリル、酢酸ビニル、プロ
ピオン酸ビニル、Ｎ−ビニル−２−ピロリドン、メチル
ビニルピロリドン、ビニルピリジン、ビニルピペリドン
、ビニルピリミジン、ビニルピペラジン、ビニルピラジ
ン、ビニルピロール、ビニルイミダゾール、ビニルカプ
ロラクタム、ビニルオキサゾール、ビニルモルホリンな
どのビニル系モノマーなどが挙げられ、これらは一種も
しくは二種以上併用して共重合することかできる。これ
らの共重合するモノマーはゲル層の凝集力の調整や、薬
物の溶解性向上のために用いることができ、共重合量は
目的に応じて任意に設定することができる。(Meth)acrylic acid alkyl esters include straight chain alkyl groups and branched alkyl groups such as butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, and tridecyl. Examples include (meth)acrylic acid alkyl esters, and these can be used alone or in combination of two or more. In addition, examples of monomers copolymerized with the above (meth)acrylic acid alkyl esters include carboxyl group-containing monomers such as (meth)acrylic acid, itaconic acid, maleic acid, and maleic anhydride, styrene sulfonic acid, and ester sulfonic acid. , sulfopropyl (meth)acrylate,
Sulfoxyl group-containing monomers such as (meth)acryloyloxynaphthalenesulfonic acid and acrylamide methylpropanesulfonic acid Hydroxyl group-containing monomers such as (meth)acrylic acid hydroxyethyl ester and (meth)acrylic acid hydroxypropyl ester (meth)
Acrylamide, dimethyl(meth)acrylamide, N
-Amide group-containing monomers such as butylacrylamide, N-methylol (meth)acrylamide, N-methylolpropane (meth)acrylamide (meth)acrylic acid aminoethyl ester, (meth)acrylic acid dimethylaminoethyl ester, (meth)acrylic acid acid tert-
Alkylaminoalkyl group-containing monomers such as butylaminoethyl ester (meth)acrylic acid methoxyethyl ester, (meth)acrylic acid alkoxyalkyl ester such as (meth)acrylic acid ethoxyethyl ester, (meth)acrylic acid tetrahydrofurfuryl Alcoquine groups such as ester, (meth)acrylic acid methoxyethylene glycol ester, (meth)acrylic acid methoxydiethylene glycol ester, (meth)acrylic acid methoxypolyethylene glycol ester, (meth)acrylic acid methoxypolypropylene glycol ester, etc.
or ether bond in the side chain)-containing (meth)acrylic ester, (meth)acrylonitrile, vinyl acetate, vinyl propionate, N-vinyl-2-pyrrolidone, methylvinylpyrrolidone, vinylpyridine, vinylpiperidone, vinylpyrimidine, vinylpiperazine, Examples include vinyl monomers such as vinylpyrazine, vinylpyrrole, vinylimidazole, vinylcaprolactam, vinyloxazole, and vinylmorpholine, and these monomers can be used alone or in combination of two or more to be copolymerized. These copolymerizable monomers can be used to adjust the cohesive force of the gel layer and improve the solubility of drugs, and the amount of copolymerization can be arbitrarily set depending on the purpose.
上記アクリル酸エステル系ポリマーのうち、本発明にお
いて好ましく用いられるポリマーとしては、（メタ）ア
クリル酸アルキルエステルと一般式（Ｉ）及び／又は（
ＩＩ）、
ＣＨ，＝ＣＨＸ （Ｉ） ＣＨ２＝ＣＨＲ（ＣＯ
ＯＸ） （ＩＩ）（但し、Ｒは水素原子またはメチ
ル基、Ｘは少なくとも１個の窒素原子または窒素原子と
酸素原子を有する基を示す。）
て表されるモノマーとの共重合体であり、特に架橋点量
の調節や得られるゲル物性の調節の点から、一般式（Ｉ
）、（Ｉ［）のモノマーとしては前記にて例示のカルボ
キシル基含有モノマーやヒドロキシル基含有モノマーの
少なくとも一種を必須成分として、該一般式（Ｉ）、（
ＩＦ）にて表される他のモノマーをさらに共重合する三
種類以上のモノマーの共重合体を用いることか好ましい
。Among the above-mentioned acrylic acid ester-based polymers, the polymers preferably used in the present invention include (meth)acrylic acid alkyl ester and general formula (I) and/or (
II), CH,=CHX (I) CH2=CHR(CO
OX) (II) (wherein, R is a hydrogen atom or a methyl group, and X is at least one nitrogen atom or a group having a nitrogen atom and an oxygen atom.) In particular, the general formula (I
), (I[) includes at least one of the above-exemplified carboxyl group-containing monomers and hydroxyl group-containing monomers as an essential component, and the monomers of the general formula (I), (
It is preferable to use a copolymer of three or more types of monomers which are further copolymerized with other monomers represented by IF).
本発明に用いる液体成分は上記アクリル酸エステル系ポ
リマーと相溶する性質を有するものであり、架橋ゲル層
を可塑化させてソフト感を付与することによって、架橋
ゲル層を皮膚面から剥離するときに皮膚接着力に起因す
る痛みや皮膚刺激性を低減する役割を有するものである
。The liquid component used in the present invention has a property of being compatible with the above-mentioned acrylic acid ester polymer, and by plasticizing the cross-linked gel layer and imparting a soft feeling, it can be used when peeling the cross-linked gel layer from the skin surface. It has the role of reducing pain and skin irritation caused by skin adhesive strength.
従って、この液体成分は可塑化作用を育するものてあれ
ばよいか、併存させる薬物の経皮吸収性を向上させるた
めに吸収促進作用も有するものを用いることか好ましい
。Therefore, it is sufficient that the liquid component has a plasticizing effect, or it is preferable to use a liquid component that also has an absorption-promoting effect in order to improve the transdermal absorption of the coexisting drug.
このような液体成分としては、具体的にはエチレングリ
コール、ジエチレングリコール、トリエチレングリコー
ル、プロピレングリコール、ポリエチレングリコール、
ポリプロピレングリコールのようなグリコール類、オリ
ーブ油、ヒマノ油、スクワしン、ラノリンのような油脂
類、酢酸エチル、エチルアルコール、ジメチルデンルス
ルホキント、メチルオクチルスルホキンド、ソメチルス
ルホキント、ジメチルホルムアミド、ツメチルアセトア
ミド、ジメチルラウリルアミド、ドデシルピロリトン、
イソソルビ］−−ルのような存８１溶剤、液状の界面活
性剤、ジイソプロピルアノベート、フタル酸エステル、
ンエチルセバケートのような可塑剤、流動パラフィンの
ような炭化水素類、エトキノ化ステアリルアルコール、
グリセリンエステル、ミリスチン酸イソプロピル、ミリ
スチン酸イツトリゾノル、ラウリル酸エチル、Ｎ−メチ
ルピロリドン、オレイン酸エチル、オレイン酸、アジピ
ン酸ノイソブロビル、パルミチン酸イソプロピル、バル
ミチン酸オクチル、ｌ、３−ブタンジオールなとか挙げ
られ、これらのうち一種以上を配合して使用する。前記
アクリル酸エステル系ポリマーと該液体成分との配合割
合（含有割合）は、重量比で１．０ ： ０．２５〜１
．０：２．０、皮膚刺激性低減の観屯から好ましくは１
．０ ： ０．４〜１．０ ： １．．８、さらに好ま
しくは１．０：０．６〜１０・１．８、即ち液体成分量
をかなり多量に含有させることか好ましい。なお、従来
の製剤に配合されている液体成分量は通常、１．０：０
．２５よりも液体成分量か少なく、このような含存量で
は実用的な皮膚刺激性低減のレベルに達しないことかあ
る。Specifically, such liquid components include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, polyethylene glycol,
Glycols such as polypropylene glycol, oils and fats such as olive oil, castor oil, squalene, lanolin, ethyl acetate, ethyl alcohol, dimethyldensulfoquine, methyloctylsulfoquine, somethylsulfoquine, dimethylformamide, Methylacetamide, dimethyl laurylamide, dodecylpyrrolitone,
81 solvents such as isosorbyl, liquid surfactants, diisopropyl anovate, phthalate esters,
plasticizers such as ethyl sebacate, hydrocarbons such as liquid paraffin, ethoxylated stearyl alcohol,
Glycerin ester, isopropyl myristate, itutrizonol myristate, ethyl laurate, N-methylpyrrolidone, ethyl oleate, oleic acid, noisobrobyl adipate, isopropyl palmitate, octyl valmitate, l,3-butanediol, etc. One or more of these may be used in combination. The blending ratio (content ratio) of the acrylic ester polymer and the liquid component is 1.0:0.25 to 1 by weight.
．． 0:2.0, preferably 1 from the viewpoint of reducing skin irritation
．． 0: 0.4-1.0: 1. ．． 8, more preferably 1.0:0.6 to 10.1.8, that is, it is preferable to contain a considerably large amount of liquid component. In addition, the amount of liquid components mixed in conventional formulations is usually 1.0:0.
．． The amount of liquid component is smaller than that of No. 25, and such an amount may not reach a practical level of reducing skin irritation.
本発明では以上のように配合したのち、適当な架橋手段
にて架橋処理を施こしてゲル状態とし、含有する液体成
分の流出の防止と凝集力を付与する。架橋処理は紫外線
照射や電子線照射なとの放射線照射による物理的架橋や
、ポリイソシアネート化合物、有機過酸化物、有機金属
塩、金属アルコラート、′ｉ匡キレート化合物、多官能
性化合物なとの架橋剤を用いた化学的架橋処理なとか用
いられる。これらの架橋手段のうち放射線照射や有機過
酸化物を用いた場合、薬動程によっては分解反応を生し
ることかあり、また高反応性のイソシアネート類や、通
常の架橋反応に用いる金属塩や有機金属塩では配合後に
溶液の増粘現象か生して作業性に劣ることかある。また
予めジアクリレートなとの多官能性のモノマーをアクリ
ル酸エステル系ポリマーに共重合させておく方法も考え
られるか、この場合も溶液粘度か上昇する可能性かある
。従って、本発明においてはこれらの架橋剤のうち反応
性や取扱い性の点から、三官能性イソシアネート、チタ
ンまたはアルミニウムからなる金属アルコラート或いは
金属キレート化合物か好適である。これらの架橋剤は塗
工、乾燥までは溶液の増粘現象を起こさず、極めて作業
性に優れる。In the present invention, after being blended as described above, the composition is crosslinked using an appropriate crosslinking means to form a gel state, thereby preventing the liquid components contained therein from flowing out and imparting cohesive force. Crosslinking treatment includes physical crosslinking by radiation irradiation such as ultraviolet ray irradiation and electron beam irradiation, and crosslinking with polyisocyanate compounds, organic peroxides, organic metal salts, metal alcoholates, chelate compounds, and polyfunctional compounds. A chemical crosslinking treatment using a chemical agent is used. Among these crosslinking methods, when radiation irradiation or organic peroxides are used, decomposition reactions may occur depending on the pharmacokinetics, and highly reactive isocyanates, metal salts and organic peroxides used in normal crosslinking reactions may With metal salts, the solution may thicken after being blended, resulting in poor workability. It may also be possible to copolymerize a polyfunctional monomer such as diacrylate with an acrylic acid ester polymer in advance, but in this case as well, there is a possibility that the viscosity of the solution will increase. Therefore, in the present invention, among these crosslinking agents, trifunctional isocyanates, metal alcoholates or metal chelate compounds made of titanium or aluminum are preferred from the viewpoint of reactivity and handling properties. These crosslinking agents do not cause thickening of the solution until it is applied and dried, and are extremely easy to work with.
この場合の架橋剤の配合量はアクリル酸エステル系ポリ
マー１００重量部に対して０．０１〜２．０重量部程度
である。また、アクリル酸エステル系ポリマーか上記架
橋剤と反応する官能基をＨさない場合てし、被架橋物質
にアルカリ処理なとを施こすことによって、架橋処理か
可能な構造に変性することかできる。In this case, the amount of the crosslinking agent blended is about 0.01 to 2.0 parts by weight per 100 parts by weight of the acrylic ester polymer. In addition, if the functional group of the acrylic ester polymer that reacts with the above-mentioned crosslinking agent is not hydrogenated, the substance to be crosslinked can be treated with an alkali to modify it into a structure that can be crosslinked. .
本発明においては上記のようにして得られた架橋ゲル層
に薬物を含有させることによって、ゲル製剤とすること
ができる。含有させる薬物はその治療目的に応じて任意
に選択することかできるか、例えばコルチフステロイド
類、鎮痛消炎剤、催眠鎮静剤、精神安定剤、抗高血圧剤
、降圧利尿剤、抗生物質、麻酔剤、抗菌剤、抗真菌剤、
ビタミン剤、冠血管拡張剤（イソソルビトジニトレート
を除く）、抗ヒスタミン剤、鎮咳剤、性ホルモン（エス
トラジオールを除く）、抗蕾剤、脳循環改善荊、制吐剤
、抗腫瘍剤、生体医薬なとの種類の薬物であって、経皮
吸収可能な薬物か使用でき、これらの薬物は必要に応し
て２種類以上併用することもできる。架橋ゲル層への均
一な分散性や経皮吸収性の点から、これらの薬物のうち
疎水性薬物（溶解量０．４ｇ以以下氷水１００−常温）
を用いることか好ましい。In the present invention, a gel preparation can be obtained by incorporating a drug into the crosslinked gel layer obtained as described above. The drugs to be included can be arbitrarily selected depending on the therapeutic purpose; for example, cortiph steroids, analgesic and anti-inflammatory agents, hypnotic sedatives, tranquilizers, antihypertensive agents, antihypertensive diuretics, antibiotics, and anesthetics. , antibacterial agents, antifungal agents,
Vitamins, coronary vasodilators (excluding isosorbitol dinitrate), antihistamines, antitussives, sex hormones (excluding estradiol), antifouling agents, cerebral circulation improving agents, antiemetics, antitumor agents, biomedical drugs, etc. Any type of drug that can be absorbed through the skin can be used, and two or more of these drugs can be used in combination if necessary. From the viewpoint of uniform dispersibility in the cross-linked gel layer and transdermal absorption, hydrophobic drugs (dissolution amount 0.4 g or less or less in ice water 100 - room temperature) are recommended.
It is preferable to use
これらの薬物の含有量は薬動程や投与目的に応じて適宜
設定することかできるか、通常、架橋ゲル層中に１〜４
０重量％、好ましくは３〜３０重量？６程度含有させる
。含有量が１重量％に満だない場合は治療に有効な量の
放出か期待できず、また、４０重量％を超えると治療効
果に限界か生じると共に経済的に不利である。The content of these drugs can be set as appropriate depending on the pharmacokinetics and purpose of administration, but usually 1 to 4
0% by weight, preferably 3-30% by weight? Contain about 6. If the content is less than 1% by weight, it cannot be expected that a therapeutically effective amount will be released, and if it exceeds 40% by weight, there will be a limit to the therapeutic effect and it will be economically disadvantageous.
また、薬物を本発明のアクリル系ゲル材に含有させるに
当り、上記のように架橋ゲル層中に含有させることが好
ましいか、架橋ゲル層中に含有させずに薬物をそのまま
もしくは適当な溶剤に溶解した溶液として架橋ゲル層と
支持体との界面に介在させ、製剤周縁部をシールした形
状とすることもてきる。このように架橋ゲル層から薬物
含有層を分離することによって分解し易い薬物を用いた
場合に経日保存での薬物分解を抑制することかできる。In addition, when incorporating a drug into the acrylic gel material of the present invention, it is preferable to include it in the cross-linked gel layer as described above, or to add the drug as it is or in an appropriate solvent without incorporating it in the cross-linked gel layer. It is also possible to form a solution in which it is interposed at the interface between the crosslinked gel layer and the support, and the periphery of the preparation is sealed. By separating the drug-containing layer from the crosslinked gel layer in this manner, when a drug that is easily decomposed is used, it is possible to suppress drug decomposition during storage over time.
この場合、薬物含有層と架橋ゲル層との間に微孔性フィ
ルムを介在させることによって、薬物の放出の厳密な制
御を行なうことも可能である。In this case, it is also possible to strictly control the release of the drug by interposing a microporous film between the drug-containing layer and the crosslinked gel layer.
〈発明の効果〉
本発明のアクリル系ゲル材およびゲル製剤は以上のよう
な構成からなるものであって、架橋ゲル層かアクリル酸
エステル系ポリマーに相溶する多量の液体成分を含有し
ており、ゲル層にソフト感を付与し凝集力を維持しなが
ら皮膚刺激性を低減てきるものである。従って、本発明
の製剤を適用皮膚面から剥離除去する際に、接着力に起
因する痛みや皮膚刺激か少なく、適度な皮膚接着性と皮
膚無刺激性のバランスかとれたものとなる。また、薬物
を含有させたアクリル系ゲル製剤は、薬物を適度に皮膚
面に放出することができ、薬物を経皮吸収によって皮膚
面から生体内へ投与して各種疾患の治療や予防に効果を
発揮するものである。<Effects of the Invention> The acrylic gel material and gel preparation of the present invention have the above-described structure, and contain a large amount of liquid component that is compatible with the crosslinked gel layer or the acrylic ester polymer. This gives the gel layer a soft feel and reduces skin irritation while maintaining cohesion. Therefore, when the preparation of the present invention is peeled off from the skin surface to which it is applied, there is less pain and skin irritation caused by the adhesive force, and a balance between appropriate skin adhesion and non-irritation is achieved. In addition, acrylic gel preparations containing drugs can release drugs to the skin surface in an appropriate amount, and are effective in treating and preventing various diseases by administering drugs from the skin surface into the body through transdermal absorption. It is something that can be demonstrated.
なお、皮膚面から製剤を痛みなく剥離除去できる指標と
して、本発明品は角質の剥離量が少なく、ボランティア
を用いた角質剥離量は液体成分を含有しない対照品と比
べて１１５〜２／３の範囲であり、この範囲以外では剥
離時に痛みか生じたり、皮膚接着性不足となる場合かあ
る。In addition, as an indicator that the preparation can be painlessly peeled off from the skin surface, the product of the present invention has a small amount of exfoliation of keratin, and the amount of exfoliation of keratin using volunteers was 115 to 2/3 compared to the control product that does not contain a liquid component. Outside this range, pain may occur when peeling off, and skin adhesion may be insufficient.
〈実施例〉
以下に本発明の実施例を示し、さらに具体的に説明する
。なお、以下において、部および％は重量部および重量
％を意味する。<Examples> Examples of the present invention will be shown below and explained in more detail. In addition, in the following, parts and % mean parts by weight and weight %.
実施例１
不活性ガス雰囲気下でアクリル酸２−エチルヘキシル９
５部と、アクリル酸５部を酢酸エチル中で共重合させて
アクリル酸エステル系ポリマー溶液を調製した。Example 1 2-ethylhexyl acrylate 9 under an inert gas atmosphere
5 parts of acrylic acid and 5 parts of acrylic acid were copolymerized in ethyl acetate to prepare an acrylic ester polymer solution.
この溶液の固形分５０部にミリスチン酸イソプロピル５
０部を混合し、上記アクリル系ポリマー９９．８部に対
して０．２部のアルミニウムトリス（アセチルアセトネ
ート）を１０％アセチルアセトン溶液として添加し、酢
酸エチルをさらに加えて粘度調整を行なった。5 parts of isopropyl myristate to 50 parts of the solid content of this solution.
0.2 parts of aluminum tris (acetylacetonate) was added as a 10% acetylacetone solution to 99.8 parts of the acrylic polymer, and ethyl acetate was further added to adjust the viscosity.
得られた粘稠溶液を７５μｍ厚のポリエステル製セパレ
ータ上に乾燥後の厚み８０μｍとなるように塗布し、乾
燥して架橋ゲルを形成した。The obtained viscous solution was applied onto a polyester separator having a thickness of 75 μm to a dry thickness of 80 μm, and dried to form a crosslinked gel.
このようにして得られた架橋ゲル層に支持体としてポリ
エステル製不織布（１２ｇ／ｒｒ？）に２８部厚のポリ
エステルを押出成形したラミネートフィルムの不織布面
を貼り合わせて本発明のアクリル系ゲル材を得た。The acrylic gel material of the present invention was applied to the cross-linked gel layer thus obtained by laminating the non-woven fabric side of a laminate film made by extruding 28 parts thick polyester onto a polyester non-woven fabric (12 g/rr?) as a support. Obtained.
実施例２
実施例１において調製したアクリル酸エステル系ポリマ
ーの固形分４５部にミリスチン酸イソブ０ピル４５部、
ケトプロフェン１０部を混合した以外は、実施例■と同
様にして架橋ゲル層を形成し、これを実施例【にて用い
た支持体上に同様にして貼り合わせ、本発明のアクリル
系ゲル製剤を得た。Example 2 45 parts of isobutyl myristate was added to 45 parts of the solid content of the acrylic acid ester polymer prepared in Example 1.
A crosslinked gel layer was formed in the same manner as in Example 2, except that 10 parts of ketoprofen was mixed therein, and this was laminated in the same manner on the support used in Example 2 to form an acrylic gel formulation of the present invention. Obtained.
実施例３
実施例２においてミリスチン酸イソプロピルをパルミチ
ン酸オクチルとした以外は、全て実施例２と同様にして
本発明のアクリル系ゲル製剤を得た。Example 3 An acrylic gel preparation of the present invention was obtained in the same manner as in Example 2 except that octyl palmitate was used instead of isopropyl myristate.
比較例１
実施例１にて調製したアクリル酸エステル系ポリマーを
架橋処理せずにそのまま用いた以外は、実施例１と同様
にして液体成分を含むアクリル系ゲル材を得た。Comparative Example 1 An acrylic gel material containing a liquid component was obtained in the same manner as in Example 1, except that the acrylic acid ester polymer prepared in Example 1 was used as it was without crosslinking.
このゲル材は凝集破壊か著しく、後述の全ての試験を行
なうことかできなかった。This gel material suffered from severe cohesive failure and could not be subjected to any of the tests described below.
比較例２
実施例１にて調製したアクリル酸エステル系ポリマー溶
液の固形分９０部に対してケトプロフェン１０部を混合
し、さらに酢酸エチルを加えて粘度調整を行なった以外
は、実施例１と同様にして液体成分を含まず架橋処理も
していないアクリル系製剤を得た。Comparative Example 2 Same as Example 1 except that 10 parts of ketoprofen was mixed with 90 parts of the solid content of the acrylic acid ester polymer solution prepared in Example 1, and ethyl acetate was further added to adjust the viscosity. An acrylic preparation containing no liquid component and no crosslinking treatment was obtained.
比較例３
比較例２において架橋剤をポリマー固形分に対して０．
２部添加した以外は全て比較例２と同様にして液体成分
を含まない架橋型のアクリル系製剤を得た。Comparative Example 3 In Comparative Example 2, the amount of crosslinking agent was 0.0% based on the solid content of the polymer.
A crosslinked acrylic preparation containing no liquid component was obtained in the same manner as in Comparative Example 2 except that 2 parts of the preparation was added.
実施例４
不活性ガス雰囲気下でアクリル酸２−エチルヘキシル７
５部と、Ｎ−ビニル−２−ピロリドン２３部、アクリル
酸２部を酢酸エチル中で共重合させてアクリル酸エステ
ル系ポリマー溶液を調製した。Example 4 2-ethylhexyl acrylate 7 under inert gas atmosphere
5 parts of N-vinyl-2-pyrrolidone and 2 parts of acrylic acid were copolymerized in ethyl acetate to prepare an acrylic ester polymer solution.
この溶液の固形分５０部にパルミチン酸オクチル５０部
を混合し、上記アクリル系ポリマー９９゜８部に対して
０．２部のエチルアセトアセテートアルミニウムジイソ
プロピレートを１０％アセチルアセトン溶液として添加
し、酢酸エチルをさらに加えて粘度調整を行なった。50 parts of octyl palmitate was mixed with 50 parts of the solid content of this solution, and 0.2 parts of ethyl acetoacetate aluminum diisopropylate was added as a 10% acetylacetone solution to 99.8 parts of the above acrylic polymer. Ethyl was further added to adjust the viscosity.
得られた粘稠溶液を用いた以外は実施例１と同様にして
本発明のアクリル系ゲル材を得た。An acrylic gel material of the present invention was obtained in the same manner as in Example 1 except that the obtained viscous solution was used.
実施例５
実施例４において調製したアクリル酸エステル系ポリマ
ーの固形分４５部にパルミチン酸オクチル４０部、ニフ
ェジピン１５部を混合した以外は、実施例４と同様にし
て架橋ゲル層を形成した。Example 5 A crosslinked gel layer was formed in the same manner as in Example 4, except that 40 parts of octyl palmitate and 15 parts of nifedipine were mixed with 45 parts of the solid content of the acrylic acid ester polymer prepared in Example 4.
実施例１にて用いた支持体のポリエステルフィルムにア
ルミニウム蒸着を施して遮光処理を行った以外は、実施
例１と同様にして本発明のアクリル系ゲル製剤を得た。An acrylic gel formulation of the present invention was obtained in the same manner as in Example 1, except that the polyester film as the support used in Example 1 was subjected to aluminum vapor deposition for light shielding treatment.
実施例６
実施例５においてパルミチン酸オクチルをミリスチン酸
イソトリデシルとした以外は、全て実施例５と同様にし
て本発明のアクリル系ゲル製剤を得た。Example 6 An acrylic gel preparation of the present invention was obtained in the same manner as in Example 5 except that isotridecyl myristate was used instead of octyl palmitate.
比較例４
実施例４にて調製したアクリル酸エステル系ポリマーを
架橋処理せずにそのまま用いた以外は、実施例４と同様
にして液体成分を含まず架橋処理もしていないアクリル
系貼付材を得た。Comparative Example 4 An acrylic patch containing no liquid component and without crosslinking treatment was obtained in the same manner as in Example 4, except that the acrylic acid ester polymer prepared in Example 4 was used as it was without crosslinking treatment. Ta.
この貼付材は凝集破壊が著しく、後述の全ての試験を行
なうことかできなかった。This adhesive material suffered from significant cohesive failure and could not be subjected to all of the tests described below.
比較例５
実施例４にて調製したアクリル酸エステル系ポリマー溶
液の固形分８５部に対してニフェジピン１５部を混合し
、さらに酢酸エチルを加えて粘度調節を行なった以外は
、実施例４と同様にして液体成分を含まず架橋処理もし
ていないアクリル系製剤を得た。Comparative Example 5 Same as Example 4, except that 15 parts of nifedipine was mixed with 85 parts of the solid content of the acrylic acid ester polymer solution prepared in Example 4, and ethyl acetate was further added to adjust the viscosity. An acrylic preparation containing no liquid component and no crosslinking treatment was obtained.
比較例６
比較例５において架橋剤をポリマー固形分に対して０，
２部添加した以外は比較例５と同様にして液体成分を含
まない架橋型のアクリル系製剤を得た。Comparative Example 6 In Comparative Example 5, the amount of crosslinking agent was 0,
A cross-linked acrylic preparation containing no liquid component was obtained in the same manner as in Comparative Example 5, except that 2 parts were added.
比較例７
比較例４にて用いたアクリル酸エステル系ポリマーに代
えてポリイソブチレン（粘度平均分子量９９万）１０部
、ポリイソブチレン（粘度平均分子量６万）１５部、ポ
リイソブチレン（粘度平均分子量１２６０）３部、脂環
式石油系樹脂（軟化点１００°Ｃ） ７部からなるポリ
イソブチレンゴム系ポリマーを用い、酢酸エチルに代え
てトルエンを用いた以外は、比較例４と同様にしてゴム
系ゲル製剤を得た。Comparative Example 7 In place of the acrylic ester polymer used in Comparative Example 4, 10 parts of polyisobutylene (viscosity average molecular weight: 990,000), 15 parts of polyisobutylene (viscosity average molecular weight: 60,000), polyisobutylene (viscosity average molecular weight: 1260) A rubber gel was prepared in the same manner as in Comparative Example 4, except that a polyisobutylene rubber polymer consisting of 3 parts and 7 parts of an alicyclic petroleum resin (softening point 100°C) was used, and toluene was used instead of ethyl acetate. A formulation was obtained.
なお、本ゲル製剤は製剤の作製直後から、多量のニフェ
ジピンの結晶の析出か見られた。In addition, in this gel preparation, a large amount of nifedipine crystals were observed to precipitate immediately after preparation.
実施例７
不活性ガス雰囲気下でアクリル酸２−エチルヘキソルア
０部と、酢酸ビニル２５部、２−ヒドロキシエチルメタ
クリレート５部を酢酸エチル中で共重合させてアクリル
酸エステル系ポリマー溶液を調製した。Example 7 An acrylic acid ester polymer solution was prepared by copolymerizing 0 parts of 2-ethylhexol acrylate, 25 parts of vinyl acetate, and 5 parts of 2-hydroxyethyl methacrylate in ethyl acetate under an inert gas atmosphere.
この溶液の固形分５０部にミリスチン酸イソトノデシル
５０部を混合し、上記アクリル酸エステル系ポリマー９
９．７部に対して０．３部の三官能性イソシアネート（
コロネー１−ＨＬ、 日本ポリウレタン社製）を１０
％酢酸エチル溶液として添加し、酢酸エチルをさらに加
えて粘度調整を行なった。50 parts of isotonodecyl myristate was mixed with 50 parts of the solid content of this solution, and the above acrylic acid ester polymer 9
9.7 parts to 0.3 parts of trifunctional isocyanate (
Coronet 1-HL, manufactured by Nippon Polyurethane Co., Ltd.) 10
% ethyl acetate solution, and ethyl acetate was further added to adjust the viscosity.
得られた粘稠溶液を用いた以外は実施例１と同様にして
本発明のアクリル系ゲル材を得た。An acrylic gel material of the present invention was obtained in the same manner as in Example 1 except that the obtained viscous solution was used.
実施例８
実施例７において調製したアクリル酸エステル系ポリマ
ーの固形分４５部にミリスチン酸トリデシル４５部、ク
ロニジ２１０部を混合し、アクリル酸エステル系ポリマ
ー９９．７部に対して０．３部の三官能性イソシアネー
ト（コロネートＨＬ、 日本ポリウレタン社製）を１
０％酢酸エチル溶液として添加した以外は、実施例７と
同様にして架橋ゲル層を形成し、これを実施例１にて用
いた支持体上に同様にして貼り合わせ、本発明のアクリ
ル系ゲル製剤を得た。Example 8 45 parts of tridecyl myristate and 210 parts of Clonidi were mixed with 45 parts of the solid content of the acrylic ester polymer prepared in Example 7, and 0.3 part of tridecyl myristate was added to 99.7 parts of the acrylic ester polymer. 1 trifunctional isocyanate (Coronate HL, manufactured by Nippon Polyurethane Co., Ltd.)
A crosslinked gel layer was formed in the same manner as in Example 7, except that it was added as a 0% ethyl acetate solution, and this was laminated on the support used in Example 1 in the same manner as the acrylic gel of the present invention. A formulation was obtained.
実施例９
実施例８においてミリスチン酸イソトリデシルをミリス
チン酸イソプロピルとした以外は、全て実施例８と同様
にして本発明のアクリル系ゲル製剤を得た。Example 9 An acrylic gel preparation of the present invention was obtained in the same manner as in Example 8 except that isopropyl myristate was used instead of isotridecyl myristate.
比較例８
実施例７において架橋剤を配合しなかった以外は、全て
実施例７と同様にして液体成分を含有するが架橋処理を
していないアクリル系ゲル材を得た。Comparative Example 8 An acrylic gel material containing a liquid component but not crosslinked was obtained in the same manner as in Example 7 except that no crosslinking agent was added.
このゲル材は凝集破壊か著しく、後述の全ての試験を行
なうことができなかった。This gel material suffered from severe cohesive failure and could not be subjected to any of the tests described below.
比較例９
実施例７にて調製したアクリル酸エステル系ポリマー溶
液の固形分９９．７部に対して０．３部の三官能性イソ
シアネート（コロネートＨＬ、 日本ポリウレタン社
製）を１０％酢酸エチル溶液として添加し、酢酸エチル
をさらに加えて粘度調整を行なった以外は、実施例７と
同様にして液状成分を含まない架橋型のアクリル系貼付
材を得た。Comparative Example 9 0.3 part of trifunctional isocyanate (Coronate HL, manufactured by Nippon Polyurethane Co., Ltd.) was added to a 10% ethyl acetate solution based on the solid content of 99.7 parts of the acrylic acid ester polymer solution prepared in Example 7. A crosslinked acrylic patch containing no liquid component was obtained in the same manner as in Example 7, except that ethyl acetate was further added to adjust the viscosity.
比較例１０
実施例７にて調製したアクリル酸エステル系ポリマー溶
液の固形分９０部にクロニジ２１０部を混合し、さらに
上記アクリル系ポリマーの固形分９９．７部に対して０
．３部の三官能性イソシアネート（コロネートＨＬ、
日本ポリウレタン社製）を１０％酢酸エチル溶液とし
て添加し、酢酸エチルをさらに加えて粘度調整を行なっ
た以外は、実施例７と同様にして液状成分を含まない架
橋型のアクリル系製剤を得た。Comparative Example 10 210 parts of Kuroniji was mixed with 90 parts of the solid content of the acrylic acid ester polymer solution prepared in Example 7, and 0
．． 3 parts trifunctional isocyanate (Coronate HL,
A cross-linked acrylic formulation containing no liquid component was obtained in the same manner as in Example 7, except that 10% ethyl acetate solution (manufactured by Nippon Polyurethane Co., Ltd.) was added and ethyl acetate was further added to adjust the viscosity. .
比較例１１
実施例１にて得たアクリル酸エステル系ポリマー溶液を
用いて、液体成分、架橋剤および薬物の何れも含有しな
い貼付剤を作製した。なお、支持体などは実施例１と同
様の条件で用いた。Comparative Example 11 Using the acrylic ester polymer solution obtained in Example 1, a patch containing no liquid component, crosslinking agent, or drug was produced. Note that the support and the like were used under the same conditions as in Example 1.
比較例１２
実施例１においてアクリル酸エステル系ポリマー溶液の
固形分８２部に対してミリスチン酸イソプロピルを１８
部配合した以外は、全て実施例１と同様にしてアクリル
系ゲル材を得た。Comparative Example 12 In Example 1, 18 parts of isopropyl myristate was added to 82 parts of the solid content of the acrylic acid ester polymer solution.
An acrylic gel material was obtained in the same manner as in Example 1, except that the gel material was blended in the same manner as in Example 1.
実験例
上記各実施例および比較例にて得た各ゲル材およびゲル
製剤のサンプルを、４０℃、７５％の加湿条件下で２週
間保存したのち、下記の試験を行なった。なお、不織布
に染色液が吸収されて正確な測定が困難であるので、角
質剥離量の測定に用いるサンプルについては、支持体と
して不織布を積層しない単層フィルム（９μｍ厚）を使
用した。Experimental Examples Samples of gel materials and gel preparations obtained in the above Examples and Comparative Examples were stored for two weeks at 40° C. and 75% humidity, and then the following tests were conducted. In addition, since the dyeing liquid is absorbed by the nonwoven fabric, making accurate measurement difficult, a single-layer film (9 μm thick) without laminated nonwoven fabric was used as a support for the sample used for measuring the amount of keratin exfoliation.
また、クロニジンを含有する製剤についてはボランティ
アを用いたヒト貼付試験を行わなかった。Furthermore, no human patch tests using volunteers were conducted for preparations containing clonidine.
結果を第１表および第２表に示す。The results are shown in Tables 1 and 2.
各実施例および比較例にて得たサンプルを、予め除毛し
たウサギの背部に貼付し、１．０、ｚＯ１４，０，６，
０，８，０の各時間経過毎に各々２ｙｄ採血し、これを
ガスクロマトグラフィーにて血中の薬物濃度を測定した
。なお、サンプルの大きさはクロニジン含有製剤のみ３
ａｌ（１，７３ａｎ角）とし、その他は５０ｃａｆ（７
，１ｃｍ角）とした。The samples obtained in each Example and Comparative Example were pasted on the back of a rabbit whose hair had been removed in advance.
2 yd of blood was collected at each time interval of 0, 8, and 0, and the drug concentration in the blood was measured using gas chromatography. Note that the sample size is 3 for clonidine-containing preparations only.
al (1,73an square), and the rest is 50caf (7
, 1 cm square).
ベークライト板に輻１２ｍに切断した帯状の各サンプル
を貼付し、荷重３００ｇのローラーを１往復させて密着
させた後、１８０度方向に３００ａｍ ／ ｍ ｉ ｎ
の速度で剥離し、その際の剥離力を測定した。Each strip-shaped sample cut to a radius of 12 m was pasted on a Bakelite plate, and a roller with a load of 300 g was moved back and forth once to bring it into close contact.
The peeling force was measured at a speed of .
レオメータ−を用いたプローブタックによって評価した
。Evaluation was made by probe tack using a rheometer.
サンプルを製剤の皮膚貼付面を上にして金属板に固定し
、これに直径１０ｍｍの球型プローブを１００ｇの荷重
で２ｃｍ／分の速度にて接触させたのち、２０秒間その
状態を維持し、次いて同速度でこの球型プローブを引き
離した時の剥離力を測定した。The sample was fixed on a metal plate with the skin application side of the preparation facing up, and a spherical probe with a diameter of 10 mm was brought into contact with this at a speed of 2 cm/min with a load of 100 g, and the state was maintained for 20 seconds. Next, the peeling force when this spherical probe was pulled apart at the same speed was measured.
ボランティア５名の上腕部内側にサンプルを貼付し、３
０分後に剥離してその際の痛みを測定した。評価は５段
階で、最も痛みの少ないものを１点としてその平均点を
求めた。なお、基準として比較例１のものを５点として
判定した。The sample was pasted on the inside of the upper arm of 5 volunteers, and 3
It was peeled off after 0 minutes and the pain at that time was measured. The evaluation was on a five-point scale, with one point being the least painful one, and the average score was calculated. Note that, as a reference, Comparative Example 1 was evaluated with 5 points.
ボランティア３名（Ａ、 Ｂ、 Ｃ）の上腕部内側
に、直径１６−に切断した円形サンプルを３０分間貼付
、剥離後、このサンプルを染色液（Ｇｅｎｔｉａｎｖｉ
ｏｌｅｔ １．０％、 Ｂｒ１ｌｌｉａｎ ｇｒｅｅｎ
Ｏ，５％、蒸留水９８．５％）に３分間浸漬し、そ
の後水洗して、角質細胞の染色を行なった。A circular sample cut into a diameter of 16 mm was pasted on the inner side of the upper arm of three volunteers (A, B, and C) for 30 minutes, and after peeling off, the sample was soaked in a staining solution (Gentianvi
olet 1.0%, Br1llian green
The cells were immersed for 3 minutes in 5% O, 98.5% distilled water, and then washed with water to stain the corneocytes.
５％ドデシル硫酸ナトリウム水溶液中に、これらのサン
プルを一昼夜浸漬して染色液の抽出を行ない、この抽出
液の吸光度（５９５ｎｍ）を測定することにより、剥離
した角質細胞数の比較を行なった。即ち、測定した吸光
度か高いほと剥離した角質量か多いと判断した。These samples were immersed in a 5% sodium dodecyl sulfate aqueous solution overnight to extract a staining solution, and the absorbance (595 nm) of this extract was measured to compare the number of exfoliated corneocytes. That is, it was determined that the higher the measured absorbance, the greater the exfoliated corneal mass.
なお、実体顕微鏡にて計数した剥離角質細胞数と上記吸
光度との間には、良好な相関関係か確認された。It was confirmed that there was a good correlation between the number of exfoliated corneocytes counted using a stereomicroscope and the above absorbance.
第１表
第２表
第１表および第２表から明らかなように、本発明アクリ
ル系ゲル材およびゲル製剤は比較例品と比べて、剥離時
の痛みか少なく、また角質の剥離量も少ないものである
。さらに、薬物を含有させたゲル製剤においては薬物か
速やかにがっ多量に経皮吸収されることか判明した。As is clear from Tables 1 and 2, the acrylic gel materials and gel preparations of the present invention cause less pain during peeling and less peeling of dead skin than the comparative products. It is something. Furthermore, it has been found that in gel preparations containing drugs, the drugs are rapidly and in large amounts absorbed through the skin.
Claims (4)
と相溶する液体成分とを含む架橋ゲル層が支持体の少な
くとも片面に形成されてなるアクリル系ゲル材。(1) An acrylic gel material in which a crosslinked gel layer containing an acrylic acid ester polymer and a liquid component compatible with the polymer is formed on at least one side of a support.
有重量比が、１．０：０．２５〜１．０：２．０である
請求項（１）記載のアクリル系ゲル材。(2) The acrylic gel material according to claim 1, wherein the weight ratio of the acrylic acid ester polymer to the liquid component is from 1.0:0.25 to 1.0:2.0.
ルコラートおよび金属キレート、ならびに三官能イソシ
アネートから選ばれた一種の架橋剤によってなされてい
る請求項（１）記載のアクリル系ゲル材。(3) The acrylic gel material according to claim 1, wherein the crosslinking is carried out by a crosslinking agent selected from metal alcoholates and metal chelates made of titanium or aluminum, and trifunctional isocyanates.
系ゲル材中に、薬物が含有されてなるアクリル系ゲル製
剤。(4) An acrylic gel preparation comprising a drug contained in the acrylic gel material according to any one of claims (1) to (3).
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE69010317T DE69010317T3 (en) | 1989-12-28 | 1990-12-21 | Acrylic gel and its manufacture. |
| EP90125107A EP0435199B2 (en) | 1989-12-28 | 1990-12-21 | Acrylic gel material and acrylic gel preparation |
| ES90125107T ES2055291T5 (en) | 1989-12-28 | 1990-12-21 | ACRYLIC GEL MATERIAL AND ACRYLIC GEL PREPARATION. |
| CA002033109A CA2033109C (en) | 1989-12-28 | 1990-12-24 | Acrylic gel material and acrylic gel preparation |
| US07/899,278 US5298258A (en) | 1989-12-28 | 1992-06-16 | Acrylic oily gel bioadhesive material and acrylic oily gel preparation |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1-344639 | 1989-12-28 | ||
| JP34463989 | 1989-12-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03220120A true JPH03220120A (en) | 1991-09-27 |
| JP2700835B2 JP2700835B2 (en) | 1998-01-21 |
Family
ID=18370821
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2237384A Expired - Fee Related JP2970772B2 (en) | 1989-12-28 | 1990-09-06 | Transdermal gel preparation |
| JP2237382A Expired - Lifetime JP2700835B2 (en) | 1989-12-28 | 1990-09-06 | Acrylic gel material and acrylic gel preparation |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2237384A Expired - Fee Related JP2970772B2 (en) | 1989-12-28 | 1990-09-06 | Transdermal gel preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (2) | JP2970772B2 (en) |
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| JP2006288887A (en) | 2005-04-13 | 2006-10-26 | Nitto Denko Corp | Adhesive skin patch |
| JP2011182847A (en) | 2010-03-05 | 2011-09-22 | Three M Innovative Properties Co | Medical adhesive composition |
| JP2020132637A (en) * | 2019-02-14 | 2020-08-31 | 久光製薬株式会社 | Plaster |
| JP7282701B2 (en) * | 2020-01-23 | 2023-05-29 | 久光製薬株式会社 | poultice |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS577409A (en) * | 1980-06-14 | 1982-01-14 | Nitto Electric Ind Co Ltd | Plaster |
| JPH03112556A (en) * | 1989-09-27 | 1991-05-14 | Sekisui Chem Co Ltd | Application agent |
-
1990
- 1990-09-06 JP JP2237384A patent/JP2970772B2/en not_active Expired - Fee Related
- 1990-09-06 JP JP2237382A patent/JP2700835B2/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS577409A (en) * | 1980-06-14 | 1982-01-14 | Nitto Electric Ind Co Ltd | Plaster |
| JPH03112556A (en) * | 1989-09-27 | 1991-05-14 | Sekisui Chem Co Ltd | Application agent |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06506944A (en) * | 1991-06-10 | 1994-08-04 | シュバルツ ファルマ アクチェンゲゼルシャフト | Nitroglycerin ointment and its manufacturing method |
| JPH07309755A (en) * | 1994-05-20 | 1995-11-28 | Nichiban Co Ltd | Cataplasm of antifungal agent |
| EP0819438A2 (en) | 1996-07-19 | 1998-01-21 | Nitto Denko Corporation | Buprenorphine percutaneous absorption preparation |
| US6797280B1 (en) | 1998-07-29 | 2004-09-28 | Teijin Limited | Pressure-sensitive adhesive composition and moisture-permeable pressure-sensitive adhesive tape, pressure-sensitive adhesive drug composition, and pressure-sensitive adhesive tape preparation each containing the composition |
| JP2001270839A (en) * | 2000-02-10 | 2001-10-02 | Rohm & Haas Co | Bioadhesive composition |
| JP2003048832A (en) * | 2001-08-02 | 2003-02-21 | Kosumedei:Kk | Patch for skin conditioning |
| JP2003062058A (en) * | 2001-08-29 | 2003-03-04 | Nitto Denko Corp | Medical adhesive composition, medical adhesive tape and percutaneous absorbing tape preparation using it |
| JP2004075538A (en) * | 2002-08-09 | 2004-03-11 | Teikoku Seiyaku Co Ltd | Norehilsterone-containing external plaster |
| US7759400B2 (en) | 2004-01-07 | 2010-07-20 | Hisamitsu Pharmaceutical Co., Inc. | Pressure-sensitive adhesive composition and skin patch |
| US8389001B2 (en) | 2004-04-13 | 2013-03-05 | Nipro Patch Co., Ltd. | Precursor composition for crosslinkable pressure-sensitive adhesive for skin |
| US8591939B2 (en) | 2004-08-12 | 2013-11-26 | Nitto Denko Corporation | Adhesive preparation containing fentanyl |
| US8394404B2 (en) | 2004-08-12 | 2013-03-12 | Nitto Denko Corporation | Adhesive material and adhesive preparation |
| JP2006225522A (en) * | 2005-02-17 | 2006-08-31 | Nitto Denko Corp | Pressure-sensitive adhesive, pressure-sensitive adhesive tape using the same and percutaneous absorption type formulation |
| WO2007024015A1 (en) * | 2005-08-25 | 2007-03-01 | The University Of Tokyo | Material for preventing tissue adhesion and arthrogryposis |
| WO2007097365A1 (en) | 2006-02-23 | 2007-08-30 | Lintec Corporation | Pressure-sensitive adhesive composition and pressure-sensitive adhesive sheet making use of the same |
| US8809454B2 (en) | 2006-02-23 | 2014-08-19 | Lintec Corporation | Pressure-sensitive adhesive composition and pressure-sensitive adhesive sheet using the same |
| JP5130203B2 (en) * | 2006-04-28 | 2013-01-30 | ライオン株式会社 | Non-aqueous adhesive composition, patch and method for producing the patch |
| WO2007126067A1 (en) * | 2006-04-28 | 2007-11-08 | Lion Corporation | Nonaqueous pressure-sensitive adhesive composition, patches and process for production of patches |
| EP2002824A2 (en) | 2007-06-15 | 2008-12-17 | Nitto Denko Corporation | Gel composition and use thereof |
| JP2009286707A (en) * | 2008-05-27 | 2009-12-10 | Nitto Denko Corp | Gel composition for medical material or sanitary material, its formed product and adhesive material or adhesive preparation using the same |
| EP2163267A2 (en) | 2008-09-12 | 2010-03-17 | Nitto Denko Corporation | Patch and patch preparation |
| CN113423394A (en) * | 2019-02-14 | 2021-09-21 | 久光制药株式会社 | Cataplasm |
| US11903915B2 (en) | 2019-02-14 | 2024-02-20 | Hisamitsu Pharmaceutical Co., Inc. | Poultice |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2970772B2 (en) | 1999-11-02 |
| JP2700835B2 (en) | 1998-01-21 |
| JPH03223212A (en) | 1991-10-02 |
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