JP5832289B2 - 水溶性ポリマー組成物、皮膚貼付剤の膏体層形成用組成物、及び皮膚貼付剤 - Google Patents
水溶性ポリマー組成物、皮膚貼付剤の膏体層形成用組成物、及び皮膚貼付剤 Download PDFInfo
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- JP5832289B2 JP5832289B2 JP2011524739A JP2011524739A JP5832289B2 JP 5832289 B2 JP5832289 B2 JP 5832289B2 JP 2011524739 A JP2011524739 A JP 2011524739A JP 2011524739 A JP2011524739 A JP 2011524739A JP 5832289 B2 JP5832289 B2 JP 5832289B2
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- water
- meth
- composition
- acrylic acid
- soluble
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- 238000001879 gelation Methods 0.000 claims description 37
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
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- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
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- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 2
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- 150000001875 compounds Chemical class 0.000 description 2
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- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 2
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- HGXJDMCMYLEZMJ-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOOC(=O)C(C)(C)C HGXJDMCMYLEZMJ-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- MYECVPCGFLCGQX-UHFFFAOYSA-N 2-[(1-amino-2-methyl-1-phenyliminopropan-2-yl)diazenyl]-2-methyl-n'-phenylpropanimidamide;dihydrochloride Chemical compound Cl.Cl.C=1C=CC=CC=1NC(=N)C(C)(C)N=NC(C)(C)C(=N)NC1=CC=CC=C1 MYECVPCGFLCGQX-UHFFFAOYSA-N 0.000 description 1
- AEZBIUBWOJAYOA-UHFFFAOYSA-N 2-[2-[2-[2-[1-(2-hydroxyethyl)-4,5-dihydroimidazol-2-yl]propan-2-yldiazenyl]propan-2-yl]-4,5-dihydroimidazol-1-yl]ethanol Chemical compound N=1CCN(CCO)C=1C(C)(C)N=NC(C)(C)C1=NCCN1CCO AEZBIUBWOJAYOA-UHFFFAOYSA-N 0.000 description 1
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- XYFRHHAYSXIKGH-UHFFFAOYSA-N 3-(5-methoxy-2-methoxycarbonyl-1h-indol-3-yl)prop-2-enoic acid Chemical compound C1=C(OC)C=C2C(C=CC(O)=O)=C(C(=O)OC)NC2=C1 XYFRHHAYSXIKGH-UHFFFAOYSA-N 0.000 description 1
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 1
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- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
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- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 1
- CIWBSHSKHKDKBQ-MVHIGOERSA-N D-ascorbic acid Chemical compound OC[C@@H](O)[C@@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-MVHIGOERSA-N 0.000 description 1
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 1
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- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
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- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 229940024545 aluminum hydroxide Drugs 0.000 description 1
- UTUUIUQHGDRVPU-UHFFFAOYSA-K aluminum;2-aminoacetate;dihydroxide;hydrate Chemical compound O.[OH-].[OH-].[Al+3].NCC([O-])=O UTUUIUQHGDRVPU-UHFFFAOYSA-K 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- WPKYZIPODULRBM-UHFFFAOYSA-N azane;prop-2-enoic acid Chemical compound N.OC(=O)C=C WPKYZIPODULRBM-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 235000019326 ethyl hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- FPNCFEPWJLGURZ-UHFFFAOYSA-L iron(2+);sulfite Chemical compound [Fe+2].[O-]S([O-])=O FPNCFEPWJLGURZ-UHFFFAOYSA-L 0.000 description 1
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 1
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- WVFLGSMUPMVNTQ-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-[[1-(2-hydroxyethylamino)-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCO WVFLGSMUPMVNTQ-UHFFFAOYSA-N 0.000 description 1
- BUGISVZCMXHOHO-UHFFFAOYSA-N n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-2-[[1-[[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCC(CO)(CO)NC(=O)C(C)(C)N=NC(C)(C)C(=O)NC(CO)(CO)CO BUGISVZCMXHOHO-UHFFFAOYSA-N 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- 229920006284 nylon film Polymers 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229910001380 potassium hypophosphite Inorganic materials 0.000 description 1
- CRGPNLUFHHUKCM-UHFFFAOYSA-M potassium phosphinate Chemical compound [K+].[O-]P=O CRGPNLUFHHUKCM-UHFFFAOYSA-M 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007717 redox polymerization reaction Methods 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- KOUDKOMXLMXFKX-UHFFFAOYSA-N sodium oxido(oxo)phosphanium hydrate Chemical compound O.[Na+].[O-][PH+]=O KOUDKOMXLMXFKX-UHFFFAOYSA-N 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 description 1
- 229940042585 tocopherol acetate Drugs 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
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
- A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
- A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
- A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
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- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
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- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
- A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
- A61K9/7084—Transdermal patches having a drug layer or reservoir, and one or more separate drug-free skin-adhesive layers, e.g. between drug reservoir and skin, or surrounding the drug reservoir; Liquid-filled reservoir patches
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M35/00—Devices for applying media, e.g. remedies, on the human body
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Description
項1. 水溶性ポリ(メタ)アクリル酸ポリマー及びゲル化速度遅延剤を含有する水溶性ポリマー組成物。
項2. (メタ)アクリル酸及びその塩からなる群から選ばれた少なくとも1種の(メタ)アクリル酸化合物を重合することによって水溶性ポリ(メタ)アクリル酸ポリマーの含水ゲルを得た後、得られた含水ゲルの乾燥前又は乾燥中にゲル化速度遅延剤を添加して、乾燥することにより得られる上記項1に記載の水溶性ポリマー組成物。
項3. ゲル化速度遅延剤の添加量が、水溶性ポリ(メタ)アクリル酸ポリマーを得るために使用した(メタ)アクリル酸及びその塩からなる群から選ばれた少なくとも1種の(メタ)アクリル酸化合物100質量部に対して0.1〜10質量部である上記項1又は2に記載の水溶性ポリマー組成物。
項4. 上記項1〜3のいずれかに記載の水溶性ポリマー組成物及び多価金属化合物を含有する皮膚貼付剤の膏体層形成用組成物。
項5. 多価金属化合物の量が、水溶性ポリマー組成物100質量部に対して、0.01〜20質量部である上記項4に記載の膏体層形成用組成物。
項6. 上記項4又は5に記載の膏体層形成用組成物から形成された膏体層を有する皮膚貼付剤。
項7. パップ剤又は冷却シートである上記項6に記載の皮膚貼付剤。
項8. (メタ)アクリル酸及びその塩からなる群から選ばれた少なくとも1種の(メタ)アクリル酸化合物を重合して含水ゲルを得た後、該含水ゲルの乾燥前又は乾燥中にゲル化速度遅延剤を添加して乾燥することを特徴とする水溶液ポリマー組成物の製造方法。
項9. 上記項8の方法によって得られる水溶性ポリマー組成物に、多価金属化合物を添加する工程を含む皮膚貼付剤の膏体層形成用組成物の製造方法。
以下、本発明の水溶性ポリマー組成物、及び該組成物を用いる皮膚貼付剤の膏体層形成用組成物について具体的に説明する。
本発明の水溶性ポリマー組成物は、水溶性ポリ(メタ)アクリル酸ポリマーとゲル化速度遅延剤を有効成分として含有するものである。以下、該組成物に含まれる水溶性ポリ(メタ)アクリル酸ポリマーとゲル化速度遅延剤について説明する。
本発明で用いる水溶性ポリ(メタ)アクリル酸ポリマーは、(メタ)アクリル酸及びその塩からなる群から選ばれた少なくとも1種の(メタ)アクリル酸化合物をモノマー成分として用い、これを重合して得られるものであれば特に限定はない。重合方法としては、特に限定されず、(メタ)アクリル酸化合物の代表的な重合方法である逆相懸濁重合法、水溶液重合法等が挙げられる。特に、モノマー成分を重合する際に、極度な低分子量体や極度な高分子量体が生成しないように重合度をコントロールしたものが好ましい。尚、本願明細書では、「(メタ)アクリル酸」とは、「アクリル酸」と「メタクリル酸」の双方を意味するものである。
逆相懸濁重合法では、例えば、(メタ)アクリル酸及びその塩からなる群から選ばれた少なくとも1種の(メタ)アクリル酸化合物をモノマー成分として、ラジカル重合開始剤を用いて、界面活性剤及び高分子分散剤からなる群から選ばれた少なくとも一種の成分を含む石油系炭化水素溶媒中において、油中水滴型逆相懸濁重合を行えばよい。なお、逆相懸濁重合法においては、逆相懸濁重合によって得られた水溶性ポリ(メタ)アクリル酸ポリマーのスラリーに、(メタ)アクリル酸化合物をさらに添加し、2段以上の多段で重合を行うこともできる。
次に、実施形態の他の一例として、水溶液重合法について説明する。水溶液重合法においては、例えば、(メタ)アクリル酸化合物をモノマー成分として用い、ラジカル重合開始剤を用いて、常法に従って水溶液重合を行えばよい。
本発明では、ゲル化速度遅延剤としては、金属イオンに対してキレート化能又は配位能を持つ化合物を用いることができる。このようなゲル化速度遅延剤としては、特に限定的ではなく、ポリ(メタ)アクリル酸ポリマーのゲル化速度遅延剤として公知の化合物を用いることができ、具体例として、エチレンジアミン四酢酸、ジエチレントリアミン五酢酸、酢酸、クエン酸、フマル酸、酒石酸、乳酸、リンゴ酸等の有機酸;これらの有機酸の塩;ホウ酸、炭酸等の無機酸;ホウ酸塩、炭酸塩、炭酸水素塩などの無機酸塩等を挙げることができる。有機酸塩及び無機酸塩の種類については、水溶性塩であればよく、特に限定はないが、例えば、アルカリ金属塩、アルカリ土類金属塩、アンモニウム塩等を例示できる。
本発明の水溶性ポリマー組成物は、上記した水溶性ポリ(メタ)アクリル酸ポリマーとゲル化速度遅延剤を有効成分として含有するものである。この様に予め水溶性ポリ(メタ)アクリル酸ポリマーとゲル化速度遅延剤を含有する組成物とすることによって、水溶性ポリマーとゲル化速度遅延剤とが均一性よく存在することになり、架橋剤として用いる多価金属化合物と反応させた際に、硬化速度をコントロールしやすくなる。このため、多価金属化合物を添加してゲル化を進行させて皮膚貼付剤の膏体層を形成する際に、ゲル状態の組成物の硬化反応の開始までに適度の誘導期を発現させることができ、その結果、添加剤成分を均一に混合でき、支持体に対する塗工作業も容易となる。
上記した水溶性ポリ(メタ)アクリル酸ポリマーとゲル化速度遅延剤を含有する水溶性ポリマー組成物に、更に、架橋剤として多価金属化合物を添加した組成物は、徐々にゲル化が進行する性質を有するものである。このような組成物は、皮膚貼付剤の膏体層形成用組成物として使用することができ、例えば、多価金属化合物を添加してゲル状としたものを皮膚貼付剤用の支持体に塗工して硬化熟成することによって、皮膚貼付剤の膏体層を形成することができる。
上記した水溶性ポリ(メタ)アクリル酸ポリマーとゲル化速度遅延剤を含有する水溶性ポリマー組成物に架橋剤として多価金属化合物を添加し、更に、必要に応じて任意の添加成分を加えた組成物からゲル状の膏体を形成し、これを不織布などの支持体に塗工し、硬化熟成して膏体層を形成することによって、皮膚貼付剤を得ることができる。皮膚貼付剤の具体例としては、パップ剤、冷却シート等を挙げることができる。
[水溶性ポリマー組成物の調製]
還流冷却器、滴下ロート、窒素ガス導入管並びに撹拌機及び撹拌羽根を備えた1000ml容の5つ口円筒型丸底フラスコを準備した。このフラスコに、n−ヘプタン340gを入れ、HLB3のショ糖ステアリン酸エステル(三菱化学フーズ株式会社製、リョートーシュガーエステルS−370)0.92g及び無水マレイン酸変性エチレン・プロピレン共重合体(三井化学株式会社製、ハイワックス1105A)0.92gを添加し、撹拌しながら80℃まで昇温して界面活性剤を溶解した後、55℃まで冷却した。
蒸留水86.55質量部に、酒石酸0.25質量部を添加し、溶解させ、これをA液とした。
還流冷却器、滴下ロート、窒素ガス導入管並びに撹拌機及び撹拌羽根を備えた1000ml容の5つ口円筒型丸底フラスコを準備した。このフラスコに、n−ヘプタン340gを入れ、HLB3のショ糖ステアリン酸エステル(三菱化学フーズ株式会社製、リョートーシュガーエステルS−370)0.92g及び無水マレイン酸変性エチレン・プロピレン共重合体(三井化学株式会社製、ハイワックス1105A)0.92gを添加し、撹拌しながら80℃まで昇温して界面活性剤を溶解した後、55℃まで冷却した。
300ml容の三角フラスコに、80質量%のアクリル酸水溶液27g(0.3モル)を入れ、外部より冷却しながら、30質量%の水酸化ナトリウム水溶液20g(0.15モル)を滴下して50モル%の中和を行った後、イオン交換水22.6gを加えて溶解し、単量体水溶液を調製した。
還流冷却器、滴下ロート、窒素ガス導入管並びに撹拌機及び撹拌羽根を備えた1000ml容の5つ口円筒型丸底フラスコを準備した。このフラスコに、n−ヘプタン340gを入れ、HLB3のショ糖ステアリン酸エステル(三菱化学フーズ株式会社製、リョートーシュガーエステルS−370)0.92g及び無水マレイン酸変性エチレン・プロピレン共重合体(三井化学株式会社製、ハイワックス1105A)0.92gを添加し、撹拌しながら80℃まで昇温して界面活性剤を溶解した後、55℃まで冷却した。
還流冷却器、滴下ロート、窒素ガス導入管並びに撹拌機及び撹拌羽根を備えた1000ml容の5つ口円筒型丸底フラスコを準備した。このフラスコに、n−ヘプタン340gを入れ、HLB3のショ糖ステアリン酸エステル(三菱化学フーズ株式会社製、リョートーシュガーエステルS−370)0.92g及び無水マレイン酸変性エチレン・プロピレン共重合体(三井化学株式会社製、ハイワックス1105A)0.92gを添加し、撹拌しながら80℃まで昇温して界面活性剤を溶解した後、55℃まで冷却した。
比較例1で得られた水溶性ポリアクリル酸ポリマーを用いてゲル化基剤を調製する際に、水溶性ポリアクリル酸ポリマー5質量部と同時にエチレンジアミン四酢酸二ナトリウム0.2質量部を添加した以外は、実施例1と同様の方法にて膏体層形成用組成物を作製した。
調製した膏体層形成用組成物95〜100gをポリエチレン製容器(アズワン株式会社製、商品名:タイトボーイTB−2)に移し、25℃、相対湿度60%に調整した恒温恒湿器(エスペック株式会社製、商品名:LHU−113型)に入れ、所定時間熟成させた(1,2,3,6,9,12,15,18,24,30,36,48時間)。
調製直後及び所定時間熟成後の膏体層形成用組成物について、カードメーター(アイテクノエンジニアリング社製、商品名:カードメーターMAX、型式:ME−303)を用いて、ゲル強度を測定した。なお、測定条件は、荷重:100g、感圧軸径:16mm、スピード:7秒/インチ、測定モード:ネンチュウである。
[パップ剤の作製]
実施例1において調製した膏体層形成用組成物を用いて、ポリエステル製の不織布(日本バイリーン株式会社製、商品名:貼付薬用基布)の片面に5mm厚で延伸塗布し、引き続き、ゲルの上をナイロンフィルムで覆い、100mm×50mmの大きさに裁断して、パップ剤を作製した。
表1に示す実施例2〜4及び比較例1〜2で得られた膏体層形成用組成物を用いた以外は、実施例5と同様にして、パップ剤をそれぞれ作製した。
パップ剤を製造の際、膏体層形成用組成物を塗工直後のゲルの状態について、目視にて、ままこ(継粉)の有無を確認した。
○:ままこなし
×:ままこあり
Claims (2)
- (メタ)アクリル酸及びその塩からなる群から選ばれた少なくとも1種の(メタ)アクリル酸化合物を重合して含水ゲルを得た後、該含水ゲルの乾燥前又は乾燥中にゲル化速度遅延剤を添加して乾燥することを特徴とする水溶性ポリマー組成物の製造方法であって、
該ゲル化速度遅延剤の添加量が、該(メタ)アクリル酸化合物 100質量部に対して0.1〜10質量部である、水溶性ポリマー組成物の製造方法。 - 請求項1の方法によって得られる水溶性ポリマー組成物に、2〜6価の金属イオンを含む多価金属化合物を添加する工程を含む皮膚貼付剤の膏体層形成用組成物の製造方法。
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