JPH0363530B2 - - Google Patents
Info
- Publication number
- JPH0363530B2 JPH0363530B2 JP57046599A JP4659982A JPH0363530B2 JP H0363530 B2 JPH0363530 B2 JP H0363530B2 JP 57046599 A JP57046599 A JP 57046599A JP 4659982 A JP4659982 A JP 4659982A JP H0363530 B2 JPH0363530 B2 JP H0363530B2
- Authority
- JP
- Japan
- Prior art keywords
- pressure
- drug
- copolymer
- sensitive adhesive
- alkali metal
- 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.)
- Expired - Lifetime
Links
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 30
- 229940079593 drug Drugs 0.000 claims description 30
- 239000003814 drug Substances 0.000 claims description 30
- 229920001577 copolymer Polymers 0.000 claims description 26
- 239000002390 adhesive tape Substances 0.000 claims description 18
- 230000001225 therapeutic effect Effects 0.000 claims description 18
- 229910052783 alkali metal Inorganic materials 0.000 claims description 16
- 150000001340 alkali metals Chemical class 0.000 claims description 15
- -1 acrylic ester Chemical class 0.000 claims description 14
- 239000010410 layer Substances 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 8
- 238000007334 copolymerization reaction Methods 0.000 claims description 7
- 239000002585 base Substances 0.000 claims description 6
- 150000003839 salts Chemical group 0.000 claims description 6
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- 239000011505 plaster Substances 0.000 claims description 3
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 claims description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000853 adhesive Substances 0.000 description 11
- 230000001070 adhesive effect Effects 0.000 description 11
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 6
- 238000002845 discoloration Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 229960000905 indomethacin Drugs 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 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 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-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
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 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
- ZVYGIPWYVVJFRW-UHFFFAOYSA-N 3-methylbutyl prop-2-enoate Chemical compound CC(C)CCOC(=O)C=C ZVYGIPWYVVJFRW-UHFFFAOYSA-N 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 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
- 229920000298 Cellophane Polymers 0.000 description 1
- 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 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000003851 corona treatment Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- LPEPZBJOKDYZAD-UHFFFAOYSA-N flufenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 LPEPZBJOKDYZAD-UHFFFAOYSA-N 0.000 description 1
- 229960004369 flufenamic acid Drugs 0.000 description 1
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 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
- 230000007721 medicinal effect Effects 0.000 description 1
- 229960003464 mefenamic acid Drugs 0.000 description 1
- HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000002987 primer (paints) Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229960004025 sodium salicylate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 229940126585 therapeutic drug 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
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Medicinal Preparation (AREA)
Description
本発明は治療用接着テープもしくはシートに関
する。
基材に、治療用薬剤を混入させた感圧性接着剤
層が薄層状に設けられた硬膏剤である治療用接着
テープもしくはシートを皮膚に貼付け、感圧性接
着剤層から滲出する薬剤により局所治療を行なう
ことが、従来の密封包帯治療法(ODT療法)に
代る新たな治療方法として注目されている。
このような治療用接着テープもしくはシートに
要求される性能は、感圧性接着剤が皮膚に対し強
い刺激を与えないこと、皮膚に貼付しやすく剥す
に際して糊残りや過度な接着力により苦痛を与え
ないこと、感圧性接着剤と薬剤との間の相互化学
作用がないこと、薬効が充分得られるように薬剤
が粘着剤中から表面に滲出しやすいこと等であ
る。
従来はこの目的に供する感圧性接着剤として、
カルボキシル基を有する単量体とアクリル酸エス
テル又は(及び)メタクリル酸エステルを共重合
成分とする共重合体からなるものが使用され、こ
の感圧性接着剤層に薬剤を含有させているが、薬
剤として酸性で不安定なものが使用れた場合に
は、熱により極めて速く薬剤が変質したり、有色
薬剤では変色が見られたりする他、内部凝集力が
不足して貼着後これを引剥した際に貼着面に感圧
性接着剤が付着する(糊残留)現象をきたすおそ
れがあつた。
本発明はかゝる欠点を解消することを目的とし
てなされたものであり、その要旨とするところ
は、基材に、薬剤を含有する感圧性接着剤層が設
けられた硬膏剤である治療用接着テープもしくは
シートにおいて、感圧性接着剤が(A)カルボキシル
基を1乃至2個有するα,β不飽和カルボン酸
0.1乃至20重量%と、(B)アクリル酸エステル又は
(及び)メタクリル酸エステルとを共重合成分と
して含有する水不溶性共重合体であつて、該共重
合体におけるカルボキシル基がアルカリ金属又は
(及び)アルカリ士類金属の塩とされていること
を特徴とする、治療用接着テープもしくはシート
に存する。
次に本発明治療用接着テープもしくはシートに
ついて更に詳細に説明する。
本発明における基材としては、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、軟質ポリ塩化ビニル、セロハン等の可撓性を
有する材質が好適であり、基材の厚みとしては
0.02乃至0.15mmの範囲が好ましい。
前記基材には必要に応じ感圧性接着剤との密着
力を高めるために、コロナ放電処理、プラズマ処
理、下塗剤塗工等が施される。
感圧性接着剤は、(A)カルボキシル基を1乃至2
個有するα,β不飽和カルボン酸と、(B)アクリル
酸エステル又は(及び)メタクリル酸エステルと
を共重合成分として含有する水不溶性共重合体か
らなる。
前記(A)成分としては、例えばアクリル酸、メタ
クリル酸、クロトン酸、マレイン酸、イタコン酸
等が好適であり、共重合成分量としては0.1乃至
20重量%とされる。
前記(B)成分としては、エステル残基として例え
ばメチル基、エチル基プロピル基、イソプロピル
基、n−ブチル基、イソブチル基、n−ペンチル
基、イソペンチル基、2−メチルブチル基、n−
ヘキシル基、2−メチルペンチル基、3−メチル
ペンチル基、2−エチルブチル基、n−オクチル
基、イソオクチル基、2−エチルヘキシル基、ノ
ニル基、n−デシル基、ラウリル基等を有するも
のが使用される。
そして特に好適なアクリル酸エステルとしては
エチルアクリレート、n−ブチルアクリレート、
イソブチルアクリレート、イソアミルアクリレー
ト、2−エチルヘキシルアクリレート、n−オク
チルアクリレート、ラウリルアクリレート等であ
り、又メタクリル酸エステルとしては、メチルメ
タクリレート、ブチルメタクリレート、2−エチ
ルヘキシルメタクリレート、n−オクチルメタク
リレート、ラウリルメタクリレート等である。
共重合体としては前記(A),(B)成分の他に、(C)こ
れらと共重合可能な他の単量体を共重合成分とし
て含有することができる。
前記(C)成分としては、例えばアクリルアミド、
酢酸ビニル、アクリロニトリル、スチレン、塩化
ビニル、塩化ビニリデン、エチレン、プロピレ
ン、ブタジエン、イソプレン、等が使用に適す
る。
前記(A),(B)成分を共重合成分とする共重合体、
又は、前記(A),(B)成分の他に(C)これらと共重合可
能な他の単量体を共重合成分とする共重合体を得
るには、通常のラジカル重合触媒、例えばアゾビ
ス系化合物、過酸化系化合物を用いることにより
溶液重合、エマルジヨン重合、懸濁重合等を行な
えばよいが、後工程となる薬剤の混合、溶解工程
を考えると溶液重合が最適である。例えば反応容
器内に、前記(A),(B)成分及び必要に応じて(C)成分
を加え、酢酸エチル等の溶媒を加えて約60重量%
濃度の溶液となし、反応容器内の雰囲気を窒素ガ
スで置換し、撹拌しながら昇温し、60乃至80℃の
温度において、ラジカル発生触媒を同じ溶媒によ
つて溶解した溶液を滴下するか分割注入し、粘度
の上昇に応じて溶媒のみを追加しながら粘度を抑
制し、10乃至20時間で重合を完了する。
かくして得られる共重合体は、そのまゝでは治
療用接着テープもしくはシートの感圧性接着剤と
して不満足なものとしかならない。その理由は、
かゝる共重合体は内部凝集力が不足したものとな
り貼着後これを引剥した際に貼着面に感圧性接着
剤が付着する(糊残留)現象をきたすおそれがあ
ること、薬剤には酸性で不安定なものが使用され
ることが多いが共重合体はカルボキシル基を有す
るので60〜80℃程度の熱により変質したり、有色
薬剤では変色したりしやすいこと等の問題点を有
するからである。
このために本発明では、前記共重合体における
カルボキシル基をアルカリ金属又は(及び)アル
カリ士類金属の塩とするものである。アルカリ金
属、アルカリ士類金属としては、例えばナトリウ
ム、カリウム、マグネシウム、カルシウム等が使
用される。
又、アルカリ金属又は(及び)アルカリ士類金
属の塩とするには、前記共重合体に例えば水酸化
リチウム、ナトリウムエチラート、水酸化ナトリ
ウム、水酸化カリウム、水酸化マグネシウム、酸
化マグネシウム、水酸化カルシウム等を適宜加熱
条件下に接触させればよい。
前記共重合体のカルボキシル基は80モル%以上
が、アルカリ金属又は(及び)アルカリ士類金属
の塩とされるのが好ましい。これは80モル%より
も少量の場合には、薬剤として酸性に不安定なも
のが使用されていると熱を受けたりした際に変色
したり有色薬剤の変色を生じたりしやすいものと
なり、又共重合体の内部凝集力も不充分なものと
なりやすいからである。
薬剤としては、例えばサリチル酸ナトリウム、
メフエナミン酸、フルフエナミン酸、アセチルサ
リチル酸、インドメタシン等が使用される。薬剤
の量は、感圧性接着剤層の厚み、薬剤の種類等に
より異なるが、感圧性接着剤層1cm2当り1μg〜
5mgの範囲が好適である。
感圧性接着剤は基材に塗布、乾燥され、次いで
剥離性シートをロール等を通して圧着するか、又
は、先に剥離性シートの面上に感圧性接着剤の溶
液を塗布、乾燥し、ロールを通して基材を粘着面
上に圧着することにより、感圧性接着剤層が保護
された治療用接着テープもしくはシートが得られ
る。
本発明によれば、感圧性接着剤が前記(A),(B)成
分を共重合成分として含有する共重合体であつ
て、該共重合体におけるカルボキシル基がアルカ
リ金属又は(及び)アルカリ士類金属の塩とされ
ているので、感圧性接着剤は適当な内部凝集力を
有するものとなり粘着面への糊残留を生じないも
のとなり、又薬剤の滲出性が良好なものとなる。
更に薬剤として酸に対し不安定なものが使用され
ても熱による変質や変色をきたすのが防がれ、又
感圧性接着剤層の表面に薬剤が析出したりするこ
とがないものとなる。
実施例 1
2−エチルヘキシルメタクリレート 55g
n−ブチルアクリレート 38g
エチルアクリレート 4g
アクリル酸 2.5g
上記各成分を反応容器に入れ、触媒としてアゾ
ビスイソブチロニトリル0.5g、溶剤として酢酸
エチルを加え、70℃で溶液重合し、固形分が40重
量%の共重合体溶液を得た。
次いで上記の共重合体溶液100gに酢酸エチル
50gを加えて均一に溶解し、これにナトリウムエ
チラート0.898gを酢酸エチル10g、エタノール
10gの混合液に均一分散させたものを加えた。次
いで70℃で1時間加熱しながら撹拌を行ない、更
にナトリウムエチラートの0.68重量%酢酸エチル
−エタノール溶液を10g滴下した。30分間撹拌を
継続した後、水を10mlを加え、PH値を測定したと
ころ、7.77であつた。また共重合体のカルボキシ
ル基は80モル%以上がナトリウム塩になつてい
た。
次いでこの感圧性接着剤溶液(固形分25.4%)
に薬剤としてインドメタシン2.54gを混合し、得
られた溶液をポリエチレンフイルム上に塗布し、
70℃で20分間乾燥し、治療用接着テープを得た。
この治療用接着テープの、感圧性接着剤層の厚み
は63.5μmであり、皮膚に貼着したところ剥れも
なく、又貼着後引剥す際の痛みも生じなかつた。
この治療用接着テープは製造した直後と、60℃
で7日間放置した後の薬剤の変色の有無、薬剤の
感圧性接着剤との相溶性、薬剤の感圧性接着剤層
からの滲出性薬剤の変質の有無を判定した結果を
第1表に示す。
尚薬剤の変色の有無は、感圧性接着剤層の色調
の変化から判定した。又薬剤滲出性は治療用接着
テープから直径66mmの円形試験片を打抜き、メタ
ノール25ml、水25mlの混合液中に24時間浸漬し、
薬剤を抽出し、抽出された薬剤量を液体クロマト
グラフイーにかけて定量した。又薬剤の変質の有
無は、液体クロマトグラフイーにおいて標準薬物
と同じピークを有するか否かにより判定した。
The present invention relates to therapeutic adhesive tapes or sheets. A therapeutic adhesive tape or sheet, which is a plaster with a thin layer of pressure-sensitive adhesive mixed with a therapeutic drug mixed into the base material, is applied to the skin, and the drug oozes from the pressure-sensitive adhesive layer for local treatment. is attracting attention as a new treatment method to replace the conventional occlusive dressing therapy (ODT therapy). The performance required for such therapeutic adhesive tapes or sheets is that the pressure-sensitive adhesive does not cause strong irritation to the skin, and that it is easy to apply to the skin and does not cause pain due to adhesive residue or excessive adhesive force when removed. In addition, there is no mutual chemical interaction between the pressure-sensitive adhesive and the drug, and the drug easily oozes out from the adhesive to the surface so that a sufficient medicinal effect can be obtained. Conventionally, pressure-sensitive adhesives used for this purpose,
A copolymer consisting of a monomer having a carboxyl group and an acrylic ester or (and) a methacrylic ester is used, and this pressure-sensitive adhesive layer contains a drug. If an acidic and unstable substance is used, the drug will deteriorate extremely quickly due to heat, and if it is a colored drug, discoloration may be observed, and the internal cohesive force may be insufficient, making it difficult to peel off the drug after it has been applied. When doing so, there was a risk that the pressure-sensitive adhesive would adhere to the adhesive surface (adhesive residue). The present invention has been made with the aim of eliminating such drawbacks, and its gist is to provide a therapeutic plaster that has a pressure-sensitive adhesive layer containing a drug on the base material. In the adhesive tape or sheet, the pressure-sensitive adhesive is (A) an α,β unsaturated carboxylic acid having 1 or 2 carboxyl groups;
A water-insoluble copolymer containing 0.1 to 20% by weight of (B) an acrylic ester or (and) a methacrylic ester as a copolymerization component, wherein the carboxyl group in the copolymer contains an alkali metal or (and) ) A therapeutic adhesive tape or sheet characterized by being a salt of an alkali metal. Next, the therapeutic adhesive tape or sheet of the present invention will be explained in more detail. The base material in the present invention includes polyethylene,
Flexible materials such as polypropylene, ethylene-vinyl acetate copolymer, soft polyvinyl chloride, and cellophane are suitable, and the thickness of the base material is
A range of 0.02 to 0.15 mm is preferred. If necessary, the base material is subjected to corona discharge treatment, plasma treatment, primer coating, etc. in order to increase the adhesion with the pressure-sensitive adhesive. The pressure-sensitive adhesive has (A) 1 to 2 carboxyl groups.
It consists of a water-insoluble copolymer containing an individual α,β unsaturated carboxylic acid and (B) an acrylic ester or (and) a methacrylic ester as copolymerization components. As the component (A), for example, acrylic acid, methacrylic acid, crotonic acid, maleic acid, itaconic acid, etc. are suitable, and the copolymerization amount is 0.1 to 1.
It is said to be 20% by weight. Component (B) includes ester residues such as methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, n-pentyl group, isopentyl group, 2-methylbutyl group, n-
Those having a hexyl group, 2-methylpentyl group, 3-methylpentyl group, 2-ethylbutyl group, n-octyl group, isooctyl group, 2-ethylhexyl group, nonyl group, n-decyl group, lauryl group, etc. are used. Ru. Particularly suitable acrylic esters include ethyl acrylate, n-butyl acrylate,
Isobutyl acrylate, isoamyl acrylate, 2-ethylhexyl acrylate, n-octyl acrylate, lauryl acrylate, etc., and methacrylic acid esters include methyl methacrylate, butyl methacrylate, 2-ethylhexyl methacrylate, n-octyl methacrylate, lauryl methacrylate, etc. . In addition to components (A) and (B), the copolymer may contain (C) another monomer copolymerizable with these components as a copolymerization component. As the component (C), for example, acrylamide,
Vinyl acetate, acrylonitrile, styrene, vinyl chloride, vinylidene chloride, ethylene, propylene, butadiene, isoprene, and the like are suitable for use. A copolymer containing the components (A) and (B) as copolymerization components,
Alternatively, in order to obtain a copolymer containing, in addition to components (A) and (B), (C) another monomer copolymerizable with these components, a common radical polymerization catalyst such as azobis Although solution polymerization, emulsion polymerization, suspension polymerization, etc. may be carried out by using a peroxide-based compound or a peroxide-based compound, solution polymerization is optimal in consideration of the subsequent steps of mixing and dissolving the drug. For example, add the above (A), (B) components and optionally (C) component into a reaction container, add a solvent such as ethyl acetate, and add about 60% by weight.
Prepare a concentrated solution, replace the atmosphere in the reaction vessel with nitrogen gas, raise the temperature while stirring, and at a temperature of 60 to 80°C, drop or divide a solution in which the radical generating catalyst is dissolved in the same solvent. Polymerization is completed in 10 to 20 hours by adding only the solvent as the viscosity increases and controlling the viscosity. The copolymers thus obtained are only unsatisfactory as pressure-sensitive adhesives for therapeutic adhesive tapes or sheets. The reason is,
Such copolymers lack internal cohesive strength, which may cause the pressure-sensitive adhesive to stick to the adhesive surface (adhesive residue) when the adhesive is peeled off after application. Copolymers that are acidic and unstable are often used, but since copolymers have carboxyl groups, they have problems such as being easily altered by heat of about 60 to 80 degrees Celsius, and easily discoloring with colored drugs. This is because it has. For this purpose, in the present invention, the carboxyl group in the copolymer is an alkali metal or/and an alkali metal salt. Examples of the alkali metals and alkali metals used include sodium, potassium, magnesium, and calcium. In addition, to form a salt of an alkali metal or (and) an alkali metal, the copolymer may be added with, for example, lithium hydroxide, sodium ethylate, sodium hydroxide, potassium hydroxide, magnesium hydroxide, magnesium oxide, hydroxide. Calcium or the like may be contacted under appropriate heating conditions. Preferably, 80 mol% or more of the carboxyl groups in the copolymer are salts of alkali metals and/or alkali metals. If the amount is less than 80 mol%, if the drug is acid-unstable, it may discolor when exposed to heat, or the colored drug may discolor. This is because the internal cohesive force of the copolymer tends to be insufficient. Examples of drugs include sodium salicylate,
Mefenamic acid, flufenamic acid, acetylsalicylic acid, indomethacin, etc. are used. The amount of drug varies depending on the thickness of the pressure-sensitive adhesive layer, the type of drug, etc., but is 1 μg or more per 1 cm 2 of the pressure-sensitive adhesive layer.
A range of 5 mg is preferred. The pressure-sensitive adhesive is applied to the base material and dried, and then a releasable sheet is pressed through a roll or the like, or a solution of the pressure-sensitive adhesive is first applied onto the surface of the releasable sheet, dried, and then the pressure-sensitive adhesive is applied through a roll. By pressing the substrate onto the adhesive surface, a therapeutic adhesive tape or sheet with a protected pressure-sensitive adhesive layer is obtained. According to the present invention, the pressure-sensitive adhesive is a copolymer containing the components (A) and (B) as copolymerization components, and the carboxyl group in the copolymer is an alkali metal or (and) an alkali metal. Since it is a salt of a similar metal, the pressure-sensitive adhesive has an appropriate internal cohesive force, does not leave adhesive residue on the adhesive surface, and has good exudation properties of the drug.
Furthermore, even if a chemical that is unstable to acids is used, deterioration or discoloration due to heat is prevented, and the chemical does not precipitate on the surface of the pressure-sensitive adhesive layer. Example 1 2-ethylhexyl methacrylate 55g n-butyl acrylate 38g ethyl acrylate 4g acrylic acid 2.5g The above components were placed in a reaction vessel, 0.5g of azobisisobutyronitrile was added as a catalyst, and ethyl acetate was added as a solvent, and the mixture was heated at 70°C. Solution polymerization was performed to obtain a copolymer solution with a solid content of 40% by weight. Next, add ethyl acetate to 100 g of the above copolymer solution.
Add 50g and dissolve uniformly, add 0.898g of sodium ethylate, 10g of ethyl acetate, and ethanol.
The uniformly dispersed mixture was added to 10 g of the mixed liquid. Next, stirring was performed while heating at 70° C. for 1 hour, and 10 g of a 0.68% by weight ethyl acetate-ethanol solution of sodium ethylate was added dropwise. After continuing stirring for 30 minutes, 10 ml of water was added and the pH value was measured and found to be 7.77. In addition, more than 80 mol% of the carboxyl groups in the copolymer were sodium salts. Then this pressure sensitive adhesive solution (solids content 25.4%)
2.54 g of indomethacin was mixed as a drug, and the resulting solution was applied onto a polyethylene film.
It was dried at 70°C for 20 minutes to obtain a therapeutic adhesive tape.
The pressure-sensitive adhesive layer of this therapeutic adhesive tape had a thickness of 63.5 μm, and when it was applied to the skin, it did not peel off, nor did it cause any pain when it was removed after being applied. This therapeutic adhesive tape can be used immediately after manufacturing and at 60°C.
Table 1 shows the results of determining the presence or absence of discoloration of the drug after being left for 7 days, the compatibility of the drug with the pressure-sensitive adhesive, and the presence or absence of deterioration in the quality of the drug exuded from the pressure-sensitive adhesive layer. . The presence or absence of discoloration of the drug was determined from the change in color tone of the pressure-sensitive adhesive layer. In addition, drug exudation was determined by punching a circular test piece with a diameter of 66 mm from a therapeutic adhesive tape and immersing it in a mixture of 25 ml of methanol and 25 ml of water for 24 hours.
The drug was extracted, and the amount of the extracted drug was determined by liquid chromatography. The presence or absence of deterioration of the drug was determined by whether it had the same peak as the standard drug in liquid chromatography.
【表】【table】
【表】
比較例 1
実施例1と同じ各成分を用い、実施例1と同様
にして固形分が40重量%の共重合体溶液を得た。
次いでこの共重合体溶液を用いて実施例1と同
様にインドメタシン2.54gを混合し、この溶液を
ポリエチレンフイルム上に塗布し、70℃で20分間
乾燥し治療用接着テープを得た。
この治療用接着テープにおける薬剤は60℃で7
日間放置後変色をきたしていることが、感圧性接
着剤層の色調が暗褐色に変化していることから認
められた。又、実施例1と同様にして薬剤を抽出
し、この抽出液を液体クロマトグラフイーで測定
したところ、製造直後の場合は標準薬物ピークと
何ら変りがなかつたが、60℃で7日間放置後の場
合は、試料ピークが2箇所にあり、明らかに変質
していることが確認された。[Table] Comparative Example 1 Using the same components as in Example 1, a copolymer solution with a solid content of 40% by weight was obtained in the same manner as in Example 1. Next, using this copolymer solution, 2.54 g of indomethacin was mixed in the same manner as in Example 1, and this solution was applied onto a polyethylene film and dried at 70° C. for 20 minutes to obtain a therapeutic adhesive tape. The drug in this therapeutic adhesive tape is 7°C at 60°C.
Discoloration was observed after being left for one day, as the color tone of the pressure-sensitive adhesive layer changed to dark brown. Furthermore, when the drug was extracted in the same manner as in Example 1 and this extract was measured using liquid chromatography, there was no difference from the standard drug peak immediately after manufacture, but after leaving it at 60°C for 7 days. In the case of , the sample peaks were at two locations, and it was confirmed that the quality had clearly changed.
Claims (1)
けられた硬膏剤である治療用接着テープもしくは
シートにおいて、感圧性接着剤が(A)カルボキシル
基を1乃至2個有するα,β不飽和カルボン酸
0.1乃至20重量%と、 (B)アクリル酸エステル又は(及び)メタクリル酸
エステルとを共重合成分として含有する水不溶性
共重合体であつて、該共重合体におけるカルボキ
シル基がアルカリ金属又は(及び)アルカリ士類
金属の塩とされていることを特徴とする、治療用
接着テープもしくはシート 2 共重合体が前記(A),(B)成分の他に、(C)これら
と共重合可能な他の単量体を共重合成分とするこ
とを特徴とする、特許請求の範囲第1項記載の治
療用接着テープもしくはシート 3 共重合体におけるカルボキシル基の80モル%
以上がアルカリ金属又は(及び)アルカリ士類金
属の塩とされていることを特徴とする、特許請求
の範囲第1項又は第2項記載の治療用接着テープ
もしくはシート。[Scope of Claims] 1. A therapeutic adhesive tape or sheet that is a plaster having a pressure-sensitive adhesive layer containing a drug on a base material, wherein the pressure-sensitive adhesive has (A) 1 to 2 carboxyl groups. alpha, beta unsaturated carboxylic acid
A water-insoluble copolymer containing 0.1 to 20% by weight of (B) an acrylic ester or (and) a methacrylic ester as a copolymerization component, wherein the carboxyl group in the copolymer contains an alkali metal or (and) ) Therapeutic adhesive tape or sheet 2, characterized in that it is a salt of an alkali metal. In addition to the above-mentioned components (A) and (B), (C) the copolymer is copolymerizable with these. Therapeutic adhesive tape or sheet 3 according to claim 1, characterized in that other monomers are copolymerized components. 80 mol% of carboxyl groups in the copolymer.
The therapeutic adhesive tape or sheet according to claim 1 or 2, characterized in that the above is an alkali metal or/and a salt of an alkali metal.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4659982A JPS58164506A (en) | 1982-03-24 | 1982-03-24 | Adhesive tape or sheet for medical use |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4659982A JPS58164506A (en) | 1982-03-24 | 1982-03-24 | Adhesive tape or sheet for medical use |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS58164506A JPS58164506A (en) | 1983-09-29 |
JPH0363530B2 true JPH0363530B2 (en) | 1991-10-01 |
Family
ID=12751759
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP4659982A Granted JPS58164506A (en) | 1982-03-24 | 1982-03-24 | Adhesive tape or sheet for medical use |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS58164506A (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH03127728A (en) * | 1989-10-13 | 1991-05-30 | Sekisui Chem Co Ltd | Adhesive base for remedy and adhesive mass layer for remedy using same |
JP4727839B2 (en) * | 2001-04-16 | 2011-07-20 | 日東電工株式会社 | Medical hygiene pressure-sensitive adhesive composition and pressure-sensitive adhesive tape or sheet using the composition |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS50140624A (en) * | 1974-04-30 | 1975-11-11 |
-
1982
- 1982-03-24 JP JP4659982A patent/JPS58164506A/en active Granted
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS50140624A (en) * | 1974-04-30 | 1975-11-11 |
Also Published As
Publication number | Publication date |
---|---|
JPS58164506A (en) | 1983-09-29 |
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