CN1326894C - Combination of acrylic ester containing ester group including partial alkoxyl - Google Patents

Combination of acrylic ester containing ester group including partial alkoxyl Download PDF

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Publication number
CN1326894C
CN1326894C CNB2005100245902A CN200510024590A CN1326894C CN 1326894 C CN1326894 C CN 1326894C CN B2005100245902 A CNB2005100245902 A CN B2005100245902A CN 200510024590 A CN200510024590 A CN 200510024590A CN 1326894 C CN1326894 C CN 1326894C
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methyl
group
ester
och
vinylformic acid
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CN1687159A (en
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毛振民
詹晓平
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Shanghai Jiaotong University
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Shanghai Jiaotong University
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Priority to PCT/CN2006/000509 priority patent/WO2006099818A1/en
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Abstract

The present invention relates to an acrylic ester composition containing groups whose ester groups contain alkoxyl group. The acrylic ester composition comprises the following components: (A) an acrylic ester whose ester groups contain the alkoxyl group, (B) an acrylic ester or an acrylamide monomer, and (C) an optical initiating agent accounting 0.1% to 15% of the mass of the composition. The proportion of monomers A to monomers B can be arbitrarily regulated. Polymer thin films prepared from the composition can be used as controlled release films of a transdermal drug administering system TDDs. The physicochemical properties of the thin films can be finely regulated by regulating the species and the content of the monomers A and the monomers B in the composition so as to quickly prepare the controlled release films of the transdermal drug administering systems suitable for different kinds of medicine.

Description

Comprise ester group partly with the composition of the acrylate of alkoxyl group
Technical field
The present invention relates to a kind of photocurable monomer composition, be specifically related to a kind of ester group that comprises, can be used as the release-controlled film in the preparation transdermal delivery system partly with the composition of the acrylate of alkoxyl group.
Background technology
Transdermal delivery system is meant that medicine discharges from the device of particular design, by complete skin absorption, enters the controlled release drug administration formulation of systemic blood system.Transdermal delivery system can be divided into two big class, i.e. membrane controlled release type and skeleton dispersion patterns basically.The membrane controlled release type transdermal delivery system is that medicine or transdermal absorption accelerator are rolled into the storage storehouse by release-controlled film or other controlled-release materials, by the character control release rate of drugs of release-controlled film or controlled-release material.Scopolamine (trade(brand)name Transderm-Scop), clonidine (trade(brand)name CatapresTTS) are film controlling types in the at present commercially available patch, and controlling diaphragm is a microporous polypropylene membrane; Pannonit (trade(brand)name Transderm-Nitro), fentanyl (trade(brand)name Duragesic), estradiol (trade(brand)name Estraderm), testosterone (trade(brand)name Androderm) are film controlling types, and release-controlled film is a polyethylene vinyl acetate; Nicotine (trade(brand)name trade(brand)name NicoDerm CQ) is a film controlling type, and controlling diaphragm is a polyethylene film.
At European patent No.46069, U.S. Patent No. 3,797 is described in 494 and utilizes microporous membrane control rate of releasing drug.The hole of film from 0.1 to 0.85, the curvature of film from 1 to 10, from 10 to 100 microns of film thicknesses, the film of usefulness has polypropylene, tetrafluoroethylene, polycarbonate, polyvinyl chloride, cellulose acetate, nitrocellulose, polyacrylonitrile etc. for example.Their shortcoming is that the kind of the microporous membrane that can Gong select for use is few, does not satisfy the formulation that more medicine is made percutaneous dosing.
In U.S. Patent No. 6,537, the Scopolamine Patch that is described among the 571B1, U.S. Patent No. 4,681, the Deponit TTS that is described in 584, used release-controlled film all is the multipolymer of ethene-vinyl acetate.Shortcoming is an organic solvent residue problem in the ethylene-vinyl acetate copolymer, and needs constantly to regulate the content of vinyl acetate between to for plastic to regulate the permeability of medicine.
At European patent No.1103260A2, in the clonidine patch that is described among the U.S. Patent No. 2004/0028726A1, utilize vinylformic acid-(2-ethyl) own ester, methyl methacrylate, vinylformic acid and vinyl acetate, Raolical polymerizable takes place, and the multipolymer that obtains can be controlled the release of medicine simultaneously as pressure-sensitive adhesive layer and bin-storing layer in the patch.Shortcoming is that Raolical polymerizable is influenced by several factors, factors such as the time that responds, temperature of reaction, raw material initial concentration, solvent, and also there is the residue problem of organic solvent in patch.
The film of in transdermal delivery system, using, generally speaking the release-controlled film kind lacks, and alternative little, this brings very big obstruction for the exploitation of percutaneous drug administration preparation.
Summary of the invention
The objective of the invention is at the deficiencies in the prior art, a kind of excellent curing performance that has is provided, can produce the monomer composition of the polymkeric substance that can be used for the release-controlled film in the transdermal delivery system.
For the shortcoming that the kind that solves release-controlled film in the existing transdermal delivery system lacks, the present invention finds that on extensive and deep research basis it is abundant to adopt a kind of special photo curable monomer composition just can obtain kind, the release-controlled film of excellent performance.Said composition comprises: (A) a kind of ester group of acrylate partly is with alkoxyl group; (B) a kind of acrylate or acrylamide monomer; (C) a kind of light trigger accounts for 0.1%～15% of composition quality; The ratio of monomer A, B can be regulated arbitrarily in the composition.
The ester group of using among the present invention is partly with the monomer general formula CR of alkoxyl group 2R 1=CR 3COOR 4Expression, wherein R 1, R 2, R 3Be any substituting group, comprise-H ,-CH 3,-C 6H 5,-CH=CH 2,-OH ,-COOH ,-OCH 3,-SO 3H ,-NH 2,-N (CH 3) 3Cl, R 4Be the substituting group that has alkoxyl group, comprise-CH 2OCH 3,-(CH 2) 2OCH 3,-(CH 2) 3OCH 3,-(CH 2) 4OCH 3,-(CH 2) 5OCH 3,-CH 2CH 2OCH 3,-CH 2CH 2OC 2H 5,-CH 2CH 2OC 3H 7,-CH 2CH 2OCH 2OC 6H 5,-C 2H 4CH 2OCH 3,-C 2H 4CH 2OC 2H 5,-C 3H 6CH 2OCH 3,-C 3H 6CH 2OC 2H 5,-C 3H 6CH 2OC 6H 5The monomer of using among the present invention is a 2-butoxy ethyl propenoate, but is not limited only to this monomer, and all ester groups partly contain the acrylate of alkoxyl group can be as this monomer potential alternative.Example can be listed below: (methyl) vinylformic acid-2-methoxyl group ethyl ester, (methyl) vinylformic acid-2-ethoxy ethyl ester, (methyl) vinylformic acid-2-propoxy-ethyl ester, (methyl) vinylformic acid-3-methoxyl group propyl ester, (methyl) vinylformic acid-3-oxyethyl group propyl ester, (methyl) vinylformic acid-3-propoxy-propyl ester, (methyl) vinylformic acid-3-butoxy propyl ester, (methyl) vinylformic acid-2-methoxyl group propyl ester, (methyl) vinylformic acid-2-oxyethyl group propyl ester, (methyl) vinylformic acid-2-propoxy-propyl ester, (methyl) vinylformic acid-2-butoxy propyl ester, (methyl) vinylformic acid-2-phenoxy ethyl, (methyl) vinylformic acid-2-phenoxy group propyl ester, (methyl) vinylformic acid-3-phenoxy group propyl ester, (methyl) vinylformic acid-2-phenoxy group butyl ester, (methyl) vinylformic acid-3-phenoxy group butyl ester, (methyl) vinylformic acid-4-phenoxy group butyl ester, or the like, but be not limited to above listed monomer.
The acrylic ester monomer of using among the present invention can be used general formula CR 2R 1=CR 3COOR 4Expression, wherein R 1, R 2, R 3Can be any substituting group, such as-H ,-CH 3,-C 6H 5,-CH=CH 2,-OH ,-COOH ,-OCH 3,-SO 3H ,-NH 2,-N (CH 3) 3Cl or the like, but be not limited to above listed substituting group.R 4Substituting group can be an alkoxyl group, and example is identical with the acrylate monomer that ester group is partly with alkoxyl group.
R in the described acrylic ester monomer general formula 4Substituting group can be an alkyl also, and the example of using among the present invention is a vinylformic acid n-dodecane ester, but is not limited only to this monomer, all R 4Substituting group is that the acrylate of alkyl can be as this monomer potential alternative.Be exemplified below :-CH 3,-C 2H 5,-C 3H 7,-(CH 2) 3CH 3,-(CH 2) 4CH 3,-(CH 2) 5CH 3,-(CH 2) 7CH 3,-(CH 2) 11CH 3,-CH 2CH=CH 2Or the like, but be not limited to above listed substituting group.
R in the described acrylic ester monomer general formula 4Substituting group can be the group that ester group replaces, and the example of using among the present invention is 1, the 6-hexanediol dimethacrylate, but be not limited only to this monomer, all R 4Substituting group is that the acrylate of the group of ester group replacement can be as this monomer potential alternative.Be exemplified below :-CH 2OOCCH=CH 2,-(CH 2) 2OOCCH=CH 2,-(CH 2) 3OOCCH=CH 2,-(CH 2) 4OOCCH=CH 2,-(CH 2) 5OOCCH=CH 2,-(CH 2) 6OOCCH=CH 2,-(CH 2) 8OOCCH=CH 2,-(CH 2) 2OOCC (CH 3)=CH 2,-(CH 2) 3OOCC (CH 3)=CH 2,-(CH 2) 4OOCC (CH 3)=CH 2,-(CH 2) 5OOCC (CH 3)=CH 2,-(CH 2) 6OOCC (CH 3)=CH 2,-(CH 2) 8OOCC (CH 3)=CH 2Or the like, but be not limited to above listed substituting group.
R in the described acrylic ester monomer general formula 4Substituting group can be the group that hydroxyl replaces, and the example of using among the present invention is 2-hydroxyl-3-phenoxy group propyl acrylate, but is not limited only to this monomer, all R 4Substituting group is that the acrylate of the group of hydroxyl replacement can be as these two monomer potential alternatives.Be exemplified below :-CH 2OH ,-(CH 2) 2OH ,-(CH 2) 3OH ,-(CH 2) 4OH ,-(CH 2) 5OH ,-CH 2CH (OH) CH 3,-CH 2CH (OH) C 2H 5,-CH 2CH (OH) C 3H 7,-CH 2CH (OH) CH 2OC 6H 5,-C 2H 5CH (OH) CH 3,-C 2H 5CH (OH) C 2H 5,-C 3H 6CH (OH) CH 3,-C 3H 6CH (OH) C 2H 5,-C 3H 6(OH) CH 2OC 6H 5Or the like, but be not limited to above listed substituting group.
R in the described acrylic ester monomer general formula 4Substituting group can be the group of carboxyl substituted, and the example of using among the present invention is the 2-carboxy ethyl acrylate, but is not limited only to this monomer, all R 4Substituting group is that the acrylate of the group of carboxyl substituted can be as this monomer potential alternative.Be exemplified below :-CH 2COOH ,-(CH 2) 2COOH ,-(CH 2) 3COOH ,-(CH 2) 4COOH ,-(CH 2) 5COOH ,-(CH 2) 6COOH ,-(CH 2) 8COOH ,-(CH 2) 12COOH or the like, but be not limited to above listed substituting group.
Acrylamide monomer of the present invention can be used general formula CR 2R 1=CR 3CONR 4Expression, wherein R 1, R 2, R 3, R 4Define identical with acrylate monomer.The acrylamide monomers of using among the present invention is N-(1,1-dimethyl-3-oxo butyl)-acrylamide, but is not limited only to this monomer, and all acrylamide monomers can be as this monomer potential alternative.The acrylamide monomers example is exemplified below: (methyl) acrylamide, N, N-dimethyl (methyl) acrylamide, N-sec.-propyl (methyl) acrylamide, N-(butoxymethyl) (methyl) acrylamide, N-(methylol) (methyl) acrylamide, N-[(trishydroxymethyl) methyl] (methyl) acrylamide, N-[3-(dimethylamino) propyl group] (methyl) acrylamide or the like, but be not limited to above listed monomer.
Among the present invention can with light trigger comprise the initiator of the ultraviolet light polymerization that is useful on, as diphenyl peroxide ketone, 1-hydroxycyclohexylphenylketone, bitter almond oil camphor propyl ether, but not only be confined to these light triggers, all are for the UV-light sensitivity, and the light trigger that can trigger monomer be cured reaction is all unrestricted.
The polymeric film that preparation of compositions among the present invention obtains can be used as the release-controlled film in the transdermal delivery system (TDDs), by regulating kind and the content of monomer A, B in the composition, can finely tune the film physical and chemical performance, prepare the release-controlled film in the transdermal delivery system that is applicable to different pharmaceutical fast.Can in mixing solutions, add softening agent when adopting preparation of compositions release-controlled film of the present invention, comprise Citrate trianion, phthalate, sebacate etc., can further improve the physicals of release-controlled film.The present invention has widened the material category of the release-controlled film in the preparation transdermal delivery system, has enlarged the material range of choice.
Description of drawings
Fig. 1 is a 2-butoxy ethyl propenoate and get 30ul, the permeability experiment of the cured film that ultraviolet light polymerization obtains after vinylformic acid n-dodecane ester mixes by mass ratio by quality at 2: 8.
Fig. 2 is a 2-butoxy ethyl propenoate and get 30ul, the permeability experiment of the cured film that ultraviolet light polymerization obtains and the comparison of zoodermic transdermal test in vitro experiment after vinylformic acid-4-hydroxyl butyl ester mixes by mass ratio at 2: 8.
Fig. 3 gets 30ul, the permeability experiment of the cured film that ultraviolet light polymerization obtains after 2-butoxy ethyl propenoate and N-(1,1-dimethyl-3-oxo butyl)-acrylamide mix by mass ratio by quality at 2: 8.
Embodiment
The following example of the present invention proposes for illustration purpose, and is not construed as limiting the invention.
Embodiment 1
2-butoxy ethyl propenoate is mixed by mass ratio by quality with vinylformic acid n-dodecane ester at 2: 8, add the diphenyl peroxide ketone of 5% (w/w) again, dissolving, filter, get mixing solutions 30ul, be placed on the carrier substrates, coating is paved, and places ultraviolet light polymerization instrument completion of cure.
The cured film that obtains places the Franz diffusion cell of improvement, is wintergreen oil solution in the supply pool, and accepting in the pond is the phosphate buffered saline buffer of pH7.4.Utilize the rate of release of efficient liquid phase chromatographic analysis wintergreen oil.See Fig. 1: wintergreen oil is to the permeability experiment (correlation coefficient r=0.9873) of cured film, and cured film has linear controlled-release function to medicine as can be seen from Figure.
Embodiment 2
2-butoxy ethyl propenoate is mixed by mass ratio with vinylformic acid-4-hydroxyl butyl ester at 2: 8, add the diphenyl peroxide ketone of 5% (w/w) again, dissolving, filter, get mixing solutions 30ul, be placed on the carrier substrates, coating is paved, and places ultraviolet light polymerization instrument completion of cure.
The cured film that obtains places the Franz diffusion cell of improvement, is the Tenso-Timelets aqueous solution of 1mg/ml in the supply pool, and accepting in the pond is the phosphate buffered saline buffer of pH7.4.Utilize the rate of release of efficient liquid phase chromatographic analysis Tenso-Timelets.
Animal skin is relatively got fresh Kunming kind small white mouse skin of abdomen and is placed the Franz diffusion cell of improvement, is the Tenso-Timelets aqueous solution of 1mg/ml in the supply pool, and accepting the pond is the phosphate buffered saline buffer of pH7.4.Utilize the rate of release of efficient liquid phase chromatographic analysis Tenso-Timelets.See Fig. 2: curve 1 is that Tenso-Timelets is tested zoodermic transdermal test in vitro, and curve 2 is Tenso-Timelets permeability experiments (correlation coefficient r=0.9901) to cured film, and cured film has linear controlled-release function to medicine as can be seen from Figure.
Embodiment 3
With 2-butoxy ethyl propenoate and N-(1,1-dimethyl-3-oxo butyl)-acrylamide press mass ratio 2: 8 mixing by quality, the diphenyl peroxide ketone that adds 5% (w/w) again, dissolving, filter, get mixing solutions 30ul, be placed on the carrier substrates, coating is paved, and places ultraviolet light polymerization instrument completion of cure.
The cured film that obtains places the Franz diffusion cell of improvement, is wintergreen oil solution in the supply pool, and accepting in the pond is the phosphate buffered saline buffer of pH7.4.Utilize the rate of release of efficient liquid phase chromatographic analysis wintergreen oil.See Fig. 2: wintergreen oil is to the permeability experiment (correlation coefficient r=0.9973) of cured film, and cured film has linear controlled-release function to medicine as can be seen from Figure.
Embodiment 4
With 2-butoxy ethyl propenoate and 1, the 6-hexanediol dimethacrylate is pressed mass ratio mixing in 4: 6 by quality, adds the bitter almond oil camphor propyl ether of 15% (w/w) again, dissolving is filtered, and gets mixing solutions 30ul, be placed on the carrier substrates, coating is paved, and places ultraviolet light polymerization instrument completion of cure.
Embodiment 5
2-butoxy ethyl propenoate is mixed by mass ratio with the 2-carboxy ethyl acrylate at 7: 3, add the 1-hydroxycyclohexylphenylketone of 0.1% (w/w) again, get mixing solutions 30ul, be placed on the carrier substrates, coating is paved, and places ultraviolet light polymerization instrument completion of cure.

Claims (5)

1, a kind of ester group that comprises is partly with the composition of the acrylate of alkoxyl group, and it is characterized in that said composition comprises: (A) a kind of ester group of acrylate is partly with the monomer of alkoxyl group; (B) a kind of acrylate or acrylamide monomer; (C) a kind of light trigger that is used for ultraviolet light polymerization accounts for 0.1%～15% of composition quality; The ratio of monomer A, B can be regulated arbitrarily in the composition;
The ester group of described acrylate is partly with the monomer general formula CR of alkoxyl group 2R 1=CR 3COOR 4Expression, wherein R 1, R 2, R 3Be any substituting group, R 4It is the substituting group that has alkoxyl group; Described acrylate monomer general formula CR 2' R 1'=CR 3' COOR 4' expression, described acrylamide monomer general formula CR 2' R 1'=CR 3' CONR 4' expression, wherein R 1', R 2', R 3' be any substituting group, R 4' be selected from alkoxyl group, alkyl, ester group, hydroxyl or carboxyl.
2,, it is characterized in that the ester group of described acrylate is partly with the R in the monomer of alkoxyl group, acrylate monomer and the acrylamide monomer general formula according to the composition of claim 1 1, R 2, R 3, R 1', R 2', R 3' be selected from independently of one another-H ,-CH 3,-C 6H 5,-CH=CH 2,-OH ,-COOH ,-OCH 3,-SO 3H ,-NH 2Or-N (CH 3) 3Cl.
3, according to the composition of claim 1, the ester group that it is characterized in that described acrylate is partly with the R in the monomer general formula of alkoxyl group 4Be selected from-CH 2OCH 3,-(CH 2) 2OCH 3,-(CH 2) 3OCH 3,-(CH 2) 4OCH 3,-(CH 2) 5OCH 3,-CH 2CH 2OCH 3,-CH 2CH 2OC 2H 5,-CH 2CH 2OC 3H 7,-CH 2CH 2OCH 2OC 6H 5,-C 2H 4CH 2OCH 3,-C 2H 4CH 2OC 2H 5,-C 3H 6CH 2OCH 3,-C 3H 6CH 2OC 2H 5,-C 3H 6CH 2OC 6H 5
4,, it is characterized in that the R in described acrylate monomer and the acrylamide monomer general formula according to the composition of claim 1 4' be selected from-CH 3,-C 2H 5,-C 3H 7,-(CH 2) 3CH 3,-(CH 2) 4CH 3,-(CH 2) 5CH 3,-(CH 2) 7CH 3,-(CH 2) 11CH 3,-CH 2CH=CH 2,-CH 2OH ,-(CH 2) 2OH ,-(CH 2) 3OH ,-(CH 2) 4OH ,-(CH 2) 5OH ,-CH 2CH (OH) CH 3,-CH 2CH (OH) C 2H 5,-CH 2CH (OH) C 3H 7,-CH 2CH (OH) CH 2OC 6H 5,-C 2H 5CH (OH) CH 3,-C 2H 5CH (OH) C 2H 5,-C 3H 6CH (OH) CH 3,-C 3H 6CH (OH) C 2H 5,-C 3H 6(OH) CH 2OC 6H 5,-CH 2OOCCH=CH 2,-(CH 2) 2OOCCH=CH 2,-(CH 2) 3OOCCH=CH 2,-(CH 2) 4OOCCH=CH 2,-(CH 2) 5OOCCH=CH 2,-(CH 2) 6OOCCH=CH 2,-(CH 2) 8OOCCH=CH 2,-(CH 2) 2OOCC (CH 3)=CH 2,-(CH 2) 3OOCC (CH 3)=CH 2,-(CH 2) 4OOCC (CH 3)=CH 2,-(CH 2) 5OOCC (CH 3)=CH 2,-(CH 2) 6OOCC (CH 3)=CH 2,-(CH 2) 8OOCC (CH 3)=CH 2,-CH 2COOH ,-(CH 2) 2COOH ,-(CH 2) 3COOH ,-(CH 2) 4COOH ,-(CH 2) 5COOH ,-(CH 2) 6COOH ,-(CH 2) 8COOH ,-(CH 2) 12COOH ,-CH 2OCH 3,-(CH 2) 2OCH 3,-(CH 2) 3OCH 3,-(CH 2) 4OCH 3,-(CH 2) 5OCH 3,-CH 2CH 2OCH 3,-CH 2CH 2OC 2H 5,-CH 2CH 2OC 3H 7,-CH 2CH 2OCH 2OC 6H 5,-C 2H 4CH 2OCH 3,-C 2H 4CH 2OC 2H 5,-C 3H 6CH 2OCH 3,-C 3H 6CH 2OC 2H 5Or-C 3H 6CH 2OC 6H 5
5, according to the composition of claim 1, the monomer that the ester group that it is characterized in that described acrylate is partly with alkoxyl group is selected from 2-butoxy ethyl propenoate, (methyl) vinylformic acid-2-methoxyl group ethyl ester, (methyl) vinylformic acid-2-ethoxy ethyl ester, (methyl) vinylformic acid-2-propoxy-ethyl ester, (methyl) vinylformic acid-3-methoxyl group propyl ester, (methyl) vinylformic acid-3-oxyethyl group propyl ester, (methyl) vinylformic acid-3-propoxy-propyl ester, (methyl) vinylformic acid-3-butoxy propyl ester, (methyl) vinylformic acid-2-methoxyl group propyl ester, (methyl) vinylformic acid-2-oxyethyl group propyl ester, (methyl) vinylformic acid-2-propoxy-propyl ester, (methyl) vinylformic acid-2-butoxy propyl ester, (methyl) vinylformic acid-2-phenoxy ethyl, (methyl) vinylformic acid-2-phenoxy group propyl ester, (methyl) vinylformic acid-3-phenoxy group propyl ester, (methyl) vinylformic acid-2-phenoxy group butyl ester, (methyl) vinylformic acid-3-phenoxy group butyl ester or (methyl) vinylformic acid-4-phenoxy group butyl ester; Described acrylate monomer is selected from vinylformic acid n-dodecane ester, 1,6-hexanediol dimethacrylate, 2-hydroxyl-3-phenoxy group propyl acrylate or 2-carboxy ethyl acrylate; Described acrylamide monomer is selected from N-(1,1-dimethyl-3-oxo butyl)-and acrylamide, (methyl) acrylamide, N, N-dimethyl (methyl) acrylamide, N-sec.-propyl (methyl) acrylamide, N-(butoxymethyl) (methyl) acrylamide, N-(methylol) (methyl) acrylamide, N-[(trishydroxymethyl) methyl] (methyl) acrylamide or N-[3-(dimethylamino) propyl group] (methyl) acrylamide.
CNB2005100245902A 2005-03-24 2005-03-24 Combination of acrylic ester containing ester group including partial alkoxyl Expired - Fee Related CN1326894C (en)

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PCT/CN2006/000509 WO2006099818A1 (en) 2005-03-24 2006-03-24 Light curable monomer compostion and use thereof

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1045355A (en) * 1988-12-22 1990-09-19 Lts洛曼医疗系统公司 A kind ofly be used to produce to contain the method for calabar bean alkali as the Transcutaneous Therapeutic System of active component
CN1097635A (en) * 1993-07-22 1995-01-25 计威康 Medicine pressure-sensitive adhesive electrode
EP0913445A1 (en) * 1997-10-28 1999-05-06 National Starch and Chemical Investment Holding Corporation Enhancer tolerant pressure sensitive adhesives for transdermal drug delivery
WO2003101433A1 (en) * 2002-05-28 2003-12-11 LABTEC Gesellschaft für technologische Forschung und Entwicklung mbH Plaster containing fentanyl
US20040131826A1 (en) * 2003-01-06 2004-07-08 General Electric Company Radiation curable microstructure-bearing articles
CN1545408A (en) * 2001-08-24 2004-11-10 LTS��������ϵͳ�ɷݹ�˾ Transdermal therapeutic system based on polyacrylate-contact-bonding adhesives without functional groups

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1045355A (en) * 1988-12-22 1990-09-19 Lts洛曼医疗系统公司 A kind ofly be used to produce to contain the method for calabar bean alkali as the Transcutaneous Therapeutic System of active component
CN1097635A (en) * 1993-07-22 1995-01-25 计威康 Medicine pressure-sensitive adhesive electrode
EP0913445A1 (en) * 1997-10-28 1999-05-06 National Starch and Chemical Investment Holding Corporation Enhancer tolerant pressure sensitive adhesives for transdermal drug delivery
CN1545408A (en) * 2001-08-24 2004-11-10 LTS��������ϵͳ�ɷݹ�˾ Transdermal therapeutic system based on polyacrylate-contact-bonding adhesives without functional groups
WO2003101433A1 (en) * 2002-05-28 2003-12-11 LABTEC Gesellschaft für technologische Forschung und Entwicklung mbH Plaster containing fentanyl
US20040131826A1 (en) * 2003-01-06 2004-07-08 General Electric Company Radiation curable microstructure-bearing articles

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