Hydrophilic adhesive masses

Details Hydrophilic adhesive masses Hydrophilic adhesive masses

1999-06-11

2001-03-27

Page, Thurman K. (Department: 1615)

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Web, sheet or filament bases; compositions of bandages; or...

C424S446000, C424S447000, C424S443000

Reexamination Certificate

active

06207184

ABSTRACT:

BACKGROUND OF THE INVENTION
a) Field of the Invention
This invention relates to hydrophilic adhesive masses and hydrophilic plasters, and specifically to hydrophilic adhesive masses, which are strong in adhesiveness and excellent in feeling of use, and also to hydrophilic plasters making use of the same.
b) Description of the Related Art
Hydrophilic plasters each of which carries a hydrophilic mass having adhesiveness and spread as an external preparation on a backing have been used for years. These hydrophilic plasters are required to remain in firm adherence to skin without peeling off during application.
Conventional plasters are known to include non-gelatin poultice composed of polyacrylic acid, a polyacrylate salt, carboxymethylcellulose and an alkali metal alginate (JP 59-110617 A); transdermal preparations composed of polyacrylic acid a 10% aqueous solution of which has a viscosity of from 100 to 1,000 cps, a water-soluble polymer, a polyhydric alcohol and water (JP 6-135828 A); water-containing gel plasters composed of an N-vinylacetamide-sodium acrylate copolymer, a water-soluble aluminum salt and water (JP 9-143060 A); and cataplasms added with polybutene and gelatin (JP 9-208462 A). They are however accompanied with one or more problems such as insufficient adhesiveness and/or difficulty in commercial production.
SUMMARY OF THE INVENTION
There is accordingly a long-standing desire for the provision of a hydrophilic adhesive mass having sufficient adhesiveness.
With the foregoing current circumstance in view, the present inventors have proceeded with extensive research. As a result, it has been found that a hydrophilic adhesive mass containing a copolymer of an aminoalkyl (meth)acrylate and an alkyl (meth)acrylate in a specific proportion has excellent adhesiveness to skin and also provides good feeling of use, leading to the completion of the present invention.
In one aspect of the present invention, there is thus provided a hydrophilic adhesive mass, which comprises 0.05 to 10 wt. % of a copolymer of an aminoalkyl (meth)acrylate and an alkyl (meth)acrylate.
In another aspect of the present invention, there is also provided a hydrophilic plaster comprising a backing and a paste formed of the above-described hydrophilic adhesive mass and at least one pharmacologically active ingredient and spread on the backing.
The hydrophilic adhesive mass and hydrophilic plaster according to the present invention have strong adhesiveness to skin and also provide good feeling of use.
DETAILED DESCRIPTION OF THE INVENTION AND PREFERRED EMBODIMENTS
No particular limitation is imposed on the aminoalkyl (meth)acrylate as one of the monomers making up the copolymer for use in the present invention. Nonetheless, one containing a tertiary amine or a quaternary ammonium salt as an amine moiety in its molecule can be mentioned as a preferred example. Examples of one containing a tertiary amine as an amine moiety in its molecule include dimethylaminoethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, dibutylaminoethyl (meth)acrylate, morpholinoethyl (meth)acrylate, piperidinoethyl (meth)acrylate, dimethylamino-2-propyl (meth)acrylate, and dimethylaminoneopentyl (meth)acrylate.
On the other hand, examples of one containing a quaternary ammonium salt as an amine moiety in its molecule include trimethylammoniumethyl (meth)acrylate, triethylammoniumethyl (meth)acrylate, tributylammoniumethyl (meth)acrylate, trimorpholinoammoniumethyl (meth)acrylate, tripiperidinoammoniumethyl (meth)acrylate, trimethylammonium-2-propyl (meth)acrylate, and trimethylammoniumneopentyl (meth)acrylate. Incidentally, a tertiary amine moiety in a molecule can be converted with hydrochloric acid or the like into its corresponding quaternary ammonium salt moiety. As the aminoalkyl (meth)acrylate, dimethylaminoethyl (meth)acrylate or chlorinated trimethylammoniumethyl (meth)acrylate is particularly preferred.
No particular limitation is imposed on the alkyl (meth)acrylate as the other one of the monomers making up the copolymer. However, preferred examples include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth) acrylate, n-hexyl (meth)acrylate, n-octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, and n-dodecyl (meth)acrylate. They may be used either singly or in combination. In particular, methyl (meth)acrylate, ethyl (meth)acrylate and n-butyl (meth)acrylate are suitably usable.
The copolymer may have any one of random, alternating, block and graft structures, but a block copolymer is preferred.
Examples of the copolymer, which are particularly preferred for use in the present invention, include a block copolymer of dimethylaminoethyl (meth)acrylate, methyl (meth)acrylate and butyl (meth)acrylate; and a block copolymer of chlorinated trimethylammoniumethyl (meth)acrylate, methyl (meth)acrylate and ethyl (meth)acrylate.
As the copolymer for use in the present invention, a commercial product may be employed. Illustrative of such a commercial product are “EUDRAGIT RL 12,5”, “EUDRAGIT RL 100”, “EUDRAGIT RL PO,”, “EUDRAGIT RL 30 D”, “EUDRAGIT RS 12,5”, “EUDRAGIT RS 100”, “EUDRAGIT RS PO,”, “EUDRAGIT RS 30 D”, “EUDRAGIT E 12,5”, “EUDRAGIT E 100”, “PLASTOID E 35 L”, “PLASTOID E 35 M”, “PLASTOID E 35 H” and “PLASTOID L 50” (all, products of Röhm AG).
The proportion of the copolymer employed in the present invention may preferably be set at 0.05 to 10 wt. % based on the whole weight of the hydrophilic adhesive mass, with 0.1 to 6 wt. %, further 0.2 to 4 wt. % being especially preferred. A proportion smaller than 0.05 wt. % makes it difficult to obtain high adhesiveness, while a proportion greater than 10 wt. % cannot bring about extra adhesiveness improving effect and hence, is not economical.
The adhesiveness of the hydrophilic adhesive mass of the present invention can be improved further by incorporating a hydrophilic adhesive in addition to the above-described copolymer. Illustrative of such an hydrophilic adhesive are polyacrylic acids and salts thereof such as polyacrylic acid, sodium polyacrylate, crosslinked branched polyacrylic acid, crosslinked branched sodium polyacrylate, potassium polyacrylate, monoethanolamine polyacrylate, diethanolamine polyacrylate, triethanolamine polyacrylate, and ammonium polyacrylate; copolymers each obtained using acrylic acid or a salt thereof as one of its components, such as starch grafted acrylate, and N-vinylacetamide-sodium acrylate copolymer; cellulose derivatives and salts thereof, such as hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, hydrophobized hydroxypropylmethylcellulose, methylcellulose, and carboxymethylcellulose sodium; polyvinyl alcohol; polyvinylpyrrolidone; polyethylene oxide; methoxyethylene maleic anhydride copolymer; polyacrylamide; alginic acid; sodium alginate; propylene glycol alginate; gelatin; acacia; tragacanth gum; locust bean gum; guar gum; tamarind gum; xanthan gum; gellan gum; carrageenan; and agar. Among these, particularly preferred are polyacrylic acid, sodium polyacrylate, crosslinked branched polyacrylic acid, crosslinked branched sodium polyacrylate, starch grafted acrylate, N-vinylacetamide-sodium acrylate copolymer, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, hydrophobized hydroxypropylmethylcellulose, and carboxymethylcellulose sodium. These hydrophilic adhesives may be used either singly or in combination. Their proportion may preferably range from 0.5 to 50 wt. % based on the whole weight of the mass, with 2 to 40 wt. %, further 3 to 30 wt. % being particularly preferred.
In the present invention, use of a copolymer solubilizer is also preferred to dissolve the copolymer of the aminoalkyl (meth)acrylate and the alkyl (meth)acrylate. No particular limitation is imposed on such a copolymer solubilizer insofar as it can dissolve the copolymer and is pharmaceutically acceptable. It is possible to use, for example, one or more substances selected from polyhydric alcohols, fatty acid esters, surfactants, fatty acids, alcohols and hydrocarbons. Specific examples includes, as p

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