Hydrophilic polymers, pressure sensitive adhesives and coatings

Details Hydrophilic polymers, pressure sensitive adhesives and coatings Hydrophilic polymers, pressure sensitive adhesives and coatings

2001-01-10

2003-11-25

Zalukaeva, Tatyana (Department: 1713)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Polymers from only ethylenic monomers or processes of...

C526S230000, C526S317100, C526S318420, C526S318400, C526S319000, C526S329200, C526S328500, C526S325000, C526S312000

Reexamination Certificate

active

06653427

ABSTRACT:

FIELD OF THE INVENTION
This invention is related to the method of preparing hydrophilic homopolymers and copolymers and to their use as pressure sensitive adhesives, hydrogels, coatings and compositions suitable for topical application to skin.
BACKGROUND OF THE INVENTION
The family of synthetic hydrophilic polymers includes polyacrylic acid, polyvinyl pyrrolidone, polyvinyl alcohol, polyacrylamide, poly hydroxybutyl acrylate, and poly 2-hydroxyethyl methacrylate. In this family of synthetic hydrophilic polymers, poly 2-hydroxyethyl methacrylate and poly hydroxybutyl acrylate are water insoluble polymers prepared from a water soluble monomer. The other polymers require crosslinking to form a water insoluble polymer.
2-Hydroxyethyl methacrylate polymers are of interest because of their biocompatibility as evidenced by excellent performance in animal implant studies. The extensive use of 2-hydroxyethyl methacrylate polymers for contact lenses for the eyes illustrates the non irritating nature of the polymers.
Other than commercial use in contact lenses, 2-hydroxyethyl methacrylate polymers have had limited commercial success, used at low percentages only, because of the nature of the monomer. Industrial grade 2-hydroxyethyl methacrylate monomer contains a small amount of crosslinker impurity which can cause gel formation during solvent polymerization. The preparation of 2-hydroxyethyl methacrylate polymer, therefore, generally requires the use of very pure and expensive monomer or a very extensive and expensive polymerization process.
U.S. Pat. No. 2,976,576 describes the use of poly 2-hydroxyethyl methacrylate resin for contact lenses and body implants.
U.S. Pat. No. 3,220,960 describes the use of poly 2-hydroxyethyl methacrylate resin for contact lenses and body implants.
U.S. Pat. No. 3,567,760 describes the preparation of 2-hydroxyethyl methacrylate copolymers in methanol that are water soluble salts for entrapping drugs, pesticides, flavoring agents, and fragrances.
U.S. Pat. No. 3,963,685 describes the preparation of methanol soluble poly 2-hydroxyethyl methacrylate for wound care dressings using high purity 2-hydroxyethyl methacrylate monomer having not over 0.035 weight percent of alkylene glycol dimethacrylate impurities.
EP 024164A1 describes the preparation of methanol soluble poly 2-hydroxyethyl methacrylate using high purity 2-hydroxyethyl methacrylate monomer.
Polymer International, vol. 36 no. 4, pp.303-308 (April 1995), describes the preparation of dimethylformamide soluble poly 2-hydroxyethyl methacrylate using a chain transfer agent to prevent gellation.
U.S. Pat. No. 4,303,066 describes the use of a plasticized poly 2-hydroxyethyl methacrylate resin prepared from high purity monomer as a non-tacky synthetic film for skin burns, with shortened forming time by adding water to the mixture.
U.S. Pat. No. 4,593,053 describes the use of a plasticized polyvinyl pyrrolidone as a hydrophilic medical type pressure sensitive adhesive for biomedical electrodes and transdermal devices.
WO 92/11825 describes the use of plasticized poly 2-hydroxyethyl methacrylate resin as a hydrophilic medical type pressure sensitive adhesive for a medical device.
U.S. Pat. No. 5,225,473 describes the use of a UV cured plasticized polyvinyl pyrrolidone as a hydrophilic medical type pressure sensitive adhesive for biomedical electrodes and transdermal devices.
U.S. Pat. No. 5,206,071 describes acrylic graft copolymers and water soluble polymers.
EP 0716929A1 describes acrylic graft copolymers and water soluble polymers.
DE 19516111A1 describes water soluble copolymers with crosslinkers.
U.S. Pat. No. 3,813,695 discloses a rubber or latex surgical glove that is laminated with an internal plastic lining of a hydrophilic material.
U.S. Pat. No. 4,575,476 discloses a dipped rubber glove having an outer rubber layer and a lubricating layer formed of a hydrogel polymer bonded thereto to provide a skin-contacting surface of the glove.
In general, the present invention is directed to providing a cost-effective method for the preparation of hydrophilic homopolymers and copolymers with utility as films, coatings, pressure sensitive adhesives, and compositions suitable for topical application to the skin.
BRIEF SUMMARY OF THE INVENTION
A method is provided for the preparation of gel-free poly 2-hydroxyethyl methacrylate substantially in the absence of a chain transfer agent, comprising introducing monomeric 2-hydroxyethyl methacrylate containing ethylene glycol dimethacrylate impurities in the range of no more than about 0.05-0.1% by weight of the monomer, into alcohol, polymerizing the 2-hydroxyethyl methacrylate to form a polymerization mixture, and optionally removing the alcohol. The alcohol is preferably selected from one of methanol and ethanol. Hydrophilic pressure sensitive adhesives are provided by adding polyethylene glycol to the polymerization mixture prior to removing the alcohol. Flexible hydrophilic coatings also are provided by adding glycerin to the polymerization mixture prior to removing the alcohol by drying.
A method is also provided for the preparation of a gel free hydrophilic polymer substantially in the absence of a chain transfer agent comprising a copolymer of 2-hydroxyethyl methacrylate and 4-hydroxybutyl acrylate, including introducing monomeric 2-hydroxyethyl methacrylate containing no more than about 0.05-0.1% by weight of ethylene glycol dimethacrylate into an alcohol solution with 4-hydroxybutyl acrylate, polymerizing the 2-hydroxyethyl methacrylate and 4-hydroxybutyl acrylate to form a polymerization mixture, and removing the alcohol. The alcohol is selected from one of methanol and ethanol, with ethanol being preferred.
In another embodiment, the monomeric 2-hydroxyethyl methacrylate contains no more than about 3% by weight alkylene glycol methacrylate impurities, wherein the alkylene glycol methacrylate impurities are selected from the group consisting of ethylene glycol dimethacrylate, diethylene glycol monomethacrylate, methacrylic acid and mixtures thereof.
A method is also provided for the preparation of a gel free hydrophilic copolymer of 2-hydroxyethyl methacrylate and 4-hydroxybutyl acrylate substantially in the absence of a chain transfer agent comprising introducing monomeric 2-hydroxyethyl methacrylate containing no more than about 0.05-0.1% by weight of ethylene glycol dimethacrylate into a solution of water and alcohol with 4-hydroxybutyl acrylate, and polymerizing the 2-hydroxyethyl methacrylate and 4-hydroxybutyl acrylate to form a polymerization mixture.
In a preferred embodiment, the alcohol is selected from one of methanol and ethanol, with ethanol being preferred.
In another embodiment, the monomeric 2-hydroxyethyl methacrylate contains no more than about 3% by weight alkylene glycol methacrylate impurities, wherein the alkylene glycol methacrylate impurities are selected from the group consisting of ethylene glycol dimethacrylate, diethylene glycol monomethacrylate, methacrylic acid and mixtures thereof.
In another embodiment, the copolymer of 2-hydroxyethyl methacrylate and 4-hydroxybutyl acrylate is blended with a polyalkylene glycol, such as polyethylene glycol, to form a pressure sensitive adhesive.
The invention also provides a method for the preparation of a gel-free homopolymer of 4-hydroxybutyl acrylate substantially in the absence of a chain transfer agent comprising introducing monomeric 4-hydroxybutyl acrylate into alcohol, and polymerizing the 4-hydroxybutyl acrylate to form a polymerization mixture.
In another embodiment, the present invention provides a method for the preparation of a gel free hydrophilic homopolymer of 4-hydroxybutyl acrylate substantially in the absence of a chain transfer agent comprising introducing monomeric 4-hydroxybutyl acrylate into a solution of water and alcohol, and polymerizing the 4-hydroxybutyl acrylate.
In a preferred embodiment, the alcohol is selected from one of methanol and ethanol, with ethanol being preferred.
In another embodiment, the present invention provides a method for the preparation of

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