Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Polymers from only ethylenic monomers or processes of...
Reexamination Certificate
2002-04-26
2004-06-01
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, C526S312000, C526S317100, C526S318400, C526S318420, C526S319000, C526S325000, C526S328500, C526S329200
Reexamination Certificate
active
06743880
ABSTRACT:
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 having ethylene glycol dimethacrylate impurities less than 0.035 weight percent, based on the weight of the 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.
BRIEF SUMMARY OF THE INVENTION
In general, the present invention relates to providing a cost-effective method for the preparation of gel-free, hydrophilic polymers, which have utility in topical skin applications, as cosmetic compositions, dermatological compositions, and as skin friendly coatings; as pressure sensitive adhesives; and as precursors for hydrogels.
The present invention provides a method for the preparation of a water insoluble, gel-free copolymer of 2-hydroxyethyl methacrylate and acrylic acid or methacrylic acid substantially in the absence of a chain transfer agent comprising: introducing monomeric 2-hydroxyethyl methacrylate containing ethylene glycol dimethacrylate impurities up to about 0.15% by weight, based on the weight of the monomer, and at least one of acrylic acid or methacrylic acid into a solution of water and alcohol; and copolymerizing the 2-hydroxyethyl methacrylate and the at least one of acrylic acid or methacrylic acid to form a polymerization mixture.
In one embodiment, the monomeric 2-hydroxyethyl methacrylate useful in the inventive method may contain ethylene glycol dimethacrylate impurity in the range of about 0.05% to about 0.1% by weight of the monomer. In another embodiment, the inventive method uses a monomeric 2-hydroxyethyl methacrylate that contains impurities in a total amount of no more than about 3% by weight of the monomer, where the impurities include ethylene glycol dimethacrylate, diethylene glycol monomethacrylate, methacrylic acid and mixtures of these impurities.
Hydrophilic pressure sensitive adhesives are provided by adding polyalkylene glycol to the polymerization mixture. Flexible skin coatings are provided by adding a flexiblizing agent to the polymerization mixture.
The present invention also provides a method for the preparation of a hydrophilic, gel-free, water insoluble copolymer of 2-hydroxyethyl methacrylate, 4-hydroxybutyl acrylate and at least one of acrylic acid or methacrylic acid substantially in the absence of a chain transfer agent comprising: introducing monomeric 2-hydroxyethyl methacrylate, monomeric 4-hydroxybutyl acrylate and at least one of acrylic acid or methacrylic acid into a solution of water and alcohol, wherein the monomeric 2-hydroxyethyl methacrylate contains ethylene glycol dimethacrylate impurities up to about 0.15% by weight, based on the weight of the monomer; and copolymerizing the monomeric 2-hydroxyethyl methacrylate, monomeric 4-hydroxybutyl acrylate and at least one of acrylic acid or methacrylic acid to form a polymerization mixture.
In another embodiment, the monomeric 2-hydroxyethyl methacrylate useful in the inventive method contain ethylene glycol dimethacrylate impurity in the range of about 0.05% to about 0.1% by weight of the monomer. In another embodiment, the inventive method uses a monomeric 2-hydroxyethyl methacrylate that contains impurities in a total amount of no more than about 3% by weight of the monomer, where the impurities include ethylene glycol dimethacrylate, diethylene glycol monomethacrylate, methacrylic acid and mixtures of these impurities.
Hydrophilic pressure sensitive adhesives are provided by adding polyalkylene glycol to the polymerization mixture. Flexible skin coatings are provided by adding a flexiblizing agent to the polymerization mixture.
The present invention also provides a method for the preparation of a substantially monoalcohol-free, gel-free, water insoluble, 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 ethylene glycol dimethacrylate impurities up to about 0.15% by weight, based on the weight of the monomer, and monomeric 4-hydroxybutyl acrylate into a solution of water and a monoalcohol; copolymerizing the monomeric 2-hydroxyethyl methacrylate and the 4-hydroxybutyl acrylate to form a polymerization mixture; leaching the copolymer of 2-hydroxyethyl methacrylate and 4-hydroxybutyl acrylate to substantially remove residual monomer; and substantially replacing the monoalcohol with a polyhydric alcohol.
In another embodiment, the monomeric 2-hydroxyethyl methacrylate that is useful in the in
Avery Denison Corporation
Renner Kenner Greive Bobak Taylor & Weber
Zalukaeva Tatyana
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