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US4071508A
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Anionic hydrogels based on hydroxyalkyl acrylates and methacrylates
Assignee: Plastomedical Sciences Inc
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Filing: 1975-02-11
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Granted: 1978-01-31
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Expires: 1995-02-11
Abstract
Abstract Novel anionic hydrogels, containing acidic groups in their molecular structure, and processes for their preparation are described. These novel hydrogels are stable three-dimensional polymer networks, having good water permeability and mechanical properties, and are obtained by simultaneous polymerization and cross-linking, in the presence of a polymerization catalyst, such as an organic peroxide, azobisisobutyronitrile or other free radical polymerization catalyst, of a mixture of (a) hydroxyalkyl acrylate or methacrylate, (b) a polymerizable acidic monomer containing a sulfonic acid, sulfate or phosphate group in its molecular structure, such as sulfo-ethyl acrylate or methacrylate or a sulfate or phosphate derivative of a hydroxyalkyl- acrylate or methacrylate, and (c) a cross-linking agent, such as a glycol diacrylate or dimethacrylate; if desired there may also be present (d) one or more additional monomers, usually an acryloid monomer such as an alkyl acrylate or methacrylate, acrylamides etc. (although other monomers such as vinyl acetate, styrene, etc. may also be used) which is copolymerizable with (a), (b) and (c). The thus obtained anionic hydrogels are useful for combining, by reaction or complexing, with materials having an opposite charge; such as basic or cationic agricultural chemicals (insecticides, herbicides, fungicides, plant growth regulators, etc.), germicides, pharmaceuticals, cosmetics, hormones, enzymes, flavors, fragrances, antiperspirants, metals and the like, both to recover such basic or cationic materials from an aqueous medium and for purifying water containing them, and also for the preparation of a complex or other combination of the anionic hydrogel with such materials which may be useful per se or from which the complexed or combined basic or cationic material may be slowly or controllably released.
Inventors
- 👤 Robert Steckler
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 19:26
CPC Classifications
C; C08; C08F; C08F220/00; C08F220/02; C08F220/10; C08F220/20
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
453 words
The anionic, polymeric hydrogel produced by simultaneous polymerization and cross-linking in the presence of a free radical polymerization catalyst in an amount of from about 0.05 to about 4 weight percent, based on the total weight of monomers, and at a temperature of from about 20° C. to about 125° C., of a mixture consisting essentially of the following monomers: A. about 40 to about 95 weight percent, based on the total weight of monomers of an acrylic monomer selected from the group consisting of glyceryl monoacrylates and monomethacrylates and acrylic monomers having the formula: ##STR12## wherein: R and R' each represents hydrogen or lower alkyl of 1 to about 6 carbon atoms; N represents an interger of from 1 to about 50; B. about 50 to about 0.05 weight percent, based on the total weight of monomers, of a monoethylenically unsaturated anionic monomer, capable of copolymerizing with (A), and which contains in its molecular structure a sulfonic acid group and is selected from the group consisting of acrylamido aryl sulfonic acids, acrylamido alkyl sulfonic acids, glycidyl acrylate sulfonic acid, glycidyl methacrylate sulfonic acid, and esters of α-methylene carboxylic acids with hydroxysulfonic acids which esters have the formula: R"--COO--Q--SO.sub.3 M, wherein R" represents a member of the group consisting of vinyl and α substituted vinyl, Q represents a divalent hydrocarbon radical having its valence bonds on different carbon atoms, and M is a cation, selected from the group consisting of hydrogen, ammonium, amino, alkali metal and alkaline earth metal; c. about 0.2 to about 12 weight percent, based on the total weight of monomers, of a polymerizable cross-linking agent, capable of copolymerizing with (a) and (b) and having the formula: ##STR13## wherein R represents a member of the group consisting of hydrogen and alkyl of from 1 to about 4 carbon atoms; A represents alkylene of from 2 to about 10 carbon atoms or a polyglycol ether group of the formula: ##STR14## in which; R' represents a member of the group consisting hydrogen and alkyl of 1 to 2 carbon atoms; N represents an integer of from 1 to about 20; d. from 0 to about 50 weight percent, based on the total weight of monomers, of other monoethylenically unsaturated monomers capable of copolymerizing with (A), (B) and (C) and selected from the group consisting of: Acrylamides, Methacrylamides, acrylonitrile, alkyl acrylates, alkyl methacrylates, N-vinyl lactams, N-vinyl succinimide, N-vinyl diglycoylimide, N-vinyl glutarimide, N-vinyl-3-morpholinone, N-vinyl-5-methyl-3-morpholinone and N-vinyl imidazole; Provided that (A) ≧ (D) and (A) + (D) = about 40 to about 95 weight percent; and when an N-vinyl lactam, N-vinyl succinimide, N-vinyl diglycoylimide, N-vinyl glutarimide, N-vinyl-3-morpholinone, N-vinyl-5-methyl-3-morpholinone or N-vinyl imidazole is used it is present in an amount of less than 20 weight percent.
Claim 2
Dependent Claim
453 words
The anionic, polymeric hydrogel produced by simultaneous polymerization and cross-linking in the presence of a free radical polymerization catalyst in an amount of from about 0.05 to about 4 weight percent, based on the total weight of monomers, and at a temperature of from about 20° C. to about 125° C., of a mixture consisting essentially of the following monomers: A. about 40 to about 95 weight percent, based on the total weight of monomers of an acrylic monomer selected from the group consisting of glyceryl monoacrylates and monomethacrylates and acrylic monomers having the formula: ##STR12## wherein: R and R' each represents hydrogen or lower alkyl of 1 to about 6 carbon atoms; N represents an interger of from 1 to about 50; B. about 50 to about 0.05 weight percent, based on the total weight of monomers, of a monoethylenically unsaturated anionic monomer, capable of copolymerizing with (A), and which contains in its molecular structure a sulfonic acid group and is selected from the group consisting of acrylamido aryl sulfonic acids, acrylamido alkyl sulfonic acids, glycidyl acrylate sulfonic acid, glycidyl methacrylate sulfonic acid, and esters of α-methylene carboxylic acids with hydroxysulfonic acids which esters have the formula: R"--COO--Q--SO.sub.3 M, wherein R" represents a member of the group consisting of vinyl and α substituted vinyl, Q represents a divalent hydrocarbon radical having its valence bonds on different carbon atoms, and M is a cation, selected from the group consisting of hydrogen, ammonium, amino, alkali metal and alkaline earth metal; c. about 0.2 to about 12 weight percent, based on the total weight of monomers, of a polymerizable cross-linking agent, capable of copolymerizing with (a) and (b) and having the formula: ##STR13## wherein R represents a member of the group consisting of hydrogen and alkyl of from 1 to about 4 carbon atoms; A represents alkylene of from 2 to about 10 carbon atoms or a polyglycol ether group of the formula: ##STR14## in which; R' represents a member of the group consisting hydrogen and alkyl of 1 to 2 carbon atoms; N represents an integer of from 1 to about 20; d. from 0 to about 50 weight percent, based on the total weight of monomers, of other monoethylenically unsaturated monomers capable of copolymerizing with (A), (B) and (C) and selected from the group consisting of: Acrylamides, Methacrylamides, acrylonitrile, alkyl acrylates, alkyl methacrylates, N-vinyl lactams, N-vinyl succinimide, N-vinyl diglycoylimide, N-vinyl glutarimide, N-vinyl-3-morpholinone, N-vinyl-5-methyl-3-morpholinone and N-vinyl imidazole; Provided that (A) ≧ (D) and (A) + (D) = about 40 to about 95 weight percent; and when an N-vinyl lactam, N-vinyl succinimide, N-vinyl diglycoylimide, N-vinyl glutarimide, N-vinyl-3-morpholinone, N-vinyl-5-methyl-3-morpholinone or N-vinyl imidazole is used it is present in an amount of less than 20 weight percent.
Claim 3
Dependent Claim
22 words
The anionic, polymeric hydrogel as defined in claim 1, wherein the acrylic monomer specified as (a) is a hydroxyalkyl acrylate or methacrylate.
Claim 4
Dependent Claim
19 words
The anionic, polymeric hydrogel as defined in claim 2, wherein the acrylic monomer specified as (a) is 2-hydroxyethyl methacrylate.
Claim 5
Dependent Claim
26 words
The anionic, polymeric hydrogel as defined in claim 1, wherein the polymerizable ethylenically unsaturated monomer containing an acid group specified as (b) is Beta sulfoethyl methacrylate.
Claim 6
Dependent Claim
26 words
The anionic, polymeric hydrogel as defined in claim 1, wherein the polymerizable ethylenically unsaturated monomer containing an acid group specified as (b) is glycidyl methacrylate sulfonate.
Claim 7
Dependent Claim
25 words
The anionic, polymeric hydrogel as defined in claim 1, wherein the polymerizable ethylenically unsaturated monomer containing an acid group specified as (b) is 2-methacrylamide-2-methylpropane-1-sulfonic acid.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-01-30 | 1981-08-01 | 1982-01-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-01-30 | 1985-08-01 | 1986-01-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-01-30 | 1989-08-01 | 1990-01-31 | $7700.00 | Window Closed / Lapsed |