US4163092A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Cationic hydrogels based on hydroxyalkyl acrylates and methacrylates
Assignee: Plastomedical Sciences Inc
•
Filing: 1977-08-18
•
Granted: 1979-07-31
•
Expires: 1997-08-18
Abstract
Abstract Novel cationic hydrogels, containing basic (cationic) groups in their molecular structure, and processes for their preparation are described. These novel hydrogels are three-dimensional polymer networks, having good water permeability and mechanical properties, and are obtained by simultaneous polymerization and crosslinking, 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 cationic monomer -- usually an ester of acrylic or methacrylic acid with an amino alcohol, the terminal amino group of which may be quaternized, such as dimethylaminoethyl methacrylate or acrylate and the quaternized derivatives thereof, and (c) a cross-linking agent, such as glycol diacrylate or dimethacrylate; if desired there may also be present (d) one or more additional monomers, usually an acrylic 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 cationic hydrogels are useful for combining, by reaction or complexing, with materials having an opposite charge; such as acidic or anionic 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 acidic or anionic materials from an aqueous medium and for purifying water containing them, and also for the preparation of a complex or other combination of the cationic hydrogel with such materials which may be useful per se or from which the complexed or combined acidic or anionic material may be slowly or controllably released.
Inventors
- 👤 Robert Steckler
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 14:29
CPC Classifications
C; C08; C08F; C08F220/00; C08F220/02; C08F220/10; C08F220/34; C08F220/20
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
414 words
The cationic, polymeric hydrogel produced by the process which comprises simultaneously polymerizing 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., 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: ##STR17## wherein: R and R' each represents hydrogen or lower alkyl of 1 to about 6 carbon atoms; n represents and integer 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 cationic monomer, capable of copolymerizing with (a), and which is a quaternary ammonium compound having the formula: ##STR18## wherein: R represents H or CH 3 ; R 2 , r 3 and R 4 , each of which may be the same or different, each represents alkyl, phenyl or aralkyl; and Y represents an anion forming the anionic portion of a quaternary ammonium group; (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: ##STR19## 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 carbons or a polyglycol ether group of the formula: ##STR20## in which R' represents a member of the group consisting of hydrogen and alkyl of 1 to 2 carbon atoms; and n represents an integer of from 1 to about 20; and (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, 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 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
414 words
The cationic, polymeric hydrogel produced by the process which comprises simultaneously polymerizing 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., 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: ##STR17## wherein: R and R' each represents hydrogen or lower alkyl of 1 to about 6 carbon atoms; n represents and integer 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 cationic monomer, capable of copolymerizing with (a), and which is a quaternary ammonium compound having the formula: ##STR18## wherein: R represents H or CH 3 ; R 2 , r 3 and R 4 , each of which may be the same or different, each represents alkyl, phenyl or aralkyl; and Y represents an anion forming the anionic portion of a quaternary ammonium group; (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: ##STR19## 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 carbons or a polyglycol ether group of the formula: ##STR20## in which R' represents a member of the group consisting of hydrogen and alkyl of 1 to 2 carbon atoms; and n represents an integer of from 1 to about 20; and (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, 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 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 cationic, 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 cationic, polymeric hydrogel as defined in claim 1, wherein the acrylic monomer specified as (a) is 2-hydroxyethyl methacrylate.
Claim 5
Dependent Claim
370 words
The cationic, polymeric hydrogel produced by the process which comprises simultaneously polymerizing 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., 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 monomers selected from the group consisting of glyceryl monoacrylates and and monomethacrylates and acrylic monomers having the formula: ##STR21## wherein: R and R' each represent hydrogen or lower alkyl of 1 to about 6 carbon atoms; n represents an integer 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 cationic monomer, capable of copolymerizing with (a), and which is a quaternary ammonium compound having the formula: ##STR22## in which R represents H or CH 3 (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: ##STR23## 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 carbons or a polyglycol ether group of the formula: ##STR24## in which R' represents a member of the group consisting hydrogen and alkyl of 1 to 2 carbon atoms; and n represents an integer of from 1 to about 20; and (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, alkyl acrylates, alkyl methacrylates, N-vinyl lactams, N-vinyl succinimide, N-vinyl diglycoylimide, N-vinyl glutaramide, 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 6
Dependent Claim
370 words
The cationic, polymeric hydrogel produced by the process which comprises simultaneously polymerizing 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., 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 monomers selected from the group consisting of glyceryl monoacrylates and and monomethacrylates and acrylic monomers having the formula: ##STR21## wherein: R and R' each represent hydrogen or lower alkyl of 1 to about 6 carbon atoms; n represents an integer 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 cationic monomer, capable of copolymerizing with (a), and which is a quaternary ammonium compound having the formula: ##STR22## in which R represents H or CH 3 (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: ##STR23## 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 carbons or a polyglycol ether group of the formula: ##STR24## in which R' represents a member of the group consisting hydrogen and alkyl of 1 to 2 carbon atoms; and n represents an integer of from 1 to about 20; and (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, alkyl acrylates, alkyl methacrylates, N-vinyl lactams, N-vinyl succinimide, N-vinyl diglycoylimide, N-vinyl glutaramide, 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 7
Dependent Claim
22 words
The cationic, polymeric hydrogel as defined in claim 4, wherein the acrylic monomer specified as (a) is a hydroxyalkyl acrylate or methacrylate.
Claim 8
Dependent Claim
19 words
The cationic, polymeric hydrogel as defined in claim 4, wherein the acrylic monomer specified as (a) is 2-hydroxyethyl methacrylate.
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) | 1982-07-30 | 1983-01-29 | 1983-07-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-07-30 | 1987-01-29 | 1987-07-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-07-30 | 1991-01-29 | 1991-07-31 | $7700.00 | Window Closed / Lapsed |