Patent US4224427A successfully refreshed from Google Patents.
US4224427A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for preparing hydrogels as spherical beads of large size
Assignee: BASF Corp
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Filing: 1978-06-01
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Granted: 1980-09-23
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Expires: 1998-06-01
Abstract
Abstract The disclosure describes an improved process for the preparation of uniform, spherical beads of up to 5 mm diameter of a crosslinked, water-insoluble hydrogel by suspension polymerization in a concentrated aqueous salt solution of 95-30% by weight of a monoolefinic water-soluble monomer containing at least 5% of a hydroxy substituted hydrophilic vinyl monomer with 5-70% by weight of a terminal diolefinic macromer crosslinking agent in the presence of water-insoluble, gelatinous, strong water-bonding inorganic metal hydroxides as suspending agents in the absence of excess alkali. The hydrogels have a host of pharmaceutical and industrial uses.
Inventors
- 👤 Karl F. Mueller
- 👤 Sonia J. Heiber
- 👤 Walter L. Plankl
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 12:52
CPC Classifications
C; C08; C08F; C08F290/00; C08F290/02; C08F290/06; A; A61; A61K; A61K9/00; A61K9/14; A61K9/16; A61K9/1605; A61K9/1629; A61K9/1635; A61K9/20; A61K9/2004; A61K9/2022; A61K9/2027; Y; Y10; Y10S; Y10S525/00; Y10S525/92; Y10S525/921; Y10S525/925; Y10S526/00; Y10S526/909; Y10S526/91; Y10S526/93
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
407 words
An improved process for preparing essentially uniform spherical beads of up to 5 mm diameter of a crosslinked, water-insoluble hydrogel by suspension polymerization of (A) 95 to 30% by weight of the hydrogel of a water-soluble monoolefinic monomer or mixture of said water-soluble monomers, and from 0 to 70% by weight based on the total monomer of a water-insoluble monoolefinic monomer or mixture of said water-insoluble monomers, with the proviso that the final hydrogel does not contain over 60% by weight of said water-insoluble monomer components, with (B) 5 to 70% by weight of the hydrogel of a polyolefinic crosslinking macromer of the formula ##STR9## wherein a is 1 or 2, R 1 is a polycondensate chain having a molecular weight from about 200 to about 8,000 which contains hydrocarbon residues connected via ether, ester, amide or urea linkages or is a polysiloxane of molecular weight between 400 and 8,000; R 2 is hydrogen, methyl or --CH 2 COOR 4 ; R 4 is hydrogen or alkyl of 1 to 10 carbon atoms; R 3 is hydrogen or --COOR 4 with the proviso that at least one of R 2 and R 3 is hydrogen; X is an oxygen atom, --COO-- or --CONR 5 ; R 5 is hydrogen or alkyl of 1 to 5 carbon atoms; Y is a direct bond or the radical R 6 --Z 1 --CONH-- R 7 NHCO--Z 2 --; R 6 is linked to X and represents branched or linear alkylene of 1 to 7 carbon atoms; Z 1 is an oxygen atom or --NR 5 --; Z 2 is Z 1 or a sulfur atom; and R 7 is the diradical of an aliphatic, alicyclic or aromatic diisocyanate with the proviso that in case X is oxygen, Y is different from a direct bond and R 2 and R 3 are hydrogen, with a polymerization initiator in a concentrated aqueous inorganic salt solution wherein the improvement comprises carrying out the suspension polymerization with monoolefinic monomers containing at least 5% by weight of the total monomers of a hydroxy substituted hydrophilic vinyl monomer; employing as the crosslinking agent a polyolefinic macromer having a molecular weight from about 400 to about 8,000 and utilizing from 0.01 to 5% by weight, based on the hydrogel, of a suspending agent selected from the water-insoluble, gelatinous, strongly water-bonding, inorganic metal hydroxides and metal hydroxy salts in the absence of excess alkali or free hydroxyl ions.
Claim 2
Dependent Claim
407 words
An improved process for preparing essentially uniform spherical beads of up to 5 mm diameter of a crosslinked, water-insoluble hydrogel by suspension polymerization of (A) 95 to 30% by weight of the hydrogel of a water-soluble monoolefinic monomer or mixture of said water-soluble monomers, and from 0 to 70% by weight based on the total monomer of a water-insoluble monoolefinic monomer or mixture of said water-insoluble monomers, with the proviso that the final hydrogel does not contain over 60% by weight of said water-insoluble monomer components, with (B) 5 to 70% by weight of the hydrogel of a polyolefinic crosslinking macromer of the formula ##STR9## wherein a is 1 or 2, R 1 is a polycondensate chain having a molecular weight from about 200 to about 8,000 which contains hydrocarbon residues connected via ether, ester, amide or urea linkages or is a polysiloxane of molecular weight between 400 and 8,000; R 2 is hydrogen, methyl or --CH 2 COOR 4 ; R 4 is hydrogen or alkyl of 1 to 10 carbon atoms; R 3 is hydrogen or --COOR 4 with the proviso that at least one of R 2 and R 3 is hydrogen; X is an oxygen atom, --COO-- or --CONR 5 ; R 5 is hydrogen or alkyl of 1 to 5 carbon atoms; Y is a direct bond or the radical R 6 --Z 1 --CONH-- R 7 NHCO--Z 2 --; R 6 is linked to X and represents branched or linear alkylene of 1 to 7 carbon atoms; Z 1 is an oxygen atom or --NR 5 --; Z 2 is Z 1 or a sulfur atom; and R 7 is the diradical of an aliphatic, alicyclic or aromatic diisocyanate with the proviso that in case X is oxygen, Y is different from a direct bond and R 2 and R 3 are hydrogen, with a polymerization initiator in a concentrated aqueous inorganic salt solution wherein the improvement comprises carrying out the suspension polymerization with monoolefinic monomers containing at least 5% by weight of the total monomers of a hydroxy substituted hydrophilic vinyl monomer; employing as the crosslinking agent a polyolefinic macromer having a molecular weight from about 400 to about 8,000 and utilizing from 0.01 to 5% by weight, based on the hydrogel, of a suspending agent selected from the water-insoluble, gelatinous, strongly water-bonding, inorganic metal hydroxides and metal hydroxy salts in the absence of excess alkali or free hydroxyl ions.
Claim 3
Dependent Claim
16 words
A process according to claim 1 wherein the water-soluble monomer is a monolefinic, monocyclic, azacyclic compound.
Claim 4
Dependent Claim
29 words
A process according to claim 1 wherein the water-soluble monomer is a hydroxyalkyl ester of acrylic or methacrylic acid in which alkyl is of 2 to 4 carbon atoms.
Claim 5
Dependent Claim
47 words
A process according to claim 1 wherein the water-soluble monomer is an acrylic or methacrylic acid ester derived from an alcohol of the formula HO--C.sub.m H.sub.2m --O--(CH.sub.2 CH.sub.2 O).sub.n --R where R is hydrogen or methyl, m is 2 to 5 and n is 1 to 20.
Claim 6
Dependent Claim
36 words
A process according to claim 1 wherein the water-soluble monomer is an N-substituted amide or imide of acrylic or methacrylic acid in which the N-substituent is hydroxyalkyl, wherein alkyl is of 2 to 4 carbon atoms.
Claim 7
Dependent Claim
28 words
A process according to claim 1 wherein the water-soluble monomer is a hydroxyalkyl diester of maleic or fumaric acid, wherein alkyl is of 2 to 4 carbon atoms.
Claim 8
Dependent Claim
25 words
A process according to claim 1 wherein the water-soluble monomer is a hydroxyalkyl vinyl ether, where the alkyl is of 2 to 4 carbon atoms.
Claim 9
Dependent Claim
39 words
A process according to claim 1 wherein the 0 to 15% by weight of the total monomer is selected from the group consisting of acrylic acid, methacrylic acid, 2-vinyl pyridine, 4-vinylpyridine, 2-(dimethylamino)ethyl methacrylate, N-[2-(dimethylamino)ethyl] methacrylamide and sodium styrene sulfonate.
Claim 10
Dependent Claim
30 words
A process according to claim 1 wherein the water-soluble monomer is 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate, 3-hydroxypropyl methacrylate, 2,3-dihydroxypropyl acrylate, 2,3-dihydroxypropyl methacrylate, N-vinyl-2-pyrrolidone or N-methylolacrylamide.
Claim 11
Dependent Claim
13 words
A process according to claim 9 wherein the water-soluble monomer is 2-hydroxyethyl methacrylate.
Claim 12
Dependent Claim
12 words
A process according to claim 9 wherein the water-soluble monomer is N-vinyl-2-pyrrolidone.
Claim 13
Dependent Claim
25 words
A process according to claim 1 wherein the water-insoluble monomer is an alkyl acrylate or methacrylate where alkyl is of 1 to 18 carbon atoms.
Claim 14
Dependent Claim
24 words
A process according to claim 1 wherein the water-insoluble monomer is a vinyl ester of a carboxylic acid having 2 to 7 carbon atoms.
Claim 15
Dependent Claim
24 words
A process according to claim 1 wherein the water-insoluble monomer is a vinyl alkyl ether, wherein alkyl is of 1 to 5 carbon atoms.
Claim 16
Dependent Claim
14 words
A process according to claim 1 wherein the insoluble monomer is acrylonitrile or styrene.
Claim 17
Dependent Claim
29 words
A process according to claim 1 wherein R 1 is a poly(ethylene oxide), poly(propylene oxide) or poly(tetramethylene oxide) chain with a molecular weight of about 600 to about 4,000.
Claim 18
Dependent Claim
33 words
A process according to claim 1 wherein, R 1 is a chain obtained by the condensation reaction of an aliphatic, alicyclic or aromatic dicarboxylic acid or diisocyanate with an aliphatic diol or diamine.
Claim 19
Dependent Claim
56 words
A process according to claim 1 wherein R 1 is a polysiloxane chain of the structure ##STR10## wherein R 8 is a branched or linear alkylene of 1 to 7 carbon atoms or ##STR11## n is 1 to 20, R 9 is hydrogen or methyl, x is 3 to 120 and y is 2 to 3.
Claim 20
Dependent Claim
53 words
A process according to claim 1 wherein the macromer is a reaction product of a poly(tetramethylene oxide) glycol with a molecular weight of about 600 to about 4,000, first terminated with tolylene-2,4-diisocyanate or isophorone diisocyanate, and then endcapped with a hydroxyalkyl acrylate or methacrylate, where alkyl is of 2 to 4 carbon atoms.
Claim 21
Dependent Claim
28 words
A process according to claim 19 wherein the poly(tetramethylene oxide) glycol has a molecular weight of about 1,500 to about 3,000 and the hydroxyalkyl methacrylate is 2-hydroxyethyl methacrylate.
Claim 22
Dependent Claim
54 words
A process according to claim 1 wherein the suspending agent is an insoluble, gelatinous metal hydroxide or metal hydroxide salt selected from the group consisting of the hydroxides or hydroxide salts of magnesium, aluminum, zirconium, iron, nickel, chromium, zinc, lead, calcium, cobalt, copper, tin, gallium, manganese, strontium, barium, uranium, titanium, lanthanum, thorium and cerium.
Claim 23
Dependent Claim
22 words
A process according to claim 21 wherein the suspending agent is magnesium hydroxide, aluminum hydroxide, magnesium hydroxy salt or aluminum hydroxy salt.
Claim 24
Dependent Claim
25 words
A process according to claim 1 wherein the inorganic salt is dissolved in water at a concentration of about 5 to about 25% by weight.
Claim 25
Dependent Claim
24 words
A process according to claim 1 wherein the inorganic salt is selected from the chlorides and sulfates of the alkali and alkaline earth metals.
Claim 26
Dependent Claim
16 words
A process according to claim 24 wherein the inorganic salt is sodium chloride or sodium sulfate.
Claim 27
Dependent Claim
30 words
A process according to claim 1 wherein from 0.01 to 1% by weight based on monomer of a polymerization catalyst selected from the organic peroxides and azo initiators is used.
References Cited (Backward Citations)
US2801992A
Cited
US3509234A
Cited
US3557061A
Cited
US3716505A
Cited
US3641199A
Cited
JPS4939691A
Cited
US3829531A
Cited
US4034017A
Cited
US3996308A
Cited
US4041104A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-09-23 | 1984-03-24 | 1984-09-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-09-23 | 1988-03-24 | 1988-09-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-09-23 | 1992-03-24 | 1992-09-23 | $7700.00 | Window Closed / Lapsed |