US5206341A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Polymers from hydroxy acids and polycarboxylic acids
Assignee: Surmodics MD LLC
•
Filing: 1991-11-21
•
Granted: 1993-04-27
•
Expires: 2011-11-21
Abstract
Abstract Copolymers from a hydroxy acid and a polycarboxylic component, method of preparation thereof, and use thereof are provided.
Inventors
- 👤 Augusto C. Ibay
- 👤 Linwood P. Tenney
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 21:17
CPC Classifications
C; C08; C08G; C08G63/00; C08G63/02; C08G63/60; A; A61; A61L; A61L17/00; A61L17/06; A61L17/10; A61L17/12; A61L26/00; A61L26/0009; A61L26/0019; A61L27/00; A61L27/14; A61L27/18; A61L29/00; A61L29/04; A61L29/06; A61L31/00; A61L31/04; A61L31/06; D; D01; D01F; D01F6/00; D01F6/58; D01F6/62; D01F6/625; D01F6/78; D01F6/84
Claims Analysis
Total Claims: 73
Claim 1
Independent Claim
130 words
A copolymer from a hydroxyalkanoic acid containing 2 to 22 carbon atoms and polycarboxylic component selected from the group consisting of non-polymeric polycarboxylic acid containing 2 to 22 carbon atoms, activated derivative thereof, water soluble homo-or copolymer of ethylenically unsaturated carboxylic acid, activated derivative thereof, and mixtures thereof, wherein the amount of said hydroxyalkanoic acid is about 99.95 mole % to about 90 mole % based upon the total moles of said hydroxyalkanoic acid and the reactive carboxylic moieties of the polycarboxylic component; and correspondingly said reactive carboxylic moieties of said polycarboxylic component is about 0.05 mole % to about 10 mole % based upon the total of said hydroxyalkanoic acid and said reactive moieties of polycarboxylic component. The end groups of said polymer are at least 90% carboxyl groups.
Claim 2
Dependent Claim
130 words
A copolymer from a hydroxyalkanoic acid containing 2 to 22 carbon atoms and polycarboxylic component selected from the group consisting of non-polymeric polycarboxylic acid containing 2 to 22 carbon atoms, activated derivative thereof, water soluble homo-or copolymer of ethylenically unsaturated carboxylic acid, activated derivative thereof, and mixtures thereof, wherein the amount of said hydroxyalkanoic acid is about 99.95 mole % to about 90 mole % based upon the total moles of said hydroxyalkanoic acid and the reactive carboxylic moieties of the polycarboxylic component; and correspondingly said reactive carboxylic moieties of said polycarboxylic component is about 0.05 mole % to about 10 mole % based upon the total of said hydroxyalkanoic acid and said reactive moieties of polycarboxylic component. The end groups of said polymer are at least 90% carboxyl groups.
Claim 3
Dependent Claim
36 words
The copolymer of claim 1 wherein said hydroxy- carboxylic acid consists essentially of an acid selected from the group consisting of lactic acid, glycolic acid; β-hydroxybutyric acid; α-hydroxybutyric acid; δ-hydroxyvaleric acid; ε-hydroxycaproic acid and mixtures thereof.
Claim 4
Dependent Claim
18 words
The copolymer of claim 1 wherein said polycarboxylic acid is non-polymeric and contains 2 to 22 carbon atoms.
Claim 5
Dependent Claim
50 words
The copolymer of claim 1 wherein said polycarboxylic component consists essentially of a polycarboxylic acid selected from the group consisting of trimesic acid, succinic acid, fumaric acid, maleic acid, brassylic acid, adipic acid, ethylenediaminetetraacetic acid, nitrilotriacetic acid, citric acid, trimellitic acid, terephthalic acid, isophthalic acid, pyromellitic acid, and mixtures thereof.
Claim 6
Dependent Claim
41 words
The copolymer of claim 1 wherein said amount of said hydroxycarboxylic acid is about 99 to about 99.9 mole % and correspondingly said amount of said reactive carboxylic moieties of the polycarboxylic component is about 1 to about 0.1 mole %.
Claim 7
Dependent Claim
24 words
The copolymer of claim 1 wherein said hydroxy carboxylic acid contains only one primary reactive hydroxy group or only one secondary reactive hydroxyl group.
Claim 8
Dependent Claim
65 words
The copolymer of claim 1 wherein said polycarboxylic component is selected from the group consisting of homo- or co-polymers of ethylenically unsaturated carboxylic acid or of an anhydride thereof, or of an ester thereof; and activated derivative of a non-polymeric polycarboxylic acid or of a polymeric polycarboxylic acid selected from the group consisting of esters, anhydrides, acyl halides, trialkylsilyl esters, acyl imidazoles, ketenes and 0-acylureas.
Claim 9
Dependent Claim
21 words
The copolymer of claim 1 wherein said activated derivative consists essentially of an alkyl ester having 1 to 6 carbon atoms.
Claim 10
Dependent Claim
35 words
The copolymer of claim 1 wherein said anhydride derivative is selected from the group consisting of polypyromellitic anhydride, polyterephthalic anhydride phthalic anhydride, succinic anhydride, maleic anhydride, adipic anhydride, glutaric anhydride, polyisophthalic anhydride, and mixtures thereof.
Claim 11
Dependent Claim
14 words
The copolymer of claim 1 wherein said hydroxycarboxylic acid consists essentially of lactic acid.
Claim 12
Dependent Claim
17 words
The copolymer of claim 1 wherein the average number molecular weight is about 2,000 to about 10,000.
Claim 13
Dependent Claim
17 words
The copolymer of claim 1 wherein the average number molecular weight is about 3,000 to about 6,000.
Claim 14
Dependent Claim
98 words
A copolymer from a hydroxycarboxylic acid and polycarboxylic component selected from the group consisting of polycarboxylic acid, activated derivative thereof, and mixtures thereof, wherein the amount of said hydroxycarboxylic acid is about 99.95 mole % to about 90 mole % based upon the total moles of said hydroxycarboxylic acid and the reactive carboxylic moieties of said polycarboxylic component; and correspondingly said reactive carboxylic moieties of said polycarboxylic component is about 0.05 mole % to about 10 mole % based upon the total of said hydroxycarboxylic acid and reactive carboxylic moieties of said polycarboxylic component, and a metallic compound.
Claim 15
Dependent Claim
98 words
A copolymer from a hydroxycarboxylic acid and polycarboxylic component selected from the group consisting of polycarboxylic acid, activated derivative thereof, and mixtures thereof, wherein the amount of said hydroxycarboxylic acid is about 99.95 mole % to about 90 mole % based upon the total moles of said hydroxycarboxylic acid and the reactive carboxylic moieties of said polycarboxylic component; and correspondingly said reactive carboxylic moieties of said polycarboxylic component is about 0.05 mole % to about 10 mole % based upon the total of said hydroxycarboxylic acid and reactive carboxylic moieties of said polycarboxylic component, and a metallic compound.
Claim 16
Dependent Claim
20 words
The copolymer of claim 13 wherein the metal cation of said metallic compound has a valence of at least two.
Claim 17
Dependent Claim
20 words
The copolymer of claim 14 wherein said metallic compound consists essentially of a zinc or calcium salt or mixture thereof.
Claim 18
Dependent Claim
17 words
The copolymer of claim 13, wherein the average number molecular weight is about 2,000 to about 10,000.
Claim 19
Dependent Claim
71 words
A copolymer from a hydroxycarboxylic acid and polycarboxylic component selected from the group consisting of polycarboxylic acid, activated derivative thereof, and mixtures thereof, wherein the relative amount of said hydroxycarboxylic acid and polycarboxylic component is such that said copolymer has a maximum melting point of about 180° C., an average number molecular weight of about 2,000 to about 10,000, and at least about 90% of the terminal groups being carboxyl groups.
Claim 20
Dependent Claim
71 words
A copolymer from a hydroxycarboxylic acid and polycarboxylic component selected from the group consisting of polycarboxylic acid, activated derivative thereof, and mixtures thereof, wherein the relative amount of said hydroxycarboxylic acid and polycarboxylic component is such that said copolymer has a maximum melting point of about 180° C., an average number molecular weight of about 2,000 to about 10,000, and at least about 90% of the terminal groups being carboxyl groups.
Claim 21
Dependent Claim
31 words
The copolymer of claim 17 wherein said hydroxycarboxylic acid is selected from the group consisting of lactic acid, glycolic acid, β-hydroxybutyric acid, α-hydroxybutyric acid, δ-hydroxyvaleric acid, ε-hydroxycaproic acid and mixtures thereof.
Claim 22
Dependent Claim
52 words
A copolymer from a hydroxycarboxylic acid and a polycarboxylic component selected from the group consisting of polycarboxylic acid, activated derivative thereof, and mixtures thereof, wherein the relative amount of said hydroxycarboxylic acid and polycarboxylic component is such that said copolymer has maximum melting point of about 180° C.; and a metallic compound.
Claim 23
Dependent Claim
52 words
A copolymer from a hydroxycarboxylic acid and a polycarboxylic component selected from the group consisting of polycarboxylic acid, activated derivative thereof, and mixtures thereof, wherein the relative amount of said hydroxycarboxylic acid and polycarboxylic component is such that said copolymer has maximum melting point of about 180° C.; and a metallic compound.
Claim 24
Dependent Claim
20 words
The copolymer of claim 19 wherein the metal cation of said metallic compound has a valence of at least two.
Claim 25
Dependent Claim
20 words
The copolymer of claim 19 wherein said metallic compound consists essentially of a zinc or calcium salt or mixtures thereof.
Claim 26
Dependent Claim
83 words
A process for producing a copolymer which comprises: a) subjecting a hydroxycarboxylic acid to polycondensation, b) adding a polycarboxylic component prior to or during said polycondensation, c) causing said polycarboxylic component and hydroxycarboxylic acid to form a polymer; wherein said polycarboxylic component is selected from the group consisting of polycarboxylic acid, activated derivative thereof, and mixtures thereof, and wherein the relative amount of said hydroxycarboxylic acid and polycarboxylic component is such that said copolymer has a maximum melting point of about 180° C.
Claim 27
Dependent Claim
83 words
A process for producing a copolymer which comprises: a) subjecting a hydroxycarboxylic acid to polycondensation, b) adding a polycarboxylic component prior to or during said polycondensation, c) causing said polycarboxylic component and hydroxycarboxylic acid to form a polymer; wherein said polycarboxylic component is selected from the group consisting of polycarboxylic acid, activated derivative thereof, and mixtures thereof, and wherein the relative amount of said hydroxycarboxylic acid and polycarboxylic component is such that said copolymer has a maximum melting point of about 180° C.
Claim 28
Dependent Claim
15 words
The process of claim 22 which further comprise reacting a metallic compound with said polymer.
Claim 29
Dependent Claim
20 words
The process of claim 23 wherein the metal cation of said metallic compound has a valence of at least two.
Claim 30
Dependent Claim
9 words
The copolymer obtained by the process of claim 22.
Claim 31
Dependent Claim
9 words
The copolymer obtained by the process of claim 23.
Claim 32
Dependent Claim
11 words
A fertilizer composition containing the copolymer of claim 1 and urea.
Claim 33
Dependent Claim
9 words
A fiber obtained from the copolymer of claim 1.
Claim 34
Dependent Claim
9 words
A fiber obtained from the copolymer of claim 13.
Claim 35
Dependent Claim
11 words
The fiber of claim 28 in the form of a suture.
Claim 36
Dependent Claim
22 words
The copolymer of claim 1 wherein said hydroxy carboxylic acid consists essentially of a hydroxyalkanoic acid containing 2 to 12 carbon atoms.
Claim 37
Dependent Claim
27 words
The copolymer of claim 1 wherein said activated derivative is selected from the group consisting of esters, anhydrides, acyl halides, trialkylsilyl esters, acyl imidazoles, ketenes and 0-acylureas.
Claim 38
Dependent Claim
21 words
The copolymer of claim 14 wherein said hydroxycarboxylic acid consists essentially of a hydroxyalkanoic acid containing 2 to 22 carbon atoms.
Claim 39
Dependent Claim
22 words
The copolymer of claim 13 wherein said hydroxy carboxylic acid consists essentially of a hydroxyalkanoic acid containing 2 to 12 carbon atoms.
Claim 40
Dependent Claim
29 words
The copolymer of claim 13 wherein the amount of said metallic compound is sufficient to neutralize about 0.1 to about 100% of the carboxylic terminal groups of the copolymer.
Claim 41
Dependent Claim
30 words
The copolymer of claim 13 wherein the metal cation of said metallic compound is selected from the group consisting of calcium, zinc, copper, iron, magnesium, cobalt, barium and mixtures thereof.
Claim 42
Dependent Claim
28 words
The copolymer of claim 13 wherein the anion of said metallic compound is selected from the groups consisting of acetylacetonate, acetate, formate, propionate, bicarbonate, carbonate and mixtures thereof.
Claim 43
Dependent Claim
35 words
The copolymer of claim 13 wherein said hydroxyalkanoic acid consists essentially of an acid selected from the group consisting of lactic acid, glycolic acid, β-hydroxybutyric acid, α-hydroxybutyric acid, δ-hydroxyvaleric acid, ε-hydroxycaproic acid and mixtures thereof.
Claim 44
Dependent Claim
15 words
The copolymer of claim 13 wherein said polycarboxylic acid contains 2 to 22 carbon atoms.
Claim 45
Dependent Claim
46 words
The copolymer of claim 13 wherein said polycarboxylic component consists essentially of a polycarboxylic acid selected from the group consisting of trimesic acid, succinic acid, fumaric acid, brassylic acid, adipic acid, ethylenediaminetetraacetic acid, nitrilotriacetic acid, citric acid, trimellitic acid, terephthalic acid, pyromellitic acid, and mixtures thereof.
Claim 46
Dependent Claim
41 words
The copolymer of claim 13 wherein said amount of said hydroxycarboxylic acid is about 99 to about 99.9 mole % and correspondingly said amount of said reactive carboxylic moieties of the polycarboxylic component is about 1 to about 0.1 mole %.
Claim 47
Dependent Claim
24 words
The copolymer of claim 13 wherein said hydroxy carboxylic acid contains only one primary reactive hydroxyl group or only one secondary reactive hydroxyl group.
Claim 48
Dependent Claim
27 words
The copolymer of claim 13 wherein said activated derivative is selected from the group consisting of esters, anhydrides, acyl halides, trialkylsilyl esters, acyl imidazoles, ketenes, and 0-acylureas.
Claim 49
Dependent Claim
21 words
The copolymer of claim 13 wherein said activated derivative consists essentially of an alkyl ester having 1 to 6 carbon atoms.
Claim 50
Dependent Claim
35 words
The copolymer of claim 13 wherein said anhydride derivative is selected from the group consisting of polypyromellitic anhydride, polyterephthalic anhydride phthalic anhydride, succinic anhydride, maleic anhydride, adipic anhydride, glutaric anhydride, polyisophthalic anhydride, and mixtures thereof.
Claim 51
Dependent Claim
15 words
The copolymer of claim 13 wherein said hydroxy carboxylic acid consists essentially of lactic acid.
Claim 52
Dependent Claim
21 words
The copolymer of claim 17 wherein said hydroxycarboxylic acid consists essentially of a hydroxyalkanoic acid containing 2 to 22 carbon atoms.
Claim 53
Dependent Claim
43 words
The copolymer of claim 47 wherein said polycarboxylic acid is selected from the group consisting of trimesic acid, succinic acid, fumaric acid, brassylic acid, adipic acid, ethylenediaminetetraacetic acid, nitrilotriacetic acid, citric acid, trimellitic acid, terephthalic acid, isophthalic acid, pyromellitic acid, and mixtures thereof.
Claim 54
Dependent Claim
15 words
The copolymer of claim 47 wherein said hydroxy alkanoic acid consists essentially of lactic acid.
Claim 55
Dependent Claim
24 words
The copolymer of claim 47 wherein said hydroxy carboxylic acid contains only one primary reactive hydroxy group or only one secondary reactive hydroxyl group.
Claim 56
Dependent Claim
27 words
The copolymer of claim 47 wherein said activated derivative is selected from the group consisting of esters, anhydrides, acyl halides, trialkylsilyl esters, acyl imidazoles, ketenes, and 0-acylureas.
Claim 57
Dependent Claim
29 words
The copolymer of claim 19 wherein the amount of said metallic compound is sufficient to neutralize about 0.1 to about 100% of the carboxyl terminal groups of the copolymer.
Claim 58
Dependent Claim
28 words
The copolymer of claim 19 wherein the anion of said metallic compound is selected from the group consisting of acetylacetonate, acetate, formate, propionate, bicarbonate, carbonate and mixtures thereof.
Claim 59
Dependent Claim
30 words
The copolymer of claim wherein said hydroxycarboxylic acid is selected from the group consisting of lactic acid, glycolic acid, β-hydroxybutyric acid, δ-hydroxybutyric acid, α-hydroxyvaleric acid, ε-hydroxycaproic acid and mixtures thereof.
Claim 60
Dependent Claim
43 words
The copolymer of claim 19 wherein said polycarboxylic acid is selected from the group consisting of trimesic acid, succinic acid, fumaric acid, brassylic acid, adipic acid, ethylenediaminetetraacetic acid, nitrilotriacetic acid, citric acid, trimellitic acid, terephthalic acid, isophthalic acid, pyromellitic acid, and mixtures thereof.
Claim 61
Dependent Claim
14 words
The copolymer of claim 19 wherein said hydroxy acid consists essentially of lactic acid.
Claim 62
Dependent Claim
23 words
The copolymer of claim wherein said hydroxy carboxylic acid contains only one primary reactive hydroxy group or only one secondary reactive hydroxyl group.
Claim 63
Dependent Claim
27 words
The copolymer of claim 19 wherein said activated derivative is selected from the group consisting of esters, anhydrides, acyl halides, trialkylsilyl esters, acyl imidazoles, ketenes and O-acylureas.
Claim 64
Dependent Claim
20 words
The process of claim 22 wherein the polycondensation is carried out at temperatures of about 160° to about 180° C.
Claim 65
Dependent Claim
20 words
The process of claim 22 wherein said hydroxycarboxylic acid consists essentially of hydroxyalkanoic acid containing 2 to 22 carbon atoms.
Claim 66
Dependent Claim
21 words
The process of claim 22 wherein said hydroxycarboxylic acid consists essentially of a hydroxyalkanoic acid containing 2 to 12 carbon atoms.
Claim 67
Dependent Claim
75 words
The process of claim 22 wherein the amount of said hydroxycarboxylic acid is about 99.95 mole % to about 90 mole % based upon the total moles of said hydroxycarboxylic acid and reactive carboxyl moieties of said polycarboxylic component; and corresponding said reactive carboxyl moieties of the polycarboxylic component is about 0.05 mole % to about 10 mole % based upon the total of said hydroxycarboxylic acid and reactive carboxyl moieties of the polycarboxylic component.
Claim 68
Dependent Claim
14 words
The process of claim 22 wherein said hydroxycarboxylic acid consists essentially of lactic acid.
Claim 69
Dependent Claim
42 words
The process of claim 22 wherein said polycarboxylic acid is selected from the group of trimesic acid, succinic acid, fumaric acid, brassylic acid, adipic acid, ethylenediaminetetraacetic acid, nitrilotriacetic acid, citric acid, trimellitic acid, terephthalic acid, isophthalic acid, pyromellitic acid and mixtures thereof.
Claim 70
Dependent Claim
29 words
The process of claim 23 wherein the amount of said metallic compound is sufficient to neutralize about 0.1 to about 100% of the carboxyl terminal groups of the copolymer.
Claim 71
Dependent Claim
30 words
The process of claim 23 wherein the metal cation of said metallic compound is selected from the group consisting of calcium, zinc, copper, iron, magnesium, cobalt, barium, and mixtures thereof.
Claim 72
Dependent Claim
19 words
The process of claim 23 wherein said metallic compound consists essentially of zinc or calcium salt or mixtures thereof.
Claim 73
Dependent Claim
28 words
The process of claim 23 wherein the anion of said metallic compound is selected from the group consisting of acetylacetonate, acetate, formate, propionate, bicarbonate, carbonate and mixtures thereof.
References Cited (Backward Citations)
US2363103A
Cited
US2433721A
Cited
US2449828A
Cited
US2453559A
Cited
US2555385A
Cited
BE584365A
Cited
US3284417A
Cited
US3498957A
Cited
US3579549A
Cited
US4139525A
Cited
US4273920A
Cited
US4507445A
Cited
JPH0413710A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1996-04-26 | 1996-10-26 | 1997-04-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-04-26 | 2000-10-26 | 2001-04-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-04-26 | 2004-10-26 | 2005-04-27 | $7700.00 | Window Closed / Lapsed |