US4139525A
Expired / Lapsed
US
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Flexible glycolic acid terpolymers
Assignee: Chevron USA Inc
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Filing: 1977-08-22
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Granted: 1979-02-13
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Expires: 1997-08-22
Abstract
Abstract Flexible glycolic acid terpolymers useful in the preparation of hot-melt adhesives are prepared by heating glycolic acid, its esters, its homopolymers or mixtures thereof with a dihydroxyalkane and a dibasic acid.
Inventors
- 👤 Robert Bacskai
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 12:19
CPC Classifications
C; C09; C09J; C09J167/00; C09J167/04; C08; C08G; C08G63/00; C08G63/02; C08G63/60
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
106 words
A polymer useful as a hot-melt adhesive produced by heating a mixture of glycolic acid, its homopolymers, its low-molecular-weight esters, or mixtures thereof, with a dihydroxyalkane and a dibasic acid, the dibasic acid being present in an amount from about 1% to about 40% by weight of the polymer, and the dihydroxyalkane being present in an amount from about equimolar with, up to a 10-mol percent excess over, the dibasic acid, said heating being carried out at a temperature from about 120° C. to about 270° C. for a period of time sufficient to produce a polymer having a molecular weight between about 2,000 and 70,000.
Claim 2
Dependent Claim
106 words
A polymer useful as a hot-melt adhesive produced by heating a mixture of glycolic acid, its homopolymers, its low-molecular-weight esters, or mixtures thereof, with a dihydroxyalkane and a dibasic acid, the dibasic acid being present in an amount from about 1% to about 40% by weight of the polymer, and the dihydroxyalkane being present in an amount from about equimolar with, up to a 10-mol percent excess over, the dibasic acid, said heating being carried out at a temperature from about 120° C. to about 270° C. for a period of time sufficient to produce a polymer having a molecular weight between about 2,000 and 70,000.
Claim 3
Dependent Claim
147 words
A polymer useful as a hot-melt adhesive produced by heating a mixture of glycolic acid, its homopolymers, its low-molecular-weight esters, or mixtures thereof, with a dihydroxyalkane and a dibasic acid, the dibasic acid being present in an amount from about 1% to about 40% by weight of the polymer, and the dihydroxyalkane being present in an amount from about equimolar with, up to a 10-mol percent excess over, the dibasic acid, the dihydroxyalkane being selected from diols having 2 to 14 carbon atoms, and the dibasic acid being selected from the group consisting of aliphatic diacids having 2 to 14 carbon atoms and the aromatic diacids having 6 to 12 carbon atoms, said heating being carried out at a temperature from about 120° C. to about 270° C. for a period of time sufficient to produce a polymer having a molecular weight between about 2,000 and 70,000.
Claim 4
Dependent Claim
147 words
A polymer useful as a hot-melt adhesive produced by heating a mixture of glycolic acid, its homopolymers, its low-molecular-weight esters, or mixtures thereof, with a dihydroxyalkane and a dibasic acid, the dibasic acid being present in an amount from about 1% to about 40% by weight of the polymer, and the dihydroxyalkane being present in an amount from about equimolar with, up to a 10-mol percent excess over, the dibasic acid, the dihydroxyalkane being selected from diols having 2 to 14 carbon atoms, and the dibasic acid being selected from the group consisting of aliphatic diacids having 2 to 14 carbon atoms and the aromatic diacids having 6 to 12 carbon atoms, said heating being carried out at a temperature from about 120° C. to about 270° C. for a period of time sufficient to produce a polymer having a molecular weight between about 2,000 and 70,000.
Claim 5
Dependent Claim
97 words
A polymer useful as a hot-melt adhesive produced by heating a mixture of glycolide with a dihydroxyalkane and a dibasic acid, the dibasic acid being present in an amount from about 1% to about 40% by weight of the polymer, and the dihydroxyalkane being present in an amount from about equimolar with, up to a 10-mol percent excess over, the dibasic acid, said heating being carried out at a temperature from about 120° C. to about 270° C. for a period of time sufficient to produce a polymer having a molecular weight between about 2,000 and 70,000.
Claim 6
Dependent Claim
97 words
A polymer useful as a hot-melt adhesive produced by heating a mixture of glycolide with a dihydroxyalkane and a dibasic acid, the dibasic acid being present in an amount from about 1% to about 40% by weight of the polymer, and the dihydroxyalkane being present in an amount from about equimolar with, up to a 10-mol percent excess over, the dibasic acid, said heating being carried out at a temperature from about 120° C. to about 270° C. for a period of time sufficient to produce a polymer having a molecular weight between about 2,000 and 70,000.
Claim 7
Dependent Claim
129 words
A polymer useful as a hot-melt adhesive produced by heating a mixture of glycolic acid, its homopolymers, its low-molecular-weight esters, or mixtures thereof, with a dihydroxyalkane and in an amount of from about 1% the about 40% by weight of the polymer of a dibasic acid selected from the group consisting of ethanedioic acid, propanedioic acid, butanedioic acid, hexanedioic acid, pentanedioic acid, pimelic acid, suberic acid, azelaic acid, diglycolic acid, and sebacic acid, the dihydroxyalkane being present in an amount from about equimolar with, up to a 10-mol percent excess over, the dibasic acid, said heating being carried out to a temperature from about 120° C. to about 270° C. for a period of time sufficient to produce a polymer having a molecular weight between about 2,000 and 70,000.
Claim 8
Dependent Claim
129 words
A polymer useful as a hot-melt adhesive produced by heating a mixture of glycolic acid, its homopolymers, its low-molecular-weight esters, or mixtures thereof, with a dihydroxyalkane and in an amount of from about 1% the about 40% by weight of the polymer of a dibasic acid selected from the group consisting of ethanedioic acid, propanedioic acid, butanedioic acid, hexanedioic acid, pentanedioic acid, pimelic acid, suberic acid, azelaic acid, diglycolic acid, and sebacic acid, the dihydroxyalkane being present in an amount from about equimolar with, up to a 10-mol percent excess over, the dibasic acid, said heating being carried out to a temperature from about 120° C. to about 270° C. for a period of time sufficient to produce a polymer having a molecular weight between about 2,000 and 70,000.
Claim 9
Dependent Claim
140 words
A polymer useful as a hot-melt adhesive produced by heating a mixture of glycolic acid, its homopolymers, its low-molecular-weight esters, or mixtures thereof, with a dihydroxyalkane and in an amount of from about 1% the about 40% by weight of the polymer of a dibasic acid selected from the group consisting of ethanedioic acid, propanedioic acid, butanedioic acid, hexanedioic acid, pentanedioic acid, pimelic acid, suberic acid, azelaic acid, diglycolic acid, and sebacic acid, the dihydroxyalkane being present in an amount from about equimolar with, up to a 10-mol percent excess over, the dibasic acid, and being selected from the group consisting of 1,2-glycols and 1,3-glycols, said heating being carried out at a temperature from about 120° C. to about 270° C. for a period of time sufficient to produce a polymer having a molecular weight between about 2,000 and 70,000.
Claim 10
Dependent Claim
140 words
A polymer useful as a hot-melt adhesive produced by heating a mixture of glycolic acid, its homopolymers, its low-molecular-weight esters, or mixtures thereof, with a dihydroxyalkane and in an amount of from about 1% the about 40% by weight of the polymer of a dibasic acid selected from the group consisting of ethanedioic acid, propanedioic acid, butanedioic acid, hexanedioic acid, pentanedioic acid, pimelic acid, suberic acid, azelaic acid, diglycolic acid, and sebacic acid, the dihydroxyalkane being present in an amount from about equimolar with, up to a 10-mol percent excess over, the dibasic acid, and being selected from the group consisting of 1,2-glycols and 1,3-glycols, said heating being carried out at a temperature from about 120° C. to about 270° C. for a period of time sufficient to produce a polymer having a molecular weight between about 2,000 and 70,000.
Claim 11
Dependent Claim
105 words
A polymer useful as a hot-melt adhesive produced by heating a mixture of glycolic acid, its homopolymers, its low-molecular-weight esters, or mixtures thereof, with a dihydroxyalkane and adipic acid, the adipic acid being present in an amount from about 1% to about 40% by weight of the polymer, and the dihydroxyalkane being present in an amount from about equimolar with, up to a 10-mol percent excess over, the adipic acid, said heating being carried out at a temperature from about 120° C. to about 270° C. for a period of time sufficient to produce a polymer having a molecular weight between about 2,000 and 70,000.
Claim 12
Dependent Claim
105 words
A polymer useful as a hot-melt adhesive produced by heating a mixture of glycolic acid, its homopolymers, its low-molecular-weight esters, or mixtures thereof, with a dihydroxyalkane and adipic acid, the adipic acid being present in an amount from about 1% to about 40% by weight of the polymer, and the dihydroxyalkane being present in an amount from about equimolar with, up to a 10-mol percent excess over, the adipic acid, said heating being carried out at a temperature from about 120° C. to about 270° C. for a period of time sufficient to produce a polymer having a molecular weight between about 2,000 and 70,000.
Claim 13
Dependent Claim
147 words
A polymer useful as a hot-melt adhesive produced by heating a mixture of glycolic acid, its homopolymers, its low-molecular-weight esters, or mixtures thereof, with (a) a dihydroxyalkane, (b) a minor amount relative to the dihydroxyalkane of a polyol having more than two hydroxyl groups, and (c) a dibasic acid, the dibasic acid being present in an amount from about 1% to about 40% by weight of the polymer, and the dihydroxyalkane being present in an amount from about equimolar with, up to a 10-mol percent excess over, the dibasic acid, the dihydroxyalkane and said polyol combined providing from about 2 to 2.2 equivalents of total hydroxyl group per mol of dibasic acid, said heating being carried out at a temperature from about 120° C. to about 270° C. for a period of time sufficient to produce a polymer having a molecular weight between about 2,000 and 70,000.
Claim 14
Dependent Claim
147 words
A polymer useful as a hot-melt adhesive produced by heating a mixture of glycolic acid, its homopolymers, its low-molecular-weight esters, or mixtures thereof, with (a) a dihydroxyalkane, (b) a minor amount relative to the dihydroxyalkane of a polyol having more than two hydroxyl groups, and (c) a dibasic acid, the dibasic acid being present in an amount from about 1% to about 40% by weight of the polymer, and the dihydroxyalkane being present in an amount from about equimolar with, up to a 10-mol percent excess over, the dibasic acid, the dihydroxyalkane and said polyol combined providing from about 2 to 2.2 equivalents of total hydroxyl group per mol of dibasic acid, said heating being carried out at a temperature from about 120° C. to about 270° C. for a period of time sufficient to produce a polymer having a molecular weight between about 2,000 and 70,000.
Claim 15
Dependent Claim
160 words
A polymer useful as a hot-melt adhesive produced by heating a mixture of glycolic acid, its homopolymers, its low-molecular-weight esters, or mixtures thereof, with (a) a dihydroxyalkane, (b) a minor amount relative to the dihydroxyalkane of a polyol selected from the group consisting of aliphatic triols and tetraols having from about 5 to about 15 carbon atoms, and (c) a dibasic acid, the dibasic acid being present in an amount from about 1% to about 40% by weight of the polymer, and the dihydroxyalkane being present in an amount from about equimolar with, up to a 10-mol percent excess over, the dibasic acid, the dihydroxyalkane and said polyol combined providing from about 2 to 2.2 equivalents of total hydroxyl group per mol of dibasic acid, said heating being carried out at a temperature from about 120° C. to about 270° C. for a period of time sufficient to produce a polymer having a molecular weight between about 2,000 and 70,000.
Claim 16
Dependent Claim
160 words
A polymer useful as a hot-melt adhesive produced by heating a mixture of glycolic acid, its homopolymers, its low-molecular-weight esters, or mixtures thereof, with (a) a dihydroxyalkane, (b) a minor amount relative to the dihydroxyalkane of a polyol selected from the group consisting of aliphatic triols and tetraols having from about 5 to about 15 carbon atoms, and (c) a dibasic acid, the dibasic acid being present in an amount from about 1% to about 40% by weight of the polymer, and the dihydroxyalkane being present in an amount from about equimolar with, up to a 10-mol percent excess over, the dibasic acid, the dihydroxyalkane and said polyol combined providing from about 2 to 2.2 equivalents of total hydroxyl group per mol of dibasic acid, said heating being carried out at a temperature from about 120° C. to about 270° C. for a period of time sufficient to produce a polymer having a molecular weight between about 2,000 and 70,000.
Claim 17
Dependent Claim
142 words
A polymer useful as a hot-melt adhesive produced by heating a mixture of glycolic acid, its homopolymers, its low-molecular-weight esters, or mixtures thereof, with (a) a dihydroxyalkane, (b) a minor amount relative to the dihydroxyalkane, of 1,1,1-trimethylolethane or pentaerythritol, and (c) a dibasic acid, the dibasic acid being present in an amount from about 1% to about 40% by weight of the polymer, and the dihydroxyalkane being present in an amount from about equimolar with, up to a 10-mol percent excess over, the dibasic acid, the dihydroxyalkane and said polyol combined providing from about 2 to 2.2 equivalents of total hydroxyl group per mol of dibasic acid, said heating being carried out at a temperature from about 120° C. to about 270° C. for a period of time sufficient to produce a polymer having a molecular weight between about 2,000 and 70,000.
Claim 18
Dependent Claim
142 words
A polymer useful as a hot-melt adhesive produced by heating a mixture of glycolic acid, its homopolymers, its low-molecular-weight esters, or mixtures thereof, with (a) a dihydroxyalkane, (b) a minor amount relative to the dihydroxyalkane, of 1,1,1-trimethylolethane or pentaerythritol, and (c) a dibasic acid, the dibasic acid being present in an amount from about 1% to about 40% by weight of the polymer, and the dihydroxyalkane being present in an amount from about equimolar with, up to a 10-mol percent excess over, the dibasic acid, the dihydroxyalkane and said polyol combined providing from about 2 to 2.2 equivalents of total hydroxyl group per mol of dibasic acid, said heating being carried out at a temperature from about 120° C. to about 270° C. for a period of time sufficient to produce a polymer having a molecular weight between about 2,000 and 70,000.
Claim 19
Dependent Claim
73 words
A glycolic acid polymer comprising from about 98% to about 85% by weight of glycolic acid, and from about 2% to about 15% by weight of adipic acid, ethylene glycol, and 1,1,1-trimethylol ethane wherein the molar amount of said adipitc acid is equivalent to the combined molar amounts of said glycol and said trimethylol ethane and the molar ratio of said glycol to said trimethylol ethane is from about 10:1 to about 5:1.
Claim 20
Dependent Claim
73 words
A glycolic acid polymer comprising from about 98% to about 85% by weight of glycolic acid, and from about 2% to about 15% by weight of adipic acid, ethylene glycol, and 1,1,1-trimethylol ethane wherein the molar amount of said adipitc acid is equivalent to the combined molar amounts of said glycol and said trimethylol ethane and the molar ratio of said glycol to said trimethylol ethane is from about 10:1 to about 5:1.
Claim 21
Dependent Claim
68 words
A polymer comprising from about 98% to about 85%, by weight, of glycolic acid, and from about 2% to about 15% by weight of adipic acid, ethylene glycol and pentaerythritol wherein the molar amounts of the adipic acid is equivalent to the combined molar amounts of the glycol and the pentaerythritol, and the molar ratio of the glycol to the pentaerythritol is from about 10:1 to about 5:1.
Claim 22
Dependent Claim
68 words
A polymer comprising from about 98% to about 85%, by weight, of glycolic acid, and from about 2% to about 15% by weight of adipic acid, ethylene glycol and pentaerythritol wherein the molar amounts of the adipic acid is equivalent to the combined molar amounts of the glycol and the pentaerythritol, and the molar ratio of the glycol to the pentaerythritol is from about 10:1 to about 5:1.
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) | 1982-02-12 | 1982-08-14 | 1983-02-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-02-12 | 1986-08-14 | 1987-02-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-02-12 | 1990-08-14 | 1991-02-13 | $7700.00 | Window Closed / Lapsed |