US4176224A
Expired / Lapsed
US
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Poly (ethylene/alkylene) terephthalates which crystallize rapidly
Assignee: Bayer AG
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Filing: 1978-03-23
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Granted: 1979-11-27
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Expires: 1998-03-23
Abstract
Abstract The present invention is concerned with thermoplastic terephthalic acid copolyesters which crystallize more rapidly than homopolyethylene terephthalate and are based on a diol component which is about 98 to 99.9 mol % of ethylene glycol and the balance 2-ethylhexane-1,3-diol. The acid component may be up to about 10.0 mol % of other than terephthalic acid or its dimethyl ester. This invention is also concerned with a process of synthesizing such copolyesters by esterifying or transesterifying the acid and diol components between about 150° and 250° C. in the presence of appropriate catalysts. The condensation product may be subject to polycondensation at about 200° to 300° C. under reduced pressure in the presence of esterification catalysts. In a preferred embodiment the 2-ethylhexane-1,3-diol is added after the initial reaction between the acid component and the ethylene glycol and preferably after the degree of polycondensation is greater than 4.
Inventors
- 👤 Peter Bier
- 👤 Rudolf Binsack
- 👤 Hugo Vernaleken
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 13:24
CPC Classifications
C; C08; C08G; C08G63/00; C08G63/02; C08G63/12; C08G63/16; C08G63/18
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
59 words
A highly crystalline, thermoplastic terephthalic acid copolyester which crystallizes rapidly and consists of at least about 90 mol %, relative to the dicarboxylic acid component, of terephthalic acid radicals, about 98 to 99.9 mol %, relative to the diol component, of ethylene glycol radicals and about 0.1 to 2.0 mol %, relative to the diol component, of 2-ethylhexane-1,3-diol radicals.
Claim 2
Dependent Claim
59 words
A highly crystalline, thermoplastic terephthalic acid copolyester which crystallizes rapidly and consists of at least about 90 mol %, relative to the dicarboxylic acid component, of terephthalic acid radicals, about 98 to 99.9 mol %, relative to the diol component, of ethylene glycol radicals and about 0.1 to 2.0 mol %, relative to the diol component, of 2-ethylhexane-1,3-diol radicals.
Claim 3
Dependent Claim
27 words
The highly crystalline, thermoplastic terephthalic acid copolyester of claim 1, which has about 98.5 to 99.9 mol %, relative to the diol component, of ethylene glycol radicals.
Claim 4
Dependent Claim
27 words
The highly crystalline, thermoplastic terephthalic acid copolyester of claim 2, which has about 99.0 to 99.7 mol %, relative to the diol component, of ethylene glycol radicals.
Claim 5
Dependent Claim
44 words
The highly crystalline, thermoplastic terephthalic acid copolyester of claim 1, containing up to about 10 mol %, relative to the acid component of a radical selected from the residues of phthalic acid,/isophthalic acid, naphthalene-2,6-dicarboxylic acid, diphenyl-4,4'-dicarboxylic acid, adipic acid, sebacic acid and cyclohexanediacetic acid.
Claim 6
Dependent Claim
139 words
A process for the production of thermoplastic terephthalic acid copolyesters which crystallize more rapidly than polyethylene terephthalate homopolymer comprising (1) esterifying or transesterifying an acid component consisting of (a) at least about 90 mol % of terephthalic acid and dimethyl terephthalic acid ester, and (b) up to about 10 mol % of other aliphatic and aromatic dicarboxylic acids and acid esters with (2) about 1.05 to 5.0 equivalents of a diol component consisting of (a) about 98 to 99.9 mol % of ethylene glycol, and (b) about 0.1 to 2.0 mol % of 2-ethylhexane-1,3-diol at (3) a temperature of between about 150° and 250° C. in the presence of esterification or transesterification catalysts, and (4) polycondensing the initial reaction products at a temperature between about 200° and 300° C. under reduced pressure in the presence of an esterification catalyst.
Claim 7
Dependent Claim
139 words
A process for the production of thermoplastic terephthalic acid copolyesters which crystallize more rapidly than polyethylene terephthalate homopolymer comprising (1) esterifying or transesterifying an acid component consisting of (a) at least about 90 mol % of terephthalic acid and dimethyl terephthalic acid ester, and (b) up to about 10 mol % of other aliphatic and aromatic dicarboxylic acids and acid esters with (2) about 1.05 to 5.0 equivalents of a diol component consisting of (a) about 98 to 99.9 mol % of ethylene glycol, and (b) about 0.1 to 2.0 mol % of 2-ethylhexane-1,3-diol at (3) a temperature of between about 150° and 250° C. in the presence of esterification or transesterification catalysts, and (4) polycondensing the initial reaction products at a temperature between about 200° and 300° C. under reduced pressure in the presence of an esterification catalyst.
Claim 8
Dependent Claim
26 words
The process of claim 5 wherein the 2-ethylhexane-1,3-diol is added to the reaction mixture after substantially all of the acid component has been reacted to di(2-hydroxyethyl)ester.
Claim 9
Dependent Claim
34 words
The process of claim 6 wherein the codiol is added to the reacton mixture after formation of a polyethylene terephthalate prepolymer with a degree of polymerization greater than 4 but before the polycondensation step.
Claim 10
Dependent Claim
17 words
The process of claim 5 wherein the acid component is substantially all terephthalic acid and dimethyl terephthalate.
Claim 11
Dependent Claim
22 words
The process of claim 5 wherein between about 1.4 and 3.6 equivalents of diol component are used per equivalent of acid component.
Claim 12
Dependent Claim
17 words
A film, fiber or injection molded article formed from the thermoplastic terephthalic acid copolyester of claim 1.
Claim 13
Dependent Claim
14 words
An injection molded article formed from the thermoplastic terephthalic acid copolyester of claim 1.
Claim 14
Dependent Claim
8 words
The product of the process of claim 6.
Claim 15
Dependent Claim
8 words
The product of the process of claim 7.
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) | 1982-11-26 | 1983-05-28 | 1983-11-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-11-26 | 1987-05-28 | 1987-11-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-11-26 | 1991-05-28 | 1991-11-27 | $7700.00 | Window Closed / Lapsed |