US4312975A
Expired / Lapsed
US
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Bisphenol-dicarboxylic acid diester and compositions thereof with linear aromatic polyester having improved processability
Assignee: Celanese Corp
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Filing: 1979-06-04
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Granted: 1982-01-26
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Expires: 1999-06-04
Abstract
Abstract There is disclosed a diester of a bisphenol having two dicarboxylic acid residues wherein the dicarboxylic acid residues terminate in carboxylic acid ester groups derived from a long chain aliphatic monofunctional hydrocarbon alcohol. Compositions of the diester and a linear aromatic polyester of a bisphenol and dicarboxylic acid are characterized by enhanced processability and enhanced hydrolytic stability compared to the polyester.
Inventors
- 👤 Gideon Salee
- 👤 Jerold C. Rosenfeld
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 21:51
CPC Classifications
C; C08; C08G; C08G63/00; C08G63/02; C08G63/12; C08G63/16; C08G63/18; C08G63/19; C08K; C08K5/00; C08K5/04; C08K5/10; C08K5/12
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
179 words
A diester of a bisphenol and a dicarboxylic acid having the structural formula: ##STR11## wherein Ar is aromatic, G is alkyl, haloalkyl, aryl, haloaryl, alkylaryl, haloalkylaryl, arylalkyl, haloarylalkyl, cycloalkyl or halocycloalkyl; E is a divalent alkylene, haloalkylene, cycloalkylene, halocycloalkylene, arylene or haloarylene, --O--, --S--, --SO--, --SO 2 --, --SO 3 --, --CO--, ##STR12## or GN<; T and T' are independently selected from halogen, G and OG; m is an integer from 0 to the number of replaceable hydrogen atoms on E; b is an integer from 0 to the number of replaceable hydrogen atoms on Ar; x is 0 or 1; Z and Z' are like or different groups selected from the group consisting of --Ar'-- and --Ar'--Y--Ar'-- where Ar' has the same meaning as Ar; Y is an alkylene group of 1 to 10 carbon atoms, haloalkylene, --O--, --S--, --SO--, --SO 2 --, --SO 3 --, --CO--, ##STR13## or GN<; n and n' are independently selected from integers 0 and 1; and R and R' are independently selected from aliphatic hydrocarbon groups of 8 to 45 carbon atoms.
Claim 2
Dependent Claim
179 words
A diester of a bisphenol and a dicarboxylic acid having the structural formula: ##STR11## wherein Ar is aromatic, G is alkyl, haloalkyl, aryl, haloaryl, alkylaryl, haloalkylaryl, arylalkyl, haloarylalkyl, cycloalkyl or halocycloalkyl; E is a divalent alkylene, haloalkylene, cycloalkylene, halocycloalkylene, arylene or haloarylene, --O--, --S--, --SO--, --SO 2 --, --SO 3 --, --CO--, ##STR12## or GN<; T and T' are independently selected from halogen, G and OG; m is an integer from 0 to the number of replaceable hydrogen atoms on E; b is an integer from 0 to the number of replaceable hydrogen atoms on Ar; x is 0 or 1; Z and Z' are like or different groups selected from the group consisting of --Ar'-- and --Ar'--Y--Ar'-- where Ar' has the same meaning as Ar; Y is an alkylene group of 1 to 10 carbon atoms, haloalkylene, --O--, --S--, --SO--, --SO 2 --, --SO 3 --, --CO--, ##STR13## or GN<; n and n' are independently selected from integers 0 and 1; and R and R' are independently selected from aliphatic hydrocarbon groups of 8 to 45 carbon atoms.
Claim 3
Dependent Claim
27 words
The diester of claim 1 wherein n and n'=1 and --Ar'-- is an aromatic radical of the benzene or naphthalene series containing 6 to 20 carbon atoms.
Claim 4
Dependent Claim
19 words
The diester of claim 2 wherein Z and Z' are --Ar'-- and --Ar'-- contains only hydrogen to carbon bonds.
Claim 5
Dependent Claim
13 words
The diester of claim 3 wherein --Ar'-- is an m-phenylene or p-phenylene group.
Claim 6
Dependent Claim
13 words
The diester of claim 4 wherein Z and Z' represent identical organic groups.
Claim 7
Dependent Claim
30 words
The diester of claim 1 wherein --Ar-- is p-phenylene, T and T' are hydrogen, b is 4, E is methylene, G is methyl, X is 0, and m is 2.
Claim 8
Dependent Claim
14 words
The diester of claim 6 wherein R and R' represent saturated aliphatic hydrocarbon groups.
Claim 9
Dependent Claim
15 words
The diester of claim 7 wherein R and R' represent the same aliphatic hydrocarbon groups.
Claim 10
Dependent Claim
20 words
The diester of claim 8 wherein R and R' are acyclic aliphatic hydrocarbon groups of 9 to 40 carbon atoms.
Claim 11
Dependent Claim
22 words
The diester of claim 9 wherein R and R' are straight chain acyclic aliphatic hydrocarbon groups of 12 to 30 carbon atoms.
Claim 12
Dependent Claim
19 words
The diester of claim 10 wherein R and R' are aliphatic hydrocarbon groups of 15 to 20 carbon atoms.
Claim 13
Dependent Claim
27 words
The diester of claim 11 wherein n and n' are 1; Z and Z' represent a m-phenylene or p-phenylene group and R and R' are n-stearyl groups.
Claim 14
Dependent Claim
13 words
The diester of claim 12 wherein Z and Z' are a m-phenylene group.
Claim 15
Dependent Claim
13 words
The diester of claim 12 wherein Z and Z' are a p-phenylene group.
Claim 16
Dependent Claim
71 words
In the preparation of a diester by reaction of a bisphenol and an aromatic dicarboxylic acid diacyl halide, the improvement which comprises forming a mixture of the diacyl halide with a monofunctional aliphatic alcohol of 8 to 45 carbon atoms and completing esterification of said mixture prior to any reaction of the bisphenol with the diacyl halide, the diacyl halide, the alcohol and the bisphenol being charged in about stoichiometric proportions.
Claim 17
Dependent Claim
71 words
In the preparation of a diester by reaction of a bisphenol and an aromatic dicarboxylic acid diacyl halide, the improvement which comprises forming a mixture of the diacyl halide with a monofunctional aliphatic alcohol of 8 to 45 carbon atoms and completing esterification of said mixture prior to any reaction of the bisphenol with the diacyl halide, the diacyl halide, the alcohol and the bisphenol being charged in about stoichiometric proportions.
Claim 18
Dependent Claim
28 words
The process of claim 15 wherein the diacyl halide is isophthaloyl chloride, terephthaloyl chloride or mixtures thereof, the aliphatic alcohol is stearyl alcohol and the bisphenol is bisphenol-A.
Claim 19
Dependent Claim
49 words
A thermoplastic polymeric composition comprising in admixture (a) a linear aromatic polyester of components comprising a bisphenol and a dicarboxylic acid and (b) greater than about 1 weight percent to less than about 50 weight percent based on the weight of said polyester, of the diester of claim 1.
Claim 20
Dependent Claim
63 words
The composition of claim 17 wherein said dicarboxylic acid of the polyester has the formula: ##STR14## wherein Z is alkylene, --Ar-- or --Ar--Y--Ar-- where Ar is aromatic, Y is alkylene, haloalkylene, --O--, --S--, --SO 2 --, --SO 3 --, --CO--, ##STR15## or GN<, wherein G is alkyl, haloalkyl, aryl, haloaryl, alkylaryl, haloalkylaryl, arylarlkyl, haloarylalkyl, cycloalkyl or cyclohaloalkyl; and n" is 0 or 1.
Claim 21
Dependent Claim
17 words
The composition of claim 18 wherein said dicarboxylic acid of the polyester is an aromatic dicarboxylic acid.
Claim 22
Dependent Claim
27 words
The composition of claim 19 wherein said aromatic dicarboxylic acid of the polyester is selected from the group consisting of isophthalic acid, terephthalic acid, and mixtures thereof.
Claim 23
Dependent Claim
106 words
The composition of claim 20 wherein said bisphenol of the polyester has the formula: ##STR16## wherein Ar is aromatic, G is alkyl, haloalkyl, aryl, haloaryl, alkylaryl, haloalkylaryl, arylalkyl, haloarylalkyl, cycloalkyl, or cyclohaloalkyl; E is divalent alkylene, haloalkylene, cycloalkylene, halocycloalkylene, arylene, or haloarylene, --O--, --S--, --SO--, --SO 2 --, --SO 3 --, --CO--, ##STR17## or GN<; T and T' are independently selected from the group consisting of halogen, G and OG; m is an integer from 0 to the number of replaceable hydrogen atoms on E; b is an integer from 0 to the number of replaceable hydrogen atoms on Ar, and x is 0 or 1.
Claim 24
Dependent Claim
13 words
The composition of claim 21 wherein the bisphenol of the polyester is bisphenol-A.
Claim 25
Dependent Claim
14 words
The composition of claim 22 wherein the diester is the diester of claim 14.
Claim 26
Dependent Claim
14 words
The composition of claim 17 wherein said linear aromatic polyester includes an aliphatic modifier.
Claim 27
Dependent Claim
18 words
The composition of claim 24 wherein said aliphatic modifier is a glycol of 2 to 100 carbon atoms.
Claim 28
Dependent Claim
24 words
The composition of claim 25 wherein said glycol is selected from the group consisting of neopentyl glycol, diethylene glycol, ethylene glycol, and mixtures thereof.
Claim 29
Dependent Claim
16 words
The composition of claim 1 wherein the aromatic polyester is prepared by a melt polymerization technique.
Claim 30
Dependent Claim
11 words
The composition of claim 17 which also includes a filler material.
Claim 31
Dependent Claim
12 words
The composition of claim 28 wherein said filler material is particulate glass.
Claim 32
Dependent Claim
35 words
The composition of claim 29 wherein the filler material is glass fiber present in an amount of about 5 to about 70 weight percent based on the combined weight of the polyester and the diester.
Claim 33
Dependent Claim
25 words
The composition of claim 17 wherein the diester is present in an amount of from about 3 to about 30 weight percent of the polyester.
Claim 34
Dependent Claim
25 words
The composition of claim 31 wherein the diester is present in an amount of from about 5 to about 20 weight percent of the polyester.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-01-25 | 1985-07-27 | 1986-01-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-01-25 | 1989-07-27 | 1990-01-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-01-25 | 1993-07-27 | 1994-01-26 | $7700.00 | Window Closed / Lapsed |