CA1268892A - Wholly aromatic polyether esters and the preparation thereof - Google Patents
Wholly aromatic polyether esters and the preparation thereofInfo
- Publication number
- CA1268892A CA1268892A CA000524449A CA524449A CA1268892A CA 1268892 A CA1268892 A CA 1268892A CA 000524449 A CA000524449 A CA 000524449A CA 524449 A CA524449 A CA 524449A CA 1268892 A CA1268892 A CA 1268892A
- Authority
- CA
- Canada
- Prior art keywords
- mol
- wholly aromatic
- repeat units
- polyether ester
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/60—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
- C08G63/605—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds the hydroxy and carboxylic groups being bound to aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
- 11 - O.Z. 0050/38135 Abstract of the Disclosure: Wholly aromatic polyether esters which form a liquid-crystalline fiber-forming melt at below 300°C are composed of a) not less than 10 mol % of repeat units of the for-mula I
I
b) a molar amount equivalent to the total amount of components c) and d) of repeat units of the formula II
II
c) from 5 to 20 mol % of repeat units of the formula III
III
and d) from 10 to 30 mol % of repeat units of the formula IV
IV
the molar proportions of components a, b, c and d adding up to 100 mol % in each case, the preparation thereof, andfibers, films, moldings and surface coating materials prepared therefrom.
I
b) a molar amount equivalent to the total amount of components c) and d) of repeat units of the formula II
II
c) from 5 to 20 mol % of repeat units of the formula III
III
and d) from 10 to 30 mol % of repeat units of the formula IV
IV
the molar proportions of components a, b, c and d adding up to 100 mol % in each case, the preparation thereof, andfibers, films, moldings and surface coating materials prepared therefrom.
Description
` ~26~3a~3~
- 1 - O.Z. OOS0/3~135 Wholly aromatic polyether esters and the preparation thereof The present invention relates to wholly aromatic polyether esters which form a liquid-crystalline fiber-forming melt below 300C.
Wholly aromatic liquid-crystall;ne polyesters ~re known. However, these polyesters lack adequate heat dis-tortion resistance, and the surface quality thereof, in particular the abrasion resistance, is also unsatisfactory.
EP Application 115,967 describes add;ng from 10 to 70%
by volume of wollastonite to aromatic polyesters which are based on hydroxynaphthalenecarboxylic acid, tereph-thalic acid and aromatic dihydroxy compounds, to improve the abrasion resistance. However, the addition of such fillers impairs other properties of the polymer. EP App-lication ~1,900 proposes 4,4 -d;(p-hydroxyphenoxy)diphenyl sulfone as a possibLe starting material for the prePara-tion of anisotropic polyester amides and polyesters, but provides no indication as to the surface quality of the products obtained or the heat distortion resistance thereof.
lt is an object of the present invention to pro-vide wholly aromatic liquid-crystalline polyether esters which form a liquid-crystalline fiber-forming melt below 300C and thus are easy to process and which also have a very high glass transition temperature, a high abrasion resistance and a high chemical resistance.
~e have found that this object is achieved with wholly aromatic polyether esters which form a liquid-crystalline fiber-forming melt below 300C and are cc,mposed of a) not less than 10 mol % of repeat units of the for-mula I
r~ !l ~ ' I
b) a molar amount equivalent to the ~otal amoun~ of components c) and d) of repeat units of the formula II
12~
. ~
- 1 - O.Z. OOS0/3~135 Wholly aromatic polyether esters and the preparation thereof The present invention relates to wholly aromatic polyether esters which form a liquid-crystalline fiber-forming melt below 300C.
Wholly aromatic liquid-crystall;ne polyesters ~re known. However, these polyesters lack adequate heat dis-tortion resistance, and the surface quality thereof, in particular the abrasion resistance, is also unsatisfactory.
EP Application 115,967 describes add;ng from 10 to 70%
by volume of wollastonite to aromatic polyesters which are based on hydroxynaphthalenecarboxylic acid, tereph-thalic acid and aromatic dihydroxy compounds, to improve the abrasion resistance. However, the addition of such fillers impairs other properties of the polymer. EP App-lication ~1,900 proposes 4,4 -d;(p-hydroxyphenoxy)diphenyl sulfone as a possibLe starting material for the prePara-tion of anisotropic polyester amides and polyesters, but provides no indication as to the surface quality of the products obtained or the heat distortion resistance thereof.
lt is an object of the present invention to pro-vide wholly aromatic liquid-crystalline polyether esters which form a liquid-crystalline fiber-forming melt below 300C and thus are easy to process and which also have a very high glass transition temperature, a high abrasion resistance and a high chemical resistance.
~e have found that this object is achieved with wholly aromatic polyether esters which form a liquid-crystalline fiber-forming melt below 300C and are cc,mposed of a) not less than 10 mol % of repeat units of the for-mula I
r~ !l ~ ' I
b) a molar amount equivalent to the ~otal amoun~ of components c) and d) of repeat units of the formula II
12~
. ~
- 2 - O.Z. 0050/38135 c) from 5 to 20 mol % of repeat units of the formula III
-o ~ o ~ 502 ~ o- III
and d) from 10 to 30 mol % of repeat units of the formula IV
CH~
~ IV
the molar proportions of components a, b, c and d adding 1û up to 1~0 mol % in each case.
The novel wholly aromatic liquid-crystalline poly-ether esters have the advantage of not requiring high pro-cessing temperatures and, what is more, of having excel-lent sustained use properties even at elevated tempera-tures. They also have high abrasion resistance and chemi-cal resistance.
The liquid-crystalline state of the polyether es ters can be detected with a polarization microscope by a method described in German Published Application DAS
Z0 2,520,810. Applied in a thickness of 10 ~m between glass plates and viewed between crossed polarizers, the polymer melts have ~extures which can be ascribed to a mesomorphic ~nematic) phase.
The polyether esters accurding to the invention are composed of a) not less than 10 mol % of repeat units of the formula I
o ~_ I
88~
-o ~ o ~ 502 ~ o- III
and d) from 10 to 30 mol % of repeat units of the formula IV
CH~
~ IV
the molar proportions of components a, b, c and d adding 1û up to 1~0 mol % in each case.
The novel wholly aromatic liquid-crystalline poly-ether esters have the advantage of not requiring high pro-cessing temperatures and, what is more, of having excel-lent sustained use properties even at elevated tempera-tures. They also have high abrasion resistance and chemi-cal resistance.
The liquid-crystalline state of the polyether es ters can be detected with a polarization microscope by a method described in German Published Application DAS
Z0 2,520,810. Applied in a thickness of 10 ~m between glass plates and viewed between crossed polarizers, the polymer melts have ~extures which can be ascribed to a mesomorphic ~nematic) phase.
The polyether esters accurding to the invention are composed of a) not less than 10 mol % of repeat units of the formula I
o ~_ I
88~
- 3 - O.Z. 0050/38135 a possible starting material being, for exampLe, p-hydroxy-benzoic acid, b) a molar amount corresponding to the total amount of c) and d) of repeat units of the formula II
~ f C ~ C- II
a preferred starting compound being terephthalic acid, c) from 5 to 20 mol % of repeat units of the formula III
--O~ O ~ SO2 ~ o ~ o-- III
a starting compound being, for example, 4,4'-di(p-hydroxy-phenoxy)diphenyl sulfone and d) from 10 to 30 mol % of repeat units of the formula IV
H~C-C-CH3 I V
an advantageous starting compound being tert-butylhydro-quinone.
Preferred wholly aromatic polyether esters contain in addition to component a) from 10 to 15 mol % of com-ponent c), from 15 to 25 mol % of component d) and a molar Z0 amount equivalent to the total amount of c) and d) of com-ponent b).
In other preferred wholly aromatic polyether esters, some of units d) are replaced by e) repeat units of the formula V
~0 V
a starting compound being~ for example, hydroquinone, and/
or f) repeat units of the formula VI
~,88~
~ f C ~ C- II
a preferred starting compound being terephthalic acid, c) from 5 to 20 mol % of repeat units of the formula III
--O~ O ~ SO2 ~ o ~ o-- III
a starting compound being, for example, 4,4'-di(p-hydroxy-phenoxy)diphenyl sulfone and d) from 10 to 30 mol % of repeat units of the formula IV
H~C-C-CH3 I V
an advantageous starting compound being tert-butylhydro-quinone.
Preferred wholly aromatic polyether esters contain in addition to component a) from 10 to 15 mol % of com-ponent c), from 15 to 25 mol % of component d) and a molar Z0 amount equivalent to the total amount of c) and d) of com-ponent b).
In other preferred wholly aromatic polyether esters, some of units d) are replaced by e) repeat units of the formula V
~0 V
a starting compound being~ for example, hydroquinone, and/
or f) repeat units of the formula VI
~,88~
- 4 - O.Z. 0050/38135 - ~ YI
a suitable starting compound being, preferably, 4,4'-dihy-droxybiphenyl, and/or g) repeat units of the formula VII
_ ~ o-~l~n VII
where R is methyl, phenyl or chlorine and n is 1, 2 or 3.
Suitable starting compounds are methylhydroquinone, tri-methylhydroquinone, phenylhydroquinone and chlorohydro-quinone.
Advantageously these wholly aromatic polyether esters contain repeat units e) and/or f3 in an a~ount of from 5 to 10 mol %. In another preferred composition, the wholly aromatic polyether esters contain component g) in an amount from 5 to 20 mol %.
It ~ill be readily understood that the propor-tions of components a, b, c and d add up to 100 mol % in each case.
Preferred wholly aromat;c li~uid-crystalline poly-ether esters have a glass transition temperature of > 150C, in particular > 160C. This glass transition temperature is measured by the DSC method described by K. H~ Illers et al. in Makromol. Chem. 127 (1969), 1. Preference is given to li~uid-crystalline polyether esters which have partial crystallinity at > 220C and < 280C. The poly~
ether esters according to the invention form a liquicl-crystalline fiber-forming melt at < 300C.
The liquid-crystalline polyether esters according to the invention can be prepared by various methods, for example as described in US Patents 4,375,530 and 4,118,372.
The mass condensation generally includes an alka-noylating stage, where the monomers used are reacted with anhydridesr and a polymerization stage, in which the i8~39~
O~Z. 0050/38135 polycondensate is formed by elimination of aliphatic carb-oxylic acids. Processes which include a prepolymeriza-tion stage are described in German Laid-Open Application DOS 3,320,118. However, these processes require reaction times of more than 10 hours.
In an advantageous embodiment, the polyesters ac-cording to the invention are obtained in a single-stage process by converting the underivatized starting materials us;ng anhydrides of lower fatty acids, for example fatty acids of 2 to 4 carbon atoms, in particular acetic anhyd-ride~ Advantageously this reaction is catalyzed with known catalysts for polycondensation and transesterifica-tion reactions, used in an amount of from 0.001 to 1% by weight, based on the starting materials. The starting materials are heated together with, for example, acetic anhydride, which is advantageously present in a molar ex-cess of not less than 5%, based on the hydroxyl groups present, with stirring, preferably under an inert gas, to a temperature at which reflux occurs. Advantageously the temperature is increased in stages, for example to 150-220C in not more than 5 hours, preferably up to 2 hours, and the temperature is then slowly raised to 250-350C, while excess fatty ac;d anhydride and fatty acid are dis-tilled off. To remove the last residues of fatty acid, it is expedient to employ recluced pressure, ~or example do~n to 0.5 mbar, to~ard the end of the condensation.
It is a remarkable and unforeseeable feature of this single-stage process that the desired poLymers are obtained in a relatively short time in a troublefree and complete reaction even without catalysts. This is all the more astonishing as the large number of chemically diff-erent hydroxyl groups would be expected tv lead to differ-ences in reactivity and hence to inadequate polymer synthe-s i s .
The wholly aromatic liquid-crystalline polyether esters thus obtained are advantageously further condensed in the solid state, for example at 150 250C~ until the ~2~i~8~;~
- 6 - O.Z. 0050/38135 desired viscosity is obtained. This solid phase condensa-tion can take place not only be~ore but also after thermo-plastic forming. The wholly aromatic liquid-crystalline polyether esters according to the invention are suitable for preparing filaments, films, foams and industrial mold-ings by injection molding or extruding.
The invention is illustrated by the following Examples.
0.2 mol (30.3 mol %) of terephthalic acid, 0.26 mol (39.4 mol %) of 4-hydroxybenzoic ac;d, 0.16 mol (24.24 mol %) of t-butylhydroquinone, 0.04 mol ~.06 mol X) of 4,4'-di(p-hydroxyphenoxy)diphenyl sulfone and 0.86 mol of acetic anhydride are weighed into a flask equipped with stirrer, nitrogen inlet and distillation attachment.
Under nitrogen the contents are then heated in a metal bath to 100C. The temperature is then raised to 150C
in 30', to 200C ;n a further 100' and finally to 325C in 120'.
The pressure is then reduced to 560 mbar and sub-sequently halved every 10'. The final vacuum is 10 mbar.
In this way a highly viscous fiber-forming mesomorphic melt is obtain~d. DSC measurements indicate a glass tran-sition temperature of 156C. The intrinsic viscosity is 25 0.9 dl/g, measured at 50C in an 0.5% strength by weight solution in p-chlorophenol.
The polymer can be processed from the melt at T
> Tg, in particular at T 2 200C.
0.2 mol (30.3 mol %) of terephthalic acid~ 0.26 mol (39.4 mol X) of 4-hydroxybenzoic acid, 0.12 mol (18.2 mol %) of t-butylhydroquinone, 0.08 mol (12.1 mol X) of 4,4'-di(p-hydroxyphenoxy)phenyl sulfone and 0.86 mol of acetic anhy-dride are reacted as in Example 1. DSC measurements indi-cate a glass transition temperature of 166C~ The intrin-sic viscosity is 0.5 dl/g. The polymer can be processed from the melt at T > Tg, in particular at T 2 200C.
2~
7 O.~. 0050/38135 0.2 mol (27.03 mol %) of terephthalic acid, 0.34 mol (45.94 mol %) of 4-hydroxybenzoic acid, 0.16 mol (21.62 mol %) of t-butylhydroquinone, 0.04 mol (5.41 mol ~) of 4,4'-di(p-hydroxyphenoxy)diphenyl sulfone and 0.86 mol of acetic anhydride are reacted as in Example 1. DSC
measurements indicate a glass transition temperature of 165C. The intrinsic viscosity is 0.93 dl/g. The poly-mer can be processed from the melt at T > Tg, in particu-lar at T 2 200C.
a suitable starting compound being, preferably, 4,4'-dihy-droxybiphenyl, and/or g) repeat units of the formula VII
_ ~ o-~l~n VII
where R is methyl, phenyl or chlorine and n is 1, 2 or 3.
Suitable starting compounds are methylhydroquinone, tri-methylhydroquinone, phenylhydroquinone and chlorohydro-quinone.
Advantageously these wholly aromatic polyether esters contain repeat units e) and/or f3 in an a~ount of from 5 to 10 mol %. In another preferred composition, the wholly aromatic polyether esters contain component g) in an amount from 5 to 20 mol %.
It ~ill be readily understood that the propor-tions of components a, b, c and d add up to 100 mol % in each case.
Preferred wholly aromat;c li~uid-crystalline poly-ether esters have a glass transition temperature of > 150C, in particular > 160C. This glass transition temperature is measured by the DSC method described by K. H~ Illers et al. in Makromol. Chem. 127 (1969), 1. Preference is given to li~uid-crystalline polyether esters which have partial crystallinity at > 220C and < 280C. The poly~
ether esters according to the invention form a liquicl-crystalline fiber-forming melt at < 300C.
The liquid-crystalline polyether esters according to the invention can be prepared by various methods, for example as described in US Patents 4,375,530 and 4,118,372.
The mass condensation generally includes an alka-noylating stage, where the monomers used are reacted with anhydridesr and a polymerization stage, in which the i8~39~
O~Z. 0050/38135 polycondensate is formed by elimination of aliphatic carb-oxylic acids. Processes which include a prepolymeriza-tion stage are described in German Laid-Open Application DOS 3,320,118. However, these processes require reaction times of more than 10 hours.
In an advantageous embodiment, the polyesters ac-cording to the invention are obtained in a single-stage process by converting the underivatized starting materials us;ng anhydrides of lower fatty acids, for example fatty acids of 2 to 4 carbon atoms, in particular acetic anhyd-ride~ Advantageously this reaction is catalyzed with known catalysts for polycondensation and transesterifica-tion reactions, used in an amount of from 0.001 to 1% by weight, based on the starting materials. The starting materials are heated together with, for example, acetic anhydride, which is advantageously present in a molar ex-cess of not less than 5%, based on the hydroxyl groups present, with stirring, preferably under an inert gas, to a temperature at which reflux occurs. Advantageously the temperature is increased in stages, for example to 150-220C in not more than 5 hours, preferably up to 2 hours, and the temperature is then slowly raised to 250-350C, while excess fatty ac;d anhydride and fatty acid are dis-tilled off. To remove the last residues of fatty acid, it is expedient to employ recluced pressure, ~or example do~n to 0.5 mbar, to~ard the end of the condensation.
It is a remarkable and unforeseeable feature of this single-stage process that the desired poLymers are obtained in a relatively short time in a troublefree and complete reaction even without catalysts. This is all the more astonishing as the large number of chemically diff-erent hydroxyl groups would be expected tv lead to differ-ences in reactivity and hence to inadequate polymer synthe-s i s .
The wholly aromatic liquid-crystalline polyether esters thus obtained are advantageously further condensed in the solid state, for example at 150 250C~ until the ~2~i~8~;~
- 6 - O.Z. 0050/38135 desired viscosity is obtained. This solid phase condensa-tion can take place not only be~ore but also after thermo-plastic forming. The wholly aromatic liquid-crystalline polyether esters according to the invention are suitable for preparing filaments, films, foams and industrial mold-ings by injection molding or extruding.
The invention is illustrated by the following Examples.
0.2 mol (30.3 mol %) of terephthalic acid, 0.26 mol (39.4 mol %) of 4-hydroxybenzoic ac;d, 0.16 mol (24.24 mol %) of t-butylhydroquinone, 0.04 mol ~.06 mol X) of 4,4'-di(p-hydroxyphenoxy)diphenyl sulfone and 0.86 mol of acetic anhydride are weighed into a flask equipped with stirrer, nitrogen inlet and distillation attachment.
Under nitrogen the contents are then heated in a metal bath to 100C. The temperature is then raised to 150C
in 30', to 200C ;n a further 100' and finally to 325C in 120'.
The pressure is then reduced to 560 mbar and sub-sequently halved every 10'. The final vacuum is 10 mbar.
In this way a highly viscous fiber-forming mesomorphic melt is obtain~d. DSC measurements indicate a glass tran-sition temperature of 156C. The intrinsic viscosity is 25 0.9 dl/g, measured at 50C in an 0.5% strength by weight solution in p-chlorophenol.
The polymer can be processed from the melt at T
> Tg, in particular at T 2 200C.
0.2 mol (30.3 mol %) of terephthalic acid~ 0.26 mol (39.4 mol X) of 4-hydroxybenzoic acid, 0.12 mol (18.2 mol %) of t-butylhydroquinone, 0.08 mol (12.1 mol X) of 4,4'-di(p-hydroxyphenoxy)phenyl sulfone and 0.86 mol of acetic anhy-dride are reacted as in Example 1. DSC measurements indi-cate a glass transition temperature of 166C~ The intrin-sic viscosity is 0.5 dl/g. The polymer can be processed from the melt at T > Tg, in particular at T 2 200C.
2~
7 O.~. 0050/38135 0.2 mol (27.03 mol %) of terephthalic acid, 0.34 mol (45.94 mol %) of 4-hydroxybenzoic acid, 0.16 mol (21.62 mol %) of t-butylhydroquinone, 0.04 mol (5.41 mol ~) of 4,4'-di(p-hydroxyphenoxy)diphenyl sulfone and 0.86 mol of acetic anhydride are reacted as in Example 1. DSC
measurements indicate a glass transition temperature of 165C. The intrinsic viscosity is 0.93 dl/g. The poly-mer can be processed from the melt at T > Tg, in particu-lar at T 2 200C.
Claims (12)
1. A wholly aromatic polyether ester which forms a liquid-crystalline fiber-forming melt below 300°C and is composed of:
a) not less than 10 mol % of repeat units of the formula (I):
(I) b) a molar amount equivalent to the total amount of components c) and d) of repeat units of the formula (II):
(II) c) from 5 to 20 mol % of repeat units of the formula (III):
(III) and d) from 10 to 30 mol % of repeat units of the formula (IV):
(IV) the molar proportions of components a), b), c) and d) adding up to 100 mol %.
a) not less than 10 mol % of repeat units of the formula (I):
(I) b) a molar amount equivalent to the total amount of components c) and d) of repeat units of the formula (II):
(II) c) from 5 to 20 mol % of repeat units of the formula (III):
(III) and d) from 10 to 30 mol % of repeat units of the formula (IV):
(IV) the molar proportions of components a), b), c) and d) adding up to 100 mol %.
2. A wholly aromatic mesomorphic polyether ester as claimed in claim 1, which contains from 10 to 15 mol % of component c) and from 15 to 25 mol % of component d).
3. A wholly aromatic mesomorphic polyether ester as claimed in claim 1, which further contains one or more repeat units selected from the group consisting of:
e) repeat units of the formula (V):
(V) f) repeat units of the formula (VI):
(VI) and g) repeat units of the formula (VII):
(VII) where R is methyl, phenyl or chlorine, and n is 1, 2 or 3, the molar proportion of components d), e), f) and g) adding up to 10 to 30 mol %.
e) repeat units of the formula (V):
(V) f) repeat units of the formula (VI):
(VI) and g) repeat units of the formula (VII):
(VII) where R is methyl, phenyl or chlorine, and n is 1, 2 or 3, the molar proportion of components d), e), f) and g) adding up to 10 to 30 mol %.
4. A wholly aromatic mesomorphic polyether ester as claimed in claim 3, wherein the molar proportions of the components of the formulae (V), (VI) or (V) and (VI) are from 5 to 10 mol %.
5. A wholly aromatic mesomorphic polyether ester as claimed in claim 3 or 4, wherein the molar proportion of component (VII) is from 5 to 20 mol %.
6. A wholly aromatic mesomorphic polyether ester as claimed in claim 1, 2 or 3, which has a glass transition temperature Tg of ? 150°C.
7. A process for preparing polyether esters as claimed in claim 1 comprising reacting the monomers in a single stage in the form of underivatized hydroxy and carboxy compounds in the molar ratios recited in claiml in the presence of excess fatty acid anhydride at elevated temperatures ranging from 150 to 350°C, and distilling fatty acid anhydride and fatty acid out of the reaction mixture.
8. A process as claimed in claim 7, where.in the wholly aromatic polyether ester is postcondensed in the solid phase at 150-250°C.
9. A fiber prepared from a wholly aromatic polyether ester as claimed in claim 1, 2 ou 3.
10. A film prepared from a wholly aromatic polyether ester as claimed in claim 1, 2 or 3.
11. A molding prepared from a wholly aromatic polyether ester as claimed in claim 1, 2 or 3.
12. A surface coating material as prepared from a wholly aromatic polyether ester as claimed in claim 1, 2 or 3.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3542813A DE3542813A1 (en) | 1985-12-04 | 1985-12-04 | FULLY FLAVORED POLYETHERESTERS, THEIR PRODUCTION AND USE |
| DEP3542813.9 | 1985-12-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1268892A true CA1268892A (en) | 1990-05-08 |
Family
ID=6287560
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000524449A Expired - Lifetime CA1268892A (en) | 1985-12-04 | 1986-12-03 | Wholly aromatic polyether esters and the preparation thereof |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0225539B1 (en) |
| JP (1) | JPS62132922A (en) |
| CA (1) | CA1268892A (en) |
| DE (2) | DE3542813A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9567463B2 (en) | 2011-09-30 | 2017-02-14 | Basf Se | High-strength blends based on polyarylene ethers |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4664972A (en) * | 1986-04-23 | 1987-05-12 | E. I. Du Pont De Nemours And Company | Optically anisotropic melt forming aromatic copolyesters based on t-butylhydroquinone |
| DE3937107A1 (en) * | 1989-11-07 | 1991-05-08 | Akzo Gmbh | MOLDED PART FROM FOAM AND ITS PRODUCTION |
| GB0606050D0 (en) * | 2006-03-27 | 2006-05-03 | Smith & Nephew | Polymer compositions and devices |
| EP2574637A1 (en) | 2011-09-30 | 2013-04-03 | Basf Se | Highly stable blends based on polyarylene ethers |
| US20240294757A1 (en) | 2021-07-16 | 2024-09-05 | Basf Se | Thermoplastic molding composition with high temperature resistance comprising a polyphenylene sulfide |
| CN117715985A (en) | 2021-07-16 | 2024-03-15 | 巴斯夫欧洲公司 | Thermoplastic molding compositions with high temperature resistance comprising thermotropic polymers |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4196275A (en) * | 1977-12-16 | 1980-04-01 | Owens-Illinois, Inc. | Thermoplastic polyesters prepared from bis(4-β-hydroxyethoxyphenyl)sulfone |
| DE3338805A1 (en) * | 1983-10-26 | 1985-05-15 | Basf Ag, 6700 Ludwigshafen | FULLY FLAVORED POLYESTER |
-
1985
- 1985-12-04 DE DE3542813A patent/DE3542813A1/en not_active Withdrawn
-
1986
- 1986-11-19 JP JP61274268A patent/JPS62132922A/en active Pending
- 1986-11-25 DE DE8686116322T patent/DE3664777D1/en not_active Expired
- 1986-11-25 EP EP86116322A patent/EP0225539B1/en not_active Expired
- 1986-12-03 CA CA000524449A patent/CA1268892A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9567463B2 (en) | 2011-09-30 | 2017-02-14 | Basf Se | High-strength blends based on polyarylene ethers |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3664777D1 (en) | 1989-09-07 |
| DE3542813A1 (en) | 1987-06-11 |
| JPS62132922A (en) | 1987-06-16 |
| EP0225539A1 (en) | 1987-06-16 |
| EP0225539B1 (en) | 1989-08-02 |
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