GB891781A - Improvements in or relating to the production of linear aromatic polyesters - Google Patents

Improvements in or relating to the production of linear aromatic polyesters

Info

Publication number
GB891781A
GB891781A GB10789/57A GB1078957A GB891781A GB 891781 A GB891781 A GB 891781A GB 10789/57 A GB10789/57 A GB 10789/57A GB 1078957 A GB1078957 A GB 1078957A GB 891781 A GB891781 A GB 891781A
Authority
GB
United Kingdom
Prior art keywords
dichloride
diphenyl
bis
propane
dicarboxylic acid
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
Application number
GB10789/57A
Inventor
Andre Jan Conix
Urbain Leopold Laridon
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Gevaert Photo Producten NV
Original Assignee
Gevaert Photo Producten NV
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to DEG24245B priority Critical patent/DE1149533B/en
Priority to NL106246D priority patent/NL106246C/xx
Application filed by Gevaert Photo Producten NV filed Critical Gevaert Photo Producten NV
Priority to GB10789/57A priority patent/GB891781A/en
Publication of GB891781A publication Critical patent/GB891781A/en
Expired legal-status Critical Current

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
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/19—Hydroxy compounds containing aromatic rings
    • C08G63/193—Hydroxy compounds containing aromatic rings containing two or more aromatic rings
    • 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
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/181—Acids containing aromatic rings
    • C08G63/185—Acids containing aromatic rings containing two or more aromatic rings
    • 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
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/199—Acids or hydroxy compounds containing cycloaliphatic rings
    • 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
    • C08G63/78—Preparation processes
    • C08G63/82—Preparation processes characterised by the catalyst used
    • C08G63/87—Non-metals or inter-compounds thereof

Abstract

Linear aromatic polyesters, suitable for the manufacture of films and fibres, are made by condensing a diacid halide of an aromatic dicarboxylic acid having two phenylene rings with a metal phenolate of a bis-phenol, the bis-phenolate being dissolved in water and the diacid halide being dissolved in an organic liquid in which the polyester formed by the reaction is to some extent soluble. Preferably the phenolate is the phenolate of a bis-phenol of formula HO-Ar-R-Ar-OH and the acid halide is the halide of an aromatic dicarboxylic acid of formula HOOC-Ar1-R1-Ar1-COOH wherein each of Ar and Ar1 represents a para- or metaphenylene radical or methyl-substituted para- or metaphenylene radical; and one of R and R1 represents an alkyl-, aryl-, or alkyl- and aryl-substituted methylene group, a halogen substituted methylene group, a halomethyl substituted methylene group, or a carbon atom forming part of a cycloaliphatic ring; and the other of R and R1 also represents such a group or atom or represents a chemical bond, an oxygen atom, a carbonyl group, a sulphonyl group or an alkylene radical. The Specification contains lists of suitable reactants. Preferably the bis-phenolates are formed by dissolving the bis-phenols in aqueous sodium- or potassium-hydroxide solution. The organic solvent may be methylene chloride, di-, tri- or tetra-chloroethane, benzene or toluene. A quaternary ammonium compound is preferably used as catalyst. At the end of the reaction the solution of the polyester in the organic solvent is preferably poured into boiling water to precipitate the polyester. The polyesters are soluble in methylene chloride, chloroform, di-, tri- and tetra-chloroethane, benzene, toluene, dioxane and tetrahydrofurane and may be cast from these solvents into film or fibres. Examples describe the manufacture of polyesters from (1), (2), (5), (10) and (11). Bis-phenol A and the dichloride of di-p-carboxyphenyl-2,2-propane, di-(p-carboxyphenyl) ether, sulphonyl-p,p1-dibenzoic acid, 4,41-dicarboxy-diphenyl-dichloromethane or 1,2-di( -carboxyphenyl) ethane; (3) 4,41-dihydroxy-diphenyl-phenyl methane and the dichloride of 2,2-(4,41-dicarboxydiphenyl/propane; (4) 4,41-dihydroxy-diphenyl-1,1-cyclohexane and the dichloride of 2,2-(4,41-dicarboxydiphenyl) propane; (6) 4,41-dihydroxy-diphenylsulphone and the dichloride of 2,2-(4,41-dicarboxydiphenyl) propane; (7) 2,2-(4,41-dihydroxy-3,31-dimethyldiphenyl) propane and the dichloride of diphenyl-4,41-dicarboxylic acid; (8) 3,3-(4,41-dihydroxydiphenyl) pentane and the dichloride of diphenyl-4,41dicarboxylic acid; (9) 1,1-(4,41-dihydroxydiphenyl)-1-phenylethane and the dichloride of diphenyl-4,41-dicarboxylic acid; (12) 1,1,1-trichloro-2,2-(4,41-dihydroxydiphenyl) ethane and the dichloride of diphenyl ether- 4,41-dicarboxylic acid. Specifications 621,102, 883,312 and U.S.A. Specification 2,035,578 are referred to.
GB10789/57A 1957-04-02 1957-04-02 Improvements in or relating to the production of linear aromatic polyesters Expired GB891781A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DEG24245B DE1149533B (en) 1957-04-02 Process for the production of high polymer linear aromatic polyesters
NL106246D NL106246C (en) 1957-04-02
GB10789/57A GB891781A (en) 1957-04-02 1957-04-02 Improvements in or relating to the production of linear aromatic polyesters

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB10789/57A GB891781A (en) 1957-04-02 1957-04-02 Improvements in or relating to the production of linear aromatic polyesters
GB3028364X 1957-04-02

Publications (1)

Publication Number Publication Date
GB891781A true GB891781A (en) 1962-03-21

Family

ID=26247765

Family Applications (1)

Application Number Title Priority Date Filing Date
GB10789/57A Expired GB891781A (en) 1957-04-02 1957-04-02 Improvements in or relating to the production of linear aromatic polyesters

Country Status (3)

Country Link
DE (1) DE1149533B (en)
GB (1) GB891781A (en)
NL (1) NL106246C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4245082A (en) * 1979-07-09 1981-01-13 E. I. Du Pont De Nemours And Company Polyesters derived from 3,4'-dihydroxy-benzophenones or 3-hydroxy-4'-(4-hydroxyphenyl-)benzophenone and certain aromatic dicarboxylic acids and filaments thereof

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2035578A (en) * 1933-04-01 1936-03-31 Du Pont Synthetic resin
GB621102A (en) * 1947-05-15 1949-04-04 James Gordon Napier Drewitt Improvements in the production of linear polyesters
DE959497C (en) * 1955-03-27 1957-03-07 Bayer Ag Process for the production of thermoplastics

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4245082A (en) * 1979-07-09 1981-01-13 E. I. Du Pont De Nemours And Company Polyesters derived from 3,4'-dihydroxy-benzophenones or 3-hydroxy-4'-(4-hydroxyphenyl-)benzophenone and certain aromatic dicarboxylic acids and filaments thereof

Also Published As

Publication number Publication date
NL106246C (en)
DE1149533B (en) 1963-05-30

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