GB744975A - Improvements in the preparation of linear polyesters of sulphonyl dibenzoic acids - Google Patents
Improvements in the preparation of linear polyesters of sulphonyl dibenzoic acidsInfo
- Publication number
- GB744975A GB744975A GB10243/52A GB1024352A GB744975A GB 744975 A GB744975 A GB 744975A GB 10243/52 A GB10243/52 A GB 10243/52A GB 1024352 A GB1024352 A GB 1024352A GB 744975 A GB744975 A GB 744975A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- specified
- diester
- beta
- sulphonyl
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
-
- 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
- C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
-
- 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
Abstract
Linear polyesters are made either (a) by reacting a sulphonyl dibenzoic acid, an alkyl or a beta-hydroxyethyl diester thereof with an alpha - omega straight chain polymethylene glycol or an ester thereof, if desired in presence of another dicarboxylic acid, e.g. adipic, succinic, sebacic, phthalic, terephthalic, fumaric, maleic or itaconic acid or in presence of diethylene glycol or (b) by heating a beta-hydroxyethyl diester of a sulphonyl dibenzoic acid either alone or with a dicarboxylic acid, e.g. one of those specified above. The sulphonyl dibenzoic acids have the formula <FORM:0744975/IV(a)/1> wherein the carboxyl groups are attached to the benzene nuclei in positions either meta or para to the sulphone group, and wherein the benzene nuclei may contain alkyl substituents. Specified polymethylene glycols are ethylene, propylene, butylene and hexylene glycol. The polyesters have high melting points (above 200 DEG C.) and may be used in the manufacture of sheets, films, coatings, fibres, threads, filaments and moulding plastics. Polyesterification is normally effected by heating at 180-230 DEG C. for about 2-5 hours, then at about 240-290 DEG C. for about 1/2 -2 hours and finally under vacuum (less than 10 mm. of Hg pressure) at 240-290 DEG C. for about 3-8 hours. Catalysts, e.g. alkali or alkaline earth metals or their hydroxides or alkoxides may be used. Examples disclose polyesters obtained by reacting: (4) and (5) the butyl diester of p:p1-sulphonyl dibenzoic acid, ethylene glycol and diethylene glycol; (6) the ethyl diester of m:m1-sulphonyl dibenzoic acid and butylene glycol; (7) the beta-hydroxyethyl diester of p:p1-sulphonyl dibenzoic acid and adipic acid. Specification 620,494 is referred to.ALSO:Sulphonyl dibenzoic acids of formula <FORM:0744975/IV(a)/1> wherein the carboxyl groups are attached to the benzene nuclei in positions either meta or para to the sulphone group, and wherein the benzene nuclei may contain alkyl substituents are made by oxidizing the corresponding meta- or para-dimethyl diphenyl sulphone in the presence of a cobalt or manganese catalyst in a solvent which is substantially inert to oxidation and which contains a lower aliphatic aldehyde as an oxidation promoter, at a temperature of 70-120 DEG C. Specified catalysts are cobalt and manganese acetate; specified solvents are dioxane, acetic acid, propionic acid and butyric acid, and specified aldehydes are acetaldehyde, propionaldehyde, isobutyraldehyde and n-butyraldehyde. Preferably the catalyst is suspended in the solvent, the mixture heated and a mixture of oxygen and aldehyde vapours passed into the mixture. When using a cobalt catalyst, the colour of the solution changes from pink to dark green showing that the catalyst has been activated. Then a solution of the dimethyl diphenyl sulphone is added while the introduction of aldehyde and oxygen is continued. The lower alkyl diesters or the beta-hydroxyethyl diesters of the above acids may be prepared by refluxing the acid with a large excess of lower alcohol or ethylene glycol for a long time. Preferably the beta-hydroxy-ethyl diester is prepared by reacting the acid with ethylene oxide at 80-150 DEG C. in presence of a tertiary amine catalyst (many specified). The reaction is preferably effected in an unreactive liquid medium, e.g. a lower alkanol or 1 : 4-dioxane at 100-200 lb./sq. in. Any mono-ester obtained in the reaction product may be removed by washing with a dilute alkaline solution.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB10243/52A GB744975A (en) | 1952-04-23 | 1952-04-23 | Improvements in the preparation of linear polyesters of sulphonyl dibenzoic acids |
GB27155/53A GB777218A (en) | 1952-04-23 | 1953-10-02 | Improvements in the preparation of linear polyesters |
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB10243/52A GB744975A (en) | 1952-04-23 | 1952-04-23 | Improvements in the preparation of linear polyesters of sulphonyl dibenzoic acids |
US777219XA | 1952-10-03 | 1952-10-03 | |
US777218XA | 1952-10-03 | 1952-10-03 | |
US313061A US2744089A (en) | 1952-10-03 | 1952-10-03 | Linear highly polymeric polyesters from p, p'-sulfonyl dibenzoic acid and pentamethylene or higher glycols |
US313067A US2744095A (en) | 1952-10-03 | 1952-10-03 | Linear polyesters from p, p'-sulfonyl dibenzoic acid condensed with an aliphatic ether glycol |
US313063A US2744091A (en) | 1952-10-03 | 1952-10-03 | Linear polyesters from p, p'-sulfonyl dibenzoic acid plus aliphatic dibasic straight chain acids condensed with a glycol |
US472509A US2744088A (en) | 1954-12-01 | 1954-12-01 | Linear polyesters from p, p'-sulfonyl dibenzoic acid plus aliphatic dibasic straightchain acids condensed with a glycol |
Publications (1)
Publication Number | Publication Date |
---|---|
GB744975A true GB744975A (en) | 1956-02-15 |
Family
ID=27562609
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB10243/52A Expired GB744975A (en) | 1952-04-23 | 1952-04-23 | Improvements in the preparation of linear polyesters of sulphonyl dibenzoic acids |
GB27155/53A Expired GB777218A (en) | 1952-04-23 | 1953-10-02 | Improvements in the preparation of linear polyesters |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB27155/53A Expired GB777218A (en) | 1952-04-23 | 1953-10-02 | Improvements in the preparation of linear polyesters |
Country Status (1)
Country | Link |
---|---|
GB (2) | GB744975A (en) |
-
1952
- 1952-04-23 GB GB10243/52A patent/GB744975A/en not_active Expired
-
1953
- 1953-10-02 GB GB27155/53A patent/GB777218A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
GB777218A (en) | 1957-06-19 |
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