GB590451A - Manufacture of highly polymeric linear esters - Google Patents
Manufacture of highly polymeric linear estersInfo
- Publication number
- GB590451A GB590451A GB18632/45A GB1863245A GB590451A GB 590451 A GB590451 A GB 590451A GB 18632/45 A GB18632/45 A GB 18632/45A GB 1863245 A GB1863245 A GB 1863245A GB 590451 A GB590451 A GB 590451A
- Authority
- GB
- United Kingdom
- Prior art keywords
- glycol
- ester
- magnesium
- terephthalic acid
- ethylene glycol
- 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
- 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
-
- 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
- C08G63/183—Terephthalic acids
-
- 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
- C08G63/40—Polyesters derived from ester-forming derivatives of polycarboxylic acids or of polyhydroxy compounds, other than from esters thereof
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/62—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyesters
-
- 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
Highly polymeric linear esters are prepared by heating a glycol HO(CH2)nOH, where n is an integer between 2 and 10 with a functional derivative of terephthalic acid (other than a low aliphatic ester) to form a glycol ester of terephthalic acid which is then heated at a temperature above its melting point until filaments drawn or extruded from the melt may be cold drawn. Suitable functional derivatives of terephthalic acid are half esters, esters other than low aliphatic esters, acid halides and ammonium or amine salts. Preferably, the hydroxyl component of an ester used has a boiling point below that of the glycol. When using an ester of terephthalic acid, excess glycol is preferably employed, and the displaced alcohol or phenol is removed from the reaction zone, e.g. by distillation. An ester interchange catalyst or mixture of catalysts may be employed, e.g. lithium, sodium, potassium, calcium, beryllium, magnesium, zinc, cadmium, aluminium, chromium, molybdenum, manganese, iron, cobalt, nickel, copper, silver, mercury, tin, lead, bismuth, antimony, platinum, or palladium. The catalyst may be present as powder, chips, shavings, ribbon or wire and in the proportion of .025-.1 per cent on the weight of the terephthalate ester. Alkali, or alkaline earth metals or magnesium may be used as alcoholates formed from the glycol of the reaction mixture or a monohydrin alcohol. Alkali metals may be used as carbonates or borates. Magnesium oxide may be used. When using an acid halide, a diluent and a base, e.g. pyridine, may be present. The second stage of the reaction is preferably performed under reduced pressure. The reaction is preferably carried out in absence of oxygen, e.g. with a stream of inert gas, e.g. nitrogen, passing through the mixture. The mass may be mechanically agitated. The molten polymer is removed from the reaction vessel and formed into blocks, chips, filaments or other shapes. Filaments may be cooled before cold-drawing or cold drawn immediately after formation. Passage through warm or hot water or steam before and/or during cold drawing is helpful. In the examples: (1) diphenyl terephthalate, ethylene glycol and potassium carbonate are heated together in nitrogen at 197 DEG C. for 1 hour, phenol being distilled off. Heating is continued for 30 minutes at 280 DEG C. and then for 5 hours at 1 mm. pressure. Filaments from the melt could be cold drawn into fibres; (2) ethyl or methyl hydrogen terephthalate and ethylene glycol were heated in a stream of nitrogen at 200 DEG C. After 4 hours, a mixture of lithium and magnesium was added and heating continued for 2 hours at 200 DEG C. and then raised to 285 DEG C. After 1 hour, pressure was reduced and heating continued for a further 3 hours; (3) terephthalyl chloride, ethylene glycol, pyridine and chloroform were boiled under reflux for 1 hour, cooled and poured into ether, and the separated oil shaken with hydrochloric acid. The low polymer is heated in nitrogen with magnesium as catalyst at 280 DEG C. with gradual reduction of pressure; (4) in this case, ammonium terephthalate and ethylene glycol are the starting materials; (5) this example uses the salt from triethylamine and terephthalic acid on the one hand and ethylene glycol on the other as starting materials. Specification 578,079 is referred to.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES0175142A ES175142A1 (en) | 1945-07-20 | 1946-09-30 | A PROCEDURE FOR THE OBTAINING OF LINEAR ESTERS OF HIGH POLYMERIZATION |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB930904X | 1945-07-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB590451A true GB590451A (en) | 1947-07-17 |
Family
ID=10734804
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB18632/45A Expired GB590451A (en) | 1945-07-20 | 1945-07-20 | Manufacture of highly polymeric linear esters |
Country Status (6)
Country | Link |
---|---|
BE (1) | BE466774A (en) |
CH (4) | CH270745A (en) |
DE (1) | DE818117C (en) |
FR (1) | FR930904A (en) |
GB (1) | GB590451A (en) |
NL (1) | NL60842C (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2518283A (en) * | 1948-07-29 | 1950-08-08 | Du Pont | Production of polyethylene terephthalate |
DE948086C (en) * | 1951-07-01 | 1956-08-30 | Basf Ag | Process for the production of covering materials |
DE1102132B (en) * | 1956-06-08 | 1961-03-16 | Distillers Co Yeast Ltd | Process for the preparation of di- (2-oxyaethyl) terephthalate |
US3058948A (en) * | 1957-07-19 | 1962-10-16 | Schweizerische Isola Worke | Metal salt-amine complex and process for preparing polyester resin composition therewith |
DE1292398B (en) * | 1958-10-30 | 1969-04-10 | Monsanto Co | Process for the production of high polymer polyesters |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE974160C (en) * | 1952-02-16 | 1960-09-29 | Bayer Ag | Process for the production of high molecular weight polyesters of terephthalic acid |
DE1135660B (en) * | 1955-02-09 | 1962-08-30 | Ici Ltd | Process for the production of high molecular weight polyethylene or polytetramethylene terephthalates |
GB863704A (en) * | 1956-05-18 | 1900-01-01 | ||
ES252134A1 (en) * | 1958-09-29 | 1960-06-16 | Kunoshima Kagaku Kogyo Kabushi | A procedure to obtain polycarbonates (Machine-translation by Google Translate, not legally binding) |
-
0
- DE DENDAT818117D patent/DE818117C/en not_active Expired
- BE BE466774D patent/BE466774A/xx unknown
- NL NL60842D patent/NL60842C/xx active
-
1945
- 1945-07-20 GB GB18632/45A patent/GB590451A/en not_active Expired
-
1946
- 1946-07-19 CH CH270745D patent/CH270745A/en unknown
- 1946-07-19 CH CH270746D patent/CH270746A/en unknown
- 1946-07-19 CH CH254542D patent/CH254542A/en unknown
- 1946-07-19 CH CH270747D patent/CH270747A/en unknown
- 1946-07-20 FR FR930904D patent/FR930904A/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2518283A (en) * | 1948-07-29 | 1950-08-08 | Du Pont | Production of polyethylene terephthalate |
DE948086C (en) * | 1951-07-01 | 1956-08-30 | Basf Ag | Process for the production of covering materials |
DE1102132B (en) * | 1956-06-08 | 1961-03-16 | Distillers Co Yeast Ltd | Process for the preparation of di- (2-oxyaethyl) terephthalate |
US3058948A (en) * | 1957-07-19 | 1962-10-16 | Schweizerische Isola Worke | Metal salt-amine complex and process for preparing polyester resin composition therewith |
DE1292398B (en) * | 1958-10-30 | 1969-04-10 | Monsanto Co | Process for the production of high polymer polyesters |
Also Published As
Publication number | Publication date |
---|---|
CH270745A (en) | 1950-09-15 |
FR930904A (en) | 1948-02-09 |
BE466774A (en) | |
CH270747A (en) | 1950-09-15 |
CH254542A (en) | 1948-05-15 |
NL60842C (en) | |
DE818117C (en) | 1951-08-30 |
CH270746A (en) | 1950-09-15 |
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