GB811758A - Polybenzoxazoles and method of preparing the same - Google Patents
Polybenzoxazoles and method of preparing the sameInfo
- Publication number
- GB811758A GB811758A GB32328/56A GB3232856A GB811758A GB 811758 A GB811758 A GB 811758A GB 32328/56 A GB32328/56 A GB 32328/56A GB 3232856 A GB3232856 A GB 3232856A GB 811758 A GB811758 A GB 811758A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- amino
- hydroxyphenyl
- yield
- methyl
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/22—Polybenzoxazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Polybenzoxazoles are made by heating an amino-hydroxy-phenylalkanoic acid of the general formula <FORM:0811758/IV (a)/1> where R is a divalent hydrocarbon radical, or by heating a compound of the general formula <FORM:0811758/IV (a)/2> where R1 is a divalent hydrocarbon radical or a carbon-to-carbon bond with a substantially equimolecular quantity of a saturated aliphatic dicarboxylic acid or an ester thereof, at a temperature of from 100 DEG to 350 DEG C. in the absence of oxygen. The monomers may be co-condensed with polyamide-forming monomers, e.g. tetramethylene and hexamethylene diamine, if equimolecular quantities of dicarboxylic acids are present. In the examples, polybenzoxazoles are prepared from (i) 3-amino-4-hydroxyhydrocinnamic acid; (ii) 3-(3-amino-4-hydroxy phenyl)-3 methyl butyric acid; (iii) 5 - (3 - amino - 4 - hydroxyphenyl) - 5 - methyl hexonoic acid; (iv) 3,31-dihydroxybenzidine and sebacic acid; (v) 3,31-dihydroxybenzidine and sebacic, azelaic and suberic acid. Specifications 461,236, 461,237, [both in Group IV], and U.S.A. Specification 2,497,248 are referred to.ALSO:Amino-hydroxy phenyl alkanoic acids of the general formula <FORM:0811758/IV (b)/1> where R is a divalent hydrocarbon radicle, and compounds of the general formula <FORM:0811758/IV (b)/2> where R1 is a divalent hydrocarbon radicle or a carbon-to-carbon bond are prepared and used as intermediates in the preparation of polybenzoxazoles (see Group IV (a)). In the examples: (1) 4-hydroxybenzaldehyde is heated with malonic acid in the presence of pyridine to prepare 4-hydroxy cinnamic acid which is reduced to 4-hydroxy hydrocinnamic acid, nitrated with aqueous nitric acid to form 3-nitro-4-hydroxyhydrocinnamic acid which is reduced with hydrogen to yield 3-amino-hydroxyhydrocinnamic acid; (II) methoxybenzene is reacted with methallyl chloride in the presence of sulphuric acid to yield 4-chloro-tertiarybutyl methoxybenzene which is converted by a Grignard reaction to 3-(4-methoxyphenyl)-3-methylbutyric acid from which 3-(4-hydroxyphenyl)-3-methyl butyric acid is derived by reflux with an hydrobromic acid-acetic acid mixture, the resultant acid being nitrated and hydrogenated to yield 3-(3-amino-4-hydroxyphenyl)-3-methylbutyric acid; (III) methoxybenzene is alkylated with 5-methyl-5-hexenenitrile in the presence of hydrogen fluoride to yield 5- (4-methoxyphenyl) - 5 - methyl hexenenitrile which is refluxed with sulphuric acid and reacted with an hydrobromic acid-acetic acid mixture to yield 5-(4-hydroxyphenyl)-5-methylhexanoic acid which is nitrated and reduced with hydrogen to give 5 - (3 - amino - 4 - hydroxyphenyl - 5 - methylhexanoic acid; and (IV) 3,31-dihydroxybenzidine is made by demethylating o-dianisidine with aluminium chloride. Specifications 461,236, 461,237, [both in Group IV], and U.S.A. Specification 2,497,248 are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US811758XA | 1955-10-28 | 1955-10-28 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB811758A true GB811758A (en) | 1959-04-08 |
Family
ID=22162560
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB32328/56A Expired GB811758A (en) | 1955-10-28 | 1956-10-23 | Polybenzoxazoles and method of preparing the same |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB811758A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5998662A (en) * | 1997-09-24 | 1999-12-07 | Siemens Aktiengesellschaft | O-amino (thio) phenolcarboxylic acids and their preparation |
US6310238B1 (en) | 1997-09-24 | 2001-10-30 | Siemens Aktiengesellschaft | O-amino(thio)phenolcarboxylic acids, and their preparation |
-
1956
- 1956-10-23 GB GB32328/56A patent/GB811758A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5998662A (en) * | 1997-09-24 | 1999-12-07 | Siemens Aktiengesellschaft | O-amino (thio) phenolcarboxylic acids and their preparation |
US6096921A (en) * | 1997-09-24 | 2000-08-01 | Siemens Aktiengesellschaft | O-amino(thio)phenolcarboxylic acids, and their preparation |
US6310238B1 (en) | 1997-09-24 | 2001-10-30 | Siemens Aktiengesellschaft | O-amino(thio)phenolcarboxylic acids, and their preparation |
US6437178B2 (en) | 1997-09-24 | 2002-08-20 | Infineon Technologies Ag | O-aminophenolcarboxylic acid and o-aminothiophenolcarboxylic acid |
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