GB1324055A - Esters of hydroxyphenyl-alkanoic acids and their use as antioxidant stabilizers - Google Patents

Esters of hydroxyphenyl-alkanoic acids and their use as antioxidant stabilizers

Info

Publication number
GB1324055A
GB1324055A GB1324055DA GB1324055A GB 1324055 A GB1324055 A GB 1324055A GB 1324055D A GB1324055D A GB 1324055DA GB 1324055 A GB1324055 A GB 1324055A
Authority
GB
United Kingdom
Prior art keywords
butyl
hydroxyphenyl
bis
tert
propionate
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
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.)
Novartis AG
Original Assignee
Ciba Geigy AG
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
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of GB1324055A publication Critical patent/GB1324055A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
    • C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C08K5/134—Phenols containing ester groups
    • C08K5/1345—Carboxylic esters of phenolcarboxylic acids

Abstract

1324055 Esters of hydroxyphenyl alkanoic acids and their use as antioxidant stabilizers CIBA-GEIGY AG 6 Oct 1971 46514/71 Heading C2 [Also in Division C3] The invention comprises a physical mixture comprising (a) A compound of formula with (b) a compound of formula wherein each of R<SP>1</SP> and R<SP>3</SP> independently represent a methyl, isopropyl, sec. butyl or tert. butyl group; each of R<SP>2</SP> and R<SP>4</SP> independently represent isopropyl, sec. butyl or tert. butyl; and X and Y represent different alkylene groups of from 3 to 18 carbon atoms and having two non- geminal valence bonds. The following mixtures are prepared in the examples: 2,4,4-trimethyl- 1,6 - hexanediol - bis - [3 - (3,5 - di - tert. butyl- 4 - hydroxyphenyl)propionate and 2,2,4-trimethyl - 1,6 - hexanediol - bis - [3,5 - di - tert. butyl-4-hydroxyphenyl) propionate]; erythro. 2 - ethyl - 1,3 - hexane - diol - bis - [3 - (3,5 - ditert. butyl - 4 - hydroxyphenyl) - propionate] and threo - 2 - ethyl - 1,3 - hexanediol - bis- [3 - (3,5 - ditert. butyl - 4 - hydroxyphenyl)- propionate]; 2,2,4 - trimethyl - 1,3 - pentanediol - bis - [3 - (3,5 - di - tert. butyl - 4 - hydroxyphenyl) - propionate] and 2,2- dimethyl - 1,3- hexanediol - bis - [3 - (3,5 - di - tert. - butyl - 4- hydroxyphenyl)-propionate]; a mixture of 2,2,4- and 2,4,4 - trimethyl - 1,6 - hexane diol - bis- [3 - (3 - methyl - 4 - hydroxy - 5 - tert. butylphenyl)-propionates]; a mixture of the 2,2,4- and 2,4,4 - trimethyl - 1,6 - hexane diol - bis- [3 - (3,5 - diisopropyl - 4 - hydroxyphenyl)- propionates; a mixture of 2,2,4- and 2,4,4-trimethyl - 1,6 - hexane diol - bis - [3 - (3,5 - disec. butyl - 4 - hydroxy - phenyl) - propionates; 1,2 - propylene glycol bis - [3 - (3,5 - di - tert.- butyl - 4 - hydroxyphenyl) - propionate] and 1,6 - hexane diol bis - [3 - (3,5 - di - tert. butyl- 4 - hydroxyphenyl) - propionate]; 1,12 - octadecanediol - bis[3 - (3,5 - di - tert - butyl - 4- hydroxyphenyl) - propionate] and 1,9-nonanediol - bis - [3 - (3,5 - di - tert. butyl - 4 - hydroxyphenyl) propionate. The above mixtures can be used as stabilizers against thermooxidative decomposition, for organic materials such as polymers obtained fom polyolefines, polycarbonates, polyamides, polyesters, polyacetals and polyurethanes; mineral oils; animal and vegetable oils, fats and waxes; and natural polymers such as rubbers. Examples 8 and 9 demonstrate the stabilization of polypropylene polymer and synthetic rubber respectively. In Examples 11 and 12 polyamide 6 and polyurethane is stabilized by the above mixtures. Examples 13 and 14 illustrate the stabilization of a homo-polyacetal and a polymethylmethacrylate polymer.
GB1324055D 1971-10-06 1971-10-06 Esters of hydroxyphenyl-alkanoic acids and their use as antioxidant stabilizers Expired GB1324055A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4651471 1971-10-06

Publications (1)

Publication Number Publication Date
GB1324055A true GB1324055A (en) 1973-07-18

Family

ID=10441550

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1324055D Expired GB1324055A (en) 1971-10-06 1971-10-06 Esters of hydroxyphenyl-alkanoic acids and their use as antioxidant stabilizers

Country Status (1)

Country Link
GB (1) GB1324055A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0006745A1 (en) * 1978-06-26 1980-01-09 Uniroyal, Inc. Nitro-containing esters of a substituted phenylpropionic acid, compositions containing them as stabilizing agent against oxidative degradation, and stabilizer compositions
US4267358A (en) * 1980-03-13 1981-05-12 Borg-Warner Corporation Phenolic ester inhibitor
JPS61285253A (en) * 1985-06-13 1986-12-16 Mitsui Petrochem Ind Ltd Polyamide composition
US6815555B2 (en) 2001-09-26 2004-11-09 Theravance, Inc. Substituted phenol compounds useful for anesthesia and sedation

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0006745A1 (en) * 1978-06-26 1980-01-09 Uniroyal, Inc. Nitro-containing esters of a substituted phenylpropionic acid, compositions containing them as stabilizing agent against oxidative degradation, and stabilizer compositions
US4267358A (en) * 1980-03-13 1981-05-12 Borg-Warner Corporation Phenolic ester inhibitor
JPS61285253A (en) * 1985-06-13 1986-12-16 Mitsui Petrochem Ind Ltd Polyamide composition
US6815555B2 (en) 2001-09-26 2004-11-09 Theravance, Inc. Substituted phenol compounds useful for anesthesia and sedation
US7226946B2 (en) 2001-09-26 2007-06-05 Theravance, Inc. Substituted phenol compounds useful for anesthesia and sedation

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee