GB794229A - Hydroxyaryl-substituted acid-esterified acid esters and method of making the same - Google Patents

Hydroxyaryl-substituted acid-esterified acid esters and method of making the same

Info

Publication number
GB794229A
GB794229A GB11683/56A GB1168356A GB794229A GB 794229 A GB794229 A GB 794229A GB 11683/56 A GB11683/56 A GB 11683/56A GB 1168356 A GB1168356 A GB 1168356A GB 794229 A GB794229 A GB 794229A
Authority
GB
United Kingdom
Prior art keywords
acid
epoxidized
substituted
esters
ester
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
GB11683/56A
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.)
SC Johnson and Son Inc
Original Assignee
SC Johnson and Son Inc
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 SC Johnson and Son Inc filed Critical SC Johnson and Son Inc
Publication of GB794229A publication Critical patent/GB794229A/en
Expired legal-status Critical Current

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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
    • C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/006—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by oxidation

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Epoxy Resins (AREA)
  • Epoxy Compounds (AREA)

Abstract

Esters are prepared by reacting (1) an hydroxyaryl-substituted acid which is the condensation product of a phenol and an aliphatic keto acid having its carbonyl group adjacent to the terminal carbon atom; and (2) an ester of an alcohol and an aliphatic acid having from 10 to 36 carbon atoms containing at least one radical of the group consisting of hydroxyl or epoxy. Suitable hydroxylated or epoxidized long-chain acid esters are those of vegetable oils or fish oils, e.g. castor oil, oiticica oil, corn oil, cottonseed alcohols as pentaerythritols, glycols, methyl, ethyl and butyl alcohols, or those prepared from e.g. a mixture of phthalic anhydride, soya bean oil acids and glycerol, also the mixed esters of a polylol, a polycarboxylic acid and a long-chain monocarboxylic acid. Suitable hydroxyaryl-substituted acids are the condensation products of levulinic acid and phenol, substituted phenols or mixtures thereof. The phenols may be substituted with alkyl groups or halogens. Examples are given of the preparation of esters from 4,4-bis(4-hydroxyphenol)-pentanoic acid and (1) castor oil, (2) blown castor oil, (3) epoxidized butyl oleate, (4) epoxidized soya bean oil having an equivalent weight to epoxide of 260. Specifications 768,206 and 790,373 are referred to.ALSO:Esters are prepared by reaction of (1) an hydroxyaryl substituted acid which is the condensation product of a phenol and an aliphatic keto acid having its carbonyl group adjacent to the terminal carbon atom, and (2) an ester of an alcohol and an aliphatic acid having from 10-36 carbon atoms containing at least one radical of the group consisting of hydroxyl or epoxy. The ester of the aliphatic acid of 10-36 carbon atoms may be a complex product such as an epoxidized alkyd resin prepared from a mixture of phthalic anhydride soya bean oil acids and glycerol. It may be a mixed ester of a polyol, a polycarboxylic acid and a long chain monocarboxylic acid. In one example an alkyd resin is prepared from glycerol oleic acid and phthalic acid, epoxidized with hydrogen peroxide and is then esterified with 4,4-bis(4hydroxy phenyl) pentanoic acid to give a hard resin having an acid value of 17.1 and a softening point of 80 DEG C. In another example the ester, having an acid value of 13.5, produced by the reaction of 4,4-bis(4-hydroxyphenyl) pentanoic acid and castor oil is condensed with paraformaldehyde in the presence of methyl isobutyl ketone and toluenesulphonic acid, to produce thin films, which on heating give a hard tack-free flexible product. A similar type of product is obtained using epoxidized butyl oleate (equivalent weight to epoxide 410) instead of castor oil. Specifications 768,206 and 790,373 are referred to.
GB11683/56A 1955-07-14 1956-04-17 Hydroxyaryl-substituted acid-esterified acid esters and method of making the same Expired GB794229A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US794229XA 1955-07-14 1955-07-14

Publications (1)

Publication Number Publication Date
GB794229A true GB794229A (en) 1958-04-30

Family

ID=22150444

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11683/56A Expired GB794229A (en) 1955-07-14 1956-04-17 Hydroxyaryl-substituted acid-esterified acid esters and method of making the same

Country Status (1)

Country Link
GB (1) GB794229A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4547583A (en) * 1983-10-05 1985-10-15 Hoechst Aktiengesellschaft Process for esterifying phenol-containing carboxylic acids

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4547583A (en) * 1983-10-05 1985-10-15 Hoechst Aktiengesellschaft Process for esterifying phenol-containing carboxylic acids

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