Phosphorylated alkylphenol/phenol ester mixtures

Abstract

Phosphorylated alkylphenol/phenol ester mixtures in which the weight ratio of the alkyl moiety to the phenol moiety ranges from 0.05 to about 0.65, and the number of carbon atoms per alkyl moiety ranges from 3 to 16, preferably from 3 to 12, which mixtures have satisfactory viscosity range and impart to polymeric materials and especially to polyvinylchloride plasticized therewith good light and heat stability; a process for producing such phosphorylated alkylphenol/phenol ester mixtures; and polymeric materials plasticized therewith. .Iadd.

We claim: 
     
       1. A triaryl phosphate composition consisting essentially of a phosphorylated . .alkylphenol/phenol.!. .Iadd.isopropyl phenol/phenol .Iaddend.ester mixture wherein the weight ratio of the . .alkyl.!. .Iadd.isopropyl .Iaddend.moiety to phenol moiety ranges from 0.05 to about 0.65 . .and the number of carbon atoms per alkyl moiety ranges from 3 to 16.!. which ester is prepared by steps comprising: (a) alkylating at a temperature of from about 15° to 250° C in the presence of a Lewis acid or a Bronsted acid as catalyst, phenol . .with an alkylating agent selected from the group consisting of alkyl halides in which the alkyl group is a C 1  to C 6  straight- or branched-chain alkyl or a C 6  to C 12  cycloalkyl, C 1  to C 6  alkanols, and C 3  -c 16  olefins,.!. with propylene to obtain an . .alkylated phenol.!. .Iadd.isopropyl phenol/phenol .Iaddend.reaction mixture .Iadd.having 0.05 to about 0.65 by weight of isopropyl moiety per phenol moiety.Iaddend., and   (b) reacting at a temperature of from about 15° to 250° C. in the presence of a Lewis acid as catalyst.Iadd., .Iaddend.said . .alkylated phenol.!. .Iadd.isopropyl phenol/phenol .Iaddend.reaction mixture with a phosphorylating agent selected from the group consisting of phosphorous oxychloride, phosphorous oxybromide and phosphoric acid. . .   
     
     
       2.  A composition as defined in claim 1, wherein the alkyl moiety is a t-butyl moiety..!. . .3. A composition as defined in claim 1, wherein the 
     
     
        alkyl moiety is an isopropyl moiety..!. 4. A composition as . .claimed.!. .Iadd.defined .Iaddend.in claim 1, wherein the phenol starting material is phenol derived from the decomposition of cumene hydroperoxide, or from the sulphonation of benzene, and is in a form free or substantially free from 
     
     
        alkylated phenols. 5. A composition as claimed in claim 1, wherein the . .proportion.!. .Iadd.weight ratio .Iaddend.of . .alkylating agent.!. .Iadd.alkyl moiety .Iaddend.to phenol .Iadd.moiety .Iaddend.is within the range of from . .10%.!. .Iadd.0.1 .Iaddend.to . .40% by weight based on the weight of the phenol.!..Iadd.0.4.Iaddend.. . .6. A composition as claimed in claim 1, wherein the alkylating agent is propylene, isobutylene 
     
     
        or di-isobutylene..!. 7. The product of claim 1 wherein at least part of the alkylation catalyst is removed from the alkylation reaction mixture prior to phosphorylation. .Iadd. 8. A composition according to claim 1 wherein there is employed 42 parts of propylene per 282 parts phenol. .Iaddend..Iadd. 9. A composition according to claim 1 wherein there is employed 84 parts of propylene per 282 parts phenol. .Iaddend.