Patent GB-628477-A (GB)
Title: Improvements in compositions containing cellulose esters and ethers
IPC: C07F9/12
Filed: 1946-09-12
Abstract: A composition of matter having a basis of a cellulose ester or ether and containing as a softener or plasticizer, a halogenated organic phosphoric acid ester other than tri-parachlorphenyl phosphate of the general formula <FORM:0628477/IV (a)/1> wherein R represents an alkyl group, X is halogen, n is 0, 1 or 2, and m is an integer of at least 1, said compounds having a meta- and/or para-halogen substituent. The cellulose derivative may be cellulose-acetate, lactate, nitrate, propionate, butyrate, acetate-propionate, and acetate-butyrate or ethyl or benzyl cellulose.  Stabilizers such as calcium lactate may be incorporated in the compositions.  In examples 1, 2 and 3, tri-(2 p  : 4-dichlorophenyl)-, tri-(4-chloro-meta cresyl)- and tri-(4-chloro-2 : 3-dimethylphenyl)-phosphate are mixed with cellulose esters and ethers.  U.S.A. Specification 1,985,771 is referred to.  The Specification as open to inspection under Sect. 91 includes the use of tri-parachlorphenyl phosphate for the above purpose. It also states that the above phosphoric acid esters including tri-parachlorphenyl phosphate are useful as plasticizers in plastic compositions containing synthetic resins, and also as softeners and modifiers for synthetic rubber and for polymeric compounds such as polyvinyl chloride and copolymers of vinyl chloride and vinyl acetate.  This subject-matter does not appear in the Specification as accepted.  Reference has been directed by the Comptroller to U.S.A. Specification 1,985,771.ALSO:Phosphoric acid esters of the general formula (other than tri-parachlorphenyl phosphate) <FORM:0628477/IV (b)/1> wherein R represents an alkyl group such as methyl, ethyl, propyl, butyl, isobutyl, tertiary butyl or amyl, X represents a halogen, n is 0, 1 or 2 and m is an integer of at least 1, said compounds having a meta- and/or para-halogen substituent, are prepared by reacting a phosphorus oxyhalide, e.g. phosphorus oxychloride, with a phenol containing a meta- and/or parahalogen substituent at an elevated temperature.  The phenyl group may also contain a halogen in the ortho position.  The reaction may be effected in the presence of a catalyst, e.g., in the presence of anhydrous magnesium chloride at a temperature not exceeding 225 DEG C. Suitable phenols mentioned are 4-chloro-meta-cresol, chloro-xylenols, dichloro-phenols, dichlorocresols, or dichloro-xylenols containing chlorine in the meta and/or para position.  Mixtures of the suitable phenols may also be used to form a complex phosphoric acid ester.  In examples 1, 2 and 3, the following phosphoric acid esters are prepared: tri-(2 : 4-dichlorophenyl)-phosphate, tri-(4-chloro-meta-cresyl)-phosphate and tri-(4-chloro-2 : 3-dimethyl-phenyl)-phosphate.  U.S.A. Specification 1,985,771 is referred to.  The Specification as open to inspection under Sect. 91 refers to the preparation of tri-parachloro-phenyl phosphate by the above method.  This subject-matter does not appear in the Specification as accepted.  Reference has been directed by the Comptroller to U.S.A. Specification 1,985,771.