Patent GB-757933-A (GB)
Title: Plasticised polymers and copolymers of vinyl chloride and esters for use therein
Inventor: DAZZI JOACHIM
IPC: C07C309/65
Filed: 1954-01-01
Abstract: Polyvinyl chloride and copolymers of vinyl chloride containing at least 70 per cent by weight of vinyl chloride and not more than 30 per cent by weight of an unsaturated monomer copolymerizable with vinyl chloride, e.g. vinyl acetate, vinylidene chloride or methyl methacrylate are plasticized by means of substituted phenyl esters of alkane sulphonic acids having the general formula <FORM:0757933/IV(a)/1> wherein R is an alkyl group having 6 to 9 carbon atoms, X is hydrogen or an alkyl group having 4 to 6 carbon atoms and Y is an alkyl group having 4 to 12 carbon atoms, the total number of carbon atoms in X and Y being from 8 to 12.  The esters are used in amounts of from 5 to 50 per cent by weight of the plasticized composition.  Heat and light stabilizers and other plasticizers may also be present.  Numerous esters are mentioned, e.g. 4-isononylphenyl n-octanesulphonate and di-sec.-amylphenyl n-heptanesulphonate, and their preparation is described (see Group IV (b)).  Examples of plasticised compositions are given and the effect of the esters as plasticisers is compared with that of phenyl octanesulphonate and diisononylphenyl n-heptanesulphonate. Specifications 681,581 and 681,864 are referred to.ALSO:The invention comprises substituted phenyl esters of alkane sulphonic acids of the general formula <FORM:0757933/IV(a)/1> in which R is an alkyl group having 6 to 9 carbon atoms, X is a hydrogen atom or an alkyl group having 4 to 6 carbon atoms and Y is an alkyl group having 4 to 12 carbon atoms, the total number of carbon atoms in X and Y being from 8 to 12.  They may be prepared by reacting together the appropriate substituted phenols and alkane sulphonyl halides, preferably in the presence of an acid acceptor such as inorganic alkali hydroxides and carbonates, NH3 and tertiary organic bases.  An aqueous or inert organic reaction medium may be used.  The esters are preferably derived from n-alkane sulphonyl halides which may be prepared by sulpho-chlorination of a n-alkane, in which case the sulphohalide product is a mixture of straight chain alkanes having an -SO2Cl radical substituted randomwise in the chain, or by reaction of an n-alkane-1-sulphonic acid with thionyl chloride or bromide or PCl5, yielding n-alkane 1-sulphonyl halides. The esters are used as plasticizers for polymers and copolymers of vinyl chloride (see Group IV (a)).  In examples (1) n-octanesulphonyl chloride is added slowly to a stirred mixture of aqueous NaOH and 4-isononylphenol in dioxane yielding 4-isononylphenyl n-octanesulphonate; (2) n-heptanesulphonyl chloride is similarly reacted with di-sec.-amyl phenol in aqueous NaOH; (3) n-heptane sulphonyl chloride is reacted with 4-isononyl phenol as in (1); for the purposes of comparison as plasticizers, phenyl n-octane sulphonate and di-isononyl phenyl n-heptane sulphonate are also prepared.  Many other examples of esters of the invention are given including the decyl phenyl n-nonane sulphonates, the octyl phenyl n-hexane sulphonates, the undecyl phenyl n-octane sulphonates and the (butyl) (hexyl) phenyl n-heptanesulphonates. Specifications 681,581 and 681,864 are referred to.