Patent GB-991936-A (GB)
Title: Chemical products, including chemically modified polymeric materials and processes for preparation thereof
IPC: C07C317/18
Filed: 1961-07-10
Abstract: Compounds of formula ROCH2CH2SO2M where M is ROCH2CH2- or (ROCH2CH2 SO2)n-1Q-, where R is hydrogen or C1-4 alkyl, Q is an organic radical of valence n, e.g. an alkyl, aromatic, or alkylaromatic radical, and n is 2 to 4, may be prepared by reacting 2-mercaptoethanol with the corresponding halo-substituted compounds X-Q-X, wherein X is halogen, oxidizing with hydrogen peroxide and etherifying if necessary. Other methods are (a) reacting a polymercaptan HSQSH with ethylene halohydrin in the presence of alkali and oxidizing the thioether, (b) reacting an alkali salt of a polyfunctional sulphinic acid, e.g. NaSO2QSO2Na with ethylene halohydrin XCH2CH2OH, (c) reacting a sulphone halide XCH2CH2SO2- and an alcohol ROH in the presence of an alkaline catalyst, (d) oxidizing the corresponding alkoxyethyl sulphides (ROCH2CH2S-), and (e) by addition of a vinyl sulphone compound (CH2=CHSO2-) to an alcohol ROH in the presence of an alkaline catalyst.  Also, ethers containing the grouping ROCH2CH2SO2- can be prepared by reacting a hydroxyethyl sulphone with an alcohol (ROH) in the presence of an alkaline catalyst. In examples, 2-mercaptoethanol is reacted with (I) dichlorethyl ether, (II) ethylene dichloride, (III) 1,4-di-chlorobutane, (IV) a ,a 1-dichloroxylene, (V) triethylene glycol dichloride, (VIII) propylene dichloride and (IX) 1,2,3-trichloropropane, and the products oxidized with hydrogen peroxide to the corresponding sulphones. In examples, (X) bis-b -hydroxyethyl sulphone is etherified with butanol to give the dibutyl ether and p-oxathiane-4,4-dioxide as by-product and (XI) divinyl sulphone is reacted with a solution of sodium in methanol to give di-(b -methoxyethyl) sulphone.ALSO:Soluble polymeric materials containing a plurality of free hydroxyl groups or active hydrogen atoms are treated in the presence of an alkaline compound with polyfunctional sulphones of formula ROCH2CH2SO2M, where M is ROCH2CH2- or (ROCH2CH2SO2)n-1Q-, where R is hydrogen or an alkyl group containing 1 to 5 carbon atoms, Q is an organic radical of valence n and n is 1 to 3.  Specified polymeric materials are cellulose, cellulose esters, polyvinyl alcohol, starch, polyamines, polyamides and keratins.  Specified alkaline compounds are alkali metal hydroxides, bicarbonates, carbonates, acetates, phosphates, silicates and borates, quaternary ammonium hydroxides and tertiary amines.  The polymeric material, which may be in the form of a textile fabric, may be contacted with the sulphone before or after contacting with the alkaline compound. Many suitable sulphones are specified and examples describe the treatment of (XII) cotton fabric impregnated with polyvinyl alcohol and (XIII) cotton fabric impregnated with starch with bis-b -hydroxyethyl sulphone.ALSO:The crease resistance, crease recovery, resilience and dimensional stability of textile fabrics are improved by treating fabrics comprising or impregnated with soluble polymeric materials containing free hydroxyl groups or active hydrogen atoms in the presence of an alkaline compound with polyfunctional sulphones of formula ROCH2CH2SO2M where M is ROCH2CH2- or (ROCH2CH2SO2)n-1 Q- where R is hydrogen or an alkyl group containing 1 to 5 carbon atoms, Q is an organic radical of valence n and n is 1 to 3. Specified polymeric materials are cellulose, cellulose esters, polyvinyl alcohol, starch polyamines, polyamides and keratins. Specified alkaline compounds are alkali metal hydroxides, bicarbonates, carbonates, acetates, phosphates, silicates and borates, quaternary ammonium hydroxides and tertiary amines.  The fabrics may be contacted with the sulphones before or after contacting with the alkaline compound, and the treated fabric cured at elevated temperature.  Many suitable sulphones are p  specified and examples describe the treatment of (XII) cotton fabric impregnated with polyvinyl alcohol and (XIII) cotton fabric impregnated with starch with bis b -hydroxyethyl sulphone.