Patent GB-627191-A (GB)
Title: Chlorination of anacardiac phenols
IPC: C07C37/20
Filed: 1947-08-07
Abstract: A phenolic liquid derived from the Anacardiace  family of plants is treated with free chlorine until it has absorbed 1-150 per cent by weight thereof.  The products, particularly those containing at least 5 per cent of chlorine may be reacted with formaldehyde, trioxymethylene, paraformaldehyde or furfuraldehyde to produce an infusible resin.  Suitable phenolic liquids are cashew nut shell liquid, making nut shell liquid, Japanese lac or constituents of these liquids such as anacardic acid, cardol, anacardol, cardanol, urushiol, ethers of these products or polymers thereof.  Distillates or distillation residues from the raw liquids may also be used. Suitable starting materials are described in U.S.A.  Specifications 2,067,919, 2,128,247, 2,179,059 and 2,181,119.  The temperature of chlorination is kept below 200 DEG  F., e.g. between 70 DEG  and 160 DEG  F. especially in absence of a solvent.  When a solvent, e.g. benzene, toluene, xylene, carbon tetrachloride or monochlorbenzene is p  present chlorination may be conducted at room temperature and the amount of chlorine absorbed is greater.  Some of the chlorinated products may be polymerised.  Several of them are millable with rubber (see Group V), and may be used for brake linings or clutch facings.  The condensation products with aldehydes may also be millable with rubber and are similarly useful for friction elements and also for moulding resins or varnishes.  In an example a resin like product formed by reacting chlorinated cashew nut shell liquid with paraformaldehyde is compounded with sulphur, litharge, and zinc oxide and curved in the shape of a brake band.  In another example, chlorinated cashew nut shell liquid was reacted with furfuraldehyde and the product used to impregnate an asbestos web.  On standing or heating, the liquid impregnant became rubbery and the product could be calendered and pressed to shape.  Chlorinated products may be fully hardened with hexamethylenetetranine and the hardened product comminuted for use as a filler in rubber or similar compositions, particularly for friction elements.  In another example asbestos fibres, chlorinated cashew nut shell liquid, hexamethylene tetramine and cork, barytes or chalk are compounded together and formed into sheets which are hardened by baking.  The chlorinated materials may be mixed with aldehyde to form cold-setting cements, or may be dissolved in petroleum solvents and used for impregnating fabrics which may be used for brake and clutch face linings after treatment with an aldehyde.  The solutions may also be employed as constituents of paints and varnishes.ALSO:A phenolic liquid derived from the Anacordiace  family of plants is treated with free chlorine until it has absorbed 1-150 per cent by weight thereof.  Suitable phenolic liquids are cashew nut shell liquid, marking nut shell liquid, Japanese lac or constituents of these liquids such as anacordic acid, cordanol, cordol, anacordol, urushiol, ethers of these products or polymers thereof.  Distillates or distillation residues from the raw liquids may also be used.  Suitable starting materials are described in U.S.A.  Specifications 2,067,919, 2,128,247, 2,179,059, and 2,181,119.  The temperature of chlorination is kept below 200 DEG F., e.g. 70-160 DEG  F., especially when no solvent is present.  When a solvent, e.g. benzene, toluene, xylene, carbon tetrachloride or monochlorbenzene is present, chlorination may be conducted at room temperature and the amount of chlorine absorbed is greater.  The products may be dissolved in petroleum solvents and used as constituents of paints and varnishes.ALSO:A phenolic liquid derived from the Anacardiaceae family of plants is chlorinated and may then be condensed with an aldehyde (see Group IV (a)).  The products are millable with rubber and may be used with it in the manufacture of brake linings or clutch facings.  Hard solid products obtained by condensation with aldehydes may be comminuted and used as a filler in friction elements in which rubber is employed as the binder.