GB721713A - Resinous ethers of alkenyl-phenol/aldehyde condensates - Google Patents

Abstract

A resin is made by etherifying a condensation product derived from an aldehyde and a phenol having an ethylenically unsaturated hydrocarbon chain containing 14-28 carbon atoms attached to its aromatic nucleus. The Specification contains a list of aldehydes and a list of anacardic phenols having the formula (R.C6H3OH.X)n, where R is a hydrocarbon radical of 14-28 carbon atoms containing one or more double bonds, n is 1 or more and X is a hydrogen atom or a hydroxyl, aryloxy, alkoxy, alkenyl, alkyl, acyl, aryl, aralkyl, halogen, sulphhydryl, carboxy, amino, alkamino, dialkamino, acetamino, methylol, cycloalkyl, carbalkoxy, alkenoxy, alkenecarboxy or thiocarboxy group. The etherifying agents (many specified) are alkyl, alkenyl, aralkyl, cycloalkyl, and aryl halides; alkyl and aralkyl sulphates; alkyl and aralkyl benzene sulphonates; and diazomethane. The resinous ethers dissolved in naphtha, or in the case of the low condensates (dimers-tetramers) without a solvent, are used as coating compositions after addition of manganese, lead or cobalt driers. The flexibility of the dried coating may be increased (a) by replacing part of the alkenyl phenol with a long-chain alkyl phenol (e.g. hydrogenated cardanol or wax phenols) containing 14-30 carbon atoms in the alkyl chain; (b) by using a long-chain aldehyde for all or part of the aldehyde in the condensation reaction; or (c) by using a long-chain etherifying agent. The hardness of these films may be increased (a) by replacing part of the alkenyl phenol with phenol or cresols; (b) by using a short-chain etherifying agent; or (c) using 1-2 mols. of aldehyde per mol. of phenol in the condensation reaction along with increased reaction times and temperatures. Skinning of the varnishes is prevented by adding 1 per cent or less of free phenols. The ethers may be plasticized with blown or unblown drying or non-drying oils, e.g. soya bean, linseed, oiticica, perilla, sardine, tung, cotton seed or dehydrated castor. They may be added to semi-drying oils to upgrade them and may be co-blown with semi-drying or drying oils (see Group III). The ethers may be used as plasticizers for phenolformaldehyde resins or natural or synthetic rubbers and may be cross-vulcanized with natural or synthetic rubbers using sulphur or sulphur-containing compounds. They may be co-polymerized with butadiene, styrene, chloroprene, acrylonitrile, isoprene or any combination of these in presence of peroxide or peroxide-redox systems, or sodium to give internally plasticized rubbers. In examples (1) cardanol is condensed with formalin in presence of ammonia to give a low molecular weight condensate which is etherified with diethyl sulphate in presence of sodium hydroxide, toluol and xylol; (2) the condensate of example (1) is etherified with a mixture of allyl chloride and diethyl sulphate in presence of potassium hydroxide, ethanol and butanol; (3) cardanol is condensed with formalin in presence of ammonia and xylol to give a higher molecular weight condensate which is etherified with diethyl sulphate in presence of sodium hydroxide, xylol and butanol; (4) the condensate of example (3) is etherified with a mixture of allyl chloride and diethyl sulphate in presence of potassium hydroxide, ethanol and butanol; (5) and (6) the ether of example (3) is mixed with linseed or soya bean oil and the mixture blown with oxygen.ALSO:A resinous product obtained by etherifying a condensation product of an aldehyde and a phenol having an ethylenically unsaturated hydrocarbon chain containing 14-28 carbon atoms attached to its aromatic nucleus (especially an anacardic phenol) (see Group IV(a)) may be added to semi-drying oils to decrease their gelation and drying times and increase their resistance to soft water, alkali, organic solvents and acids. The resin may be co-blown with drying or semi-drying oils to give oils with better drying properties. In examples (5) A mixture of 14 grams of linseed oil and 6 grams of the ethyl ether of a cardanol-formaldehyde condensate was heated to 100 DEG C. and oxygen was blown through at 180 c.c. per minute. (6) Soya bean oil containing 10-13 per cent of the ethyl ether of a cardanol-formaldehyde condensate was blown with oxygen as in example (5).