Patent GB-587557-A (GB)
Title: Production of synthetic resins
IPC: C08F2/00
Filed: 1944-10-11
Abstract: Tall oil is reacted by heating with a polymeric allyl type alcohol or ester or a monomeric allyl type ester.  Allyl type compounds contain the group <FORM:0587557/IV/1> Alcohols specified are allyl, methallyl, ethallyl, chlorallyl alcohols, butene - ol - 3, pentene - ol - 3, hexene - ol - 3, 3 - methyl - butene - ol - 3, 3 - methyl - pentene - 1 - ol - 3, 2 - methyl - butene - ol - 3, 2 - methylpentene - 1 - ol - 3, 2,3 - dimethyl - butene - 1 - ol - 3, heptene - 1 - ol - 3, 4 - methyl - hexene - 1 - ol - 3, 5 - methyl - hexene - 1 - ol - 3, 4,41 - dimethyl - pentene - 1 - ol - 3, octane - 1 - ol - 3, 6 - methyl - heptene - 1 - ol - 3, 4 - methyl - heptene - 1 - ol - 3, 4,41 - dimethyl - hexene - 1 - ol - 3, 3 - phenyl - propene - 1 - ol - 3, 3 - tolyl - propene - 1 - ol - 3, 3 - xylylpropene - 1 - ol - 3, 4 - phenyl - butene - 1 - ol - 3, 4 - tolyl - butene - 1 - ol - 3, 4 - xylyl - butene - 1 - ol - 3, 3 - naphthyl - propene - 1 - ol - 3, 4 - chloro - butene - 1 - ol - 3, pentadiene - 1,4 - ol - 3, hexene - 1 - yn - 5 - ol - 3, 2 - methyl - pentene - 1 - yn - 4 - ol - 3 and 2,5 - dimethyl - hexadiene - 1,5 - ol - 4, crotyl, tiglyl, and cinnamyl alcohols, 3-chlorbutene - 2 - ol - 1, hexadiene - 2,4 - ol - 1, hexadiene - 2,5 - ol - 1, butadiene - 2,3 - ol - 1, hexadiene - 3,5 - ol - 2, 2 - methyl - hexene - 2 - ol - 1, 2 - methyl - pentene - 2 - ol - 1, 3,7 - dimethyl - octadiene - 2,7 - ol - 1, cyclopentene - 2 - ol - 1 and cyclohexene - 2 - ol - 1.  These alcohols can be polymerized by heating with oxygen, barium, benzoyl or hydrogen peroxides.  Esters specified are allyl formate, acetate, propionate, butyrate, toluate, benzoate and isobutyrate, beta methallyl acetate, beta chlorallyl acetate, beta ethallyl formate, beta phenylallyl acetate, beta methoxyallyl acetate, beta chloromethallyl acetate, allyl salicylate, glycollate, beta chloropropionate and methoxyacetate, beta methylallyl chloracetate, allyl lactate, naphthenate, acetylglycollate, stearate, levulinate, alpha hydroxyisobutyrate, ethoxyformate, naphthoate, allyl esters of hydrogenated abietic acid, beta methallyl chlorobenzoate and butyrate, alpha methallyl acetate, alpha phenylallyl acetate, diallyl malonate, succinate, adipate, maleate, phthalate, diglycollate, dilactate, dihydracrylate, dimethallyl diglycollate, dicrotyl dilactate, allyl type halides, ortho - borates and ortho - silicates, all of which can be polymerized by heating with oxygen or an oxygen yielding catalyst. The reaction may be carried out under nitrogen or carbon dioxide and in the presence of kerosene, high boiling point ethers and coal tar solvents.  Substances which may be admixed with the products are litharge, red lead, manganese dioxide, cobalt, lead and manganese resinates, linoleates and naphthenates, ozone, inorganic and organic peroxides, lead acetate, zinc, manganese and calcium borates, thinners such as methyl isobutyl ketone, plasticisers, dyes and pigments, "Gilsonite" (Registered Trade Mark) rosin, colophony, shellac, copal, dammar gum, pitch, asphalt, protein plastics, cellulose derivatives and phenol-aldehyde, urea-aldehyde alkyd, superpolyamide and superpolyesteramide resins and polymers of vinyl, allyl and methallyl esters of acetic, propionic, butyric oxalic, malonic, succinic, glutaric, citric, tartaric, phthalic, isophthalic, naphthalene dicarboxylic, acrylic and methacrylic acids, of methyl, ethyl and propyl esters of acrylic and methacrylic acids, of styrene, alpha methyl styrene, ethylene, vinyl halides, vinylidene halides, allyl alcohol and allyl halides, polyvinyl acetal and after-chlorinated polyvinyl chloride, polymers of vinyl, allyl, methallyl and cyclohexenyl esters of the ortho acids of silicon and boron, and of the corresponding acids of sulphur and phosphorus, of acrylic and methacrylic polyesters of glycol, diethylene glycol, triethylene glycol, trimethylene glycol and glycerol, polymers of butadiene, pentadienes and hexadienes, and of mono- and di-vinyl acetylene.  The products may be used in coating, impregnating, adhesives for laminates, paints, and films, and may be dissolved in methyl isobutyl ketone.