Patent GB-1108485-A (GB)
Title: Copolymers of monoepoxy alcohols
IPC: C08G65/22
Filed: 1965-05-17
Abstract: The invention comprises copolymers of (A) certain monoepoxyalcohols containing at least two fused cycloaliphatic rings one of which has an oxygen atom attached to vicinal carbon atoms forming an epoxy group with (B) monooxirane compounds of formula <FORM:1108485/C3/1> wherein R is hydrogen, alkyl, haloalkyl, aryl, or, together, the R's form a six-membered cycloaliphatic rign.  The structure of the copolymer may be represented as:- <FORM:1108485/C3/2> where m, a, n and y are integers and X represents the remainder of the monoepoxy alcohol excluding the oxirane group.  The copolymers are formed using as catalyst acids such as Lewis acids, strong mineral acids, saturated sulphonic acids, and tetra-alkyltitanate, or bases such as alkali metal hydroxides, amines, and trimethyl ammonium hydroxide. An inert organic medium may also be used.  The copolymers may be esterified using an aliphatic monocarboxylic acid, such as an aid derived from a natural oil such as castor oil or linseed oil.  The same catalysts may be used as for the copolymerization. Those esterification products having ethylenic unsaturation may be cured using cobalt naphthenate or lead octanoate.  The reaction of the copolymer with polyepoxides is described.  Fillers and pigments may be added to the esterified products.  In Examples 1-12, 4 - oxatetracyclo[6.2.1.02,7 03,5]undecan - 9 -ol i.e. <FORM:1108485/C3/3> is polymerized with (1) didecyl - 4,5 - epoxycyclohexane - 1,2 - carboxylate, (2) 3,4 - epoxycyclohexane carbonitrile, (3) 1,4-dichloro-3,4-epoxybutane, (4) epichlorohydrin, (5), (6), (7) and (8) propylene oxide, (9), (11) butylene-1,2- and 2,3-oxides, (10) styrene oxide and (12) ethylene oxide.  In examples 1-10 the copolymer is then esterified using linseed oil acid, while examples 13-14 describe the esterification of the copolymers of Examples 11-12 using dehydrated castor oil fatty acid.  Uses: varnishes.ALSO:Steel and glass panels are coated with compositions (varnishes) prepared by esterifying the copolymer formed from reacting a mono-epoxy alcohol containing at least two fused cycloaliphatic rings one of which has an oxygen atom attached to vicinal carbon atoms forming an epoxy group with a mono epoxide of formula: <FORM:1108485/B1-B2/1> using an aliphatic mono carboxylic acid, wherein R0, R1, R2 are -OH, -O(R\svO)xH, or oxyalkane polyol, R3, R4 are -OH, -O (R\svO)xH, oxyalkane polyol, -R\svOH, methylene oxyalkane polyol, -(R\svO)x H,-O(R\svO)x R\yFOH, or -R\svO (R\yFO)x R\yGOH, where x is an integer and R\sv, R\yF, R\yG are alkylene, and wherein R is hydrogen, alkyl, haloalkyl, aryl, or, together the Rs form a six-membered cycloaliphatic ring. Typical acids are butanoic, lauric, stearic, octenoic and those derived from natural sources such as castor oil, linseed oil, olive oil and tall oil.  Those esterification products having ethylenic unsaturation may be cured using cobalt naphthenate or lead actanoate.  Preferably, 0.1 to 1.0 carboxy group of the acid per hydroxy group of the copolymer should be employed.  In the examples, 4-oxa tetracyclo [6.21.0.2,7O3,5] undecan-9-ol i.e. <FORM:1108485/B1-B2/2> is reacted with various epoxides and the resultant copolymer esterified with linseed oil acid (exs. 1-10) or dehydrated castor oil fatty acid (exs. 13-14).  A film of the varnish solution is then cured in each example.