Patent GB-923065-A (GB)
Title: Esterification products of halogenated aliphatic carboxylic acids
IPC: C08K5/10
Filed: 1959-12-24
Abstract: The invention comprises plasticizers for polyvinyl chloride resins which are the esterification products of one or more mono- or poly-halogenated aliphatic mono- or di-carboxylic acids containing at least 4 carbon atoms with (a) one or more dihydric alcohols containing up to 9 carbon atoms of which the hydroxyl groups are bound to vicinal carbon atoms and only one of the hydroxyl groups is esterified in the esterification product, or with (b) one or more dihydric alcohols as under (a) and one or more mono- or poly-hydric alcohols in which the hydroxyl groups are bound to primary or secondary carbon atoms, said esters containing at least one ester bond (see Group IV(b)).  Specified resins are polyvinyl chloride and copolymers of vinyl chloride and vinyl acetate and vinylidene chloride.  In an example polyvinyl chloride was milled with an esterification product obtained by reacting a polychlorostearic acid successively with ethylene oxide and n-butanol, and formed into a foil in the usual manner, the tensile strength of the foil being compared with that obtained using dioctyl phthalate as plasticizer.ALSO:The invention comprises the esterification products of one or more mono- or polyhalogenated aliphatic mono- or di-carboxylic acids containing at least 4 carbon atoms with (a) one or more dihydric alcohols containing up to 9 carbon atoms of which the hydroxyl groups are bound to vicinal carbon atoms and only one of the hydroxyl groups is esterified in the esterification product, or with (b) one or more dihydric alcohols as under (a) and one or more monohydric or polyhydric alcohols in which the hydroxyl groups are bound to primary or secondary carbon atoms, said esters containing at least one ester bond.  They are prepared by reacting one or more aliphatic mono- or dicarboxylic acids containing at least 4 carbon atoms and one or more halogen atoms and which may contain an olefinic bond with a 1 : 2-epoxy compound containing up to 9 carbon atoms.  If the product of this reaction is only partially esterified it may be further esterified with suitable mono- or poly-hydric alcohols. These reactions may be carried out in the reverse order of succession or simultaneously. Specified acids include the bromo- or preferably chloro-derivatives of n-butyric 2-ethylcaproic, lauric, palmitic, behenic or undecylenic acids or mixtures thereof, tetrachloro-succinic and a :a 1-dichloroadipic acids. Specified 1 : 2-epoxide compounds include 1 : 2-butylene oxide, phenoxypropene oxide, epichlorhydrin and glycidic acid ethyl ester.  Specified mono- or polyhydric alcohols include ethanol, isopropanol, 2-ethylhexanol, octadecanol-(1)-, benzyl alcohol, oleyl alcohol, ethylene glycol, ethylene glycol, monoethyl ether and glycerine and mixtures thereof. The compounds are used as plasticisers in synthetic resin compositions (see Group IV(a)). In examples: (1) a chloro-stearic acid or chlorinated commercial palmnut fatty acid containing 40% of chlorine is reacted with ethylene oxide in a closed apparatus in the presence of sulphuric acid, the excess ethylene oxide is removed by blowing with nitrogen, and the product of the first stage further esterified with methanol; chlorostearic is also reacted in a similar manner with ethylene oxide or cyclohexene oxide and n-butyl alcohol or with a mixture of ethylene and propylene oxides and commercial amyl alcohol; (2) polychlorosebacic acid or chlorinated tallow fatty acid or chlorinated cottonseed oil fatty acid is reacted with ethylene oxide and n-butanol.