Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1998-02-27
1999-05-18
Burn, Brian M.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
560 20, C07C229/00;205/00
Patent
active
059051647
DESCRIPTION:
BRIEF SUMMARY
This invention relates to novel amine compounds, to their preparation, to their use as radiation curing agents in polymerisation processes, and to polymeric products cured by such amine compounds.
Amines, especially tertiary amines, are important curing agents for photoinitiated curing processes. They are used in conjunction with photo-excited species, commonly called photoinitiators, which react with the amines to generate amine-derived radicals which initiate polymerisation.
There are two commercially important aromatic amine curing agents currently available, ethyl-4-(N,N'-dimethylamino) benzoate (EDB) and 2-n-butoxyethyl 4-(dimethylamino) benzoate (BEDB). These are highly effective as curing agents when used in conjunction with thioxanthone initiators, in particular isopropylthioxanthone (ITX). However they suffer the disadvantage that they tend to migrate from the polymer, over time. The surface of the polymer may be spoiled and compounds may migrate into the substrate, which could, for example, be a food or drinks products.
Japanese published patent application 6263814 (Toyo Ink) discloses curing agents obtained by reacting dihydric polyol compounds, for example ethylene glycol, with dimethylaminobenzoic acid. These are used in curable coating compositions said to have reduced odor, and to be free from deterioration from curability. However, in experiments we have found such curing agents to be rather slow in inducing polymerisation; and to migrate from a cured polymer at an unacceptably high rate.
It is an object of the present invention to provide an amine curing agent which is effective in inducing polymerisation and which is effectively retained within the cured polymer. That is to say, its migration from the cured polymer is to be low, or nil.
In accordance with a first aspect of the present invention, there is provided an amine compound of the general formula ##STR2## wherein: each R.sup.1 independently represents an alkyl group; hydroxyl groups of the polyol moiety are optionally alkylated; acyl, nitro, cyano, alkoxy, hydroxy, amino, alkylamino, sulphinyl, alkylsulphinyl, sulphonyl, alkylsulphonyl, sulphonate, amido, alkylamido, alkoxycarbonyl, halocarbonyl and haloalkyl groups.
Suitably, n and m independently represent 1 or 2preferably 1.
Suitably, each Q represents a hydrogen atom.
Suitably, each R.sup.1 represents the same alkyl group.
Suitably, each R.sup.1 represents a C.sub.1-4 alkyl group, preferably methyl.
Suitably, each R.sup.2 represents the same alkyl group.
Suitably, each R.sup.2 represents a C.sub.1-4 alkyl group, preferably methyl.
Suitably, one or each group X includes at least two ether functionalities.
Suitably, each X independently represents a polyalkylene glycol moiety, wherein hydroxyl groups of the moiety are optionally alkylated.
Suitably, each X represents a polyethylene glycol moiety, wherein hydroxyl groups of the moiety are optionally alkylated.
Suitably, one or preferably each, group X represents a polyol moiety which is end-capped by an alkyl group.
Suitably, the alkyl group which end caps the group X is a C.sub.1-4 alkyl group. Preferably, it is a methyl group.
Preferably, one or preferably each group X represents a polyol moiety wherein each hydroxyl group is alkylated.
Preferably, one or each group X is of the general formula --O--(CH.sub.2 --CH.sub.2 --O).sub.z -alkyl where z has a mean value of from 2 to 20, preferably 4 to 15, most preferably 6 to 13 and the alkyl group is suitably a C.sub.1-4 alkyl group, preferably methyl.
Preferably, at least one said group COX is located para to a said dialkylamine group. Where n=m=1, preferably the group COX is located para to the dialkylamine group.
In accordance with a second aspect of the present invention there is provided a process for the preparation of a compound of general formula I, which process comprises alkylation of a corresponding primary amine compound (in which R.sub.1 =R.sub.2 =hydrogen). This may be carried out by reductive alkylation, using the appropriate alkanal.
Such a reaction can be carried out i
REFERENCES:
patent: 4515981 (1985-05-01), Kozo et al.
Chemische Berichte, vol. 117, 1984, Weinheim DE, pp. 1994-1997, XP002010498, E. Bayer et al., "Darstellung von Monound Divinylethern des Tetra (oxyethylens)".
Journal Of The American Chemical Society, vol. 62, 1940, DC US, pp. 3136-3139, XP002010499, J.F. Manning, "Solid Derivatives of Monoalkyl Ethers of Ethylene Glycol and Diethylene Glycol. II", see p. 3137--p. 3138; table II.
Journal Of The American Chemical Society, vol. 62, No. 7, 1940, DC US, pp. 1635-1640, XP002010500, P. Mason et al., "Solid Derivatives of Monoalkyl Ethers of Ethylene Glycol and Diethylene Glycol".
Pharm. Weekbl. (1969), 104(26), 658-70 Coden: PHWEAW, 1969, XP000578904, Buechi, Jakob et al., "Synthesis and antitussive activity of some 3-butoxy-4-amino-benzoic acid esters".
Patent Abstracts Of Japan, vol. 18, No. 668 (C-1289) & JP,A, 06 263814 (Toyo Ink Mfg. Co. Ltd), cited in the application.
Anderson David George
Cullum Neil Richard
Davidson Robert Stephen
Sands Elizabeth
Burn Brian M.
Davis Brian J.
Lambson Fine Chemicals Limited
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