Composition containing olefinically unsaturated compounds and hy

Details Composition containing olefinically unsaturated compounds and hy Composition containing olefinically unsaturated compounds and hy

1994-01-11

1995-07-18

Schofer, Joseph L.

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Polymers from only ethylenic monomers or processes of...

526141, 526194, C08F 200

Patent

active

054342309

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION

1. Field of the Invention
This invention relates to a composition containing a radical-polymerizable olefinically unsaturated compound and a hydrazone of an aromatic aldehyde or ketone. The invention also relates to its production and to its use as an adhesive and sealing compound and to its use for the coating and production of plastic moldings. The compositions according to the invention polymerize radically at room temperature.
2. Discussion of Related Art
For curing by peroxides or hydroperoxides, olefinically unsaturated systems require selected initiators or activator systems particularly when the reaction is to be initiated at low temperatures, for example at room temperature or only slightly elevated temperatures. For example, it is known that selected tertiary amine compounds with partial aromatic substitution at the N atom perform such an activating function. Known activators for initiating polymerization, for example with dibenzoyl peroxide, are in particular dimethyl aniline and dimethyl-p-toluidine.
A totally different known class of activators for oxidatively initiating the polymerization of certain unsaturated systems, namely drying oils, are metal compounds--at least partly soluble in the system--of metals which can occur in several valency stages and which accelerate the initiation reaction via intermediately occurring valency shifts on interaction with other components of the system. Metal compounds of such metals which are adequately soluble in organic solvents and/or in binders have long been known as so-called drying agents for the air drying of paints, varnishes and the like based on unsaturated oils. Sufficiently oil-soluble compounds of transition metals which are capable of occurring in several valency stages are particularly suitable for this purpose. The individual components differ considerably in their ability to accelerate hardening. Compounds of cobalt and/or manganese are particularly suitable, although iron also has an accelerating effect on curing. In addition, comparable compounds of other metals, which are also capable of developing several valency stages, may be used, particularly in combination with these highly effective metallic components. A detailed description of such systems can be found, for example, in "Ullmann, Encyklopadie der technischen Chemie", 4th Edition, Vol. 23 (1983), 421 to 424.
U.S. Pat. Nos. 4,010,152 and 4,063,012 describe the (co)polymerization of ethylenically unsaturated monomers, such as vinyl chloride, with selected aliphatic alphahydroperoxy)-azo compounds or salts thereof which, on the basis of the structural formulae provided, may be assigned to the class of hydrazone derivatives and which may be regarded as selected hydrazone peroxides. According to the teaching of the first of these two documents, they are prepared by reaction of alpha-halo-azo compounds with sodium peroxide or hydrogen peroxide in the presence of acid acceptors and are said then to be used to initiate polymerization. The majority of the Examples of this document and the parallel second U.S. patent cited above describe the production of the hydroperoxide compounds by a method which is not explained in detail in the general description of the invention. The particular hydrazone compounds selected are dissolved in a solvent and aerated with a stream of oxygen by passing the oxygen through the solution of hydrazone compounds kept at room temperature or at slightly elevated temperatures. The particular hydroperoxides are obtained in yields of 80% or more and are optionally purified by low-temperature crystallization. The hydroperoxides may be used as initiator systems for the polymerization of, for example, vinyl chloride or unsaturated polyester/styrene resins.
A number of earlier publications is concerned with compounds of this type and with their formation, in particular by autoxidation. In 1914, M. Busch et al. described the autoxidation of hydrazones in Ber. 47 (1914), 3277 to 3291. The alleged formation of the peroxides is formulated here a

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"ullmann, Encyklopaedie der technischen Chemie", 4th Edition, vol. 23 (1983), 421 to 424.
Ber. 47 (1914), 3277 to 3291.
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Houben-Weyl, Bd. 7/26, pp. 1954-1956.

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