Abstract This invention is concerned with monoethylenically unsaturated acid ester monomers, such as those of acrylic or methacrylic acid, containing a quaternary ammonium halide group having a substituent on the quaternary nitrogen atom of the formula CH2CH(OH)CH2X wherein X is chlorine, bromine or iodine. It is also concerned with addition polymers of such monomers, and methods of producing the monomers and polymers. The monomers and polymers are stable at acid pH values, although capable of reacting with other reactants for the hydroxyl and/or halide group. At alkaline pH values, they become self-reactive and the polymers crosslink themselves by slow reaction at room temperature. However, the reaction becomes quite rapid on heating.
A compound of the formula wherein R is hydrogen or methyl and Y is an anion.
Claim 2
Dependent Claim
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A compound as defined in claim 2 in which Y is a halogen ion.
Claim 3
Dependent Claim
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A monomeric material comprising a predominant amount of a compound of claim 1 and a compound of the formula wherein R, A, and Y are as defined in claim 1, the latter compound being present in an amount up to about one-third the weight oF the former.
Claim 4
Dependent Claim
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A polymer of a compound of claim 1.
Claim 5
Dependent Claim
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A polymer of a compound of claim 2.
Claim 6
Dependent Claim
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A polymer of a compound of claim 3.
Claim 7
Dependent Claim
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A copolymer of (1) about 0.25 to 99.5 percent by weight of a compound of claim 1 with (2) with at least one other monoethylenically unsaturated monomer having a group of the formula
Claim 8
Dependent Claim
104 words
A method of preparing a compound as defined in claim 1 which comprises reacting, in an aqueous medium at a pH in the range of about 2 to 6, an epihalohydrin at room temperature to 80*C. with an amine salt of the formula H2C C(R)C(O)O-A-N(CH3)2.HY wherein R is hydrogen or methyl, X is chlorine, bromine, or iodine, and A is a (C2-C6) alkylene group having at least two carbon atoms in a chain between the adjoined O and N atoms or A may be a polyoxyethylene group of the formula (CH2CH2O)xCH2CH2 wherein x is 1 to 11 or more, and Y is an anion.