NOVEL COMB COPOLYMER AND PROCESS FOR THE PREPARATION THEREOF

摘要

A comb copolymer having a backbone of 2-acrylamido-2-methylpropanesulfonic acid or a derivative thereof, with grafted lateral side segments of poly(N-alkylacrylamide) or poly(N,N-dialkylacrylamide), is provided. A process for the preparation of the comb copolymer includes reacting a compound of formula (II) with a compound of formula (III) in a (tert-butanol)-water mixture, to obtain a poly(N-alkylacrylamide) or poly(N,N-dialkylacrylamide) telomere of formula (I); reacting in tert-butanol the telomer of formula (I) with an acid chloride of formula (IV) to obtain a solution of the macromonomer of formula (V); and copolymerising in tert-butanol the macromonomer of formula (V) with an ammonium salt of 2-acrylamido-2-methylpropanesulfonic acid.

主权项

1. A method for the preparation of a comb copolymer, the comb copolymer comprising a backbone comprising 2-acrylamido-2-methylpropanesulfonic acid or a derivative thereof, with grafted poly(N-alkylacrylamide) or poly(N,N-dialkylacrylamide) side segments, the method comprising the following successive stages:
(a) reaction of a compound of formula (II):
CH2═C(R2)—C(═O)—N(R3)(R4)  (II)in which
R2 represents a hydrogen atom or a methyl group, R3 represents a hydrogen atom or a linear or branched alkyl radical comprising from 1 to 4 carbon atoms, and R4, which is identical to or different from R3, represents a linear or branched alkyl radical comprising from 1 to 4 carbon atoms, with a chain-limiting compound of formula (III):
Z—R1—NH2  (III)in which
R1 represents a divalent radical comprising from 1 to 4 carbon atoms and Z represents a functional group capable of acting as radical transfer agent, in the presence of a polymerization initiator, in a tert-butanol/water mixture, to obtain a poly(N-alkylacrylamide) or poly(N,N-dialkylacrylamide) telomer of formula (I):
H2N—R1—Z—{CH2—C(R2)[C(═O)N(R3)(R4)]—}n—H  (I)in which
n represents an integer greater than or equal to 2 and less than or equal to 100 and Z represents a functional group capable of acting as radical transfer agent; optionally (b) isolation and/or of drying of said telomer of formula (I) obtained in stage (a); (c) reaction in tert-butanol of the telomer of formula (I) obtained in stage (a) or optionally in stage (b) with an acid chloride of formula (IV):
CH2═C(R5)—C(═O)—Cl  (IV)in which R5 represents a hydrogen atom or a methyl radical,
in a (IV)/(III) molar ratio of 1 to 10 inclusive, while maintaining the pH of the reaction medium at a value of between 8 and 10, to obtain a solution of a macromonomer of formula (V):
CH2═C(R5)—C(═O)NH—R1—Z—{CH2—C(R2)[C(═O)N(R3)(R4)]—}n—H  (V),optionally
(d) isolation and/or of drying of said macromonomer of formula (V) obtained in stage (c); (e) copolymerization in tert-butanol of the macromonomer of formula (V) resulting from stage (c) or from stage (d) with an ammonium salt of 2-acrylamido-2-methylpropanesulfonic acid, and optionally (f) purification of the comb copolymer obtained in stage (e).