Copolymerizable polyalkylene glycol macromonomers, and the preparation and use thereof
View Patent ↗The present invention relates to the preparation of Ω-(dimethylisopropenylbenzylurethane) polyalkylene glycols with α-alkoxy or α-dihydroxy groups and to the use thereof as hydrolysis-stable macromonomers for the dispersion and crosslinking of polymers in which A is C 2 -C 4 -alkylene m is an integer from 5 to 900, and R is C 1 -C 20 -alkyl, C 6 -C 18 -aryl or a radical according to formula 2a, 2b, 2c, 3a, 3b or 3c which is bonded to the terminal oxygen atom of the alkoxy group (A-O) in formula 1 via the valence denoted by *, and in which A is not exclusively C 3 - or C 4 -alkylene.
1. A compound of the formula 1
in which
A is C 2 -C 4 -alkylene
m is an integer from 5 to 900, and
R is a radical according to formula 2a, 2b, 2c, 3a, 3b or 3c
which is bonded to the terminal oxygen atom of the alkoxy group (A-O) in formula 1 via the valence denoted by *, and in which A is not exclusively C 3 - or C 4 -alkylene.
2. A compound of the formula 4
in which A is a C 2 -C 4 -alkylene group and m is an integer from 5 to 900, with the proviso that A is not exclusively C 3 - or C 4 -alkylene.
3. A compound of the formula 5
in which A is a C 2 -C 4 -alkylene group and m is an integer from 5 to 900, with the proviso that A is not exclusively C 3 - or C 4 -alkylene.
4. The compound of claim 1 , in which at least 50 mol % of the units -(A-O) m - are ethoxy units.
5. An aqueous dispersion prepared by a process of free-radical polymerization of an olefinically unsaturated compound in the presence of a macromonomer compound selected from the group consisting of the formula 1, 4, 5, and mixtures thereof
wherein A is C 2 -C 4 -alkylene
m is an integer from 5 to 900, and
R is a radical according to formula 2a, 2b, 2c, 3a, 3b or 3c
which is bonded to the terminal oxygen atom of the alkoxy group (A-O) in formula 1 via the valence denoted by *, and in which A is not exclusively C 3 - or C 4 -alkylene, said process comprising mixing the olefinically unsaturated compound in water with the macromonomer compound selected from the group consisting of the formula 1, 4, 5 and mixtures thereof, and triggering the polymerization by adding a free-radical initiator.
6. The aqueous dispersion as claimed in claim 5 wherein the macromonomer compound according to formula 1, 4 or 5 has a cloud point in water of at least 20° C.
7. The aqueous dispersion of claim 5 , in which R is a ketal of glycerol or trimethylolpropane.
8. The aqueous dispersion of claim 5 , in which R is
and the bond to the alkoxy group (A-O) in formula 1, 4 or 5 takes place via the valence denoted by *.
9. The aqueous dispersion of claim 5 , in which -(A-O) m - is a mixed alkoxy group with at least 50 mol % of ethoxy groups.
10. The aqueous dispersion of claim 5 , in which -(A-O) m - is an alkylene oxide block polymer of the formula
—(CH 2 —CH(CH 3 )—O) a —(CH 2 —CH 2 —O) b —R
—(CH 2 —CH 2 —O) b —(CH 2 —CH(CH 3 )—O) a —R
in which
a is a number from 0 to 300, preferably 0 to 80
b is a number from 5 to 300, preferably 5 to 200.
11. The aqueous dispersion of claim 5 , in which -(A-O) m - is an ethoxy chain with 8 to 240 ethoxy units.