Polyureas as rheology control agents

Patent metadata

Field	Value
Publication number	US-9617371-B2
Application number	US-201013395006-A
Country	US
Kind code	B2
Filing date	Sep 3, 2010
Priority date	Sep 8, 2009
Publication date	Apr 11, 2017
Grant date	Apr 11, 2017

Abstract

The invention relates to polyureas having a weight-average molecular weight ranging from 5,000 to 70,000 g/mol, the preparation thereof, and the use thereof as rheology control agents. The invention further relates to rheology control agents containing polyureas and to the use thereof. The invention moreover relates to formulations containing polyureas.

First claim

The invention claimed is:

1. A polyurea of the general formula (I)

wherein:
T is a unit comprising at least four urea groups and has the formula (II)

wherein:
R 3 and R 4 are each identical or different and independently of one another are branched or unbranched polyester, polyether, C 4 -C 22 alkylene, C 3 -C 20 cycloalkylene, C 3 -C 20 cycloalkenylene, C 5 -C 12 arylene or arylalkylene radicals,
Z and W are each identical or different and independently of one another are —NHCOO— or —NH—CO—NH—, and
q is 2-200;
R 1 and R 7 independently of one another are branched or unbranched C 4 -C 32 alkyl, C 3 -C 18 alkenyl, C 2 -C 20 alkynyl, C 3 -C 20 cycloalkyl, C 3 -C 20 cycloalkenyl, C 5 -C 12 aryl or arylalkyl, C m H 2m+1 (O—C n H 2n ) p —(O—CH(C 6 H 5 )—CH 2 ) u —, U—C 6 H 4 —(CH 2 ) s —(O—C n H 2n ) x —(O—CH(C 6 H 5 )—CH 2 ) u —, C m H 2m+1 (O—C n H 2n ) p —(O—CH(C 6 H 5 )—CH 2 ) u —(OOC—C v H 2v ) x —, U—C 6 H 4 —(CH 2 ) s —(O—C n H 2n ) p —(O—CH(C 6 H 5 )—CH 2 ) u —(OOC—C v H 2v ) x —, C 4 -C 32 -hydroxyalkyl, C 4 -C 32 -carboxyalkyl, —C m H 2m C(═O)R 8 —, —C m H 2m COOR 8 —, —C m H 2m C(═O)NR 8 R 9 — or —C m H 2m OC(═O)NR 8 R 9 radicals, it being possible for the radicals to be substituted or unsubstituted, it being possible for the amino groups and/or carboxyl groups to be present in salified or quaternized form, and C m H 2m being a linear or branched alkylene group, and R 8 and R 9 independently of one another are hydrogen, branched or unbranched C 1 -C 32 alkyl, C 3 -C 18 alkenyl, C 2 -C 20 alkynyl, C 3 -C 20 cycloalkyl, C 3 -C 20 cycloalkenyl, C 5 -C 12 aryl or arylalkyl, C 1 -C 32 alkoxyalkyl or C 1 -C 32 acyloxyalkyl groups, where m=0-32, n=2-4, x=0-100, u=0-100, v=1-22, p=0-100, s=0-1, U═H, C 1 -C 12 alkyl or —C 6 H 5 ) 1-4 ,
R 2 and R 6 independently of one another are branched or unbranched C 4 -C 22 alkylene, C 3 -C 20 cycloalkylene, C 3 -C 20 cycloalkenylene, C 5 -C 12 arylene or arylalkylene radicals,
R 5 is a branched or unbranched polyester, polyether, unbranched C 4 -C 22 alkylene, C 3 -C 20 cycloalkylene, C 3 -C 20 cycloalkenylene, C 5 -C 12 arylene or arylalkylene radical,
B and X independently of one another are —O— or —NR 10 — with R 10 is H, branched or unbranched C 1 -C 32 alkyl, C 3 -C 20 cycloalkyl, C 3 -C 20 cycloalkenyl C 5 -C 12 aryl or arylalkyl radicals,
A and Y independently of one another are NR 10 , wherein each R 10 is, independently, H, branched or unbranched C 1 -C 32 alkyl, C 3 -C 20 cycloalkyl, C 3 -C 20 cycloalkenyl, C 5 -C 12 aryl or arylalkyl radicals, and
the weight-average molecular weight being 5000 to 70000 g/mol.

2. The polyurea as claimed in claim 1 , wherein T comprises no urethane groups.

3. The polyurea as claimed in claim 1 , wherein the polyurea has a weight-average molecular weight of 5000 to 12000 g/mol.

4. The polyurea as claimed in claim 1 , wherein the polyurea has a weight-average molecular weight of 10000 to 26000 g/mol.

5. The polyurea as claimed in claim 1 , wherein the polyurea has a weight-average molecular weight of 24000 to 55000 g/mol.

6. The polyurea as claimed in claim 3 , wherein the radicals R 1 and/or R 7 are substituted by polar functional groups and/or comprise polyester groups and/or polyether groups.

7. The polyurea as claimed in claim 1 , wherein the polyurea is present as a solution in at least one solvent and/or vehicle.

8. The polyurea as claimed in claim 1 preparable by
a. the reaction of at least one diisocyanate with at least one component K which has two NCO-reactive groups, in a molar ratio of diisocyanate to component K of (f+1):f with f≧1, to form intermediately an isocyanate-terminated urea having on average two free isocyanate groups in the molecule, and subsequent complete reaction of the free isocyanate groups of the intermediate with at least one component L that is reactive toward isocyanate groups,
or

b. the reaction of at least one diisocyanate with at least one component K which has two NCO-reactive groups, in a molar ratio of diisocyanate to component K of f:(f+1) with f≧1, to form an intermediate having on average two free isocyanate-reactive, terminal groups in the molecule, and subsequent complete reaction of the free isocyanate-reactive groups of the intermediate with at least one monoisocyanate-functional compound,
or

c. the reaction of a mixture of at least one diisocyanate and at least one monoisocyanate-functional compound with at least one component K which has two NCO-reactive groups, in a molar ratio of diisocyanate to component K to monoisocyanate-functional compound of f:(f+1):2 with f≧1,
d. the reaction of a mixture of at least one component K which has two NCO-reactive groups and at least one component L that is reactive toward isocyanate groups with at least one diisocyanate, in a molar ratio of component K to diisocyanate to component L of f:(f+1):2 with f≧1,
where component K has as NCO-reactive groups either two primary amine groups or one primary amine group and one OH group, and component L has at least one primary amine group, one secondary amine group or one OH group.

9. A process for preparing the polyurea as claimed in claim 1 , wherein
a. at least one diisocyanate is reacted with at least one component K which has two NCO-reactive groups, in a molar ratio of diisocyanate to component K of (f+1):f with f≧1, to form intermediately an isocyanate-terminated urea having on average two free isocyanate groups in the molecule, and
the free isocyanate groups of the intermediate are subsequently completely reacted with at least one component L that is reactive toward isocyanate groups,
or

b. at least one diisocyanate is reacted with at least one component K which has two NCO-reactive groups, in a molar ratio of diisocyanate to component K of f:(f+1) with f≧1, to form an intermediate having on average two free isocyanate-reactive, terminal groups in the molecule, and
the free isocyanate-reactive groups are subsequently reacted completely with at least one monoisocyanate-functional compound,
or

c. at least one diisocyanate is mixed with at least one monoisocyanate-functional compound and this mixture is subsequently reacted with at least one component K which has two NCO-reactive groups, in a molar ratio of diisocyanate to component K to monoisocyanate-functional compound of f:(f+1):2 with f≧1,
d. at least one component K which has two NCO-reactive groups is mixed with at least one component L that is reactive toward isocyanate groups and this mixture is subsequently reacted with at least one diisocyanate, in a molar ratio of component K to diisocyanate to component L of f:(f+1):2 with f≧1,
where component K has as NCO-reactive groups either two primary amine groups or one primary amine group and one OH group, and component L has at least one primary amine group, one secondary amine group or one OH group.

10. A rheology control agent comprising at least one polyurea as claimed in claim 1 .

11. The rheology control agent as claimed in claim 10 , wherein the rheology control agent is free from film-forming resins.

12. The rheology control agent as claimed in claim 10 , wherein the fraction of polyurea in a formulation is 0.05% to 10% by weight, based on the total weight of the formulation.

13. The rheology control agent as claimed in claim 12 for rheology control in polar s

Assignees

• Leutfeld Daniela
• Morhenn Bianca
• Eberhardt Marc
• Kober Ina
• Omeis Jürgen
• Bühne Sylvia
• Jacobs Berthold
• Byk Chemie Gmbh

Inventors

• Leutfeld Daniela
• Morhenn Bianca
• Eberhardt Marc
• Kober Ina
• Omeis Jürgen
• Bühne Sylvia
• Jacobs Berthold

Classifications

• C08G18/755

  and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate · CPC title

• C08G18/706

  the liquid medium being water · CPC title

• C08G18/7621

  being toluene diisocyanate including isomer mixtures · CPC title

• C08G18/711

  containing oxygen in addition to isocyanate oxygen · CPC title

• C08G18/283

  Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds · CPC title