Fluorine-containing dispersants for aqueous paints and coating compositions

• US 5,672,673 A
• Filed: 06/17/1996
• Issued: 09/30/1997
• Est. Priority Date: 06/21/1995
• Status: Expired due to Fees

• Current Assignee: Bayer AG
• Original Assignee: Bayer AG
• Inventors: Kirchmeyer, Stephan, Mazanek, Jan, Kasler, Karl-Heinz
• Primary Examiner(s): GORR, RACHEL F
• Application Number:
  US08/666,724
• Time in Patent Office: 470 Days
• Field of Search: 528/49, 528/70, 524/591, 524/507, 524/539, 524/500
• US Class Current: 528/70
• CPC Class Codes: C08G 18/283 Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
• CPC Class Codes: C08G 18/2885 containing halogen atoms
• CPC Class Codes: C09D 5/027 Dispersing agents anti-settling agents C09D7/45
• CPC Class Codes: C09D 7/45 Anti-settling agents

Abstract

A method for the preparation of water-soluble polyaddition compounds containing perfluoroalkyl groups by the reaction of a polyisocyanate component A) with a fluorine-containing alcohol component B), hydrophilic monohydric polyether alcohols C), isocyanate-reactive tertiary amines D) and optionally other isocyanate-reactive components E) at an NCO index of 80 to 200, the resulting polyaddition compounds and their use as dispersants for incorporating solid substances into aqueous paints and coating compositions.

Claims

1. A process for the preparing a water-soluble polyaddition compound containing perfluoroalkyl groups which comprises reacting

A) a polyisocyanate component having an average NCO functionality of at least 2.5 and an NCO content of 5 to 50 wt. % with

B) 0.1 to 50 equivalent %, based on the equivalents of isocyanate groups present in component A), of a fluorine-containing alcohol component corresponding to the formula ##STR2## wherein R^f represents a perfluoroalkyl group having 4 to 20 carbon atoms,

R¹ represents an alkyl group having 1 to 6 carbon atoms,

AO represents an alkylene oxide radical having 2 to 10 carbon atoms and

r is a number from 1 to 3,

C) 5 to 90 equivalent %, based on the equivalents of isocyanate groups present in component A), of a monohydric alcohol component containing one or more monohydric polyether alcohols which have a number average molecular weight of 150 to 5000 and an ethylene oxide content of 50 to 99.5 wt. %, and have been prepared by alkoxylation of a monohydric starter molecule, provided that component C) is present in an amount such that the resulting polyaddition compound contains at least 30 wt. % of ethylene oxide units incorporated via component C),

D) 5 to 80 equivalent %, based on the equivalents of isocyanate groups present in component A), of an amine component containing at least one tertiary amine having a molecular weight of 88 to 250 and containing at least one isocyanate-reactive group and

E) 0 to 40 equivalent %, based on the equivalents of isocyanate groups present in component A), of one or more compounds which contain one or more isocyanate-reactive groups, are different from components B) to D), and have ethylene oxide content of less than 50 wt. % and a number average molecular weight of 32 to 3000,

at an isocyanate index of 80 to 200 to form urethane and optionally urea groups, and optionally reducing any NCO groups present in excess to a maximum content of 1.0 wt. % by means of secondary reactions carried out simultaneously or subsequently to the formation of the polyaddition compound.

2. The process of claim 1 wherein polyisocyanate component A) contains isocyanurate groups, has an average NCO functionality of 3 to 6 and an NCO content of 12 to 24 wt. % and is based on 2,4-diisocyanatotoluene or mixtures thereof with up to 35 wt. %, based on the weight of the mixture, of 2,6-diisocyanatotoluene.

3. The process of claim 1 wherein said polyaddition compound has a fluorine content of 0.7 to 20 wt. %, an ethylene oxide content of 50 to 85 wt. % and a content of tertiary amino groups of 5 to 100 milliequivalents per 100 g of resin solids.

4. The process of claim 2 wherein said polyaddition compound has a fluorine content of 0.7 to 20 wt. %, an ethylene oxide content of 50 to 85 wt. % and a content of tertiary amino groups of 5 to 100 milliequivalents per 100 g of resin solids.

5. A water-soluble polyaddition compound having a fluorine content of 0.5 to 50 wt. %, an ethylene oxide content of 30 to 95 wt. % and a content of tertiary amino groups of 2 to 200 milliequivalents per 100 g of resin solids, wherein said fluorine content is obtained from compounds corresponding to the formula ##STR3## wherein R^f represents a perfluoroalkyl group having 4 to 20 carbon atoms,

R¹ represents an alkyl group having 1 to 6 carbon atoms,

AO represents an alkylene oxide radical having 2 to 10 carbon atoms and

r is a number from 1 to 3.

6. The polyaddition compound of claim 5 wherein said polyaddition compound has a fluorine content of 0.7 to 20 wt. %, an ethylene oxide content of 50 to 85 wt. % and a content of tertiary amino groups of 5 to 100 milliequivalents per 100 g of resin solids.

11. An aqueous paint or coating coating composition containing one or more solid substances and the polyaddition compound of claim 5 as a dispersant.

12. An aqueous paint or coating coating composition containing one or more pigments and the polyaddition compound of claim 5 as a dispersant.

13. An aqueous paint or coating coating composition containing carbon black and the polyaddition compound of claim 5 as a dispersant.

7. A water-soluble polyaddition compound containing perfluoroalkyl groups which is prepared by a process which comprises reacting

A) a polyisocyanate component having an average NCO functionality of at least 2.5 and an NCO content of 5 to 50 wt. % with

B) 0.1 to 50 equivalent %, based on the equivalents of isocyanate groups present in component A), of a fluorine-containing alcohol component corresponding to the formula ##STR4## wherein R^f represents a perfluoroalkyl group having 4 to 20 carbon atoms,

R¹ represents an alkyl group having 1 to 6 carbon atoms,

AO represents an alkylene oxide radical having 2 to 10 carbon atoms and

r is a number from 1 to 3,

C) 5 to 90 equivalent %, based on the equivalents of isocyanate groups present in component A), of a monohydric alcohol component containing one or more monohydric polyether alcohols which have a number average molecular weight of 150 to 5000 and an ethylene oxide content of 50 to 99.5 wt. %, and have been prepared by alkoxylation of a monohydric starter molecule, provided that component C) is present in an amount such that the resulting polyaddition compound contains at least 30 wt. % of ethylene oxide units incorporated via component C),

D) 5 to 80 equivalent %, based on the equivalents of isocyanate groups present in component A), of an amine component containing at least one tertiary amine having a molecular weight of 88 to 250 and containing at least one isocyanate-reactive group and

E) 0 to 40 equivalent %, based on the equivalents of isocyanate groups present in component A), of one or more compounds which contain one or more isocyanate-reactive groups, are different from components B) to D), and have ethylene oxide content of less than 50 wt. % and a number average molecular weight of 32 to 3000, at an isocyanate index of 80 to 200 to form urethane and optionally urea groups, and optionally reducing any NCO groups present in excess to a maximum content of 1.0 wt. % by means of secondary reactions carried out simultaneously or subsequently to the formation of the polyaddition compound.

8. The polyaddition compound of claim 7 wherein polyisocyanate component A) contains isocyanurate groups, has an average NCO functionality of 3 to 6 and an NCO content of 12 to 24 wt. % and is based on 2,4-diisocyanatotoluene or mixtures thereof with up to 35 wt. %, based on the weight of the mixture, of 2,6-diisocyanatotoluene.

9. The polyaddition compound of claim 7 wherein said polyaddition compound has a fluorine content of 0.7 to 20 wt. %, an ethylene oxide content of 50 to 85 wt. % and a content of tertiary amino groups of 5 to 100 milliequivalents per 100 g of resin solids.

10. The polyaddition compound of claim 8 wherein said polyaddition compound has a fluorine content of 0.7 to 20 wt. %, an ethylene oxide content of 50 to 85 wt. % and a content of tertiary amino groups of 5 to 100 milliequivalents per 100 g of resin solids.