Products obtainable by salt formation from polyamines and the use thereof as dispersing agents for pigments and extenders

• US 6,111,054 A
• Filed: 06/26/1998
• Issued: 08/29/2000
• Est. Priority Date: 07/26/1997
• Status: Expired due to Term

• Current Assignee: BYK-Chemie GmbH (Susanne Klatten, MBA)
• Original Assignee: BYK-Chemie GmbH (Susanne Klatten, MBA)
• Inventors: Orth, Ulrich, Pritschins, Wolfgang, Haubennestel, Karlheinz, Krappe, Udo
• Primary Examiner(s): HAMPTON HIGHTOWER, PATRICIA
• Application Number:
  US09/105,975
• Time in Patent Office: 795 Days
• Field of Search: 528/312, 528/313, 528/220, 528/176, 528/229, 528/322, 528/332, 528/337, 528/336, 252/363.5, 524/801, 524/800, 524/802, 524/813, 524/817, 524/818
• US Class Current: 528/176
• CPC Class Codes: C08G 73/02 Polyamines
• CPC Class Codes: C08G 73/0213 Preparatory process
• CPC Class Codes: C08G 73/0226 Quaternisation of polyalkylene(poly)amines
• CPC Class Codes: C09K 23/14 Derivatives of phosphoric acid
• CPC Class Codes: C09K 23/16 Amines or polyamines

Abstract

The present invention relates to a dispersing agent for pigments or extenders which is obtainable by salt formation from an amine-functional compound by means of an acid,

wherein a polyamine which contains at least three amino groups and which is from the group comprising aliphatic linear polyamines and/or aliphatic branched polyamines and/or modified polyamines, with the proviso that after modification three amino groups which can be converted into salts are still present per molecule, or a mixture of polyamines such as these, is used as the amine-functional compound, and

wherein a substance from the group comprising phosphoric acid esters of general formula: (HO)_3-n PO(OR¹)_n where n=1 or 2, sulphonic acids of general formula HOSO₂ R² and acidic sulphuric acid esters of general formula HOSO₃ R² is used as the acid, wherein R¹ and R² represent an alkyl, aryl or aralkyl radical containing at least 5 C atoms and/or a radical of an oxyalkylated alcohol with a number average molecular weight between 100 and 5000 g/mole and/or a radical containing at least one carboxylic acid ester group and/or a urethane group with a number average molecular weight between 100 and 5000 g/mole, or a mixture of substances such as these, wherein R¹ and R² can be the same or different.

The invention also relates to the use of the dispersing agent and to a method of producing it.

Claims

1. A dispersing agent for pigments or extenders comprising a salt of an amine-functional compound and an acid,

wherein the amine-functional compound contains at least three amino groups and is selected from the group consisting of an aliphatic, linear or branched polyamine, a modified polymine, a homo-, co- or block polymer having amine group substituents or a mixture thereof;

wherein the acid is a phosphoric acid ester of the formula (HO)_3-n PO(OR¹)n where n=1 or 2, a sulphonic acid of the formula HOSO₂ R², a sulphonic acid ester of the formula HOSO₃ R² or a mixture thereof wherein R¹ and R² represent an alkyl, aryl or aralkyl radical containing at least 5 C atoms and/or a radical of an oxyalkylated alcohol with a number average molecular weight between 100 and 5000 g/mole and/or a radical containing at least one carboxylic acid ester group and/or a urethane group with a number average molecular weight between 100 and 5000 g/mole, and R¹ and R² can be the same or different;

wherein the aliphatic linear or branched polyamine is selected from the group consisting of diethylenetriamine, triethylenetetramine, tetraethylenepentamine, penethylenehexamine, hexaethyleneheptamine, a linear condensate of the formula NH₂ -(C₂ H₄ NH)_n -C₂ H₄ -NH₂ where n is greater than 5 up to an integer providing a number average molecular weight of 1 million, a branched (C₂ -C₄) alkylene amine containing tertiary amine groups with a number average molecular weight up to 1 million, a branched poly(C₂ -C₄)alkylene imine containing tertiary amine groups with a number average molecular weight up to 1 million, and any mixture thereof;

wherein, the modified polyamine is selected from the group consisting of a reaction product of an aliphatic linear or branched polyamine with a mono- or polyisocyanate, an epoxy compound, or a cyclic carbonate;

a Michael reaction product of an aliphatic linear or branched polyamine with an α

,β

-unsaturated carbonyl compound or an α

,β

-unsaturated carboxylic ester or an α

,β

-unsaturated nitrile; and

an alkylated or quaternized, aliphatic, linear or branched polyamine or combination thereof, with the proviso that the modified polyamine contains at least three amino groups which are convertable into salt groups;

and wherein the homo-, co- or block polymer is selected from the group consisting of a homo-, co- or block polymer of an aminoalkyl (meth)acrylate, and a homo-, co- or block polymer of an amine or nitrogen heterocycle substituted vinyl compound, the homo-, co- or block polymer having a number average molecular weight up to 1 million.

2. A dispersing agent according to claim 1, wherein the amine-functional compound is the linear condensate and the protons on the nitrogen are replaced by alkyl, aryl and/or aralkyl groups and/or are alkoxylated and/or quaternized.

3. A dispersing agent according to claim 1, wherein the amine-functional compound is a branched poly(C₂ -C₄)alkylene imine having a number average molecular weight of 600-200,000 g/mole.

4. A dispersing agent according to claim 1, wherein the amine-functional compound is a branched poly(C₂ -C₄)alkylene amine.

5. A dispersing agent according to claim 1, wherein the amine-functional compound is a modified polyamine in which 0.5 to 90 mole % of the primary and secondary amino groups of the aliphatic, linear or branched polyamine are converted to reaction product, Michael reaction product or alkylated or quaternized.

6. A dispersing agent according to claim 1, wherein one or more hydrogens in the aliphatic groups of R¹ and R² radicals are replaced by halogen atoms.

7. A dispersing agent according to claim 1, wherein R¹ and R² represent the radical of an oxyalkylated, monoalcohol.

8. A dispersing agent according to claim 1, wherein R¹ and R² represent the radical of an oxyalkylated monoalcohol containing carboxylic and ester- and/or urethane groups.

9. A dispersing agent according to claim 1, wherein R¹ and/or R² constitute a number average molecular weight of 200 to 5000 g/mole.

10. A dispersing agent according to claim 1, wherein the acid further comprises substituents with functional groups which exhibit inert behavior during salt formation.

11. A dispersing agent according to claim 1, wherein the degree of salt formation is defined as the ratio of acid equivalents to amine equivalents and falls with the range from 0.02 to 1.

12. A pigment composition comprising a dispersing agent according to claim 1 and a pigment and/or extender.

13. A dispersible solid comprising powder or fibrous particles coated with a dispersing agent according to claim 1.

14. A dispersible solid according to claim 13, which is a paste.

15. A pigmented lacquer comprising a mixture of a dispersing agent according to claim 1 a lacquer binder vehicle, and a pigment.

16. A pigmented coating on a substrate, comprising a pigmented lacquer according to claim 15 applied to the substrate, and stoved, hardened or crosslinked.

17. A method of producing a dispersing agent according to claim 1, wherein the amine-functional compound and the acid are reacted with each other to form the salt.

18. A dispersing agent according to claim 3 wherein the proteins on the nitrogens of the polyalkylene imine are replaced by alkyl, aryl and/or aralkyl groups or are alkoxylated or quaternized.

19. A dispersing agent according to claim 4 wherein the polyalkylene amine is an aziridine polymer.

20. A dispersing agent according to claim 1 wherein the amine-functional compound is a homo-, co- or block polymer having a number average molecular weight of 600 to 200,000 g/mole.

21. A dispersing agent according to claim 5 wherein the mole % is from 1 to 50 mole %.

22. A dispersing agent according to claim 7 wherein the oxyalkylated monoalcohol is a C_2-C4 oxyalkylated monoalcohol.

23. A dispersing agent according to claim 8 wherein the oxyalkylated monoalcohol is a C₂ -C₄ oxyalkylated monoalcohol.

24. A dispersing agent according to claim 9 wherein R1 and/or R2 constitute a number average molecular weight of 300 to 2500 g/mole.

25. A dispersing agent according to claim 11 wherein the degree of salt formation is from 0.1 to 1.

26. A dispersing agent according to claim 11 wherein the degree of salt formation is from 0.5 to 1.

27. A pigment composition according to claim 12 which is a lacquer, paste or molding composition.

28. A dispersible solid according to claim 13 wherein the powder or fibrous particles are pigment or filler particles.

29. A pigmented lacquer according to claim 15 further comprising an ingredient selected from the group consisting of a solvent, an extender, a lacquer adjuvant substance and any mixture thereof.