Melamine-polyethers as dispersants in non-aqueous, liquid pigment compositions

Patent metadata

Field	Value
Publication number	US-11242467-B2
Application number	US-201716071120-A
Country	US
Kind code	B2
Filing date	Jan 20, 2017
Priority date	Jan 22, 2016
Publication date	Feb 8, 2022
Grant date	Feb 8, 2022

Abstract

The present invention relates to novel mono- or polynuclear melamine compounds and their use as dispersants for pigments and fillers in coating compositions, in particular in solvent-borne coating compositions. The mono- or polynuclear melamine compounds of the invention have at least one 2,4,6-triamino-1,3,5-triazine ring, wherein at least one amino groups of at least one of the 2,4,6-triamino-1,3,5-triazine rings of the mono- or polynuclear melamine compounds is of the formula A:NR1R2 (A) where R1 is H, CH(R3)OR4 or R2, R2 is CH(R3)O(A-O)x—R5, where R3 is H, C1-C10-alkyl or aryl; R4 is H, C1-C4-alkyl or C1-C4-alkoxy-C1-C4-alkyl; R5 is a hydrocarbon radical having from 1 to 40 carbon atoms; x is an integer from 2 to 500, having on average a value in the range from 2.5 to 400; A is an C2-C4-alkan-1,2-diyl radical.

First claim

We claim:

1. A mixture of mono- or polynuclear melamine compounds comprising a 2,4,6 triamino-1,3,5-triazine ring, wherein at least one amino group is of a formula (1):
NR 1 R 2   (1)

where
R 1 is H, CH(R 3 )OR 4 , or R 2 ,
R 2 is CH(R 3 )O(A-O) x —R 5 , where
R 3 is C 1 -C 10 -alkyl, or aryl,
R 4 is H, C 1 -C 4 -alkyl, or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl,
R 5 is a hydrocarbon radical having 1 to 40 carbon atoms, which is selected from C 1 -C- 22 -alkyl, aryl-C 1 -C 4 -alkyl or aryl, where aryl in aryl-C 1 -C 4 -alkyl or aryl is phenyl or naphthyl and is unsubstituted, carries 1 C 1 -C 10 -alkyl group, or carries 2 C 1 -C 10 -alkyl groups;
x is an integer from 2 to 500, having a number average value in a range of 3 to 200;
A is a C 2 -C 4 -alkan-1,2-diyl radical.

2. The mixture of claim 1 , where the mono- or polynuclear melamine compounds are selected from the group consisting of a mononuclear melamine compound of a formula (M1), a binuclear polynuclear melamine compound of a formula (M2), and a polynuclear melamine compound of a formula (M3),

where in formula (M1)
at least one of the radicals A 1 , A 2 and A 3 is a radical of the formula (A) as defined in claim 1 , while any of the remaining radicals A 1 , A 2 and/or A 3 that are not of the formula (A) are of a formula NHR x or a formula NWR y ,
where in formula (M2)
at least one of the radicals A 1 , A 2 , A 4 and A 5 is a radical of the formula (1) as defined in claim 1 , while any of the remaining radicals A 1 , A 2 , A 4 and/or A 5 are of a formula NHR x or a formula NWR y ,
L is a bivalent linker CH(R 3 ) or CH(R 3 )[O—CH(R 3 )] k , where k is an integer, which is in a range of 1 to 5, and
A 33 and A 34 are radicals NR z ,
and
where in formula (M3)
at least one of the radicals A 6 , A 7 and A 8 is a radical of a formula (Ma)

wherein p is 0 or an integer in a range of 1 to 20, provided that in at least one of the groups Ma the variable p is different from 0,
# indicates a point of attachment to the triazine ring of (M3),
L and L′ are identical or different bivalent linkers as defined for L in formula (M2),
A 33 , A 34 , A 35 and A 36 are radicals NR z ,
provided at least one of the radicals A 2 , A 4 , A 5 , A 6 , A 7 and A 8 is a radical of the formula (A), while any of the remaining radicals A 2 , A 4 and A 5 are of a formula NHR x or a formula NR x R y , and any of the remaining radicals A 6 and A 7 are of formula Ma, formula NHR x , or formula NR x R y , and where
R x is CH(R 3 )OR 4 or CH(R 3 )O—R 8 ,
R y is CH(R 3 )OR 4 or CH(R 3 )O—R 8 ,
R z is hydrogen, CH(R 3 )OR 4 , or CH(R 3 )O—R 8 , and
R 8 is a hydrocarbon radical having from 5 to 40 carbon atoms.

3. The mixture of claim 1 , where in formula (1)
A is selected from the group consisting of an ethan-1,2-diyl, a propan-1,2-diyl, and mixtures thereof.

4. The mixture of claim 1 , wherein formula (1)
A is ethan-1,2-diyl;
x is an integer having a number average value in a range of 5 to 60;
R 5 is C 1 -C 4 -alkyl.

5. The mixture of claim 1 , where in formula (1) R 1 is hydrogen.

6. The mixture of claim 1 , wherein at least one 2,4,6-triamino-1,3,5-triazine ring bears an amino group of the formula (B):
NR 6 R 7   (B)

where
R 6 is H or CH(R 3 )OR 4 ,
R 7 is CH(R 3 )O—R 8 , where
R 3 is C 1 -C 10 -alkyl, or aryl,
R 4 is H, C 1 -C 4 -alkyl, or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl,
R 8 is a hydrocarbon radical having 5 to 40 carbon atoms.

7. The mixture of claim 6 , where R 6 is hydrogen and R 8 is C 8 -C 20 -alkyl or C 8 -C 20 -alkenyl.

8. The mixture of claim 1 , where the O(A-O) x —R 5 present in the melamine compounds amount to 20 to 95% by weight, based on a total weight of the melamine compounds.

9. The mixture of claim 1 , where on average at least 10 mol-% of the amino groups of the 2,4,6-triamino-1,3,5-triazine ring are of the formula (1).

10. The mixture of claim 1 , wherein at least one feature, i) or ii), is present:
i) R 3 is C 1 -C 4 -alkyl;
ii) the melamine compounds have a weight average molecular weight in a range of 520 Dalton to 120000 Dalton.

11. The mixture of claim 1 , which is obtained by a process 1) or a process 2),
where the process 1) comprises:
a) reacting 2,4,6-triamino-1,3,5-triazine and an aldehyde of a formula R 3 —CHO and optionally an alcohol R 4a —OH, wherein R 3 is as defined in claim 1 and R 4a is C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl;
b) reacting the reaction product of a) with a polyether of a formula (II)
R 5 —[O-A] x OH  (II)

wherein R 5 , A, and x are as defined in claim 1 ;
and where process 2) comprises:
reacting a polyether of a formula (II)
R 5 —[O-A] x OH  (II)

wherein R 5 , A, and x are as defined in claim 1 ,
with 2,4,6-triamino-1,3,5-triazine and an aldehyde of a formula R 3 —CHO and optionally an alcohol R 4a —OH or R 8 —OH, wherein R 3 is as defined in claim 1 , R 8 is a hydrocarbon radical having 5 to 40 carbon atoms, and R 4a is C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl.

12. A process for preparing a mixture of melamine compounds of claim 1 , the process comprising:
I)
a) reacting 2,4,6-triamino-1,3,5-triazine and an aldehyde of a formula R 3 —CHO and optionally an alcohol R 4a —OH, wherein R 3 is as defined in claim 1 and R 4a is C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl;
b) reacting the reaction product of a) with a polyether of a formula (II)
R 5 —[O-A] x OH  (II)

wherein R 5 , A, and x are as defined in claim 1 ;
or,
II)
reacting a polyether of a formula (II)
R 5 —[O-A] x OH  (II)

wherein R 5 , A, and x are as defined in claim 1 ,
with 2,4,6-triamino-1,3,5-triazine and an aldehyde of a formula R 3 —CHO and optionally an alcohol R 4a —OH or R 8 —OH, wherein R 3 is as defined in claim 1 , R 8 is a hydrocarbon radical having 5 to 40 carbon atoms, and R 4a is C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl.

13. The process of claim 12 , where a reaction with polyether of formula (II) is performed in the presence of a catalytic amount of a Broensted acid.

14. The process of claim 12 , where an amount of polyether of formula (II) is in a range of 20 to 95% by weight, based on a total weight of polyether of formula (II), aldehyde of formula R 3 —CHO, and 2,4,6-triamino-1,3,5-triazine.

15. A method of dispersing a pigment in a non-aqueous, liquid composition, the method comprising: dispersing the pigment in the non-aqueous liquid with a mixture of melamine compounds of claim 1 .

16. A non-aqueous pigment composition comprising a mixture of melamine compounds of claim 1 , a pigment component selected from the group consisting of pigments and mixtures of at least one pigment and at least one filler, and a non-aqueous diluent.

17. The non-aqueous pigment composition of claim 16 , which is a pigment paste.

18. The non-aqueous pigment composition of claim 16 , where a weight ratio of pigment component to melamine compound, calculated in each case as solids, is in a range from 20:1 to 1:1.

19. A solvent-borne coating composition comprising the pigment composition of claim 16 .

20. The mixture of melamine

Assignees

• Basf Se

Inventors

• Boerzsoenyi Gabor
• Duris Tibor
• Weinkoetz Stephan
• Reuter Frank
• Pirrung Frank

Classifications

• C08G73/0273

  Polyamines containing heterocyclic moieties in the main chain · CPC title

• C09D17/002 Primary

  in organic medium (C09D17/003, C09D17/004 take precedence) · CPC title

• C09D7/65

  macromolecular (C09D7/41-C09D7/48 take precedence) · CPC title

• C07D251/70 Primary

  Other substituted melamines · CPC title

• C09D7/41

  Organic pigments; Organic dyes · CPC title