Dispersants for preparing aqueous pigment pastes
View Patent ↗The invention relates to the use of copolymers with styrene-oxide-based, vinyl-functionalized polyethers for preparing aqueous pigment preparations.
1. A method for dispersing a preparation comprising solid components which is a coating paint, printing ink, or aqueous or co-solvent containing pigment concentrate which comprises adding at least one dispersing additive comprising copolymers composed of
A) from about 1 to about 80 mol % of styrene-oxide based oxyalkylene glycol ethers or polyalkylene oxide ethers which comprise of one structural group of the formula Ia, Ib, Ic and/or Id
where
R 1 =H or an aliphatic hydrocarbon radical,
p=1 to 4,
q=0 to 6,
t=0 to 4,
i=1 to 6,
l=2 or is 1 in the situation where (C m H lm O) n or (C m′ H lm′ )o is SO,
m=2 to 18,
m′=2 to 18,
the index on the H atom being formed by the product of l and m,
n=0 to 100,
o=0 to 100,
SO=styrene oxide
where
(SO) i and the alkylene oxide derivatives can be distributed randomly or blockwise in the polyether,
R 2 =H, an aliphatic, linear or branched hydrocarbon radical having 1 to 6 carbon atoms, a cycloaliphatic hydrocarbon having 5 to 8 carbon atoms an aryl radical having 6 to 14 carbon atoms, phosphoric ester or a monophosphate ester;
B) from about 1 to about 90 mol % of unsaturated carboxylic acid and/or dicarboxylic acid derivatives comprising at least one structural group of the formula II
where
S=—H, —COOM a , or —COOR 3 ,
where
M=hydrogen, monovalent or divalent metal cation, ammonium ion, or organic amine radical,
a=1 or, if M is a divalent metal cation, is ½,
R 3 =an aliphatic, linear or branched hydrocarbon radical, a cycloaliphatic hydrocarbon, or an aryl radical,
T=—U 1 —R 4 or —U 1 —(C m H lm O) n —(C m′ H lm′ O) o —R 2 ,
where
U 1 =—COO—, —CONH—, —CONR 3 —, —O—, or —CH 2 O—,
R 4 =H, M a , R 3 or —Q 1 —NQ 2 Q 3 ,
where
Q 1 is a divalent alkylene radical having 2 to 24 carbon atoms,
Q 2 and Q 3 — are aliphatic and/or alicyclic alkyl radicals having 1 to 12 carbon atoms, optionally oxidized to —Q 1 —N(+)O(−)Q 2 Q 3
and
m, m′, n, l, o, R 1 and R 2 are as defined above; and
C) from 0 to about 10 mol % of dicarboxylic acid derivatives comprising at least one structural group of the formula III
where
T 1 =—U 1 —(C m H lm O) n —(C m′ H lm′ O) o —R 5 ,
where
where
U 2 =—OOC—, —NHOC—, —O—, or —O—CH 2 —,
where
m, m′, n, l, o, S, R 1 , R 2 and U 1 are as defined above.
2. The method according to claim 1 , wherein the copolymer comprises
A) from 1 to 80 mol % of styrene-oxide based oxyalkylene glycol ethers or polyalkylene oxide ethers which comprise at least one of the structural groups of the formula Ia, Ib, Ic and/or Id
where
R 1 =H, or an aliphatic hydrocarbon radical having 1 to 5 carbon atoms,
p=1 to 4,
q=0 to 6,
t=0 to 4,
i=1 to 6,
l=2 or is 1 in the situation where (C m H lm O) n or (C m′ H lm′ O) o is SO,
m=2 to 18,
m′=2 to 18,
the index on the H atom being formed by the product of l and m or l and m,
n=0 to 100,
o=0 to 100, and the sum of (n+o)>0
SO=styrene oxide
where
(SO) i and the alkylene oxide derivatives can be distributed randomly or blockwise in the polyether,
R 2 =H, an aliphatic, linear or branched hydrocarbon radical having 1 to 6 carbon atoms, a cycloaliphatic hydrocarbon having 5 to 8 carbon atoms, an aryl radical having 6 to 14 carbon atoms, phosphoric ester or a monophosphate ester;
B) from 1 to 90 mol % of unsaturated carboxylic acid and/or dicarboxylic acid derivatives which comprise at least one structural group of the formula II
where
S=—H, —COOM a , or —COOR 3 ,
where
M=hydrogen, monovalent or divalent metal cation, ammonium ion, or an organic amine radical,
a=1 or, if M is a divalent metal cation, is ½,
R 3 =an aliphatic, linear or branched hydrocarbon radical having 1 to 20 carbon atoms, a cycloaliphatic hydrocarbon having 5 to 8 carbon atoms, or an aryl radical having 6 to 14 carbon atoms,
T=—U 1 —R 4 or —U 1 —(C m H lm O) n —(C m′ H lm′ O) o —R 2 ,
where
U 1 =—COO—, —CONH—, —CONR 3 —, —O—, or —CH 2 O—,
R 4 =H, M a , R 3 or -Q 1 -NQ 2 Q 3 ,
where
Q 1 is a divalent alkylene radical having 2 to 24 carbon atoms,
Q 2 and Q 3 —are aliphatic and/or alicyclic alkyl radicals having 1 to 12 carbon atoms, optionally oxidized to —Q 1 —N(+)O(−)Q 2 Q 3
and
m, m′, n, l, o, R 1 and R 2 are as defined above; and
C) from 0 to about 10 mol % of dicarboxylic acid derivatives which comprise at least one structural group of the formula III
where
T 1 =—U 1 —(C m H lm O) n —(C m′ H lm′ O) o —R 5 ,
where
where
U 2 =—OOC—, —NHOC—, —O—, or —O—CH 2 —,
where
m, m′, n, l, o, S, R 1 , R 2 and U 1 are as defined above.
3. The method according to claim 1 , wherein (SO); and the alkylene oxide derivatives are distributed blockwise in the following order
—(SO) i —[(C m H lm O) n —(C m′ H lm′ O) o ]—R 2 .
4. The method according to claim 2 , wherein R 2 is H.
5. The method according to claim 1 , wherein R 2 is a phosphoric mono ester derivative.
6. The method according to claim 1 , wherein up to 50 mol %, based upon the sum of structured groups A), B) and C), whose monomers are derived from vinyl, acrylic acid or methacrylic acid.
7. The method according to claim 1 , wherein up to 20 mol %, based upon the sum of structural groups A), B) and C) whose monomers are derived from vinyl, acrylic acid or methacrylic acid.
8. The method according to claim 1 , wherein the formulation is an aqueous or co-solvent containing pigment concentrate and the additive is present in amounts of from about 0.1 to 200% by weight, based upon the amount of pigment.
9. The method according to claim 1 , wherein the copolymers in the dispersing additive are composed of from about 10 to about 60 mol % of the structural group Ia, Ib, Ic and/or Ic, from about 40 to 90 mol % of the structural groups of formula II and from 0 to about 2 mol % of the structural groups of formula III.
10. The method according to claim 1 , wherein some of the structural groups of the formula II are dicarboxylic acid derivatives that contain amino oxide groups.
11. The method according to claim 1 , wherein some of the structural groups of the formula II are dicarboxylic acid derivatives containing alkyl alcohol or alkylamine groups.
12. The method according to claim 1 , wherein the copolymers are obtained by polymerizing the monomers in an aqueous solution that contains aqueous solvents at a temperature from about 20 to about 100° C.
13. The method according to claim 1 , wherein the formulation is a paint, printing ink or pigment concentrate which comprises pigments that are organic pigments.
14. The method according to claim 13 , wherein the organic pigments have been modified means of high resin fractions.
15. The method according to claim 13 , wherein the organic pigments are carbon black.
16. The method according the claim 1 , wherein the formulation is a paint, printing ink or pigment concentrate which comprises pigments that are inorganic pigments.
17. The method according to claim 16 , wherein the pigments are iron oxide.
18. A pigment-containing preparation comprising at least one pigment and from about 0.1 to about 200% by weight, based upon the pigment, of at least one dispersion additive comprising copolymers composed of
A) from about 1 to about 80 mol % of styrene-oxide based oxyalkylene glycol ethers or polyalkylene oxide ethers which comprise of one structural group of the formula Ia, Ib, Ic and/or Id
where
R 1 =H or an aliphatic hydrocarbon radical,
p=1 to 4,
q=0 to 6,
t=0 to 4,
i=1 to 6,
l=2 or is 1 in the situation where (C m H lm O) n or (C m ′H lm ′O) o is SO,
m=2 to 18,
m′=2 to 18,
the index on the H atom being formed by the product of l and m or l and m′,
n=0 to 100
o=0 to 100,
SO=styrene oxide
where
(SO) i and the alkylene oxide derivatives can be distributed randomly or blockwise in the polyether,
R 2 =H, an aliphatic, linear or branched hydrocarbon radical having 1 to 6 carbon atoms,, a cycloaliphatic hydrocarbon having 5 to 8 carbon atoms, an aryl radical having 6 to 14 carbon atoms, phosphoric ester or a monophosphate ester;
B) from about 1 to about 90 mol % of unsaturated carboxylic acid and/or dicarboxylic acid derivatives comprising at least one structural group of the formula II
where
S=—H, —COOM a , or —COOR 3 ,
where
M=hydrogen, monovalent or divalent metal cation, ammonium ion, or an organic amine radical,
a=1 or, if M is a divalent metal cation, is ½,
R 3 =an aliphatic, linear or branched hydrocarbon radical, a cycloaliphatic hydrocarbon, or an aryl radical,
T=—U 1 —R 4 or —U 1 —(C m H lm O) n —(C m′ H lm′ O) o —R 2 ,
where
U 1 =—COO—, —CONH—, —CONR 3 —, —O—, or —CH 2 O—,
R 4 =H, M a , R 3 or -Q 1 -NQ 2 Q 3 ,
where
Q 1 is a divalent alkylene radical having 2 to 24 carbon atoms,
Q 2 and Q 3 —are aliphatic and/or alicyclic alkyl radicals having 1 to 12 carbon atoms, optionally oxidized to —Q 1 —N(+)O(−)Q 2 Q 3
and
m, m′, n, l, o, R 1 and R 2 are as defined above; and
C) from 0 to about 10 mol % of dicarboxylic acid derivatives comprising at least one structural group of the formula III
where
T 1 =—U 1 —(C m H lm O) n —(C m ′H lm ′O) o —R 5 ,
where
where
U 2 =—OOC—, —NHOC—, —O—, or —O—CH 2 —,
where
m, m′, n, l, o, S, R 1 , R 2 and U 1 are as defined above.
19. The pigment-containing preparation according to claim 18 , wherein the pigment-containing preparation is an aqueous pigment paste.
20. The pigment-containing preparation according to claim 18 , wherein the pigment-containing preparation is an aqueous pigment paste.
21. The aqueous pigment paste according to claim 20 , wherein the pigment is carbon black.
22. The pigment-containing preparation according to claim 18 wherein the pigment-containing preparation is solvent free.
23. The pigment-containing preparation according to claim 18 wherein the pigment-containing preparation is a paint or a printing ink.
24. The pigment-containing preparation according to claim 18 , wherein the pigment-containing preparation is a pigment concentrate.