Allophanate based dispersing agent

Patent metadata

Field	Value
Publication number	US-11897995-B2
Application number	US-202017626842-A
Country	US
Kind code	B2
Filing date	Jul 17, 2020
Priority date	Jul 18, 2019
Publication date	Feb 13, 2024
Grant date	Feb 13, 2024

Abstract

The presently claimed invention is directed to a copolymer obtained by reacting at least one isocyanate (A) comprising at least one allophanate group and at least one active double bond with at least one isocyanate reactive component (B) to form an intermediate product (C); and reacting the intermediate product (C) with at least one active double bond reactive component (D) to obtain the copolymer which can be used as dispersant. The at least one isocyanate reactive component (B) is selected from the group consisting of monofunctional polyether amine (B1), monofunctional polyether alcohol (B2), C6-C30 monofunctional alcohol (B3) and monofunctional polyester alcohol (B4).

First claim

The invention claimed is:

1. A copolymer obtained by:
a. reacting at least one isocyanate (A) comprising at least one allophanate group and at least one active double bond with at least one isocyanate reactive component (B) to form an intermediate product (C), wherein the intermediate product (C) has an NCO content <0.2 wt. %, based to the overall weight of the intermediate product (C); and
b. reacting the intermediate product (C) obtained in step a. with at least one active double bond reactive component (D) to obtain the copolymer;
wherein the at least one isocyanate reactive component (B) is selected from the group consisting of monofunctional polyether amine (B1), monofunctional polyether alcohol (B2),—C 6 -C 30 monofunctional alcohol (B3) and monofunctional polyester alcohol (B4);
and wherein the at least one active double bond reactive component (D) is selected from the group consisting of imidazole, 1H-imidazol-1-amine, (1H-imidazol-1-yl)methanamine, (1H-imidazol-1-yl)ethan-1-amine, 3-(1H-imidazol-1-yl)propan-1-amine, 4-(1H-imidazol-1-yl)butan-1-amine, 5-(1H-imidazol-1-yl)pentan-1-amine, N-ethyl-2-(1H-imidazol-1-yl)ethan-1-amine, (1H-imidazol-1-yl)methanethiol, 2-(1H-imidazol-1-yl)ethane-1-thiol, 3-(1H-imidazol-1-yl)propane-1-thiol, 4-(1H-imidazol-1-yl)butane-1-thiol, (1H-1,2,3-triazol-1-yl)methanamine, 1H-1,2,3-triazole, 2-(1H-1,2,3-triazol-1-yl)ethan-1-amine, 3-(1H-1,2,3-triazol-1-yl)propan-1-amine, 4-(1H-1,2,3-triazol-1-yl)butan-1-amine, 5-(1H-1,2,3-triazol-1-yl)pentan-1-amine, (1H-1,2,3-triazol-1-yl)methanethiol, 2-(1H-1,2,3-triazol-1-yl)ethane-1-thiol, 3-(1H-1,2,3-triazol-1-yl)propane-1-thiol, 4-(1H-1,2,3-triazol-1-yl)butane-1-thiol, 5-(1H-1,2,3-triazol-1-yl)pentane-1-thiol, 4H-1,2,4-triazole, (4H-1,2,4-triazol-4-yl)methanamine, 2-(4H-1,2,4-triazol-4-yl)ethan-1-amine, 3-(4H-1,2,4-triazol-4-yl)propan-1-amine, 4-(4H-1,2,4-triazol-4-yl)butan-1-amine, 5-(4H-1,2,4-triazol-4-yl)pentan-1-amine, (4H-1,2,4-triazol-4-yl)methanethiol, 2-(4H-1,2,4-triazol-4-yl)ethane-1-thiol, 3-(4H-1,2,4-triazol-4-yl)propane-1-thiol, 4-(4H-1,2,4-triazol-4-yl)butane-1-thiol, 5-(4H-1,2,4-triazol-4-yl)pentane-1-thiol, (1H-tetrazol-1-yl)methanamine, 2-(1H-tetrazol-1-yl)ethan-1-amine, 3-(1H-tetrazol-1-yl)propan-1-amine, 4-(1H-tetrazol-1-yl)butan-1-amine, N-methyl-4-(1H-tetrazol-1-yl)butan-1-amine, 5-(1H-tetrazol-1-yl)pentan-1-amine, (1H-tetrazol-1-yl)methanethiol, 2-(1H-tetrazol-1-yl)ethane-1-thiol, 3-(1H-tetrazol-1-yl)propane-1-thiol, 4-(1H-tetrazol-1-yl)butane-1-thiol and 5-(1H-tetrazol-1-yl)pentane-1-thiol, N,N-diethyl-1,4-butanediamine, 1-(2-aminoethyl)piperazine, 2-(1-pyrrolidyl)-ethylamine, 4-amino-2-methoxy-pyrimidine, 2-dimethylaminoethanol, 1-(2-hydroxyethyl)piperazine, 4-(2-hydroxyethyl)morpholine, 2-mercaptopyrimidine, 2-mercaptobenzimidazole, N,N-dimethyl-1,3-propanediamine, 4-(2-aminoethyl)pyridine, 2-amino-6-methoxy-benzothiazole, 4-aminomethyl-pyridine, N,N-diallylmelamine, 3-amino-1,2,4-triazole, 1-(3-aminopropyl)imidazole, 4-(2-hydroxyethyl)pyridine, 1-(2-hydroxyethyl)imidazole and 3-mercapto-1,2,4-triazole, 1-(2-aminoethyl)imidazolidin-2-one, benzylamine, aniline, branched or linear (C 2 H 5 N) 1-500 and salts thereof.

2. The copolymer according to claim 1 , wherein the at least one isocyanate (A) comprising at least one allophanate group and at least one active double bond contains 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 NCO groups.

3. The copolymer according to claim 1 , wherein the at least one isocyanate (A) comprising at least one allophanate group and at least one active double bond is obtained by reacting at least one polyisocyanate (A1) with at least one compound of formula (A2),

wherein Z is selected from the group consisting of —O—, —NR 5 — and —S—;
R 1 and R 2 are independently of each other selected from the group consisting of H or CH3, linear or branched, substituted or unsubstituted C 1 -C 30 alkyl, linear or branched, substituted or unsubstituted C 2 -C 30 alkenyl, and substituted or unsubstituted phenyl;
G is selected from the group consisting of —(CH 2 ) k —OH, —(CH 2 —CH 2 —O) m H, —(—CH(R 3 )—CH(R 4 )—O—) n —H, —CH 2 —CH(OH)—CH 2 —O—C(═O)—C(CH 3 )═CH 2 and —CH 2 —CH(OH)—CH 2 —O—C(═O)—CH═CH 2 ;
k, m and n are independently of each other an integer in the range of ≥1 to ≤20;
R 3 and R 4 are independently of each other selected from the group consisting of H, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl and tert-butyl; and
R 5 is selected from the group consisting of H, linear or branched, substituted or unsubstituted C 1s -C 30 alkyl, linear or branched, substituted or unsubstituted C 2 -C 30 alkenyl, and substituted or unsubstituted phenyl.

4. The copolymer according to claim 3 , wherein the at least one polyisocyanate (A1) is selected from the group consisting of 4,4′-diphenylmethanediisocyanate, toluene diisocyanate, naphthylene-1,5-diisocyanate, 1,3-or 1,4-phenylene-diisocyanate, triphenylmethane-4,4′,4″-triisocyanate, poly phenyl-polymethylene polyisocyanate, hexamethylene diisocyanate, 1,12-dodecanediisocyanate, cyclobutane-1,3-diisocyanate, cyclohexane-1,3- or 1,4-diisocyanate, 1-isocyanato-3,3,5-trimethyl-5-isocyanate-methylcyclohexane, 2,4- or 2,6-hexahydrotolyene-diisocyanate, hexahydro-1,3- or -1,4-phenyidiisocyanate and perhydro-2,4′- or -4,4′-dicyclohexylmethanediisocyanate.

5. The copolymer according to claim 3 , wherein the at least one compound of formula (A2) is selected from the group consisting of hydroxy acrylate (A2a), and hydroxy acrylamide (A2b).

6. The copolymer according to claim 3 , wherein the at least one compound of formula (A2) is selected from the group consisting of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate, hydroxybutyl acrylate, hydroxybutyl methacrylate, hydroxyethyl acrylamide, and hydroxyethyl methacrylamide.

7. The copolymer according to claim 1 , wherein the at least one isocyanate (A) has active double bonds in the range from ≥1 to ≤10.

8. The copolymer according to claim 1 , wherein the at least one active double bond is a double bond which is conjugated with at least one carbonyl group.

9. The copolymer according to claim 1 , wherein the monofunctional polyether amine (B1) is of formula (B1),

wherein Y is selected from the group consisting of H, linear or branched, substituted or unsubstituted C 1 -C 30 alkyl, and G—(O(CH 2 ) s CH 2 ) o —(CH 2 —CH(Q)) p —;
o and p are independently of each other an integer in the range of ≥0 to ≤2000;
s is an integer in the range of ≥1 to ≤10;
wherein o+p is an integer in the range of ≥1 to ≤4000; and
Q and G are independently of each other selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl and substituted or unsubstituted phenyl.

10. The copolymer according to claim 9 , wherein the monofunctional polyether amine (B 1) has a weight average molecular weight in the range of ≥120 to ≤10000 g/mol, as determined according to GPC.

11. The copolymer according to claim 1 , wherein the copolymer has weight average molecular weight M w in the range of ≥1000 g/mol to ≤100000 g/mol, as determined according to GPC.

12. A method for preparing a copolymer according to claim 1 , wherein the process comprises the steps of:
i) mixing at least one isocyanate (A) comprising at least one allophanate group and at least one active double bond, with at least one isocyanate reactive component (B) to ob

Assignees

• Basf Se

Inventors

• Gernandt Andreas
• Kou Huiguang
• Onclin Steffen
• Auschra Clemens
• Willenbacher Johannes Hermann

Classifications

• C08G18/7837 Primary

  containing allophanate groups · CPC title

• C08G18/285

  Nitrogen containing compounds · CPC title

• C08G18/8175 Primary

  with esters of acrylic or alkylacrylic acid having only one group containing active hydrogen · CPC title

• C08G18/833

  by nitrogen containing compounds (by azo compounds C08G18/85) · CPC title

• C09D175/04

  Polyurethanes · CPC title