Reaction products containing amidoamine groups

Patent metadata

Field	Value
Publication number	US-10544091-B2
Application number	US-201615575128-A
Country	US
Kind code	B2
Filing date	Jun 3, 2016
Priority date	Jun 3, 2015
Publication date	Jan 28, 2020
Grant date	Jan 28, 2020

Abstract

A reaction product containing amido amine groups, comprising one or more species of the general formula (I)

(R 1 —X) p —Z 1 —(XH) y   (I)

where p+y=w and w is an integer from 1 to 10, p is an integer from 1 to 10, y is an integer from 0 to 9, and X is independently O, NH and/or NZ 2 and XH is independently a hydroxyl group OH, a primary amino group NH 2 and/or a secondary amino group NHZ 2 where Z 2 is independently a branched or unbranched, saturated or unsaturated organic radical G(U) a where U is independently a hydroxyl group, a primary amino group or a secondary amino group and a is an integer from 0 to 9, where p+y+a≤10, and G is a branched or unbranched, saturated or unsaturated organic radical, the p R 1 radicals are independently a radical of the general formula (II)

Y—O—CO—NH—R 2 —NH—CO  (II)

in which the p Y radicals are independently a branched or unbranched, saturated or unsaturated organic radical which has 1 to 1000 carbon atoms and does not contain any hydroxyl groups, any primary amino groups or any secondary amino groups, the p R 2 radicals are independently a branched or unbranched, saturated or unsaturated organic radical having 6 to 20 carbon atoms,

Z 1 is a branched or unbranched, saturated or unsaturated organic radical containing at least two carbon atoms, having at least one amide group and at least one tertiary amino group.

First claim

The invention claimed is:

1. A reaction product containing amido amine groups, comprising one or more species of general formula (I)
(R 1 —X) p —Z 1 —(XH) y   (I)

where p+y=w and
w is an integer from 1 to 10,
p is an integer from 1 to 10,
y is an integer from 0 to 9, and
X is O, and XH is a hydroxyl group OH,
where p+y<10, and
the p R 1 radicals are independently a radical of general formula (II)
Y—O—CO—NH—R 2 —NH—CO  (II)

in which the p Y radicals are independently a branched or unbranched, saturated or unsaturated organic radical which has 1 to 1000 carbon atoms and does not contain any hydroxyl groups, any primary amino groups or any secondary amino groups,
the p R 2 radicals are independently a branched or unbranched, saturated or unsaturated organic radical having 6 to 20 carbon atoms, and
Z 1 is a branched or unbranched, saturated or unsaturated organic radical containing at least two carbon atoms, having at least one amide group and at least one tertiary amino group.

2. The reaction product containing amido amine groups as claimed in claim 1 , containing at least 40% by weight of one or more species of the general formula (I).

3. The reaction product containing amido amine groups as claimed in claim 1 , wherein a species of general formula (IV) which is free of urethane groups, is reactive toward isocyanate groups and is a reactant for the reaction product comprising one or more species of the formula (I)
(HX) p —Z 1 —(HX) y   (IV)

with p, y, X and Z 1 as defined for the general formula (I),
wherein the species of general formula (IV) is obtained by reacting one or more components A with one or more components B, one or more components C, or one or more components B and C, wherein
component A is selected from the group of ethylenically unsaturated carboxylic acids, esters thereof and acid halides thereof, where at least one C═C double bond and at least one C═O double bond are in conjugated form and the C═O double bond is selected from the group of the carboxylic acids, the carboxylic esters and the carbonyl halides;
component B is of general formula (V)
(R 3 ) x —HN—(R 4 ) z   (V)

where x+z=2 and
x is an integer from 0 to 2,
z is an integer from 0 to 2, and
R 3 is independently H or a branched or unbranched, saturated or unsaturated organic radical having 1 to 12 carbon atoms, and
R 4 is independently a branched or unbranched, saturated or unsaturated organic radical having 2 to 12 carbon atoms and 1 to 3 tertiary amino groups; and
component C is of general formula (VI)
(R 5 ) k —HN—(R 6 ) n   (VI)

where k+n=2 and
k is an integer from 0 to 1,
n is an integer from 1 to 2, and
R 5 is H or a branched or unbranched, saturated or unsaturated organic radical having 1 to 12 carbon atoms, and
R 6 is independently a branched or unbranched, saturated or unsaturated organic radical having 2 to 12 carbon atoms and 1 to 4 hydroxyl groups.

4. The reaction product containing amido amine groups as claimed in claim 3 , wherein component A is an ethylenically unsaturated carboxylic ester.

5. The reaction product containing amido amine groups as claimed in claim 1 , wherein Y contains at least one polyether radical, polyester radical, hydrocarbyl radical, polysiloxane radical, or mixtures thereof.

6. A process for preparing the reaction product containing amido amine groups as claimed in claim 3 , wherein
i) at least one diisocyanate R 2 (NCO) 2 is reacted with at least one monoalcohol Y—OH to form a urethane of general formula (III)
Y—O—CO—NH—R 2 —NCO  (III)

ii) p urethanes of the general formula (III) are reacted to give a reaction product containing amido amine groups, comprising one or more species of the general formula (I)
(R 1 —X) p —Z 1 —(XH) y   (I)

 and
wherein step ii) is conducted in one stage ii-a) or in a stage sequence ii-b),
in stage ii-a) p urethanes of the general formula (III) are reacted with a species of the general formula (IV) which is free of urethane groups and reactive toward isocyanate groups, and
in stage ii-b) p urethanes of the general formula (III) are reacted with an intermediate I containing at least one HX group reactive toward isocyanate groups with X as defined for the general formula (I) to form an intermediate J, wherein I is a Michael addition product of at least one component A with a component B or C, and then the intermediate J formed is reacted in an amidation reaction with a component B or C.

7. The process as claimed in claim 6 , wherein the diisocyanate R 2 (NCO) 2 is used in step i) relative to the monoalcohol Y—OH in a molar ratio of at least 1.1:1.0 and the diisocyanate R 2 (NCO) 2 that has not been converted to the urethane of the general formula (III) in step i) is removed from the reaction mixture, optionally by distillation, prior to the performance of step ii).

8. The process as claimed in claim 6 , wherein the diisocyanate R 2 (NCO) 2 corresponding to the R 2 radical has two isocyanate groups of different reactivity.

9. The process as claimed in claim 8 , wherein the diisocyanate R 2 (NCO) 2 is selected from the group consisting of toluene 2,4-diisocyanate and isophorone diisocyanate.

10. A wetting agent and dispersant comprising the reaction product containing amido amine groups, as claimed in claim 1 .

11. A composition comprising the reaction product containing amido amine groups, as claimed in claim 1 .

12. A method of utilizing the reaction product containing amido amine groups as claimed in claim 1 , comprising adding the reaction product as a wetting agent or dispersant or dispersion stabilizer or viscosity reducer or compatibilizer in coatings, varnishes, plastics, pigment pastes, sealants, cosmetics, ceramics, adhesives, potting compounds, spackling compounds, printing inks or other inks.

13. A reaction product containing amido amine groups which is one species of the general formula (I) of the reaction product as claimed in claim 1 .

14. A reaction product containing amido amine groups, comprising one or more salt(s), one or more quaternization product(s), or one or more salts and one or more quaternization products of the species of the general formula (I) of the reaction product as claimed in claim 1 .

15. A reaction product containing amido amine groups, comprising one or more modification products of the species of the general formula (I) of the reaction product as claimed in claim 1 , wherein at least one of a) the one or more tertiary amino groups of the general formula (I) have been converted to amine oxides with oxygen, peroxo compounds or mixtures thereof, or b) XH groups still present in the general formula (I) have been reacted with carboxylic anhydrides.

16. The reaction product containing amido amine groups as claimed in claim 1 , containing at least at least 90% by weight of one or more species of the general formula (I).

17. A wetting agent and dispersant comprising the reaction product containing amido amine groups, prepared by the process as claimed in claim 6 .

18. A composition comprising the reaction product containing amido amine groups, prepared by the process as claimed in claim 6 .

19. A method of utilizing the reaction product containing amido amine groups prepared by the process as claimed in claim 6 , comprising adding the reaction product as a wetting agent or dispersant or dispersion stabilizer or viscosity reducer or compatibilizer in coatings, varnishes, plastics, pigment pastes, sealants, cosmetics, ceramics, adhesives, potting compounds, spackling compounds, pri

Assignees

• Byk Chemie Gmbh

Inventors

• Okkel Andreas
• Göbelt Bernd
• Omeis Jürgen
• Bömer Jörg
• Roch Monika
• Stelz Sabine

Classifications

• C08G18/7621

  being toluene diisocyanate including isomer mixtures · CPC title

• C07C237/04 Primary

  the carbon skeleton being acyclic and saturated · CPC title

• C08G18/71

  Monoisocyanates or monoisothiocyanates · CPC title

• C08G18/2835

  having less than 5 ether groups · CPC title

• C08G18/718

  containing silicon · CPC title