Urethane-group-containing reaction products

Patent metadata

Field	Value
Publication number	US-10253133-B2
Application number	US-201615575219-A
Country	US
Kind code	B2
Filing date	Jun 3, 2016
Priority date	Jun 3, 2015
Publication date	Apr 9, 2019
Grant date	Apr 9, 2019

Abstract

A reaction product containing urethane 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 2 to 10, p is an integer from 2 to 10, y is an integer from 0 to 8, 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 8, where w+a≤10, 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, and Z 1 is a branched or unbranched, saturated or unsaturated organic radical which contains at least one tertiary nitrogen group and is free of XH groups.

First claim

The invention claimed is:

1. A reaction product containing urethane groups, comprising at least 40% by weight 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 2 to 10,
p is an integer from 2 to 10,
y is an integer from 0 to 8, 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 8,
where w+a≤10, and
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 which contains at least one tertiary nitrogen group and is free of XH groups,
wherein the one or more species of formula (I) is obtained from at least one component of formula (IV)
(HX) p —Z 1 —(XH) y   (IV)

wherein p hydrogens linked to X have been substituted by R 1 , and wherein the at least one component of formula (IV) is selected from the group consisting of trialkanolamines; N-alkyldialkanolamines; N-alkyl(aminoalkyl)hydroxyalkylamines; N,N-dialkyl (dihydroxyalkyl)amines; tetrakis(hydroxyalkyl)alkylenediamines; dialkylaminoalkyl dialkanolamines; N-aryldialkanolamines; N-alkanolpiperazines; hexaalkylol-2,4,6-triamino-1,3,5-triazoles; polyamines having at least one tertiary amino group and 2 to 10 primary amino groups, secondary amino groups, or primary and secondary amino groups; trisaminoalkylamines; N-alkyldiaminoalkylamines; N,N-dimethyldialkylenetriamines; heterocyclic amines; and polyethyleneimines having 2 to 10 primary amino groups, secondary amino groups, or primary and secondary amino groups.

2. The reaction product containing urethane groups as claimed in claim 1 , wherein the at least one tertiary nitrogen group is a tertiary amino group.

3. The reaction product containing urethane groups as claimed in claim 1 , containing at least 60% by weight of one or more species of the general formula (I).

4. The reaction product containing urethane groups as claimed in claim 1 , wherein the diisocyanate R 2 (NCO) 2 corresponding to the R 2 radical has two isocyanate groups of different reactivity.

5. The reaction product containing urethane groups as claimed in claim 1 , wherein Y contains at least one polyether radical, polyester radical, hydrocarbyl radical and/or polysiloxane radical.

6. A process for preparing the reaction product containing urethane groups as claimed in claim 1 , wherein
i) at least one diisocyanate R 2 (NCO) 2 is reacted with at least one monoalcohol Y—OH to form a urethane of the general formula (III)
Y—O—CO—NH—R 2 —NCO  (III)

ii) p urethanes of the general formula (III) are reacted with at least one component of the formula (IV)
(HX) p —Z 1 —(HX) y   (IV)

wherein the at least one component of formula (IV) is selected from the group consisting of trialkanolamines; N-alkyldialkanolamines; N-alkyl(aminoalkyl)hydroxyalkylamines; N,N-dialkyl(dihydroxyalkyl)amines; tetrakis(hydroxyalkyl)alkylenediamines; dialkylaminoalkyldialkanolamines; N-aryldialkanolamines; N-alkanolpiperazines; hexaalkylol-2,4,6-triamino-1,3,5-triazoles; polyamines having at least one tertiary amino group and 2 to 10 primary amino groups, secondary amino groups, or primary and secondary amino groups; trisaminoalkylamines; N-alkyldiaminoalkylamines; N,N-dimethyldialkylenetriamines; heterocyclic amines; and polyethyleneimines having 2 to 10 primary amino groups, secondary amino groups, or primary and secondary amino groups,
to give a reaction product containing urethane groups, comprising one or more species of the general formula (I)
(R 1 —X) p —Z 1 —(XH) y   (I).

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 urethane groups, as claimed in claim 1 .

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

12. A method of utilizing the reaction product containing urethane 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 urethane groups which is one species of the general formula (I) of the reaction product as claimed in claim 1 .

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

15. A reaction product containing urethane 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 one or more tertiary amino groups of the general formula (I) have been converted to amine oxides with oxygen and/or peroxo compounds and or XH groups still present in the general formula (I) have been reacted with carboxylic anhydrides.

16. The reaction product containing urethane groups as claimed in claim 1 , containing 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 urethane groups, prepared by the process as claimed in claim 6 .

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

19. A method of utilizing the reaction product containing urethane 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, printing inks or other inks.

20. The reaction product containing urethane groups as claimed in claim 1 , wherein the at least one component of formula (IV) is selected from triethanolamine, triisopropanolamine, N-methyldiethanolamine, N-butyldiethanolamine, N-methyldiisopropanolamine, bis(2-hydroxye

Assignees

• Byk Chemie Gmbh

Inventors

• Göbelt Bernd
• Okkel Andreas
• Piestert Frederik
• Pritschins Wolfgang
• Omeis Jürgen
• Bömer Jörg
• Heitzer Jennifer
• Hoverath Eva
• Stelz Sabine
• Tiegs Werner

Classifications

• C09D7/65

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

• C09D11/102

  containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds · CPC title

• C08G18/809

  containing silicon · CPC title

• C08G18/282

  Alkanols, cycloalkanols or arylalkanols including terpenealcohols · CPC title

• C08G18/3278

  containing at least three hydroxy groups · CPC title