Reaction products containing urethane groups and urea groups

Patent metadata

Field	Value
Publication number	US-11879032-B2
Application number	US-202217726106-A
Country	US
Kind code	B2
Filing date	Apr 21, 2022
Priority date	Jul 8, 2015
Publication date	Jan 23, 2024
Grant date	Jan 23, 2024

Abstract

The present invention relates to reaction products containing urethane groups and urea groups, containing at least one species of general formula (I), to a method for producing said reaction products, to the use of said reaction products as wetting agents, dispersants, dispersion stabilizers, and/or adhesion promoters, and to compositions that contain the reaction products containing urethane groups and urea groups.

First claim

The invention claimed is:

1. A reaction product containing urethane and urea groups, comprising at least one species of the general formula (I)

where a is an integer and is 1 or 2,
b is an integer and is 1 or 2,
x is an integer and is 2 or 3,
and

R is the organic radical of a corresponding polyisocyanate R(NCO) x , R is a branched or unbranched, saturated or unsaturated organic radical having 1 to 150 carbon atoms and does not contain any free isocyanate groups,
the Y radical(s) is/are independently the organic radical(s) of a corresponding alcohol Y(OH) q where q is an integer and is 1 and Y is a branched or unbranched, saturated or unsaturated organic radical having 1 to 1000 carbon atoms, wherein the Y radicals are selected from the group consisting of polyether radical based on ethylene oxide, propylene oxide, and mixtures thereof, and having a number-average molecular weight of 200 to 10,000 g/mol, polyester radical obtained by polycondensation of one or more optionally alkyl-substituted hydroxycarboxylic acids or ring-opening polymerization of the corresponding lactones, and having number average molecular weight Mn in the range of 150 to 5,000 g/mol, and hydrocarbyl radical, wherein the hydrocarbyl radical is the hydrocarbyl group of at least one of methanol, ethanol, butanol, ethylhexanol, decanol, isotridecyl alcohol, lauryl alcohol, stearyl alcohol, isobornyl alcohol, benzyl alcohol, propargyl alcohol, oleyl alcohol, linoleyl alcohol, oxo alcohols, neopentyl alcohol, cyclohexanol, fatty alcohols, alkylphenols, alkylnaphthols, and phenylethanol,
the A radical(s) is/are independently a radical of the general formula (II)

where
the R 1 radical is H or a branched or unbranched, saturated or unsaturated organic radical having 1 to 25 carbon atoms,
the Z a group is N,
the Z b group is N or CH, and
the R 2 radical is H.

2. The reaction product containing urethane and urea 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 urethane and urea groups as claimed in claim 1 , wherein a is 1 and b is 1.

4. The reaction product containing urethane and urea groups as claimed in claim 1 , wherein the R 1 radical is phenyl.

5. A process for preparing a reaction product containing urethane and urea groups as claimed in claim 1 , wherein
i) b alcohols Y—(OH) q are reacted with at least one polyisocyanate R(NCO) x to form at least one urethane of the general formula (V)
((HO) q-1 —Y—O—CO—NH) b —R—(NCO) x-b   (V)

where
the urethane of the general formula (V) contains at least one free isocyanate group,
and
ii) at least one urethane of the general formula (V) is reacted with a species of the general formula (Ha)

to give a reaction product containing urethane and urea groups, comprising at least one species of the general formula (I)

6. A wetting agent and dispersant comprising a reaction product containing urethane and urea groups as claimed in claim 1 .

7. An adhesion promoter comprising a reaction product containing urethane and urea groups as claimed in claim 1 .

8. A composition comprising a reaction product containing urethane and urea groups as claimed in claim 1 .

9. The composition according to claim 8 , wherein the composition further comprises at least one of pigment and filler.

10. A reaction product containing urethane and urea groups as claimed in claim 1 as an additive, wetting agent, dispersant, dispersion stabilizer, adhesion promoter, viscosity reducer, or compatibilizer in coatings, varnishes, plastics, pigment pastes, sealants, cosmetics, ceramics, adhesives, potting compounds, spackling compounds, printing inks and inks other than printing inks.

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

Assignees

• BYK—Chemie GmbH
• Byk Chemie Gmbh

Inventors

• Okkel Andreas
• Pritschins Wolfgang
• Bessel Michael
• Giebelhaus Irina
• Meichsner Marcus
• Roch Monika

Classifications

• C08G18/10 Primary

  Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step · CPC title

• C08G18/283

  Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds · CPC title

• C08G18/284

  Compounds containing ester groups, e.g. oxyalkylated monocarboxylic acids · CPC title

• C08G18/3271

  Hydroxyamines · CPC title

• C08G18/3275

  containing two hydroxy groups · CPC title