Storage-stable urea preparations which are suitable as rheology control agents

Patent metadata

Field	Value
Publication number	US-9796860-B2
Application number	US-201515303620-A
Country	US
Kind code	B2
Filing date	Apr 15, 2015
Priority date	Apr 15, 2014
Publication date	Oct 24, 2017
Grant date	Oct 24, 2017

Abstract

The invention relates to a urea preparation containing (A) 5 to 75 wt. % of one or more urea components which have a molecular weight of at least 350 g/mol and contain at least one urea group; (B) 15 to 95 wt. %, preferably 30 to 80 wt. %, of one or more organic solvents from the group of N alkyl amides that have a molecular weight of 155 to 700 g/mol, are free of urea groups, and have the following formula (I), in which (a) R 1 is an x-containing hydrocarbon group, where x=1 to 24 carbon atoms, R 2 is a y-containing organic group, where y=1 to 12 carbon atoms, and R 3 is a z-containing organic group, where z=1 to 12 carbon atoms, or (b) R 1 , R 2 , and R 3 are defined as in (a) but R 1 and R 2 are connected to each other by a chemical bond and together form a ring with 4 to 10 ring atoms while incorporating the group C(═O)N, and in the case of a ring with 4 or 5 ring atoms, R 3 contains at least 6 carbon atoms and maximally 11 carbon atoms, or (c) R 1 , R 2 , and R 3 are defined as in (a) but R 2 and R 3 are connected to each other by a chemical bond and together form a ring with 4 to 10 ring atoms while incorporating the nitrogen atom of the general formula (I) with the proviso that for each of (a), (b), and (c), x+y+z≧8; (C) 0 to 35 wt. % of one or more organic solvents which differ from (B) and do not contain urea groups or ionic groups and which have maximally two heteroatoms selected from the group consisting of nitrogen and oxygen; and (D) 0 to 50 wt. % of a salt which differs from the urea component(s) (A), the solvent(s) (B), and the solvent(s) (C), wherein the sum of all of the stated weight percentages equals the total weight of the urea preparation. The invention further relates to the use of the urea preparation as a rheology additive for liquid compositions and to liquid media which contain the urea preparations.

First claim

The invention claimed is:

1. A urea preparation comprising
(A) 5% to 75% by weight of one or more urea components having a molecular weight of ≧350 g/mol and containing at least one urea group,
(B) 15% to 95% by weight of one or more organic solvents from the group of the N-alkylamides which have a molecular weight of 155 to 700 g/mol, are free of urea groups and have the following general formula (I):

in which
(a) R 1 is a hydrocarbyl radical containing x=1 to 24 carbon atoms,
R 2 is an organic radical containing y=1 to 12 carbon atoms, and
R 3 is an organic radical containing z=1 to 12 carbon atoms,

or
(b) R 1 , R 2 and R 3 are as defined under (a), but R 1 and R 2 are bonded to one another by a chemical bond and together, with inclusion of the C(═O)N group, form a ring having 4 to 10 ring atoms; and, in the case of a ring having 4 or 5 ring atoms in which x+y<4, the R 3 radical contains at least 6 carbon atoms and at most 11 carbon atoms
or
(c) R 1 , R 2 and R 3 are as defined under (a), but R 2 and R 3 are bonded to one another by a chemical bond and together, with inclusion of the nitrogen atom in the general formula (I), form a ring having 4 to 10 ring atoms,
with the proviso that, for each of (a), (b) and (c), x+y+z≧8,

(C) 0% to 35% by weight of one or more organic solvents other than (B) which do not contain any urea group or any ionic group and have a maximum of two heteroatoms selected from the group consisting of nitrogen and oxygen, and
(D) 0% to 50% by weight of a salt which differs from the urea component(s) (A), the solvent(s) (B) and the solvent(s) (C), and
where all percent by weight figures are based on the total weight of the urea preparation.

2. The urea preparation as claimed in claim 1 , comprising
(A) 10% to 65% by weight of the urea component(s) having a weight-average molecular weight of 350 to 60,000 g/mol and containing at least one urea group,
(B) 20% to 85% by weight of the organic solvent(s) from the group of the N-alkylamides having a molecular weight of 155 to 700 g/mol, being free of urea groups and having the general formula (I),
(C) 0% to 25% by weight of the organic solvent(s) other than (B) which do not contain any urea group or any ionic group and have a maximum of two heteroatoms selected from the group consisting of nitrogen and oxygen, and
(D) 0% to 15% by weight of the salt, and
where all percent by weight figures are based on the total weight of the urea preparation.

3. The urea preparation as claimed in claim 1 , wherein 50% to 100% by weight of the solvent (B) of the general formula (I), based on the total weight of the solvent (B), is an intermolecular amide (B1) in which
R 1 is a branched or unbranched, saturated or unsaturated, hydrocarbyl radical containing 3 to 17 carbon atoms;
R 2 and R 3 in each case are the same or different and are independently a branched or unbranched, saturated or unsaturated organic radical having 1 to 6 carbon atoms,
or
R 2 and R 3 are joined to one another by a chemical bond and, with inclusion of the nitrogen atom in the general formula (I), form a ring having 5 to 7 ring atoms.

4. The urea preparation as claimed in claim 1 wherein 50% to 100% by weight of the solvent (B) of the general formula (I), based on the total weight of the solvent (B), is an intramolecular amide (B2) in which
R 1 and R 2 are joined to one another by a chemical bond and, with inclusion of the C(═O)N group, form a ring having 4 to 8 ring atoms, where one or more ring carbon atoms are optionally substituted by a C 1 -C 4 -alkyl radical.

5. The urea preparations as claimed in claim 1 , in which 70% to 100% by weight of the urea component (A), based on the total weight of the urea components (A), has either at least two urea groups or at least one urea group and at least one urethane group, or at least two urea groups and two urethane groups.

6. The urea preparations as claimed in claim 1 , wherein
(i) 50% to 100% by weight of the urea component (A), based on the total weight of the urea components (A), of the general formula (II)
R 31 —[R 33 —Z—R 34 —W—] n R 32    (II)

is present, in which
R 31 and R 32 in each case are the same or different and are each independently a branched or unbranched, saturated or unsaturated organic radical which contains 1 to 100 carbon atoms and has a maximum of one urea group in each case and a maximum of one urethane group in each case,
R 33 and R 34 in each case are the same or different and are each independently branched or unbranched polyester radicals containing 1 to 300 carbon atoms and optionally containing ether groups, branched or unbranched polyether radicals containing 2 to 300 carbon atoms, branched or unbranched polyamide radicals containing 1 to 300 carbon atoms, polysiloxane radicals containing 3 to 100 silicon atoms, branched or unbranched C 2 -C 22 -alkylene radicals, branched or unbranched C 3 -C 18 -alkenylene radicals, C 5 -C 12 -arylene radicals and/or branched or unbranched C 7 -C 22 -arylalkylene radicals,
Z and W in each case are the same or different and are each independently NH—CO—O and/or NH—CO—NH, and
n is an integer from 1 to 150;

or
(ii) 50% to 100% by weight of the urea component (A), based on the total weight of the urea components (A), in each case has a weight-average molecular weight of 2000 to 55,000 g/mol and contains 4 to 150 urea groups;
or
(iii) 50% to 100% by weight of the urea component (A), based on the total weight of the urea components (A), in each case of one or more of the general formulae selected from the group consisting of (IIIa), (IIIb), (IIIc) and (IIId)

is present, in which
AM is a linear or branched, saturated or unsaturated, aliphatic, aromatic or aliphatic-aromatic organic radical having 2 to 50 carbon atoms,
AM1 and AM2 in each case are the same or different and are each independently a linear or branched, saturated or unsaturated, aliphatic, aromatic or aliphatic-aromatic organic radical having 1 to 50 carbon atoms, where this organic radical may also have further functional groups such as hydroxyl groups or amino groups,
IC1 and IC2 in each case are the same or different and are each independently a linear or branched, saturated or unsaturated, aliphatic, aromatic or aliphatic-aromatic hydrocarbyl radical having 2 to 40 carbon atoms,

IC3 is a linear or branched, saturated or unsaturated, aliphatic, aromatic or aliphatic-aromatic hydrocarbyl radical having 2 to 24 carbon atoms,
RP1 and RP2 in each case are the same or different and are each independently a linear or branched, saturated or unsaturated, aliphatic, aromatic or aliphatic-aromatic organic radical having 1 to 24 carbon atoms and/or a polyether radical having 1 to 120 ether oxygen atoms and/or a polyester radical having 1 to 100 ester groups and optionally containing ether groups and/or a polyamide radical having 1 to 100 amide groups and/or a polysiloxane radical having 3 to 100 silicon atoms,
RP3 are the same or different and are a linear or branched, saturated or unsaturated, aliphatic, aromatic or aliphatic-aromatic hydrocarbyl radical having 2 to 24 carbon atoms and/or a (poly)ether radical having 1 to 120 ether oxygen atoms and/or a polyamide radical having 1 to 100 amide groups and/or a polysiloxane radical having 3 to 100 silicon atoms and/or a polyester radical having 1 to 100 ester groups and optionally containing ether gro

Assignees

• Byk Chemie Gmbh
• Byk Chemie Gmbh

Inventors

• Leutfeld Daniela
• Eberhardt Marc
• Nagelsdiek René
• Bühne Sylvia
• Omeis Jürgen
• Jacobs Berthold

Classifications

• C09D5/04

  Thixotropic paints · CPC title

• C09D7/002 Primary

  Chemistry & Metallurgy · mapped topic

• C08G18/324

  containing only one aromatic ring · CPC title

• C08G18/283

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

• C08G18/2825 Primary

  having at least 6 carbon atoms · CPC title