Process for preparing water-emulsifiable polyurethane acrylates

Patent metadata

Field	Value
Publication number	US-10294392-B2
Application number	US-201415029817-A
Country	US
Kind code	B2
Filing date	Oct 13, 2014
Priority date	Oct 16, 2013
Publication date	May 21, 2019
Grant date	May 21, 2019

Abstract

The present invention relates to storage-stable water-emulsifiable polyurethane acrylates, to a process for preparation thereof and to the use thereof.

First claim

The invention claimed is:

1. A coating composition, comprising:
a urethane (meth)acrylate (A) comprising, as formation components:
(a) at least one isocyanate having at least 2 isocyanate functions,
(b) at least one polyalkylene oxide polyether having at least 2 hydroxyl functions,
(c) at least one hydroxy-functional (meth)acrylate having exactly one hydroxyl function and at least one (meth)acrylate function,
(d) at least one compound having at least one isocyanate-reactive group and at least one acid function,
(e) optionally at least one compound having at least one isocyanate-reactive group and at least one basic group for neutralization of the acid groups of component (d),
(f1) at least one monofunctional polyalkylene oxide polyether alcohol having a number-average molecular weight Mn of at least 600 g/mol,
(f2) optionally at least one monoalcohol (f2) having exactly one hydroxyl function and no further functional group beyond that,
(g) optionally at least one di- or polyamine, and
(h) optionally at least one primary or secondary amine (h) for activation of the (meth)acrylate group.

2. The coating composition according to claim 1 , wherein the isocyanate (a) is a (cyclo)aliphatic diisocyanate.

3. The coating composition according to claim 1 , wherein component (b) comprises alkoxylated di- or polyols of formula (Ia) to (Id)

wherein
R 1 and R 2 are each independently hydrogen, or C 1 -C 18 -alkyl optionally substituted by aryl, alkyl, aryloxy, alkyloxy, heteroatoms and/or heterocycles,
k, I, m, q are each independently an integer from 1 to 15, and
each X i for i=1 to k, 1 to l, 1 to m and 1 to q is independently be selected from the group consisting, of —CH 2 —CH 2 —O—, —CH 2 —CH(CH 3 )—O—, —CH(CH 3 )—CH 2 —O—, —CH 2 —C(CH 3 ) 2 —O—, —C(CH 3 ) 2 —CH 2 —O—, —CH 2 —CHVin-O—, —CHVin-CH 2 —O—, —CH 2 —CHPh-O— and CHPh-CH 2 —O—, in which Ph is phenyl and Vin is vinyl.

4. The coating composition according to claim 1 , wherein component (b) is a polyalkylene glycol of formula
HO—[—X i —] n —H

wherein
X i for each i=1 to n is independently be selected from the group consisting of —CH 2 —CH 2 —O—, —CH 2 —CH(CH 3 )—O—, and —CH(CH 3 )—CH 2 —O—, and
n may be an integer from 5 to 60.

5. The coating composition according to claim 1 , wherein component (c) is selected from the group consisting of 2-hydroxyethyl (meth)acrylate, 2- or 3-hydroxypropyl (meth)acrylate, 1,4-butanediol mono(meth)acrylate, neopentyl glycol mono(meth)acrylate, 1,5-pentanediol mono(meth)acrylate, 1,6-hexanediol mono(meth)acrylate, glyceryl di(meth)acrylate, trimethylolpropane di(meth)acrylate, pentaerythrityl tri(meth)acrylate, 2-hydroxyethyl(meth)acrylamide, 2-hydroxypropyl(meth)acrylamide, and 3-hydroxypropyl(meth)acrylamide and mixtures thereof.

6. The coating composition according to claim 1 , wherein a component (d) is selected from the group consisting of mercaptoacetic acid (thioglycolic acid), mercaptopropionic acid, mercaptosuccinic acid, hydroxyacetic acid, hydroxypropionic acid (lactic acid), hydroxysuccinic acid, hydroxypivalic acid, dimethylolpropionic acid, dimethylolbutyric acid, hydroxydecanoic acid, hydroxydodecanoic acid, 12-hydroxystearic acid, hydroxyethanesulfonic acid, hydroxypropanesulfonic acid, mercaptoethanesulfonic acid, mercaptopropanesulfonic acid, aminoethanesulfonic acid, aminopropanesulfonic acid, glycine (aminoacetic acid), N-cyclohexylaminoethanesulfonic acid, N-cyclohexylaminopropanesulfonic acid, iminodiacetic acid, ammonium or alkali metal salts of 6-amino-4-azahexanecarboxylic acid (N-(2′-carboxyethyl)ethylenediamine) and 5-amino-3-azapentanesulfonic acid (N-(2′-sulfoethyl)ethylenediamine) and mixtures thereof.

7. The coating composition according to claim 1 , wherein component (f1) has formula
R 3 —O—[—Y i —] w —H

wherein
R 3 is independently C 1 - to C 4 -alkyl,
w is an integer from 12 to 50, and
each Y i for i=1 to w is independently be selected from the group consisting of —CH 2 —CH 2 —O—, —CH 2 —CH(CH 3 )—O—, —CH(CH 3 )—CH 2 —O—, —CH 2 —C(CH 3 ) 2 —O—, —C(CH 3 ) 2 —CH 2 —O—, —CH 2 —CHVin-O—, —CHVin-CH 2 —O—, —CH 2 —CHPh-O— and CHPh-CH 2 —O—, in which Ph is phenyl and Vin is vinyl.

8. The coating composition according to claim 1 , wherein both a compound (d) selected from the group consisting of dimethylolpropionic acid and dimethylolbutyric acid and mixtures thereof, and a compound selected from the group consisting of 6-amino-4-azahexanecarboxylic acid (N-(2′-carboxyethyl)ethylenediamine) and 5-amino-3-azapentanesulfonic acid (N-(2′-sulfoethyl)ethylenediamine) and mixtures thereof, are present.

9. The coating composition according to claim 1 , wherein the compound (g) is added to the reaction mixture when the NCO content thereof (calculated at 42 g/mol) is at least 0.2% by weight and not more than 1.5% by weight.

10. The coating composition according to claim 1 , wherein the composition optionally further comprises at least one reactive diluent (B), and wherein the urethane (meth)acrylate (A) comprises the following:
(a) 100 mol % of isocyanate functions,
(b) 25 to 75 mol % of hydroxyl functions (based on isocyanate functions in (a)),
(c) 25 to 75 mol % of hydroxyl functions (based on isocyanate functions in (a)),
(d) 0 to 30 mol % of hydroxyl functions (based on isocyanate functions in (a)),
(e) 0 to 5 mol % of isocyanate-reactive groups (based on isocyanate functions in (a)),
(f1) 5 to 10 mol % of hydroxyl functions (based on isocyanate functions in (a)),
(f2) 0 to 5 mol % of hydroxyl functions (based on isocyanate functions in (a)),
(g) 0 to 5 mol % of amino functions (based on isocyanate functions in (a)),
(h) up to 0.4 mol, of aminic hydrogen atoms of primary or secondary amino groups per 1 mol of (meth)acrylate groups in (A) and/or (B),
with the proviso that the sum total of the hydroxyl functions in components (b), (c), (d), (e) and (f) adds up to 100 mol % of hydroxyl functions (based on isocyanate functions in (a)).

11. A coating method, comprising:
coating and/or impregnating a lignin-containing substrate and/or plastics-containing substrate with the coating composition according to claim 1 .

12. A coating method, comprising:
coating wood, woodbase materials, wood-containing substrates, cellulose fibers and/or paper raw materials with the coating composition according to claim 1 .

13. A coating method, comprising:
performing adhesion priming of parquet, veneer surfaces of furniture, cork and/or compressed woodbase materials, by applying the coating composition according to claim 1 .

14. A process for preparing the coating composition according to claim 1 , comprising:
initially charging components (b), (c), (d), (f1) and, if present, (e), (f2) and/or (g) at least in part, to obtain a mixture; and
adding isocyanate (a) the mixture of initially charged components.

15. The coating composition according to claim 1 , wherein (e) is present in the composition.

16. The coating composition according to claim 1 , wherein (f2) is present in the composition.

17. The coating composition according to claim 1 , wherein (g) is present in the composition.

18. The coating composition according to claim 1 , wherein (h) is present in the composition.

19. The coating composition according to claim 1 , wherein (e), (f2), (g) and (h) are present in the composition.

20. The coating composition according to claim 1 , wherein the monofunctional pol

Assignees

• Basf Se

Inventors

• Berger Sebastian
• Thuery Peter
• Neumann Susanne
• Burkhardt Uwe

Classifications

• C08G18/672

  Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen · CPC title

• C08G18/6692

  with compounds of group C08G18/34 · CPC title

• C09D175/16 Primary

  having terminal carbon-to-carbon unsaturated bonds · CPC title

• C08G18/755

  and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate · CPC title

• C09J175/16

  having terminal carbon-to-carbon unsaturated bonds · CPC title