IP Library Granted Patent US 10,626,291
Granted Patent B2
US 10,626,291 · App. 14/787,696 · Granted Apr 21, 2020

Crosslinking of IPMS adducts with aminosilanes

Inventors: Markus Hallack (Schermbeck, DE); Andrea Biebel (Darmstadt, DE)
Assignee: Evonik Operations, GmbH
C09D175/04C08G18/10C08G18/12C08G18/24C08G18/289C08G18/718C08G18/8009C08G18/8064
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Quick Facts
Patent No.
US 10,626,291
App. No.
14/787,696
Granted
Apr 21, 2020
Kind
B2
Abstract

The present invention relates to coating materials at least comprising A) an adduct of isocyanatosilanes with hydroxy-functional compounds, B) a tin-containing compound and C) an aminosilane, to the use of the coating materials and also to the coatings obtained.

Claims (28)

1. A coating material, comprising:

A) from 10-90 wt. % based on the total weight of the coating material of an adduct of at least one isocyanatosilane with at least one hydroxy-functional compound;

B) a tin-containing compound of the formula

R 1 4−a SnX a ,

wherein:

a is 1, 2, or 3,

R 1 independently is selected from the group consisting of a linear or branched optionally substituted C1-C30 alkyl group, C5-C14 cycloalkyl group, C6-C14 aryl group, triorganylsilyl group, and C1-C30 diorganylalkoxysilyl group, and

X is selected from the group consisting of halogen, —OR 2 , —OC(O)R 3 , —OH, —SR 4 , —NR 5 2 , —NHR 6 , —OSiR 7 3 , —OSi(OR 8 ) 3 , in which the substituents R 2 to R 8 in each case independently of one another are selected from an optionally substituted C1-C8 alkyl, C6-C14 aryl and/or C2-C8 alkenyl group; and

C) from 10 to 20 wt. %, based on the total weight of the coating material, of an aminosilane

wherein said at least one hydroxyl-functional compound is at least one compound selected from the group consisting of a diol having 1 to 22 carbon atoms, a triol having 1 to 22 carbon atoms and a tetrol having 1 to 22 carbon atoms; and

wherein said at least one hydroxyl-functional compound and said adduct are not a polyether.

2. The coating material of claim 1 , wherein the isocyanatosilane is a compound of the formula (I):

OCN-(alkyl)-Si(alkoxy) 3   (I),

wherein

alkyl represents a linear or branched alkylene chain having 1-4 carbon atoms; and

alkoxy independently represents a methoxy, ethoxy, propoxy, or butoxy group.

3. The coating material of claim 1 , wherein a ratio of OH groups from the at least one hydroxy-functional compound to NCO groups from the at least one isocyanatosilane is from 0.8:1 to 1.2:1.

4. The coating material of claim 1 , wherein the tin-containing compound is at least one selected from the group consisting of di-n-butyltin dichloride, di-n-octyltin dichloride, di-n-butyltin oxide, di-n-octyltin oxide, di-n-butyltin diacetate, di-n-butyltin dilaurate, di-n-butyltin maleate, di-n-butyltin bis-2-ethylhexanoate, di-n-butyltin dineodecanoate, di-n-octyltin diacetate, di-n-octyltin dilaurate, di-n-octyltin maleate, di-n-octyltin bis-2-ethylhexanoate, di-n-octyltin dineodecanoate, and di-n-butyltin diacetylacetonate.

5. The coating material of claim 1 , wherein the aminosilane comprises aminosilane or aminoalkylsilane of the formula (III):

A m SiY n   (III),

wherein:

A is a substituted or unsubstituted aminoalkyl group, a substituted or unsubstituted diaminodialkyl group or substituted or unsubstituted triaminotrialkyl group,

Y each independently represents OH, ONa, OK, OR′, OCOR′, OSiR′ 3 , Cl, Br, I, or NR′ 2 ,

m is 1 or 2,

n is 1, 2, or 3, with the proviso that m+n=4, and

R′ each independently represents hydrogen, a linear or branched alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, or heteroaryl group, having in each case 1 to 18 C atoms and may in each case optionally be substituted.

6. The coating material of claim 1 , further comprising a binder component, auxiliary, adjuvant, and/or solvent.

7. The coating material of claim 1 , wherein the ratio of OH groups from the at least one hydroxy-functional compound to NCO groups from the at least one isocyanatosilane is from 0.9:1 to 1.1:1.

Assignments (2)
CHANGE OF NAME Recorded Nov 18, 2019
From: EVONIK DEGUSSA GMBH
To: EVONIK OPERATIONS GMBH
Reel/Frame 051045/0872 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 28, 2015
From: HALLACK, MARKUS; BIEBEL, ANDREA
To: EVONIK DEGUSSA GMBH
Reel/Frame 036905/0694 →
Priority Claims (1)
DE 10 2013 208 356 · May 7, 2013 · national
Continuity (1)
Related Publication 20160108280A1 · Apr 21, 2016
Cited By (4)
US 12,404,407 US 12,473,654 US 12,577,460 US 12,624,283