Polyurethane coating compositions

Patent metadata

Field	Value
Publication number	US-10590229-B2
Application number	US-201615574036-A
Country	US
Kind code	B2
Filing date	May 17, 2016
Priority date	May 21, 2015
Publication date	Mar 17, 2020
Grant date	Mar 17, 2020

Abstract

The present invention relates to non-aqueous coating agent compositions, containing at least one polyol (A), at least one silane-modified compound (B) of formula (I), optionally one or more silane-free aliphatic or cycloaliphatic polyisocyanates (C) having free or blocked isocyanate groups, and at least one catalyst (D) for the cross-linking of the silane groups. Furthermore, the non-aqueous coating agent compositions according to the invention can contain one or more surface additives (E) and one or more non-aqueous solvents (F).

First claim

The invention claimed is:

1. A nonaqueous coating material composition comprising
(A) at least one polyol (A),
(B) at least one tertiary formamidosilane-containing compound of the formula (I);

where in the formula (I):
X is an optionally substituted, linear or branched, aliphatic or alicyclic organic molecule residue;
R 1 is an at least divalent, optionally substituted, linear or branched, aliphatic and/or alicyclic structural unit having 1 to 12 carbon atoms, optionally one or more nonadjacent methylene groups is replaced in each case by 0 or S;
R 2 and R 3 each independently of one another are an optionally substituted, linear or branched, aliphatic and/or alicyclic group having 1 to 12 carbon atoms; and
n is an integer from 0 to 2;

(C) optionally one or more silane-free aliphatic or cycloaliphatic polyisocyanates having free or blocked isocyanate groups,
at least one of the two components (B) and (C) comprises free or blocked isocyanate groups;
(D) at least one catalyst for the crosslinking of the silane groups of component (B);
(E) optionally one or more flow control assistants; and
(F) optionally one or more nonaqueous solvents,
wherein the coating material composition consists of components (A), (B), (C), (D), (E) and (F), wherein component (A) is a polyacrylate polyol, and wherein (C) is an aliphatic polyisocyanate resin based on trimers of hexamethylene diisocyanate having an NCO functionality of 2.8 to 3.6.

2. The coating material composition as claimed in claim 1 , wherein component (B) is a tertiary formamidosilane-containing compound of the formula (II):

where in the formula (II)
Z is a molecule residue which consists of a polyisocyanate or an NCO-containing polyurethane prepolymer, at least one NCO group of the stated structures in (i) or (ii) being modified, per molecule, with a secondary formamidosilane so that a compound of the formula (II) is formed; and
R 1 , R 2 , R 3 and n are as defined in claim 1 .

3. The coating material composition as claimed in claim 2 , wherein the tertiary formamidosilane-containing component (B) is a polyurethane prepolymer which contains no further free or blocked NCO groups.

4. The coating material composition as claimed in claim 2 , wherein the tertiary formamidosilane-containing component (B) is a polyurethane prepolymer which consists of a polyurethane prepolymer based on hexamethylene diisocyanate (HDI) and a polyol, such as 2,2,4-trimethylpentane-1,3-diol, all NCO groups in the polyurethane prepolymer being modified with a secondary formamidosilane, to form a compound of the formula (II).

5. The coating material composition as claimed in claim 2 , wherein component (B) is a tertiary formamidosilane of the formulae I or II which is reduced by at least one-NCO group an aliphatic or alicyclic, substituted or unsubstituted polyisocyanate based on a representative selected from tetramethylene 1,4-diisocyanate, pentane 1,5-diisocyanate, hexamethylene 1,6-diisocyanate, 2,2,4-trimethylhexane 1,6-diisocyanate, ethylene diisocyanate, dodecane 1,12-diisocyanate, 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl isocyanate (isophorone diisocyanate, IPDI) and mixtures of the aforesaid polyisocyanates, the isomeric bis(4,4′-isocyanatocyclohexyl)methanes, and also mixtures thereof, the isocyanates being present in each case as monomer, dimer, trimer and/or a polyisocyanate parent structure obtained by urethane, biuret, uretdione and/or allophanate formation.

6. The coating material composition as claimed in claim 1 , wherein
(i) R 1 is a divalent propylene group (—CH 2 —CH 2 —CH 2 —),
R 3 is -methyl or -ethyl and n=0; or

(ii) R 1 is a divalent propylene group (—CH 2 —CH 2 —CH 2 —); or
(iii) R 2 and R 3 each independently of one another are -methyl or -ethyl; or
(iv) R 1 is a divalent hexylene group (—CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 —).

7. The coating material composition as claimed in claim 1 , wherein the tertiary formamidosilane-containing component (B) possesses an average NCO functionality of 2.0 to 5.0, and an isocyanate group content of 5.0 to 50.0 wt %, based on component (B).

8. The coating material composition as claimed in claim 1 , wherein the tertiary formamidosilane-containing component (B) is an aliphatic polyisocyanate resin based on hexamethylene diisocyanate (HDI) and reduced by at least one —NCO group.

9. The coating material composition as claimed in claim 1 , wherein (i) component (B) contains blocked or free isocyanate groups and component (C) is present, or (ii) component (B) contains no blocked or free isocyanate groups and component (C) is present.

10. An automobile clearcoat or topcoat material comprising a coating material composition as claimed in claim 1 .

11. A vehicle body or bodywork component bearing an applied crosslinked coating material composition as claimed in claim 1 .

12. A nonaqueous coating material composition comprising
(A) at least one polyacrylate polyol (A),
(B) at least one tertiary formamidosilane-containing compound of the formula (I);

where in the formula (I):
X is an optionally substituted, linear or branched, aliphatic or alicyclic organic molecule residue;
R 1 is an at least divalent, optionally substituted, linear or branched, aliphatic and/or alicyclic structural unit having 1 to 12 carbon atoms, optionally one or more nonadjacent methylene groups is replaced in each case by O or S;
R 2 and R 3 each independently of one another are an optionally substituted, linear or branched, aliphatic and/or alicyclic group having 1 to 12 carbon atoms; and
n is an integer from 0 to 2;

(C) optionally one or more silane-free aliphatic or cycloaliphatic polyisocyanates having free or blocked isocyanate groups,
at least one of the two components (B) and (C) comprises free or blocked isocyanate groups;
(D) at least one catalyst for the crosslinking of the silane groups of component (B);
(E) optionally one or more flow control assistants; and
(F) optionally one or more nonaqueous solvents,
wherein (B) is an NCO-free polyurethane based on monomeric HDI, 2,2,4-trimethylpentane-1,3-diol and N-(3-trimethoxysilylpropyl)formamide) or N-(3-Methyldimethoxysilylpropyl)formamide or N-(3-Triethoxysilylpropyl)formamide or N-(3-Methyldiethoxysilylpropyl)formamide, and (C) is an aliphatic polyisocyanate resin based on trimers of HDI having an NCO functionality of 2.8 to 4.5, or
wherein (B) is an NCO-free polyurethane based on an aliphatic polyisocyanate resin based on trimers of HDI having an NCO functionality of 2.8 to 4.5 and N-(3-trimethoxysilylpropyl)formamide) or N-(3-Methyldimethoxysilylpropyl)formamide or N-(3-Triethoxysilylpropyl)formamide or N-(3-Methyldiethoxysilylpropyl)formamide, and (C) is an aliphatic polyisocyanate resin based on trimers of HDI having an NCO functionality of 2.8 to 4.5, or
wherein (B) is an NCO-free polyurethane based on an aliphatic polyisocyanate resin based on trimers of HDI having an NCO functionality of 2.8 to 4.5 and N-(3-trimethoxysilylpropyl)formamide) or N-(3-Methyldimethoxysilylpropyl)formamide or N-(3-Triethoxysilylpropyl)formamide or N-(3-Methyldiethoxysilylp

Assignees

• Covestro Deutschland Ag

Inventors

• Köcher Jürgen
• Hebestreit Tanja
• Eggert Christoph

Classifications

• C08G18/792

  formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates · CPC title

• C08G18/3206

  aliphatic · CPC title

• C09D175/04

  Polyurethanes · CPC title

• C08G18/10

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

• C08G18/3893

  containing silicon · CPC title