Colour-stable curing compositions containing polyisocyanates of (cyclo)aliphatic diisocyanates

Patent metadata

Field	Value
Publication number	US-11624003-B2
Application number	US-201816647792-A
Country	US
Kind code	B2
Filing date	Sep 11, 2018
Priority date	Sep 20, 2017
Publication date	Apr 11, 2023
Grant date	Apr 11, 2023

Abstract

The present invention relates to novel color drift-stable compositions of polyisocyanates of (cyclo)aliphatic diisocyanates.

First claim

The invention claimed is:

1. A polyisocyanate composition comprising
(A) at least one polyisocyanate obtained by reacting at least one monomeric (cyclo)aliphatic isocyanate selected from the group consisting of hexamethylene diisocyanate, pentamethylene diisocyanate, isophorone diisocyanate, 1,3-bis(isocyanatomethyl)cyclohexane, 4,4′-di(isocyanatocyclohexyl)methane and 2,4′-di(isocyanatocyclohexyl)methane, wherein the at least one polyisocyanate has an NCO content of at least 15% by weight,
(B) at least one silyl ester selected from the group of silyl phosphates and silyl phosphonates in an amount of 0.2 to 300 ppm by weight, based on component (A),
(C) at least one sterically hindered phenol having exactly one phenolic hydroxyl group per aromatic ring, and wherein at least one ortho position, relative to the phenolic hydroxyl group, bears a tert-butyl group,
(D) at least one Lewis-acidic organic metal compound capable of accelerating the reaction of isocyanate groups with isocyanate-reactive groups,
(E) at least one solvent,
(F) optionally at least one further antioxidant, and
(G) optionally other coatings additives;
wherein the at least one silyl ester (B) is a tris(silyl) phosphate.

2. The polyisocyanate composition according to claim 1 , wherein the at least one silyl ester (B) is present in an amount of 10 to 300 ppm by weight, based on component (A).

3. A polyisocyanate composition comprising
(A) at least one polyisocyanate obtained by reacting at least one monomeric (cyclo)aliphatic isocyanate, wherein the at least one polyisocyanate has an NCO content of at least 15% by weight,
(B) at least one silyl ester selected from the group of silyl phosphates and silyl phosphonates in an amount of 0.2 to 300 ppm by weight, based on component (A),
(C) at least one sterically hindered phenol,
(D) at least one Lewis-acidic organic metal compound capable of accelerating the reaction of isocyanate groups with isocyanate-reactive groups,
(E) at least one solvent,
(F) optionally at least one further antioxidant, and
(G) optionally other coatings additives;
wherein the at least one polyisocyanate (A) has been prepared using a catalyst based on ammonium carboxylate, ammonium α-hydroxyalkylcarboxylate or ammonium hydroxide.

4. The polyisocyanate composition according to claim 1 , wherein the at least one Lewis-acidic organic metal compound (D) comprises a metal selected from the group consisting of tin, zinc, titanium, zirconium and bismuth.

5. The polyisocyanate composition according to claim 1 , wherein the weight ratio of the at least one polyisocyanate (A) to the at least one solvent (E) is 9:1 to 2:8.

6. The polyisocyanate composition according to claim 1 , wherein the at least one solvent (E) is selected from the group consisting of aromatic hydrocarbons, (cyclo)aliphatic hydrocarbons, ketones, esters, ethers, ether esters and carbonates.

7. The polyisocyanate composition according to claim 1 , wherein the at least one further antioxidant (F) is present and is selected from the group of phosphites, phosphonates, phosphonites and thioethers.

8. A process for stabilizing polyisocyanate compositions according to claim 1 , the process comprising:
adding at least one silyl ester (B) in an amount of 0.2 to 300 ppm by weight based on component (A), at least one sterically hindered phenol (C), at least one Lewis-acidic organic metal compound (D), at least one solvent (E), optionally at least one further antioxidant (F) and optionally other coatings components (G) to the at least one polyisocyanate (A).

9. A process for producing polyurethane coatings, comprising:
reacting a polyisocyanate composition according to claim 1 with at least one binder comprising isocyanate-reactive groups.

10. A process for producing polyurethane coatings, comprising:
reacting a polyisocyanate composition according to claim 1 with at least one binder selected from the group consisting of polyacrylate polyols, polyester polyols, polyether polyols, polyurethane polyols, polyurea polyols, polyetherols, polycarbonates, polyester polyacrylate polyols, polyester polyurethane polyols, polyurethane polyacrylate polyols, polyurethane-modified alkyd resins, fatty acid-modified polyester polyurethane polyols, copolymers with allyl ethers and copolymers or graft polymers thereof.

11. A process, comprising employing a polyisocyanate composition according to claim 1 as curing agent in coating materials in primers, primer surfacers, pigmented topcoats, basecoats and clearcoats in the sectors of automotive refinishing or large vehicle finishing, or in utility vehicles in the agricultural and construction sector.

12. The polyisocyanate composition according to claim 1 , wherein the at least one (cyclo)aliphatic isocyanate is hexamethylene diisocyanate.

13. The polyisocyanate composition according to claim 1 , wherein the at least one sterically hindered phenol (C) is selected from the group consisting of 2,6-bis-tert-butyl-4-methylphenol (BHT), 3-[3,5-di-tert-butyl-4-hydroxyphenyl] propionate, pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate, 3,3′,3″,5,5′,5″-hexa-tert-butyl-a, a′,a″-(mesitylene-2,4,6-triyl)tri-p-cresol, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, isooctyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate and octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate.

14. The polyisocyanate composition according to claim 1 , wherein the at least one sterically hindered phenol (C) is selected from the group consisting of 2,6-di-tert-butyl-4-methylphenol (BHT); isooctyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate and pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate.

Assignees

• Basf Se

Inventors

• Schaefer Harald
• Genger Thomas
• Emmerling Sebastian

Classifications

• C08K5/56

  Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond · CPC title

• C08G18/73

  acyclic · CPC title

• C08G18/022

  the polymeric products containing isocyanurate groups · CPC title

• C08G18/836

  by phosphorus containing compounds · CPC title

• C08K5/134

  Phenols containing ester groups · CPC title