IP Library Granted Patent US 8,119,245
Granted Patent B2
US 8,119,245 · App. 12/012,715 · Granted Feb 21, 2012

Dual-cure coating compositions based on polyaspartates polyisocyanates and acrylate-containing compounds

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Quick Facts
Patent No.
US 8,119,245
App. No.
12/012,715
Granted
Feb 21, 2012
Kind
B2
Abstract

A radiation-curable coating composition is provided. The composition comprises a) an amino-functional polyaspartate; b) a (cyclo) aliphatic polyisocyanate; c) an acrylate-functional compound; and d) a photoinitiator. Substrates coated with the coating compositions are also provided.

Claims (27)

1. A radiation-curable coating composition comprising

a) an amino-functional polyaspartate;

b) a (cyclo) aliphatic polyisocyanate;

c) a urethane acrylate; and

d) a photoinitiator,

wherein the urethane acrylate is essentially free from hydroxyl and isocyanate groups, and the amount of the urethane acrylate comprises 30 wt. %-85 wt. % of the composition.

2. The coating composition of claim 1 , wherein the NCO:NH ratio of (a) to (b) is from 0.5 NCO:1 NH to 3 NCO:1 NH.

3. The coating composition of claim 1 , wherein the amount of polyaspartate (a) and polyisocyanate (b) together comprise 15 wt. % to 70 wt. % of the composition, and the amount of photoinitiator (d) comprises 0.3 wt. % to 10 wt. % of the composition, based on the weight of the coating composition.

4. The coating composition of claim 1 , wherein the amount of a) and b) combined is from 55 wt. %-65 wt. % and the amount of c) is from 35 wt. %-45 wt. %, based on the weight of the coating composition.

5. The composition of claim 1 , wherein (a), the amino-functional polyaspartate corresponds to Formula I,

where X represents an n-valent organic group obtained by removing the primary amino groups from an n-valent polyamine, R 1 , R 2 represent the same or different organic groups, which are inert to isocyanate groups under the reaction conditions, and n represents an integer of at least 2.

6. The coating composition of claim 1 , wherein the one or more polyisocyanates contain urethane, uretdione, allophanate, biuret, iminooxadiazindione and/or isocyanurate groups and have an NCO group content of 5 to 25% by weight, an average NCO functionality of 2.0 to 5.0, and a residual amount of monomeric diisocyanates of below 1% by weight.

7. The coating composition of claim 6 , wherein the NCO functionality is 2.8 to 4.0.

8. The composition of claim 6 , wherein the residual amount of monomeric isocyanates is below 0.5% by weight.

9. The coating composition of claim 1 , wherein the urethane acrylate is the reaction product of one or more isocyanurate-containing polyisocyanates and one or more compounds containing at least one isocyanate-reactive group and at least one olefinic double bond.

10. The coating composition of claim 9 , wherein the compounds containing at least one isocyanate-reactive group and at least one olefinic double bond are selected from the group consisting of hydroxymethyl(meth)acrylate (HEA), hydroxypropyl(meth)acrylate (HPA), trimethylol propane di(meth)acrylate, pentaerythritol tri(meth)acrylate, (meth)acrylic acid adduct of glycidyl(meth)acrylate or a polycaprolactone hydroxy ethyl(meth)acrylate.

11. The coating composition of claim 1 , further comprising a reactive diluent.

12. The coating composition of claim 11 , wherein the reactive diluent is hexane diol diacrylate, and the reactive diluent is present in amounts of between 2.5 wt. % to 15 wt. %, based on the weight of the total coating composition.

13. The coating composition of claim 1 , further including one or more acrylate-functional polyisocyanates.

14. The coating composition of claim 13 , wherein the acrylate-functional polyisocyanate is the reaction product of one or more monohydric alcohols containing (meth)acryloyl groups and one or more di- or polyisocyanates, the equivalent ratio of NCO groups to OH groups being 1:0.2 to 1:0.8.

15. The coating composition of claim 13 , further comprising one or more additives.

16. A substrate coated with the coating composition of claim 13 .

17. The substrate of claim 16 , wherein the substrate is asphalt.

18. The substrate of claim 16 , wherein the substrate is a concrete surface.

19. The substrate of claim 16 , wherein the substrate is an interior or exterior surface of a building.

20. The substrate of claim 16 , wherein the cure is effected by exposure to actinic radiation.

21. The substrate of claim 20 , wherein the source of actinic radiation is sunlight.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 6, 2018
From: ALLNEX HOLDING INTERNATIONAL B.V.
To: ALLNEX NETHERLANDS B.V.
Reel/Frame 047249/0918 →
MERGER Recorded Apr 26, 2018
From: ALLNEX IP S.A.R.L.
To: ALLNEX HOLDING INTERNATIONAL B.V.
Reel/Frame 046022/0610 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 3, 2014
From: BAYER MATERIALSCIENCE LLC
To: ALLNEX IP S.À.R.L.
Reel/Frame 032596/0902 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 5, 2008
From: KENDI, MARGARET A.; WAYT, TERRELL D.
To: BAYER MATERIALSCIENCE LLC
Reel/Frame 020535/0284 →