Two-component siloxane-based coatings containing polymers with urea linkages and terminal alkoxysilanes

Patent metadata

Field	Value
Publication number	US-9587143-B2
Application number	US-201514845407-A
Country	US
Kind code	B2
Filing date	Sep 4, 2015
Priority date	Oct 22, 2014
Publication date	Mar 7, 2017
Grant date	Mar 7, 2017

Abstract

A composition having: an amine-functional compound and an alkoxysilane-terminated polyurea made by reacting: an amino-functional alkoxysilane-polyisocyanate adduct with a difunctional amino- or hydroxyl compound. The composition contains no unreacted isocyanate groups. A coating composition having: an amine-functional compound, an alkoxysilane-terminated polyurea, and an epoxy- or acrylate-functional compound. The coating composition is a two-component system.

First claim

What is claimed is:

1. A composition comprising:
an amine-functional compound; and
an alkoxysilane-terminated polyurea made by reacting:
an amino-functional alkoxysilane-polyisocyanate adduct; with
a difunctional amino- or hydroxyl compound;
wherein at least 50% of the alkoxysilane-terminated polyurea molecules have a molecular weight of less than 3000; and
wherein the composition contains no unreacted isocyanate groups.

2. The composition of claim 1 , wherein the composition further comprises one or more of a catalyst, a reactive diluent, a solvent, or an additive.

3. The composition of claim 1 , wherein the amine-functional compound is a monoamine, diamine, or triamine.

4. The composition of claim 1 , wherein the amine-functional compound is an amino-functional polydimethylsiloxane, an amino-functional polydimethyldiphenylsiloxane, 3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropylmethyldiethoxysilane, 1-aminomethyltrimethoxysilane, an aliphatic monoamine, an aliphatic diamine, a cycloaliphatic diamine, or an amino-functional polyether.

5. The composition of claim 1 , wherein the alkoxysilane-terminated polyurea is a compound having the general structure:
{[(R 1 O) a R 1 3-a Si—(CH 2 ) 3 —NR 2 —CO—NH] n —R 3 —NH—CO—X} 2 —R 5 ;

wherein a is 1, 2, or 3;
wherein n is a positive integer;
wherein X is —NR 4 — or —O—;
wherein each R 1 group is an independently selected alkyl group;
wherein each R 2 and R 4 is independently selected from hydrogen, aryl, alkyl, cycloalkyl, ester-containing aliphatic, ester-containing fluorinated aliphatic, amide-containing aliphatic, and polysiloxane;
wherein R 3 is a residue of an aliphatic, cycloaliphatic, or aromatic polyisocyanate having n+1 isocyanate groups; and
wherein R 5 comprises a group selected from aliphatic, cycloaliphatic, aromatic, polyester, polyether, polysulfide, polyurethane, polycarbonate, polysiloxane, and any combination thereof.

6. The composition of claim 1 , wherein the amino-functional alkoxysilane is N-butyl-3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropylmethyldiethoxysilane, N-methyl-3-aminopropyltrimethoxysilane, or N-[3-(trimethoxysilyl)propyl]-β-alanine butyl ester.

7. The composition of claim 1 , wherein the polyisocyanate is hexamethylene diisocyanate, a homopolymer of hexamethylene diisocyanate, toluene diisocyanate, methylene diphenyl diisocyanate, or a mixture thereof.

8. The composition of claim 1 , wherein the difunctional amino- or hydroxyl compound is aspartic acid, N,N′-(2-methyl-1,5-pentanediyl)bis-1,1′,4,4′-tetraethyl ester; an unsaturated polyester, a caprolactone-based polyester; or a hydroxyl-propyl terminated polydimethylsiloxane.

9. A method comprising:
providing a first composition comprising:
an amine-functional compound; and
an alkoxysilane-terminated polyurea made by reacting:
an amino-functional alkoxysilane-polyisocyanate adduct; with
a difunctional amino- or hydroxyl compound;
wherein the first composition contains no unreacted isocyanate groups;

providing a second composition comprising an epoxy- or acrylate-functional compound;
wherein the second composition contains no unreacted isocyanate groups;

mixing the first composition with the second composition to form a mixture;
applying the mixture to a surface; and
allowing the mixture to cure to a coating.

10. The method of claim 9 , wherein the second composition further comprises one or more of a reactive diluent, a pigment, a filler, a solvent, or an additive.

11. The method of claim 9 , wherein the amount of the alkoxysilane-terminated polyurea in the mixture is up to 50 wt % of the mixture.

12. The method of claim 9 , wherein the epoxy- or acrylate-functional compound is an epoxy-functional dimethylpolysiloxane, an epoxy-functional polydimethyldiphenylsiloxane, an aliphatic epoxy, a cycloaliphatic epoxy, an acrylate-functional dimethylpolysiloxane, or 1,6-hexanedioldiacrylate.

13. The method of claim 9 , wherein the mixture is cured by one more of:
hydrolysis and condensation of alkoxysilane groups; and
amine/epoxy or amine/acrylate reactions.

14. The coating made by the method of claim 9 , wherein at least 50% of the alkoxysilane-terminated polyurea molecules have a molecular weight of less than 3000.

15. The coating of claim 14 , wherein the amount of the alkoxysilane-terminated polyurea in the mixture is up to 50 wt % of the mixture.

16. The coating of claim 14 , wherein the amine-functional compound is an amino-functional polydimethylsiloxane, an amino-functional polydimethyldiphenylsiloxane, 3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropylmethyldiethoxysilane, 1-aminomethyltrimethoxysilane, an aliphatic diamine, a cycloaliphatic diamine, or an amino-functional polyether.

17. The coating of claim 14 , wherein the alkoxysilane-terminated polyurea is a compound having the general structure:
{[(R 1 O) a R 1 3-a Si—(CH 2 ) 3 —NR 2 —CO—NH] n —R 3 —NH—CO—X} 2 —R 5 ;

wherein a is 1, 2, or 3;
wherein n is a positive integer;
wherein X is —NR 4 — or —O—;
wherein each R 1 group is an independently selected alkyl group;
wherein each R 2 and R 4 is independently selected from hydrogen, aryl, alkyl, cycloalkyl, ester-containing aliphatic, ester-containing fluorinated aliphatic, amide-containing aliphatic, and polysiloxane;
wherein R 3 is a residue of an aliphatic, cycloaliphatic, or aromatic polyisocyanate having n+1 isocyanate groups; and
wherein R 5 comprises a group selected from aliphatic, cycloaliphatic, aromatic, polyester, polyether, polysulfide, polyurethane, polycarbonate, polysiloxane, and any combination thereof.

18. The coating of claim 14 , wherein the amino-functional alkoxysilane is N-butyl-3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropylmethyldiethoxysilane, N-methyl-3-aminopropyltrimethoxysilane, or N-[3-(trimethoxysilyl)propyl]-β-alanine butyl ester.

19. The coating of claim 14 , wherein the polyisocyanate is hexamethylene diisocyanate, a homopolymer of hexamethylene diisocyanate, toluene diisocyanate, methylene diphenyl diisocyanate, or a mixture thereof.

20. The coating of claim 14 , wherein the difunctional amino- or hydroxyl compound is aspartic acid, N,N′-(2-methyl-1,5-pentanediyl)bis-1,1′,4,4′-tetraethyl ester; an unsaturated polyester, a caprolactone-based polyester, or a hydroxyl-propyl terminated polydimethylsiloxane.

21. The coating of claim 14 , wherein the epoxy- or acrylate-functional compound is an epoxy-functional dimethylpolysiloxane, an epoxy-functional polydimethyldiphenylsiloxane, an aliphatic epoxy, a cycloaliphatic epoxy, an acrylate-functional dimethylpolysiloxane, or 1,6-hexanedioldiacrylate.

22. The coating of claim 14 , wherein the mixture is cured by one or more of:
hydrolysis and condensation of alkoxysilane groups; and
amine/epoxy or amine/acrylate reactions.

23. A kit comprising:
a first container containing a first composition comprising:
an amine-functional compound; and
an alkoxysilane-terminated polyurea made by reacting:
an amino-functional alkoxysilane-polyisocyanate adduct; with
a difunctional amino- or hydroxyl compound;
wherein the first composition contains no unreacted isocyanate groups; and

a second container containing a second composition comprising an epoxy- or acrylate-functional compound;
wherein the second cont

Assignees

• Iezzi Erick B
• Us Navy

Inventors

• Iezzi Erick B

Classifications

• C08G18/3228

  acyclic · CPC title

• C09D5/30

  Camouflage paints · CPC title

• C08G18/837

  by silicon containing compounds · CPC title

• C08G18/61

  Polysiloxanes · CPC title

• C08G18/798

  containing urethdione groups · CPC title