Polybenzoxazine that can be used for coating metal and bonding of same to rubber

Patent metadata

Field	Value
Publication number	US-10549580-B2
Application number	US-201616062976-A
Country	US
Kind code	B2
Filing date	Dec 5, 2016
Priority date	Dec 16, 2015
Publication date	Feb 4, 2020
Grant date	Feb 4, 2020

Abstract

The repeat units of a polybenzoxazine comprise at least one unit corresponding to the formulae (I) or (II):

in which Z 1 represents an at least divalent, aliphatic, cycloaliphatic or aromatic bonding group comprising at least one carbon atom and optionally at least one heteroatom selected from O, S, N and P; X 1 and X 2 , which are identical or different, represent O or S; Ar 1 and Ar 2 , which are identical or different, represent a substituted or unsubstituted phenylene group; and Z 2 represents O or (S) n , the symbol “n” representing an integer equal to 1 or greater than 1. Such a polybenzoxazine can be used as metal-adhesive layer, in particular for the adhesive bonding of a metal substrate, in particular made of carbon steel, to a rubber.

First claim

The invention claimed is:

1. A polybenzoxazine, the repeat units of which comprise at least one unit corresponding to formulae (I) or (II):

in which:
Z 1 represents an at least divalent, aliphatic, cycloaliphatic or aromatic bonding group comprising at least one carbon atom and optionally at least one heteroatom selected from O, S, N and P;
X 1 and X 2 , which are identical or different, represent O or S;
Ar 1 and Ar 2 , which are identical or different, represent a substituted or unsubstituted phenylene group; and
Z 2 represents O or (S) n , n representing an integer equal to 1 or greater than 1.

2. The polybenzoxazine according to claim 1 , wherein Z 1 represents an aliphatic group comprising from 1 to 20 carbon atoms or a cycloaliphatic group comprising from 3 to 20 carbon atoms.

3. The polybenzoxazine according to claim 2 , wherein Z 1 represents an aliphatic group comprising from 1 to 16 carbon atoms or a cycloaliphatic group comprising from 3 to 16 carbon atoms.

4. The polybenzoxazine according to claim 2 , wherein Z 1 represents a C 1 -C 20 alkylene group.

5. The polybenzoxazine according to claim 2 , wherein Z 1 represents a C 1 -C 16 alkylene group.

6. The polybenzoxazine according to claim 1 , wherein Z 1 represents an aromatic group comprising from 6 to 30 carbon atoms.

7. The polybenzoxazine according to claim 1 , wherein Z 1 represents an aromatic group comprising from 6 to 20 carbon atoms.

8. The polybenzoxazine according to claim 1 , wherein Ar 1 and Ar 2 each represent an unsubstituted benzene ring.

9. The polybenzoxazine according to claim 1 , wherein X 1 and X 2 each represent S.

10. The polybenzoxazine according to claim 1 , wherein X 1 and X 2 each represent O.

11. The polybenzoxazine according to claim 9 , wherein Z 2 represents O or S.

12. The polybenzoxazine according to claim 11 , wherein Z 2 represents S.

13. The polybenzoxazine according to claim 10 , wherein Z 2 represents O or S.

14. The polybenzoxazine according to claim 13 , wherein Z 2 represents S.

15. The polybenzoxazine according to claim 10 , wherein the repeat units comprise at least one unit corresponding to formulae (I-1) or (II-1):

in which:
x is an integer varying from 1 to 16.

16. The polybenzoxazine according to claim 15 , wherein x is an integer varying from 1 to 12.

17. The polybenzoxazine according to claim 13 , wherein the repeat units comprise at least one unit corresponding to formulae (I-1) or (II-1):

in which:
x is an integer varying from 1 to 16.

18. The polybenzoxazine according to claim 17 , wherein x is an integer varying from 1 to 12.

19. A coating for a substrate, at least the surface of which is at least partially metallic, wherein the coating comprises the polybenzoxazine according to claim 1 .

20. The coating according to claim 19 , wherein the coating allows for adhesive bonding of the substrate to a rubber.

21. A substrate, at least the surface of which is at least partially metallic, wherein at least said metallic part is coated with a polybenzoxazine according to claim 1 .

22. The substrate according to claim 21 , wherein the substrate is made of steel.

23. The substrate according to claim 22 , wherein the substrate is made of carbon steel.

24. The substrate according to claim 22 , wherein the steel is a bright steel.

25. The substrate according to claim 22 , wherein the steel is at least partially coated with at least one layer of a surface metal selected from the group consisting of aluminum, copper, zinc and alloys thereof.

26. The substrate according to claim 25 , wherein the surface metal is brass.

Assignees

• Michelin & Cie

Inventors

• Fedurco Milan
• Ribezzo Marco

Classifications

• C09J179/02

  Polyamines · CPC title

• C09J161/34

  Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C09J161/04, C09J161/18 and C09J161/20 · CPC title

• B60C1/00 Primary

  Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition · CPC title

• B60C9/0007 Primary

  Reinforcements made of metallic elements, e.g. cords, yarns, filaments or fibres made from metal · CPC title

• C09D179/02

  Polyamines · CPC title