Sulphur-comprising polyaromatic polyamine that can be used in the synthesis of polyurea

Patent metadata

Field	Value
Publication number	US-9617372-B2
Application number	US-201314438396-A
Country	US
Kind code	B2
Filing date	Oct 16, 2013
Priority date	Oct 24, 2012
Publication date	Apr 11, 2017
Grant date	Apr 11, 2017

Abstract

A sulphur-comprising polyaromatic polyamine compound can be used as a monomer or prepolymer, when n is different from zero, in the synthesis of polyurea. The compound corresponds to the formula (I):

H 2 N—Ar 1 —NH—CH 2 —CH(OH)—(CH 2 ) m —O—Z 1 —O—(CH 2 ) m —CH(OH)—CH 2 —[X] n —HN—Ar 2 —NH 2

in which X represents the string:

—HN—Ar 3 —NH—(CH 2 )—CH(OH)—(CH 2 ) m —O—Z 2 —O—(CH 2 ) m —CH(OH)—(CH 2 )—

and in which n represents an integer equal to zero or different from zero; m, which are identical or different, represent an integer within a range from 1 to 10; Z 1 and Z 2 , which are identical or different, represent a divalent bonding group comprising from 1 to 30 carbon atoms; and Ar 1 , Ar 2 and Ar 3 , which are identical or different, each represent a phenylene group, at least one of these phenylene groups bearing one, two, three or four groups of formula —S x —R in which “x” is an integer from 1 to 8 and R represents hydrogen or a hydrocarbon group which can comprise a heteroatom and which comprises from 1 to 10 carbon atoms.

First claim

The invention claimed is:

1. A sulfur-comprising polyaromatic polyamine compound corresponding to the formula (I):
H 2 N—Ar 1 —NH—CH 2 —CH(OH)—(CH 2 ) m —O—Z 1 —O—(CH 2 ) m —CH(OH)—CH 2 —[X] n —HN—Ar 2 —NH 2

wherein X represents the string:
—HN—Ar 3 —NH—(CH 2 )—CH(OH)—(CH 2 ) m —O—Z 2 —O—(CH 2 ) m —CH(OH)—(CH 2 )—;

wherein n represents an integer equal to zero or different from zero;
wherein m, which are identical or different, represent an integer within a range from 1 to 10;
wherein Z 1 and Z 2 represent cyclohexane-1,4-dimethylene;
wherein Ar 1 , Ar 2 and Ar 3 , which are identical or different, each represent a phenylene group, at least one of these phenylene groups bearing one, two, three or four groups of formula —S x —R in which x is an integer from 1 to 8 and R represents hydrogen or a hydrocarbon group which optionally comprises a heteroatom and which comprises from 1 to 10 carbon atoms.

2. The compound according to claim 1 , wherein n is equal to 1.

3. The compound according to claim 1 , wherein n is within a range from 2 to 20.

4. The compound according to claim 3 , wherein n is within a range from 2 to 10.

5. The compound according to claim 1 , wherein m, which are identical or different, represent an integer within a range from 1 to 5.

6. The compound according to claim 5 , wherein m, which are identical or different, represent an integer equal to 1 or 2.

7. The compound according to claim 6 , wherein m is preferably equal to 1.

8. The compound according to claim 1 , wherein each of the Ar 1 , Ar 2 and Ar 3 groups bears one, two, three or four groups of formula —S x —R.

9. The compound according to claim 1 , wherein x is within a range from 1 to 4.

10. The compound according to claim 9 , wherein x is equal to 1 or 2.

11. The compound according to claim 1 , wherein R is an alkyl.

12. The compound according to claim 11 , wherein R is an alkyl having from 1 to 5 carbon atoms.

13. The compound according to claim 12 , wherein R represents a methyl or an ethyl.

14. The compound according to claim 13 , wherein R is a methyl.

15. The compound according to claim 1 , wherein the monovalent phenylenediamino strings H 2 N—Ar 1 —NH— and —HN—Ar 2 —NH 2 , which are identical or different, correspond to one of the formulae (III-a), (III-b) and (III-c):

16. The compound according to claim 1 , wherein the divalent phenylenediamino strings —HN—Ar 3 —NH—, which are identical or different, correspond to either of the formulae (III-d) and (III-e):

17. A polyurea made using at least one sulfur-comprising polyaromatic polyamine compound according to claim 1 .

18. A process for the synthesis of a polyurea comprising the step of:
polycondensating at least one sulfur-comprising polyaromatic polyamine compound according to claim 1 with a polyisocyanate compound.

19. A process for the synthesis of a polyurea comprising the step of:
using a sulfur-comprising polyaromatic polyamine compound according to claim 1 .

Assignees

• Michelin & Cie
• Michelin Rech Tech

Inventors

• Fedurco Milan
• Ribezzo Marco

Classifications

• C08G18/80

  Masked polyisocyanates · CPC title

• C08G18/3243 Primary

  containing two or more aromatic rings · CPC title

• C08G18/3868

  the sulfur atom belonging to a sulfide group · CPC title

• C08G18/643

  Reaction products of epoxy resins with at least equivalent amounts of amines · CPC title

• C08G18/7664

  containing alkylene polyphenyl groups · CPC title