1,3-dipolar compound bearing an imidazole functional group

Patent metadata

Field	Value
Publication number	US-10202471-B2
Application number	US-201415031337-A
Country	US
Kind code	B2
Filing date	Oct 24, 2014
Priority date	Oct 25, 2013
Publication date	Feb 12, 2019
Grant date	Feb 12, 2019

Abstract

In a 1,3-dipolar compound of formula Q-A-B, Q comprises a dipole containing at least and preferably one nitrogen atom, A, which is preferably divalent, is an atom or a group of atoms connecting Q to B, and B comprises an imidazole ring. An unsaturated polymer modified by grafting the 1,3-dipolar compound is also disclosed.

First claim

The invention claimed is:

1. A process for modifying, by a grafting reaction, an unsaturated polymer which exhibits at least one unsaturation, the process comprising reacting a 1,3-dipolar compound with the at least one unsaturation of the unsaturated polymer,
wherein the 1,3-dipolar compound is of formula (I):
Q-A-B  (I),

wherein Q comprises a dipole containing at least one nitrogen atom,
wherein A is an atom or a group of atoms connecting Q to B, and
wherein B comprises a ring of formula (II):

wherein three of four symbols Z, Y, R, and R′ are identical or different, each representing an atom or a group of atoms, it being possible for Z and Y to form, together with carbon atoms to which they are attached, a ring, and a fourth of the four symbols Z, Y, R, and R′ denotes a direct attachment to A.

2. The process according to claim 1 , wherein R′ denotes a direct attachment to A.

3. The process according to claim 2 , wherein Z and Y are each a hydrogen atom.

4. The process according to claim 2 , wherein Z and Y form the ring together with the carbon atoms to which they are attached.

5. The process according to claim 1 , wherein R represents a hydrogen atom or a carbon-based group which can contain at least one heteroatom.

6. The process according to claim 5 , wherein R is an alkyl group containing from 1 to 12 carbon atoms.

7. The process according to claim 1 , wherein A is an aliphatic group or an aromatic group containing up to 20 carbon atoms which can contain at least one heteroatom.

8. The process according to claim 7 , wherein A is an alkylene group containing from 1 to 20 carbon atoms or an arylene group.

9. The process according to claim 1 , wherein the compound is selected from the group consisting of nitrile oxides, nitrile imines, and nitrones.

10. The process according to claim 9 , wherein Q contains a —C≡N→O unit.

11. The process according to claim 10 , wherein Q comprises a unit of formula (III):

wherein four of five symbols R 1 to R 5 are identical or different, each being an atom or a group of atoms, and a fifth of the five symbols R 1 to R 5 denotes a direct attachment to A, and
wherein neither of R 1 and R 5 is H.

12. The process according to claim 11 , wherein R 1 , R 3 , and R 5 are each an alkyl group of 1 to 6 carbon atoms.

13. The process according to claim 12 , wherein the compound is 2,4,6-trimethyl-3-((2-methyl-1H-imidazol-1-yl)methyl)benzonitrile oxide or 2,4,6-triethyl-3-((2-methyl-1H-imidazol-1-yl)methyl)benzonitrile oxide.

14. The process according to claim 9 , wherein Q contains a —C═N(→O) unit.

15. The process according to claim 14 , wherein Q comprises a unit of formula (IV) or (V):

wherein Y 1 is an aromatic group containing from 6 to 20 carbon atoms or an aliphatic group, and
wherein Y 2 , comprising a direct attachment to A, is an aliphatic group or an aromatic group comprising, on its aromatic nucleus, the direct attachment to A.

16. The process according to claim 14 , wherein the compound is of formula (IVa), (IVb), (Va), or (Vb):

17. The process according to claim 1 , wherein the 1,3-dipolar compound is reacted according to a stoichiometry of between 0 and 3 molar equivalents of imidazole ring per 100 moles of monomer units constituting the polymer.

18. The process according to claim 1 , wherein the unsaturated polymer is a diene polymer.

19. The process according to claim 18 , wherein the diene polymer is an essentially unsaturated diene elastomer selected from the group consisting of a polybutadiene, a polyisoprene, a butadiene copolymer, an isoprene copolymer, and a mixture thereof.

20. A polymer obtained by the process according to claim 1 .

Assignees

• Michelin & Cie
• Michelin Rech Tech
• Michelin & Cie

Inventors

• Ugolnikov Oleg
• Ivanov Sergey
• Rannoux Claire
• Salit Anne-Frédérique
• Gander Sophie
• Thuilliez Anne-Lise

Classifications

• C08F8/30 Primary

  Introducing nitrogen atoms or nitrogen-containing groups · CPC title

• C08C19/22

  Incorporating nitrogen atoms into the molecule · CPC title

• C07D233/61 Primary

  with hydrocarbon radicals, substituted by nitrogen atoms not forming part of a nitro radical, attached to ring nitrogen atoms · CPC title