1,3-dipolar compound bearing an imidazole functional group

Patent metadata

Field	Value
Publication number	US-2016251456-A1
Application number	US-201415031337-A
Country	US
Kind code	A1
Filing date	Oct 24, 2014
Priority date	Oct 25, 2013
Publication date	Sep 1, 2016
Grant date	—

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

1 - 28 . (canceled)

29 . 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.

30 . The process according to claim 29 , wherein R′ denotes a direct attachment to A.

31 . The process according to claim 30 , wherein Z and Y are each a hydrogen atom.

32 . The process according to claim 30 , wherein Z and Y form the ring together with the carbon atoms to which they are attached.

33 . The process according to claim 29 , wherein R represents a hydrogen atom or a carbon-based group which can contain at least one heteroatom.

34 . The process according to claim 33 , wherein R is an alkyl group containing from 1 to 12 carbon atoms.

35 . The process according to claim 29 , wherein A is an aliphatic group or an aromatic group containing up to 20 carbon atoms which can contain at least one heteroatom.

36 . The process according to claim 35 , wherein A is an alkylene group containing from 1 to 20 carbon atoms or an arylene group.

37 . The process according to claim 29 , wherein the compound is selected from the group consisting of nitrile oxides, nitrile imines, and nitrones.

38 . The process according to claim 37 , wherein Q contains a —C≡N→O unit.

39 . The process according to claim 38 , 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.

40 . The process according to claim 39 , wherein R 1 , R 3 , and R 5 are each an alkyl group of 1 to 6 carbon atoms.

41 . The process according to claim 40 , 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.

42 . The process according to claim 37 , wherein Q contains a —C═N(→O) unit.

43 . The process according to claim 42 , wherein Q comprises a unit of formula (IV) or (V):

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

44 . The process according to claim 42 , wherein the compound is of formula (IVa), (IVb), (Va), or (Vb):

45 . The process according to claim 29 , 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.

46 . The process according to claim 29 , wherein the unsaturated polymer is a diene polymer.

47 . The process according to claim 46 , 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.

48 . A polymer obtained by the process according to claim 29 .

49 . A 1,3-dipolar compound of formula (I):
Q-A-B  (I),
wherein Q comprises a —C≡N→O unit, 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.

50 . A 1,3-dipolar compound of formula (I):
Q-A-B  (I),
wherein Q comprises a unit of formula (IV) or (V):

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

51 . The compound according to claim 50 , wherein A is an arylene group containing from 6 to 20 carbon atoms.

52 . The compound according to claim 50 , wherein the compound is of formula (IVa), (IVb), (Va), or (Vb):

Assignees

• Michelin & Cie
• Michelin Rech Tech

Inventors

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

Classifications

• C07D233/61 Primary

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

• C08F8/30 Primary

  Introducing nitrogen atoms or nitrogen-containing groups · CPC title

• C08C19/22

  Incorporating nitrogen atoms into the molecule · CPC title