Grafted polymer carrying pendent imidazole functional groups
View Patent ↗A modified polymer is obtained by grafting of at least one compound of formula (I) onto at least one unsaturation of the initial polymer chain in which Q represents a dipole comprising at least one nitrogen atom; A represents a divalent heteroaromatic ring optionally substituted with one or more identical or different linear or branched aliphatic hydrocarbon-based chains, optionally substituted or interrupted with one or more heteroatoms; E represents a divalent hydrocarbon-based group which may optionally contain one or more heteroatoms; R 1 represents a hydrogen atom or a C 1 -C 20 alkyl group; and Y and Z, which may be identical or different, each represent a hydrogen atom or a hydrocarbon-based chain, Y and Z together also possibly forming a ring, notably an aromatic ring, with the carbon atoms of the imidazole ring to which they are attached.
1. A modified polymer obtained by grafting of at least one compound of formula (I) onto at least one unsaturation of an initial polymer chain
in which:
Q represents a dipole comprising at least one nitrogen atom;
A represents a divalent heteroaromatic ring optionally substituted with one or more identical or different linear or branched aliphatic hydrocarbon-based chains, optionally substituted or interrupted with one or more heteroatoms;
E represents a divalent hydrocarbon-based group which may optionally contain one or more heteroatoms;
R 1 represents a hydrogen atom or a C 1 -C 20 alkyl group; and
Y and Z, which may be identical or different, each represent a hydrogen atom or a hydrocarbon-based chain, or Y and Z together form a ring with the carbon atoms of the imidazole ring to which they are attached.
2. The modified polymer according to claim 1 , wherein a molar degree of grafting of the compound of formula (I) is in a range extending from 0.01% to 15%.
3. The modified polymer according to claim 1 , wherein Q is a group of formula (II), (III) or (IV)
in which:
the symbol * represents the attachment of Q to A;
R 2 and R 4 are selected, independently of each other, from a hydrogen atom, a linear or branched C 1 -C 20 alkyl, a C 3 -C 20 cycloalkyl optionally substituted with one or more aliphatic hydrocarbon-based chains, which are optionally saturated, linear or branched, and a C 6 -C 20 aryl optionally substituted with one or more aliphatic hydrocarbon-based chains; and
R 3 is selected from the group consisting of linear or branched C 1 -C 20 alkyls, C 3 -C 20 cycloalkyls optionally substituted with one or more aliphatic hydrocarbon-based chains, and C 6 -C 20 aryls optionally substituted with one or more aliphatic hydrocarbon-based chains.
4. The modified polymer according to claim 3 , wherein the compound of formula (I) is chosen from the compounds of formula (IIa)
in which:
A represents a divalent heteroaromatic ring optionally substituted with one or more identical or different linear or branched aliphatic hydrocarbon-based chains, optionally substituted or interrupted with one or more heteroatoms;
E represents a divalent hydrocarbon-based group which may optionally contain one or more heteroatoms;
R 1 represents a hydrogen atom or a C 1 -C 20 alkyl group;
Y and Z, which may be identical or different, each represent a hydrogen atom or a hydrocarbon-based chain, or Y and Z together form a ring with the carbon atoms of the imidazole ring to which they are attached;
R 2 is selected from a hydrogen atom, a linear or branched C 1 -C 20 alkyl, a C 3 -C 20 cycloalkyl optionally substituted with one or more aliphatic hydrocarbon-based chains, and a C 6 -C 20 aryl optionally substituted with one or more aliphatic hydrocarbon-based chains; and
R 3 is selected from the group consisting of linear or branched C 1 -C 20 alkyls, C 3 -C 20 cycloalkyls optionally substituted with one or more aliphatic hydrocarbon-based chains, and C 6 -C 20 aryls optionally substituted with one or more aliphatic hydrocarbon-based chains.
5. The modified polymer according to claim 1 , wherein A is a divalent heteroaromatic ring formed from 5 to 10 atoms, optionally substituted with one or more identical or different linear or branched, aliphatic C 1 -C 24 hydrocarbon-based chains, optionally substituted or interrupted with one or more heteroatoms.
6. The modified polymer according to claim 4 , wherein the compound of formula (IIa) is selected from compounds of formula (IIb)
in which:
X represents a heteroatom selected from a sulfur atom, an oxygen atom and a nitrogen atom;
E represents a divalent hydrocarbon-based group which may optionally contain one or more heteroatoms;
R 1 represents a hydrogen atom or a C 1 -C 20 alkyl group;
Y and Z, which may be identical or different, each represent a hydrogen atom or a hydrocarbon-based chain, or Y and Z together form a ring with the carbon atoms of the imidazole ring to which they are attached;
R 2 is selected from a hydrogen atom, a linear or branched C 1 -C 20 alkyl, a C 3 -C 20 cycloalkyl optionally substituted with one or more aliphatic hydrocarbon-based chains, and a C 6 -C 20 aryl optionally substituted with one or more aliphatic hydrocarbon-based chains; and
R 3 is selected from the group consisting of linear or branched C 1 -C 20 alkyls, C 3 -C 20 cycloalkyls optionally substituted with one or more aliphatic hydrocarbon-based chains, and C 6 -C 20 aryls optionally substituted with one or more aliphatic hydrocarbon-based chains.
7. The modified polymer according to claim 3 , wherein R 2 is a hydrogen atom and R 3 is selected from C 1 -C 20 alkyls and C 6 -C 20 aryls.
8. The modified polymer according to claim 1 , wherein E is selected from linear or branched, saturated aliphatic C 1 -C 24 , optionally interrupted with one or more nitrogen, sulfur or oxygen atoms.
9. The modified polymer according to claim 1 , wherein E is selected from the groups —R—, —NHR—, —OR— and —SR—, where R is a linear or branched C 1 -C 24 alkylene.
10. The modified polymer according to claim 1 , wherein Y and Z, which may be identical or different, each represent a hydrogen atom or a linear or branched C 1 -C 24 alkyl, or Y and Z together form a ring with the carbon atoms of the imidazole ring to which they are attached.
11. The modified polymer according to claim 1 , wherein Y and Z are a hydrogen atom.
12. The modified polymer according to claim 1 , wherein R 1 is a hydrogen atom or a C 1 -C 6 alkyl.
13. The modified polymer according to claim 1 , wherein the compound of formula (I) is the compound of formula (VIII)
14. The modified polymer according to claim 1 , wherein the initial polymer is an elastomer.
15. A composition comprising at least one modified polymer according to claim 1 and at least one additive.