IP Library Granted Patent US 10,435,485
Granted Patent B2
US 10,435,485 · App. 15/327,123 · Granted Oct 8, 2019

Polymer modified along the chain and process for the synthesis thereof

Inventors: Etienne Fleury (Clermont-Ferrand, FR); Julien Thuilliez (Clermont-Ferrand, FR); Jean-Michel Favrot (Clermont-Ferrand, FR)
Assignees: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN; MICHELIN RECHERCHE ET TECHNIQUE, S.A.
C08C19/22B60C1/00C08F8/30C08K3/04C08K3/36
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Quick Facts
Patent No.
US 10,435,485
App. No.
15/327,123
Granted
Oct 8, 2019
Kind
B2
Abstract

A polymer comprises randomly distributed units UA, UB, UC and UD and at least one unit bearing a subunit F according to the respective molar percentages m, n, o, p and f F pendant along the chain of the polymer and bearing an associative group comprising at least one nitrogen atom, R 1 and R 2 , which are identical or different, denoting a hydrogen atom, a methyl radical or a phenyl radical which is unsubstituted or substituted in the ortho, meta or para position by a methyl radical, m≥50, n≥0, o≥0, f>0, 0<0+p≤25, m, n, o, p and f ranging from 0 to 100, the respective molar percentages of m, n, o, p and f calculated based on the sum of m+n+o+p+f, which is equal to 100.

Claims (59)

1. A polymer which comprises the following units UA, UB, UC and UD and at least one unit bearing a subunit F,

which units UA, UB, UC and UD are distributed randomly within the polymer

the subunit F being pendant along the chain of the polymer and bearing an associative group comprising at least one nitrogen atom,

the unit bearing the subunit F being present in the polymer chain according to a molar percentage of f %,

R 1 and R 2 , which are identical or different, denoting a hydrogen atom, a methyl radical or a phenyl radical which is unsubstituted or substituted in the ortho, meta or para position by a methyl radical,

m≥50

n≥0

o≥0

f>0

0<o+p≤25

m, n, o, p and f being numbers ranging from 0 to 100

the respective molar percentages of m, n, o, p and f being calculated on the basis of the sum of m+n+o+p+f, which is equal to 100, and which contains the following units UE distributed randomly within the polymer,

o+p+q≤10

q≥0

the respective molar percentages of m, n, o, p, q and f being calculated on the basis of the sum of m+n+o+p+q+f, which is equal to 100.

2. A polymer according to claim 1 , which contains the following units UF distributed randomly within the polymer,

R 3 denoting an alkyl radical having from 1 to 4 carbon atoms or an aryl radical,

0≤r≤25,

the respective molar percentages of m, n, o, p, q, r and f being calculated on the basis of the sum of m+n+o+p+q+r+f, which is equal to 100.

3. A polymer according to claim 1 , in which the percentages o is different from 0.

4. A polymer which comprises the following units UA, UB, UC and UD and at least one unit bearing a subunit F,

which units UA, UB, UC and UD are distributed randomly within the polymer

the subunit F being pendant along the chain of the polymer and bearing an associative group comprising at least one nitrogen atom,

the unit bearing the subunit F being present in the polymer chain according to a molar percentage of f %,

R 1 and R 2 , which are identical or different, denoting a hydrogen atom, a methyl radical or a phenyl radical which is unsubstituted or substituted in the ortho, meta or para position by a methyl radical,

m≥50

n≥0

o≥0

f>0

0<o+p≤25

m, n, o, p and f being numbers ranging from 0 to 100

the respective molar percentages of m, n, o, p and f being calculated on the basis of the sum of m+n+o+p+f, which is equal to 100, in which n and o are different from 0.

5. A polymer according to claim 1 , in which at least one of the two molar percentages p and q is not equal to 0.

6. A polymer which comprises the following units UA, UB, UC and UD and at least one unit bearing a subunit F,

which units UA, UB, UC and UD are distributed randomly within the polymer

the subunit F being pendant along the chain of the polymer and bearing an associative group comprising at least one nitrogen atom,

the unit bearing the subunit F being present in the polymer chain according to a molar percentage of f %,

R 1 and R 2 , which are identical or different, denoting a hydrogen atom, a methyl radical or a phenyl radical which is unsubstituted or substituted in the ortho, meta or para position by a methyl radical,

m≥50

n≥0

o≥0

f>0

0<o+p≤25

m, n, o, p and f being numbers ranging from 0 to 100

the respective molar percentages of m, n, o, p and f being calculated on the basis of the sum of m+n+o+p+f, which is equal to 100, which contains, as monomer units, only the units UA, UB, UC, UD and UE and the units bearing the subunit F according to their respective molar percentages m, n, o, p, q and f.

7. A polymer according to claim 1 , in which R 1 and R 2 are identical and denote a hydrogen atom.

8. A polymer according to claim 1 , in which f varies from 0.01 to 50%.

9. A polymer according to claim 1 , in which the associative group is selected from the group consisting of the imidazolidinyl, triazolyl, triazinyl, bis-ureyl and ureido-pyrimidyl groups.

10. A polymer according to claim 1 , in which the associative group corresponds to one of the following formulae (I) to (V):

where:

Ch denotes a carbon chain which can optionally contain heteroatoms,

* represents a direct or indirect connection to the chain of the polymer,

R denotes a hydrocarbon group which can optionally contain heteroatoms,

X denotes an oxygen or sulphur atom or an NH group.

11. A polymer according to claim 1 , in which the associative group corresponds to the formula (VI):

where * represents a direct or indirect connection to the chain of the polymer.

12. A polymer according to claim 1 , which is an elastomer.

13. A rubber composition which comprises a reinforcing filler and a polymer defined according to claim 12 .

14. A tire which comprises a rubber composition according to claim 13 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 8, 2020
From: MICHELIN RECHERCHE ET TECHNIQUE S.A.
To: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN
Reel/Frame 052863/0624 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 18, 2017
From: FLEURY, ETIENNE; THUILLIEZ, JULIEN; FAVROT, JEAN-MICHEL
To: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN; MICHELIN RECHERCHE ET TECHNIQUE, S.A.
Reel/Frame 042421/0747 →