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Compounds Carrying Nitrogen Containing Binding Groups

Abstract: The invention relates to a compound of formula (I) wherein: A1 and A2 represent independently of one another a binding group comprising at least one nitrogen atom; Q1 and Q2 represent independently of one another a linkage group; and x is an integer between 2 and 6 preferably between 3 and 6. The invention also relates to a rubber composition comprising said compound.

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Patent Information

Application #
Filing Date
08 April 2019
Publication Number
27/2019
Publication Type
INA
Invention Field
CHEMICAL
Status
Email
mahua.ray@remfry.com
Parent Application

Applicants

ARKEMA FRANCE
420 rue d'Estienne d'Orves 92700 Colombes

Inventors

1. COUTURIER, Jean-Luc
26, rue Lieutenant-Colonel Prévost 69006 Lyon
2. DEVAUX, Jean-François
39, rue du stade 69510 Soucieu en Jarrest
3. HIDALGO, Manuel
8 Chemin de la Lande 69530 BRIGNAIS

Specification

The present invention relates to novel compounds useful as modifying agents in rubber compositions, methods for preparing thereof, as well as new rubber compositions comprising these compounds.

TECHNICAL BACKGROUND

In the industrial field of objects made from rubber compositions, polymer blends with fillers are often used. For such mixtures have good properties, continuously is searching for ways to improve filler dispersion within the polymers. One way to achieve this is the use of coupling agents capable of establishing interaction between polymer and filler.

For example, documents FR 2149339 and FR 2206330 disclose sulfur compounds comprising two terminals organosilicon groups used as coupling agent.

WO 2012/007684 discloses coupling agents comprising an associative group nitrogen and a nitrogen dipole.

WO 2012/007685 discloses molecules comprising an associative group and a nitrogenous azodicarbonyl group for modifying a polymer.

These compounds have disadvantages: they are obtained by a multi-step synthesis, typically in five stages, and their production is very expensive. Further, some raw materials needed for their preparation, as mesitol or dichloromethyl methyl ether, are not readily available commercially on a large scale.

Sulfur compounds have also been described in the prior art.

WO 03/002653 describes elastomeric compositions comprising a diene elastomer, an inorganic filler and an agent to

coupling, the latter being a polysilyl organosilicon compound comprising a sulfur group having a polythiosulphenamide function.

WO 2004/068238 discloses silver halide emulsions in which silver halide particles have been sensitized in the presence of a polysulfide compound.

The document "Chemical modeling of the synthase reaction thymidylate: evidence for the formation of an exocyclic methylene intermediate from analogues of the covalent ternary complex FORMED by thiol intramolecular addition to C (6) of 5-aminomethyluracil derivatives," Paul FC van der Melj and al., Tetrahedron Letters, 1988, vol. 29, No. 42, pp 5445-5448, discloses the synthesis of sulfur-containing compounds used as models of the ternary complex in the reaction of thymidylate synthase.

Document US 2005/014839 discloses disulfide compounds histone deacetylase inhibitors.

US 2014/155440 describes bioisosteres cysteine ​​and cystine for the treatment of schizophrenia and addiction.

The document "Accurate discrimination entre Phenyl Butyl and Groups in Molecular Aggregates", Tadashi Endo et al., Chemistry Letters, 1994, pp 231 1 -2314, discloses disulfide compounds including two acylurea groups and two terminals butyl, pentyl or phenyl.

WO 01/90060 describes the document disulfide compounds for treating allergies or systemic mastocytosis.

The document "NH Stretching Vibrations and conformation of bis [2- (3-Substituted ureido) phenyl] disulphide" A. TS. Antonova, Journal of Molecular Structure, 1989, Vol. 197, pp 97-104, discloses disulfide compounds of bis [2- (3-ureido substituted) phenyl].

The document "chelate oxorhenium to assemble new integrin antagonists," Julien Le Gay et al., Journal of Inorganic Biochemistry, 201 1, Vol. 105, pp 880-886, describes the synthesis of complex oxorhenium integrin antagonists in particular from disulfide compounds.

The document "immunomodulatory actions of levamisole - I. Structural analysis and immunomodulating activity of levamisole degradation products" Kimberly A. Hanson et al., Int. J. Immunopharmac, 1991, vol. 13, No. 6, pp 655-668, discloses the degradation products levamisole able to inhibit the lymphocyte response, these products being 3- (2-mercaptoethyl) -5-phenyl-imidazolidin-2-one, 6 -phenyl-2,3-dihydroimidazo (2,1-b) thiazole and disulfide, bis [3- (2-oxo-5-phenylimidazolidin-1-yl) ethyl].

There is a need to provide compounds obtained in few steps with good yields from raw materials cheap and readily available, these compounds ensuring good interaction between polymer and fillers, that is -dire for obtaining rubber compositions with good mechanical properties and good wear resistance.

SUMMARY OF THE INVENTION

The invention firstly relates to a compound of formula (I)

Ai - Qi - Sx - O 2 - A 2 (I)

in which

- and A 2 independently of one another an associative group comprising at least one nitrogen atom,

- Q1 and Q2 represent, independently from each other a linking group,

- x is an integer from 2 to 6, preferably from 3 to 6.

According to one embodiment, Ai and A2 are identical.

According to one embodiment, Ai and A2 are independently selected from imidazolidinone groups, triazoyl, ureyl, bis-ureyl, and ureido-pyrimidyl.

According to one embodiment, Ai and A2 independently correspond to one of formulas (II) to (VI):

(V)

or

- R denotes a hydrocarbon group optionally containing heteroatoms,

- Y denotes an oxygen or sulfur atom, preferably an oxygen atom.

According to one embodiment, at least one of Ai and A2, preferably both, is a group of formula (VII):

According to one embodiment, Qi and Q2 are independently a divalent linear or branched hydrocarbon radical, substituted or unsubstituted C1 -C24, preferably C1 -C10, optionally interrupted and / or substituted by one or more nitrogen atoms or oxygen, and more preferably a divalent hydrocarbon radical in C1-C6, uninterrupted and unsubstituted; Q1 and Q2 are preferably the same.

According to one embodiment, x equals 4.

According to one embodiment, the compound of the invention is selected from compounds of formulas (VIII) to (XI) below:

(VIII)

x being an integer from 2 to 4, preferably from 3 to 4 in the formula (VIII) and (IX).

The invention also relates to a mixture of different compounds of formula (I)

in which

Ai and i independently of one another an associative group comprising at least one nitrogen atom,

Qi and Q.2 each independently of the other a linking group,

x is an integer from 2 to 6;

compounds having different values ​​of x and being otherwise identical, wherein x has an average value between 2 and 6.

The invention also relates to a method for preparing a as defined above compound, comprising a step of reacting a sulfur compound with a compound of formula (XII)

and a compound of formula (XIII)

in which

- Ai, A2, Q1 and Q2 are as defined above, and

- Z represents a Cl atom or an SH group.

According to one embodiment, the compound of formula (XII) and the compound of formula (XIII) are identical.

According to one embodiment, the sulfur compound is sodium tetrasulfide, Z is a Cl atom and the compound prepared is of formula (I) with x = 4; and:

- preferably at least one of Ai and A2, more preferably both, is a group of formula (VII):

- preferably Q1 and Q2 are independently a divalent linear or branched hydrocarbon radical C1 -C10, more preferably a divalent linear hydrocarbon radical-C2; and or

- preferably the compound of formula A - Q1 - Cl and the compound of formula A2 - Q2 - Cl are identical.

According to one embodiment, the sulfur compound is sulfur monochloride, Z is an SH group and the compound prepared is of formula (I) with x = 4; and:

- preferably at least one of Ai and A2, more preferably both, is a group of formula (VII):

- preferably Q1 and Q2 are independently a divalent linear or branched hydrocarbon radical C1 -C10, more preferably a C2 divalent hydrocarbon radical; and or

- preferably the compound of formula A - Q1 - SH is obtained by reacting a compound of formula A - Q1 - Cl with sodium hydrosulfide NaSH; and or

- preferably the compound of formula A2 - Q2 - SH is obtained by reacting a compound of formula A2 - Q2 - Cl with sodium hydrosulfide NaSH; and or

- preferably the compound of formula A - Q1 - SH and the compound of formula A2 - Q2 - SH are identical.

According to one embodiment, the sulfur compound is sulfur, Z is an SH group and the compound prepared is of formula (I) with x ranging from 2 to 4; and - preferably at least one of Ai and A2, more preferably both, is a group of formula (VII):

- preferably Q1 and Q2 are independently a divalent linear or branched hydrocarbon radical C1 -C10, more preferably a divalent linear hydrocarbon radical-C2; and or

- preferably the reaction is catalytic; and or

- preferably the compound of formula A - Q1 - SH is obtained by reacting a compound of formula A - Q1 - Cl with sodium hydrosulfide NaSH; and or

- preferably the compound of formula A2 - Q2 - SH is obtained by reacting a compound of formula A2 - Q2 - Cl with sodium hydrosulfide NaSH; and or

- preferably the compound of formula A - Q1 - SH and the compound of formula A2 - Q2 - SH are identical.

The invention also relates to a rubber composition comprising at least one diene elastomer, a reinforcing filler, a chemical crosslinking agent and a modifying agent, optionally already grafted onto the elastomer, said modifier being a compound as hereinbefore defined -Dessus or a mixture as defined above.

According to one embodiment, the diene elastomer comprises an essentially unsaturated diene elastomer selected from natural rubber, synthetic polyisoprenes, polybutadienes, butadiene copolymers, isoprene copolymers and mixtures thereof; and / or comprises a substantially saturated rubber selected from butyl rubber, copolymers of dienes and of alpha-olefins such as EPDM and mixtures thereof.

According to one embodiment, the chemical crosslinking agent comprises from 0.5 to 12 phr of sulfur, preferably from 1 to 10 phr of sulfur, or from 0.01 to 10 phr of one or more peroxide compounds.

According to one embodiment, the modifying agent content ranges from 0.01 to 50 mol%, preferably from 0.01 mol% to 5 mol%.

The invention also relates to a process for preparing a rubber composition as defined above, comprising one or more mixing stages of thermomechanical the diene elastomer, the reinforcing filler, the chemical crosslinking agent and the agent modification and a step of extruding and calendering.

The invention also relates to an object manufactured in whole or in part with a rubber composition as defined above, preferably selected from gaskets, thermal or acoustic insulation, cables, sheaths, soles footwear, packaging, coatings (paints, films, cosmetics), patches (cosmetic or dermopharmaceutical), other systems for trapping and release active, wound dressings, flexible hose clips, vacuum tubes and tubes and hoses for conveying fluids.

The invention also relates to a modified polymer obtained by grafting a compound as defined above or a mixture as defined above.

According to one embodiment, the polymer is a diene elastomer.

According to one embodiment, the polymer is a diene elastomer selected from essentially unsaturated natural rubber, synthetic polyisoprenes, polybutadienes, butadiene copolymers, isoprene copolymers and mixtures of these elastomers; or a substantially saturated elastomer selected from butyl rubbers and copolymers of dienes and of alpha-olefins such as EPDM.

The invention also relates to a method for preparing a modified polymer comprising a step of grafting a compound as defined above or a mixture as defined above on a polymer having at least one unsaturation.

The present invention overcomes the disadvantages of the prior art. It provides more particularly compounds of formula (I) for obtaining rubber compositions having both improved properties and having a reduced manufacturing cost.

The compounds of formula (I) can be prepared in few steps, e.g., two to four stages, some of which may be performed in the same reactor, and from inexpensive raw materials.

Advantageously, the invention provides rubber compositions having high performance mechanical properties and a good wear resistance.

EMBODIMENTS DESCRIPTION OF THE INVENTION

The invention is now described in more detail and not limited to the following description.

Compounds of formula (I)

The invention relates to a compound of formula (I):

wherein S is a sulfur atom, x is an integer, and A 2 independently of one another an associative group comprising at least one nitrogen atom, and Q1 and Q2 are linking groups.

By "community groups" means groups capable of associating with one another by hydrogen bonds, ionic and / or hydrophobic. This is, according to a preferred embodiment of the invention, groups capable of associating via hydrogen bonds.

When the associative groups are likely to be associated by hydrogen bonds, each associative group preferably comprises at least one "site" donor and a site vis-à-vis acceptor hydrogen bonding so that two identical associative groups are self -complémentaires and may associate with each other by forming at least two hydrogen bonds.

The associative groups of the invention are also likely to be associated by hydrogen bonds, ionic and / or hydrophobic to functional groups present on fillers.

The groups Ai and A2 can be different or identical, preferably Al and A2 are identical.

According to a particular embodiment of the invention, the associative groups Ai and A2 are independently selected from the imidazolidinone groups, ureyl, bis-ureyl, and ureido-pyrimidyl triazolyl.

Preferably, the associative groups Ai and A2 independently correspond to one of formulas (II) to (VI):

(Ml)

or

- R denotes a hydrocarbon group (preferably C1 -C10, more preferably still C 1 -C 6) linear, branched or cyclic (preferably linear), which may optionally contain heteroatoms (and preferably not containing ), - Y denotes an oxygen or sulfur atom, preferably an oxygen atom.

In formula (II), the two nitrogen atoms are linked by a divalent organic group such as a hydrocarbylene group such as an alkylene, substituted alkylene, cycloalkylene, substituted cycloalkylene, arylene or substituted arylene. The hydrocarbylene group contains from 1 to 10 carbon atoms. The hydrocarbylene group may also contain heteroatoms such as nitrogen, oxygen or sulfur. These heteroatoms may be included in the chain hydrocarbylene or substituted carbon. Particularly preferably, the group of formula (II) contains 5 or 6 atoms.

Preferably, the groups Ai and A2 are independently a heterocycle or di triazoté, 5 or 6 atoms, preferably diazotized, and comprising at least one carbonyl function.

Even more preferably, the Al and A2 groups are imidazolidinone group of formula (VII):

(VII)

According to one embodiment more particularly, Ai and A2 are both a group of formula (VII):

Q1 and Q2 linking groups can be any divalent radical. They are preferably chosen so as not to little or interfere with voluntary groups and A 2.

Said groups Q1 and Q2 are then considered as inert groups vis-à-vis community groups and A 2. By "inert group vis-à-vis the associative groups Ai and AΣ" means a group which does not include associative functions as defined according to the invention.

Q1 and Q2 groups are preferably independently a divalent hydrocarbon radical, linear, branched or cyclic. They may independently contain one or more aromatic radicals, and / or one or more heteroatoms. The divalent hydrocarbon radical may optionally be substituted, the substituents preferably being inert with respect associative groups Ai and A2.

According to a preferred embodiment, the groups Q1 and Q2 are independently a divalent linear or branched hydrocarbon radical, substituted or unsubstituted C1 -C24, preferably C1 -C10, optionally interrupted and / or substituted by one or more atoms nitrogen or oxygen, more preferably a divalent hydrocarbon radical in C1-C6, uninterrupted and unsubstituted, and more preferably linear.

Q1 and Q2 may be the same or different, but preferably Q1 and Q2 are identical.

In formula (I) above, x is an integer ranging from 2 to 6.

According to particular embodiments, x is an integer ranging from 2 to 5, where x is an integer ranging from 2 to 4, or x is an integer from 3 to 5, or x is an integer equal to 2 or 3, where x is an integer equal to 3 or 4.

According to other particular embodiments, x is 2 or 3, or 4, or

5 or 6.

According to a particular embodiment, the compound of the invention is selected from compounds of formula (VIII) or (IX) below:

x being an integer from 2 to 6 in the formula (VIII) and (IX), preferably x is an integer ranging from 2 to 5, even more preferably x is an integer ranging from 2 to 4 and even more preferably x is an integer equal to 3 or 4.

According to one embodiment even more particular, the compound of the invention is

The invention also relates to mixtures of different compounds of formula (I) (and for example of formula (VIII)) with different values ​​of x (the compounds being otherwise identical). For example, the invention relates to mixtures of compounds of formula (I) with x ranging from 2 to 6, or 2 to 5, or 2 to 4, the compounds being otherwise identical. The invention also more particularly relates to mixtures of compounds of formula (VIII) with x ranging from 2 to 6, or 2 to 5, or 2 to 4, the compounds being otherwise identical. Such a mixture can be regarded as a compound of formula (I) (respectively of formula (VIII)) with x having a certain statistical distribution and in particular an average value that is not necessarily an integer, which is between 2 and 6 (preferably between 2 and 5,

In particular, certain preparation methods described below result in the formation of such mixtures of compounds.

Processes for preparing compounds of formula (I)

The compounds of the invention may be prepared by a process generally comprising a step of reacting a sulfur compound with a compound of formula (XII)

Ai - Qi - Z (XII)

and a compound of formula (XIII)

in which

Ai, A2, Q1 and Q2 are as defined above, and

Z represents a Cl atom or an SH group.

The compound of formula (XII) and the compound of formula (XIII) may be identical or different; preferably they are identical. In this case, the method provides for reacting a certain amount of sulfur-containing compound with an amount of one compound of formula (XII).

According to one embodiment of the invention, mixtures of compounds of formula (I) according to the invention with means x varying from 2 to 6, preferably from 2 to 5 and more preferably from 2 to 4, are prepared by a process comprising a step of reacting a medium grade sodium polysulfide Na 2 S x of x with a compound of formula a - Q1 - Cl and a compound of formula A2 - Q2 - Cl, in which Ai, A2, Q1 and Q2 have the meanings defined above.

The compound of formula A - Q1 - Cl and the compound of formula A2 - Q2 - Cl may be different or identical. Preferably they are identical. In this case, the method provides for the reaction of a quantity of sodium polysulphide with an amount of one compound of formula A - Q1 - Cl.

The rank of sodium polysulfide average x may be prepared by reaction in a solvent between sodium sulfide and sulfur in adapting their respective molar proportions according to the following equation:

Na2S + (x-1 ) S Na2Sx

Sodium polysulfide Na 2 S x preparation reaction medium in row x and its reaction with a compound of formula A - Q1 - Cl and a compound of formula A2 - Q2 - Cl are preferably conducted in one or more solvents. A wide choice of solvents is possible from solvents known to those skilled in the art to promote nucleophilic substitutions. For example one can use the following solvents, alone or in combination: an alcohol such as methanol, ethanol, 1-propanol, 2-propanol, butanol, an aromatic such as toluene, xylene, an ether such as isopropyl ether, methyl t-butyl ether, dioxane and tetrahydrofuran.

Reacting sodium polysulphide with a compound of formula A - Q - Cl, and a compound of formula A2 - Q2 - Cl may be carried out by adding compounds of formulas Ai - Q1 - Cl and A2 - Q2 - Cl to a solution of sodium polysulfide or by adding a sodium polysulfide solution to a solution of compounds of formulas Ai - Q1 -Cl and A2 - Q2 - Cl. Alternatively the sodium sulfide solution and the solution of the compounds of formulas Ai - Q1 - Cl and A2 - Q2 - Cl may be added simultaneously in a semi-continuous or continuous reactor. The temperature of the reaction step may be between room temperature, e.g. 20 ° C and 150 ° C and preferably between room temperature, e.g. 20 ° C and 100 ° C. Preferably

The molar ratio of Na 2 S x rank sodium polysulfide average x and the compounds of formula A - Q1 - Cl and A2 - Q2 - Cl is 0.95 to 1, 5, preferably 1 to 1, and more preferably 2 of 1 to 1, 1.

According to a particular embodiment, the reactions are done in a dry environment with anhydrous sodium sulfide and anhydrous solvents.

The salt formed during the reaction (NaCl) can be removed by filtration and the final product may be isolated by evaporating the solvent. According to a particular embodiment, a water washing step can be implemented to remove inorganic residues of the product.

CLAIMS

Compound of formula (I)

in which

- and A i independently of one another an associative group comprising at least one nitrogen atom,

- Qi and Q2 are independently of each other a linking group,

- x is an integer from 3 to 6.

A compound according to claim 1, wherein Ai and A2 are identical.

A compound according to claim 1 or 2, wherein Ai and A2 are independently selected from imidazolidinone groups, triazoyl, ureyl, bis-ureyl, and ureido-pyrimidyl.

A compound according to one of claims 1 to 3, wherein Ai and A2 independently correspond to one of formulas (II) to (VI):

(IV)

(V)

or :

- R denotes a hydrocarbon group optionally containing heteroatoms,

- Y denotes an oxygen or sulfur atom, preferably an oxygen atom.

A compound according to one of claims 1 to 4, wherein at least one of Ai and A2, and preferably both, is a group of formula (VII):

A compound according to one of claims 1 to 5 wherein Q1 and Q2 are independently a divalent linear or branched hydrocarbon radical, substituted or unsubstituted C1 -C24, preferably C1 -C10, optionally interrupted and / or substituted by a or more nitrogen atoms or oxygen atoms, and more preferably a divalent hydrocarbon radical in C1-C6, uninterrupted and unsubstituted; Q1 and Q2 are preferably the same.

A compound according to one of claims 1 to 6, wherein x is 4.

A compound according to one of claims 1 to 7, selected from compounds of formulas (VIII) to (XI) below:

x being an integer ranging from 3 to 4 in the formula (VIII) and (IX).

9. Mixture of different compounds of formula (I)

in which

- and A 2 independently of one another an associative group comprising at least one nitrogen atom,

- Q1 and Q2 represent, independently from each other a linking group,

- x is an integer from 2 to 6;

compounds having different values ​​of x and being otherwise identical,

wherein x has an average value between 2 and 6.

10. A process for preparing a compound according to one of claims 1 to 8, comprising a step of reacting a sulfur compound with a compound of formula (XII)

and a compound of formula (XIII)

A2 - Q2 - Z (XIII),

in which

- Ai, A2, Q1 and Q2 are as defined in one of claims 1 to 8, and

- Z represents a Cl atom or an SH group.

The method of claim 10, wherein the compound of formula (XII) and the compound of formula (XIII) are identical.

A method according to claim 10 or 1 1, wherein the sulfur compound is sodium tetrasulfide, Z is a Cl atom and the compound prepared is of formula (I) with x = 4; and:

- preferably at least one of Ai and A2, more preferably both, is a group of formula

(VII) :

- preferably Q1 and Q2 are independently a divalent linear or branched hydrocarbon radical C1 -C10, more preferably a divalent linear hydrocarbon radical-C2; and or

- preferably the compound of formula A - Q1 - Cl and the compound of formula A2 - Q2 - Cl are identical.

A method according to claim 10 or 1 1, wherein the sulfur compound is sulfur monochloride, Z is an SH group and the compound prepared is of formula (I) with x = 4; and:

- preferably at least one of Ai and A2, more preferably both, is a group of formula

(VII) :

(VII); and or

preferably Qi and Q2 are independently a divalent linear or branched hydrocarbon radical C1 -C10, more preferably a C2 divalent hydrocarbon radical; and or

preferably the compound of formula A - Q1 - SH is obtained by reacting a compound of formula A - Q1 - Cl with sodium hydrosulfide NaSH; and or

preferably the compound of formula A2 - Q2 - SH is obtained by reacting a compound of formula A2 - Q2 - Cl with sodium hydrosulfide NaSH; and or

preferably the compound of formula A - Q1 - SH and the compound of formula A2 - Q2 - SH are identical.

A method according to claim 10 or 1 1, wherein the sulfur compound is sulfur, Z is an SH group and the compound prepared is of formula (I) with x ranging from 2 to 4; and:

- preferably at least one of Ai and A2, more preferably both, is a group of formula

(VII) :

(VII); and or

preferably Q1 and Q2 are independently a divalent linear or branched hydrocarbon radical C1 -C10, more preferably a divalent linear hydrocarbon radical-C2; and or

preferably the reaction is catalytic; and or

preferably the compound of formula A - Q1 - SH is obtained by reacting a compound of formula A - Q1 - Cl with sodium hydrosulfide NaSH; and or

preferably the compound of formula A2 - Q2 - SH is obtained by reacting a compound of formula A2 - Q2 - Cl with sodium hydrosulfide NaSH; and or

preferably the compound of formula A - Q1 - SH and the compound of formula A2 - Q2 - SH are identical.

A rubber composition comprising at least one diene elastomer, a reinforcing filler, a chemical crosslinking agent and a modifying agent, optionally already grafted onto the elastomer, said modifier being a compound according to one of claims 1 to 8 or a mixture according to claim 9.

The composition of claim 15 wherein the diene elastomer comprises an essentially unsaturated diene elastomer selected from natural rubber, synthetic polyisoprenes, polybutadienes, butadiene copolymers, isoprene copolymers and mixtures thereof; and / or comprises a substantially saturated rubber selected from butyl rubber, copolymers of dienes and of alpha-olefins such as EPDM and mixtures thereof.

Composition according to one of claims 15 to 16, wherein the chemical crosslinking agent comprises from 0.5 to 12 phr of sulfur, preferably from 1 to 10 phr of sulfur, or from 0.01 to 10 phr of one or more peroxide compounds.

Composition according to one of claims 15 to 17, wherein the modifying agent content ranges from 0.01 to 50 mol%, preferably from 0.01 mol% to 5 mol%.

A process for preparing a rubber composition according to one of claims 15 to 18, comprising mixing one or more steps of thermomechanical the diene elastomer, the reinforcing filler, the chemical crosslinking agent and the modifying agent and a step of extruding and calendering.

Object manufactured entirely or partially with a rubber composition according to one of claims 15 to 18, preferably selected from gaskets, thermal or acoustic insulation, cables, sheaths, shoe soles, packaging, coatings (paints, films, cosmetics), patches (cosmetic or dermopharmaceutical), other scavenging systems

release of active wound dressings, elastic clamps, vacuum tubes and the tubes and hoses for conveying fluids.

Modified polymer obtained by grafting a compound according to one of claims 1 to 8 or a mixture according to claim 9.

Modified polymer according to claim 21, wherein the polymer is a diene elastomer.

Modified polymer according to claim 21 or 22, wherein the polymer is a diene elastomer selected from essentially unsaturated natural rubber, synthetic polyisoprenes, polybutadienes, butadiene copolymers, isoprene copolymers and mixtures of these elastomers; or a substantially saturated elastomer selected from butyl rubbers and copolymers of dienes and of alpha-olefins such as EPDM.

A process for preparing a modified polymer comprising a step of grafting a compound according to one of claims 1 to 8 or a mixture according to claim 9 of a polymer having at least one unsaturation.

Documents

Application Documents

# Name Date
1 201917014069.pdf 2019-04-08
2 201917014069-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [08-04-2019(online)].pdf 2019-04-08
3 201917014069-STATEMENT OF UNDERTAKING (FORM 3) [08-04-2019(online)].pdf 2019-04-08
4 201917014069-PROOF OF RIGHT [08-04-2019(online)].pdf 2019-04-08
5 201917014069-PRIORITY DOCUMENTS [08-04-2019(online)].pdf 2019-04-08
6 201917014069-POWER OF AUTHORITY [08-04-2019(online)].pdf 2019-04-08
7 201917014069-FORM 1 [08-04-2019(online)].pdf 2019-04-08
8 201917014069-DECLARATION OF INVENTORSHIP (FORM 5) [08-04-2019(online)].pdf 2019-04-08
9 201917014069-COMPLETE SPECIFICATION [08-04-2019(online)].pdf 2019-04-08
10 201917014069-OTHERS-100419.pdf 2019-04-15
11 201917014069-Correspondence-100419.pdf 2019-04-15
12 201917014069-FORM 3 [22-04-2019(online)].pdf 2019-04-22