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Biomimetic Synthetic Rubber

Abstract: The invention relates to a composition containing (i) a cross-linkable synthetic poly(cis-1,4-diene) that has a cis content of at least 95% and a functional moiety on the end, and (ii) an amphiphilic compound.

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Patent Information

Application #
Filing Date
10 March 2021
Publication Number
17/2021
Publication Type
INA
Invention Field
POLYMER TECHNOLOGY
Status
Email
archana@anandandanand.com
Parent Application
Patent Number
Legal Status
Grant Date
2023-10-25
Renewal Date

Applicants

FRAUNHOFER-GESELLSCHAFT ZUR FÖRDERUNG DER ANGEWANDTEN FORSCHUNG E.V.
Hansastraße 27c 80686 München

Inventors

1. WENDLER, Ulrich
Hainbuchenweg 12 06118 Halle
2. MALKE, Marlen
Delitzscher Str. 74 06112 Halle
3. MÜLLER, Lowis-Gerrit-Boje
Quellenstr. 21 48431 Rheine
4. SCHULZE GRONOVER, Christian
Josef-Pieper Str. 42 48149 Münster
5. PRÜFER, Dirk
Sophienstrasse 22A 48145 Münster
6. WÖTZEL, Jacqueline
Mühlberg 11h 06719 Teutschenthal
7. BEINER, Mario
Am Wallholz 2 06258 Schkopau
8. GUPTA, Gaurav
Zollrain 5a 06124 Halle(Saale)

Specification

Biomimetic synthetic rubber

The present invention relates to a biomimetic synthetic rubber composition which has a high degree of expansion crystallization and is therefore very well suited for the production of rubber-elastic molded bodies which are exposed to high mechanical loads (in particular tires or their

Running surfaces) or as special medical products (e.g. tubes).

Elastomers obtained from natural or synthetic rubbers through crosslinking ("vulcanization"), which are also referred to as rubber, are used in a wide variety of areas due to their elastic properties, e.g. for tires, medical products (e.g. protective gloves and condoms) or other technical rubber goods.

Well-known synthetic rubbers are, for example, polymers that by

Polymerization of 1,3-diene compounds such as 1,3-butadiene or isoprene (2-methylbuta- 1,3-diene) can be obtained.

During the polymerization of 1,3-diene such as isoprene or 1,3-butadiene, the repeating units of the polymer can form different isomeric forms depending on the catalyst used (e.g. the cis-1,4- or tara-1,4-form ).

The technically relevant form of polyisoprene is, in particular, poly (cis-1,4-isoprene) (ie a polyisoprene with a high proportion of repeating units which are in the c1,4-form).

The anionic chain polymerization of isoprene, which is initiated, for example, by an organic lithium compound such as butyllithium, is known.

The anionic polymerization of isoprene usually leads to a proportion of the cis-1,4 form of less than 95%.

Coordinative chain polymerization is also known

(Coordination polymerization) of isoprene in the presence of a

Coordination catalyst. Via the coordination polymerization, a

Polyisoprene can be obtained with a cis content of at least 95% or even at least 97%.

Polybutadiene can likewise be produced by an anionic chain polymerization or a coordination polymerization, poly (cis-1,4-butadiene) with a high cis content being accessible, in particular, via the coordination polymerization.

A suitable coordination catalyst for the targeted production of a poly (cis-1,4-diene) with a very high cis content is, for example, a Ziegler-Natta catalyst which contains a transition metal or a rare earth metal and usually an organoaluminum compound.

Coordination catalysts for the selective production of poly (cis-1,4-dienes) are described, for example, by Z. Zhang et al., Structure and Bonding, Vol. 137, 2010, pp. 49-108 and in WO 2011/045393 A1.

For tire production, the elastomers are mixed with fillers such as SiO 2 and soot (“carbon black”). In this context, it is known to provide the polymer with functional, polar groups. This can take place, for example, after the polymerization when the catalytically active species is still present at the ends of the polymer chains. With the addition of suitable “modifier compounds”, terminal functional groups (eg acidic or basic groups) can be attached to the polymer. This is also referred to as end group functionalization and the polymers obtained are end group functionalized polymers.

In particular, the anionic polymerization is very suitable for

End group functionalization of polymers. But also for them

Coordination polymerization is known to introduce terminal functional groups into the polymer.

The attachment of terminal functional groups to poly (cis-1,4-dienes) which are produced via coordination polymerization in the presence of a coordination catalyst is described, for example, in EP 1 873 168 A1, EP 1 939 221 A2 and EP 2 022 803 A2. To produce a tire composition, these end-group-functionalized polymers are mixed with suitable fillers such as carbon black or Si0 2 or other inorganic additives.

Natural rubber (or the elastomer obtained after it has been crosslinked) has exceptional properties in some areas of application that are comparable to conventional synthetic rubbers such as synthetic polyisoprene or

Polybutadiene could not yet be achieved. This behavior of the

Natural rubber is due to a shear-induced crystallization or strain crystallization (ie a spontaneous, reversible stiffening of the material in the event of deformation under mechanical stress), which takes place in the synthetic elastomers with significantly lower intensity.

Natural rubber is obtained from the rubber tree Hevea brasiliensis and therefore has the disadvantage of limited availability.

Particularly in the medical field, natural rubber is also disadvantageous because of its allergenic potential (“latex allergy”). This allergenic potential is due to the

Presence of proteins in natural rubber.

J. Sakdapipanich et al., Rubber Chemistry and Technology, November 2008, Vol. 81, pp. 753-766, examined the expansion crystallization of natural rubber and of modified, protein- and / or lipid-free natural rubber, its proteins and / or lipids were removed by appropriate enzyme treatment. The enzymatic separation of proteins and lipids led to a reduction in the shear-induced crystallization ability of natural rubber. The separated lipid component is given back to the lipid- and protein-free one

Natural rubber, the composition thus obtained even shows a further decrease in the elongation crystallization.

Due to the disadvantages of natural rubber described above (limited

Availability, allergenic potential) are compositions of interest that are based on synthetic elastomers and yet show strain crystallization that comes as close as possible to that of natural rubber.

US 2014/0343231 A1 describes a polydiene such as polyisoprene or polybutadiene which is produced via an anionic polymerization and a reactive functional group, in particular a maleimide group, being attached in the terminal position. A further polymer, for example a polyacrylamide, is then grafted onto this terminal functional group.

H. Chu et al., Colloid and Polymer Science, February 2016, Vol. 294, pp. 433-439, describe the preparation of a chemically modified polyisoprene. As

The starting material used was a polyisoprene produced by anionic polymerization with a cis content of 73%. Methyl groups in non-terminal monomer units were converted into carboxyl-containing groups and phosphatidylcholine molecules were then covalently attached to these non-terminal carboxyl groups via a chemical reaction.

One object of the present invention is to provide a composition which is accessible via the simplest possible method on synthetic

Based on elastomers, it still shows a stretch crystallization that comes as close as possible to that of natural rubber.

The object is achieved by a crosslinkable composition containing - a crosslinkable synthetic poly (cis-1,4-diene), the cis content of which is at least 95% and which has a functional group in the terminal position,

an amphiphilic compound.

With the composition according to the invention, which contains (i) a poly (cis-1,4-diene) with a high cis content and a terminal functional group as well as (ii) an amphiphilic compound, an elastomer can be obtained after crosslinking, the stretch crystallization of which almost corresponds to that of natural rubber.

Polymers in which a functional group is introduced in the terminal position are also referred to as end group functionalized polymers.

Using a synthetic poly (cis-1,4-diene) instead of one

Natural rubber leads to a chemically more uniform material, a very homogeneous mixture with the amphiphilic compound and a good one

Processability (since mastication, ie mechanical breakdown of long-chain rubber molecules, is no longer necessary). In addition, compared to natural rubber, it is independent of seasonal fluctuations.

As is known to the person skilled in the art, the cis content indicates the relative proportion of the repeating units of the polymer which are in the cis-1,4 form.

The cis content is determined by means of NMR spectroscopy. The procedure is as follows:

In 1 H-NMR spectroscopy with field strengths of at least 400 MHz (based on proton resonance), the proportion between 1,2-linkage (“vinyl fraction”) and 1,4-linkage is determined. The chemical shift (measured in CDCl 3 ) in the polyisoprene for the 1,2 linkage is in the range from 4.68 to 4.76 ppm

(terminal protons of the vinyl group) and for the 1,4 linkage in the range of 5.13 ppm (olefinic protons). The two possible 1,4-linkages (cis and frans) are differentiated by means of 13 C-NMR spectroscopy (preferably also at least 400 MHz devices); the differences in the chemical shift in the 1 H-NMR spectrum can only be seen with very detect high magnetic field strengths (well above 400MHz devices). The chemical

Shifts in the 13 C-NMR spectrum are exemplarily for polyisoprene for cis at 23.4 ppm and for frans at 17.2 ppm (methyl groups). The respective proportions are determined by integration, here is a sufficient one

Pay attention to the baseline quality, which can be achieved, for example, by high signal accumulation.

The poly (cis-1,4-diene), in particular the poly (cis-1,4-isoprene), preferably has a cis content of at least 96% or even at least 97%.

The poly (cis-1,4-diene) is preferably a poly (cis-1,4-isoprene) or a poly (cis-1,4-butadiene) or a mixture of these two polymers.

In the case of poly (cis-1,4-isoprene), isoprene is preferably used as the only monomer for the polymerization, and for poly (cis-1,4-butadiene), 1,3-butadiene is preferably used as the only monomer for the polymerization . The poly (cis-1,4-isoprene) therefore preferably contains exclusively monomer units which are derived from isoprene and the poly (cis-1,4-butadiene) preferably contains exclusively monomer units which are derived from 1,3-butadiene.

The synthetic poly (cis-1,4-diene) is preferred over a

Coordination polymerization produced in the presence of a coordination catalyst.

Coordination catalysts for the selective production of poly (cis-1,4-dienes) are described, for example, by Z. Zhang et al., Structure and Bonding, Vol. 137, 2010, pp. 49-108 and in WO 2011/045393 A1.

The coordination catalyst preferably contains a transition metal (eg titanium) and / or a rare earth metal. The rare earth metal is, for example, a lanthanoid (such as neodymium). The coordination catalyst can also contain, for example, an organoaluminum compound.

A suitable coordination catalyst for the preparation of the poly (cis-1,4-diene) with a cis content of at least 95% is, for example, a Ziegler-Natta catalyst.

Due to the use of a coordination catalyst for the polymer synthesis, the poly (cis-1,4-diene) present in the composition according to the invention can also contain a transition metal and / or a rare earth metal. These metals may be present in the polydiene in small amounts and are derived from the catalyst used in the manufacturing process.

The synthetic production of the poly (cis-1,4-diene) enables the exact

Adjustment of the molar mass and can thus be used directly for the production of elastomer components - without the masticating step necessary for natural rubber to reduce molar mass. The poly (cis-1,4-diene) has, for example, a number-average molar mass Mn in the range from 250-400 kg / mol. The

Polydispersity Mw / Mn is, for example, in the range from 2.0-2.8, where Mw is the weight-average molar mass. The synthetic poly (cis-1,4-diene) is preferably exclusively linear. In contrast to natural rubber, disruptive gel components (partially cross-linked structures; detection via the recovery rate in the GPC) are not present or only in very small quantities.

Suitable polymerization conditions for the preparation of poly (cis-1,4-dienes) via coordination polymerization are known to the person skilled in the art. For example, the polymerization takes place in solution. The polymerization temperature is, for example, in the range of 35-80 ° C, more preferably 40-60 ° C and the

The monomer concentration in the polymerization medium (for example in the solution) is, for example, in the range of 5-40% by weight, more preferably 10-30% by weight.

As already mentioned above, the synthetic poly (cis-1,4-diene) has a functional group in the terminal position. Polymers in which a functional group is introduced in the terminal position are also called

termed end-group-functionalized polymers.

The functional group can be, for example, an acidic or basic group.

The functional group is, for example, a carboxyl or carboxylate, hydroxyl, amine or ammonium, ester or cyano group.

The end group functionalization of the synthetic poly (cis-1,4-diene) can, for example, take place exclusively through a specific functional group (for example a carboxyl or carboxylate group). Alternatively, it is also possible that in the end group functionalization of the synthetic poly (cis-1,4-diene) two or more functional groups are introduced (for example in a two- or

multi-stage process of end group functionalization).

In a preferred embodiment, the functional group in the terminal position of the synthetic poly (cis-1,4-diene) is a carboxyl or carboxylate group.

The attachment of terminal functional groups in poly (cis-1,4-dienes), which are produced via coordination polymerization in the presence of a coordination catalyst, is known and is described, for example, in EP 1 873 168 A1, EP 1 939 221 A2 and EP 2 022 803 A2.

For example, the poly (cis-1,4-diene) is polymerized in the presence of the coordination catalyst until the catalyst is suitable for the particular application

The degree of polymerization has been reached and then one is added

Modifier compound through which the terminal functional group is introduced into the polydiene. For example, the modifier compound is added directly to the solution in which the polymerization was carried out. The reaction of the poly (cis-1,4-diene) with the modifier compound can take place, for example, at a temperature which corresponds to the temperature used for the polymerization of the poly (cis-1,4-diene). Alternatively, however, higher temperatures can also be used for the reaction of the poly (cis-1,4-diene) with the modifier compound.

Suitable modifier compounds for the end group functionalization of polydienes are known to the person skilled in the art. The modifier compound is

for example an acid (especially a carboxylic acid), an acid anhydride

(For example C0 2 or a carboxylic acid anhydride), an amine or an ester or a combination of at least two of these compounds.

As stated above, the composition according to the invention contains, in addition to the synthetic poly (cis-1,4-diene) with a high cis content and

End group functionalization is still an amphiphilic compound.

The amphiphilic compound can be of natural origin or have been produced by chemical synthesis.

For example, the amphiphilic compound is a polar lipid, e.g.

Phospholipid, a glycolipid, or a mixture of these two polar lipids; a protein; a fatty acid or a salt of a fatty acid or a fatty acid derivative (eg a glycerol ester of a fatty acid); a surfactant (for example a nonionic surfactant, an anionic surfactant, a cationic surfactant or an amphoteric surfactant) or a mixture of at least two of the aforementioned amphiphilic compounds. In order to reduce the allergenic potential of the composition, it may be preferred that the amphiphilic compound is not a protein and thus the resulting one

Composition is protein-free

Depending on the intended application, the proportion of the amphiphilic compound in the composition can be varied over a wide range. For example, the composition according to the invention contains the amphiphilic compound in an amount of up to 30% by weight, more preferably up to 20% by weight, for example in an amount of 0.05% by weight to 30% by weight, more preferably 0.1% by weight to 20% by weight.

The poly (cis-1,4-diene) and the amphiphilic compound are preferably present as a mixture. The amphiphilic compound is therefore preferably not bound covalently (ie via a chemical bond) to the poly (cis-1,4-diene).

Depending on the intended application, one or more additives can optionally be added to the composition.

If the composition is to be used, for example, for the production of a tire, carbon black and / or one or more inorganic fillers such as SiO 2 can be added to the composition .

For the crosslinking of the polydiene, the composition can contain one or more crosslinkers. Suitable crosslinkers are known to the person skilled in the art. Sulfur or peroxides can be mentioned as examples.

The composition can be present as a solid or also as a solution or dispersion.

The present invention further relates to a method for producing the composition described above, comprising the following method steps:

Production of a poly (cis-1, 4-diene) with a cis content of at least 95% by coordination polymerization in the presence of a

Coordination catalyst,

- Attachment of a functional group in the terminal position of the poly (c / s- 1, 4-diene),

Mixing the poly (cis-1,4-diene) with an amphiphilic compound.

With regard to suitable coordination catalysts and polymerization conditions as well as preferred properties of the poly (c is-1,4-diene), reference can be made to the statements made above.

Coordination catalysts for the selective production of poly (cis-1,4-dienes) are described, for example, by Z. Zhang et al., Structure and Bonding, Vol. 137, 2010, pp. 49-108 and in WO 2011/045393 A1.

The coordination catalyst preferably contains a transition metal (eg titanium) and / or a rare earth metal. The rare earth metal is, for example, a lanthanoid (such as neodymium). The coordination catalyst can also contain, for example, an organoaluminum compound.

A suitable coordination catalyst for the preparation of the poly (cis-1,4-diene) with a cis content of at least 95% is, for example, a Ziegler-Natta catalyst.

Suitable polymerization conditions for the preparation of poly (cis-1,4-dienes) via coordination polymerization are known to the person skilled in the art. For example, the polymerization takes place in solution. The polymerization temperature is, for example, in the range of 35-80 ° C, more preferably 40-60 ° C and the

The monomer concentration in the polymerization medium (for example in the solution) is, for example, in the range of 5-40% by weight, more preferably 10-30% by weight.

Before mixing with the amphiphilic compound, the poly (cis-1,4-diene) is subjected to an end group functionalization, ie a functional group is attached in the terminal position of the poly (cis-1,4-diene). With regard to preferred terminal functional groups and suitable ones

Process conditions for the end group functionalization of the poly (cis-1,4-diene) can be referred to the statements above.

The attachment of terminal functional groups in poly (cis-1,4-dienes), which are produced via coordination polymerization in the presence of a coordination catalyst, is known and is described, for example, in EP 1 873 168 A1, EP 1 939 221 A2 and EP 2 022 803 A2.

For example, the polymerization of the polydiene takes place in the presence of the

Coordination catalyst until the one suitable for the particular application

The degree of polymerization has been reached and then one is added

Modifier compound through which the terminal functional group is introduced into the polydiene. For example, the modifier compound is added directly to the solution in which the polymerization was carried out.

Suitable modifier compounds for the end group functionalization of polydienes are known to the person skilled in the art. The modifier compound is

for example an acid (especially a carboxylic acid), an acid anhydride (for example C0 2 or a carboxylic acid anhydride), an amine or an ester or a combination of at least two of these compounds.

As already mentioned above, the functional group is, for example, a carboxyl or carboxylate, hydroxyl, amine or ammonium, ester or cyano group.

The mixing of the poly (cis-1,4-diene) with the amphiphilic compound can be carried out using customary methods known to the person skilled in the art.

The end group-functionalized poly (cis-1,4-diene) can be mixed with the amphiphilic compound, for example, in the solution in which the polymerization and / or the end group functionalization was (were) carried out beforehand. Alternatively, the poly (cis-1,4-diene) can be separated from the solution in which the polymerisation and / or the end group functionalisation was carried out beforehand, optionally dissolved or dispersed in a liquid and then with the amphiphilic compound be mixed.

The poly (cis-1,4-diene) and the amphiphilic compound are preferably mixed with one another in a liquid medium. In order to achieve the most efficient and homogeneous mixture possible, the poly (cis-1,4-diene) is preferably dissolved in the liquid medium. The amphiphilic compound can also be mixed directly into the poly (cis-1,4-diene) in an internal mixer, a rolling mill or an extruder.

Suitable stirring devices in which the poly (cis-1,4-diene) can be mixed with the amphiphilic compound are known to the person skilled in the art. For example, the stirring device can comprise a stirring and / or kneading mechanism. Internal mixers (eg a punch kneader), rolling mills or extruders can also be used.

The present invention further relates to an elastomeric composition obtainable by crosslinking the end group functionalized poly (cis-1,4-diene) in the composition described above.

Suitable conditions for the crosslinking of the poly (cis-1, 4-diene) are the

Known to those skilled in the art. For example, the crosslinking is initiated by a suitable thermal treatment.

The present invention further relates to a molded article which contains the elastomeric composition described above.

Since the molded body contains the elastomeric composition, one can use the

Shaped bodies also referred to as rubber-elastic or elastomeric shaped bodies.

The molded body is, for example, a tire, a medical product (e.g. a

Hose, protective glove or a condom) or a technical rubber product (e.g. seals, sleeves, semi-finished products).

The present invention further relates to the use of the above

described crosslinkable composition for the preparation of a

rubber-elastic molded body, preferably a tire, in particular the

Tread of a tire or a tube.

The present invention is described in more detail with reference to the following examples.

Examples

Comparative example 1:

A poly (cis-1, 4-isoprene) with a cis content of 98% was obtained via a

Coordination polymerization in the presence of a neodymium-containing catalyst prepared as follows:

Destabilized isoprene was initially introduced in dried cyclohexane (10% by weight), the system was heated to 50 ° C., an Nd-containing catalyst (sold by Comar Chemicals) dissolved in n-hexane (1.0% by volume based on monomer), isothermal Reaction time 3 h. The polymer solution obtained was stopped with isopropanol, stabilized with butylhydroxytoluene and by means of

Coagulation / stripping freed from solvent.

The produced poly (cis-1,4-isoprene) was dissolved in chloroform (10% by weight). In addition, 1% by weight of dicumyl peroxide (crosslinker), based on the polymer, was added to the solution.

After stirring sufficiently vigorously, the solvent was evaporated. A film with a thickness of 1 mm was thermally treated at 160 ° C. in order to initiate crosslinking of the polyisoprene.

The extensional crystallization for the crosslinked composition was then determined as follows:

Based on uniaxially stretched rubber strips, relative crystallinities were determined in the range of 0% to 650% static stretching. The method used here is based on the analysis of one-dimensional X-ray scattering data that were detected perpendicular to the direction of stretching. After quantifying the intensity

(Area evaluation) of amorphous (halo) and crystalline scatter contributions ((200) and (120) reflections) a relative degree of crystallization is determined depending on the static expansion e stat D c, rel = (I 200 + I 120 ) / (Ihaio + I 200 + I 120 ) = I cryst / I total - The relative degrees of crystallization were calculated for 10-15 static elongations and displayed graphically. Based on the graph, linear extrapolation was used to determine the elongation value e onset at which the elongation-induced crystallization began.

At 600% static elongation, a relative degree of crystallization D c, 600 % of about 28% was observed. The onset of crystallization was detected at elongations e onset of approx. 350%.

Comparison example 2:

A poly (cis-1,4-isoprene) was prepared under the same polymerization conditions as in Comparative Example 1. The poly (cis-1,4-isoprene) had a cis content of 98%. After the polymerization had not yet been stopped, CO 2 was added to the reaction solution as a modifier compound for the

End group functionalization of the polyisoprene initiated. Thereby, a poly (cis-1,4-isoprene) with terminal carboxyl groups was obtained. The polymer solution obtained was stopped with isopropanol, stabilized with butylated hydroxytoluene and freed from the solvent in a conventional manner by means of coagulation / stripping.

The produced poly (cis-1,4-isoprene) was dissolved in chloroform (10% by weight). Then 1% by weight of dicumyl peroxide (crosslinker), based on the polymer, was added to the solution. After stirring sufficiently vigorously, the

Solvent evaporated. A film with a thickness of 1 mm was thermally treated at 160 ° C. in order to initiate the crosslinking of the polyisoprene.

The extensional crystallization for the crosslinked composition is then determined according to the method described in Comparative Example 1.

At 600% static elongation, a relative degree of crystallization D c, 600% of about 32.9% was observed. The onset of crystallization was detected at elongations e onset of approx. 350%.

Example 1 according to the invention:

It was initially under the same polymerization conditions as in

Comparative example 1 a poly (c / s-1,4-isoprene) produced. Once, not abgestoppter polymerization was conducted in the reaction solution is C0 2 as

Modifier compound for the end group functionalization of the polyisoprene initiated. This made a poly (cis-1,4-isoprene) with terminal

Carboxyl groups obtained. The poly (cis-1,4-isoprene) had a cis content of 98%. The polymer solution obtained was stabilized with butylated hydroxytoluene and freed from the solvent by means of coagulation / stripping.

The produced poly (cis-1,4-isoprene) was dissolved in chloroform (10% by weight).

In addition, 0.4% by weight of L-alpha-lecithin (a phospholipid that functions as an amphiphilic compound) and 1% by weight of dicumyl peroxide (crosslinker), based on the polymer, were added to the solution.

After stirring sufficiently vigorously, the solvent was evaporated. A film with a thickness of 1 mm was thermally treated at 160 ° C. in order to initiate crosslinking of the polyisoprene.

The extensional crystallization for the crosslinked composition was then determined according to the method described in Comparative Example 1.

At 600% static elongation, a relative degree of crystallization D C, 600% of 46.9% was observed. The onset of crystallization was detected with elongations e onset of approx. 300%.

Comparative example 3:

For comparison purposes, the strain crystallization was also determined on an identically vulcanized natural rubber sample.

At 600% static elongation, a relative degree of crystallization D C, 600% of 42.4% was observed. The onset of crystallization was detected with elongations e onset of approx. 200%.

With the composition according to the invention, which contains the end-group-functionalized poly (cis-1,4-diene) and the amphiphilic compound, after crosslinking has taken place, a stretch crystallization can be achieved which is almost that of the

Corresponds to natural rubber. The relative crystallinities

at 600% elongation D C, 600% exceed the natural rubber sample examined as a reference (SRV) with identical crosslinking.
Expectations

1 composition containing

a crosslinkable synthetic poly (cis-1,4-diene) whose cis content is at least 95% and which has a functional group in the terminal position,

an amphiphilic compound.

The composition of claim 1, wherein the poly (cis-1,4-diene) is a

Is poly (cis-1,4-isoprene) or a poly (cis-1,4-butadiene) or a mixture of these two polymers; and / or wherein the synthetic poly (cis-1,4-diene) is obtainable via a polymerization in the presence of a coordination catalyst which contains a transition metal or a rare earth metal.

3. Composition according to claim 1 or 2, wherein the terminal functional group is a carboxyl or carboxylate, a hydroxyl, an amine or ammonium, an ester or a cyano group.

4. Composition according to any one of the preceding claims, wherein the

amphiphilic compound a polar lipid; a protein; a fatty acid or a salt of a fatty acid; a fatty acid derivative; is a surfactant or a mixture of at least two of these compounds.

5. Composition according to any one of the preceding claims, wherein the

amphiphilic compound is present in the composition in an amount not exceeding 30% by weight.

6. The composition according to any one of the preceding claims, wherein the amphiphilic compound is not covalently bonded to the poly (cis-1,4-diene).

7. Composition according to one of the preceding claims, also one

Containing crosslinkers, in particular sulfur or a peroxide.

8. A method for producing the composition according to any one of claims 1-7, comprising the following process steps:

- Production of a poly (cis-1,4-diene) with a cis content of

at least 95% through a polymerization in the presence of a coordination catalyst,

Attachment of a functional group in the terminal position of the poly) cis- 1, 4-diene),

- Mixing the poly (cis-1,4-diene) with the amphiphilic compound.

9. The method of claim 8, wherein the poly (cis, 4-diene) with a

Reacted modifier compound and thereby introduced a functional group in the terminal position of the poly (cis-1, 4-diene).

10. Elastomeric composition, obtainable by crosslinking the poly (c «-l, 4-diene) in the composition according to any one of claims 1-7.

11. Shaped body containing the elastomeric composition according to claim 10.

12. A molded article according to claim 11, wherein the molded article is a tire

Is a medical device or a technical rubber product.

13. Use of the composition according to any one of claims 1-7 for the production of a shaped body, preferably a tire or a tube.

Documents

Orders

Section Controller Decision Date

Application Documents

# Name Date
1 202117010048-IntimationOfGrant25-10-2023.pdf 2023-10-25
1 202117010048-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [10-03-2021(online)].pdf 2021-03-10
2 202117010048-PatentCertificate25-10-2023.pdf 2023-10-25
2 202117010048-STATEMENT OF UNDERTAKING (FORM 3) [10-03-2021(online)].pdf 2021-03-10
3 202117010048-Written submissions and relevant documents [16-10-2023(online)].pdf 2023-10-16
3 202117010048-NOTIFICATION OF INT. APPLN. NO. & FILING DATE (PCT-RO-105) [10-03-2021(online)].pdf 2021-03-10
4 202117010048-PETITION UNDER RULE 138 [13-09-2023(online)].pdf 2023-09-13
4 202117010048-FORM 1 [10-03-2021(online)].pdf 2021-03-10
5 202117010048-FORM 3 [01-09-2023(online)].pdf 2023-09-01
5 202117010048-DECLARATION OF INVENTORSHIP (FORM 5) [10-03-2021(online)].pdf 2021-03-10
6 202117010048-Information under section 8(2) [01-09-2023(online)].pdf 2023-09-01
6 202117010048-COMPLETE SPECIFICATION [10-03-2021(online)].pdf 2021-03-10
7 202117010048-FORM 18 [31-03-2021(online)].pdf 2021-03-31
7 202117010048-Correspondence to notify the Controller [29-08-2023(online)].pdf 2023-08-29
8 202117010048-US(14)-HearingNotice-(HearingDate-31-08-2023).pdf 2023-08-10
8 202117010048-Proof of Right [13-05-2021(online)].pdf 2021-05-13
9 202117010048-FORM 3 [09-09-2022(online)].pdf 2022-09-09
9 202117010048-FORM-26 [13-05-2021(online)].pdf 2021-05-13
10 202117010048-CLAIMS [25-01-2022(online)].pdf 2022-01-25
10 202117010048-FORM 3 [06-09-2021(online)].pdf 2021-09-06
11 202117010048-FER_SER_REPLY [25-01-2022(online)].pdf 2022-01-25
11 202117010048.pdf 2021-10-19
12 202117010048-FER.pdf 2021-10-19
12 202117010048-OTHERS [25-01-2022(online)].pdf 2022-01-25
13 202117010048-FORM 4(ii) [25-10-2021(online)].pdf 2021-10-25
13 202117010048-Information under section 8(2) [11-01-2022(online)].pdf 2022-01-11
14 202117010048-FORM 3 [06-01-2022(online)].pdf 2022-01-06
15 202117010048-FORM 4(ii) [25-10-2021(online)].pdf 2021-10-25
15 202117010048-Information under section 8(2) [11-01-2022(online)].pdf 2022-01-11
16 202117010048-FER.pdf 2021-10-19
16 202117010048-OTHERS [25-01-2022(online)].pdf 2022-01-25
17 202117010048.pdf 2021-10-19
17 202117010048-FER_SER_REPLY [25-01-2022(online)].pdf 2022-01-25
18 202117010048-FORM 3 [06-09-2021(online)].pdf 2021-09-06
18 202117010048-CLAIMS [25-01-2022(online)].pdf 2022-01-25
19 202117010048-FORM 3 [09-09-2022(online)].pdf 2022-09-09
19 202117010048-FORM-26 [13-05-2021(online)].pdf 2021-05-13
20 202117010048-Proof of Right [13-05-2021(online)].pdf 2021-05-13
20 202117010048-US(14)-HearingNotice-(HearingDate-31-08-2023).pdf 2023-08-10
21 202117010048-Correspondence to notify the Controller [29-08-2023(online)].pdf 2023-08-29
21 202117010048-FORM 18 [31-03-2021(online)].pdf 2021-03-31
22 202117010048-COMPLETE SPECIFICATION [10-03-2021(online)].pdf 2021-03-10
22 202117010048-Information under section 8(2) [01-09-2023(online)].pdf 2023-09-01
23 202117010048-DECLARATION OF INVENTORSHIP (FORM 5) [10-03-2021(online)].pdf 2021-03-10
23 202117010048-FORM 3 [01-09-2023(online)].pdf 2023-09-01
24 202117010048-FORM 1 [10-03-2021(online)].pdf 2021-03-10
24 202117010048-PETITION UNDER RULE 138 [13-09-2023(online)].pdf 2023-09-13
25 202117010048-Written submissions and relevant documents [16-10-2023(online)].pdf 2023-10-16
25 202117010048-NOTIFICATION OF INT. APPLN. NO. & FILING DATE (PCT-RO-105) [10-03-2021(online)].pdf 2021-03-10
26 202117010048-STATEMENT OF UNDERTAKING (FORM 3) [10-03-2021(online)].pdf 2021-03-10
26 202117010048-PatentCertificate25-10-2023.pdf 2023-10-25
27 202117010048-TRANSLATIOIN OF PRIOIRTY DOCUMENTS ETC. [10-03-2021(online)].pdf 2021-03-10
27 202117010048-IntimationOfGrant25-10-2023.pdf 2023-10-25

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3rd: 18 Jan 2024

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