Conjugated diene polymer soluble in organic solvents

Abstract

Disclosed are compositions containing conjugated diene polymers having conjugated diene polymer chains and vinylidene aromatic monomer chains, which are soluble in organic solvents. Disclosed are methods for making the disclosed polymers. Disclosed are compositions containing such polymers.

Description

Technical Field

[0001] Compositions containing a conjugated diene polymer having a conjugated diene polymer chain and a vinylidene aromatic monomer chain are disclosed, said conjugated diene polymer being soluble in an organic solvent. A method for preparing the disclosed polymer is disclosed. Compositions containing such polymers are disclosed. Background Technology

[0002] Polymers prepared from vinylidene aromatic monomers, such as styrene polymers, are used in a variety of polymer systems, including foams, packaging (food packaging), medical, electronics, optics, home appliances, and automotive applications. Polymers containing vinylidene-substituted aromatic monomers and copolymers of vinylidene-substituted aromatic monomers with acrylonitrile have been developed to provide polymers with higher glass transition temperatures and service temperatures; these polymers can be transparent or opaque. Such polymers may not possess excellent impact resistance, therefore modified polymers have been developed to improve impact resistance. These modified polymers may contain impact modifiers, such as conjugated diene polymers, such as butadiene-based rubbers, for example, styrene-acrylonitrile copolymers modified with polybutadiene rubber, acrylonitrile-butadiene-styrene (ABS), and high-impact polystyrene (HIPS). There are limitations on how conjugated diene polymers can be incorporated into such polymer systems based on the particle size of the crosslinked conjugated diene polymer. Expanding the range of possible polymers prepared from conjugated dienes could potentially broaden the applications of conjugated diene polymers in such polymer systems.

[0003] Many polymer producers wish to reduce the disposal of post-consumer polymer systems in landfills and by incineration. These producers want to recycle polymer systems and use them to produce other products. Methods for recycling and reusing post-consumer polymers have been developed, see, for example, WO2022 / 144158, in which polymers containing vinylidene aromatic monomers (such as styrene) are recovered for recycling. In the disclosed methods, the polymer containing vinylidene aromatic monomers is separated from polybutadiene particles. Polybutadiene particles are typically disposed of in landfills or by incineration. There is a need to develop uses for the recycled polybutadiene polymers.

[0004] What is needed is a wider range of conjugated diene polymers, which would help expand the applications of conjugated diene polymers. What is needed are methods for preparing such polymers and methods for using such polymers. Summary of the Invention

[0005] The disclosed composition comprises a conjugated diene polymer containing conjugated diene polymer chains and vinylidene aromatic monomer polymer chains, wherein the polymer is soluble in an organic solvent, wherein soluble means that at least 1 wt%, 5 wt%, or 10 wt% of the conjugated diene polymer dissolves in an organic solvent at about 25°C. The composition may contain a conjugated diene polymer consisting of conjugated diene polymer chains, wherein the polymer is soluble in an organic solvent, wherein soluble means that at least 1 wt%, 5 wt%, or 10 wt% of the conjugated diene polymer dissolves in an organic solvent at about 25°C. The vinylidene aromatic monomer polymer chains are disposed between the conjugated diene polymer chains and optionally at the ends of the conjugated diene polymer chains. The composition may comprise a conjugated diene polymer containing both conjugated diene polymer chains and vinylidene aromatic monomer polymer chains, as well as a conjugated diene polymer having only conjugated diene polymer chains. The vinylidene aromatic monomer polymer chains may be homopolymers of vinylidene aromatic monomers or copolymers of two or more vinylidene aromatic monomers. The polymer chain of the vinylidene aromatic monomer can be a copolymer of one or more vinylidene aromatic monomers and one or more monomers that can copolymerize with the one or more vinylidene aromatic monomers. The one or more monomers that can copolymerize with the one or more vinylidene aromatic monomers can be one or more unsaturated nitrile monomers, such as acrylonitrile. The conjugated diene can be isoprene and / or butadiene. The polymer of the conjugated diene can exhibit a weight-average molecular weight of 20,000 to 200,000 atomic mass units, as determined by gel permeation chromatography using polystyrene standards. The conjugated diene polymer can be dissolved in an organic solvent. The organic solvent can contain one or more aromatic hydrocarbons, aliphatic hydrocarbons, ketones, etc.

[0006] A method for preparing a conjugated diene polymer is disclosed, the conjugated diene polymer comprising a conjugated diene polymer chain and a vinylidene aromatic monomer polymer chain. The method comprises: contacting a composition containing the conjugated diene polymer with a metathesis catalyst (such as a transition metal carbene) in an organic solvent under conditions that cause a portion of the double bonds in the conjugated diene polymer to break, wherein the conjugated diene polymer comprises a conjugated diene polymer chain and a vinylidene aromatic monomer polymer chain, wherein the conjugated diene polymer containing the conjugated diene polymer chain and the vinylidene aromatic monomer polymer chain is prepared, wherein the conjugated diene polymer is soluble in the organic solvent, wherein soluble means that at least 1 wt%, 5 wt%, or 10 wt% of the conjugated diene polymer is soluble in the organic solvent at about 25°C. The metathesis catalyst can be any known metathesis catalyst capable of breaking the double bonds of the conjugated diene polymer. The metathesis catalyst can be one or more transition metal carbenes, which are commonly referred to as Grubbs catalysts. Among useful transition metal carbenes are those corresponding to the following formula: .

[0007] The transition metal carbene can be those corresponding to one of the following formulas: or in: M is a transition metal in group 8 of the periodic table, exemplified by ruthenium or osmium; X and X 1 Each is an anionic ligand independently; L is a neutral electron donor ligand; and, R, R 1 R 2 R 3 R 4 and R 5 Each is independently hydrogen or a substituent selected from the group consisting of: C1-C 20 Alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl, aryl, C1-C 20 Carboxylic acid ester group, C1-C 20 Alkoxy, C2-C 20 alkenyloxy group, C2-C 20 alkynyloxy group, aryloxy group, C2-C 20 alkoxycarbonyl, C1-C 20 Alkyl thiols, aryl thiols, C1-C 20 alkylsulfonyl and C1-C 20 alkylsulfinyl group, wherein the substituent is optionally replaced by one or more portions selected from the group consisting of: C1-C 10 Alkyl, C1-C 10Alkyl, aryl, and functional groups selected from the group consisting of: hydroxyl, thiol, thioether, ketone, aldehyde, ester, ether, amine, imine, amide, nitro, carboxylic acid, disulfide, carbonate, isocyanate, carbodiimide, alkoxycarbonyl, carbamate, and halogen; R 9 Each is hydrogen independently, provided that there is at least one free radical R. 9 Unlike hydrogen, or each of the above are cyclic, straight-chain, or branched alkyl radicals having 1 to 50 carbon atoms or aryl radicals having 6 to 30 carbon atoms, wherein at least one hydrogen atom in the radical is optionally replaced by an alkyl group or functional group, and at least one R 9 Halogen, C1-C4-haloalkyl, C1-C4-alkoxy, C6-C 10 -Aryloxy, cyano, C1-C4-alkoxy-carbonyl, C6-C 10 -Aryloxycarbonyl or aliphatic or aromatic C1-C 10 -acyloxy group; and / or two adjacent R groups 9 It may be part of a cyclic system consisting of a carbon skeleton having 3 to 20 carbon atoms, excluding the carbon atoms in formula (I), wherein at least one hydrogen atom is optionally replaced by an alkyl group or functional group, and / or at least one carbon atom of the ring is optionally replaced by a heteroatom from the group consisting of S, P, O and N; and R 10 It is a hydrogen radical or a cyclic, straight-chain or branched alkyl radical having 1 to 20 carbon atoms, or an aryl radical having 6 to 20 carbon atoms, wherein at least one hydrogen atom in the radical is optionally replaced by an alkyl group or functional group, and R 10 When both are methyl groups, the R group opposite the five-membered ring... 9’ It cannot be part of a cyclic aromatic system with 4 carbon atoms, and does not include carbon atoms.

[0008] The disclosed method can be carried out at temperatures greater than 0°C to about 60°C. The method can be carried out in the absence of oxygen. The conjugated diene polymer used in the disclosed method can be a virgin polymer or a recycled polymer of the conjugated diene, such as those recycled according to WO2022 / 144158, the entire contents of which are incorporated herein by reference for all purposes.

[0009] The conjugated diene polymer formed in the disclosed method can be contacted with a polymer prepared from a vinylidene aromatic monomer, and optionally with a monomer that can copolymerize with the vinylidene aromatic monomer, to form a composition comprising both. This can be achieved by blending the material using known methods (e.g., melt blending). Alternatively, the formed conjugated diene polymer can be contacted with one or more vinylidene aromatic monomers and optionally with monomers that can polymerize with the vinylidene aromatic monomer during the polymerization of such monomers to form a polymer composition of conjugated diene and vinylidene aromatic monomer, and optionally with monomers that can polymerize with the vinylidene aromatic monomer.

[0010] The conjugated diene polymer formed in the disclosed method (which may contain vinylidene aromatic monomer polymer chains and optionally monomers polymerizable with said vinylidene aromatic monomers) can be contacted with polymers containing the conjugated diene polymer and one or more vinylidene aromatic monomers, and other polymer systems containing monomers polymerizable with said vinylidene aromatic monomers. The conjugated diene polymer formed in the disclosed method can be added to such systems either in net form or in an organic solvent. The conjugated diene polymer formed in the disclosed method can compatibilize the components of the added system. Such polymer systems can be acrylonitrile-butadiene-styrene (ABS), styrene-acrylonitrile (SAN), or high-impact polystyrene (HIPS) polymer systems. The conjugated diene polymer formed in the disclosed method can be added to bulk ABS systems to enhance the gloss of such systems. Polymers and polymer chains formed from said monomers refer to polymers or polymer chains containing monomer units derived from said monomer systems. Those skilled in the art will understand the formed monomer units. Attached Figure Description

[0011] Figure 1 A schematic diagram of an initial conjugated diene polymer with conjugated diene chains and vinylidene monomer chains is shown, along with a schematic diagram of the possible chain breakage locations of the conjugated diene polymer chains.

[0012] Figure 2 A schematic diagram of the prepared conjugated diene polymer is shown.

[0013] Figures 4 to 6 Curves showing the analytical results of various soluble conjugated diene polymer samples disclosed in this article.

[0014] Figure 7 This is a graph showing the viscosity of the conjugated diene polymer in Example 2 as a function of time during metathesis. Detailed Implementation

[0015] Although this disclosure has been described in conjunction with certain embodiments, it is to be understood that this disclosure is not limited to the disclosed embodiments, but rather is intended to cover all modifications and equivalent arrangements included within the scope of the appended claims, and its scope is to be interpreted in the broadest possible sense to cover all such modifications and equivalent structures permitted under the legal framework.

[0016] As used herein, "one or more" means that at least one or more of the listed components may be used as disclosed. As used herein, a hydrocarbon group refers to a group containing a backbone of one or more carbon atoms and hydrogen atoms, said group optionally containing one or more heteroatoms. When a hydrocarbon group contains heteroatoms, the heteroatoms may form one or more functional groups well known to those skilled in the art. A hydrocarbon group may contain alicyclic segments, aliphatic segments, aromatic segments, or any combination of such segments. Aliphatic segments may be straight-chain or branched. Aliphatic and alicyclic segments may contain one or more double and / or triple bonds. Hydrocarbon groups include alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, alkylaryl, and aralkyl groups. Alicyclic groups may contain both cyclic and acyclic portions. A hydrocarbon group means a hydrocarbon group having more than one valence state or any subset described, such as alkylene, alkenyl, alkynyl, aryl, cycloalkylene, cycloalkenylene, alkylenearyl, and aralkylene. As used herein, valence means a covalent bond between a hydrocarbon or hydrocarbon-like group and another group, such as a group or atom containing a carbonyl, oxygen, nitrogen, or sulfur, or the base compound mentioned. As used herein, wt% or parts by weight refers to or is based on the weight of the composition unless otherwise stated. Polymers and polymer chains formed from the monomers refer to polymers or polymer chains containing monomer units derived from the monomer system. Those skilled in the art will understand the monomer units formed.

[0017] As used in this article, molecular weight refers to the molecular weight obtained by using narrow-distribution polystyrene (…). polydispersity <1.2) Weight-average molecular weight determined by gel permeation chromatography at ambient temperature using tetrahydrofuran as solvent. The glass transition temperature described herein was determined using differential scanning calorimetry according to test procedure ASTM D3418-15.

[0018] A conjugated diene polymer is disclosed, comprising a conjugated diene polymer chain and a vinylidene aromatic monomer polymer chain. Other polymer chains used in this context refer to other conjugated diene polymer chains or vinylidene aromatic monomer polymer chains, such as polymers of styrene. The conjugated diene polymer is soluble in an organic solvent. A method for preparing the conjugated diene polymer soluble in an organic solvent is disclosed. The method comprises: contacting a conjugated diene polymer in any form with one or more metathesis catalysts (e.g., transition metal carbene compounds commonly referred to as Grubbs catalysts) in an organic solvent under conditions of partial crosslinking of the cleavable conjugated diene to form a conjugated diene polymer with defined solubility. The formed product is soluble in the organic solvent. The formed product may be in the form of a polymer soluble in the organic solvent. The formed product may contain polymer chains based on one or more vinylidene aromatic monomers, wherein the vinylidene aromatic monomer polymer chains are disposed between the conjugated diene polymer chains. A portion of the vinylidene aromatic monomer polymer chain may be disposed at the end of the conjugated diene polymer chain. The resulting product may be soluble in an organic solvent, dispersed in an organic solvent, or may be in a pure state, i.e., undissolved or dispersed in a solvent. The disclosed and formed product may be blended with one or more other polymers as disclosed herein, either in a pure state or in an organic solvent.

[0019] A composition comprising a conjugated diene polymer having polymer chains capable of entanglement with other polymer chains as disclosed herein and soluble in organic solvents is disclosed. The conjugated diene polymer may have polymer chains prepared from one or more vinylidene aromatic monomers bonded thereto, and optionally one or more monomers copolymerizable with the vinylidene aromatic monomers. The polymer chains prepared from one or more vinylidene aromatic monomers may be grafted onto the backbone of the conjugated diene polymer. The conjugated diene polymer may have any form that makes it soluble in organic solvents. The conjugated diene polymer, containing conjugated diene polymer chains and vinylidene aromatic monomer polymer chains, may be blended with one or more polymers prepared from one or more vinylidene aromatic monomers.

[0020] The conjugated diene polymers disclosed herein exhibit a weight-average molecular weight sufficient to form entanglement between the conjugated diene polymer chains. The conjugated diene polymers disclosed herein exhibit a molecular weight sufficient to dissolve the polymer in an organic solvent. Polymers satisfying these criteria may have polymer chains of one or more vinylidene aromatic monomers bonded thereto. The conjugated diene polymer may have a weight-average molecular weight of about 20,000 atomic mass units (amu) or greater, or about 30,000 amu or greater. The conjugated diene polymer may have a weight-average molecular weight of about 200,000 atomic mass units (amu) or less, about 150,000 amu or less, or about 100,000 amu or less. The molecular weight includes the polymer chains of the one or more vinylidene aromatic monomers.

[0021] The organic solvent in which the conjugated diene polymer is soluble can be any organic solvent capable of dissolving the conjugated diene polymer, wherein the conjugated diene polymer contains a conjugated diene polymer chain and a vinylidene aromatic monomer polymer chain. Exemplary organic solvents can be one or more of aromatic hydrocarbons, aliphatic hydrocarbons, ketones, etc. The organic solvent can be one or more of aromatic hydrocarbons or aliphatic hydrocarbons. One or more of the aromatic hydrocarbons can be ethylbenzene, etc.

[0022] The compositions disclosed herein may comprise a conjugated diene polymer comprising conjugated diene polymer chains and vinylidene aromatic monomer polymer chains dissolved or dispersed in an organic solvent. The concentration of the conjugated diene polymer containing the conjugated diene polymer chains and vinylidene aromatic monomer polymer chains in the organic solvent may be any concentration that forms a solution or a stable dispersion. The conjugated diene polymer containing the conjugated diene polymer chains and vinylidene aromatic monomer polymer chains may be present in the organic solvent in an amount up to the point where the solution becomes saturated or the dispersion becomes unstable. The conjugated diene polymer containing the conjugated diene polymer chains and vinylidene aromatic monomer polymer chains may be present in the organic solvent in an amount of about 1 wt% or more, 5 wt% or more, or 10 wt% or more based on the weight of the solution or dispersion. The conjugated diene polymer, which may contain one or more vinylidene aromatic monomer polymer chains, may be present in the organic solvent in an amount of about 40 wt% or less, 30 wt% or less, or 20 wt% or less based on the solution or dispersion.

[0023] In the compositions comprising a conjugated diene polymer and one or more vinylidene aromatic monomer polymer chains, the amount of the vinylidene aromatic monomer polymer chains is the amount that provides the advantages of the compositions disclosed herein. In compositions comprising a conjugated diene polymer chain and one or more vinylidene aromatic monomer polymer chains, the amount of the one or more vinylidene aromatic monomer polymer chains may be about 2 wt% or more, about 5 wt% or more, or about 10 wt% or more. In compositions comprising a conjugated diene polymer and one or more vinylidene aromatic monomer polymer chains, the amount of the one or more vinylidene aromatic monomer polymer chains may be about 50 wt% or less, about 30 wt% or less, or about 20 wt% or less.

[0024] The conjugated diene polymer containing conjugated diene polymer chains and vinylidene aromatic monomer polymer chains used to form the disclosed polymer can exhibit any morphology in which some of the conjugated double bonds can be broken. Such initiating conjugated diene polymers can be in polymer or particulate form. If in particulate form, the particle size can be any size in which some of the double bonds can be broken in the disclosed method. A particle size that allows such compositions to dissolve in nonpolar solvents or form stable dispersions may be advantageous. Such particles can have a particle size of about 0.1 micrometers or larger, about 1 micrometer or larger, or about 5 micrometers or larger. Such particles can have a particle size of about 15.0 micrometers or smaller, about 10.0 micrometers or smaller, or about 8 micrometers or smaller. As used herein, the average particle size of rubber particles will refer to the volume average diameter. In most cases, the volume average diameter of a set of particles is the same as the weight average diameter. Average particle size measurements typically include both the polymer grafted onto the rubber particles and the polymer inclusions within the particles. Unless otherwise stated, the rubber particle size disclosed and claimed herein is determined using a Coulter Multisizer II or II e equipped with ACCUCOMP™ software version 2.01 as follows: Dissolve approximately 3 polymer samples (30–70 mg) in 5 mL of dimethylformamide (DMF) and stir using an ultrasonic bath for approximately 15–20 minutes. Mix 10 mL of electrolyte solution (1% NH4SCN in DMF) with 0.2 mL of the sample solution. Use the Coulter measuring stage with a 20 μm Coulter tube and 1.16 μm calibration material. The coincidence level indicator reading of the instrument should be between 5% and 10%. If the reading is higher than 10%, dilute the sample with the electrolyte solution in a beaker, or if the reading is too low, add more polymer solution dropwise to the DMF. Report the volume-average particle size. Particle size can also be determined using light scattering techniques well known to those skilled in the art.

[0025] Conjugated dienes have groups consisting of two double bonds separated by single bonds, -C=C=C-. The conjugated dienes that can be used in the disclosed compositions are any conjugated dienes containing said groups, wherein said conjugated diene groups are capable of homopolymerization and polymerization with one or more vinylidene aromatic monomers. Exemplary conjugated dienes include butadiene, isoprene, etc. Many conjugated dienes and their polymers are commercially available.

[0026] Vinylene aromatic monomers comprise a vinylene or alkenyl group directly bonded to an aromatic structure. The vinylene aromatic monomer may contain one or more aromatic rings, one or two aromatic rings, or one aromatic ring. The aromatic ring may be unsubstituted or substituted with a substituent that does not interfere with the polymerization of the vinylene aromatic monomer or is formed by a substituent to create a desired structure in the resulting polymer. The substituent may be halogenated or alkyl, such as bromine, chlorine, or C1 to C4 alkyl; or methyl. The alkenyl group comprises a straight-chain or branched carbon chain having one or more double bonds or one double bond. Alkenyl groups that can be used in vinylene aromatic monomers may include those capable of polymerizing to form homopolymers or copolymers when bonded to an aromatic ring. The vinylene may have 2 to 10 carbon atoms, 2 to 4 carbon atoms, or 2 carbon atoms. Exemplary vinylene aromatic monomers include styrene, α-methylstyrene, N-phenylmaleimide, and chlorostyrene; or α-methylstyrene and styrene. The vinylene aromatic monomer may be a monovinylene aromatic monomer containing one unsaturated group. Vinylene aromatic monomers include, but are not limited to, those described in U.S. Patent Nos. 4,666,987, 4,572,819, and 4,585,825, which are incorporated herein by reference. The monomers may correspond to the formula: ; Where R 11 Ar is independently hydrogen or methyl in each occurrence; Ar is independently an aromatic group in each occurrence. Ar may contain one or more aromatic rings, one or two aromatic rings, or one aromatic ring. n is independently 1 to 3, 1 to 2, or 1 in each occurrence. The aromatic ring may be unsubstituted or substituted by a substituent that does not interfere with the polymerization of the vinylidene aromatic monomer or by a substituent used to manufacture the polymer with the desired structure. The substituent may be halogenated or alkyl, such as bromine, chlorine, or C1 to C4 alkyl; or methyl. The vinylidene aromatic monomer may be present in the copolymer in an amount sufficient to cause the copolymer to exhibit advantageous properties associated with the polymer of the vinylidene aromatic monomer (e.g., polystyrene). Advantageous properties of polymers of vinylidene-substituted monomers include processability, stiffness, and thermal stability.

[0027] Polymers or polymer chains prepared from vinylidene aromatic monomers may further comprise one or more olefinically unsaturated monomers copolymerized with vinylidene aromatic monomers. Exemplary olefinically unsaturated monomers copolymerizable with vinylidene aromatic monomers include: conjugated 1,3-dienes (e.g., butadiene, isoprene, etc.); α- or β-unsaturated monocarboxylic acids and their derivatives (e.g., acrylic acid, methacrylic acid, etc.); vinyl halides, such as vinyl chloride, vinyl bromide, etc.; vinyl esters, such as vinyl acetate, vinyl propionate, etc.; olefinically unsaturated dicarboxylic acids and their anhydrides and derivatives, such as maleic acid, fumaric acid, maleic anhydride; dialkyl maleate esters or fumarates, such as dimethyl maleate, diethyl maleate, dibutyl maleate, the corresponding fumarates, N-phenylmaleimide (N-PMI), acrylates (including acrylates and methacrylates), and unsaturated nitrile. Exemplary olefinically unsaturated monomers copolymerizable with vinylidene-substituted aromatic monomers include conjugated 1,3-dienes; α- or β-unsaturated monocarboxylic acids and their derivatives; olefinically unsaturated dicarboxylic acids and their anhydrides and derivatives; acrylates; and unsaturated nitriles. Exemplary olefinically unsaturated monomers polymerizable with vinylidene aromatic monomers may be one or more conjugated dienes, unsaturated nitriles, (meth)acrylates, maleic anhydrides, and maleimides. Exemplary olefinically unsaturated monomers copolymerizable with vinylidene-substituted aromatic monomers include conjugated 1,3-dienes; and unsaturated nitriles, or unsaturated nitriles.

[0028] Polymers or polymer chains prepared from vinylidene-substituted aromatic monomers may contain about 10 wt% or more, about 15 wt% or more, about 20 wt% or more, about 30 wt% or more, 40 wt% or more, or about 50 wt% or more of vinylidene aromatic monomers by weight of the polymer or polymer chain. The polymers or polymer chains disclosed herein may contain about 100 wt% or less, about 90 wt% or less, about 85 wt% or less, or about 80 wt% or less of vinylidene aromatic monomers by weight of the polymer or polymer chain. If present, the amount of such olefin-containing unsaturated comonomers may be about 50 wt% or less, about 40 wt% or less, about 30 wt% or less, about 20 wt% or less, or about 10 wt% or less, based on the weight of the polymer or polymer chain. Such comonomers may be present in amounts of about 1 wt% or more, 10 wt% or more, or about 20 wt% or more based on the weight of the polymer or polymer chain.

[0029] The vinylidene aromatic monomer copolymers or copolymer chains disclosed herein may comprise one or more (meth)acrylates. As used herein, (meth)acrylate refers to a compound having a vinyl group bonded to the carbonyl moiety of an alkyl ester, wherein the carbonyl carbon of the vinyl group further has a hydrogen or methyl group bonded thereto. As used herein, the term (methyl) in this context refers to a compound having either a hydrogen or a methyl group on the carbonyl carbon of the vinyl group. As used herein, acrylate refers to a compound having a vinyl group bonded to the carbonyl moiety of an alkyl ester, wherein the carbonyl carbon of the vinyl group further has a hydrogen group bonded thereto. The use of alkyl acrylates means that the compound mentioned does not have a methyl group on the carbonyl carbon, i.e., R a The alkyl group of a (meth)acrylate may have one or more, two or more, three or more, or four carbon atoms. The alkyl group of a (meth)acrylate may have 30 or fewer, 10 or fewer, 6 or fewer, or 4 or fewer carbon atoms. Useful (meth)acrylates include those compounds corresponding to the following formula: Where R a It is independently H or -CH3 each time it appears; and R b Each time it appears, it independently allows the formation of alkyl groups in homopolymers with glass transition temperatures of about 100°C or higher for (meth)acrylates. b It can be C1 to C 30 Alkyl or C 1-10 Alkyl group. R b It can be C2 to C 30 Alkyl, C 2-10 Alkyl, C 2-6 Alkyl or C 3-4 Alkyl group. The (meth)acrylate may contain a mixture of (meth)acrylates, such that for a (meth)acrylate R... b For C1, while for one or more other (meth)acrylates R b It can be C2- 30 Alkyl, C 2-10 Alkyl, C 2-6 Alkyl or C 3-4Alkyl groups. The one or more (meth)acrylates may include methyl methacrylate and one or more of ethyl methacrylate, propyl methacrylate, butyl methacrylate, pentyl methacrylate, and hexyl methacrylate. Examples of the one or more (meth)acrylates include lower alkyl (meth)acrylates such as methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, pentyl methacrylate, and hexyl methacrylate. The (meth)acrylate may be one or more linear C8 to C14 acrylates based on copolymer weight. 16 Alkyl acrylates. The one or more (meth)acrylates may include methyl (meth)acrylate and one or more of ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, amyl (meth)acrylate, and hexyl (meth)acrylate. The one or more (meth)acrylates may include methyl (meth)acrylate and butyl (meth)acrylate.

[0030] The vinylidene aromatic monomer copolymers or copolymer chains may further comprise one or more unsaturated nitrile groups. Unsaturated nitrile groups include, but are not limited to, acrylonitrile, methacrylonitrile, ethyl acrylonitrile, fumaric acid, and mixtures thereof. The unsaturated nitrile group may be acrylonitrile. The unsaturated nitrile group is used in the copolymer chain and copolymer to enhance glass transition temperature, transparency, chemical resistance, etc. The vinylidene aromatic monomer copolymers or copolymer chains disclosed herein may contain one or more unsaturated nitrile groups in amounts of about 0 wt% or more, about 1 wt% or more, about 2 wt% or more, about 5 wt% or more, or about 10 wt% or more of the copolymer or copolymer chain. The copolymers and copolymer chains disclosed herein may contain one or more unsaturated nitrile groups in amounts of about 40 wt% or less, about 35 wt% or less, about 30 wt% or less, about 25 wt% or less, or about 20 wt% or less of the polymer chain or copolymer.

[0031] A method for preparing a conjugated diene polymer is disclosed. The method includes contacting a composition containing the conjugated diene polymer with a metathesis catalyst (such as a transition metal carbene) in an organic solvent under conditions that cause a portion of the double bonds in the conjugated diene polymer to break, thereby preparing the conjugated diene polymer, wherein the conjugated diene polymer is soluble in the organic solvent, wherein soluble means that at least 1 wt%, 5 wt%, or 10 wt% of the conjugated diene polymer is soluble in the organic solvent at about 25°C.

[0032] The metathesis catalyst can be any catalyst capable of breaking the double bonds of conjugated diene polymers. Exemplary metathesis catalysts include: first- and second-generation Grubbs catalysts; molybdenum-based Schrock catalysts; molybdenum hexacarbonyl (Mo(CO)6); rhenium pentacarbonyl (Re(CO)5); ruthenium tetracarbonyl (Ru(CO)4); tungsten pentacarbonyl ((CO)5W=C(CH3)(OCH3)); tungsten hexachloride; methyllithium; tetramethyltin; and molybdenum pentachloride, etc.

[0033] Transition metal carbenes are commonly referred to as Grubbs catalysts. Exemplary transition metal carbenes include imidazolium-based metal carbenes, which belong to those known as Grubbs 2-carbenes. Useful transition metal carbenes are imidazolium-based metal carbenes that include those carbenes corresponding to the following formula: Wherein: M is a transition metal, exemplarily ruthenium or osmium; the transition metal may be ruthenium; X and X' are each independently anionic ligands; L is a neutral electron donor ligand; and R, R 1 R 2 R 3 R 4 and R 5 Each is independently hydrogen or a substituent selected from the group consisting of: C1-C 20 Alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl, aryl, C1-C 20 Carboxylic acid ester group, C1-C 20 Alkoxy, C2-C 20 alkenyloxy group, C2-C 20 alkynyloxy group, aryloxy group, C2-C 20 Alkoxycarbonyl, C1-C 20 Alkyl thiols, aryl thiols, C1-C 20 alkyl sulfinyl and C1-C 20 alkylsulfonyl group, wherein the substituent may optionally be partially substituted by one or more groups selected from the group consisting of: C1-C 10 Alkyl, C1-C 10Alkoxy, aryl, and functional groups selected from the group consisting of: hydroxyl, thiol, thioether, ketone, aldehyde, ester, ether, amine, imine, amide, nitro, carboxylic acid, disulfide, carbonate, isocyanate, carbodiimide, alkoxycarbonyl, carbamate, and halogen. L is a neutral two-electron donor; it can be one or more amines, imines, phosphine, hypophosphite, antimony, arsine, CO, carbonyl compounds, nitriles, alcohols, thiols, ethers, and thioethers. L can be independently selected from the group consisting of: phosphine, sulfonated phosphite, phosphite, hypophosphite, phosphite, arsine, antimony, ether, amine, amide, imine, sulfoxide, carboxyl, nitrosyl, pyridine, and thioether. L can be having the formula PR. 6 R 7 R 8 Phosphine, of which R 6 R 7 and R 8 Each is independently aryl, C1-C 10 Alkyl or cycloalkyl. L can be -P(cyclohexyl)3, -P(cyclopentyl)3, -P(isopropyl)3, and -P(phenyl)3. R 6 R 7 and R 8 Each time it appears, it is independently methyl, ethyl, cyclopentyl, cyclohexyl, or phenyl. X and X' can be the same or different, and each is an anionic ligand from the group consisting of halides, pseudohalides, hydroxides, alkoxides, carboxylic acid esters, and sulfonates. X and X 1 Each can be a hydrogen, a halide, or a substituent selected from the group consisting of: C1-C 20 Alkyl, aryl, C1-C 20 Alkyl oxides, aromatic oxides, C3-C 20 Alkyl diketoester group, aryl diketoester group, C1-C 20 Carboxylic acid ester group, aryl sulfonate group, C1-C 20 Alkyl sulfonate group, C1-C 20 Alkyl thiols, aryl thiols, C1-C 20 alkylsulfonyl and C1-C 20 alkylsulfinyl group, wherein the substituent may optionally be partially substituted by one or more groups selected from the group consisting of: C 1-10 Alkyl, C1-C 10 Alkyl, aryl, and halides. X and X' can be the same and each can be a halide. R 1 It is phenyl or -C=C(CH3)2. X, X 1Each can be independently selected from the following groups: halides, CF3CO2, CH3CO2, CFH2CO2, (CH3)3CO, (CF3)2(CH3)CO, (CF3)(CH3)2CO, PhO, MeO, EtO, toluenesulfonates, methanesulfonates, and trifluoromethanesulfonates. X and X 1 Each can be a chloride. R can be hydrogen. 1 It may be phenyl or vinyl, optionally substituted with one or more portions selected from the group consisting of: C1-C5 alkyl, C1-C5 alkoxy, phenyl, and functional groups selected from the group consisting of: hydroxyl, thiol, thioether, ketone, aldehyde, ester, ether, amine, imine, amide, nitro, carboxylic acid, disulfide, carbonate, isocyanate, carbodiimide, alkoxycarbonyl, carbamate, and halogen. R 1 It can be phenyl or -C=C(CH3)2. R 6 and R 7 They can be combined to form cycloalkyl or aryl groups; cyclopentyl or cyclohexyl moieties. R 6 and R 7 They can be the same and can be either hydrogen or phenyl. R 8 and R 9 Each is independently either a substituted or unsubstituted aryl group, or the same and is phenyl. R 8 and R 12 Each is an independent style , where R 12 Each time it appears, it is independently hydrogen or C. 1-10 Alkyl, C 1-10 Alkoxy, aryl, or a functional group selected from hydroxyl, thiol, thioether, ketone, aldehyde, ester, ether, amine, imine, amide, nitro, carboxylic acid, disulfide, carbonate, isocyanate, carbodiimide, alkoxycarbonyl, carbamate, and halogen. R 12 It can be hydrogen, methyl, or isopropyl independently.

[0034] Useful transition metal carbides are those that include metal carbides corresponding to the following formula: : Where X, X', L, and M are as described above; and R 9 It is hydrogen independently each time it appears, provided that there is at least one free radical R. 9 Unlike hydrogen, or each of the above are cyclic, straight-chain, or branched alkyl radicals having 1 to 50 carbon atoms or aryl radicals having 6 to 30 carbon atoms, wherein at least one hydrogen atom in the radical is optionally replaced by an alkyl group or functional group, and at least one R 9 Halogen, C1-C4-haloalkyl, C1-C4-alkoxy, C6-C10 -Aryloxy, cyano, C1-C4-alkoxy-carbonyl, C6-C 10 -Aryloxycarbonyl or aliphatic or aromatic C1-C 10 -acyloxy group; and / or Two adjacent R 9 It may be part of a cyclic system consisting of a carbon skeleton having 3 to 20 carbon atoms, excluding the carbon atoms in formula (I), wherein at least one hydrogen atom is optionally replaced by an alkyl group or functional group, and / or at least one carbon atom in the ring is optionally replaced by a heteroatom from the group consisting of S, P, O and N; and R 10 It is a hydrogen radical or a cyclic, straight-chain or branched alkyl radical having 1 to 20 carbon atoms, or an aryl radical having 6 to 20 carbon atoms, wherein at least one hydrogen atom in the radical is optionally replaced by an alkyl group or functional group, and when R 10 When both are methyl groups, the R group opposite the five-membered ring... 9’ It cannot be part of a cyclic aromatic system with 4 carbon atoms, and does not include carbon atoms. R 9 It can be hydrogen independently each time it appears, provided that at least one R is present. 9 Unlike hydrogen, or cyclic, straight-chain, or branched alkyl radicals having 1 to 20 carbon atoms, or aryl radicals having 6 to 20 carbon atoms, wherein at least one hydrogen atom of the alkyl radical or aryl radical is optionally substituted with a functional group, and at least one R 9 Halogen, C1-C4-haloalkyl, C1-C4-alkoxy, C6-C 10 -Aryloxy, cyano, C1-C4-alkoxycarbonyl, C6-C 10 -Aryloxycarbonyl or aliphatic or aromatic C1-C 10 -Acyloxy group. All R 9’ Each can be hydrogen, except for R adjacent to the carbon bonded to oxygen. 9 It is a cyclic, straight-chain, or branched alkyl radical having 1 to 20 carbon atoms or an aryl radical having 6 to 20 carbon atoms, wherein at least one hydrogen atom in the radical is optionally replaced by an alkyl group or functional group, or is a halogen, C1-C4-haloalkyl, C1-C4-alkoxy, or C6-C 10 -Aryloxy, cyano, C1-C4-alkoxycarbonyl, C6-C 10 -Aryloxycarbonyl or aliphatic or aromatic C1-C 10 -acyloxy group; or all R 9’ Each can be hydrogen, except for R adjacent to the carbon indirectly bonded to M. 9It is a cyclic, straight-chain, or branched alkyl radical having 1 to 20 carbon atoms or an aryl radical having 6 to 20 carbon atoms, wherein at least one hydrogen atom in the radical is optionally replaced by an alkyl group or functional group, or is a halogen, C1-C4-haloalkyl, C1-C4-alkoxy, or C6-C 10 -Aryloxy, cyano, C1-C4-alkoxycarbonyl, C6-C 10 -Aryloxycarbonyl or aliphatic or aromatic C1-C 10 -Acyloxy group. All R 9’ Each can be hydrogen, except for R which is bonded to the second carbon from the carbon adjacent to the carbon indirectly bonded to M. 9 It is a cyclic, straight-chain, or branched alkyl radical having 1 to 20 carbon atoms or an aryl radical having 6 to 20 carbon atoms, wherein at least one hydrogen atom in the radical is optionally replaced by an alkyl group or functional group, or is a halogen, C1-C4-haloalkyl, C1-C4-alkoxy, or C6-C 10 -Aryloxy, cyano, C1-C4-alkoxycarbonyl, C6-C 10 -Aryloxycarbonyl or aliphatic or aromatic C1-C 10 -Acyloxy group. All R 9’ All can be hydrogen, except for R which is bonded to the second carbon from the carbon bonded to oxygen. 9 It is a cyclic, straight-chain, or branched alkyl radical having 1 to 20 carbon atoms or an aryl radical having 6 to 20 carbon atoms, wherein at least one hydrogen atom in the radical is optionally replaced by an alkyl group or functional group, or is a halogen, C1-C4-haloalkyl, C1-C4-alkoxy, or C6-C 10 -Aryloxy, cyano, C1-C4-alkoxycarbonyl, C6-C 10 -Aryloxycarbonyl or aliphatic or aromatic C1-C 10 - Acyloxy group. The R on the adjacent carbon atom of the five-membered ring. 9’ Each is a hydrogen radical or an aryl radical having 6 to 20 carbon atoms, wherein at least one hydrogen atom of the aryl radical is optionally replaced by an alkyl group or functional group, or each is a halogen, C1-C4-haloalkyl, C1-C4-alkoxy, or C6-C 10 -Aryloxy, cyano, C1-C4-alkoxycarbonyl, C6-C 10 -Aryloxycarbonyl or aliphatic or aromatic C1-C 10 -acyloxy group, and the other two R 9 This is part of a cyclic aromatic system having 4 to 14 carbon atoms, wherein at least one hydrogen atom is optionally replaced by an alkyl group or functional group. The R atoms on the two carbons closest to the unbonded oxygen atoms in the five-membered ring are... 9’They may be the same or different, and each is a hydrogen radical or an aryl radical having 6 to 20 carbon atoms, wherein at least one hydrogen atom in the aryl radical is optionally replaced by an alkyl group or functional group, or each is a halogen, C1-C4-haloalkyl, C1-C4-alkoxy, C6-C 10 -Aryloxy, cyano, C1-C4-alkoxycarbonyl, C6-C 10 -Aryloxycarbonyl or aliphatic or aromatic C1-C 10 - Acyloxy group; R on the two carbons closest to the oxygen atom in the five-membered ring. 9’ It is part of a cyclic aromatic system having 4 to 14 carbon atoms, wherein at least one hydrogen atom is optionally replaced by an alkyl group or a functional group.

[0035] Examples of transition metal carbene include the following: , , , , or Where Mes is Also known as mesitylene, i-Pr is isopropyl, Ph is phenyl and PCy3 is -P(cyclohexyl)3. Imidazolyl-based metal carbene is commercially available and can be synthesized by the method disclosed in WO2000 / 071554, the full contents of which are incorporated herein by reference for all purposes.

[0036] The starting conjugated diene polymer can be any conjugated diene polymer as described herein. The conjugated diene polymer may contain a chain of vinylidene aromatic monomer polymers, optionally containing monomers copolymerizable with the vinylidene aromatic monomers. A portion of the starting conjugated diene polymer may have a chain of vinylidene aromatic monomer polymers branched to the main link of the conjugated diene polymer chain, the polymer chain optionally containing monomers copolymerizable with the vinylidene aromatic monomers. The monomers copolymerizable with the vinylidene aromatic monomers can be any one or more of the one or more monomers copolymerizable with vinylidene aromatic monomers as described herein. The starting conjugated diene polymer can be in polymer form or the polymer can be in particulate form. The starting polymer or particulates can be virgin polymers or particulates, recycled polymers or particulates, or mixtures thereof. The conjugated diene polymers used in the methods disclosed herein can be virgin conjugated diene polymers or recycled conjugated diene polymers, such as those recycled under WO2022 / 144158, the entire contents of which are incorporated herein by reference for all purposes.

[0037] Polymers prepared by the disclosed method may comprise any of the disclosed conjugated diene polymers, optionally containing vinylidene aromatic monomer polymer chains, optionally containing monomers copolymerizable with the vinylidene aromatic monomers, which may be disposed between two or more conjugated diene polymer chains. Polymers or particles prepared by the disclosed method may comprise any of the disclosed conjugated diene polymers, optionally containing vinylidene aromatic monomer polymer chains, said polymer chains optionally containing monomers copolymerizable with the vinylidene aromatic monomers, which may be disposed at the ends of the conjugated diene polymer chains. Polymers prepared by the disclosed method meet the criterion of being soluble in organic solvents, wherein soluble means that at least 1 wt%, 5 wt%, or 10 wt% of the conjugated diene polymer dissolves in an organic solvent at about 25°C. The prepared polymers may only partially break the original conjugated double bonds, and therefore retain a significant amount of conjugated double bonds in the final product.

[0038] The disclosed method can be carried out at temperatures greater than 0°C, about 10°C or higher, or about 20°C or higher. The disclosed method can be carried out at temperatures about 60°C or lower, about 50°C or lower, or about 40°C or lower. The method can be carried out at ambient temperatures within the listed range. The metathesis catalyst (such as a transition metal carbene) can be present in the reaction mixture in any amount that catalyzes the breaking of unsaturated bonds in the conjugated diene polymer. Based on the amount of conjugated diene polymer present, the amount of transition metal carbene present in the reaction mixture can be about 10 ppm (parts per million) or more, about 50 ppm or more, or about 100 ppm or more. Based on the amount of conjugated diene polymer present, the amount of transition metal carbene present in the reaction mixture can be about 1000 ppm or less, about 500 ppm or less, or about 300 ppm or less. The method can be carried out for a sufficient period of time to prepare the conjugated diene polymer as described herein, which meets the criterion of being soluble in an organic solvent, wherein soluble means that at least 1 wt%, 5 wt%, or 10 wt% of the conjugated diene polymer dissolves in a nonpolar organic solvent at about 25°C. The method can be carried out for about 1 minute or longer, 5 minutes or longer, or about 10 minutes or longer. The method can be carried out for about 120 minutes or less, 60 minutes or less, or about 30 minutes or less. The method can be carried out in the absence of oxygen.

[0039] The resulting polymer can remain dissolved in an organic solvent or can be separated using common separation techniques including filtration, centrifugation, etc. The resulting conjugated diene polymer can be blended with one or more other polymers, such as polymers of one or more vinylidene aromatic monomers, and optionally monomers, polyamides, conjugated diene polymers, etc., that can polymerize with vinylidene aromatic monomers as disclosed herein. The blending can utilize conjugated diene polymers dissolved in organic solvents or conjugated diene polymers existing in pure form.

[0040] Compositions comprising the conjugated diene polymer disclosed herein and one or more other polymers are disclosed. The compositions may be blends of polymers. The blends may comprise two or more polymers having significantly different polarities, one of which is a polar polymer and the other a nonpolar polymer. The blends may comprise one or more other polymers, such as polymers of vinylidene aromatic monomers, and optionally monomers polymerizable with said vinylidene aromatic monomers, polyamides, conjugated dienes, etc. The blending may be carried out using the conjugated diene polymer dissolved in an organic solvent or in its pure form.

[0041] A method for compatibilizing different polymers using the conjugated diene polymer prepared herein is disclosed. This is achieved by blending the conjugated diene polymer with two or more polymers, such as conjugated diene polymer particles and polymers prepared from one or more vinylidene aromatic monomers, and optionally monomers as disclosed herein that can polymerize with said vinylidene aromatic monomers.

[0042] The conjugated diene polymers disclosed herein can be incorporated into methods for preparing impact-modified polymers of vinylidene aromatic monomers, such as through bulk polymerization. These modified vinylidene aromatic monomer polymers can exhibit improved gloss.

[0043] Figure 1 A schematic diagram of the starting polymer 1 of the conjugated diene and a schematic diagram of the starting polymer of the conjugated diene and the location 2 where chain severance can occur are shown. The diagram also shows the conjugated diene chain 3, the vinylidene aromatic polymer chain 4, and the location of crosslinking severance 5. Figure 2 The diagram shows the soluble segments of the conjugated diene polymer chain and the bonding of polymer segments of conjugated diene chain 3 with segments of vinylidene aromatic monomer polymer chain 4.

[0044] Diagram / Implementation Plan 1. A composition comprising a conjugated diene polymer containing a conjugated diene polymer chain and a vinylidene aromatic monomer polymer chain, wherein the polymer is soluble in an organic solvent, wherein soluble means that at least 1 wt%, 5 wt%, or 10 wt% of the conjugated diene polymer dissolves in the organic solvent at about 25°C.

[0045] 2. The composition according to embodiment 1, comprising a conjugated diene polymer, wherein the polymer is soluble in an organic solvent, wherein soluble means that at least 1 wt%, 5 wt%, or 10 wt% of the conjugated diene polymer is soluble in the organic solvent at about 25°C.

[0046] 3. The composition according to embodiment 1 or 2, wherein the vinylidene aromatic monomer polymer chains are located between conjugated diene polymer chains.

[0047] 4. The composition according to any one of the foregoing embodiments, comprising a polymer chain consisting of one or more vinylidene aromatic monomers.

[0048] 5. The composition according to any one of the foregoing embodiments, comprising one or more vinylidene aromatic monomers and a polymer chain of one or more monomers capable of polymerizing with said one or more vinylidene aromatic monomers.

[0049] 6. The composition according to any one of the foregoing embodiments, wherein the polymer chain of the one or more vinylidene aromatic monomers comprises one or more vinylidene aromatic monomers and one or more monomers capable of polymerizing with the vinylidene aromatic monomers, wherein the one or more monomers comprise one or more of unsaturated nitrile, (meth)acrylic acid, maleic anhydride and maleimide.

[0050] 7. The composition according to any one of the foregoing embodiments comprises one or more vinylidene aromatic monomers and one or more unsaturated nitrile polymer chains.

[0051] 8. The composition according to any one of the foregoing embodiments, comprising a polymer chain comprising styrene and acrylonitrile.

[0052] 9. The composition according to any one of the embodiments, wherein the conjugated diene polymer chain comprises isoprene or butadiene.

[0053] 10. The composition according to any one of the foregoing embodiments, wherein the conjugated diene polymer is dissolved in an organic solvent.

[0054] 11. The composition according to any one of the foregoing embodiments, wherein the conjugated diene polymer is dissolved in an organic solvent comprising one or more aromatic hydrocarbons, aliphatic hydrocarbons, and ketones.

[0055] 12. The composition according to any one of the foregoing embodiments, wherein the conjugated diene polymer is dissolved in an organic solvent comprising one or more aromatic hydrocarbons.

[0056] 13. The composition according to any one of the foregoing embodiments, wherein the conjugated diene comprises butadiene, the vinylidene aromatic monomer comprises one or more styrene-based monomers, and the one or more monomers polymerizable with the one or more vinylidene aromatic monomers comprise one or more unsaturated nitrile monomers.

[0057] 14. The composition according to any one of the foregoing embodiments, wherein the conjugated diene comprises butadiene, the vinylidene aromatic monomer comprises styrene, and the one or more monomers capable of polymerizing with the vinylidene aromatic monomer comprise acrylonitrile.

[0058] 15. The composition according to any one of the foregoing embodiments, comprising the conjugated diene polymer having grafted polymer chains prepared from one or more vinylidene aromatic monomers.

[0059] 16. The composition according to any one of the foregoing embodiments, comprising the conjugated diene polymer blended with a polymer comprising a vinylidene aromatic monomer.

[0060] 17. A method comprising: contacting the conjugated diene polymer with a metathesis catalyst in an organic solvent under conditions that cause a portion of the double bonds in the conjugated diene polymer chain and the vinylidene aromatic monomer polymer chain to break, wherein the conjugated diene polymer containing the conjugated diene polymer chain and the vinylidene aromatic monomer polymer chain is prepared, wherein the conjugated diene polymer is soluble in the organic solvent, wherein soluble means that at least 1 wt%, 5 wt%, or 10 wt% of the conjugated diene polymer is soluble in the organic solvent at about 25°C.

[0061] 18. The method according to embodiment 17, wherein the metathesis catalyst comprises a transition metal carbene.

[0062] 19. The method according to embodiment 17 or 18, wherein the metathesis catalyst comprises a transition metal carbene corresponding to the formula... ; in: M is a transition metal in group 8 of the periodic table; X and X 1 Each is an anionic ligand independently; L is a neutral electron donor ligand; and... R and R 1 Each is independently hydrogen or a substituent selected from the group consisting of: C1-C 20 Alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl, aryl, Cι-C 20 Carboxylic acid ester group, C1-C 20 Alkoxy, C2-C 20 alkenyloxy group, C2-C 20 alkynyloxy group, aryloxy group, C2-C 20 Alkoxycarbonyl, C1-C 20 Alkyl thiols, aryl thiols, C1-C 20 alkylsulfonyl and C1-C 20 alkylsulfinyl group, wherein the substituent is optionally replaced by one or more portions selected from the group consisting of: C1-C 10 Alkyl, C1-C 10 Alkoxy, aryl, and functional groups selected from the group consisting of: hydroxyl, thiol, thioether, ketone, aldehyde, ester, ether, amine, imine, amide, nitro, carboxylic acid, disulfide, carbonate, isocyanate, carbodiimide, alkoxycarbonyl, carbamate, and halogen.

[0063] 20. The method according to any one of embodiments 17 to 19, wherein the metathesis catalyst comprises a transition metal carbene, the transition metal carbene corresponding to the structure in: M is a transition metal in group 8 of the periodic table; X and X 1 Each is an anionic ligand independently; L is a neutral electron donor ligand; and R, R 1 R 2 R 3 R 4 and R 5 Each is independently hydrogen or a substituent selected from the group consisting of: C1-C 20 Alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl, aryl, C1-C 20 Carboxylic acid ester group, C1-C 20 Alkoxy, C2-C 20 alkenyloxy group, C2-C 20alkynyloxy group, aryloxy group, C2-C 20 Alkoxycarbonyl, C1-C 20 Alkyl thiols, aryl thiols, C1-C 20 alkylsulfonyl and C1-C 20 alkylsulfinyl group, wherein the substituent is optionally replaced by one or more portions selected from the group consisting of: C1-C 10 Alkyl, C1-C 10 Alkoxy, aryl, and functional groups selected from the group consisting of: hydroxyl, thiol, thioether, ketone, aldehyde, ester, ether, amine, imine, amide, nitro, carboxylic acid, disulfide, carbonate, isocyanate, carbodiimide, alkoxycarbonyl, carbamate, and halogen.

[0064] 21. The method according to implementation scheme 20, wherein: M is either ruthenium or osmium; L and L are each independently selected from the group consisting of: phosphine, sulfonated phosphite group, hypophosphite group, phosphite group, arsine, antimony, ether, amine, amide, imine, sulfoxide, carboxyl group, nitrosyl group, pyridine, and thioether; and, X and X 1 Each substituent is independently hydrogen, a halide, or selected from the group consisting of: C1-C 20 Alkyl, aryl, C1-C 20 Alkyl oxides, aromatic oxides, C3-C 20 Alkyl diketoester group, aryl diketoester group, C1-C 20 Carboxylic acid ester group, aryl sulfonate group, C1-C 20 Alkyl sulfonate group, C1-C 20 Alkyl thiols, aryl thiols, C1-C 20 alkylsulfonyl and C1-C 20 alkylsulfinyl group, wherein the substituent is optionally replaced by one or more portions selected from the group consisting of: C 1-10 Alkyl, C1-C 10 Alkoxy, aryl, and halogenated compounds.

[0065] 22. The method according to implementation scheme 20, wherein M is ruthenium; X and X 1 Each of the following groups is independently selected: halides, CF3CO2, CH3CO2, CFH2CO2, (CH3)3CO, (CF3)2(CH3)CO, (CF3)(CH3)2CO, PhO, MeO, EtO, toluenesulfonates, methanesulfonates and trifluoromethanesulfonates; L is the formula PR 6 R 7 R8 Phosphine, of which R 6 R 7 and R 8 Each is independently aryl, C1-C 10 Alkyl or cycloalkyl; R is hydrogen; and R 1 It is phenyl or vinyl, optionally substituted with one or more of the following groups: C1-C5 alkyl, C1-C5 alkoxy, phenyl and functional groups selected from the group consisting of: hydroxyl, thiol, thioether, ketone, aldehyde, ester, ether, amine, imine, amide, nitro, carboxylic acid, disulfide, carbonate, isocyanate, carbodiimide, alkoxycarbonyl, carbamate and halogen.

[0066] 23. The method according to embodiment 17 or 18, wherein the metathesis catalyst comprises a transition metal carbene, the transition metal carbene corresponding to the formula... ; M is a transition metal in group 8 of the periodic table; X and X' are the same or different and are each anionic ligands; R 9 Each time it appears, it is independently hydrogen, provided that there is at least one free radical R. 9 Unlike hydrogen, or each being a cyclic, straight-chain, or branched alkyl radical having 1 to 50 carbon atoms or an aryl radical having 6 to 30 carbon atoms, wherein at least one hydrogen atom is optionally replaced by an alkyl group or functional group, and at least one R 9 It is a halogen, C1-C4-haloalkyl, C1-C4-alkoxy, C6-C 10 -Aryloxy, cyano, C1-C4-alkoxy-carbonyl, C6-C 10 -Aryloxycarbonyl or aliphatic or aromatic C1-C 10 -acyloxy group; and / or Two adjacent R 9 It may be part of a cyclic system consisting of a carbon skeleton having 3 to 20 carbon atoms, excluding the carbon atoms in formula (I), wherein at least one hydrogen atom is optionally replaced by an alkyl group or functional group, and / or at least one carbon atom of the ring is optionally replaced by a heteroatom from the group consisting of S, P, O and N; and R 10 It is a hydrogen radical or a cyclic, straight-chain or branched alkyl radical having 1 to 20 carbon atoms, or an aryl radical having 6 to 20 carbon atoms, wherein at least one hydrogen atom in the radical is optionally replaced by an alkyl group or functional group, and when R 10When it is also a methyl group, the R opposite to the five-membered ring... 9 It may not be part of a cyclic aromatic system with four carbon atoms, may not include carbon atoms, and... L is a neutral two-electron donor; derived from the group consisting of amines, imines, phosphines, phosphites, antimony, arsine, CO, carbonyl compounds, nitriles, alcohols, thiols, ethers, and thioethers.

[0067] 24. The method according to implementation scheme 23, wherein: M is either ruthenium or osmium. X and X' may be the same or different and are each anionic ligands derived from halides, pseudohalides, hydroxides, alkoxides, carboxylic acid esters, and sulfonates; R 9 It is hydrogen independently each time it appears, provided that at least one R is present. 9 Unlike hydrogen, or each being a cyclic, straight-chain, or branched alkyl radical having 1 to 20 carbon atoms or an aryl radical having 6 to 20 carbon atoms, wherein at least one hydrogen atom in the alkyl radical and aryl radical is optionally replaced by a functional group, and at least one R 9 It is a halogen, C1-C4-haloalkyl, C1-C4-alkoxy, C6-C 10 -Aryloxy, cyano, C1-C4-alkoxycarbonyl, C6-C 10 -Aryloxycarbonyl or aliphatic or aromatic C1-C 10 -acyloxy group, or All R 9 All are hydrogen, except for R, which is adjacent to the carbon bonded to oxygen. 9 It is a cyclic, straight-chain, or branched alkyl radical having 1 to 20 carbon atoms or an aryl radical having 6 to 20 carbon atoms, wherein at least one hydrogen atom in the radical is optionally replaced by an alkyl group or functional group, or a halogen, C1-C4-haloalkyl, C1-C4-alkoxy, or C6-C 10 -Aryloxy, cyano, C1-C4-alkoxycarbonyl, C6-C 10 -Aryloxycarbonyl or aliphatic or aromatic C1-C 10 -acyloxy group, or All R 9 All are hydrogen, except for R which is adjacent to the carbon indirectly bonded to M. 9 It is a cyclic, straight-chain, or branched alkyl radical having 1 to 20 carbon atoms or an aryl radical having 6 to 20 carbon atoms, wherein at least one hydrogen atom in the radical is optionally replaced by an alkyl group or functional group, or a halogen, C1-C4-haloalkyl, C1-C4-alkoxy, or C6-C 10 -Aryloxy, cyano, C1-C4-alkoxycarbonyl, C6-C 10-Aryloxycarbonyl or aliphatic or aromatic C1-C 10 -acyloxy group, or All R 9 All are hydrogen, except for R, which is bonded to the second carbon from the carbon adjacent to the carbon indirectly bonded to M. 9 It is a cyclic, straight-chain, or branched alkyl radical having 1 to 20 carbon atoms or an aryl radical having 6 to 20 carbon atoms, wherein at least one hydrogen atom in the radical is optionally replaced by an alkyl group or functional group, or a halogen, C1-C4-haloalkyl, C1-C4-alkoxy, or C6-C 10 -Aryloxy, cyano, C1-C4-alkoxycarbonyl, C6-C 10 -Aryloxycarbonyl or aliphatic or aromatic C1-C 10 -acyloxy group, or All R 9 All are hydrogen, except for R, which is bonded to the second carbon from the carbon bonded to oxygen. 9 It is a cyclic, straight-chain, or branched alkyl radical having 1 to 20 carbon atoms or an aryl radical having 6 to 20 carbon atoms, wherein at least one hydrogen atom in the radical is optionally replaced by an alkyl group or functional group, or a halogen, C1-C4-haloalkyl, C1-C4-alkoxy, or C6-C 10 -Aryloxy, cyano, C1-C4-alkoxycarbonyl, C6-C 10 -Aryloxycarbonyl or aliphatic or aromatic C1-C 10- Acyloxy group, or The R on the carbon atom adjacent to the carbon atom of the five-membered ring 9 Each is a hydrogen radical or an aryl radical having 6 to 20 carbon atoms, wherein at least one hydrogen atom of the aryl radical is optionally replaced by an alkyl group or functional group, or each is a halogen, C1-C4-haloalkyl, C1-C4-alkoxy, or C6-C 10 -Aryloxy, cyano, C1-C4-alkoxycarbonyl, C6-C 10- Aryloxycarbonyl or aliphatic or aromatic C1-C 10 -acyloxy group, and the other two R groups 9 It is part of a cyclic aromatic system having 4 to 14 carbon atoms, wherein at least one hydrogen atom is optionally replaced by an alkyl group or a functional group, or The two R atoms on the carbon closest to the oxygen atom in the five-membered ring 9 The same or different aryl radicals, each being hydrogen or having 6 to 20 carbon atoms, wherein at least one hydrogen atom in the aryl radical is optionally replaced by an alkyl group or functional group, or each is a halogen, C1-C4-haloalkyl, C1-C4-alkoxy, C6-C 10 -Aryloxy, cyano, C1-C4-alkoxycarbonyl, C6-C10 -Aryloxycarbonyl or aliphatic or aromatic C1-C 10 -acyloxy group, and the two R groups on the carbon nearest to the oxygen atom bonded to the five-membered ring. 9 It is part of a cyclic aromatic system having 4 to 14 carbon atoms, wherein at least one hydrogen atom is optionally replaced by an alkyl group or a functional group. R 10 It is a straight-chain or branched alkyl radical having 1 to 20 carbon atoms, and when R 5 When it is also methyl, the R not bonded to the carbon atom bonded to the carbon atom on the five-membered ring. 9 It may not be part of a cyclic aromatic system with 4 carbon atoms.

[0068] 25. The method according to implementation scheme 24, wherein: M is ruthenium. X and X' are identical and each is a halide. R 9 Each of them is a hydrogen atom, except for the R atoms bonded to the carbon atom bonded to the oxygen atom. 9 It is a phenyl radical or naphthyl radical, wherein at least one hydrogen atom is optionally replaced by an alkyl group or functional group, or a radical derived from the group consisting of F, Cl, Br, trifluoromethyl, methoxy, ethoxy, isopropoxy, tert-butoxy, phenoxy, cyano, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, acetoxy, propionyloxy, and neopentyloxy, or... All R 9 All are hydrogen, except for R, which is bonded to the second carbon from the carbon bonded to oxygen on the five-membered ring. 9 It is a free radical derived from the group consisting of F, Cl, Br, trifluoromethyl, methoxy, ethoxy, isopropoxy, tert-butoxy, phenoxy, cyano, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, acetoxy, propionyloxy, and neopentyloxy, or... All R 9 All are hydrogen, except for R, which is bonded to the second carbon from the carbon not bonded to oxygen on the five-membered ring. 9 It is a free radical derived from the group consisting of F, Cl, Br, trifluoromethyl, methoxy, ethoxy, isopropoxy, tert-butoxy, phenoxy, cyano, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, acetoxy, propionyloxy, and neopentyloxy, or... All R 9 All are hydrogen, except for R, which is bonded to carbons adjacent to carbons on the five-membered ring that are not bonded to oxygen. 9It is a free radical derived from the group consisting of F, Cl, Br, trifluoromethyl, methoxy, ethoxy, isopropoxy, tert-butoxy, phenoxy, cyano, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, acetoxy, propionyloxy, and neopentyloxy, or... R bonded to the carbon adjacent to the carbon that is not bonded to oxygen on the five-membered ring 9 It is a free radical derived from hydrogen or from the group consisting of F, Cl, Br, trifluoromethyl, methoxy, ethoxy, isopropoxy, tert-butoxy, phenoxy, cyano, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, acetoxy, propionyloxy, and neopentyloxy, and is bonded to a carbon adjacent to the carbon bonded to oxygen on the five-membered ring. 9 It is a hydrogen, phenyl, or naphthyl group, with at least one hydrogen atom optionally replaced by an alkyl group or functional group, or a radical from the group consisting of F, Cl, Br, trifluoromethyl, methoxy, ethoxy, isopropoxy, tert-butoxy, phenoxy, cyano, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, acetoxy, propionyloxy, and neopentyloxy, and the other two R groups are not present. 9 It is part of a cyclic aromatic system having 4 to 8 carbon atoms, and at least one hydrogen atom is optionally replaced by an alkyl group or a functional group, or... R bonded to the carbon adjacent to the carbon that is not bonded to oxygen on the five-membered ring 9 It is a free radical derived from hydrogen or from the group consisting of F, Cl, Br, trifluoromethyl, methoxy, ethoxy, isopropoxy, tert-butoxy, phenoxy, cyano, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, acetoxy, propionyloxy, and neopentyloxy, and is bonded to the second carbon atom on the five-membered ring not bonded to oxygen. 9 It is a hydrogen, phenyl, or naphthyl group, with at least one hydrogen atom optionally replaced by an alkyl group or functional group, or a radical from the group consisting of F, Cl, Br, trifluoromethyl, methoxy, ethoxy, isopropoxy, tert-butoxy, phenoxy, cyano, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, acetoxy, propionyloxy, and neopentyloxy, and the other two R groups are not present. 9 It is part of a cyclic aromatic system having 4 to 8 carbon atoms, and at least one hydrogen atom is optionally replaced by an alkyl group or functional group. R 10 It is a branched alkyl group derived from the group consisting of isopropyl, isobutyl, sec-butyl, tert-butyl, branched pentyl, and branched hexyl, and, L is phosphine, and its formula is PR. 6 R 7 R 8 , where R 6 R 7 and R 8 Each is independently aryl, C1-C 10Alkyl or cycloalkyl.

[0069] 26. The method according to implementation scheme 25, wherein R 6 R 7 and R 8 Each time it appears, it is independently methyl, ethyl, cyclopentyl, cyclohexyl or phenyl.

[0070] 27. The method according to any one of embodiments 17 to 26, wherein the method is performed at a temperature greater than 0°C to about 60°C or about 20°C to about 50°C.

[0071] 28. The method according to any one of embodiments 17 to 27, wherein the metathesis catalyst is present in an amount of about 10 ppm to about 1000 ppm, about 50 ppm to about 500 ppm, or about 100 ppm to about 300 ppm.

[0072] 29. The method according to any one of embodiments 17 to 28, wherein the method is carried out in the absence of oxygen.

[0073] 30. The method according to any one of embodiments 17 to 29, wherein the formed conjugated diene polymer comprises vinylidene aromatic monomer polymer chains disposed between conjugated diene polymer chains.

[0074] 31. The method according to any one of embodiments 17 to 30, wherein the starting conjugated diene polymer is in particulate form, said particulate being grafted with polymer chains of one or more vinylidene aromatic monomers.

[0075] 32. The method according to embodiment 31, wherein the particles of the conjugated diene polymer are native particles of the conjugated diene polymer, the native particles being grafted with polymer chains of one or more vinylidene aromatic monomers.

[0076] 33. The method according to embodiment 32, wherein the particles of the conjugated diene polymer are recycled particles of the conjugated diene polymer.

[0077] 34. The method according to any one of embodiments 17 to 33, wherein a portion of the conjugated diene polymer has a polymer chain of one or more vinylidene aromatic monomers grafted onto the main chain of the polymer chain of the conjugated diene polymer.

[0078] 35. The method according to any one of embodiments 17 to 34, wherein the polymer chain of the one or more vinylidene aromatic monomers comprises one or more styrene-based monomers.

[0079] 36. The method according to any one of embodiments 17 to 34, wherein the polymer chain of the one or more vinylidene aromatic monomers comprises one or more styrene-based monomers and one or more monomers capable of polymerizing with the one or more styrene-based monomers.

[0080] 37. The method according to embodiment 36, wherein the polymer chain comprising one or more vinylidene aromatic monomers comprises one or more styrene-based monomers and acrylonitrile.

[0081] 38. The method according to any one of embodiments 17 to 37, wherein the prepared conjugated diene polymer has a polymer chain with one or more vinylidene aromatic monomers grafted onto its main chain.

[0082] 39. The method according to any one of embodiments 17 to 37, wherein the prepared conjugated diene polymer contains polymer chains of one or more vinylidene aromatic monomers, said polymer chains containing one or more styrene-based monomers.

[0083] 40. The method according to any one of embodiments 17 to 37, wherein the prepared conjugated diene polymer contains a polymer chain of one or more vinylidene aromatic monomers, said polymer chain comprising one or more styrene-based monomers and one or more monomers capable of polymerizing with said one or more styrene-based monomers.

[0084] 41. The method according to embodiment 38 or 39, wherein the prepared conjugated diene polymer contains a polymer chain of one or more vinylidene aromatic monomers, said polymer chain comprising one or more styrene-based monomers and acrylonitrile.

[0085] 42. The method according to any one of embodiments 17 to 41, wherein the conjugated diene polymer comprises polyisoprene or polybutadiene.

[0086] 43. The method according to any one of embodiments 17 to 42, wherein the formed conjugated diene polymer is dissolved in an organic solvent.

[0087] 44. The method according to any one of embodiments 17 to 43, wherein the organic solvent comprises one or more of aromatic hydrocarbons, aliphatic hydrocarbons, and ketones.

[0088] 45. The method according to any one of embodiments 17 to 43, wherein the organic solvent comprises one or more aromatic hydrocarbons.

[0089] 46. ​​A composition comprising: i) a polymer prepared from one or more vinylidene aromatic monomers; ii) particles comprising one or more conjugated diene polymers; and iii) the composition according to any one of embodiments 1 to 16.

[0090] 47. A method for compatibilizing i) a polymer prepared from one or more vinylidene aromatic monomers and ii) particles comprising one or more conjugated diene polymers, said method being by contacting i) and ii) with a composition according to any one of embodiments 1 to 16.

[0091] Illustrative Examples The following examples are provided only to illustrate the invention and are not intended to limit its scope. Unless otherwise stated, all parts and percentages are by weight.

[0092] Catalyst 1 Catalyst 2 Polybutadiene 1: Uncrosslinked or ungrafted polybutadiene rubber.

[0093] Polybutadiene 2 is composed of styrene acrylonitrile and a grafted rubber concentrate of grafted and crosslinked rubber, wherein the grafted rubber concentrate contains 50 wt% polybutadiene.

[0094] Example 1 A reaction mixture was formed from ethylbenzene, styrene, and acrylonitrile in the amounts listed in Table 1. The mixture was dissolved in tetrahydrofuran at a concentration of 0.25 wt%, with 35 mg of solids in 10 mL. C949 Grubbs catalyst (catalyst 1) was added to the mixture in the amounts listed in Table 1. Polybutadiene 1 was mixed into tetrahydrofuran at a concentration of 5 wt%, 500 mg per 10 mL. The polybutadiene mixture was fed into the first mixture, and the resulting mixture was heated at 50 °C for 24 hours. A control mixture was formed and reacted without a catalyst. Samples of the product mixture were analyzed using gel permeation chromatography. Figure 3 It refers to the DAD (diode array detector) signal of each sample prepared without a catalyst. Figure 4 It is the RID (Refractive Index Detector) signal, which is the signal from each sample of polybutadiene without the catalyst. Figure 5 These are the DAD signals of three samples using the catalyst. Figure 6 These are the RID signals of three samples using a catalyst. The data shows that rubber decomposition does not occur without a catalyst. Figures 3 to 6 middle, Figure 6 This is the curve for a sample that does not contain acrylonitrile. Figure 7 Figure 1 shows the curve for a sample containing 10% acrylonitrile, and Figure 8 shows the curve for a sample containing 20% ​​acrylonitrile. The presence of acrylonitrile inhibits decomposition at 10% because there is almost no reaction, while at 20% there is no reaction. In a 0% acrylonitrile feed, when using high-impact polystyrene, the double bonds break and the styrene ends up at the chain ends where the double bonds break.

[0095] Table 1 quantity

[0096] The amounts in Table 1 are based on the composition in wt%.

[0097] Example 2 Polybutadiene 2 was dissolved in dichloromethane solvent at a concentration of 5 wt%. Catalyst 2 was added to the mixture at 0.003 wt%. The mixture was heated at 50°C for 50 minutes, and samples were taken periodically. The viscosity was measured using a rotating disk viscometer according to the following procedure. Figure 7 This is a graph showing the viscosity of the conjugated diene polymer in Example 2 during metathesis as a function of time. The graph shows that the viscosity initially increases as the grafted rubber concentrate dissolves, and then decreases as the Mw of the soluble grafted rubber concentrate decreases.

Claims

1. A composition comprising a conjugated diene polymer containing a conjugated diene polymer chain and a vinylidene aromatic monomer polymer chain, wherein the polymer is soluble in an organic solvent, wherein soluble means that at least 1 wt%, 5 wt%, or 10 wt% of the conjugated diene polymer dissolves in the organic solvent at about 25°C.

2. The composition of claim 1, comprising a conjugated diene polymer, wherein the polymer is soluble in an organic solvent, wherein soluble means that at least 1 wt%, 5 wt%, or 10 wt% of the conjugated diene polymer is soluble in the organic solvent at about 25°C.

3. The composition according to claim 1 or 2, wherein the vinylidene aromatic monomer polymer chains are located between conjugated diene polymer chains.

4. The composition according to any one of the preceding claims, comprising a polymer chain consisting of one or more vinylidene aromatic monomers.

5. The composition according to any one of the preceding claims, comprising one or more vinylidene aromatic monomers and a polymer chain of one or more monomers capable of polymerizing with said one or more vinylidene aromatic monomers.

6. The composition according to any one of the preceding claims, wherein the polymer chain of the one or more vinylidene aromatic monomers comprises one or more vinylidene aromatic monomers and one or more monomers capable of polymerizing the vinylidene aromatic monomers, the one or more monomers comprising one or more of unsaturated nitrile, (meth)acrylic acid, maleic anhydride and maleimide.

7. The composition according to any one of the preceding claims, comprising one or more vinylidene aromatic monomers and one or more unsaturated nitrile polymer chains.

8. The composition according to any one of the preceding claims, comprising a polymer chain comprising styrene and acrylonitrile.

9. The composition according to any one of the preceding claims, wherein the conjugated diene polymer chain comprises isoprene or butadiene.

10. The composition according to any one of the preceding claims, wherein the conjugated diene polymer is dissolved in an organic solvent.

11. The composition according to any one of the preceding claims, wherein the conjugated diene polymer is dissolved in an organic solvent comprising one or more aromatic hydrocarbons, aliphatic hydrocarbons, and ketones.

12. The composition according to any one of the preceding claims, wherein the conjugated diene polymer is dissolved in an organic solvent comprising one or more aromatic hydrocarbons.

13. The composition according to any one of the preceding claims, wherein the conjugated diene comprises butadiene, the vinylidene aromatic monomer comprises one or more styrene-based monomers, and the one or more monomers polymerizable with the one or more vinylidene aromatic monomers comprise one or more unsaturated nitrile monomers.

14. The composition according to any one of the preceding claims, wherein the conjugated diene comprises butadiene, the vinylidene aromatic monomer comprises styrene, and the one or more monomers capable of polymerizing with the vinylidene aromatic monomer comprise acrylonitrile.

15. The composition according to any one of the preceding claims, comprising the conjugated diene polymer having grafted polymer chains prepared from one or more vinylidene aromatic monomers.

16. The composition according to any one of the preceding claims, comprising the conjugated diene polymer blended with a polymer comprising a vinylidene aromatic monomer.

17. A method comprising: Under conditions that cause partial double bond breakage in a conjugated diene polymer containing conjugated diene polymer chains and vinylidene aromatic monomer polymer chains, the conjugated diene polymer is contacted with a metathesis catalyst in an organic solvent, thereby preparing a conjugated diene polymer containing conjugated diene polymer chains and vinylidene aromatic monomer polymer chains, wherein the conjugated diene polymer is soluble in the organic solvent, wherein soluble means that at least 1 wt%, 5 wt%, or 10 wt% of the conjugated diene polymer dissolves in the organic solvent at about 25°C.

18. The method of claim 17, wherein the metathesis catalyst comprises a transition metal carbene.

19. The method according to claim 17 or 18, wherein the metathesis catalyst comprises a transition metal carbene, the transition metal carbene corresponding to the formula... ;in: M is a transition metal in group 8 of the periodic table; X and X 1 Each is an anionic ligand independently; L is a neutral electron donor ligand; and... R and R 1 Each is independently hydrogen or a substituent selected from the group consisting of: C1-C 20 Alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl, aryl, Cι-C 20 Carboxylic acid ester group, C1-C 20 Alkoxy, C2-C 20 alkenyloxy group, C2-C 20 alkynyloxy group, aryloxy group, C2-C 20 Alkoxycarbonyl, C1-C 20 Alkyl thiols, aryl thiols, C1-C 20 alkylsulfonyl and C1-C 20 alkylsulfinyl group, wherein the substituent is optionally replaced by one or more portions selected from the group consisting of: C1-C 10 Alkyl, C1-C 10 Alkoxy, aryl, and functional groups selected from the group consisting of: hydroxyl, thiol, thioether, ketone, aldehyde, ester, ether, amine, imine, amide, nitro, carboxylic acid, disulfide, carbonate, isocyanate, carbodiimide, alkoxycarbonyl, carbamate, and halogen.

20. The method according to any one of claims 17 to 19, wherein the metathesis catalyst comprises a transition metal carbene, the transition metal carbene corresponding to the structure in: M is a transition metal in group 8 of the periodic table; X and X 1 Each is an anionic ligand independently; L is a neutral electron donor ligand; and R, R 1 R 2 R 3 R 4 and R 5 Each is independently hydrogen or a substituent selected from the group consisting of: C1-C 20 Alkyl, C2-C 20 alkenyl, C2-C 20 alkynyl, aryl, C1-C 20 Carboxylic acid ester group, C1-C 20 Alkoxy, C2-C 20 alkenyloxy group, C2-C 20 alkynyloxy group, aryloxy group, C2-C 20 alkoxycarbonyl, C1-C 20 Alkyl thiols, aryl thiols, C1-C 20 alkylsulfonyl and C1-C 20 alkylsulfinyl group, wherein the substituent is optionally replaced by one or more portions selected from the group consisting of: C1-C 10 Alkyl, C1-C 10 Alkoxy, aryl, and functional groups selected from the group consisting of: hydroxyl, thiol, thioether, ketone, aldehyde, ester, ether, amine, imine, amide, nitro, carboxylic acid, disulfide, carbonate, isocyanate, carbodiimide, alkoxycarbonyl, carbamate, and halogen.

21. The method of claim 20, wherein: M is either ruthenium or osmium; L and L are each independently selected from the group consisting of: phosphine, sulfonated phosphite group, hypophosphite group, phosphite group, arsine, antimony, ether, amine, amide, imine, sulfoxide, carboxyl group, nitrosyl group, pyridine, and thioether; and, X and X 1 Each substituent is independently hydrogen, a halide, or selected from the group consisting of: C1-C 20 Alkyl, aryl, C1-C 20 Alkyl oxides, aromatic oxides, C3-C 20 Alkyl diketoester group, aryl diketoester group, C1-C 20 Carboxylic acid ester group, aryl sulfonate group, C1-C 20 Alkyl sulfonate group, C1-C 20 Alkyl thiols, aryl thiols, C1-C 20 alkylsulfonyl and C1-C 20 alkylsulfinyl group, wherein the substituent is optionally partially substituted by one or more groups selected from the group consisting of: C 1-10 Alkyl, C1-C 10 Alkoxy, aryl, and halogenated compounds.

22. The method of claim 20, wherein: M is ruthenium; X and X 1 Each of the following groups is independently selected: halides, CF3CO2, CH3CO2, CFH2CO2, (CH3)3CO, (CF3)2(CH3)CO, (CF3)(CH3)2CO, PhO, MeO, EtO, toluenesulfonates, methanesulfonates and trifluoromethanesulfonates; L is the formula PR 6 R 7 R 8 Phosphine, of which R 6 R 7 and R 8 Each is independently aryl, C1-C 10 Alkyl or cycloalkyl; R is hydrogen; and, R 1 It is phenyl or vinyl, optionally substituted with one or more portions selected from the group consisting of: C1-C5 alkyl, C1-C5 alkoxy, phenyl, and functional groups selected from the group consisting of: hydroxyl, thiol, thioether, ketone, aldehyde, ester, ether, amine, imine, amide, nitro, carboxylic acid, disulfide, carbonate, isocyanate, carbodiimide, alkoxycarbonyl, carbamate, and halogen.

23. The method according to claim 17 or 18, wherein the metathesis catalyst comprises a transition metal carbene, the transition metal carbene corresponding to the formula... ； M is a transition metal in group 8 of the periodic table; X and X' are the same or different and are each anionic ligands; R 9 Each time it appears, it is independently hydrogen, provided that there is at least one free radical R. 9 Unlike hydrogen, or each being a cyclic, straight-chain, or branched alkyl radical having 1 to 50 carbon atoms or an aryl radical having 6 to 30 carbon atoms, wherein at least one hydrogen atom is optionally replaced by an alkyl group or functional group, and at least one R 9 It is a halogen, C1-C4-haloalkyl, C1-C4-alkoxy, C6-C 10 -Aryloxy, cyano, C1-C4-alkoxy-carbonyl, C6-C 10 -Aryloxycarbonyl or aliphatic or aromatic C1-C 10 -acyloxy group; and / or Two adjacent R 9 It may be part of a cyclic system consisting of a carbon skeleton having 3 to 20 carbon atoms, excluding the carbon atoms in formula (I), wherein at least one hydrogen atom is optionally replaced by an alkyl group or functional group, and / or at least one carbon atom of the ring is optionally replaced by a heteroatom from the group consisting of S, P, O and N; and R 10 It is a hydrogen radical or a cyclic, straight-chain or branched alkyl radical having 1 to 20 carbon atoms, or an aryl radical having 6 to 20 carbon atoms, wherein at least one hydrogen atom in the radical is optionally replaced by an alkyl group or functional group, and when R 10 When it is also a methyl group, the R opposite to the five-membered ring... 9 It may not be part of a cyclic aromatic system having four carbon atoms, does not include the carbon atoms, and, L is a neutral two-electron donor; derived from the group consisting of amines, imines, phosphines, phosphites, antimony, arsine, CO, carbonyl compounds, nitriles, alcohols, thiols, ethers, and thioethers.

24. The method according to claim 23, wherein: M is either ruthenium or osmium. X and X' may be the same or different and are each anionic ligands derived from halides, pseudohalides, hydroxides, alkoxides, carboxylic acid esters, and sulfonates; R 9 It is hydrogen independently each time it appears, provided that at least one R is present. 9 Unlike hydrogen, or each being a cyclic, straight-chain, or branched alkyl radical having 1 to 20 carbon atoms or an aryl radical having 6 to 20 carbon atoms, wherein at least one hydrogen atom in the alkyl radical and aryl radical is optionally replaced by a functional group, and at least one R 9 It is a halogen, C1-C4-haloalkyl, C1-C4-alkoxy, C6-C 10 -Aryloxy, cyano, C1-C4-alkoxycarbonyl, C6-C 10 -Aryloxycarbonyl or aliphatic or aromatic C1-C 10 -acyloxy group, or All R 9 All are hydrogen, except for R, which is adjacent to the carbon bonded to oxygen. 9 It is a cyclic, straight-chain, or branched alkyl radical having 1 to 20 carbon atoms or an aryl radical having 6 to 20 carbon atoms, wherein at least one hydrogen atom in the radical is optionally replaced by an alkyl group or functional group, or a halogen, C1-C4-haloalkyl, C1-C4-alkoxy, or C6-C 10 -Aryloxy, cyano, C1-C4-alkoxycarbonyl, C6-C 10 -Aryloxycarbonyl or aliphatic or aromatic C1-C 10 -acyloxy group, or All R 9 All are hydrogen, except for R which is adjacent to the carbon indirectly bonded to M. 9 It is a cyclic, straight-chain, or branched alkyl radical having 1 to 20 carbon atoms or an aryl radical having 6 to 20 carbon atoms, wherein at least one hydrogen atom in the radical is optionally replaced by an alkyl group or functional group, or a halogen, C1-C4-haloalkyl, C1-C4-alkoxy, or C6-C 10 -Aryloxy, cyano, C1-C4-alkoxycarbonyl, C6-C 10 -Aryloxycarbonyl or aliphatic or aromatic C1-C 10 -acyloxy group, or All R 9 All are hydrogen, except for R, which is bonded to the second carbon from the carbon adjacent to the carbon indirectly bonded to M. 9 It is a cyclic, straight-chain, or branched alkyl radical having 1 to 20 carbon atoms or an aryl radical having 6 to 20 carbon atoms, wherein at least one hydrogen atom in the radical is optionally replaced by an alkyl group or functional group, or a halogen, C1-C4-haloalkyl, C1-C4-alkoxy, or C6-C 10 -Aryloxy, cyano, C1-C4-alkoxycarbonyl, C6-C 10 -Aryloxycarbonyl or aliphatic or aromatic C1-C 10 -acyloxy group, or All R 9 All are hydrogen, except for R, which is bonded to the second carbon from the carbon bonded to oxygen. 9 It is a cyclic, straight-chain, or branched alkyl radical having 1 to 20 carbon atoms or an aryl radical having 6 to 20 carbon atoms, wherein at least one hydrogen atom in the radical is optionally replaced by an alkyl group or functional group, or a halogen, C1-C4-haloalkyl, C1-C4-alkoxy, or C6-C 10 -Aryloxy, cyano, C1-C4-alkoxycarbonyl, C6-C 10 -Aryloxycarbonyl or aliphatic or aromatic C1-C 10- Acyloxy group, or The R on the carbon atom adjacent to the carbon atom of the five-membered ring 9 Each is a hydrogen radical or an aryl radical having 6 to 20 carbon atoms, wherein at least one hydrogen atom of the aryl radical is optionally replaced by an alkyl group or functional group, or each is a halogen, C1-C4-haloalkyl, C1-C4-alkoxy, or C6-C 10 -Aryloxy, cyano, C1-C4-alkoxycarbonyl, C6-C 10- Aryloxycarbonyl or aliphatic or aromatic C1-C 10 -acyloxy group, and the other two R groups 9 It is part of a cyclic aromatic system having 4 to 14 carbon atoms, wherein at least one hydrogen atom is optionally replaced by an alkyl group or a functional group, or The two R atoms on the carbon closest to the oxygen atom in the five-membered ring 9 The same or different aryl radicals, each being hydrogen or having 6 to 20 carbon atoms, wherein at least one hydrogen atom in the aryl radical is optionally replaced by an alkyl group or functional group, or each is a halogen, C1-C4-haloalkyl, C1-C4-alkoxy, C6-C 10 -Aryloxy, cyano, C1-C4-alkoxycarbonyl, C6-C 10 -Aryloxycarbonyl or aliphatic or aromatic C1-C 10 -acyloxy group, and the two R groups on the carbon nearest to the oxygen atom bonded to the five-membered ring. 9 It is part of a cyclic aromatic system having 4 to 14 carbon atoms, wherein at least one hydrogen atom is optionally replaced by an alkyl group or a functional group. R 10 It is a straight-chain or branched alkyl radical having 1 to 20 carbon atoms, and when R 5 When it is also methyl, the R not bonded to the carbon atom bonded to the carbon atom on the five-membered ring. 9 It may not be part of a cyclic aromatic system with 4 carbon atoms.

25. The method of claim 24, wherein: M is ruthenium. X and X' are identical and each is a halide. R 9 Each of them is a hydrogen atom, except for R, which is bonded to a carbon atom bonded to an oxygen atom. 9 It is a phenyl radical or naphthyl radical, wherein at least one hydrogen atom is optionally replaced by an alkyl group or functional group, or a radical derived from the group consisting of F, Cl, Br, trifluoromethyl, methoxy, ethoxy, isopropoxy, tert-butoxy, phenoxy, cyano, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, acetoxy, propionyloxy, and neopentyloxy, or... All R 9 All are hydrogen, except for R, which is bonded to the second carbon from the carbon bonded to oxygen on the five-membered ring. 9 It is a free radical derived from the group consisting of F, Cl, Br, trifluoromethyl, methoxy, ethoxy, isopropoxy, tert-butoxy, phenoxy, cyano, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, acetoxy, propionyloxy, and neopentyloxy, or... All R 9 All are hydrogen, except for R, which is bonded to the second carbon from the carbon not bonded to oxygen on the five-membered ring. 9 It is a free radical derived from the group consisting of F, Cl, Br, trifluoromethyl, methoxy, ethoxy, isopropoxy, tert-butoxy, phenoxy, cyano, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, acetoxy, propionyloxy, and neopentyloxy, or... All R 9 All are hydrogen, except for R, which is bonded to carbons adjacent to carbons on the five-membered ring that are not bonded to oxygen. 9 It is a free radical derived from the group consisting of F, Cl, Br, trifluoromethyl, methoxy, ethoxy, isopropoxy, tert-butoxy, phenoxy, cyano, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, acetoxy, propionyloxy, and neopentyloxy, or... R bonded to the carbon adjacent to the carbon that is not bonded to oxygen on the five-membered ring 9 It is a free radical derived from hydrogen or from the group consisting of F, Cl, Br, trifluoromethyl, methoxy, ethoxy, isopropoxy, tert-butoxy, phenoxy, cyano, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, acetoxy, propionyloxy, and neopentyloxy, and is bonded to a carbon adjacent to the carbon bonded to oxygen on the five-membered ring. 9 It is a hydrogen, phenyl, or naphthyl group, with at least one hydrogen atom optionally replaced by an alkyl group or functional group, or a radical from the group consisting of F, Cl, Br, trifluoromethyl, methoxy, ethoxy, isopropoxy, tert-butoxy, phenoxy, cyano, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, acetoxy, propionyloxy, and neopentyloxy, and the other two R groups are not present. 9 It is part of a cyclic aromatic system having 4 to 8 carbon atoms, and at least one hydrogen atom is optionally replaced by an alkyl group or a functional group, or... R bonded to the carbon adjacent to the carbon that is not bonded to oxygen on the five-membered ring 9 It is a free radical derived from hydrogen or from the group consisting of F, Cl, Br, trifluoromethyl, methoxy, ethoxy, isopropoxy, tert-butoxy, phenoxy, cyano, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, acetoxy, propionyloxy, and neopentyloxy, and is bonded to the second carbon atom on the five-membered ring not bonded to oxygen. 9 It is a hydrogen, phenyl, or naphthyl group, with at least one hydrogen atom optionally replaced by an alkyl group or functional group, or a radical from the group consisting of F, Cl, Br, trifluoromethyl, methoxy, ethoxy, isopropoxy, tert-butoxy, phenoxy, cyano, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, acetoxy, propionyloxy, and neopentyloxy, and the other two R groups are not present. 9 It is part of a cyclic aromatic system having 4 to 8 carbon atoms, and at least one hydrogen atom is optionally replaced by an alkyl group or functional group. R 10 It is a branched alkyl group derived from the group consisting of isopropyl, isobutyl, sec-butyl, tert-butyl, branched pentyl, and branched hexyl, and, L is phosphine, and its formula is PR. 6 R 7 R 8 , where R 6 R 7 and R 8 Each is independently aryl, C1-C 10 Alkyl or cycloalkyl.

26. The method of claim 25, wherein R 6 R 7 and R 8 Each time it appears, it is independently methyl, ethyl, cyclopentyl, cyclohexyl or phenyl.

27. The method according to any one of claims 17 to 26, wherein the method is performed at a temperature greater than 0°C to about 60°C or about 20°C to about 50°C.

28. The method according to any one of claims 17 to 27, wherein the metathesis catalyst is present in an amount of about 10 ppm to about 1000 ppm, about 50 ppm to about 500 ppm, or about 100 ppm to about 300 ppm.

29. The method according to any one of claims 17 to 28, wherein the method is carried out in the absence of oxygen.

30. The method according to any one of claims 17 to 29, wherein the formed conjugated diene polymer comprises vinylidene aromatic monomer polymer chains disposed between conjugated diene polymer chains.

31. The method according to any one of claims 17 to 30, wherein the starting conjugated diene polymer is in particulate form, said particulate being grafted with polymer chains of one or more vinylidene aromatic monomers.

32. The method of claim 31, wherein the particles of the conjugated diene polymer are native particles of the conjugated diene polymer, the native particles being grafted with polymer chains of one or more vinylidene aromatic monomers.

33. The method of claim 32, wherein the particles of the conjugated diene polymer are recycled particles of the conjugated diene polymer.

34. The method according to any one of claims 17 to 33, wherein a portion of the conjugated diene polymer has a polymer chain of one or more vinylidene aromatic monomers grafted onto the main chain of the polymer chain of the conjugated diene polymer.

35. The method according to any one of claims 17 to 34, wherein the polymer chain of the one or more vinylidene aromatic monomers comprises one or more styrene-based monomers.

36. The method according to any one of claims 17 to 34, wherein the polymer chain of the one or more vinylidene aromatic monomers comprises one or more styrene-based monomers and one or more monomers capable of polymerizing with the one or more styrene-based monomers.

37. The method of claim 36, wherein the polymer chain comprising one or more vinylidene aromatic monomers comprises one or more styrene-based monomers and acrylonitrile.

38. The method according to any one of claims 17 to 37, wherein the prepared conjugated diene polymer has polymer chains grafted to one or more vinylidene aromatic monomers on its main chain.

39. The method according to any one of claims 17 to 37, wherein the prepared conjugated diene polymer contains polymer chains of one or more vinylidene aromatic monomers, said polymer chains containing one or more styrene-based monomers.

40. The method according to any one of claims 17 to 37, wherein the prepared conjugated diene polymer contains a polymer chain of one or more vinylidene aromatic monomers, said polymer chain comprising one or more styrene-based monomers and one or more monomers capable of polymerizing with said one or more styrene-based monomers.

41. The method of claim 38 or 39, wherein the prepared conjugated diene polymer comprises a polymer chain of one or more vinylidene aromatic monomers, said polymer chain comprising one or more styrene-based monomers and acrylonitrile.

42. The method according to any one of claims 17 to 41, wherein the conjugated diene polymer comprises polyisoprene or polybutadiene.

43. The method according to any one of claims 17 to 42, wherein the formed conjugated diene polymer is dissolved in an organic solvent.

44. The method according to any one of claims 17 to 43, wherein the organic solvent comprises one or more of aromatic hydrocarbons, aliphatic hydrocarbons, and ketones.

45. The method according to any one of claims 17 to 43, wherein the organic solvent comprises one or more aromatic hydrocarbons.

46. ​​A composition comprising: i) a polymer prepared from one or more vinylidene aromatic monomers; ii) particles comprising one or more conjugated diene polymers; and iii) the composition according to any one of claims 1 to 16.

47. A method for compatibilizing i) a polymer prepared from one or more vinylidene aromatic monomers and ii) particles comprising one or more conjugated diene polymers, said method being by contacting i) and ii) with a composition according to any one of claims 1 to 16.

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