WO2024115988A1 - Composition de caoutchouc respectueuse de l'environnement - Google Patents

Composition de caoutchouc respectueuse de l'environnement Download PDF

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Publication number
WO2024115988A1
WO2024115988A1 PCT/IB2023/061166 IB2023061166W WO2024115988A1 WO 2024115988 A1 WO2024115988 A1 WO 2024115988A1 IB 2023061166 W IB2023061166 W IB 2023061166W WO 2024115988 A1 WO2024115988 A1 WO 2024115988A1
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WO
WIPO (PCT)
Prior art keywords
cross
rubber
rubber composition
phr
castor oil
Prior art date
Application number
PCT/IB2023/061166
Other languages
English (en)
Inventor
Ramakrishnan Subramanian
Pulikaparambil Kochaidrew Mohamed
Indranil Dey
Rohit Ameta
Original Assignee
Apollo Tyres Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Apollo Tyres Ltd. filed Critical Apollo Tyres Ltd.
Publication of WO2024115988A1 publication Critical patent/WO2024115988A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
    • C08L9/06—Copolymers with styrene
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
    • B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
    • B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
    • B60C1/0016—Compositions of the tread
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/101—Esters; Ether-esters of monocarboxylic acids
    • C08K5/103—Esters; Ether-esters of monocarboxylic acids with polyalcohols

Definitions

  • the present disclosure relates to environment-friendly rubber compositions intended in particular for the manufacture of tires or tire components, such as tire treads.
  • Aromatic hydrocarbon oils obtained from petroleum refining have been known for a long time and are used as plasticizers or extender oils in natural and synthetic rubbers or rubber products. These petroleum-based hydrocarbon oils are used in the tire industry as processing aids to ease compounding of rubber and as plasticizers to modify the mechanical properties of rubber compound after vulcanization. They are also used to reduce Mooney viscosity of synthetic rubbers to ease their compounding with other ingredients of rubber formulations. Enormous amount of plasticizers is sometimes added to rubber mixtures, in order to reduce the cost of the mixture, to improve filler dispersion, and to improve the physical properties of the mixture and of the vulcanizates produced therefrom. Majority of the plasticizers used in the rubber industry are generally based on petroleum.
  • distillate aromatic extract (DAE) oils Most commonly used are distillate aromatic extract (DAE) oils, treated distillate aromatic extract (TDAE) oils, mild extract solvate (MES) oils and residual aromatic extract (RAE) oils.
  • DAE distillate aromatic extract
  • TDAE treated distillate aromatic extract
  • MES mild extract solvate
  • RAE residual aromatic extract
  • the use of petroleum-based hydrocarbon oils as rubber plasticizer is undesirable for environmental reasons due to the possible danger to the environment and inhabitants. Additionally, the use of petroleum-based hydrocarbon oils in the manufacture of tires or rubber products is expected to decline in the coming years because of the continuous rise in the price of crude oil and the high rate of depletion of known petroleum oil reserves.
  • Alternatives used as plasticizers in rubber formulations are vegetable oils. However, when utilizing vegetable oils as rubber plasticizer, their polarity becomes a problem due to the lack of compatibility between the non-polar rubbers and the polar vegetable oils.
  • aspects of the present disclosure relate to the use of maleated castor oil as plasticizer for rubber compositions usable for the manufacture of tires or tire components such as tire treads.
  • the bio-based maleated castor oil does not have the disadvantages of petroleum-based plasticizers and may be used to replace a part of the petroleum-based plasticizer or to replace it completely in cross -linkable or cross-linked rubber compositions specifically designed for tire applications.
  • the maleated castor oil has excellent compatibility with natural and synthetic rubbers of non-polar type, thereby allowing to plasticize a wide variety of non-polar rubbers usable in tire applications and to maximize the desired properties of final finished products.
  • one aspect of the present disclosure is directed to a cross -linkable rubber composition
  • a cross -linkable rubber composition comprising an elastomer, a filler, and a maleated castor oil.
  • Maleated castor oil is the product of chemical reaction of castor oil and maleic anhydride.
  • the maleated castor oil can be used in the cross-linkable rubber composition in an amount of from 1 to 20 phr. Preferably, the amount of maleated castor oil is between 7 and 20 phr.
  • the elastomer can be a natural rubber or a synthetic rubber usable for the manufacture of tires or tire components.
  • the elastomer can be a blend of two or more synthetic rubbers.
  • the elastomer is a blend of polybutadiene rubber (PBD) with solution-polymerized styrene-butadiene (SSBR).
  • PBD polybutadiene rubber
  • SSBR solution-polymerized styrene-
  • the cross-linkable rubber composition comprises a filler.
  • the filler can be selected from the group consisting of carbon black, silica, aluminosilicates, chalk, titanium dioxide, magnesium oxide, zinc oxide, clay, calcium carbonate, and a mixture thereof.
  • filler(s) are present in the cross -linkable rubber composition in an amount of from 30 to 90 phr.
  • the filler has a BET surface of between 150 and 250 m 2 /g.
  • the cross-linkable rubber composition can further include a vulcanization system to cause dynamic vulcanization (cross-linking) of the unvulcanised elastomers.
  • the vulcanization system can include at least one cross-linking agent, at least one vulcanization accelerator, at least one vulcanization activator, or a mixture thereof.
  • the vulcanization system is present in the cross-linkable rubber composition in an amount of from 0.5 to 20 phr.
  • the cross-linkable rubber composition comprises 100 phr of at least one elastomer, 30 to 90 phr of a filler, 1 to 20 phr of maleated castor oil, 0.5 to 5 phr of at least one cross-linking agent, 1 to 7 phr of at least one vulcanization accelerator, and 1 to 8 phr of at least one vulcanization activator.
  • cross-linked rubber composition obtained by cross-linking the cross-linkable rubber composition disclosed herein.
  • the cross-linked rubber composition can be obtained by blending the cross -linkable rubber composition with a vulcanization system to produce a blend, and heating the blend at a predetermined temperature to form the cross-linked rubber composition.
  • the blend is heated to a temperature from 110° C to 200° C.
  • Another aspect of the present disclosure relates to a tire or tire tread, comprising the cross-linked rubber composition disclosed herein.
  • Another aspect of the present disclosure relates to a finished or semifinished rubber article, comprising the cross-linked rubber composition disclosed herein.
  • FIG. 1 illustrates a reaction scheme for the preparation of maleated castor oil.
  • FIG. 2 shows a comparison of the FTIR spectrum of (unmodified) castor oil to the FTIR spectrum of maleated castor oil produced according to an embodiment of the present disclosure.
  • the numbers expressing quantities of ingredients, properties such as concentration, process conditions, and so forth, used to describe and claim certain embodiments of the invention are to be understood as being modified in some instances by the term “about.” Accordingly, in some embodiments, the numerical parameters set forth in the written description are approximations that can vary depending upon the desired properties sought to be obtained by a particular embodiment. In some embodiments, the numerical parameters should be construed in light of the number of reported significant digits and by applying ordinary rounding techniques. Notwithstanding that the numerical ranges and parameters setting forth the broad scope of some embodiments of the invention are approximations, the numerical values set forth in the specific examples are reported as precisely as practicable.
  • the term “phr” refers to parts by weight of the referenced component per 100 parts by weight of total rubber or elastomer in the composition. Such term is commonly used in the rubber compounding art.
  • the present disclosure is directed to the use of maleated castor oil as plasticizer for rubber compositions usable for the manufacture of tires or tire components such as tire treads.
  • the bio-based maleated castor oil does not have the disadvantages of petroleum-based plasticizers and may be used to replace a part of the petroleum-based plasticizer or to replace it completely in cross-linkable or cross-linked rubber compositions specifically designed for tire applications.
  • the maleated castor oil has excellent compatibility with natural and synthetic rubbers of non-polar type, thereby allowing to plasticize a wide variety of non-polar rubbers usable in tire applications and to maximize the desired properties of final finished products.
  • one aspect of the present disclosure is directed to a cross -linkable rubber composition
  • a cross -linkable rubber composition comprising an elastomer, a filler, and a maleated castor oil.
  • the crosslinkable rubber composition is useful for the manufacture of tires or tire components such as tire treads, and includes at least one elastomer.
  • the elastomer is a cross-linkable (curable), e.g., vulcanizable, elastomer.
  • the term "elastomer” is often used interchangeably with the term “rubber” or more professional "un-vulcanized rubber”.
  • the elastomer can be a natural rubber, a synthetic rubber, a blend of synthetic and natural rubber, or a blend of various synthetic rubbers.
  • the elastomer can be selected from the group consisting of natural rubber (NR), synthetic polyisoprene rubber (IR), polybutadiene rubber (PBD), polyvinyl-butadiene rubber, styrene -butadiene rubber (SBR), solution-polymerized styrenebutadiene rubber (SSBR), emulsion-polymerized styrene-butadiene rubber (ESBR), nitrile rubber (NBR), hydrogenated nitrile rubber, butyl rubber, halogenated butyl rubbers, liquid rubbers, polynorbornene copolymer, isoprene-isobutylene copolymer, chloroprene rubber, ethylene propylene diene monomer rubber (EPDM), acrylate rubber, fluorine rubber, silicone rubber, polysulfide rubber, epichlorohydrin rubber, a terpolymer formed from ethylene monomers, propylene monomers
  • the elastomer is a blend of polybutadiene rubber with a styrene-butadiene rubber.
  • the elastomer is a blend of polybutadiene rubber (PBD) with solution-polymerized styrene-butadiene (SSBR).
  • the cross-linkable rubber composition comprises from 10 to 40 phr of polybutadiene rubber as a blend with from 60 to 90 phr of a styrene-butadiene rubber.
  • the cross-linkable rubber composition comprises 20 phr of polybutadiene rubber as a blend with 80 phr of a styrene-butadiene rubber.
  • the cross-linkable rubber composition comprises maleated castor oil as plasticizer.
  • the maleated castor oil can be used to replace a part of the traditional petroleum-based plasticizer or to replace it completely in cross -linkable or cross-linked rubber compositions specifically designed for tire applications.
  • Maleated castor oil is the product of chemical reaction of castor oil and maleic anhydride.
  • maleated castor oil (MACO) can be prepared by an esterification reaction between castor oil (CO) and maleic anhydride (MAH) in presence of benzoyl peroxide as a catalyst. It is preferred that the molar ratio of castor oil to maleic anhydride ranges between about 1:1 and 1:3.
  • FIG. 1 depicts a reaction scheme for the preparation of maleated castor oil by reaction of castor oil with maleic anhydride.
  • FIG. 2 shows a comparison of the FTIR spectrum of (unmodified) castor oil to the FTIR spectrum of maleated castor oil produced according to an embodiment of the present disclosure.
  • the maleated castor oil according to the present disclosure has characteristic FTIR peaks at 3440 cm’ 1 and 1650 cm’ 1 , as determined using ASTM E1252.
  • the maleated castor oil associates with the filler surface and keeps the filler particles adequately and homogenously dispersed in rubber matrix until curing (cross -linking) takes place, thereby preventing flocculation of filler particles after rubber compounding.
  • the reactive C-C double bond of the maleated castor oil chemically bonds to the rubber molecules, which prevents the maleated castor oil from leaching out of the cured (vulcanized) rubber over time.
  • the maleated castor oil can be used in the cross -linkable rubber composition in an amount of from 1 to 20 phr. Preferably, the amount of maleated castor oil is between 7 and 20 phr.
  • the cross -linkable rubber composition includes a reinforcing filler to improve technical requirements of tires, such as high wear resistance, low rolling resistance, or wet grip.
  • a filler can be used as long as it is compatible with the elastomer
  • typical fillers include carbon black, silica, aluminosilicates, chalk, titanium dioxide, magnesium oxide, zinc oxide, clay, calcium carbonate, and a mixture thereof.
  • silica or carbon clack is used as the filler.
  • the filler is a blend of silica and carbon black.
  • Filler(s) are present in the cross-linkable rubber composition in an amount of from 30 to 90 phr, preferably from 50 to 90 phr.
  • the filler has a BET surface of between 150 and 250 m /g, as measured according to ASTM D6738.
  • the cross-linkable rubber composition can further include a vulcanization system to cause dynamic vulcanization (cross-linking) of the unvulcanised elastomers.
  • the vulcanization system can include at least one cross-linking agent, at least one vulcanization accelerator, at least one vulcanization activator, or a mixture thereof.
  • the vulcanization system is present in the cross-linkable rubber composition in an amount of from 0.5 to 20 phr.
  • cross-linking agent any cross-linking agent known in the art may be used, in preferred embodiments of the present disclosure, sulphur is used.
  • the amount of cross-linking agent is preferably between 0.5 and 5 phr.
  • vulcanization accelerators include but not limited to n-cyclohexyl-2-benzothiazole sulfenamide (CBS), diphenyl guanidine (DPG), and combination thereof.
  • CBS n-cyclohexyl-2-benzothiazole sulfenamide
  • DPG diphenyl guanidine
  • a mixture of CBS and DPG is used as the vulcanization accelerator.
  • the vulcanization accelerator can be used in an amount ranging from 1 to 7 phr.
  • the vulcanization activator can be any activator as would be known to one of skill in the art.
  • the activator is selected from zinc oxide, stearic acid, and a combination thereof.
  • a mixture of zinc oxide and stearic acid is used as the vulcanization activator.
  • the vulcanization activator can be used in an amount ranging from 1 to 8 phr.
  • the cross-linkable rubber composition of the present disclosure may also include any suitable additives generally used in tire rubber compositions.
  • the cross-linkable rubber composition includes one or more additives from the group consisting of coupling agents, antioxidants, antiozonants, stabilizers, masticating agents, adhesion promoters, colorants, homogenizers, dispersion agents, and vulcanization retarders.
  • the cross -linkable rubber composition further comprises at least one antioxidant. While any antioxidants may be used, typical antioxidants include but not limited to n-phenyl-N'-(l,3-dimethylbutyl)-p-phenylenediamine (6-PPD), 1,2-dihydro- 2,2,4-trimethyl-quinoline (TMQ), and combination thereof. Antioxidant(s) can be used in the cross-linkable rubber composition in the range from 1 to 10 phr.
  • the cross -linkable rubber composition further comprises at least one antiozonant.
  • the preferred antiozonant is ozone protecting wax.
  • the antiozonant is present in an amount of from 0.1 to 3 phr.
  • the cross-linkable rubber composition comprises 100 phr of at least one elastomer, 30 to 90 phr of a filler, 1 to 20 phr of maleated castor oil, and 0.5 to 20 phr of a vulcanization system.
  • the cross-linkable rubber composition comprises 100 phr of at least one elastomer, 30 to 90 phr of a filler, 1 to 20 phr of maleated castor oil, 0.5 to 5 phr of at least one cross-linking agent, 1 to 7 phr of at least one vulcanization accelerator, and 1 to 8 phr of at least one vulcanization activator.
  • the cross -linkable rubber composition comprises 100 phr of at least one elastomer, 30 to 90 phr of a filler, 1 to 20 phr of maleated castor oil, 0.5 to 5 phr of at least one cross-linking agent, 1 to 7 phr of at least one vulcanization accelerator, 1 to 8 phr of at least one vulcanization activator, 1 to 10 phr of at least one antioxidant, and 0.1 to 3 phr of at least one antiozonant.
  • the cross-linkable rubber composition comprises:
  • SSBR solution-polymerized styrene -butadiene rubber
  • CBS n-cyclohexyl-2-benzothiazole sulfenamide
  • the present disclosure is directed to a cross-linked rubber composition, obtained by cross-linking the cross -linkable rubber composition disclosed herein.
  • the cross-linked rubber composition can be obtained by blending the cross -linkable rubber composition with a vulcanization system and optionally with one or more additives of the type defined above to produce a blend, and heating the blend at a predetermined temperature to form the cross-linked rubber composition.
  • the blend is heated to a temperature from 110° C to 200° C.
  • the cross-linked (vulcanized) rubber composition exhibits improved dispersion of filler particles, improved physical properties, improved wear resistance, and improved dynamic viscoelastic properties.
  • the cross-linked rubber composition produced according to an embodiment of the present disclosure has a tan delta value in the range from > 0.39 to ⁇ 0.57 as measured at -20°C as per ISO 4664-1. In one embodiment, the cross-linked rubber composition produced according to an embodiment of the present disclosure has a tan delta value in the range from > 0.11 to ⁇ 0.15 as measured at 60°C as per ISO 4664-1. In one embodiment, the cross-linked rubber composition produced according to an embodiment of the present disclosure has a tear strength in the range from 39.0 to 52.0 N/mm as determined by ASTM D 624.
  • the present disclosure is directed to a process for preparing a cross-linked rubber composition, comprising: combining at least one elastomer, a filler and maleated castor oil in a mixing vessel to form a cross-linkable rubber composition; blending the cross-linkable rubber composition with a vulcanization system and optionally with one or more additives of the type defined above to produce a blend; and heating the blend at a predetermined temperature to form the cross-linked (vulcanized) rubber composition.
  • the cross -linkable rubber composition or the blend can be produced by mixing the above-mentioned components by using conventional kneaders used in the rubber industry, such as heating rolls, kneaders, Banbury mixers and the like.
  • the blend can be cross-linked by heating it at temperatures ranging from 110° C to 200° C.
  • the resultant vulcanizate (cross-linked composition) can be used for tire applications such as tire treads, under treads, carcass, side walls, and bead portions.
  • the composition of the present disclosure can be used particularly as rubber for tire treads.
  • the present disclosure is directed to a tire or tire tread comprising the cross-linked rubber composition disclosed herein.
  • the present disclosure is directed to a finished or semifinished rubber article comprising the cross-linked rubber composition disclosed herein.
  • Maleated castor oil was prepared by reacting castor oil (CO) with maleic anhydride (MAH) in a fixed CO/MAH mole ratio of 1:3. The reaction was carried out in a three-neck flask equipped with a dean stark apparatus, a cold-water condenser, a magnetic stirrer, and a thermometer. A mixture of castor oil and xylene (at a ratio of 1:0 or 1:1 by weight) was added into the three-necked flask and heated to 140°C. Then, a portion of maleic anhydride was incrementally added to the mixture and the reaction took place for 5 h at 300 rpm. Then, xylene was removed by vacuum distillation to yield maleated castor oil.
  • FIG. 1 depicts the reaction scheme for the preparation of maleated castor oil by reaction of castor oil with maleic anhydride.
  • FIG. 2 shows a comparison of the FTIR spectrum of the castor oil to the FTIR spectrum of the maleated castor oil.
  • the maleated castor oil has characteristic FTIR peaks at 3440 cm’ 1 and 1650 cm’ 1 , as determined using ASTM E1252.
  • Rubber compositions were prepared according to the ingredients and amounts indicated in Table 1. Composition production was performed under industry standard conditions in two stages, as shown in Table 2. In the first stage, the elastomers (PBD and SSBR) were added to an internal rubber mixer and mixed for about 2-5 min. Then, plasticizer oil and HD Silica were added to the mixer and the resulting composition was mixed for 2-6 min. Then, 6-PPD, TMQ, ozone protecting wax, zinc oxide and stearic acid were added to the mixer. Subsequently, all the ingredients were mixed for 8-10 min. The material was discharged from the mixer and air cooled to room temperature.
  • elastomers PBD and SSBR
  • the material from the first stage and sulfur, CBS and DPG were added into an internal rubber mixer or a two-roll open mill rubber machine and mixed for 2-6 min.
  • the resulting composition was discharged from the mixer and air cooled.
  • Test pieces were produced from each of the compositions by optimal vulcanization under pressure at 160° C, and these test pieces were used to determine the material properties typical for the tire industry. Testing was performed according to ASTM and ISO test methods.
  • the rubber composition containing maleated castor oil shows better elongation at break and hardness than the rubber compositions containing conventional RAE oil or unmodified castor oil as plasticizer.
  • the rubber composition containing maleated castor oil shows better snow grip with lower dynamic modulus and higher tan delta at -20°C, as compared to the composition containing conventional RAE oil (Composition 1). Further, the composition with maleated castor oil exhibits better rolling resistance with higher dynamic modulus and comparable tan delta at 60°C as compared to the composition containing conventional RAE oil.
  • Example 3 Rubber compositions [0063] Rubber compositions 4 and 5 (containing 7 phr and 10 phr of maleated castor oil, respectively) were prepared according to the ingredients and amounts indicated in Table 8. The compositions were produced using the process similar to the one in Example 2. Testing of the rubber compositions was performed according to ASTM and ISO test methods.
  • Table 9 shows that the rubber composition containing 7 phr of maleated castor oil according to the embodiment of the present disclosure exhibits significantly higher Mooney viscosity than the conventional rubber composition (Composition 1). Also, the composition with maleated castor oil exhibits fast curing and better maximum torques compared with conventional rubber composition (Composition 1).
  • the rubber composition containing 7 phr of maleated castor oil shows higher hardness and higher modulus at 300% than the conventional rubber composition (composition 1). Also, the composition containing 7 phr of maleated castor oil had a tensile strength, modulus at 100%, rebound and elongation at break comparable to that of the conventional rubber composition.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • Engineering & Computer Science (AREA)
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  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne une composition de caoutchouc réticulable comprenant de l'huile de ricin maléatée en tant que plastifiant. L'huile de ricin maléatée d'origine biologique peut être utilisée en tant que remplacement partiel ou total de plastifiants à base de pétrole utilisés dans des applications de pneu.
PCT/IB2023/061166 2022-12-02 2023-11-06 Composition de caoutchouc respectueuse de l'environnement WO2024115988A1 (fr)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB592400A (en) * 1943-01-20 1947-09-17 British Thomson Houston Co Ltd Improvements in and relating to the manufacture of synthetic resins
GB711470A (en) * 1950-07-26 1954-07-07 United Kingdom Chemicals Ltd Improvements in or relating to compounding ingredients for rubber
CN107501959A (zh) * 2017-09-27 2017-12-22 芜湖华力五星电源科技有限公司 一种摩托车铅酸蓄电池用抗压安全阀

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB592400A (en) * 1943-01-20 1947-09-17 British Thomson Houston Co Ltd Improvements in and relating to the manufacture of synthetic resins
GB711470A (en) * 1950-07-26 1954-07-07 United Kingdom Chemicals Ltd Improvements in or relating to compounding ingredients for rubber
CN107501959A (zh) * 2017-09-27 2017-12-22 芜湖华力五星电源科技有限公司 一种摩托车铅酸蓄电池用抗压安全阀

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