WO2022169354A1 - Alkyde à base d'acide gras d'huile de palme biocompatible, procédé de production de l'alkyde et utilisation de l'alkyde - Google Patents

Alkyde à base d'acide gras d'huile de palme biocompatible, procédé de production de l'alkyde et utilisation de l'alkyde Download PDF

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Publication number
WO2022169354A1
WO2022169354A1 PCT/MY2022/050006 MY2022050006W WO2022169354A1 WO 2022169354 A1 WO2022169354 A1 WO 2022169354A1 MY 2022050006 W MY2022050006 W MY 2022050006W WO 2022169354 A1 WO2022169354 A1 WO 2022169354A1
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alkyd
fatty acid
monomer
rubber
trifunctional
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PCT/MY2022/050006
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English (en)
Inventor
Kok Chong Yong
Siang Yin LEE
Hani Afiffa Binti MOHD HANIF
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Lembaga Getah Malaysia
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Publication of WO2022169354A1 publication Critical patent/WO2022169354A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/46—Polyesters chemically modified by esterification
    • C08G63/48—Polyesters chemically modified by esterification by unsaturated higher fatty oils or their acids; by resin acids
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/04—Carbon
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/08—Polyesters modified with higher fatty oils or their acids, or with resins or resin acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L7/00—Compositions of natural rubber
    • 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
    • C08L9/02—Copolymers with acrylonitrile
    • 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

Definitions

  • BIOCOMPATIBLE PALM OIL FATTY ACID-BASED ALKYD THE METHOD OF PRODUCING THE ALKYD AND USE OF THE ALKYD
  • This invention generally relates to alkyds. More particularly, the invention relates to a biocompatible palm oil fatty acid-based alkyd, the method of producing the alkyd and use of the alkyd.
  • Rubber process oil is derived from petroleum crude which has been distilled. Process oil is used to facilitate the operation of the manufacturing of both synthetic and natural rubber compositions such as mixing, moulding, extruding etc. as the process oil can penetrate the rubber polymer. Process oil is also used to improve the physical properties of rubber products.
  • PAH polycyclic aromatic hydrocarbons
  • Alkyd resins are polyfunctional vegetable oil-modified polyesters, synthesized via a step- wise polymerization process.
  • Lee 2 discloses the synthesis of a series of alkyd resins from palm kernel oil. These alkyds were reported for its use as tackifiers in the rubber composition for tire and pneumatic tire composition applications 3 . However, the biocompatibility of these alkyds were not reported.
  • a palm oil fatty acid-based alkyd comprising a palm fatty acid comprising stearic acid, and a hydrophilic trifunctional neopentyl monomer.
  • the hydrophilic trifunctional neopentyl monomer may be 2,2- bis(hydroxymethyl)propionic acid.
  • the alkyd may comprise about 70 wt% to about 80 wt%, preferably about 80 wt% of palm fatty acid; and about 20 wt% to about 30 wt%, preferably about 20 wt% of hydrophilic trifunctional neopentyl monomer.
  • a method for manufacturing the alkyd comprises the steps of: i) providing a palm fatty acid comprising stearic acid, ii) providing a hydrophilic trifunctional neopentyl monomer; iii) mixing the palm fatty acid and the hydrophilic trifunctional neopentyl monomer together in the presence of a catalyst to form a mixture; and iv) subjecting the mixture to a polyesterification reaction.
  • the hydrophilic trifunctional neopentyl monomer may be 2,2- bis(hydroxymethyl)propionic acid.
  • the amount of the catalyst provided may be about 0.1 wt%.
  • the catalyst used may be sodium hydroxide.
  • the temperature of the polyesterification reaction of step (iv) may be about 180°C to about 200°C whereas the reaction time is about 10 hours to about 20 hours, preferably about 18 hours.
  • a process oil that comprises the alkyd of the present invention that may be used in the manufacture of carbon black-filled rubber compositions.
  • a use of the alkyd as a processing aid in the manufacture of carbon black-filled rubber compositions.
  • the alkyd of the present invention provides for various beneficial properties when used as a processing aid when compared to the use of conventional petroleum derived process oil in the manufacture of carbon black-filled rubber compositions.
  • the alkyd of the present invention when used as a processing aid provides for comparable physical properties for tensile strength, elongation at break value, tensile modulus and compression set as well as improved ageing properties when compared to a rubber composition manufactured using conventional process oil.
  • the present invention is directed at a biocompatible alkyd derived from palm oil fatty acid, the method of producing the alkyd and its use.
  • a palm oil fatty acid-based alkyd comprising a palm oil fatty acid and a hydrophilic trifunctional neopentyl monomer.
  • the palm fatty acid is palm-derived stearic acid.
  • the hydrophilic trifunctional neopentyl monomer comprises at least one hydroxy and at least one carboxy functional group.
  • the hydrophilic trifunctional neopentyl monomer preferably comprises a combination of two hydroxy and one carboxy functional groups.
  • palm-derived stearic acid comprising 18 carbon atoms with purity of at least 90% was used.
  • the purity of stearic acid of at least 95% is preferred and a purity of at least 97% is most preferable.
  • Stearic acid is a monosaturated fatty acid having the longest carbon chain length that can be found in palm oil.
  • a monosaturated fatty acid having the longest carbon chain length provides good compatibility and miscibility with non-polar rubber polymers during physical blending.
  • the non-polar rubber polymers used may include but not limited to natural rubber (NR), butadiene rubber (BR), and ethylene propylene rubber (EPDM or EPR).
  • Stearic acid is commonly used for accelerated sulphur vulcanization of rubber. Stearic acid by itself can cause acute oral toxicity, dermal irritation, and is toxic to aquatic life. However, when stearic acid was used in the manufacture of the alkyd of the present invention, the alkyd was tested and found to be non-toxic. It was determined that, although the monomers such as stearic acid by itself are often toxic, most polymers comprising these monomers are safe and non-toxic.
  • the hydrophilic trifunctional neopentyl monomer may be 2,2-bis(hydroxymethyl)propionic acid, or also named as 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoic acid.
  • This hydrophilic trifunctional neopentyl monomer hereinafter is referred to as dimethylol propionic acid (DMPA).
  • DMPA dimethylol propionic acid
  • the purity of DMPA is at least 98%.
  • DMPA behaves as a di- functional monomer rather than a tri-functional monomer due to a difference in reactivity of carboxylic acid groups in monomers.
  • DMPA with secondary carboxylic acid groups are more steric hindered and hence having a lower reactivity relative to stearic acid with primary and unhindered carboxylic acid groups. It was assumed that none of the carboxylic acid groups of DMPA reacted.
  • the method of producing the alkyd is using a block copolymerization process which resulted in the alkyd of the present invention having esterified stearic acid groups functioning as non-polar moieties and the unreacted carboxylic acid groups functioning as polar moieties.
  • These polar moieties provide good compatibility and miscibility with polar polymers or rubbers during physical blending.
  • the polar rubbers used may include but not limited to (acrylo) nitrile butadiene rubber (NBR) and chloroprene rubber (CR).
  • composition of the alkyd comprises palm stearic acid of at least about 70 wt% to at most about 80 wt%, preferably 80 wt% and DMPA of at least about 20 wt% to at most about 30 wt%, preferably 20 wt%.
  • Stearic acid is derived from palm oil fatty acid while DMPA is essentially a non-toxic compound. Both compounds are not derived from petroleum and provides a biocompatible alternative to petroleum derived products.
  • the alkyd of the present invention is subjected to several characterization tests to determine the acid values through acid value titration, glass transition temperatures through differential scanning calorimetry and molecular weights through gel permeation chromatography.
  • the test results confirm that the alkyd has a moderately low number-average molecular weight, M n of nearly 1000 g/mol and moderately low T g of about 30°C.
  • the moderately long hydrocarbon chains of the alkyd may improve its miscibility with non-polar polymers or rubbers.
  • the moderately low T g of the alkyd has a good plasticizing effect during physical mixing with other polymers or rubbers.
  • the alkyd was established to have a higher acid number, indicating it has polar moieties to enhance miscibility with polar polymers or rubbers.
  • the molecular structure of the alkyd described above comprises two opposing ends with different polarities which enables good miscibility with both polar and non-polar polymers or rubbers during physical blending. Details of these tests are shown in Example 1.
  • a biocompatibility test was carried out by using in vitro succinate dehydrogenase activity (MTT assay) against three cell lines i.e. human keratinocytes, mouse hepatocytes and canine kidney cells. The cytotoxicity level was determined based on the cell viability relative to the control group in accordance with ISO 10993-5:2009. A control group containing cells without alkyd treatment was also provided. Test results show that all three cell lines had more than 80% cell viability which confirms that the alkyd is non-cytotoxic. Details of the test are shown in Example 2.
  • MTT assay in vitro succinate dehydrogenase activity
  • the method for producing the alkyd of the present invention mainly comprises the following steps: i) providing a palm fatty acid and at least one hydrophilic trifunctional neopentyl monomer; ii) mixing the palm fatty acid and the hydrophilic trifunctional neopentyl monomer together in the presence of a catalyst to form a mixture; and iii) reacting the mixture via a polyesterification reaction.
  • the catalyst used is sodium hydroxide.
  • Sodium hydroxide is a non-toxic compound and is used in the present invention to substitute conventionally used catalysts such as lithium hydroxide or metal oxide catalysts such as tin oxides. These conventional catalysts are highly toxic.
  • the use of sodium hydroxide in the present invention provides for the non- cytotoxic properties of the present invention.
  • the preferred amount of catalyst is about 0.1 wt%.
  • the palm oil fatty acid, monomers and catalyst are mixed in any suitable vessel.
  • a reaction flask is used in the present invention as it provided effective control of the reaction.
  • the reaction flask is equipped with a mechanical agitator, thermometer, nitrogen gas inlet and a Dean-Stark decanter.
  • the polyesterification reaction is carried out at a temperature of at least about 180°C and at most about 200°C.
  • the reaction time is at least about 10 hours, preferably at least about 18 hours and at most about 20 hours. Any other suitable reaction temperature and time may be applied.
  • polyesterification reaction heat is applied to the reaction vessel and gradually increased and subsequently maintained for a specific length of time. This allows for a slow polyesterification rate to occur, allowing uniform distribution of monomers to form hydrophobes and hydrophilies along the alkyd's backbone.
  • the reaction is allowed to continue until reaching an acid value of at least about 80 mg KOH/g of resin and at most about 100 mg KOH/g resin.
  • alkyds are suitable for use as a processing aid in the manufacture of carbon black-filled rubber compositions.
  • Carbon black was selected as it was the most widely available filler used for rubber compounding.
  • a process oil used in the manufacture of rubber compositions enhances the processability of the composition by improving the dispersion of fillers and flow characteristics of the composition.
  • the rubber composition comprises the following components: i) a rubber host; ii) a carbon black filler; iii) a vulcanising agent; iv) an accelerator; v) a vulcanisation activator; and vi) a process oil.
  • the rubber host may be derived from solid synthetic rubber or natural rubber. Any suitable grade of synthetic or natural rubber may be used which includes, but not limited to acrylonitrile butadiene rubber (NBR), styrene butadiene (SBR), polybutadiene rubber (BR), ethylene-propylene-diene rubber (EPDM), polyisoperene rubber (IR), natural rubber (NR), epoxidised natural rubber (ENR), deproteinised natural rubber (DPNR) and any mixture thereof.
  • NBR acrylonitrile butadiene rubber
  • SBR styrene butadiene
  • BR polybutadiene rubber
  • EPDM ethylene-propylene-diene rubber
  • IR polyisoperene rubber
  • NR natural rubber
  • EMR epoxidised natural rubber
  • DPNR deproteinised natural rubber
  • Carbon black acts as a filler for the rubber composition.
  • Any suitable type or grade of carbon black may be used such as N 110 Super abrasion furnace (SAF), N220 Intermediate SAF (ISaFE), N326, N330, N375 High Abrasion Furnace (HAF), N300 Easy processing channel (EPC), N550 Fast Extruding Furnace (FEF), N660 High Modulus Furnace (HMF), N762, N770 Semi Reinforcing Furnace (SRF), N880 Fine thermal (FT) and/or N990 Medium thermal (MT).
  • SAF Super abrasion furnace
  • ISaFE Intermediate SAF
  • HAF High Abrasion Furnace
  • EPC Easy processing channel
  • FEF Fast Extruding Furnace
  • HMF High Modulus Furnace
  • SRF N770 Semi Reinforcing Furnace
  • FT Fine thermal
  • MT Medium thermal
  • N550 FEF black was used at an amount of about 20.0 p.p.h.r. to about 10
  • any suitable vulcanising agent may be used for vulcanisation of the rubber composition.
  • the rubber mixture is vulcanised by adding sulphur at an amount of about 0.1 p.p.h.r. to about 5.0 p.p.h.r., preferably about 1.0 p.p.h.r. to about 2.5 p.p.h.r..
  • the accelerator used may include but are not limited to diphenylguanidine (DPG), tetramethylthiuram monosulphide (TMTM), tetramethylthiuram disulphide (TMTD), tetrabutylthiuram disulphide (TBTD), tetraethylthiuram disulphide (TETD), zinc dimethyldithiocarbamate (ZDMC), zinc diethyldithiocarbamate (ZEDC), zinc dibutyldithiocarbamate (ZDBC), 2- mercaptobenzothiazole (MBT), 2,2'-dibenzothiazyl disulphide (MBTS), morpholinylbenzothiazole-2- sulphenamide (MBS), N-t-butylbenzothiazole-2- sulphenamide (TBBS), N-cyclohexylbenzothiazole-2-sulphenamide (CBS) and any mixture thereof.
  • the accelerator may be added in an amount
  • vulcanization activator Any suitable vulcanization activator may be used.
  • the vulcanization activator used may be selected from a group consisting of zinc oxide, stearic acid, and zinc-2-ethylhexanoate which may be used alone or in combination.
  • zinc oxide and stearic acid was used.
  • Zinc oxide may be added in an amount of about 3.0 p.p.h.r. to about 10.0 p.p.h.r., and preferably about 2.0 p.p.h.r. to about 5.0 p.p.h.r while stearic acid may be added in an amount of about 1.0 p.p.h.r. to about 5.0 p.p.h.r., and preferably about 1.0 p.p.h.r. to about 2.0 p.p.h.r..
  • the alkyd of the present invention was used as a process oil.
  • various amounts of the alkyd was added into the rubber composition, for example, 0.0 p.p.h.r., 2.5 p.p.h.r., 5.0 p.p.h.r., 7.5 p.p.h.r. and 10.0 p.p.h.r..
  • the method of producing the rubber composition are as follows: i) providing the appropriate amount of a rubber host, a carbon black, a vulcanising agent, an accelerator, a vulcanisation activator and the alkyd of the present invention; ii) mixing all components together at ambient temperature to produce a mixture; and iii) curing the mixture.
  • step (ii) may be conducted at room temperature as a start. Any other suitable operating temperature may be used.
  • the operational temperature of the mixing of step (ii) should not exceed about 120 °C, whereas the preferred temperature is about 70 °C to about 100 °C.
  • step (iii) the mixture is cured using heat.
  • Any suitable curing device may be used such as heating ovens and hot pressers.
  • a hot presser was used.
  • the rubber mixture is placed under a rheometer at a curing temperature, preferably about 140 °C to about 180°C. Rheometer results reveal the cure time needed at that particular curing temperature.
  • a curing temperature preferably about 140 °C to about 180°C.
  • Rheometer results reveal the cure time needed at that particular curing temperature.
  • an about 140 °C to about 150 °C curing temperature was used.
  • the resulting batches of synthetic and natural rubber compositions having different proportions of the process oil are then subjected to tests to determine the physical properties of the rubber compositions. From the test results, it is shown that the rubber composition comprising the alkyd of the present invention acting as a processing aid has comparable physical properties such as tensile strength elongation at break range, tensile modulus and compression set when compared to a rubber composition manufactured using conventional process oil. After accelerated ageing, the retention of these physical properties was also comparable. In the case of natural rubber, it exhibited superior retention of tensile strength and elongation at break range compared to the rubber composition manufactured using conventional process oil. Details of these tests are in Examples 4 and 5.
  • Acid number was determined following a procedure adapted from ASTM D1980-87(1998), with a modification in which the alkyd of known weight was dissolved in a mixture of ethanol and toluene in a ratio of 1:2 before being titrated with standardized potassium hydroxide solution.
  • Glass transition temperatures ( 7 ⁇ ) was measured using a Mettler Toledo DSC 1 differential scanning calorimetry (DSC) analyser and the data was analysed using STARe SW 13.00 software. Temperature calibration was carried out using cyclohexane. Sample was subjected to heat-cooling cycles from -120°C to 80°C at a heating rate of 10°C/min under nitrogen with the flow rate of 50 mL/min. The glass transition temperature ( 7 ⁇ ) was determined as the midpoint of the change in the pre- and post-transition baselines associated with the difference in heat capacity at the glass transition. Result obtained was corrected with cyclohexane and the DSC test was performed following a procedure adapted from ASTM D3418-15 (2015).
  • Number-average molecular weight was determined using a Malvern gel permeation chromatography (GPC) Viscotek using 3 CLM3005-T5000, Organic GPC/SEC columns.
  • the alkyd was dissolved in tetra hydrofuran (THF) at 0.2% w/v and filtered using polytetrafluoroethylene filter with pore size of 0.45 pm.
  • THF tetra hydrofuran
  • a flow rate of 0.8 mL/min was employed. Calibration was performed against polyisoprene standards.
  • the physicochemical properties of alkyd such as acid number, glass transition temperature and number-average molecular weight are indicated in Table 1.
  • Table 1 The physiochemical properties of alkyd _ Acid number Glass transition Number-average molecular
  • the moderately long hydrocarbon chains of the alkyd may improve its miscibility with non-polar polymers or rubbers.
  • the moderately low T g of the alkyd has a good plasticizing effect during physical mixing with other polymers or rubbers.
  • the alkyd was established to have a higher acid number, indicating it has polar moieties to enhance miscibility with polar polymers or rubbers.
  • the biocompatibility of the alkyd was evaluated using MTT assays against three cell lines, which were human keratinocytes (HaCaT), mouse hepatocytes (H2.35) and canine kidney cells (MDCK).
  • HaCaT human keratinocytes
  • H2.35 mouse hepatocytes
  • MDCK canine kidney cells
  • the cytotoxicity level was rated based on the cell viability relatives to control in accordance with the ISO 10993-5:2009 standard. The test was carried out in both dose- and time-dependent manners, with 6 varying concentrations of alkyd (3.125, 6.250, 12.500, 25.000, 50.000 and 100.000 pg/mL), and the cells were treated for 3 prolonged durations (24, 48 and 72 hours).
  • the control group are cells without any alkyd treatment. Table 2 summarized the cytotoxicity results.
  • Tensile tests were carried out following BS ISO 37 where tensile strength, elongation at break and tensile modulus at 100% elongation were obtained. Compression set tests using 25% strain was performed in accordance with ISO 815. Ageing condition of tensile tests was set at 100 °C for 72 ⁇ 2 h whereas compression set samples were aged at 70 °C for 22 ⁇ 2 h. The retention percentages of tensile properties were calculated following the equation:
  • Tensile tests were carried out following BS ISO 37 where tensile strength, elongation at break and tensile modulus at 100% elongation were obtained. Compression set tests using 25% strain was performed in accordance with ISO 815. Ageing condition of tensile tests was set at 100 °C for 72 ⁇ 2 h whereas compression set samples were aged at 70 °C for 22 ⁇ 2 h. The retention percentages of tensile properties were calculated following the equation:
  • the carbon black-filled rubber composition comprising the alkyd of the present invention used as a processing aid has comparable physical properties when compared to a similar rubber composition that uses petroleum derived process oil.
  • the natural rubber composition in Example 3 possesses superior retention of physical properties, particularly, tensile strength and elongation at break in comparison to the rubber composition using petroleum derived process oil.
  • the alkyd of the present invention is suitable to be used as an alternative to petroleum derived process oil where the alkyd is environmentally friendly, biocompatible, fully derived from renewable resources and non-toxic.

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  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
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  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Selon un aspect de la présente invention, celle-ci concerne un alkyde à base d'acide gras d'huile de palme qui comprend un acide stéarique issu du palmier et un monomère néopentylique trifonctionnel hydrophile. Selon un autre aspect de la présente invention, celle-ci concerne un procédé de production de l'alkyde selon la présente invention. L'invention concerne également l'utilisation de l'alkyde en tant qu'auxiliaire de traitement dans la fabrication de compositions de caoutchouc remplies de noir de carbone et également d'une huile de traitement comprenant l'alkyde. L'alkyde selon la présente invention s'est avéré approprié pour être utilisé en tant qu'alternative aux huiles de traitement de caoutchouc issues du pétrole sans compromettre les propriétés physiques des compositions de caoutchouc ainsi obtenues.
PCT/MY2022/050006 2021-02-02 2022-01-26 Alkyde à base d'acide gras d'huile de palme biocompatible, procédé de production de l'alkyde et utilisation de l'alkyde WO2022169354A1 (fr)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0326310A1 (fr) * 1988-01-29 1989-08-02 Questra Chemicals Corp. Produits d'esters solides d'acides polyhydroxymonocarboxyliques à encombrement stérique
US20070100061A1 (en) * 2005-10-28 2007-05-03 Sumitomo Rubber Industries, Ltd. Rubber composition for tire and pneumatic tire using the same

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0326310A1 (fr) * 1988-01-29 1989-08-02 Questra Chemicals Corp. Produits d'esters solides d'acides polyhydroxymonocarboxyliques à encombrement stérique
US20070100061A1 (en) * 2005-10-28 2007-05-03 Sumitomo Rubber Industries, Ltd. Rubber composition for tire and pneumatic tire using the same

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
GAN, S N ET AL.: "Modifications of Natural Rubber and Epoxidised Natural Rubber Compounds by Palm Oil-based Alkyds", RUBBER TECHNOLOGY DEVELOPMENTS, vol. 9, 30 November 2008 (2008-11-30), pages 11 - 14, XP009539152, ISSN: 1675-0373 *
ISLAM, M R ET AL.: "Alkyd Based Resin from Non-Drying Oil", PROCEDIA ENGINEERING, vol. 90, 2014, pages 78 - 88, XP055960711 *
LEE, S Y ET AL.: "Reactions Between Epoxidized Natural Rubber and Palm Oil-Based Alkyds at Ambient Temperature", JOURNAL OF APPLIED POLYMER SCIENCE, vol. 120, 2011, pages 1503 - 1509 *

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