WO2015183070A1 - Procédé de production de prépolymère de polyuréthanne à base d'huile naturelle - Google Patents

Procédé de production de prépolymère de polyuréthanne à base d'huile naturelle Download PDF

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Publication number
WO2015183070A1
WO2015183070A1 PCT/MY2015/000041 MY2015000041W WO2015183070A1 WO 2015183070 A1 WO2015183070 A1 WO 2015183070A1 MY 2015000041 W MY2015000041 W MY 2015000041W WO 2015183070 A1 WO2015183070 A1 WO 2015183070A1
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WO
WIPO (PCT)
Prior art keywords
polyol
bio
diisocyanate
pko
group
Prior art date
Application number
PCT/MY2015/000041
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English (en)
Inventor
Haji Badri KHAIRIAH
Original Assignee
Universiti Kebangsaan Malaysia (Ukm)
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 Universiti Kebangsaan Malaysia (Ukm) filed Critical Universiti Kebangsaan Malaysia (Ukm)
Publication of WO2015183070A1 publication Critical patent/WO2015183070A1/fr

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Classifications

    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8051—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/36
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3206—Polyhydroxy compounds aliphatic
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/36—Hydroxylated esters of higher fatty 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
    • C08G18/3823—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups
    • C08G18/3825—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups containing amide groups
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8054—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/38
    • C08G18/8058—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/38 with compounds of C08G18/3819

Definitions

  • the present invention relates to a method to produce polyurethane (PU) prepolymer from biopolyol, selected from the group consisting of palm kernel oil-based polyol (PKO-p), coconut oil-based polyol (CO-p) and soybean polyol (SB-p).
  • biopolyol selected from the group consisting of palm kernel oil-based polyol (PKO-p), coconut oil-based polyol (CO-p) and soybean polyol (SB-p).
  • PU Polyurethane
  • plant oil polyols such as vegetable oils like palm oil, soybean oil, coconut oil, sunflower oil, olive oil and canola oil and combined with green technology to produce useful polymers such as PU.
  • PU can be produced via different methods.
  • a prior art described a simple one step process of producing PU polyester via esterification process with condensation throughout. In general, single step polymerization takes place when polyol, diisocyanate and catalyst are mixed together and chain extension takes place in one step. As a result, heat is liberated.
  • Another conventional prior art describes the production of PU via quasiprepolymer method. This method is the reaction between polyol reacted with an excess of diisocyanate where the urethane prepolymer contains higher free isocyanate content known as isocyanate quasiprepolymer or semiprepolymer where the diisocyanate molecules are partially reacted with polyol.
  • Malaysia patent MY-145094-A described a process for preparing natural oil-based polyesters and polyamides. Palm kernel oil or coconut oil is processed in two steps involving polyesterification and polycondensation process. It involves adding of palm kernel oil or coconut oil to a mixture comprising polyhydric alcohol. Polysaccharide alcohol catalyst is added to improve the process.
  • US patent US 6,399,698 provide an isocyanate prepolymer for making polyurethanes.
  • the prepolymer is synthesized by combining epoxidized natural oils with isocyanates and a catalyst.
  • the prepolymer contains oxazolidone rings that can react with polyols to form polyurethane.
  • US patent US 8,293,808 disclosed a polyurethane foam prepared by reacting in presence of a blowing agent, a polyisocyanate with an active hydrogen containing composition that includes a modified vegetable oil-based polyol. The treatment involved modifying the double bond of the vegetable oil.
  • the process gives off heat when urethane bonds were formed and causes shrinkage problem while isocyanate vapor levels are present.
  • the present invention is made in view of the prior arts described above where the proposed method, the prepolymerization method, allows for lower isocyanate vapour levels and reduction of exotherm of the final reaction as no heating is carried out. This method also allows for partial dissipation of the exorthem prior to the formation of PU.
  • This invention discloses a method of producing prepolymer for PU, without heating process, using vegetable oil bio-polyol selected from the group consisting of palm kernel oil-based polyol (PKO-p), coconut oil-based polyol (CO-p) and soybean polyol (SB-p).
  • PKO-p palm kernel oil-based polyol
  • CO-p coconut oil-based polyol
  • SB-p soybean polyol
  • Bio-polyol such as PKO-p in solution form is mixed with diisocyanate under nitrogen gas atmosphere, said PKO-p to diisocyanate in weight ratio of about 0.75:1 to 2:1 to form urethane prepolymer.
  • PKO-p was diluted in industrial grade solvents selected from the group consisting of tetrahydrofuran (THF) solution in 15 to 35 % (w/w), industrial grade acetone in 3-35% (w/w) and dimethyl sulfoxide in 8-15% (w/w).
  • THF tetrahydrofuran
  • the diisocyanate is selected form the group consisting of 2,4'-diphenylmethane diisocyanate (2,4'-MDI) or 4,4'-diphenylmethane diisocyanate (4,4'-MDI) or mixtures of both isomers.
  • the diisocyanate can possibly be in its presence form or diluted in the selected industrial grade solvent.
  • the solvent for diisocyanate, if used, must be of the same type of solvent that dilute PKO-p.
  • the PKO-p in solvent and the diisocyanate in solvent are known as prepolymers.
  • the prepolymers are agitated, solution-casted and cured to form PU.
  • the PU produced via this invention is a clear, either semi-flexible or flexible film that can be used in coating, adhesive, sealant and elastomer industry, especially as coating onto fiberboard due to its hydrophobic properties.
  • the usage is also applicable for solar cells as semiconductor elastomeric substrate to replace glass as well as for other PU industries.
  • Fig. 1 is a figure showing the general structure of polyurethane.
  • Fig. 2 is a figure showing the structure of PKO-p polyol.
  • Fig. 3 is a figure showing the structure of diisocyanate (4,4'-MDI).
  • Fig. 4 is a figure showing the structure of urethane polymer with isocyanate end group.
  • Fig. 5 is a figure showing the structure of polyurethane synthesized according to the invention.
  • Fig. 6 is a figure showing the repeating unit in the structure of polyurethane synthesized according to the invention.
  • Polyurethane (PU) (20) is based on polyol.
  • Preparation of proposed PU (30) via prepolymerization involves the formation of urethane polymer at the initial stage of reaction between polyol (22) and diisocyanate (24). Then, the urethane prepolymer (26) may be chain extended with diol, or any other hydroxyl containing substance, and cured to form PU (30).
  • one of the isocyanate (24) groups, NCO will react with a hydroxyl group, OH of the polyol (22) and the other isocyanate (24) group reacts with the second OH group.
  • the resultant urethane prepolymer has two isocyanate groups at both ends (28) of urethane prepolymer (30) with urethane bonds. This creates new properties to the polyurethane backbone as compared to conventional method (20) where the former still maintaining the same repeating unit (32).
  • Both prepolymers are diluted in industrial grade solvents selected from the group consisting of tetrahydrofuran (THF) solution in 15 to 35 % (w/w), industrial grade acetone in 3-35% (w/w) and dimethyl sulfoxide in 8-15% (w/w).
  • THF tetrahydrofuran
  • PKO-p is used as the renewable raw material where prepolymerization method is carried out.
  • the solvent used may be tetrahydrofuran (THF), acetone, dimethyl sulfoxide (DMSO) or N-methy-2-pyrrolidone (NMP) while the chain extender can be any range of glycol selected from the group of monoethylene glycol, diethylene glycol, and polyethylene glycol of molecular weight ranging from 200 to 20,000.
  • the diisocyanate are 2,4'-diphenylmethane diisocyanate (2,4'-MDI) or 4,4'- diphenylmethane diisocyanate (4,4'-MDI).
  • the PKO is initially dissolved in THF before mixing with MDI in a round bottom flask under nitrogen gas atmosphere at ambient temperature to form urethane prepolymer (26).
  • DEG is then added at varying amount to the PKO.
  • the mixture is then agitated at 200 rpm for an hour at room temperature.
  • the mixture is then casted into a translucent film of about 50 microns thickness onto a Teflon plate.
  • the film is then dried in a vacuum oven at 35-55°C for 12-24 h to remove the solvent.
  • the final produced PU (30) is yellow, translucent and void-free films.
  • Example 3 PKO-p is reacted with 2,4'-MDI in 5-35 mL acetone at varying NCO/OH weight ratio of 100/100, 100/150, 100/200 and 100/250.
  • the reaction is conducted at ambient temperature under nitrogen gas atmosphere in a glass flask.
  • the pre-polymer solutions are stirred to a homogenous solution for 5 min and the solution was casted to a teflon mould and allowed to evaporate at room temperature for an hour.
  • the produced films were kept in a desiccator for the further characterization.
  • the final cured films showed PU are from rigid and brittle to semi-rigid and flexible films. Curing can be performed at mild condition.
  • the chemical route of producing PU (30) via this prepolymerization method in this invention is as follows and the corresponding chemical structure for PU (30), polyol (22), isocyanate (24) and urethane polymer (26) with isocyanate end group (28) is shown as Figure 1 to Figure 6, respectively.
  • the final PU (30) is consistent where all MDI has completely reacted to form PU (30) and the urethane bond is the main polymeric chain in the PU (20) as indicated by the hydrogen bonding formed between soft segmented PKO-p chains with hard segmented MDI.
  • a method of producing environmentally friendly PU (20) via prepolymerization method without heating process using renewable vegetable oil is disclosed.
  • Prepolymerization is conducted for PKO-p (22) with MDI for diisocyanate component, acetone as the solvent and DEG as chain extender in varying ratios under nitrogen gas atmosphere at ambient temperature.
  • the PU produced via this invention is clear and semi flexible film that can be used in coating, adhesive and sealant industry especially as coating onto fiberboard due to its hydrophobic properties, solar cells, as semiconductor substrate to replace glass and other PU industries.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

La présente invention concerne un procédé de production d'un polyuréthanne (PU) (30) respectueux de l'environnement par le biais d'un procédé de prépolymérisation, à l'aide de biopolyol d'huile végétale, ledit biopolyol étant choisi dans le groupe constitué par du polyol à base d'huile de palmiste (PKO) (22), du polyol à base d'huile de noix de coco (CO-p) et du polyol de soja (SB-p) en tant que matière première renouvelable. La prépolymérisation est effectuée pour le PKO-p (22) avec du 2,4-diphénylméthanediisocyanate (MDl) pour le composant diisocyanate, du tétrahydrofurane (THF) en tant que solvant et du diéthylèneglycol (DEG) comme allongeur de chaîne dans des proportions variables sous atmosphère d'azote gazeux à température ambiante. Le PU produit par l'intermédiaire de la présente invention est clair, présentant un film qui est de semi-flexible à flexible, qui peut être utilisé dans l'industrie du revêtement, de l'adhésif et des produits de scellement, notamment comme revêtement sur un panneau de fibres en raison de ses propriétés hydrophobes. L'utilisation est également applicable aux photopiles, en tant que substrat semi-conducteur de remplacement de verre et d'autres industries du PU (20). En outre, l'invention permet potentiellement un coût de production inférieur et une fabrication écologique sans la dépendance à des matériaux à base de pétrole.
PCT/MY2015/000041 2014-05-26 2015-05-25 Procédé de production de prépolymère de polyuréthanne à base d'huile naturelle WO2015183070A1 (fr)

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MYPI2014701352 2014-05-26

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108329454A (zh) * 2018-03-05 2018-07-27 河南省科学院高新技术研究中心 一种聚氨酯及其制备方法和载药胶束
WO2022046681A1 (fr) * 2020-08-24 2022-03-03 Inoac Us, Inc. Mousse biorenouvelable de polyuréthane pour applications de nettoyage par des consommateurs
CN115521747A (zh) * 2022-10-09 2022-12-27 中国林业科学研究院林产化学工业研究所 一种室温固化的植物油基耐水耐腐蚀聚氨酯胶黏剂及制法

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5971324A (ja) * 1982-10-16 1984-04-23 Dainippon Ink & Chem Inc 水分散性樹脂組成物
JPH02173115A (ja) * 1988-12-27 1990-07-04 Dainippon Ink & Chem Inc 活性イソシアネート基を有する油変性ウレタン樹脂
JPH06279562A (ja) * 1993-03-29 1994-10-04 Dainippon Ink & Chem Inc ウレタン化油組成物
JP2009167255A (ja) * 2008-01-11 2009-07-30 Inoac Corp 低燃焼性軟質ポリウレタン発泡体
WO2010100421A2 (fr) * 2009-03-04 2010-09-10 Green Urethanes Limited Mousse de polyuréthane
WO2010114643A1 (fr) * 2009-03-31 2010-10-07 Dow Global Technologies Inc. Dispersion de polyuréthane, son procédé de production, articles revêtus et procédé pour le revêtement d'articles
WO2011062472A1 (fr) * 2009-11-23 2011-05-26 Universiti Malaya Panneau de fibres fabriqué à partir de déchets agricoles et son procédé de fabrication
WO2013050854A1 (fr) * 2011-10-03 2013-04-11 Industrial Agraria La Palma Limitada, Indupalma Ltda. Procédés permettant d'obtenir un polyol à partir d'huile de palme, polyols obtenus selon ces procédés, produits dérivés de ce polyol et procédé de préparation
WO2014069556A1 (fr) * 2012-11-05 2014-05-08 三井化学株式会社 Composition à base d'un prémélange de résine, composition pour mousse de polyuréthane rigide et mousse de polyuréthane rigide

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5971324A (ja) * 1982-10-16 1984-04-23 Dainippon Ink & Chem Inc 水分散性樹脂組成物
JPH02173115A (ja) * 1988-12-27 1990-07-04 Dainippon Ink & Chem Inc 活性イソシアネート基を有する油変性ウレタン樹脂
JPH06279562A (ja) * 1993-03-29 1994-10-04 Dainippon Ink & Chem Inc ウレタン化油組成物
JP2009167255A (ja) * 2008-01-11 2009-07-30 Inoac Corp 低燃焼性軟質ポリウレタン発泡体
WO2010100421A2 (fr) * 2009-03-04 2010-09-10 Green Urethanes Limited Mousse de polyuréthane
WO2010114643A1 (fr) * 2009-03-31 2010-10-07 Dow Global Technologies Inc. Dispersion de polyuréthane, son procédé de production, articles revêtus et procédé pour le revêtement d'articles
WO2011062472A1 (fr) * 2009-11-23 2011-05-26 Universiti Malaya Panneau de fibres fabriqué à partir de déchets agricoles et son procédé de fabrication
WO2013050854A1 (fr) * 2011-10-03 2013-04-11 Industrial Agraria La Palma Limitada, Indupalma Ltda. Procédés permettant d'obtenir un polyol à partir d'huile de palme, polyols obtenus selon ces procédés, produits dérivés de ce polyol et procédé de préparation
WO2014069556A1 (fr) * 2012-11-05 2014-05-08 三井化学株式会社 Composition à base d'un prémélange de résine, composition pour mousse de polyuréthane rigide et mousse de polyuréthane rigide

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108329454A (zh) * 2018-03-05 2018-07-27 河南省科学院高新技术研究中心 一种聚氨酯及其制备方法和载药胶束
WO2022046681A1 (fr) * 2020-08-24 2022-03-03 Inoac Us, Inc. Mousse biorenouvelable de polyuréthane pour applications de nettoyage par des consommateurs
CN115521747A (zh) * 2022-10-09 2022-12-27 中国林业科学研究院林产化学工业研究所 一种室温固化的植物油基耐水耐腐蚀聚氨酯胶黏剂及制法
CN115521747B (zh) * 2022-10-09 2024-02-02 中国林业科学研究院林产化学工业研究所 一种室温固化的植物油基耐水耐腐蚀聚氨酯胶黏剂及制法

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