WO2017154878A1 - Composition pour moulage de mousse polyuréthane souple - Google Patents

Composition pour moulage de mousse polyuréthane souple Download PDF

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Publication number
WO2017154878A1
WO2017154878A1 PCT/JP2017/008925 JP2017008925W WO2017154878A1 WO 2017154878 A1 WO2017154878 A1 WO 2017154878A1 JP 2017008925 W JP2017008925 W JP 2017008925W WO 2017154878 A1 WO2017154878 A1 WO 2017154878A1
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WIPO (PCT)
Prior art keywords
polyol
polyurethane foam
mass
flexible polyurethane
foam
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Ceased
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PCT/JP2017/008925
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English (en)
Japanese (ja)
Inventor
石橋圭太
吉井直哉
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Tosoh Corp
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Tosoh Corp
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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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • 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
    • C08G18/08—Processes
    • 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
    • C08G18/70—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
    • 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
    • C08K5/13—Phenols; Phenolates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes

Definitions

  • the present invention relates to a flexible polyurethane foam molding composition and a flexible polyurethane foam comprising the composition.
  • the flexible polyurethane foam of the present invention is suitable for applications requiring heat resistance, such as in a vehicular engine room, an anti-vibration / sound insulation material for a generator, and a hot carpet.
  • soft polyurethane foam is used as these vibration-proof and sound-proof materials, since the heat-resistant temperature of the soft polyurethane foam is as low as 150 ° C. or lower, it cannot be disposed on a surface exposed to high temperatures such as in the vicinity of an engine.
  • Patent Documents 1 to 7 As a method for improving the heat resistance of a vibration-proof and heat-insulating material using a flexible polyurethane foam, there is known a method of laminating and integrating a heat-resistant nonwoven fabric or a resin film (Patent Documents 1 to 7). There is no known method for improving heat resistance alone.
  • the present invention has been made in view of the above-mentioned background art, and its problem is a flexible polyurethane having excellent heat resistance, which is used in a vehicle engine room, an anti-vibration / sound insulation material for a generator, a hot carpet, and the like. Is to provide a form.
  • the present invention includes the following embodiments.
  • a composition for molding a flexible polyurethane foam comprising a polyol (A), a hindered phenol compound (B), and a polyisocyanate (C), wherein the polyol (A) is castor oil and castor oil modified.
  • the polyol (A) contains 10 to 50% by mass of at least one polyol (A-1) selected from the group consisting of polyols, and the hindered phenolic compound (B) is 0% relative to the polyol (A).
  • polyisocyanate (C) contains diphenylmethane diisocyanate in the range of 50 to 80% by weight, and 2,2′-diphenylmethane diisocyanate and 2,4′- Diphenylmethane diisocyanate is diphenylmethane diisocyanate Flexible polyurethane foam molding composition characterized by containing 10 to 50% by weight relative to the amount.
  • the polyol (A) is at least one polyol (A-1) selected from the group consisting of castor oil and castor oil-modified polyol, and a polymer polyol (A-2) other than the polyol (A-1);
  • the polyol (A-1) has a number average molecular weight of 400 to 2000
  • the polymer polyol (A-2) is a polyether polyol having a number average molecular weight of 1000 to 10,000 and a nominal functional group number of 2 or more.
  • the flexible polyurethane foam molding composition as described in (1) or (2) above.
  • the apparent foam density of the flexible polyurethane foam obtained in the above (4) is 70 to 300 kg / m 3
  • the 25% compression hardness of the skin-attached foam test piece is 150 to 950 N / 314 cm 2
  • a method for producing a flexible polyurethane foam, wherein the foam elongation retention before and after a heat test at 150 ° C. for 150 hours is 75% or more.
  • the present invention it is possible to obtain excellent heat resistance in a flexible polyurethane foam, and it is very useful mainly as an anti-vibration / sound insulation material for an engine room for a vehicle or a generator.
  • the present invention relates to a composition for molding a flexible polyurethane foam produced using a specific polyol component and a hindered phenol-based compound constituting the flexible polyurethane foam as shown below.
  • the flexible polyurethane foam molding composition of the present invention comprises a polyol (A) containing at least one polyol (A-1) selected from the group consisting of castor oil and castor oil-modified polyol, and a hindered phenol compound (B). And a polyisocyanate (C), a flexible polyurethane foam molding composition.
  • Examples of at least one polyol (A-1) selected from the group consisting of castor oil and castor oil-modified polyol include refined castor oil, semi-refined castor oil, unrefined castor oil, and hydrogenated castor oil to which hydrogen has been added.
  • Castor oil derivatives may be mentioned, but CPR is preferably 8 or less.
  • CPR is an index indicating the amount of alkali metal remaining in the polyol, and affects the urethane reaction by the basicity derived from the alkali metal. If the CPR exceeds 8, the resulting flexible polyurethane foam has a stronger foam and may cause molding shrinkage.
  • castor oil-based polyol (A-1) examples include URIC H-24 and URIC H-30 manufactured by Ito Oil Co., but are not limited thereto.
  • the castor oil-based polyol (A-1) is used in an amount of 10 to 50% by mass in the polyol (A). If it is less than 10% by mass, the heat resistance cannot be sufficiently exhibited, and if it exceeds 50% by mass, the moldability deteriorates.
  • the number average molecular weight of the castor oil-based polyol (A-1) is preferably 400 to 2000. If it is less than 400, the soundproof performance of the flexible polyurethane foam may be lowered, and if it exceeds 2000, the compression residual strain of the flexible polyurethane foam may be lowered.
  • the polymer polyol (A-2) can be used as the polyol component.
  • the polymer polyol (A-2) is preferably selected from the group consisting of polyether polyols and polyester polyols in the present invention. Further, those having a number average molecular weight of 1,000 to 10,000 and a nominal functional group number of 2 or more are more desirable. If the number average molecular weight is less than the lower limit, the flexibility of the resulting foam tends to be insufficient, and if it exceeds the upper limit, the hardness of the flexible polyurethane foam tends to decrease. Further, when the nominal functional group number is less than 2, there arises a problem that the compressive residual strain is deteriorated. In addition, a nominal functional group number shows the average functional group number (number of active hydrogen atoms per molecule
  • polyether polyol polypropylene ethylene polyol, polytetramethylene ether glycol (PTG) or the like is used.
  • polyester polyol polycondensation type polyester polyol adipic acid ethylene glycol polyester polyol, lactone type polyester polyol polycaprolactone polyol. Etc. are used.
  • hindered phenol compound (B) used in the present invention examples include octyl 3- (4-hydroxy-3,5-diisopropylphenyl) propionate, pentaerythritol tetrakis [3- (3,5-di-tert- Butyl-4-hydroxyphenyl) propionate], 2,2′-thiodiethylbis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], 3- (3,5-di-tert -Butyl-4-hydroxyphenyl) stearyl propionate, N, N′-hexamethylenebis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propanamide], 2,4,6-tris (3 ′, 5′-tert-butyl-4′-hydroxybenzyl) mesitylene and the like.
  • These hindered phenol compounds preferably have a function as an antioxidant.
  • the addition amount of the hindered phenol compound is 0.1 to 5% by mass with respect to the polyol (A), preferably more than 1% by mass and 5% by mass or less.
  • the upper limit is exceeded, the molding stability of the foam is lowered, and when it is less than the lower limit, the heat resistance effect cannot be sufficiently obtained.
  • the polyisocyanate (C) used in the production of the flexible polyurethane foam in the present invention is 4,4′-diphenylmethane diisocyanate (hereinafter 4,4′-MDI), 2,4′-diphenylmethane diisocyanate (hereinafter 2,4′-MDI). ), 2,2′-diphenylmethane diisocyanate (hereinafter 2,2′-MDI), and the like, and polyphenylene polymethylene polyisocyanate (hereinafter P-MDI) such as diphenylmethane diisocyanate (hereinafter P-MDI) are used as isocyanate sources.
  • 4,4′-MDI 4,4′-diphenylmethane diisocyanate
  • 2,4′-MDI 2,4′-diphenylmethane diisocyanate
  • 2,2′-MDI 2,2′-diphenylmethane diisocyanate
  • P-MDI polyphenylene polymethylene polyis
  • various modified products such as MDI, a mixture of MDI and P-MDI, a urethane-modified product, a urea-modified product, an allophanate-modified product, and a burette-modified product can also be used.
  • the MDI content according to the present invention is in the range of 50 to 80% by mass.
  • the MDI content exceeds 80% by mass, the storage stability of the polyisocyanate composition obtained at low temperatures and the durability of the resulting flexible foam are lowered.
  • the amount is less than 50% by mass, the elongation of the flexible polyurethane foam decreases with an increase in the crosslinking density, and sufficient foam strength cannot be obtained.
  • the sum of the content ratio of 2,2'-MDI and the content ratio of 2,4'-MDI (hereinafter referred to as isomer content ratio) with respect to the total amount of MDI is 10 to 50 mass%.
  • the storage stability at low temperatures of the resulting polyisocyanate composition is impaired, Regular heating in the piping and foam molding machine is required.
  • the molding stability of the flexible polyurethane foam is impaired, and foam collapse or the like occurs during foaming.
  • it exceeds 50% by mass the reactivity is lowered and the molding cycle is extended, and the foam has a high foaming rate and shrinks after molding.
  • urethanization catalysts known in the art can be used.
  • amine catalysts having active hydrogen such as N, N-dimethylethanolamine and N, N-diethylethanolamine
  • the addition amount of the catalyst is preferably 0.01 to 10% by mass with respect to the polyol (A). If it is less than the lower limit, curing tends to be insufficient, and if it exceeds the upper limit, moldability may deteriorate.
  • a normal surfactant is used, and an organosilicon surfactant can be suitably used.
  • an organosilicon surfactant can be suitably used.
  • the amount of the foam stabilizer is preferably 0.1 to 3% by mass with respect to the polyol (A) including the polyol (A-1).
  • water is mainly used. Water generates carbon dioxide gas by reaction with an isocyanate group, and can foam. Moreover, you may use arbitrary foaming agents in addition to water. For example, a small amount of a low-boiling organic compound such as cyclopentane or isopentane may be used in combination, or air, nitrogen gas or liquefied carbon dioxide may be mixed and dissolved in the stock solution using a gas loading device and foamed. The amount of foaming agent added depends on the set density of the resulting product.
  • a low-boiling organic compound such as cyclopentane or isopentane
  • air nitrogen gas or liquefied carbon dioxide
  • crosslinking agents such as low molecular amino alcohols
  • fillers such as calcium carbonate and barium sulfate, flame retardants, plasticizers, colorants, antifungal agents, etc.
  • flame retardants such as calcium carbonate and barium sulfate
  • plasticizers such as calcium carbonate and barium sulfate
  • colorants such as colorants, antifungal agents, etc.
  • auxiliaries can be used as necessary.
  • the flexible polyurethane foam of the present invention is produced by reacting and foaming a mixed liquid of a polyol (A), a hindered phenol compound (B), a polyisocyanate (C), a catalyst, a foam stabilizer, and a foaming agent.
  • the molar ratio (NCO / active hydrogen) in the mixed foaming of all isocyanate groups in the polyisocyanate composition of the present invention and all active hydrogen groups in the active hydrogen group-containing compound containing water is 0.7 to 1.4.
  • the NCO INDEX is less than 70, the durability is lowered and the foaming property is excessively increased. If the NCO INDEX is higher than 120, the unreacted isocyanate remains for a long time, and the molding cycle is prolonged. Cell collapse may occur.
  • a foaming stock solution of the polyol (A), hindered phenol compound (B), polyisocyanate component (C), catalyst, foam stabilizer, and foaming agent is used in the mold.
  • the mold temperature at the time of pouring the foaming stock solution into the mold is usually 30 to 80 ° C., preferably 45 to 65 ° C.
  • the mold temperature at the time of pouring the foaming stock solution into the mold is less than 30 ° C., it leads to the extension of the production cycle due to a decrease in the reaction rate.
  • the temperature is higher than 80 ° C., the reaction between the polyol and the isocyanate Foam may collapse in the middle of foaming due to excessive acceleration of the reaction between water and isocyanate.
  • the curing time when foaming and curing the above foaming stock solution is preferably 10 minutes or less, more preferably 7 minutes or less in consideration of the production cycle of a general flexible mold foam.
  • the above-described components can be mixed using a high-pressure foaming machine, a low-pressure foaming machine, or the like, as in the case of a normal soft mold foam.
  • the isocyanate component and the polyol component immediately before foaming.
  • Other components can be mixed in advance with an isocyanate component or a polyol component as long as they do not affect the storage stability of the raw materials and the change over time of the reactivity. These mixtures may be used immediately after mixing or may be used in appropriate amounts after storage.
  • a foaming apparatus capable of simultaneously introducing more than two components into the mixing part, polyols, foaming agents, isocyanates, catalysts, foam stabilizers, additives and the like can be individually introduced into the mixing part.
  • the mixing method may be either dynamic mixing in which mixing is performed in the machine head mixing chamber of the foaming machine or static mixing in which mixing is performed in the liquid feeding pipe, or both may be used in combination.
  • Mixing of a gaseous component such as a physical foaming agent and a liquid component is often performed by static mixing, and mixing of components that can be stably stored as a liquid is often performed by dynamic mixing.
  • the foaming apparatus used in the present invention is preferably a high-pressure foaming apparatus that does not require solvent cleaning of the mixing part.
  • the mixed liquid obtained by such mixing is discharged into a mold (mold), foamed and cured, and then demolded.
  • a release agent to the mold in advance.
  • a release agent usually used in the field of molding processing may be used.
  • the product after demolding can be used as it is, but it is preferable to stabilize the appearance and dimensions of the subsequent product by destroying the cell membrane of the foam under compression or reduced pressure by a conventionally known method.
  • Elongation retention before and after heat test (%) Elongation before heat test (%) / Elongation after heat test (%) ⁇ 100 [Preparation of polyol premix] (Polyol premix preparation example) After the reactor equipped with a stirrer, a cooling pipe, a nitrogen introducing pipe, and a thermometer was purged with nitrogen, 90 g of polyol 1, 10 g of polyol 2 (castor oil-based polyol), and 0 of additive 1 (hindered phenol-based compound) .6 g, catalyst 1 0.71 g, catalyst 2 0.1 g, foam stabilizer 1 0.5 g, and water 2 g were charged and stirred at 23 ° C. for 0.5 hours to obtain a polyol premix (P- 1) was obtained. Other polyol premixes (P-2 to P-15) were prepared in the same manner as P-1. The results are shown in Tables 1 and 2.
  • Examples 1 to 9, Comparative Examples 1 to 11 Among the raw materials shown in Tables 3 to 6, the liquid temperature of the mixture of all raw materials other than the polyisocyanate compound (polyol premix) is adjusted to 24 ° C to 26 ° C, and the polyisocyanate component is adjusted to the liquid temperature of 24 ° C to 26 ° C. did. A predetermined amount of polyisocyanate component is added to the polyol premix, mixed for 7 seconds with a mixer (7000 rpm), poured into a mold to foam a flexible polyurethane foam, and then taken out of the mold, the resulting soft The physical properties of the polyurethane foam were measured.
  • NCO Index is the ratio of NCO groups to the number of active hydrogen atoms present in the formulation.
  • Mold temperature 60 ⁇ 65 °C Mold shape: 400mm ⁇ 400mm ⁇ 10mm Mold material: Aluminum cure Conditions: 60-65 ° C x 5 minutes
  • Polyol 2 unrefined castor oil having an average functional group number of 2.7 and a hydroxyl value of 160 (mgKOH / g), URIC H-24 manufactured by Ito Oil Co., Ltd.
  • Additive 1 Irganox 1135 (Irganox 1135: benzenepropanoic acid, 3,5-bis (1,1-dimethylethyl) -4-hydroxy, C7-C9 side chain alkyl ester, manufactured by BASF Japan), hindered phenol Compound / additive 2: Sumilizer TP-D (SUMILIZER TP-D, manufactured by Sumitomo Chemical Co., Ltd.), sulfur compound / additive 3: Irgafos 168 (Irgafos 168: Tris (2,4-di-t-butylphenyl) phos Fight, manufactured by BASF Japan), phosphorus compound / catalyst 1: 33% dipropylene glycol solution of triethylenediamine, TEDA-L33 manufactured by Tosoh Corporation Catalyst 2: 70% dipropylene glycol solution of bis (2-dimethylaminoethyl) ether, TOYOCAT ET manufactured by Tosoh Corporation
  • Table 5 shows the measurement of physical properties of a flexible polyurethane foam produced by adding a sulfur compound (additive 2) and a phosphorus compound (additive 3) in addition to a hindered phenol compound (additive 1) as an additive. It is a result. As shown in Comparative Examples 5 to 6, when each additive other than the hindered phenol compound was used, sufficient heat resistance was not obtained.

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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)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention fournit une mousse polyuréthane souple d'une excellente résistance à la chaleur qui est mise en œuvre dans un tapis chauffant, un matériau antivibration/aintibruit d'une génératrice à l'intérieur d'un compartiment moteur de véhicule, ou similaire. La composition pour moulage de mousse polyuréthane souple de l'invention est caractéristique en ce qu'elle comprend dans un polyol 10 à 50% en masse d'au moins une sorte de polyol choisi dans un groupe constitué d'une huile de ricin et d'un polyol modifié par une huile de ricin, elle comprend 0,1 à 5% en masse par rapport au polyol d'un composé à base de phénol encombré, elle contient en tant que polyisocyanate un MDI dans une plage de 50 à 80% en masse, et elle contient 10 à 50% en masse par rapport à la masse totale de MDI susmentionné d'un ２，２'－ＭＤＩ et d'un ２，４'－ＭＤＩ contenus dans le MDI susmentionné.
PCT/JP2017/008925 2016-03-11 2017-03-07 Composition pour moulage de mousse polyuréthane souple Ceased WO2017154878A1 (fr)

Applications Claiming Priority (2)

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JP2016048530A JP6903870B2 (ja) 2016-03-11 2016-03-11 軟質ポリウレタンフォーム成型用組成物
JP2016-048530 2016-03-11

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CN110760054A (zh) * 2019-10-17 2020-02-07 刘鹏 一种抗冲击保温隔音板的制备方法
US20210197424A1 (en) * 2017-11-08 2021-07-01 Basf Se Vegetable oil as foam stabilizer in pu boots manufacturing

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CN111909345B (zh) * 2020-08-13 2022-05-20 淄博正大聚氨酯有限公司 一种床垫用聚氨酯高回弹绵及其制备方法
JP2023132811A (ja) * 2022-03-11 2023-09-22 東ソー株式会社 軟質ポリウレタンフォーム

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JP2005206709A (ja) * 2004-01-23 2005-08-04 Inoac Corp ポリウレタンフォームの製造方法
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JP2006070241A (ja) * 2004-08-04 2006-03-16 Tokai Rubber Ind Ltd 車両用難燃性防音・防振材及びその製造方法
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Publication number Priority date Publication date Assignee Title
US20210197424A1 (en) * 2017-11-08 2021-07-01 Basf Se Vegetable oil as foam stabilizer in pu boots manufacturing
US11872728B2 (en) * 2017-11-08 2024-01-16 Basf Se Vegetable oil as foam stabilizer in PU boots manufacturing
CN110760054A (zh) * 2019-10-17 2020-02-07 刘鹏 一种抗冲击保温隔音板的制备方法

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