WO2008012908A1 - Procédé de fabrication de mousse de polyuréthane - Google Patents

Procédé de fabrication de mousse de polyuréthane Download PDF

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Publication number
WO2008012908A1
WO2008012908A1 PCT/JP2006/314948 JP2006314948W WO2008012908A1 WO 2008012908 A1 WO2008012908 A1 WO 2008012908A1 JP 2006314948 W JP2006314948 W JP 2006314948W WO 2008012908 A1 WO2008012908 A1 WO 2008012908A1
Authority
WO
WIPO (PCT)
Prior art keywords
polyurethane foam
polyol
foam
mass
mdi
Prior art date
Application number
PCT/JP2006/314948
Other languages
English (en)
Japanese (ja)
Inventor
Suguru Yamada
Naoyuki Ohmori
Kohji Yoshida
Hitoshi Yaguchi
Original Assignee
Nippon Polyurethane Industry Co., 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 Nippon Polyurethane Industry Co., Ltd filed Critical Nippon Polyurethane Industry Co., Ltd
Priority to CNA2006800554985A priority Critical patent/CN101501095A/zh
Priority to PCT/JP2006/314948 priority patent/WO2008012908A1/fr
Publication of WO2008012908A1 publication Critical patent/WO2008012908A1/fr

Links

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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
    • C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
    • C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
    • C08J9/122—Hydrogen, oxygen, CO2, nitrogen or noble gases
    • 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
    • C08G2101/00—Manufacture of cellular products
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes

Definitions

  • the present invention relates to a method for producing a polyurethane foam having excellent durability and the like by a mechano-calfloss method.
  • Polyurethane foams by the mecha-calfloss method are used in rolls for copying machines, cosmetic puffs, carpets, packing, sealing materials, vibration damping materials, vibration damping materials, and the like.
  • Various manufacturing methods such as the methods described in Patent Document 1 and Patent Document 2 have been proposed as a method for manufacturing a polyurethane foam by the mecha-calfs method.
  • Patent Document 1 Japanese Patent Laid-Open No. 2001-89547
  • Patent Document 2 Japanese Patent Laid-Open No. 10-258437
  • Patent Document 1 uses a foam stabilizer! /, So there is little problem of bleeding in the polyurethane foam obtained.
  • the cell state of the polyurethane foam cells is uneven in cell size, and the hardness varies depending on the part.
  • the manufacturing method of Patent Document 2 uses an alcohol-modified silicone oil and is subjected to centrifugal molding, so that a foam with few pinholes can be obtained.
  • the molded product is thin, and is not suitable for molding block-like or thick products.
  • polyurethane foam As the polyols used in polyurethane foam, poly (oxytetramethylene) polyol (hereinafter abbreviated as “PTMG”) is derived from poly (oxypropylene) polyol (hereinafter abbreviated as “PPG”). Polyurethane foams with excellent physical properties such as mechanical strength, durability and impact resilience tend to be obtained.
  • PTMG poly (oxytetramethylene) polyol
  • PPG poly (oxypropylene) polyol
  • the present invention relates to a method for producing a polyurethane foam by the mecha-calfloss method. Compared with the conventional polyurethane foam by the mecha-calfloss method, a highly durable polyurethane foam can be obtained.
  • An object of the present invention is to provide a method for producing a polyurethane foam having higher durability than that obtained by the conventional mechanical calfloss method.
  • the present invention has been found as a result of intensive studies to solve the above-described problems, that is, organic polyisocyanate (A), polyol (B), catalyst (C), and
  • organic polyisocyanate (A), polyol (B), catalyst (C) and
  • the polyurethane foam-forming composition in which the foam stabilizer (D) is dispersed and mixed is further mixed and dispersed with an inert gas by mechanical stirring, followed by foam curing.
  • the content of PTMG component in the obtained polyurethane foam is 50 to 80% by mass
  • Dimethylpolysiloxane polyether block copolymer having a polyether content of 5 to 20% by mass of the foam stabilizer (D), a terminal alkyl group, and a number average molecular weight of 1,000 to 2,000.
  • a method for producing the polyurethane foam which is a coalescence.
  • the present invention also relates to an isocyanate group-terminal prepolymer obtained by reacting an organic polyisocyanate (A) force diphenylmethane diisocyanate (I) and PTMG (mouth). ) Force The process for producing polyurethane foam as described above, which comprises 70 to 90% by mass of PTMG (mouth).
  • the present invention relates to a method for producing a polyurethane foam by mecha-calfloss method using PTMG as a main polyol.
  • the main polyol of the polyurethane foam is defined as PTMG having a “PTMG component content” of 50 to 80% by mass.
  • polyurethane foam is subjected to Colisch decomposition to recover PTMG, and as shown by the following formula, polyurethane before decomposition is recovered. It can be determined by the ratio of PTMG recovery to foam
  • the organic polyisocyanate (A) used in the present invention is diphenylmethane diisocyanate (hereinafter abbreviated as “MDI”), polyphenylene-polymethylene polyisocyanate (hereinafter referred to as “MDI”).
  • MDI diphenylmethane diisocyanate
  • MDI polyphenylene-polymethylene polyisocyanate
  • MDI polynuclear condensate Abbreviated as “MDI polynuclear condensate”), tolylene diisocyanate, xylylene diisocyanate, tetramethylxylylene diisocyanate, isophorone diisocyanate, hexamethylene diisocyanate, naphthalene diene Isocyanates, hydrogenated cardimethane methane diisocyanates, hydrogenated xylylene diisocyanates, etc., and some of the isocyanate groups of compounds having these isocyanate groups are urethane, biuret, allophanate, carbodiene. For imide, uretonimine, oxazolidone, amide, imide, isocyanurate, uretdione, etc. Denatured ones are mentioned. These can be used alone or in combination of two or more as required.
  • MDI consists of 4,4'-dimethanemethane diisocyanate (hereinafter abbreviated as 4,4'-MDI), 2,4'-dimethanemethane diisocyanate (hereinafter, 2,4 ').
  • 4,4'-MDI 4,4'-dimethanemethane diisocyanate
  • 2,4 ' 2,4'-dimethanemethane diisocyanate
  • 2, 2 ′ diphenylmethane diisocyanate
  • the MDI-based polynuclear mixture exists in the form of a mixture of compounds having three or more benzene rings to which isocyanate groups are bonded in one molecule and having different degrees of condensation. Usually, it is not supplied in the form of an MDI-based multinuclear mixture alone, but is supplied in the form of a mixture with MDI (a mixture of MDI and an MDI-based multinuclear mixture is abbreviated as “polymeric MDI”).
  • polymeric MDI is obtained by converting an amino group to an isocyanate group by phosgene, etc., from a condensed mixture (polyamine) obtained by the condensation reaction of aline and formalin.
  • the product is an MDI polynuclear mixture with a different degree of condensation from MDI.
  • the composition of MDI and polymeric MDI can be changed by changing the raw material composition ratio and reaction conditions during condensation, or by removing a portion of MDI by distillation.
  • the MDI content of polymeric MDI and the isomer composition ratio of MDI can be determined from the calibration curve force based on the area percentage of each peak obtained by gel permeation chromatography or gas chromatography.
  • the 4,4'-MDI content is 50% by mass or more, 4, 4 'polymeric MDI to MDI content containing MDI which is 50-100 mass 0/0, and the mixing ratio and heating conditions etc. during these Isoshianeto group-terminated urethane Prevost Rimmer preferred instrument actual forming shape
  • isocyanate group-terminated urethane prepolymers are preferred.
  • an organic diisocyanate (the above-mentioned MDI is particularly preferred) and a polymer polyol described below are reacted in an atmosphere having an excess of isocyanate groups.
  • the reaction temperature is preferably 50 to: LOO ° C.
  • the blending ratio of organic polyisocyanate (A) and polyol) is almost the same, and considering the viscosity of isocyanate-terminated prepolymers, the isocyanate content is preferably 5 to 35% by weight, especially 8 to 15% by weight. Is preferred.
  • the organic diisocyanate Z polymer polyol 20Z80 to 50Z50 (mass ratio) is preferable as the blending ratio of the organic diisocyanate and the polymer polyol in the production of the isocyanate group-terminated polymer.
  • the high molecular polyol in the isocyanate group-terminated prepolymer is desirably PTMG.
  • the polyol ( ⁇ ) used in the present invention comprises a polymer polyol and a chain extender.
  • the polymer polyol means a polyol having a number average molecular weight of 500 or more
  • the chain extender means a polyol having a number average molecular weight of less than 500.
  • polymer polyol examples include polyether polyol, polyester polyol, polycarbonate polyol, and hydrophobic polyol.
  • Preferred polymer high-molecular weight ⁇ Number average molecular weight is 1,000 to 10,000, and 1,500 to 5,000 power is particularly preferred. If the number average molecular weight is too high, the foam hardness will tend to be too low. If the number average molecular weight is too small, the elasticity of the foam tends to be impaired.
  • polyether polyols examples include propylene glycol and ethylene glycol. , Glycerin, trimethylolpropane, hexanetriol and the like as starting materials, and those obtained by addition polymerization of alkylene oxide and those obtained by ring-opening addition of a low molecular cyclic ether.
  • Polyester polyols include condensed polyester polyols obtained by condensation of dicarboxylic acids and diols, triols, etc., latatone polyester polyols obtained by ring-opening polymerization of latatones based on diols and triols, and polyether polyols. Polyols such as ester-modified polyol ester-modified with rataton are preferably used.
  • polycarbonate polyol examples include those obtained by a transesterification reaction between a low molecular polyol such as butanediol or hexanediol and a low molecular carbonate such as propylene carbonate or jetyl carbonate.
  • a low molecular polyol such as butanediol or hexanediol
  • a low molecular carbonate such as propylene carbonate or jetyl carbonate.
  • hydrophobic polyol polyisoprene polyol, polybutadiene polyol, hydrogenated polybutadiene polyol and the like are used.
  • polymer polyol components may be used alone or in combination of two or more.
  • the polymer polyol in the polyol (B) preferably contains 70 to 95% by mass of PTMG. Further, the polyol used in combination with PTMG is preferably terminal EO-treated PPG.
  • chain extender examples include ethylene glycol, propylene glycol, 1,4 butane diol, trimethylol propane, tetramethylene ether glycol, polyethylene glycol and the like. These chain extenders may be used alone or in combination of two or more.
  • 1,4 butanediol is preferred. This is because 1,4-butanediol has a primary hydroxyl group and therefore has good reactivity, is liquid at room temperature, has excellent workability, has an appropriate molecular weight, and has excellent mechanical strength. Is obtained.
  • Examples of the catalyst (C) used in the present invention include monoamines such as triethylamine and dimethylcyclohexylamine, and diamines such as tetramethylethylenediamine, tetramethylpropanediamine and tetramethylhexanediamine.
  • Pentamethyljetylenetriamine Triamines such as pentamethyldipropylenetriamine and tetramethyldardine, cyclic diamine, dimethylbiperazine, methylethylbiperazine, methylmorpholine, dimethylaminoethylmorpholine, dimethylimidazole and other cyclic amines, dimethyl Alcoholamines such as aminoethanol, dimethylaminoethoxyethanol, trimethylaminoethylethanolamine, methylhydroxyethylpiperazine, hydroxyethylmorpholine, bis (dimethylaminoethyl) ether, ethylene glycol bis (dimethyl) aminopropyl pills Ether amines such as ethers, stannous octoate, dibutyltin diacetate, dibutyltin dilaurate, dibutinoletin marker peptide, dibutinoletin tiocanoloxylate, Buchin
  • the foam stabilizer (D) used in the present invention is a dimethylpolysiloxane polyetherpolyol block copolymer having a content of 5 to 20% by mass, an alkyl group at the end, and a number average. It has a feature of having a polyether part having a molecular weight of 1,000 to 2,000.
  • the content of silicon is measured by an ashing method, specifically, by the following procedure.
  • the number average molecular weight of the polyether part of the foam stabilizer (D) can be determined by GPC measurement of the foam stabilizer by Colisch decomposition.
  • the present invention can also use other conventionally known additives as required, for example, an antioxidant, an ultraviolet absorber, a flame retardant, a colorant, a conductive agent, an insulating agent, and a luminescent agent. And antibacterial agents and fragrances.
  • the polyisocyanate component, polyol component, catalyst, and other additives stored or prepared in separate containers. Is added to one mixing head while mixing an inert gas, mixed so that it is homogeneous, and the mixed solution is flowed on a conveyor on which a formwork and a bottom paper are laid, and is heated and cured, or the mixed solution is For example, a method of casting in a predetermined mold or the like and curing by heating.
  • the foam obtained by such a method is a polyurethane foam having uniform fine cells and appropriate hardness.
  • the isocyanate index (isocyanate group Z active hydrogen group X 100) at this time is preferably 50 to 150, more preferably 60 to 120. If the index is too low, the foam surface will tend to stick. Also, if the index is too high, it may not foam, or it may collapse and a flexible foam may not be obtained.
  • the polyurethane foam thus obtained becomes a foam having a uniform and fine cell with a density of 0.3 to 0.9 gZcm 3 .
  • the polyurethane foam obtained by the present invention includes various rolls such as toner conveying rolls, transfer rolls, charging rolls and developing rolls of electrophotographic apparatuses, bedding such as pillows and mattresses, cosmetic puffs, packings, sealing materials, and carpets. Used in the fields of backing, vibration control materials, seismic isolation materials, vibration isolation materials, sound insulation materials, etc.
  • the present invention will be described in more detail with reference to Examples, but the present invention is not limited thereto.
  • the ratio is quality. It is a quantity ratio, and “%” is “mass%”.
  • Table 1 shows the results of the measurement of the number average molecule of the content, the terminal group, and the polyether part of the foam stabilizers 1 to 4.
  • the recovered material was measured by GPC-IR after decomposition with Kollisch.
  • X20—1749 Silicone foam stabilizer made by Shin-Etsu Chemical Co., Ltd.
  • MDI Diphenylmethane diisocyanate
  • a polyol premix OH-1 was prepared by charging the 2 L reactor shown in Table 2.
  • Liquid temperature: 40 ° C polyol premix OH-1 and liquid temperature: 40 ° C polyisocyanate NCO-1 were mixed in the proportions shown in Table 4 and stirred for 1 minute to dry air Pour the mixed solution with the mixture into a mold (10cm x 10cm x 10cm, open top), then leave the mold filled with the mixed solution in a hot air oven adjusted to 120 ° C for 30 minutes, The foamed polyurethane raw material was cured. Polyurethane foam was produced by removing the mold force from the cured polyurethane foam.
  • a polyurethane foam was produced in the same procedure as in Example 1 with the formulation shown in Table 3.
  • the evaluation items and measurement method of the foam are as follows.
  • Polyurethane foam was decomposed by Kolisch decomposition to recover PTMG, and the ratio of recovered PTMG to polyurethane foam before decomposition was calculated. Density and hardness:
  • Example 1 The number of cells existing on three arbitrarily selected cut surfaces was measured, and expressed as a relative ratio when Example 1 was set to 1.
  • the polyurethane foam obtained by the present invention has uniform fine cells and has a low density.
  • the bubble formation was not successful and the density was increased, or the bubble itself was not sufficiently formed.

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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)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

La présente invention a pour objectif de proposer un procédé permettant d'obtenir une mousse de polyuréthane présentant une durabilité supérieure à celle d'une mousse classique obtenue par un procédé de moussage mécanique. L'invention concerne un procédé de fabrication d'une mousse de polyuréthane comportant les étapes consistant à mélanger (A) un polyisocyanate organique, (B) un polyol, (C) un catalyseur et (D) un agent de contrôle de la mousse dans un état dispersé pour donner une composition de formation de mousse de polyuréthane ; à mélanger un gaz inerte avec la composition dans un état dispersé par une agitation mécanique ; à faire mousser le mélange résultant, puis à faire durcir le produit moussé, la mousse de polyuréthane ayant une teneur en poly(oxytétraméthylène) polyol de 50 à 80 % en masse, et l'agent de contrôle de la mousse (D) étant un copolymère à blocs diméthylpolysiloxane-polyéther dont la teneur en silicium est de 5 à 20 % en masse, présente une fraction polyéther incluant un groupe alkyle à son extrémité terminale, et présentant une masse moléculaire moyenne en nombre de 1000 à 2000.
PCT/JP2006/314948 2006-07-28 2006-07-28 Procédé de fabrication de mousse de polyuréthane WO2008012908A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CNA2006800554985A CN101501095A (zh) 2006-07-28 2006-07-28 聚氨酯泡沫体的制造方法
PCT/JP2006/314948 WO2008012908A1 (fr) 2006-07-28 2006-07-28 Procédé de fabrication de mousse de polyuréthane

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/JP2006/314948 WO2008012908A1 (fr) 2006-07-28 2006-07-28 Procédé de fabrication de mousse de polyuréthane

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WO2008012908A1 true WO2008012908A1 (fr) 2008-01-31

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014137238A (ja) * 2013-01-15 2014-07-28 Toyo Tire & Rubber Co Ltd センサ
EP3064532A1 (fr) 2015-03-03 2016-09-07 Evonik Degussa GmbH Fabrication de couches polyuréthane poreuses
CN113801293A (zh) * 2021-08-13 2021-12-17 浙江工业大学 利用聚氨酯泡沫降解产物制备耐高温发泡胶的方法

Families Citing this family (6)

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Publication number Priority date Publication date Assignee Title
CN101696280B (zh) * 2009-10-23 2011-07-20 河南科达节能环保有限公司 一种无氟聚氨酯发泡成型工艺
CN103467970A (zh) * 2013-09-06 2013-12-25 惠州市远安新材料有限公司 一种基于聚氨酯应用的粉扑
EP3538593A4 (fr) * 2016-11-14 2020-07-15 Covestro Deutschland AG Mousse de polyuréthane destinée à être utilisée dans des applications cosmétiques
TWI756292B (zh) 2016-11-14 2022-03-01 德商麥克專利有限公司 具有受體基團與供體基團之化合物
CN108623774A (zh) * 2017-03-22 2018-10-09 洛阳尖端技术研究院 一种石墨烯聚氨酯泡沫复合材料及其制备方法
CN115315457A (zh) * 2020-03-27 2022-11-08 阿基里斯株式会社 聚氨基甲酸酯泡沫以及鞋底构件

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JPH09278856A (ja) * 1996-04-12 1997-10-28 Bridgestone Corp ウレタンフォーム製造用組成物、弾性材料及び弾性部材
JP2005120275A (ja) * 2003-10-17 2005-05-12 Nippon Polyurethane Ind Co Ltd 軟質ポリウレタンフォームの製造方法
JP2005227392A (ja) * 2004-02-10 2005-08-25 Inoac Corp シール部材およびその製造方法
JP2005338460A (ja) * 2004-05-27 2005-12-08 Bridgestone Corp 導電性弾性部材及びそれを用いた画像形成装置

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JPH09278856A (ja) * 1996-04-12 1997-10-28 Bridgestone Corp ウレタンフォーム製造用組成物、弾性材料及び弾性部材
JP2005120275A (ja) * 2003-10-17 2005-05-12 Nippon Polyurethane Ind Co Ltd 軟質ポリウレタンフォームの製造方法
JP2005227392A (ja) * 2004-02-10 2005-08-25 Inoac Corp シール部材およびその製造方法
JP2005338460A (ja) * 2004-05-27 2005-12-08 Bridgestone Corp 導電性弾性部材及びそれを用いた画像形成装置

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014137238A (ja) * 2013-01-15 2014-07-28 Toyo Tire & Rubber Co Ltd センサ
EP3064532A1 (fr) 2015-03-03 2016-09-07 Evonik Degussa GmbH Fabrication de couches polyuréthane poreuses
CN113801293A (zh) * 2021-08-13 2021-12-17 浙江工业大学 利用聚氨酯泡沫降解产物制备耐高温发泡胶的方法

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