WO2010140356A1 - ポリウレタン発泡組成物およびポリウレタンフォームの製造方法 - Google Patents
ポリウレタン発泡組成物およびポリウレタンフォームの製造方法 Download PDFInfo
- Publication number
- WO2010140356A1 WO2010140356A1 PCT/JP2010/003677 JP2010003677W WO2010140356A1 WO 2010140356 A1 WO2010140356 A1 WO 2010140356A1 JP 2010003677 W JP2010003677 W JP 2010003677W WO 2010140356 A1 WO2010140356 A1 WO 2010140356A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- polyurethane foam
- crosslinking agent
- integer
- acid
- Prior art date
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
- C08G18/30—Low-molecular-weight compounds
-
- 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
- C08G18/3271—Hydroxyamines
- C08G18/3275—Hydroxyamines containing two hydroxy 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
- C08G18/28—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
- C08G18/302—Water
-
- 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
-
- 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
- C08G18/3271—Hydroxyamines
- C08G18/3296—Hydroxyamines being in latent form
-
- 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
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
- C08G18/348—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
- 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
- C08G18/3893—Low-molecular-weight compounds having heteroatoms other than oxygen containing silicon
-
- 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
- C08G18/4833—Polyethers containing oxyethylene units
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
-
- 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
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
-
- 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
-
- 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
- C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
-
- 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
-
- 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
- C08J9/0014—Use of organic additives
- C08J9/0042—Use of organic additives containing silicon
-
- 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
- C08J9/125—Water, e.g. hydrated salts
-
- 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
-
- 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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2110/00—Foam properties
- C08G2110/0008—Foam properties flexible
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0041—Foam properties having specified density
- C08G2110/005—< 50kg/m3
-
- 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
- C08G2110/00—Foam properties
- C08G2110/0083—Foam properties prepared using water as the sole blowing agent
Definitions
- the present invention relates to a polyurethane foam composition and a method for producing a polyurethane foam, and more particularly to a foam composition for molding a polyurethane foam containing a specific crosslinking agent and a method for producing a flexible polyurethane foam using the foam composition. .
- Soft polyurethane foam is widely used for vehicle cushioning materials, furniture mats, bedding, miscellaneous goods, etc. due to its high cushioning properties.
- a flexible polyurethane foam is usually obtained by reacting an organic polyisocyanate and two or more compounds containing active hydrogen (usually containing water) in the presence of a catalyst, a foam stabilizer, and other additives.
- active hydrogen-containing compound include polyols, polymer polyols obtained by radical polymerization of acrylonitrile and styrene in polyols, primary and secondary polyamines, and water.
- starting materials are mixed with a high-pressure foaming machine, injected into a mold, molded, and then the foamed cells in the foam are forcibly connected using a compressor.
- the method of generalization is taken.
- the crosslinking agent which is one of the additives, has a function of increasing the foam stability by reacting with the isocyanate to increase the molecular weight.
- an amine-based crosslinking agent in the production of polyurethane foam.
- a method for producing a polyurethane foam using alkanolamine as a crosslinking agent has been proposed (see Patent Document 1).
- this method improves foaming reactivity, but as the reactivity increases, the rate of viscosity increase also increases, reducing the flowability immediately after pouring into the mold and reducing the foam composition to the details of the mold. There was a problem that the reaction progressed before it spread and the defect rate increased.
- Patent Document 2 describes that cell communication is performed at a low pressure during compression after demolding, and an open cell (cell communication in foam) effect is realized.
- this method has a problem that, when the density is lowered, sufficient hardness as a high resilience polyurethane foam cannot be obtained.
- the present invention has been made to solve such a problem, and can obtain a flexible polyurethane foam having improved physical properties such as hardness. Further, in the production, the reaction can be performed without reducing the final reactivity.
- An object of the present invention is to provide a polyurethane foam composition capable of delaying the above, suppressing an increase in viscosity during the reaction immediately after mold injection, and achieving a low pressure during cell communication using a compressor.
- the polyurethane foam composition of the present invention comprises (A) a polyisocyanate, (B) (B1) a polyol and (B2) an active hydrogen-containing compound each containing water, and (C) a crosslinking agent composition as the component (B).
- the polyurethane foam composition contains 0.1 to 20 parts by mass with respect to 100 parts by mass of the active hydrogen-containing compound, and the (C) crosslinking agent composition has the formula (1): H x R 1 y N ((R 2 O) n H) 3-xy (1) (wherein R 1 is a hydrocarbon group selected from an alkyl group having 1 to 12 carbon atoms, an aryl group or an aralkyl group, R 2 represents an alkyl group having 2 to 4 carbon atoms, x is an integer of 0 to 2, y is an integer of 0 to 2, x + y is an integer of 0 to 2, and n is an integer of 1 to 10.
- C1 crosslinking agent selected from aminosilane (b) represented by formula (3): X z -R 8 (COOH) m.
- R 8 is a hydrocarbon group
- X is a group selected from a chlorine group, a fluorine group, a bromine group, and a hydroxyl group.
- Z is an integer of 1 or more
- m is an integer of 1 or more.
- C2 represented by the formula (C) in the crosslinking agent composition (C).
- C1 is the content of the crosslinking agent (moles)
- said (C2) is greater than the content of the carboxylic acid (moles).
- the method for producing a polyurethane foam according to the present invention is characterized by using the polyurethane foam composition described above.
- the hardness of the foam (foam) can be reduced without causing a decrease in physical properties (for example, compression residual strain, wet heat aging test, tear strength, elongation at break, rebound resilience). Can be improved.
- the reaction immediately after mold injection is delayed to suppress the increase in viscosity, and the pressure can be reduced when the cells are connected by a compressor. Can do. Therefore, in the production of polyurethane foam, particularly flexible polyurethane foam, it is possible to greatly improve the production efficiency and obtain a product with good characteristics.
- the polyurethane foam composition of the embodiment of the present invention contains (A) a polyisocyanate, (B) (B1) a polyol and (B2) an active hydrogen-containing compound containing water, and (C) a crosslinking agent composition.
- A a polyisocyanate
- B1 a polyol
- B2 an active hydrogen-containing compound containing water
- C a crosslinking agent composition.
- polyisocyanate As the polyisocyanate as component (A), known aliphatic, alicyclic and aromatic organic isocyanate compounds having two or more isocyanate groups can be used. For example, hexamethylene diisocyanate, isophorone diisocyanate, 4,4-dicyclohexylmethane diisocyanate, 2,4- or 2,6-tolylene diisocyanate (toluene diisocyanate or toluidine diisocyanate: TDI), 2,2'- or 2,4- or Examples include alkylene diisocyanates or arylene isocyanates such as 4,4′-diphenylmethane diisocyanate (MDI), and known triisocyanates and polymeric MDIs (crude diphenylmethane diisocyanate; referred to as crude MDI).
- MDI 4,4′-diphenylmethane diisocyanate
- crude MDI crude MDI
- Suitable isocyanates for obtaining flexible foams are usually a mixture of 80% by weight 2,4-TDI and 20% by weight 2,6-TDI, 65% by weight 2,4-TDI and 35% by weight 2 , 6-TDI, all MDI type polyisocyanates, and mixtures of TDI and MDI.
- the amount of polyisocyanate used in the production of foam (foam) is described as “Isocyanate Index”.
- the “isocyanate index” indicates the percentage of isocyanate groups relative to the active hydrogen-containing groups that can react with isocyanate groups, the theory required to react the actual amount of polyisocyanate used in the reaction mixture with all of the active hydrogens. Divided by the stoichiometric amount of polyisocyanate required and multiplied by 100.
- the index is not particularly limited, but is generally manufactured in the range of 70 to 130 in the manufacture of flexible foam.
- the active hydrogen-containing compound as component (B) contains (B1) polyol and (B2) water, respectively.
- the polyol is a compound having two or more active hydrogen-containing functional groups such as a hydroxyl group capable of reacting with the isocyanate group of the component (A) in the molecule, and known ones can be used.
- the number of the active hydrogen-containing functional group (hydroxyl group) of the polyol is preferably 2 to 8, and most preferably 2.3 to 6. If the number of hydroxyl groups is 2 or more, the durability of the flexible polyurethane foam will be good. In addition, by setting the average number of hydroxyl groups to 6 or less, the flexible polyurethane foam does not become too hard, and mechanical properties such as elongation become good.
- the compound having two or more hydroxyl groups include polyether polyols and polyester polyols.
- it is preferably composed of only one or more kinds of polyether-based polyols, or those based on polyether-based polyols and used in combination with polyester-based polyols, polyhydric alcohols, polyamines, alkanolamines, and other active hydrogen-containing compounds. .
- the polyol that can be used in the embodiment of the present invention is not particularly limited, but those classified below are preferably used alone or in combination. That is, 1) alkylene oxide adduct of polyhydroxyalkane 2) alkylene oxide adduct of non-reducing sugar and sugar derivative 3) alkylene oxide adduct of phosphoric acid and polyphosphoric acid 4) alkylene oxide adduct of polyphenols 5) primary and secondary It is an alkylene oxide adduct of amine.
- An alkylene oxide adduct of polyhydroxyalkane suitable for obtaining a flexible foam is an ethylene oxide adduct of trihydroxyalkane and a propylene oxide adduct.
- the grafted polyol or polymer polyol is one kind of polyol useful for the embodiment of the present invention, and can be used widely in the production of flexible foam.
- the polymer polyol is, for example, a polyol containing a stable dispersion of a polymer (for example, vinyl polymer fine particles) in the polyol of type 1) among the above polyols 1) to 5).
- (B1) polyol having a hydroxyl value of 10 to 120 mgKOH / g it is preferable to use (B1) polyol having a hydroxyl value of 10 to 120 mgKOH / g.
- the hydroxyl value By setting the hydroxyl value to 10 mgKOH / g or more, the viscosity of the polyol does not increase and the workability during production is good. Moreover, durability of a flexible polyurethane foam becomes favorable because a hydroxyl value shall be 120 mgKOH / g or less. It is preferable to select the hydroxyl value of the polyol according to the use of the polyurethane foam.
- polyols as the component (B1) include, for example, Sanniks FA-703 (glycerin-propylene oxide / ethylene oxide adduct, hydroxyl value 33 mgKOH / g; manufactured by Sanyo Chemical Industries, Ltd.) and Sanniks FA-728R.
- the water as component (B2) is blended as a chemical foaming agent, and foamed by carbon dioxide gas generated by the reaction between this (B2) water and the isocyanate group in the polyisocyanate as component (A).
- At least 50% of the gas volume forming foam ie, at least 50% by volume of the total foam gas is carbon dioxide produced by the reaction of water (B2) and the isocyanate groups of (A) polyisocyanate.
- water is used alone as a foaming agent, and that 100% of the foaming gas capacity is carbon dioxide produced by the reaction of water and isocyanate groups. That is, in addition to water that is a chemical foaming agent, a chemical foaming agent and a physical foaming agent that are organic acids such as formic acid can be used in combination, but it is more preferable to use water alone for foaming. .
- the crosslinking agent composition contains (a) at least one crosslinking agent (C1) selected from alkanolamine and (b) aminosilane, and at least one carboxylic acid (C2).
- (C1) The (a) alkanolamine which is a crosslinking agent is represented by the following formula (1). H x R 1 y N ((R 2 O) n H) 3-xy (1)
- R 1 represents an alkyl group having 1 to 12 carbon atoms, an aryl group, or a group selected from aralkyl groups
- R 2 represents an alkyl group having 2 to 4 carbon atoms.
- X is an integer from 0 to 2
- y is an integer from 0 to 2
- x + y is an integer from 0 to 2
- n is an integer from 1 to 10.
- two R 1 s may be the same or different.
- alkanolamine (a) examples include triethanolamine, triisopropanolamine, N-hexyldiethanolamine (N, N-diethanolhexylamine), N-methyldiethanolamine, diethanolamine, diisopropanolamine (N, N-diisopropanol). Amine), and their alkylene oxide adducts.
- a crosslinking agent (b) aminosilane is represented by the following formula (2). (R 3 O) q R 4 3-q Si—R 5 — (NHCH 2 CH 2 ) p NR 6 R 7 (2)
- R 3 represents an alkyl group having 1 to 6 carbon atoms
- R 4 represents a hydrogen group or a methyl group
- R 5 represents a divalent hydrocarbon group having 1 to 10 carbon atoms
- R 6 and R 7 Represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms.
- Q is an integer from 0 to 3
- p is an integer from 0 to 4.
- q is an integer of 2 or more, two or more R 3 s may be the same or different.
- aminosilane (b) examples include N- ( ⁇ -aminoethyl) - ⁇ -aminopropyltrimethoxysilane, N- ( ⁇ -aminoethyl) - ⁇ -aminopropyltriethoxysilane, N- ( ⁇ -amino Ethyl) - ⁇ -aminopropyltriisopropoxysilane, N- ( ⁇ -aminoethyl) - ⁇ -aminopropylmethyldimethoxysilane, N- ( ⁇ -aminoethyl) - ⁇ -aminopropylmethyldiethoxysilane, N- ( ⁇ -aminoethyl) - ⁇ -aminopropylmethyldiisopropoxysilane, ⁇ -aminopropyltrimethoxysilane, ⁇ -aminopropyltriisopropoxysilane, ⁇ -aminopropyldimethoxysilane,
- Crosslinking composition (C1) As the crosslinking agent, one of the above-mentioned (a) alkanolamine and (b) aminosilane can be used alone, or two or more can be used in combination. You can also
- the carboxylic acid that is the component (C2) constituting the crosslinked composition is represented by the following formula (3).
- X represents one or more groups selected from a chlorine group, a fluorine group, a bromine group and a hydroxyl group
- R 8 represents a hydrocarbon group
- z is an integer of 1 or more
- m is an integer of 1 or more.
- the carboxylic acid as the component (C2) is obtained by mono- and polycarboxyl substitution on the R 8 portion which is a hydrocarbon group, but has an X substituent having more than two single carbon atoms. There is nothing.
- m and z independently have a value of 1, 2, 3 or 4.
- R 8 is a saturated or unsaturated hydrocarbon group having 1 to 20 carbon atoms, and includes a linear or branched aliphatic hydrocarbon group, an alicyclic hydrocarbon group, or an aromatic hydrocarbon group. That is, it can be a linear or branched alkylene group having 1 to 20 carbon atoms, a cyclic alkylene group having 4 to 10 carbon atoms, an arylene group having 6 to 20 carbon atoms, an alkali-ylene group, or an aralkylene group. An alkylene group having 2 to 10 carbon atoms and an arylene group having 6 carbon atoms are most preferable.
- R 8 More specific examples of R 8 include methylene group, ethylene group, 1,1-propylene group, 1,3-propylene group, 1,2-propylene group, 1,4-butylene group, 1,1-amylene group. 1,1-decylene group, 2-ethyl-1,1-pentylene group, 2-ethylhexylene group, o-, m-, p-phenylene group, ethyl-p-phenylene group, 2,5-naphthylene group P, p′-biphenylene group, cyclopentylene group, cycloheptylene group, xylene group, 1,4-dimethylenephenylene group and the like.
- hydrocarbon groups have at least two available substitution points, one for the carboxyl group and one for the hydroxyl group (hydroxyl group) or halogen group, but the addition on the hydrocarbon group It is possible to further replace typical hydrogens with halogens and / or hydroxyl groups and / or carboxyl groups.
- carboxylic acid component (C2) examples include salicylic acid, benzylic acid, hydroxybenzoic acid, dihydroxybenzoic acid, trihydroxybenzoic acid, gluconic acid, citric acid, glycolic acid, dimethylolpropionic acid, malic acid, lactic acid , Tartaric acid, 2-hydroxymethylpropionic acid, hydroxybutyric acid, chloropropionic acid, bromopropionic acid, dichloropropionic acid, dibromopropionic acid, chloroacetic acid, dichloroacetic acid, bromoacetic acid, dibromoacetic acid, bromobutyric acid, bromoisobutyric acid, dichlorophenylacetic acid, Bromomalonic acid, dibromosuccinic acid, 3-chloro-2-hydroxypropionic acid, dichlorophthalic acid, chloromaleic acid, fluorobenzoic acid, chlorobenzoic acid, bromobenzoic acid, difluorobenzoic acid, dichlor
- the (C) crosslinking agent composition further comprises 2-methyl-1,3-propanediol and / or polyoxyethylene glyceryl ether together with the (C2) carboxylic acid and the (C1) crosslinking agent.
- the blending ratio of the (C) crosslinking agent composition is 0.005 to 20 parts by mass with respect to 100 parts by mass of the active hydrogen-containing compound as the component (B).
- (C) When the mixture ratio of a crosslinking agent composition is less than 0.005 mass part, the effect of improving the hardness of a foam (foam) and suppressing the viscosity rise of a composition cannot fully be raised. Moreover, since a fall of another physical property will arise when a mixture ratio exceeds 20 mass parts, it is unpreferable.
- the content ratio of the (C1) crosslinking agent in the (C) crosslinking agent composition is 5 to 90% by mass.
- the content (number of moles) of (C1) cross-linking agent is greater than the content (number of moles) of (C2) carboxylic acid. That is, it is preferable that the block ratio of the amino group (the amino group possessed by the (C1) crosslinking agent) due to the carboxyl group of (C2) carboxylic acid is not 100% but 5 to 80%.
- a catalyst and a foam stabilizer can be blended in addition to the components (A) to (C), and further, a filler, a stabilizer, and a colorant as necessary. Additives such as flame retardants can be blended.
- the catalyst promotes the reaction between an isocyanate group in (A) polyisocyanate and an active hydrogen-containing group in (B) an active hydrogen-containing compound.
- a foam stabilizer is a surfactant blended to form good bubbles. Any foam stabilizer can be used as long as it is a known foam stabilizer in the polyurethane industry. For example, there are a silicone-based foam stabilizer and a fluorine-containing compound-based foam stabilizer.
- a flexible polyurethane foam can be produced by a one-shot foaming method.
- the “one-shot foaming method” is a method for producing a polyurethane foam in one step. In this method, all of the ingredients necessary to produce a polyurethane foam, including polyisocyanate, polyol, water, crosslinker, catalyst, foam stabilizer, optional blowing agent, etc., are simply blended together. Cast on a moving conveyor or in a suitably shaped mold and cure.
- the production efficiency is greatly improved by using a specific crosslinking agent composition.
- a polyurethane foam with good physical properties can be obtained.
- Examples 1-8, Comparative Examples 1-6 (A) Dialkanolamine and N-hexyldiethanolamine as alkanolamine, (b) ⁇ -aminopropyltriethoxysilane as aminosilane, various carboxylic acids (C2) shown in Table 1, 2-methyl-1,3-propanediol And Unix G-450 (polyoxyethylene glycol (8) glyceryl ether; manufactured by NOF Corporation) were blended in the compositions shown in Table 1, respectively, to prepare crosslinking agent compositions (crosslinking agent-1 to crosslinking agent-12). did.
- C2 carboxylic acids
- components other than the carboxylic acid (C2) were manually stirred and mixed for 3 minutes at room temperature, and then the carboxylic acid (C2) was gradually added and mixed over 1 minute. Only diisopropanolamine (melting point: 44 ° C.) was heated to 60 ° C. to be completely liquid and mixed at room temperature.
- “part” means “part by mass”.
- crosslinking agent-1 to crosslinking agent-12 (A) polyisocyanate, (B1) polyol, (B2) water, catalyst and foam stabilizer were blended in the compositions shown in Tables 2 and 3, respectively. And mixed with a high speed mixer.
- the obtained composition was immediately poured into an aluminum mold (inner dimensions 300 ⁇ 300 ⁇ 100 mm) whose temperature was adjusted to 60 ⁇ 2 ° C., the lid was closed, and the mixture was held as it was for 5 minutes for foam molding.
- (A) Polyisocyanate is Coronate 1021 (Blend isocyanate consisting of 80% by weight TDI-80 and 20% by weight Crude MDI, index 95; manufactured by Nippon Polyurethane Industry Co., Ltd.), and (B1) polyol is Sunnix FA-703 (glycerin-propylene oxide / ethylene oxide adduct, hydroxyl value 34 mgKOH / g; manufactured by Sanyo Chemical Industries) and SANNICS FA-728R (polymer polyol, hydroxyl value 34 mgKOH / g; manufactured by Sanyo Chemical Industries) As catalysts, NIAX CATALYST A-33 and NIAX CATALYST A-1 (both manufactured by Momentive Performance Materials Japan GK) and UAX-6675 (silicone-based foam stabilizer) as foam stabilizers. Momentive Performance Materials Japan made a joint company) was used, respectively.
- discharge time As the discharge time, the time (seconds) from the addition of (A) polyisocyanate to the reaction mixture to the first appearance after the foam was extruded from the four vent holes at the top of the mold was measured.
- FTC Force-to-crush
- Crosslinking Agent-1 to Crosslinking Agent-2, Crosslinking Agent-4 to Crosslinking Agent-6, Crosslinking Agent-8, Crosslinking Agent-10 and Crosslinking Agent-12 were used.
- the polyurethane foams of Examples 1 to 8 obtained as above were the polyurethane foams of Comparative Examples 1 and 4 obtained without blending the crosslinking agent, and the crosslinking agent-3, crosslinking agent-7, and crosslinking agent-9.
- the hardness (hardness) is improved and the discharge time is longer. And FTC is also reduced.
- the polyurethane foams of Examples 1 to 8 have good values of compression residual strain CS (%) and wet heat aging test Wet set (%), which are about the same as those of Comparative Examples 1 to 6. Furthermore, it can be seen that the polyurethane foams obtained in Examples 1 to 5 have good mechanical properties (breaking elongation Eb, rebound elastic force BR, and tear strength Ts) comparable to those of Comparative Examples 1 to 3.
Abstract
Description
(A)成分であるポリイソシアネートとしては、2個以上のイソシアネート基を有する公知の脂肪族、脂環族および芳香族の有機イソシアネート化合物を使用することができる。例えば、ヘキサメチレンジイソシアネート、イソホロンジイソシアネート、4,4-ジシクロヘキシルメタンジイソシアネート、2,4-あるいは2,6-トリレンジイソシアネート(トルエンジイソシアネートあるいはトルイジンジイソシアネート:TDI)、2,2’-または2,4-あるいは4,4’-ジフェニルメタンジイソシアネート(MDI)のようなアルキレンジイソシアネートあるいはアリーレンイソシアネート、ならびに公知のトリイソシアネートおよびポリメリックMDI(粗製ジフェニルメタンジイソシアネート;クルードMDIと呼称されている)などが挙げられる。
(B)成分である活性水素含有化合物は、(B1)ポリオールと(B2)水をそれぞれ含有する。
1)ポリヒドロキシアルカンのアルキレンオキサイド付加物
2)非還元糖および糖誘導体のアルキレンオキサイド付加物
3)リン酸およびポリリン酸のアルキレンオキサイド付加物
4)ポリフェノール類のアルキレンオキサイド付加物
5)一級および二級アミンのアルキレンオキサイド付加物である。
(C)架橋剤組成物は、(a)アルカノールアミンと(b)アミノシランから選ばれる少なくとも1種の架橋剤(C1)と、少なくとも1種のカルボン酸(C2)をそれぞれ含有する。
HxR1 yN((R2O)nH)3-x-y………(1)
(R3O)qR4 3-qSi-R5-(NHCH2CH2)pNR6R7………(2)
Xz-R8(COOH)m………(3)
(a)アルカノールアミンとして、ジイソプロパノールアミンおよびN-ヘキシルジエタノールアミン、(b)アミノシランとしてγ-アミノプロピルトリエトキシシラン、表1に示す各種カルボン酸(C2)、2-メチル-1,3-プロパンジオールおよびユニックスG-450(ポリオキシエチレングリコール(8)グリセリルエーテル;日本油脂社製)を、それぞれ表1に示す組成で配合し、架橋剤組成物(架橋剤-1~架橋剤-12)を調製した。架橋剤組成物の調製においては、室温でカルボン酸(C2)以外の成分を3分間手動で撹拌・混合した後、1分間かけて徐々にカルボン酸(C2)を加えて混合した。なお、ジイソプロパノールアミン(融点44℃)のみは、60℃に加熱して完全に液状にしたものを室温で混合した。表1において部は質量部を示す。
吐出時間としては、反応混合物への(A)ポリイソシアネートの添加から、金型上部の4箇所のガス抜き孔から発泡体が押出されて最初に出現するまでの時間(秒)を測定した。
FTCは、型から出して1分後から測定し、発泡体(フォームパッド)を最初の厚さから50%まで圧縮するのに必要なピーク力である。硬さ測定に使用されるものと同じ設定の荷重試験器を用いて測定した。FTC値は発泡の連通性を評価する良好な尺度であり、FTC値が低いほど発泡の連通性が高い。
JIS K6401の硬さ測定に準じ、型から出して室温にて1日静置後に、FTC測定について使用したものと同じパッドを測定した。
Claims (9)
- (A)ポリイソシアネートと、
(B)(B1)ポリオールと(B2)水をそれぞれ含む活性水素含有化合物、および
(C)架橋剤組成物を前記(B)成分である活性水素含有化合物100質量部に対して0.1~20質量部
を含有するポリウレタン発泡組成物であり、
前記(C)架橋剤組成物は、
式(1):
HxR1 yN((R2O)nH)3-x-y………(1)
(式中、R1は、炭素数1~12のアルキル基またはアリール基もしくはアラルキル基から選ばれる炭化水素基、R2は炭素数2~4のアルキル基をそれぞれ示す。xは0~2の整数、yは0~2の整数、x+yは0~2の整数、nは1~10の整数である。)
で表わされるアルカノールアミン(a)と、
式(2):
(R3O)qR4 3-qSi-R5-(NHCH2CH2)pNR6R7………(2)
(式中、R3は炭素数1~6のアルキル基、R4は水素基またはメチル基、R5は炭素数1~10の2価の炭化水素基、R6およびR7は水素原子または炭素数1~20の1価の炭化水素基をそれぞれ示す。qは0~3の整数、pは0~4の整数である。)
で表わされるアミノシラン(b)から選ばれる少なくとも1種の架橋剤(C1)と、
式(3):
Xz-R8(COOH)m………(3)
(式中、R8は炭化水素基、Xは塩素基、フッ素基、臭素基、および水酸基から選ばれる基をそれぞれ示す。zは1以上の整数、mは1以上の整数である。)
で表わされる少なくとも1種のカルボン酸(C2)をそれぞれ含有し、
前記(C)架橋剤組成物中の前記(C1)架橋剤の含有量(モル数)が、前記(C2)カルボン酸の含有量(モル数)より大きいことを特徴とするポリウレタン発泡組成物。 - 前記(C)架橋剤組成物全体に対する前記(C1)架橋剤の含有割合が、5~90質量%であることを特徴とする請求項1記載のポリウレタン発泡組成物。
- 前記(a)アルカノールアミンが、2個のアルカノール基を有する2級アミンであることを特徴とする請求項1または2記載のポリウレタン発泡組成物。
- 前記(a)アルカノールアミンが、ジイソプロパノールアミンおよび/またはN-ヘキシルジエタノールアミンであることを特徴とする請求項3記載のポリウレタン発泡組成物。
- 前記(b)アミノシランが、γ-アミノプロピル基またはN-(β-アミノエチル)-γ-アミノプロピル基を有するシランであることを特徴とする請求項1ないし4のいずれか1項記載のポリウレタン発泡組成物。
- 前記(C2)カルボン酸の分子量が300以下であることを特徴とする請求項1ないし5のいずれか1項記載のポリウレタン発泡組成物。
- 前記(C2)カルボン酸が、サリチル酸、乳酸、グルコン酸、2-クロロプロパン酸から選ばれる少なくとも1種であることを特徴とする請求項6記載のポリウレタン発泡組成物。
- 前記(C)架橋剤組成物は、2-メチル-1,3-プロパンジオールおよび/またはポリオキシエチレングリコールグリセリルエーテルをさらに含有することを特徴とする請求項1ないし7のいずれか1項記載のポリウレタン発泡組成物。
- 請求項1ないし8のいずれか1項記載のポリウレタン発泡組成物を用いることを特徴とするポリウレタンフォームの製造方法。
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP10783144.8A EP2439221B1 (en) | 2009-06-02 | 2010-06-02 | Expandable polyurethane composition and process for production of polyurethane foam |
US13/131,479 US9266994B2 (en) | 2009-06-02 | 2010-06-02 | Expandable polyurethane composition and manufacturing method of polyurethane foam |
KR1020117012098A KR101718171B1 (ko) | 2009-06-02 | 2010-06-02 | 폴리우레탄 발포 조성물과 폴리우레탄 폼의 제조 방법 |
CN201080003508.7A CN102395613B (zh) | 2009-06-02 | 2010-06-02 | 聚氨酯发泡组合物以及聚氨酯泡沫的制造方法 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2009-132793 | 2009-06-02 | ||
JP2009132793A JP4691683B2 (ja) | 2009-06-02 | 2009-06-02 | ポリウレタン発泡組成物およびポリウレタンフォームの製造方法 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2010140356A1 true WO2010140356A1 (ja) | 2010-12-09 |
Family
ID=43297499
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2010/003677 WO2010140356A1 (ja) | 2009-06-02 | 2010-06-02 | ポリウレタン発泡組成物およびポリウレタンフォームの製造方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US9266994B2 (ja) |
EP (1) | EP2439221B1 (ja) |
JP (1) | JP4691683B2 (ja) |
KR (1) | KR101718171B1 (ja) |
CN (1) | CN102395613B (ja) |
WO (1) | WO2010140356A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20220072083A (ko) | 2020-11-24 | 2022-06-02 | 임창오 | 폴리우레탄 발포 복합체의 제조 방법 |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4897082B2 (ja) * | 2008-04-25 | 2012-03-14 | トーヨーポリマー株式会社 | ポリウレタン発泡体及び研磨パッド |
EP2643378B1 (de) * | 2010-11-22 | 2014-10-08 | Bayer Intellectual Property GmbH | Verfahren zur herstellung von polyurethanweichschaumstoffen |
JP5513684B2 (ja) | 2012-04-26 | 2014-06-04 | モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 | ポリウレタン発泡組成物および軟質ポリウレタンフォームの製造方法 |
CN104245768A (zh) | 2012-04-26 | 2014-12-24 | 迈图高新材料日本合同公司 | 聚氨酯发泡组合物和软质聚氨酯泡沫的制备方法 |
CN112898523B (zh) * | 2021-01-25 | 2022-05-31 | 惠彩材料科技(苏州)有限公司 | 一种聚氨酯泡棉及其制备方法和应用 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH072968A (ja) * | 1993-06-15 | 1995-01-06 | Sanyo Chem Ind Ltd | 熱成形性軟質ポリウレタンフォームの製法、熱成形材及び熱成形方法 |
JPH07157528A (ja) * | 1993-12-03 | 1995-06-20 | Nisshinbo Ind Inc | 変性ポリイソシアヌレート発泡体の製造法 |
US5977198A (en) | 1997-06-13 | 1999-11-02 | Bayer Aktiengesellschaft | Process for the production of resilient, flexible polyurethane foams |
JP2001048947A (ja) * | 1999-08-09 | 2001-02-20 | Kao Corp | ポリウレタンフォーム断熱材の製造法 |
JP2007535606A (ja) * | 2004-04-30 | 2007-12-06 | ダウ グローバル テクノロジーズ インコーポレイティド | 改善されたエージング特性を有する低密度ポリウレタンフォームのための自触媒性ポリオールの共触媒作用 |
US20070287761A1 (en) | 2006-06-12 | 2007-12-13 | Jared Denis Bender | Catalyst compositions for improving polyurethane foam performance |
JP2008239725A (ja) * | 2007-03-27 | 2008-10-09 | Nippon Polyurethane Ind Co Ltd | 硬質ポリウレタンフォーム用ポリイソシアネート組成物、及び硬質ポリウレタンフォームの製造方法 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
LU74540A1 (ja) * | 1976-03-12 | 1977-09-27 | ||
US4282330A (en) | 1979-08-03 | 1981-08-04 | Texaco Inc. | Energy management polyether polyurethane foam |
US5162382A (en) * | 1989-08-25 | 1992-11-10 | The Dow Chemical Company | Polyurethanes containing multipurpose additives |
DE3934955A1 (de) * | 1989-10-20 | 1991-04-25 | Bayer Ag | Verfahren zur herstellung von formkoerpern aus polyurethanschaumstoffen und die nach diesem verfahren erhaltenen formkoerper |
DE4121161A1 (de) * | 1991-06-27 | 1993-01-07 | Basf Ag | Verfahren zur herstellung von urethan- oder urethan- und isocyanuratgruppen enthaltenden hartschaumstoffen und treibmittel enthaltende emulsionen hierfuer |
US5489618A (en) * | 1993-11-29 | 1996-02-06 | Osi Specialties, Inc. | Process for preparing polyurethane foam |
US6395796B1 (en) * | 1999-01-05 | 2002-05-28 | Crompton Corporation | Process for preparing polyurethane foam |
US6660781B1 (en) * | 1999-01-05 | 2003-12-09 | Witco Corporation | Process for preparing polyurethane foam |
DE10063497A1 (de) * | 2000-12-20 | 2002-07-04 | Bayer Ag | Polyurethanelastomere mit verbesserter Hydrolysestabilität |
JP5547365B2 (ja) | 2007-03-27 | 2014-07-09 | 関西ペイント株式会社 | 表面処理剤及び該処理剤を塗布してなる表面処理方法 |
-
2009
- 2009-06-02 JP JP2009132793A patent/JP4691683B2/ja active Active
-
2010
- 2010-06-02 US US13/131,479 patent/US9266994B2/en active Active
- 2010-06-02 CN CN201080003508.7A patent/CN102395613B/zh active Active
- 2010-06-02 KR KR1020117012098A patent/KR101718171B1/ko active IP Right Grant
- 2010-06-02 WO PCT/JP2010/003677 patent/WO2010140356A1/ja active Application Filing
- 2010-06-02 EP EP10783144.8A patent/EP2439221B1/en active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH072968A (ja) * | 1993-06-15 | 1995-01-06 | Sanyo Chem Ind Ltd | 熱成形性軟質ポリウレタンフォームの製法、熱成形材及び熱成形方法 |
JPH07157528A (ja) * | 1993-12-03 | 1995-06-20 | Nisshinbo Ind Inc | 変性ポリイソシアヌレート発泡体の製造法 |
US5977198A (en) | 1997-06-13 | 1999-11-02 | Bayer Aktiengesellschaft | Process for the production of resilient, flexible polyurethane foams |
JP2001048947A (ja) * | 1999-08-09 | 2001-02-20 | Kao Corp | ポリウレタンフォーム断熱材の製造法 |
JP2007535606A (ja) * | 2004-04-30 | 2007-12-06 | ダウ グローバル テクノロジーズ インコーポレイティド | 改善されたエージング特性を有する低密度ポリウレタンフォームのための自触媒性ポリオールの共触媒作用 |
US20070287761A1 (en) | 2006-06-12 | 2007-12-13 | Jared Denis Bender | Catalyst compositions for improving polyurethane foam performance |
JP2008239725A (ja) * | 2007-03-27 | 2008-10-09 | Nippon Polyurethane Ind Co Ltd | 硬質ポリウレタンフォーム用ポリイソシアネート組成物、及び硬質ポリウレタンフォームの製造方法 |
Non-Patent Citations (1)
Title |
---|
See also references of EP2439221A4 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20220072083A (ko) | 2020-11-24 | 2022-06-02 | 임창오 | 폴리우레탄 발포 복합체의 제조 방법 |
Also Published As
Publication number | Publication date |
---|---|
JP4691683B2 (ja) | 2011-06-01 |
CN102395613A (zh) | 2012-03-28 |
KR101718171B1 (ko) | 2017-03-20 |
US20110263740A1 (en) | 2011-10-27 |
EP2439221A1 (en) | 2012-04-11 |
EP2439221B1 (en) | 2016-08-03 |
KR20120027104A (ko) | 2012-03-21 |
US9266994B2 (en) | 2016-02-23 |
EP2439221A4 (en) | 2013-02-27 |
CN102395613B (zh) | 2014-06-25 |
JP2010280743A (ja) | 2010-12-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA2337913C (en) | Process for preparing a flexible polyurethane foam | |
JP4066069B2 (ja) | ポリウレタン発泡体の性能を高める方法 | |
EP1018525B1 (en) | Process for preparing polyurethane foam | |
EP1249461B1 (en) | Acid-blocked amine catalysts for the production of polyurethanes | |
JP4691683B2 (ja) | ポリウレタン発泡組成物およびポリウレタンフォームの製造方法 | |
JP6703945B2 (ja) | Pipaポリオール系の従来の軟質発泡体 | |
AU775998B2 (en) | Polyisocyanate compositions and a process for the production of low-density flexible foams with low humid aged compression sets from these polyisocyanate compositions | |
US20030087978A1 (en) | Process for preparing a free rise or slabstock flexible polyurethane foam | |
US20100099785A1 (en) | Tertiary amines blocked with polymer acids | |
KR20130041197A (ko) | 폴리우레탄 포움 성능을 개선시키기 위한 첨가제 | |
JP4603003B2 (ja) | ポリウレタン発泡体の劣化を最小化するための、芳香族二酸エステルジオールおよびそれらの置換カルバメート | |
JPH11228663A (ja) | 液体イソシアネート末端のアロファネート改変mdiプレポリマー配合物に基づく軟質フォームおよび軟質成形フォーム、並びにこれらフォームの製造方法 | |
KR102092424B1 (ko) | 폴리우레탄 발포조성물 및 연질 폴리우레탄 폼의 제조방법 | |
JP2010530469A (ja) | ポリウレタン用の反応性アミン触媒 | |
JPH0812737A (ja) | 軟質ポリウレタン発泡体の製造方法 | |
JPH01215817A (ja) | ポリウレタンフォームの製法 | |
JPH08157554A (ja) | 高弾性軟質ポリウレタン発泡体およびその製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 201080003508.7 Country of ref document: CN |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 10783144 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 13131479 Country of ref document: US |
|
ENP | Entry into the national phase |
Ref document number: 20117012098 Country of ref document: KR Kind code of ref document: A |
|
REEP | Request for entry into the european phase |
Ref document number: 2010783144 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2010783144 Country of ref document: EP |
|
NENP | Non-entry into the national phase |
Ref country code: DE |