WO2006108833A1 - Verfahren zur herstellung von polyurethan- und polyisocyanurat-hartschaumstoffen - Google Patents
Verfahren zur herstellung von polyurethan- und polyisocyanurat-hartschaumstoffen Download PDFInfo
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- WO2006108833A1 WO2006108833A1 PCT/EP2006/061506 EP2006061506W WO2006108833A1 WO 2006108833 A1 WO2006108833 A1 WO 2006108833A1 EP 2006061506 W EP2006061506 W EP 2006061506W WO 2006108833 A1 WO2006108833 A1 WO 2006108833A1
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- isocyanate
- aii
- polyester
- alcohols
- prepolymers
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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
- C08G18/28—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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4288—Polycondensates having carboxylic or carbonic ester groups in the main chain modified by higher fatty oils or their acids or by resin acids
-
- 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
- C08J9/22—After-treatment of expandable particles; Forming foamed 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
-
- 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
- C08J9/06—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 chemical blowing agent
-
- 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 invention relates to a process for the preparation of rigid polyurethane and polyisocyanurate foams by reacting polyisocyanates with compounds having at least two isocyanate-reactive hydrogen atoms.
- Polyurethane and polyisocyanurate rigid foams have long been known and are widely used in the art.
- An essential field of application of the rigid polyurethane and polyisocyanurate foams are composite elements.
- the object of the present invention was therefore to provide a polyurethane or polyisocyanate system which ensures a consistently high quality of the sandwich elements produced, even under fluctuating external influences and production conditions.
- good adhesion of the foam to the outer layers, even over a long period of time, should be ensured, soil disturbances minimized and the highest possible conversion of the isocyanate groups should be achieved.
- the object could be surprisingly achieved by using prepolymers containing isocyanate groups as polyisocyanates and the compounds having two isocyanate-reactive hydrogens containing at least one polyester alcohol which was prepared with the concomitant use of at least one hydrophobic insert component.
- the invention accordingly provides a process for the production of rigid polyurethane and polyisocyanurate foams by reacting polyisocyanates a) with compounds having at least two isocyanate-reactive hydrogen atoms b) in the presence of blowing agents c), characterized in that the polyisocyanates a) isocyanate group-containing prepolymers based on monomeric (MMDI) and polymeric diphenylmethane diisocyanate (PMDI) having an NCO content in the range of 25 to 31 wt .-%, preferably 26 to 30 wt .-%, particularly preferably 28-29 wt.
- MMDI monomeric
- PMDI polymeric diphenylmethane diisocyanate
- NCO content according to the invention for example reduced soil susceptibility and improved adhesion, and in the case of the production of polyisocyanurate foams, sufficient PIR structures are also formed in order to achieve excellent flame retardancy. If the NCO content of the prepolymers is lowered below the stated range, there are no longer sufficient isocyanate groups available for the PIR reaction, and the flame retardant properties of the foam deteriorate. Furthermore, at NCO contents of less than 26 wt .-%, the viscosity of the prepolymer increases sharply, so that the processability of the system is impaired.
- the preparation of the prepolymers used as polyisocyanates a) is carried out by customary process by reacting an excess of an isocyanate component ai) with a polyol component aii), wherein the NCO value of the prepolymers 25-31 wt .-%, preferably 26-30 wt .-% , particularly preferably 28-29 wt .-% is.
- isocyanate component ai) for the preparation of the prepolymers monomeric MDI or mixtures of monomeric and polymeric MDI are used. Such mixtures are also referred to as crude MDI. Preferably, these mixtures have an NCO content of 29-33 wt .-%, and a content of 2-core MDI of 41 + 5 wt .-%, based on the weight of the PMDI.
- monomeric MDI 4'-MDI, 2,4'-MDI and 2,2'-MDI and any mixtures of said isomers can be used. It is also possible to modify the monomeric MDI by incorporation of functional groups. This can serve to liquefy the monomeric MDI, but it can also be targeted to change the properties of the MDI. For example, allophanate, uretdione or isocyanurate groups can be incorporated into the MDI as functional groups. Furthermore, TDI, HDI, NDI and IPDI can be used as isocyanates.
- the viscosity of the prepolymer at 25 ° C. should be in the range between 100-3000 mPas, preferably 200-1500 mPas, particularly preferably 300-1200 mPas.
- the prepolymer should furthermore have a content of monomeric MDI of 28 to 38% by weight, preferably 28 to 29% by weight, based on the weight of the prepolymer.
- compounds having at least two isocyanate-reactive hydrogen atoms aii) for the preparation of the prepolymers a) containing isocyanate groups in particular Herfunktione.lle alcohols are used.
- polyether alcohols and / or polyester alcohols are used.
- 1, 5 to 3-functional, particularly preferably 1, 5 to 2.5-functional polyether and / or polyester alcohols are used.
- the viscosity of the prepolymers would increase too much.
- the polyester alcohols used as component aii) preferably have a hydroxyl number in the range between 50 and 400 mg KOH / g, particularly preferably 100 and 300 mg KOH / g, and in particular 150 and 250 mg KOH / g.
- the polyester alcohols aii) are usually prepared in the usual way by reacting polyfunctional alcohols with polyfunctional carboxylic acids or carboxylic acid derivatives, in particular anhydrides.
- Alcohols are usually 2- or 3-functional alcohols, for example ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, glycerol, trimethylolpropane and / or butanediol.
- the carboxylic acids used are preferably adipic acid, phthalic acid and / or phthalic anhydride.
- the polyether alcohols used as component aii) preferably have a hydroxyl number in the range between 50 and 300 mgKOH / g, in particular 80 and 250 mg KOH / g.
- the polyether alcohols aii) are preferably prepared by addition of alkylene oxides to 2- and / or 3-functional alcohols having a molecular weight of 62 to 400.
- the alkylene oxides used are usually ethylene oxide and / or propylene oxide.
- alcohols for example, ethylene glycol, diethylene glycol, propylene glycol, glycerol or any desired mixtures of these alcohols can be used.
- the addition of the alkylene oxides to the starting substances is carried out in the usual way, usually using basic catalysts.
- hydrophobic starting materials are also used in the preparation of the polyester alcohols aii).
- the hydrophobic substances are water-insoluble substances which contain a nonpolar organic radical and have at least one reactive group from the series hydroxyl, carboxylic acid, carboxylic acid ester or mixtures thereof.
- the equivalent weight of the hydrophobic materials is between 130 and 1000.
- fatty acids such as stearic acid, oleic acid, palmitic acid, lauric acid or linoleic acid and fats and oils such as castor oil, corn oil, sunflower oil, soybean oil, coconut oil, olive oil or tall oil can be used.
- Rophobe feeds are used, they are used in an amount of 1-20 mol%, preferably 4-15 mol%, based on the polyester alcohol.
- Suitable compounds having at least two isocyanate-reactive hydrogen atoms b) for the preparation of the polyurethanes and / or polyisocyanurates are preferably alcohols, in particular polyether alcohols and / or polyester alcohols.
- the compounds having at least two isocyanate-reactive hydrogen atoms b) contain at least one polyester alcohol bi) which has been prepared using hydrophobic feedstocks. These polyester alcohols correspond in their structure to those for the preparation of the isocyanate groups
- polyester alcohols aii) and bi) may be different or identical. In a preferred embodiment, the polyester alcohols aii) and bi) are identical.
- the polyester alcohol bi can be used as the sole compound having at least two isocyanate-reactive hydrogen atoms.
- further compounds having at least two hydrogen atoms reactive with isocyanate groups are used.
- the polyols used in combination with the polyester alcohols bi) may be polyether alcohols bii) and / or polyester alcohols biii).
- the polyether alcohols bii) are preferably those having a functionality of from 2 to 3 and a hydroxyl number in the range from 50 to 300 mg KOH / g, as used for preparing the prepolymers and described above.
- the polyester alcohols biii) are preferably from 1.5 to 3, more preferably from 1 to 5, to 2.5-functional having a hydroxyl number in the range from 50 to 400 mg KOH / g, as used in the preparation the prepolymers can be used and are described above.
- the polyester alcohols Biii) are prepared without the use of a hydrophobic insert component.
- both the polyester alcohols used for producing the prepolymers aii) and the polyester alcohols bi) used in component b) are free from terephthalic acid.
- the proportions of polyols bi), bii) and biii) are preferably bi) 20-90 wt .-%, bii) 5-30 wt .-%, biii) 0-90 wt .-% and particularly preferably bi) 20- 90% by weight, bii) 5-30% by weight and biii) 5-90% by weight, the sum of bi), bii) and biii) being 100.
- polyether alcohols bii) polyether alcohols can be used in addition to the above-described polyether alcohols or instead of the polyether alcohols described above, such as are commonly used for the production of rigid polyurethane foams application.
- polyether alcohols which have a functionality of at least 2 to 6 and a hydroxyl number greater than 250 mg KOH / g and, as well as the polyether used in component aii), by known methods, for example by anionic addition of alkylene oxides to H functional starter substances in the presence of basic catalysts, in particular alkali metal hydroxides.
- the alkylene oxides used are preferably ethylene oxide and propylene oxide.
- the alkylene oxides can be used individually, alternately in succession or as mixtures.
- Suitable starter molecules are: water, alkanolamines, e.g. Ethanolamine, N-methyl and N-ethylethanolamine, dialkanolamines such as diethanolamine, N-methyl and N-ethyldiethanolamine and trialkanolamines such as e.g. Triethanolamine and ammonia, and tolylenediamine and diaminodiphenylmethane.
- alkanolamines e.g. Ethanolamine, N-methyl and N-ethylethanolamine
- dialkanolamines such as diethanolamine
- N-methyl and N-ethyldiethanolamine and trialkanolamines
- Triethanolamine and ammonia e.g. Triethanolamine and ammonia
- tolylenediamine and diaminodiphenylmethane e.g. Triethanolamine and ammonia
- polyhydric especially dihydric to octahydric alcohols, such as ethanediol, propanediol-1, 2 and -1, 3, diethylene glycol, dipropylene glycol, butanediol-1, 4, hexanediol-1, 6, glycerol, pentaerythritol, sorbitol and sucrose, polyvalent Phenols, such as 4,4'-dihydroxydiphenylmethane and 4,4'-dihydroxy-diphenylpropane-2,2, resoles, e.g. oligomeric condensation products of phenol and formaldehyde and Mannich condensates of phenols, formaldehyde and dialkanolamines and melamine are used.
- dihydric to octahydric alcohols such as ethanediol, propanediol-1, 2 and -1, 3, diethylene glycol, dipropylene glycol, butane
- polyester alcohols biii) can, as in the treatment of component ai) carried out, be prepared by reacting polyfunctional carboxylic acids with polyfunctional alcohols.
- blowing agents c) and catalysts, flame retardants and customary auxiliaries and / or additives are usually carried out in the presence of blowing agents c) and catalysts, flame retardants and customary auxiliaries and / or additives.
- blowing agents c) and catalysts, flame retardants and customary auxiliaries and / or additives are usually carried out in the presence of blowing agents c) and catalysts, flame retardants and customary auxiliaries and / or additives.
- water which reacts with isocyanate groups with elimination of carbon dioxide.
- carboxylic acids preferably formic acid and / or acetic acid can be used as a chemical blowing agent.
- so-called physical blowing agents can also be used. These are compounds which are inert to the starting components and which are usually liquid at room temperature and evaporate under the conditions of the urethane reaction. The boiling point of these compounds is preferably below 50 ° C.
- the physical blowing agents also include compounds which are gaseous at room temperature and under pressure in the feed components are incorporated or dissolved in them, for example carbon dioxide, low-boiling alkanes and fluoroalkanes.
- the physical blowing agents are usually selected from the group comprising alkanes and / or cycloalkanes having at least 4 carbon atoms, dialkyl ethers, esters, ketones, acetals, fluoroalkanes having 1 to 8 carbon atoms, and tetraalkylsilanes having 1 to 3 carbon atoms in the alkyl chain, in particular tetramethylsilane.
- Examples include propane, n-butane, iso- and cyclobutane, n-, iso- and cyclopentane, cyclohexane, dimethyl ether, methyl ethyl ether, methyl butyl ether, methyl formate, acetone, and fluoroalkanes, such as trichlorofluoromethane (R11), dichlorofluoro methane (141b ), 1,1,3,3-pentafluorobutane (365 mfc), 1,1,1,3,3-pentafluoropropane (245fa) and 1,1,1,2-tetrafluoroethane (134a).
- the said physical blowing agents can be used alone or in any combination with each other. Preference is given to using isomers of pentane, in particular cyclopentane and n-pentane, particularly preferably n-pentane.
- carboxylic acids preferably formic acid
- hydrogen fluorocarbons as the physical blowing agent
- water is used as the chemical blowing agent and hydrocarbons, preferably homologues of the pentane, more preferably n-pentane, are used as the physical blowing agent.
- carboxylic acids preferably formic acid
- hydrocarbons preferably homologs of the pentane, particularly preferably n-pentane, are used as the physical blowing agent.
- the blowing agents used are preferably free of fluorine-chlorine-hydrocarbons (CFCs), preferably free of CFCs and HFCs, particularly preferably free of CFCs, HFCs and HFCs.
- CFCs fluorine-chlorine-hydrocarbons
- the polyurethane or Polyisocyanuratschaumstoffe also contain flame retardants.
- bromine-free flame retardants are used.
- Flame retardants containing phosphorus atoms such as, for example, trischloroisopropyl phosphate, diethylethane phosphonate, triethyl phosphate, diphenyl cresyl phosphate and alkoxylated alkyl phosphonic acids, such as Exolit OP 560, are particularly preferred.
- exclusively halogen-free flame retardants are used.
- the catalysts used are in particular compounds which greatly accelerate the reaction of the isocyanate groups with the hydrogen atoms reactive with isocyanate groups. Such catalysts are usually strongly basic amines, such as tertiary aliphatic amines, imidazoles, amidines, and alkanolamines, and / or organometallic compounds, especially those based on tin.
- isocyanurate groups are to be incorporated into the rigid foam, special catalysts are required.
- the isocyanurate catalysts used are usually metal carboxylates, in particular potassium formate, potassium acetate and potassium octoate, the equivalent ammonium salts and their solutions.
- the catalysts can, depending on requirements, be used alone or in any mixtures with one another.
- auxiliaries and / or additives are the substances known per se for this purpose, for example surface-active substances, foam stabilizers, cell regulators, fillers, pigments, dyes, hydrolysis stabilizers, antistatic agents, fungistatic and bacteriostatic agents.
- the polyisocyanates a) and the compounds having at least two isocyanate-reactive hydrogen atoms b) are reacted in amounts such that the isocyanate index in the case of the polyurethane foams is in a range between 100 and 220, preferably between 105 and 180, lies.
- the index of> 180, preferably 200-500, preferably 225-400, particularly preferably 280-400 it is also possible to work with an index of> 180, preferably 200-500, preferably 225-400, particularly preferably 280-400.
- Polyurethane resp. Polyisocyanurate rigid foams can be prepared batchwise or continuously by means of known mixing devices. The mixing of the starting components can take place with the aid of known mixing devices.
- the rigid polyurethane foams according to the invention are usually prepared by the two-component process.
- the compounds having at least two isocyanate-reactive hydrogen atoms are mixed with the blowing agents, the catalysts and other auxiliaries and / or additives to form a so-called polyol component and these are mixed with the polyisocyanates or mixtures of the polyisocyanates and optionally blowing agents Implementation brought.
- the starting components are usually mixed at a temperature of 15 to 35 0 C, preferably from 20 to 30 0 C.
- the reaction mixture can be mixed with high or low pressure dosing.
- the rigid foams of the invention are preferably produced on continuously operating double-belt systems.
- the polyol and isocyanate component is metered and mixed in a mixing head.
- the polyol mixture can be previously metered with separate pumps catalysts and / or propellant.
- the reaction mixture is applied continuously to the lower cover layer.
- the lower cover layer with the reaction mixture and the upper cover layer enter the double belt.
- the reaction mixture foams and hardens.
- the endless strand is cut to the desired dimensions. In this way, sandwich elements with metallic cover layers or insulating elements with flexible cover layers can be produced
- the composite elements can also be produced discontinuously.
- the starting components are usually mixed at a temperature of 15 to 35 0 C, preferably from 20 to 30 0 C mixed.
- the reaction mixture can be poured into closed support tools with high or low pressure metering machines.
- the density of the rigid foams produced by the process according to the invention is 10 to 400 kg / m 3 , preferably 20-200, in particular 30 to 100 kg / m 3 .
- the thickness of the composite elements is usually 5 to 300 mm, preferably 5 to 250 mm.
- Polyesterol 1 prepared from phthalic anhydride and diethylene glycol, functionality 2, OHZ 250 mg KOH / g - polyesterol 2 prepared from phthalic anhydride, diethylene glycol, monoethylene glycol and oleic acid, functionality 1.8, OHZ 200 mg KOH / g polyetherol 1 prepared from propylene glycol and propylene oxide , Functionality 2, OH 100 mg KOH / g polyetherol 2 prepared from monoethylene glycol and ethylene oxide, functionality 2, OH 2 200 mg / KOH / g
- Catalyst 1 trimerization catalyst salt of a carboxylic acid dissolved in poly-ol
- Propellant 2 ZM 99 water in propylene glycol
- the prepolymer had an NCO content of 26.3 wt .-%, and a viscosity at 25 ° C of 1780 mPas.
- the prepolymer had an NCO content of 28.2 wt .-%, a viscosity at 25 ° C of 910 mPas and a content of 2-core MDI of 34.6 wt .-%.
- the prepolymer had an NCO content of 27.8 wt .-% and a viscosity at 25 0 C of 860 mPas and a content of 2-core MDI of 33.1 wt .-%.
- the viscosity of the prepolymers was determined with a Haake VT 500 rotary viscometer at 25 0 C directly after completion of the prepolymer synthesis (indicated Values).
- the NCO content of the prepolymers was also determined directly after completion of the synthesis as follows: The prepolymer was dissolved in N-methylpyrrolidone (NMP) and treated with an excess of di-n-hexylamine. The excess amine was back titrated with hydrochloric acid. The binuclear portion of the prepolymers was analyzed by gel chromatography (refractive index analysis). The analytical data obtained were converted into percent by weight after prior calibration with monomeric MDI.
- a polyol component was prepared by mixing.
- the polyol component and the prepolymer were foamed with the addition of catalyst and blowing agent in such a way that the setting time (thread drawing time) was 45 seconds and the apparent density was 45 g / l in each case.
- the NCO conversion was determined by means of IR spectroscopy.
- a test specimen was removed from the center and the edge of the sandwich elements produced by a reproducible method and measured by means of ATR-FTI R spectroscopy (Golden Gate arrangement).
- the absorbance (E) of the NCO band at 2270 cm 1 "1 a Aromatenreferenzbande at 1600 cm was to extinction" taken into consideration:
- the conversion was calculated on the basis of the decrease of the extinction ratio of the reacted system relative to an unreacted starting system (no catalyst):
- Table 2 Foamed Lupranat ® M 50 (Comparative Example 1) and prepolymer systems under constant experimental conditions.
- the sandwich elements for the evaluation of soil disorders were treated with a twin-belt temperature of 60 C and c con- stant quality sheet produced.
- the thermal conductivity (21, 4 mW / mK at 23 0 C according to DIN 52612) of the systems 1-9 was identical.
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Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
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JP2008505884A JP5121699B2 (ja) | 2005-04-14 | 2006-04-11 | 硬質ポリウレタン発泡体及び硬質ポリイソシアヌレート発泡体の製造方法 |
KR1020077026384A KR101323059B1 (ko) | 2005-04-14 | 2006-04-11 | 경질 폴리우레탄 및 폴리이소시아누레이트 발포체의 제조방법 |
US11/911,544 US20080188582A1 (en) | 2005-04-14 | 2006-04-11 | Method For Producing Polyurethane And Polyisocyanurate Rigid Foam |
CN2006800121298A CN101160333B (zh) | 2005-04-14 | 2006-04-11 | 生产聚氨酯和聚异氰脲酸酯硬质泡沫的方法 |
EP06725697.4A EP1874839B1 (de) | 2005-04-14 | 2006-04-11 | Verfahren zur herstellung von polyurethan- und polyisocyanurat-hartschaumstoffen |
ES06725697T ES2531328T3 (es) | 2005-04-14 | 2006-04-11 | Procedimiento para la preparación de materiales esponjados duros de poliuretano y poliisocianurato |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE102005017363.2 | 2005-04-14 | ||
DE102005017363A DE102005017363A1 (de) | 2005-04-14 | 2005-04-14 | Verfahren zur Herstellung von Polyurethan- und Polyisocyanurat-Hartschaumstoffen |
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WO2006108833A1 true WO2006108833A1 (de) | 2006-10-19 |
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PCT/EP2006/061506 WO2006108833A1 (de) | 2005-04-14 | 2006-04-11 | Verfahren zur herstellung von polyurethan- und polyisocyanurat-hartschaumstoffen |
Country Status (8)
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US (1) | US20080188582A1 (de) |
EP (1) | EP1874839B1 (de) |
JP (1) | JP5121699B2 (de) |
KR (1) | KR101323059B1 (de) |
CN (1) | CN101160333B (de) |
DE (1) | DE102005017363A1 (de) |
ES (1) | ES2531328T3 (de) |
WO (1) | WO2006108833A1 (de) |
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EP2208743A1 (de) * | 2009-01-17 | 2010-07-21 | Bayer MaterialScience AG | Reaktive Polyurethan Zusammensetzungen |
JP2011513568A (ja) * | 2008-03-14 | 2011-04-28 | ビーエーエスエフ ソシエタス・ヨーロピア | 粗い気泡のポリウレタンエラストマー |
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US8889756B2 (en) | 2009-03-18 | 2014-11-18 | Basf Se | Process for producing rigid polyurethane foams |
US9334383B2 (en) | 2011-04-15 | 2016-05-10 | Basf Se | Process for producing rigid polyurethane foams |
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WO2020030549A1 (de) | 2018-08-08 | 2020-02-13 | Covestro Deutschland Ag | Phosphinat als flammschutzadditiv für pur-/pir-hartschaumstoffe |
EP3719047A1 (de) | 2019-04-05 | 2020-10-07 | Covestro Deutschland AG | Verfahren zur herstellung von flammgeschützten pur-/pir-schaumstoffen |
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JP5677747B2 (ja) | 2007-01-09 | 2015-02-25 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 液化天然ガスタンクの断熱のための水−発泡性(water−blown)硬質フォーム |
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PL2956246T3 (pl) | 2013-02-13 | 2017-06-30 | Basf Se | Sposób wytwarzania elementów kompozytowych |
CN105246934A (zh) * | 2013-06-07 | 2016-01-13 | 科思创德国股份公司 | 具有改进的温度稳定性的弹性硬质泡沫 |
EP3601403B1 (de) * | 2017-03-28 | 2021-02-24 | Covestro Intellectual Property GmbH & Co. KG | Transluzente polyurethan- oder polyisocyanuratschaumstoffe |
ES2939727T3 (es) * | 2018-10-24 | 2023-04-26 | Basf Se | Espumas de poliuretano con contenido reducido de aminas aromáticas |
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EP3941955B1 (de) | 2019-03-19 | 2023-12-13 | Basf Se | Polyolkomponente und ihre verwendung zur herstellung von polyurethan-hartschaumstoffen |
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- 2006-04-11 WO PCT/EP2006/061506 patent/WO2006108833A1/de not_active Application Discontinuation
- 2006-04-11 KR KR1020077026384A patent/KR101323059B1/ko active IP Right Grant
- 2006-04-11 US US11/911,544 patent/US20080188582A1/en not_active Abandoned
- 2006-04-11 CN CN2006800121298A patent/CN101160333B/zh active Active
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CN101284901B (zh) * | 2007-04-12 | 2012-11-14 | 日本聚氨酯工业株式会社 | 多异氰酸酯组合物及使用其的硬质聚氨酯泡沫的制造方法 |
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JP2011513568A (ja) * | 2008-03-14 | 2011-04-28 | ビーエーエスエフ ソシエタス・ヨーロピア | 粗い気泡のポリウレタンエラストマー |
EP2208743A1 (de) * | 2009-01-17 | 2010-07-21 | Bayer MaterialScience AG | Reaktive Polyurethan Zusammensetzungen |
US8889756B2 (en) | 2009-03-18 | 2014-11-18 | Basf Se | Process for producing rigid polyurethane foams |
WO2012007418A1 (de) * | 2010-07-13 | 2012-01-19 | Bayer Materialscience Ag | Schwach modifizierte präpolymere und ihre anwendungen |
US9487616B2 (en) | 2010-07-13 | 2016-11-08 | Covestro Deutschland Ag | Lightly modified prepolymers and uses thereof |
WO2012140025A1 (de) | 2011-04-15 | 2012-10-18 | Basf Se | Verfahren zur herstellung von polyurethan-hartschaumstoffen |
WO2012140150A1 (de) | 2011-04-15 | 2012-10-18 | Basf Se | Verfahren zur herstellung von polyurethan-hartschaumstoffen |
US9334383B2 (en) | 2011-04-15 | 2016-05-10 | Basf Se | Process for producing rigid polyurethane foams |
WO2013127959A1 (de) | 2012-03-01 | 2013-09-06 | Basf Se | Polyurethan-hartschaumstoffe |
WO2013127647A1 (de) | 2012-03-01 | 2013-09-06 | Basf Se | Polyetheresterpolyole und ihre verwendung zur herstellung von polyurethan-hartschaumstoffen |
US9353234B2 (en) | 2012-03-01 | 2016-05-31 | Basf Se | Rigid polyurethane foams |
EP2634201A1 (de) | 2012-03-01 | 2013-09-04 | Basf Se | Polyurethan-Hartschaumstoffe |
WO2020030549A1 (de) | 2018-08-08 | 2020-02-13 | Covestro Deutschland Ag | Phosphinat als flammschutzadditiv für pur-/pir-hartschaumstoffe |
EP3719047A1 (de) | 2019-04-05 | 2020-10-07 | Covestro Deutschland AG | Verfahren zur herstellung von flammgeschützten pur-/pir-schaumstoffen |
WO2020201187A1 (de) | 2019-04-05 | 2020-10-08 | Covestro Intellectual Property Gmbh & Co. Kg | Verfahren zur herstellung von flammgeschützten pur-/pir-schaumstoffen |
WO2024038025A1 (de) | 2022-08-16 | 2024-02-22 | Basf Se | Neue polyurethan-schaumkatalysatoren mit verbesserter lagerstabilität |
Also Published As
Publication number | Publication date |
---|---|
KR20080007257A (ko) | 2008-01-17 |
JP5121699B2 (ja) | 2013-01-16 |
EP1874839A1 (de) | 2008-01-09 |
US20080188582A1 (en) | 2008-08-07 |
EP1874839B1 (de) | 2014-12-10 |
JP2008535989A (ja) | 2008-09-04 |
CN101160333B (zh) | 2011-06-15 |
ES2531328T3 (es) | 2015-03-13 |
KR101323059B1 (ko) | 2013-10-30 |
CN101160333A (zh) | 2008-04-09 |
DE102005017363A1 (de) | 2006-10-19 |
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