EP3820923A1 - Reaktionssystem für einen 1-k polyurethan-hartschaumstoff - Google Patents
Reaktionssystem für einen 1-k polyurethan-hartschaumstoffInfo
- Publication number
- EP3820923A1 EP3820923A1 EP19735573.8A EP19735573A EP3820923A1 EP 3820923 A1 EP3820923 A1 EP 3820923A1 EP 19735573 A EP19735573 A EP 19735573A EP 3820923 A1 EP3820923 A1 EP 3820923A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- component
- weight
- reaction system
- isocyanate
- reactive
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
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- 238000000034 method Methods 0.000 claims abstract description 16
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- 239000004721 Polyphenylene oxide Substances 0.000 claims description 53
- -1 carbonate polyol Chemical class 0.000 claims description 49
- 150000003077 polyols Chemical class 0.000 claims description 39
- 239000004604 Blowing Agent Substances 0.000 claims description 29
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- 239000003054 catalyst Substances 0.000 claims description 27
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- 239000003381 stabilizer Substances 0.000 claims description 11
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- 230000008569 process Effects 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 9
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- 229910002092 carbon dioxide Inorganic materials 0.000 description 5
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 5
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- BCJPEZMFAKOJPM-UHFFFAOYSA-N 2-ethyl-3-methyloxirane Chemical compound CCC1OC1C BCJPEZMFAKOJPM-UHFFFAOYSA-N 0.000 description 3
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- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
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- 229920001577 copolymer Polymers 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
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- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
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- 239000001294 propane Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
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- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 2
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- KVMPUXDNESXNOH-UHFFFAOYSA-N tris(1-chloropropan-2-yl) phosphate Chemical compound ClCC(C)OP(=O)(OC(C)CCl)OC(C)CCl KVMPUXDNESXNOH-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
-
- 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
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2081—Heterocyclic amines; Salts thereof containing at least two non-condensed heterocyclic rings
-
- 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
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation 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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/166—Catalysts not provided for in the groups C08G18/18 - C08G18/26
-
- 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
- C08G18/44—Polycarbonates
-
- 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
- C08G18/4825—Polyethers 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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4829—Polyethers containing at least three 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
-
- 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
- C08J9/14—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 organic
- C08J9/141—Hydrocarbons
-
- 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
- C08J9/14—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 organic
- C08J9/142—Compounds containing oxygen but no halogen atom
-
- 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
- C08J9/14—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 organic
- C08J9/149—Mixtures of blowing agents covered by more than one of the groups C08J9/141 - C08J9/143
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
- C08K5/5419—Silicon-containing compounds containing oxygen containing at least one Si—O bond containing at least one Si—C bond
-
- 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
- C08G2110/0025—Foam properties rigid
-
- 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
- C08J2205/00—Foams characterised by their properties
- C08J2205/10—Rigid foams
-
- 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
- C08J2375/08—Polyurethanes from polyethers
Definitions
- the present invention relates to a one-component reaction system (also called 1-component reaction system) containing polyether carbonate polyol for the production of rigid polyurethane foams (also called rigid PU foams), and to processes for the production thereof and their use.
- the invention also relates to the rigid polyurethane foams produced from the one-component reaction system according to the invention.
- CCk-based raw materials for example in the form of polyether carbonate polyols, in relatively large quantities.
- the production of polyether carbonate polyols by catalytic conversion of alkylene oxides (epoxides) and carbon dioxide in the presence of H-functional starter compounds (“starters”) has been intensively investigated for more than 40 years (e.g. Inoue et al, Copolymerization of Carbon Dioxide and Epoxides with Organometallic Com pounds; Die Makromolekulare Chemie 130, 210-220, 1969).
- a prepolymer containing isocyanate groups is produced by reacting a polyol component with the addition of foam stabilizers and catalysts and, if appropriate, plasticizers, flame retardants, crosslinking agents and other additives with organic di- and / or polyisocyanates. This reaction normally takes place in the presence of blowing agents in a pressure vessel.
- the polyurethane foam can then be dispensed in a metered manner via a valve.
- the polyurethane foam first has a creamy consistency and then hardens by exposure to ambient humidity, for example from the air with a volume increase.
- Such foams are therefore referred to as one-component foams (1-component foams).
- the foam e.g. To obtain hardness or cell quality, a significant excess of the isocyanate is used compared to the polyol component. In this way, the so-called pre-extension and thus the molecular weight distribution of the prepolymer is regulated. The lower the pre-extension of the prepolymer, the narrower the molecular weight distribution and the more precisely adjustable the end properties of the cured PUR foam are.
- IC foams A large area of application for IC foams is the construction industry, in which rigid PU foams with good dimensional stability (low swelling or shrinkage) are desired. Rigid PUR foams with little swelling or shrinkage are characterized by the fact that foamed components have to be reworked less in a further work step (e.g. by cutting). There is also the risk that foamed components will change their geometry due to excessive swelling or shrinkage of the foam. In addition, foams with less swelling or shrinkage can be metered better.
- WO 2011/138274 A1 discloses prepolymers which are obtained by reacting polyisocyanates and polyether carbonate diols. These prepolymers can be used to e.g. to produce one-component coatings with improved hardness.
- WO 2011/138274 A1 does not disclose a one-component reaction system which leads to rigid polyurethane foams and thus also has no effect on the dimensional stability of rigid polyurethane foams from one-component reaction systems.
- the object of the present invention was to provide an IC polyurethane formulation which provides rigid polyurethane foams which can be easily discharged and at the same time are solid after curing and which have good dimensional stability.
- This object was surprisingly achieved by the one-component reaction system according to the invention for the production of rigid polyurethane foams, comprising the following constituents:
- the invention further relates to a method for producing a one-component reaction system, a method for producing rigid polyurethane foams from a one-component reaction system, a rigid polyurethane foam obtainable from a one-component reaction system, the use of a one-component reaction system as a one-component assembly foam (also called lK assembly foam), as well as a pressure vessel containing a one-component reaction system and a blowing agent.
- a one-component assembly foam also called lK assembly foam
- the equivalent weight indicates the ratio of the number average molecular weight and the functionality of the isocyanate-reactive component.
- the details of the equivalent weight for mixtures are calculated from the equivalent weights of the individual components in their molar proportions and relate to the number-average equivalent weight of the mixture.
- “molecular weight” or “molecular weight” means the number-weighted average molecular weight.
- the key figure (index) gives the percentage ratio of the amount of isocyanate actually used to the stoichiometric, i.e. amount of isocyanate group (NCO) amount calculated for the conversion of the OH equivalents.
- Aromatic polyisocyanates are used as organic polyisocyanate component A) in a proportion of 90 to 100% by weight, preferably 95 to 100% by weight, particularly preferably 98 to 100% by weight, based on the total weight of A).
- TDI 2,4- or 2,6-tolylene diisocyanate
- 1,5-naphthylene diisocyanate 2,2'- or 2,4'- or 4,4'-diphenylmethane diisocyanate
- 2,2'- or 2,4'- or 4,4'-diphenylmethane diisocyanate diomeric MDI
- polymeric MDI polymeric MDI
- 1,3- or l 4-bis (2-isocyanato-prop-2-yl) benzene
- TMXDI 2-bis (2-isocyanato-prop-2-yl) benzene
- XDI 3-bis (isocyanatomethyl) benzene
- other aromatic organic polyisocyanates from the polyurethane
- the organic polyisocyanate component A) preferably contains at least 80% by weight, particularly preferably at least 85% by weight and particularly preferably at least 95% by weight, based on the total weight of A), of monomeric and / or polymeric MDI.
- the organic polyisocyanate component contains
- organic polyisocyanate component A) in the one-component reaction system is preferably 30 to 80% by weight, particularly preferably 35 to 75% by weight, particularly preferably 40 to 70% by weight, in each case based on A) +
- the isocyanate-reactive component B) is such a component whose isocyanate-reactive functional groups are exclusively those with at least one Zerewitin-off-reactive hydrogen atom.
- the isocyanate-reactive component B) contains at least one polyether carbonate polyol in a proportion of at least 15% by weight, preferably at least 18% by weight, particularly preferably at least 20% by weight, particularly preferably at least 22% by weight, based on the total the proportions by weight from A) to F) in the one-component reaction system.
- polyether carbonate polyols such as, for example, polyether polyols, polyester polyols and / or polyether ester polyols can be contained in the isocyanate-reactive component B).
- Polyether carbonate polyols are prepared by addition of alkylene oxide and carbon dioxide onto one or more H-functional starter compounds in the presence of a double metal cyanide catalyst (DMC catalyst) or a metal complex catalyst based on the metals zinc and / or cobalt, preferably by the steps:
- DMC catalyst double metal cyanide catalyst
- metal complex catalyst based on the metals zinc and / or cobalt
- step ( ⁇ ) optionally adding a portion (based on the total amount of alkylene oxide used in the activation and copolymerization) of alkylene oxide to the mixture resulting from step (a) to activate a DMC catalyst, this addition of a portion of alkylene oxide optionally can take place in the presence of CO 2 , and then the temperature peak ("hotspot") occurring due to the following exothermic chemical reaction and / or a pressure drop in the reactor is respectively waited for, and the step (ß) for activation can also take place several times .
- a portion based on the total amount of alkylene oxide used in the activation and copolymerization
- alkylene oxides (epoxides) having 2 to 24 carbon atoms can be used to produce a polyether carbonate polyol.
- the alkylene oxides with 2 to 24 carbon atoms are, for example, one or more compounds selected from the group consisting of ethylene oxide, propylene oxide, 1-butene oxide, 2,3-butene oxide, 2-methyl-1,2-propene oxide (isobutene oxide ), 1-pentene oxide, 2,3-pentene oxide, 2-methyl-1, 2-butene oxide, 3-methyl-1, 2-butene oxide, 1-hexene oxide, 2,3-hexene oxide, 3,4-hexene oxide, 2- Methyl-l, 2-pentene oxide, 4-methyl-l, 2-pentene oxide, 2-ethyl-1, 2-butene oxide, 1-heptene oxide, 1-octene oxide, 1-nonoxide, 1-decene oxide, 1- undecene oxide, 1- Dodecene oxide, 4-methyl-l, 2-pen
- alkylene oxides are ethylene oxide and / or propylene oxide and / or 1,2-butylene oxide, particularly preferably propylene oxide.
- H-functional starter compound Compounds with H atoms active for the alkoxylation can be used as a suitable H-functional starter compound.
- Groups with active egg atoms which are active for the alkoxylation are, for example, -OH, -NH2 (primary amines), -NH- (secondary amines), -SH and - CO2H, preferred are -OH and -NH2, particularly preferred is -OH.
- Alcohols, amines, thiols and carboxylic acids can be used as monofunctional starter compounds.
- the following can be used as monofunctional alcohols: methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, t-butanol, 3-buten-1-ol, 3-butyn-1-ol, 2- Methyl-3-buten-2-ol, 2-methyl-3-butyn-2-ol, propyl alcohol, 2-methyl-2-propanol, lt-butoxy-2-propanol., 1-pentanol, 2-pentanol, 3rd -Pentanol, 1-hexanol, 2-hexanol, 3-hexanol, 1-heptanol, 2-heptanol, 3-heptanol, 1-octanol, 2-octanol, 3-octanol, 4-octanol, phenol, 2-hydroxyb
- amines Possible monofunctional amines are: butylamine, t-butylamine, pentylamine, hexylamine, aniline, aziridine, pyrrolidine, piperidine, morpholine.
- Monofunctional thiols which can be used are: ethanethiol, 1-propanethiol, 2-propanethiol, 1-butanethiol, 3-methyl-l-butanethiol, 2-butene-l-thiol, thiophenol.
- monofunctional carboxylic acids formic acid, acetic acid, propionic acid, butyric acid, fatty acids such as stearic acid, palmitic acid, oleic acid, linoleic acid, linoleic acid, benzoic acid, acrylic acid.
- Polyhydric alcohols suitable as H-functional starter compounds are, for example, two polyhydric alcohols (such as, for example, ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, 1,3-propanediol, 1,4-butanediol, 1,4-butenediol, 1,4-butynediol, Neopentyl glycol, 1,5-pentantanediol, methylpentanediols (such as 3-methyl-l, 5-pentanediol), 1,6-hexanediol, 1,8-octanediol, 1,10-decanediol, 1,12-dodecanediol, bis- ( hydroxymethyl) cyclohexanes (as in example 1,4-bis (hydroxymethyl) cyclohexane), triethylene glycol, tetraethylene glycol, polyethylene glycols, dipropylene glycol,
- the H-functional starter compounds can also be selected from the substance class of polyether polyols, in particular those with a molecular weight M n in the range from 100 to 4000 g / mol, preferably 250 to 2000 g / mol. Preference is given to polyether polyols which are composed of repeating ethylene oxide and propylene oxide units, preferably in a proportion of 35 to 100% propylene oxide units, particularly preferably in a proportion of 50 to 100% propylene oxide units. These can be statistical copolymers, gradient copolymers, alternating or block copolymers of ethylene oxide and propylene oxide.
- Suitable polyether polyols composed of repeating propylene oxide and / or ethylene oxide units are, for example, the Desmophen®, Acclaim®, Arcol®, Baycoll®, Bayfill®, Bayflex®, Baygal®, PET® and polyethers -Polyols from Covestro GmbH AG (such as Desmophen® 3600Z, Desmophen® 1900U, Acclaim® Polyol 2200, Acclaim® Polyol 40001, Arcol® Polyol 1004, Arcol® Polyol 1010, Arcol® Polyol 1030, Arcol® Polyol 1070, Baycoll® BD 1110, Bayfill® VPPU 0789, Baygal® K55, PET® 1004, Polyether® S180).
- Covestro Deutschland AG such as Desmophen® 3600Z, Desmophen® 1900U, Acclaim® Polyol 2200, Acclaim® Polyol 40001, Arcol® Polyol 1004, Arcol® Polyol 1010, Arcol® Polyol
- suitable homo-polyethylene oxides are for example the Pluriol® E brands from BASF SE
- suitable homo-polypropylene oxides are for example the Pluriol® P brands from BASF SE
- suitable mixed copolymers of ethylene oxide and propylene oxide are for example the Pluronic® PE or Pluri ol® RPE brands from BASF SE.
- the H-functional starter compounds can also be selected from the substance class of the polyester polyols, in particular those with a molecular weight M n in the range from 200 to 4500 g / mol, preferably 400 to 2500 g / mol.
- At least difunctional polyesters are used as polyester polyols. Polyester polyols preferably consist of alternating acid and alcohol units. As acid components such. B.
- succinic acid maleic acid, maleic anhydride, adipic acid, phthalic anhydride, phthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid, tetrahydrophthalic anhydride, hexahydrophthalic anhydride or mixtures of the acids and / or anhydrides mentioned.
- alcohol components such. B.
- ethanediol 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, neopentyl glycol, 1,6-hexanediol, l, 4-bis (hydroxymethyl) cyclohexane, diethylene glycol, Dipropylene glycol, trimethyl olpropane, glycerol, pentaerythritol or mixtures of the alcohols mentioned are used. If divalent or polyvalent polyether polyols are used as the alcohol component, polyester ether polyols are obtained which can also serve as starter compounds for the preparation of the polyether carbonate polyols.
- polyether polyols are used to prepare the polyester ether polyols, polyether polyols with a number-average molecular weight M n of 150 to 2000 g / mol are preferred.
- polycarbonate polyols can be used as H-functional starter compounds, in particular those with a molecular weight M n in the range from 150 to 4500 g / mol, preferably 500 to 2500, which are obtained, for example, by conversion of phosgene, dimethyl carbonate, Diethyl carbonate or diphenyl carbonate and di- and / or polyfunctional alcohols or polyester polyols or polyether polyols can be produced.
- polycarbonate polyols can be found e.g. B. in EP-A 1359177.
- Desmophen® C types from Covestro GmbH AG can be used as polycarbonate diols, such as. B. Desmophen® C 1100 or Desmophen® C 2200.
- component B) can contain proportions of other polyols, e.g. Contain polyether polyols, polyester polyols and / or polyether ester polyols.
- the polyether polyols are preferably polyhydroxy polyethers which can be prepared in a manner known per se by polyaddition of the alkylene oxides already described above to polyfunctional starter compounds in the presence of catalysts.
- the polyhydroxy polyethers are preferably prepared from a starter compound having an average of 2 to 8 active hydrogen atoms and one or more alkylene oxides.
- Preferred starter compounds are molecules with two to eight hydroxyl groups per molecule such as water, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, tripropylene glycol, 1,4-butanediol, 1,6-hexanediol, triethanolamine, glycerol, trimethylolpropane, pentaerythritol, sorbitol and sucrose.
- the starter compounds can be used alone or in a mixture.
- the starter compound is produced with an alkylene oxide, preferably with ethylene oxide and / or propylene oxide. When used in a mixture, it is possible to implement the alkylene oxides statistically and / or in blocks.
- High molecular weight polyhydroxy polyethers in which high molecular weight polyadducts or polycondensates or polymerizates are present in finely dispersed, dissolved or grafted form are also suitable.
- Modified poly hydroxyl compounds of this type are obtained, for example, if polyaddition reactions (for example reactions between polyisocyanates and amino-functional compounds) or polycondensation reactions (for example between formaldehyde and phenols and / or amines) are carried out in situ in the compounds containing hydroxyl groups (as for example in DE-AS 1 168 075).
- Polyhydroxyl compounds modified by vinyl polymers as obtained, for example, by polymerizing styrene and acrylonitrile in the presence of polyethers (for example in accordance with US Pat. No. 3,383,351), are suitable for the process according to the invention as isocyanate-reactive component B).
- isocyanate-reactive component B Representatives of the component B) mentioned are described, for example, in the plastics manual, volume VII “Polyurethane”, 3rd edition, Carl Hanser Verlag, Kunststoff / Vienna, 1993, pages 57-67 and pages 88-90.
- a polyether carbonate polyol with a functionality of 1.0 to 4.0, particularly preferably 1.5 to 3.5, particularly preferably 1.9 to 3.0 is preferably used.
- the hydroxyl number of the polyether carbonate polyol can be, for example, 10 to 800 mg KOH / g, preferably 25 to 500 mg KOH / g, particularly preferably 50 to 300 mg KOH / g, particularly preferably 100 to 250 mg KOH / g.
- the compounds used as isocyanate-reactive component B) can also be present as prepolymers.
- a prepolymer can be produced in any manner known to the person skilled in the art. In an advantageous embodiment, this is prepared by reacting at least one isocyanate-reactive component B) with an excess of the organic polyisocyanate compound A), optionally followed by partial distillation of the unreacted polyisocyanate compound A) to the desired free isocyanate content.
- Components A) and B) can be reacted in the presence of a catalyst component catalyzing the prepolymerization (“prepolymerization catalyst”), but the reaction is preferably not carried out in the presence of a prepolymerization catalyst or there are at most technically unavoidable traces of a prepolymerization catalyst present.
- prepolymerization catalyst a catalyst component catalyzing the prepolymerization
- the compounds described for use as isocyanate-reactive component B) can be used individually or as mixtures, the isocyanate-reactive compound being preferred
- the one-component reaction system also contains at least one foam stabilizer C).
- silicone-containing foam stabilizers such as siloxane-oxyalkylene copolymers and other organopolysiloxanes, furthermore alkoxylation products from fatty alcohols, oxoalcohols, fatty amines, alkylphenols, dialkylphenols, alkylcresols, alkylresorcinol, naphthol, alkylnaphthol, naphthylamine, bisphenylamine, anisole -A, alkylated bisphenol-A, polyvinyl alcohol, and also alkoxylation products of condensation products from formaldehyde and alkylphenols, formaldehyde and dialkylphenols, formaldehyde and alkylcresols, formaldehyde and alkylresorcinol, formaldehyde and aniline, formaldehyde and toluidine, formaldehyde and naphthol, formaldehyde and formaldehyde and formaldehyde and formaldeh
- foam stabilizers are those foam stabilizers which are selected from the group of polyether-polydialkoxysilane copolymers, the alkoxy groups being selected independently of one another in particular from aliphatic hydrocarbon radicals having one to ten carbon atoms, preferably from methyl, ethyl, n- Propyl or i-propyl residues.
- the foam stabilizer C) can have a cloud point of at least 40 ° C, in particular at least 50 ° C, preferably at least 60 ° C, measured in a 4% by weight aqueous solution of the foam stabilizer C) and gradually increasing the temperature of 20 ° C starting with a heating rate of 2 ° C / min and determination of the cloud point by visual assessment of the time of the onset of cloudiness.
- This is advantageous because the fire protection properties of the rigid polyurethane foams obtained can be further increased by using such foam stabilizers.
- the aforementioned values for the cloud point can alternatively also be determined nephelometrically using DIN EN ISO 7027 (2000) without being bound to the aforementioned procedure with a combined change in temperature.
- Foam stabilizers C) which have a high ratio of ethylene oxide to propylene oxide in the polyether side chains of the silicone-polyether copolymers and at the same time have a low ( ⁇ 5) dimethylsiloxane content are very particularly preferred.
- Formula (II) gives examples of this.
- A aryl, alkyl or H
- silicone stabilizers are available, for example, from Schill + Seilacher GmbH or Evonik Industries AG. Of these foam stabilizers, preferred are those whose OH number is in the range from 90 to 130 mg KOH / g (e.g. foam stabilizers 1 and 2). Table 1
- any catalyst known to be suitable for this purpose to the person skilled in the art can be used as catalyst D), with for example an amine catalyst.
- 2,2'-dimorpholinyl diethyl ether is preferred as catalyst D), since it catalyzes the reaction of the isocyanate with water in a particularly selective manner.
- the reaction system further contains as component E) at least one physical blowing agent with a boiling point ⁇ 0 ° C and optionally co-blowing agent.
- Hydrocarbons are preferred as blowing agents, especially the isomers of propane and butane.
- Physical blowing agents with a boiling point ⁇ 0 ° C. are preferred as co-blowing agents, which additionally have an emulsifying or solubilizing effect.
- Dimethyl ether is preferably used as co-blowing agent.
- dimethyl ether is used as the co-blowing agent and at least one compound selected from the group consisting of the isomers of propane and butane is used as the blowing agent.
- the reaction system may also contain other auxiliaries and additives F), e.g. Flame retardants, cell regulators, plasticizers and thinners, e.g. Long-chain chlorinated paraffins and paraffins, pigments or dyes, surface-active compounds and / or stabilizers against oxidative, thermal or microbial degradation or aging.
- auxiliaries and additives F e.g. Flame retardants, cell regulators, plasticizers and thinners, e.g. Long-chain chlorinated paraffins and paraffins, pigments or dyes, surface-active compounds and / or stabilizers against oxidative, thermal or microbial degradation or aging.
- the reaction system may further contain an acid, preferably with a pKa value of at least 0, or an acid derivative such as, for example, an acid chloride, preferably an acid chloride of an aromatic carboxylic acid, for example phthalic acid dichloride, in particular in an amount of 10 to 500 ppm, based on the amount of organic polyisocyanate component A), preferably from 50 to 300 ppm.
- an acid preferably with a pKa value of at least 0, or an acid derivative such as, for example, an acid chloride, preferably an acid chloride of an aromatic carboxylic acid, for example phthalic acid dichloride, in particular in an amount of 10 to 500 ppm, based on the amount of organic polyisocyanate component A), preferably from 50 to 300 ppm.
- the reaction system contains no short chain monooie or hydroxy ketones.
- short-chain means in particular those monooies or hydroxyketones which have a molecular weight of ⁇ 200 g / mol. Such compounds can act as cell openers, which is not desirable here.
- the invention relates to a one-component reaction system for the production of rigid polyurethane foams, comprising the following constituents:
- the invention relates to a one-component reaction system according to one of the embodiments 1 or 2, characterized in that component B) is a polyol with a functionality F n of 1.0 to 4.0, preferably 1.5 to 3, 5, particularly preferably 1.9 to 3.0, contains.
- component B) is a polyether polyol with an OH number of 50 to 300 mg KOH / g, preferably 75 to 275 mg KOH / g, particularly preferably 100 to 250 mg KOH / g, contains.
- the invention relates to a one-component reaction system according to one of the embodiments 1 to 4, characterized in that compounds having a structural formula (II) are used as foam stabilizer C)
- A aryl, alkyl or H can be used.
- the invention relates to a one-component reaction system according to one of the embodiments 1 to 5, comprising the following components: 30 to 70% by weight of organic polyisocyanate component A),
- the invention relates to a one-component reaction system according to one of the embodiments 1 to 6, characterized in that the isocyanate index is 350 to 550.
- the invention relates to a process for producing a one-component reaction system by reacting the organic polyisocyanate component A) with
- the isocyanate-reactive component B) is at least 10% by weight, based on the sum of the isocyanate-reactive component B
- Parts by weight from A) to F) 100% by weight of a polyether carbonate polyol.
- the invention relates to a process for producing a rigid polyurethane foam, obtainable by mixing and reacting components A) to F) of a one-component reaction system according to one of embodiments 1 to 7 under the action of moisture.
- the invention relates to a method for producing a rigid polyurethane foam, comprising the steps a) producing a one-component reaction system by a method according to the eighth embodiment and b) Exposure to moisture on the one-component reaction system produced in step a).
- the invention relates to a rigid polyurethane foam obtained by a process according to one of the embodiments 9 or 10.
- the invention relates to the use of a one-component reaction system according to one of the embodiments 1 to 7 as a 1-component assembly foam , wherein the one-component reaction system is filled in a pressure vessel.
- the invention relates to a pressure vessel, in particular a disposable pressure vessel, containing a one-component reaction system according to one of the embodiments 1 to 7.
- the invention relates to the use of rigid polyurethane foams according to the eleventh embodiment for applications in the construction industry.
- the rigid PUR foams according to the invention are produced by a two-stage process known to the person skilled in the art, in which the reaction components are reacted discontinuously with one another and then brought into or onto suitable molds / substrates / cavities for curing. Examples are in USA-A 2 761 565, in G. Oertel (ed.) "Kunststoff-Handbuch", Volume VII, Carl Hanser Verlag, 3rd edition, Kunststoff 1993, pp. 284 ff., And in K. Uhlig (Ed.) "Polyurethane Taschenbuch", Carl Hanser Verlag, 2nd edition, Vienna 2001, pp. 83-102.
- the hydroxyl numbers were measured by means of NfR spectroscopy (Lambda 950, Perkin-Elmer, PC-controlled). The combination vibrations of the v (OH) and d (OH) fundamental vibrations were measured in the range from 2050 to 2100 nm for the samples and calibration samples used in the examples. The samples and calibration samples were tempered to 20 ° C for the measurements. Polyether polyols were used as calibration samples, the OH number of which was determined in accordance with the standard DIN 53240-2 (1998). The results of the NIR spectroscopy of the samples were compared with the results of the calibration samples according to the Max-Min method and the OH number of the samples was determined therefrom.
- the EN ISO 11909 (2007) standard was used to determine the NCO content in the polyisocyanate.
- the required amount of the polyol components was placed in a mixing container in succession and mixed with appropriate amounts of catalyst, blowing agent and auxiliary and additive (Table 2). The mixture was then transferred to a disposable pressure vessel. The quantity of polyisocyanate corresponding to the characteristic number was then added to the can and this was sealed with a valve. The required amounts of propellant were added via the attached valve using an appropriate metering unit. Finally, the disposable pressure vessel was shaken until the IC formulation was completely homogenized.
- the 1K formulations thus prepared are given below in the examples in Table 3.
- the rigid PUR foam is discharged from the can into a mold (600 mm x 30 mm x 60 mm) which is lined with paper and sprayed with water. After 1 day, the resulting PUR rigid foam strand is removed from the mold. In the middle of the strand (at 300 mm) the thickness is measured with a thickness gauge. The ratio of the rigid PUR foam strand thickness to the mold width (30 mm) represents the dimensional stability (shrinkage / swelling). The thickness of the middle of the strand (at 300 mm) becomes another 7 days after foaming measured with a thickness gauge. The moisture required for curing is supplied by spraying the paper with water. This procedure is independent of the prevailing air humidity and provides the most reproducible results. All results for the 1-component reaction systems produced in accordance with the present application and the rigid polyurethane foams produced therefrom (free foaming) and their properties are summarized in Table 3.
- Examples 1, 3 and 5 were produced without using a polyether carbonate polyol and lead to severe swelling (example 1) or shrinkage (examples 3 and 5) of the rigid PU foam.
- Example 2 and 4 the replacement of the polyether polyols from Examples 1 and 3 with corresponding polyether carbonate polyols leads to a significantly reduced swelling or shrinkage of the rigid PU foams obtained.
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP18182568.8A EP3594256A1 (de) | 2018-07-10 | 2018-07-10 | Reaktionssystem für einen 1-k polyurethan-hartschaumstoff |
PCT/EP2019/068192 WO2020011685A1 (de) | 2018-07-10 | 2019-07-08 | Reaktionssystem für einen 1-k polyurethan-hartschaumstoff |
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EP3820923A1 true EP3820923A1 (de) | 2021-05-19 |
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EP18182568.8A Ceased EP3594256A1 (de) | 2018-07-10 | 2018-07-10 | Reaktionssystem für einen 1-k polyurethan-hartschaumstoff |
EP19735573.8A Pending EP3820923A1 (de) | 2018-07-10 | 2019-07-08 | Reaktionssystem für einen 1-k polyurethan-hartschaumstoff |
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EP18182568.8A Ceased EP3594256A1 (de) | 2018-07-10 | 2018-07-10 | Reaktionssystem für einen 1-k polyurethan-hartschaumstoff |
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US (1) | US20210253781A1 (de) |
EP (2) | EP3594256A1 (de) |
CN (1) | CN112513124A (de) |
WO (1) | WO2020011685A1 (de) |
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CN115785373A (zh) * | 2022-11-29 | 2023-03-14 | 佳化化学科技发展(上海)有限公司 | 一种聚氨酯硬泡及其制备方法和应用 |
Family Cites Families (12)
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US2761565A (en) | 1954-03-19 | 1956-09-04 | Clyde E Hutchinson | Filter units |
GB1022434A (en) | 1961-11-28 | 1966-03-16 | Union Carbide Corp | Improvements in and relating to polymers |
GB1053131A (de) | 1963-02-11 | |||
GB8528071D0 (en) | 1985-11-14 | 1985-12-18 | Shell Int Research | Polycarbonates |
DE10219028A1 (de) | 2002-04-29 | 2003-11-06 | Bayer Ag | Herstellung und Verwendung von hochmolekularen aliphatischen Polycarbonaten |
DE102010019504A1 (de) | 2010-05-06 | 2011-11-10 | Bayer Materialscience Ag | Polyisocyanatprepolymere und deren Verwendung |
CN103764703A (zh) * | 2011-03-28 | 2014-04-30 | 拜耳知识产权有限责任公司 | 制造聚氨酯-软质泡沫材料的方法 |
CN107298759A (zh) * | 2011-07-25 | 2017-10-27 | 诺沃梅尔公司 | 用于聚氨酯的脂族聚碳酸酯 |
US20170096539A1 (en) * | 2012-07-31 | 2017-04-06 | Covestro Deutschland Ag | Method for the production of polyurethane foam |
US20140275303A1 (en) * | 2013-03-15 | 2014-09-18 | Clayton Corporation | Rodent resistant polyurethane foams |
JP2018506633A (ja) * | 2015-02-27 | 2018-03-08 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトCovestro Deutschland Ag | 色安定性ポリウレタンフォームの製造のためのポリエーテルカーボネートポリオールの使用 |
EP3067376A1 (de) * | 2015-03-11 | 2016-09-14 | Evonik Degussa GmbH | Herstellung von Polyurethansystemen unter Einsatz von Polyetherpolycarbonatpolyolen |
-
2018
- 2018-07-10 EP EP18182568.8A patent/EP3594256A1/de not_active Ceased
-
2019
- 2019-07-08 CN CN201980046178.0A patent/CN112513124A/zh active Pending
- 2019-07-08 EP EP19735573.8A patent/EP3820923A1/de active Pending
- 2019-07-08 WO PCT/EP2019/068192 patent/WO2020011685A1/de unknown
- 2019-07-08 US US17/253,172 patent/US20210253781A1/en not_active Abandoned
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US20210253781A1 (en) | 2021-08-19 |
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WO2020011685A1 (de) | 2020-01-16 |
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