EP4536723A1 - Fabrication de mousse de polyuréthane ignifuge - Google Patents

Fabrication de mousse de polyuréthane ignifuge

Info

Publication number
EP4536723A1
EP4536723A1 EP23730477.9A EP23730477A EP4536723A1 EP 4536723 A1 EP4536723 A1 EP 4536723A1 EP 23730477 A EP23730477 A EP 23730477A EP 4536723 A1 EP4536723 A1 EP 4536723A1
Authority
EP
European Patent Office
Prior art keywords
parts
weight
foam
group
composition according
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
Application number
EP23730477.9A
Other languages
German (de)
English (en)
Inventor
Michael SUCHAN
Carsten Schiller
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Operations GmbH
Original Assignee
Evonik Operations GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Evonik Operations GmbH filed Critical Evonik Operations GmbH
Publication of EP4536723A1 publication Critical patent/EP4536723A1/fr
Pending legal-status Critical Current

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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
    • C08G18/28—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
    • C08G18/3215—Polyhydroxy compounds containing aromatic groups or benzoquinone 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
    • C08G18/36—Hydroxylated esters of higher fatty acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—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
    • C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
    • C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
    • 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
    • C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
    • C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
    • C08G18/4211—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols
    • C08G18/4216—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups derived from aromatic dicarboxylic acids and dialcohols from mixtures or combinations of aromatic dicarboxylic acids and aliphatic dicarboxylic acids and dialcohols
    • 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
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5003—Polyethers having heteroatoms other than oxygen having halogens
    • C08G18/5006—Polyethers having heteroatoms other than oxygen having halogens having chlorine and/or bromine atoms
    • C08G18/5012—Polyethers having heteroatoms other than oxygen having halogens having chlorine and/or bromine atoms having bromine atoms
    • 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
    • C08G18/6633—Compounds of group C08G18/42
    • C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • 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
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    • 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
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    • C08G18/6662—Compounds of group C08G18/42 with compounds of group C08G18/36 or hydroxylated esters of higher fatty acids 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
    • C08G18/28—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
    • C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • 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
    • C08G18/6696—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/36 or hydroxylated esters of higher fatty acids 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
    • 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
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K3/2279—Oxides; Hydroxides of metals of antimony
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/24—Acids; Salts thereof
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/32—Phosphorus-containing compounds
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/38—Boron-containing compounds
    • 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
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
    • 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
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
    • 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
    • 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
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2330/00—Thermal insulation material
    • 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
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    • C08K3/02—Elements
    • C08K2003/026—Phosphorus
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/32—Phosphorus-containing compounds
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    • 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
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    • C08K2003/321—Phosphates
    • C08K2003/328—Phosphates of heavy metals
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/38—Boron-containing compounds
    • C08K2003/387—Borates

Definitions

  • the present invention lies in the field of polyurethanes, preferably polyurethane foams, in particular rigid polyurethane foams.
  • polyurethanes preferably polyurethane foams, in particular rigid polyurethane foams.
  • it relates to the production of flame-retardant polyurethane foams, preferably flame-retardant rigid polyurethane foams using a combination of synergistic components, as well as compositions for producing such foams and furthermore the use of these foams.
  • polyurethane is understood to mean, in particular, a product obtainable by reacting a polyisocyanate component with a polyol component or compounds with isocyanate-reactive groups.
  • other functional groups such as uretdiones, carbodiimides, isocyanurates, allophanates, biurets, ureas and/or uretimines can also be formed. Therefore, for the purposes of the present invention, PU means both polyurethane and polyisocyanurate, polyureas and polyisocyanate reaction products containing uretdione, carbodiimide, allophanate, biuret and uretimine groups.
  • polyurethane foam is understood to mean foam which is obtained as a reaction product of a polyisocyanate component and a polyol component or compounds with isocyanate-reactive groups.
  • PU foam polyurethane foam
  • other functional groups such as allophanates, biurets, ureas, carbodiimides, uretdiones, isocyanurates or uretimines can also be formed.
  • PU rigid foam is a fixed technical term.
  • soft foam shows elastic behavior and therefore the deformation is reversible.
  • Hard foam on the other hand, is permanently deformed.
  • foam and foam are used synonymously within the meaning of this invention. This also applies to terms based on this, such as PU foam and PU foam, etc.
  • the amount of flame retardants used is generally increased.
  • the effects that can be achieved and the maximum possible amount used are limited by the fact that the flame retardants have a negative influence on the overall properties of the foam, such as its mechanical strength and/or the processing and production of the polyurethane foam.
  • the use of triethyl phosphate (TEP), tris(2-chloro-ethyl) phosphate (TCEP) or tris(1-chloro-2-propyl) phosphate (TCPP) usually has a strong plasticizing effect, which reduces the mechanical strength and thereby limiting the amount used.
  • the specific object of the present invention was to enable the provision of PU foams, in particular rigid PU foams, which meet increased requirements for flame retardancy, preferably according to KS F ISO 5660-1:2015-03, that is preferably a total heat release of a maximum of 8 MJ/m 2 and a heat release rate of a maximum of 200 kW/m 2 at a heating rate of 50 kW/m 2 and a test duration of 600 s, but do not or only slightly influence the processing and the foam properties.
  • red phosphorus and at least one polyisocyanate component, the composition having an index of at least 200.
  • An upper limit for the index can preferably be, for example, 1000, preferably 500.
  • composition according to the invention additionally contains at least one smoke reducer, preferably selected from the group consisting of antimony trioxide, zinc stannate, zinc hydroxystannate, zinc borate, calcium borate, zinc pyrophosphate, aluminum orthophosphate and aluminum phosphinate(s), with antimony trioxide and/or zinc borate being most preferred, so There is a particularly preferred embodiment of the invention.
  • a component or at least one component, such as a chemical compound, in the sense of this invention is selected from a group “consisting of” several components, such as several chemical compounds, this means in the sense of this invention, that each of the mentioned components of this group can be selected or mixtures of this group can also be selected.
  • flue gas reducers this means that, for example, zinc stannate or, for example, antimony trioxide, etc. can be selected, or, for example, antimony trioxide and zinc hydroxystannate or, for example, other mixtures can be selected.
  • composition according to the invention contains compound 1 and TCPP and/or TEP as well as antimony trioxide and/or zinc borate, then there is a further particularly preferred embodiment of the invention.
  • halogenated polyol in a total amount of 1 to 80 parts by weight, preferably 1.5 to 50 parts by weight, particularly preferably 2 to 40 parts by weight,
  • Flame retardants selected from (a) the group of phosphoric acid esters, preferably TCPP, TEP and/or TCEP and/or selected from (b) the group of phosphonates, preferably DMMP and/or DMPP, in a total amount of 2 to 60 parts by weight, preferably 5 to 50 parts by weight, particularly preferably 5 to 40 parts by weight,
  • a further particularly preferred embodiment of the invention is when the composition according to the invention is characterized in that, based on 100 parts by weight of the total halogen-free polyol component,
  • composition according to the invention contains water and/or formic acid, this represents a further particularly preferred embodiment of the invention.
  • composition according to the invention can also contain further optional additives, as are known from the prior art in connection with the production of polyurethanes, in particular PU foams, and are usually used.
  • a particularly preferred PU foam formulation, in particular rigid PU foam formulation, within the meaning of this invention has the composition mentioned in Table 1:
  • the composition according to the invention contains in particular the following components: a) polyol component, comprising at least one halogen-free polyester polyol and at least one halogenated polyol, b) polyisocyanate component (at least one polyisocyanate and/or polyisocyanate prepolymer) c ) Catalyst that catalyzes the reaction of isocyanate groups with OH, NH, or other isocyanate-reactive groups and/or the reaction of isocyanate groups with each other d) Optional foam stabilizer e) Blowing agent f) Flame retardant g) Optional further additives.
  • Polyether polyols can be prepared by known processes, for example by polymerizing alkylene oxides, preferably ethylene oxide, 1,3-propylene oxide, 1,2- or 2,3-butylene oxide, and/or tetrahydrofuran.
  • Preferred polyester polyols are based on esters of polyvalent aliphatic or aromatic carboxylic acids, preferably with 2 to 12 carbon atoms.
  • aliphatic carboxylic acids are succinic acid, glutaric acid, adipic acid, suberic acid, azelaic acid, sebacic acid, decanedicarboxylic acid, maleic acid and fumaric acid.
  • aromatic carboxylic acids are phthalic acid, isophthalic acid, terephthalic acid and the isomeric naphthalenedicarboxylic acids.
  • Preferred polyester polyols can be obtained in particular by condensation of these polyhydric carboxylic acids with polyhydric alcohols, preferably diols or triols with 2 to 12, particularly preferably with 2 to 6 carbon atoms, preferably trimethylolpropane, ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol and / or glycerin.
  • polyhydric alcohols preferably diols or triols with 2 to 12, particularly preferably with 2 to 6 carbon atoms, preferably trimethylolpropane, ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol and / or glycerin.
  • polyisocyanates with two or more isocyanate groups can generally be used as the polyisocyanate component (b).
  • Suitable polyisocyanates for the purposes of this invention are all organic isocyanates with two or more isocyanate groups, in particular the known aliphatic, cycloaliphatic, arylaliphatic and preferably aromatic polyvalent isocyanates.
  • the organic polyisocyanates can be used individually or in the form of mixtures.
  • Corresponding “oligomers” of diisocyanates can also be used, such as IPDI Trimer based on isocyanurate, biurete or urethdione.
  • prepolymers based on the above-mentioned isocyanates is possible.
  • Particularly suitable is the mixture of MDI and higher condensed analogues known as “polymeric MDI” (also referred to as “crude MDI” or “crude MDI”) with an average functionality of 2 to 4, as well as the various isomers of TDI in pure form or as a mixture of isomers.
  • a preferred ratio of total polyisocyanate component and total polyol component, expressed as an index of the formulation, i.e. as the stoichiometric ratio of isocyanate groups to isocyanate-reactive groups (e.g. OH groups, NH groups) multiplied by 100, is in the range of 200 to 1000, preferably 200 to 500.
  • An index of 100 represents a molar ratio of the reactive groups of 1 to 1.
  • the claimed composition has an index of at least 200.
  • catalysts known from the prior art can be used here, including, for example, amines (cyclic, acyclic; monoamines, diamines, oligomers with one or more amino groups), ammonium compounds, organometallic compounds and/or metal salts, preferably those of tin , iron, bismuth, potassium and/or zinc.
  • amines cyclic, acyclic; monoamines, diamines, oligomers with one or more amino groups
  • ammonium compounds preferably those of tin , iron, bismuth, potassium and/or zinc.
  • organometallic compounds and/or metal salts preferably those of tin , iron, bismuth, potassium and/or zinc.
  • mixtures of several such compounds can be used as catalysts.
  • Foam stabilizers (d) and their use in the production of PU foams are known to those skilled in the art.
  • the use of foam stabilizers is optional; one or more foam stabilizers are preferably used.
  • Surface-active compounds (surfactants) in particular can be used as foam stabilizers.
  • Foam stabilizers are preferably used in the production of PU foams. They can be used to optimize the desired cell structure and the foaming process.
  • one or more of the known Si-containing compounds can be used in particular, which support foam production (stabilization, cell regulation, cell opening, etc.). These compounds are well known from the prior art.
  • Particularly preferably, at least one foam stabilizer based on a polyethersiloxane can be used.
  • siloxane structures that can be used in the context of this invention are described, for example, in the following patent specifications, although their use is only described in classic PU foams (e.g. as molded foam, mattress, insulation material, construction foam, etc.): CN 103665385, CN 103657518, CN 103055759, CN 103044687, US 2008/0125503, US 2015/0057384, EP 1520870 A1, EP 1211279, EP 0867464, EP 0867465, EP 0275563.
  • Si can also -free surfactants are used.
  • One or more of the corresponding compounds with suitable boiling points and mixtures thereof can be used as physical blowing agents.
  • Physical blowing agents that can be used with preference have already been mentioned.
  • the preferred flame retardants (f), as already described, are at least one compound from the group of phosphoric acid esters, preferably TCPP, TEP and/or TCEP and/or from the group of phosphonates, preferably DMMP and/or DMPP, and additionally red phosphorus, preferably microencapsulated red phosphorus used.
  • Foams such as crosslinkers, chain extenders, stabilizers against oxidative degradation (so-called antioxidants), biocides, cell-refining additives, nucleating agents, cell openers, solid fillers, antistatic additives, thickeners, dyes, pigments, color pastes, fragrances and / or emulsifiers , etc.
  • composition according to the invention optionally contains so-called smoke gas reducers.
  • smoke gas reducers that can be used with preference have already been mentioned. These are advantageously characterized by the fact that, when used alone, they have no direct effect on flame retardancy, but sometimes significantly increase the effect of other flame retardants and/or reduce the development of smoke gases.
  • Flue gas reducers are known to those skilled in the art and include, for example, antimony trioxide, zinc hydroxystannate, zinc stannate, zinc borate, calcium borate or antimony pentoxide. These are also e.g. in Weil, Edward D. Levchik, Sergei V.
  • any preferred or particularly preferred embodiment of the invention may be combined with one or more of the other preferred or particularly preferred embodiments of the invention.
  • ranges general formulas or compound classes are given, these should include not only the corresponding ranges or groups of compounds that are explicitly mentioned, but also all sub-ranges and sub-groups of compounds that are obtained by removing individual values (ranges) or compounds can.
  • documents are quoted in the context of the present description, their content, in particular with regard to the matter in which the document was quoted, should belong entirely to the disclosure content of the present invention. Unless otherwise stated, percentages are in percent by weight. If mean values are given, so Unless otherwise stated, these are numerical averages. If parameters are stated that were determined by measurement, the measurements were carried out at a temperature of 23 °C and normal pressure, unless otherwise stated.
  • the formulations shown in Tables 2 and 3 were used for the application technology comparison.
  • the comparison foaming was carried out using the hand mixing process.
  • polyol component, catalysts, water, foam stabilizer, flame retardant, physical blowing agent and optionally other additives were weighed into a beaker and mixed with a plate stirrer (6 cm diameter) for 30 s at 1000 rpm (batch size 500 g).
  • the amount of blowing agent evaporated during the mixing process was determined by weighing again and replenished.
  • the fire behavior was determined using a cone calorimeter according to KS F ISO 5660-1:2015-03. For this purpose, 3 test specimens of 10x10x5 cm each were cut from each foam and the total heat release (“Total Heat Release” - THR in MJ/m 2 ) within 600 s, the maximum heat release rate (“Peak Heat Release Rate” - PHRR in kW/m 2 ) within 600 s, the mass loss during the burning time (in %) as well as the burning time (in s), more precisely, the time between ignition and extinguishing of the flame, was measured. The heating rate was 50 kW/m 2 . The arithmetic mean was determined from the values of the 3 test specimens. The test is considered passed if a THR ⁇ 8 MJ/m 2 and PHRR ⁇ 200 kW/m 2 were achieved. The results are shown in Tables 4 and 5.
  • Table 2 PU rigid foam formulations (composition in parts by weight)
  • Table 3 PU rigid foam formulations (composition in parts by weight)

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention concerne une composition destinée à la fabrication de mousse polyuréthane (PU), de préférence de mousse PU dure, ladite composition comprenant au moins un polyester polyol exempt d'halogène et au moins un polyol halogéné, au moins un agent gonflant physique, au moins un agent ignifuge choisi parmi (a) le groupe des esters d'acide phosphorique, de préférence le TCPP, le TEP et/ou le TCEP, en particulier le TCPP et/ou le TEP, et/ou (b) le groupe des phosphonates, de préférence le DMMP et/ou le DMPP, le phosphore rouge, ainsi qu'au moins un composant polyisocyanate, ladite composition présentant un indice d'au moins 200.
EP23730477.9A 2022-06-08 2023-06-02 Fabrication de mousse de polyuréthane ignifuge Pending EP4536723A1 (fr)

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PCT/EP2023/064765 WO2023237418A1 (fr) 2022-06-08 2023-06-02 Fabrication de mousse de polyuréthane ignifuge

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KR20250022121A (ko) 2025-02-14

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