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WO2025131996A1 - Composé contenant des groupes hydroxyle oxymiques et son procédé de préparation - Google Patents

Composé contenant des groupes hydroxyle oxymiques et son procédé de préparation Download PDF

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Publication number
WO2025131996A1
WO2025131996A1 PCT/EP2024/085950 EP2024085950W WO2025131996A1 WO 2025131996 A1 WO2025131996 A1 WO 2025131996A1 EP 2024085950 W EP2024085950 W EP 2024085950W WO 2025131996 A1 WO2025131996 A1 WO 2025131996A1
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WIPO (PCT)
Prior art keywords
polyurethane
hydroxyl group
containing compound
acid
mol
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.)
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PCT/EP2024/085950
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German (de)
English (en)
Inventor
Lucilla LEVI
Joerg Hofmann
Klaus Lorenz
Stefan WERDA
Matthias LEVEN
Daniel RAPS
Johannes KIECHERER
Christian Mueller
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Covestro Deutschland AG
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Covestro Deutschland AG
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Filing date
Publication date
Priority claimed from EP23219543.8A external-priority patent/EP4574869A1/fr
Application filed by Covestro Deutschland AG filed Critical Covestro Deutschland AG
Publication of WO2025131996A1 publication Critical patent/WO2025131996A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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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
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic 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
    • C08G18/48—Polyethers
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
    • C08G65/2615—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen the other compounds containing carboxylic acid, ester or anhydride 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
    • C08G65/2618—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00—Foam properties
    • C08G2110/0008—Foam properties flexible

Definitions

  • the present invention relates to a compound containing oximic hydroxyl groups and a process for its preparation. Furthermore, the invention extends to a process for producing a polyurethane comprising reacting the compound containing oximic hydroxyl groups, the resulting polyurethanes, and a thermal treatment of this polyurethane.
  • a disadvantage of chemolysis processes is the use of excess water or alcohols, whereby these reactants or possibly additional solvents must be separated, for example, through downstream energy-intensive distillative process steps, which increases the process complexity and time required. Furthermore, before any PU recycling can take place, the resulting polyol phase must be separated from the carbamate phase and purified, or the resulting carbamate must be cleaved to the amine in additional, (safety-)technically complex process steps and converted into the isocyanate component by phosgenation.
  • the object of the present application was to provide compounds containing hydroxyl groups as a polyol component for the production of a polyurethane by reaction with a polyisocyanate component to form urethane bonds, wherein an improved reuse of the polyurethane compared to the prior art is made possible, for example by a preferably reversible cleavage and re-linking of at least some of the urethane bonds and thus the reuse of the polyurethane without completely splitting the overall polyurethane structure, as occurs in chemolysis processes known from the prior art by reaction with alcohols and/or water.
  • complex recycling processes using various additional reactants or Solvents and their separation for example by using energy-intensive, thermal and/or extractive separation methods, are avoided.
  • the polyurethanes produced using the novel hydroxyl-containing compounds as a polyol component have at least comparable property profiles, such as mechanical properties, to polyurethanes produced using known polyol components.
  • a hydroxyl group-containing compound (A) wherein at least some of the hydroxyl groups are oximic hydroxyl groups, wherein the hydroxyl group-containing compound (A) is composed of the elements carbon, hydrogen, oxygen and nitrogen, wherein the hydroxyl group-containing compound (A) has an OH number (determined by means of DIN 4629-2 (December 2016)) of 10 mg KOH/g to 600 mg KOH/g, preferably of 12 mg KOH/g to 500 mg KOH/g, and wherein the hydroxyl group-containing compound (A) contains oxypropylene units, achieves the above-mentioned object.
  • the hydroxyl group-containing compound (A) contains at least 3 directly consecutive oxypropylene units.
  • the hydroxyl group-containing compound (A) contains at most 200 directly consecutive oxypropylene units.
  • the OH number of the hydroxyl group-containing compound (A) is from 12 mg KOH/g to 500 mg KOH/g, particularly preferably from 15 mg KOH/g to 500 mg KOH/g.
  • the calculated proportion of oximic hydroxyl groups is from 20 mol% to 100 mol%, preferably from 25 mol% to 100 mol%, particularly preferably from 30 mol% to 100 mol%, and most preferably from 35 mol% to 100 mol%, based on the sum of all free hydroxyl groups of the hydroxyl-containing compound (A).
  • the hydroxyl group-containing compound (A) has a calculated hydroxyl group functionality of 1 to 8, preferably of 2 to 6 and particularly preferably of 2 to 4.
  • the invention also relates to a process for preparing the hydroxyl group-containing compound (A) according to the invention, comprising the steps: i) reacting a component (B) containing one or more aliphatic hydroxyl group(s) with a component (C) containing (C-1) one or more hydroxyl group-reactive functional group(s) and (C-2) one or more carbonyl group(s), optionally in the presence of a catalyst (D) to form an intermediate (E), and ii) reacting the intermediate (E) with hydroxylamine and/or salts of hydroxylamine, preferably hydroxylamine.
  • aliphatic hydroxyl groups are understood, in accordance with common technical knowledge, to be hydroxyl groups that are directly bonded to alkylene groups, such as CtU groups. Thus, aryl hydroxyl groups are excluded.
  • the aliphatic hydroxyl groups of component (B) are primary and/or secondary hydroxyl groups.
  • component (B) is obtainable by reacting an H-functional starter compound (F) with an alkylene oxide (G) in the presence of a catalyst (H).
  • component (B) is obtained by reacting an H-functional starter compound (F) with an alkylene oxide (G) in the presence of a catalyst (H).
  • component (C) containing (C-1) one or more hydroxyl group-reactive functional group(s) and (C-2) one or more carbonyl group(s) contains a carboxylic acid group and/or a carboxylic acid chloride group, a carboxylic acid ester group, preferably a carboxylic acid group.
  • the component (C) containing (C1) one or more hydroxyl group-reactive functional group(s) and (C-2) one or more carbonyl group(s) is an aliphatic component (C) which is composed only of aliphatic units, ie no aromatic units such as phenyl groups.
  • component (C) containing (C1) one or more hydroxyl group-reactive functional group(s) and (C2) one or more carbonyl group(s) is one or more compounds and is selected from the group consisting of levulinic acid, acetoacetic acid, pyruvic acid, a-methyllevulinic acid, 3-methyl-4-oxopentanoic acid, 4-oxo-2-propyl-pentanoic acid, 2-acetyl-4-methylpentanoic acid, preferably levulinic acid, acetoacetic acid and pyruvic acid.
  • catalysts (D) can be added to the reaction of component (B) containing one or more aliphatic hydroxyl groups with a component (C) containing one or more hydroxyl-reactive functional groups and one or more carbonyl groups.
  • component (C) containing one or more hydroxyl-reactive functional groups and one or more carbonyl groups.
  • carboxylic acid groups as hydroxyl-reactive functional groups of component (C)
  • a corresponding esterification with component (B) containing one or more aliphatic hydroxyl groups would take place.
  • Esterification catalysts can be used for this purpose, including, for example, tin(II) salts such as tin dichloride, tin dichloride dihydrate, tin(II) 2-ethylhexanoate, dibutyltin dilaurate, titanium alkoxylates such as titanium tetrabutoxide, tetraisopropyl titanate, bismuth(III) neodecanoate, zinc(II) acetate, manganese(II) acetate, or protic acids such as p-toluenesulfonic acid.
  • the esterifications can also be catalyzed by enzymes such as esterases and/or lipases.
  • the catalyst (D) is one or more compounds and is selected from the group consisting of tin dichloride, tin dichloride dihydrate, tin(II) 2-ethylhexanoate, dibutyltin dilaurate, titanium tetrabutoxide, tetraisopropyl titanate, bismuth(III) neodecanoate, zinc(II) acetate, manganese(II) acetate and p-toluenesulfonic acid, preferably p-toluenesulfonic acid.
  • the intermediate (E) is formed in step i) by reacting the component (B) containing one or more aliphatic hydroxyl group(s) with the component (C) containing (C-1) one or more hydroxyl group-reactive functional group(s) and (C-2) one or more carbonyl group(s), optionally in the presence of the catalyst (D).
  • Suitable H-functional starter compounds (F), also called starters, are compounds containing H atoms active for alkoxylation, so-called "Zerewitinoff-active" hydrogen atoms.
  • a hydrogen bonded to N, O, or S is referred to as Zerewitinoff-active hydrogen if, according to a process discovered by Zerewitinoff, it yields methane by reaction with methylmagnesium iodide.
  • Typical examples of compounds containing Zerewitinoff-active hydrogen are compounds containing carboxyl, hydroxyl, or amino groups as functional groups.
  • the H-functional starter compound (F) in the process according to the invention preferably contains no sulfur-containing functional groups, in particular no thiol groups. Groups with active H atoms that are particularly suitable for alkoxylation are -OH and -NH2, -OH is particularly preferred.
  • H-functional starter compound (F) for example, one or more compounds can be selected from the group comprising mono- or polyhydric alcohols, polyhydric amines, amino alcohols, hydroxyesters, polyether polyols, polyester polyols, polyester ether polyols, polyether carbonate polyols, polycarbonate polyols, polycarbonates, polyethyleneimines, polyetheramines (e.g. so-called Jeffamine® from Huntsman, such as D-230, D-400, D-2000, T-403, T-3000, T-5000 or corresponding products from BASF, such as Polyetheramine D230, D400, D200, T403, T5000), polytetrahydrofurans (e.g.
  • C1-C23 alkyl fatty acid esters that contain an average of at least 2 OH groups per molecule
  • commercial products such as Lupranol Balance® (BASF AG), Merginol® grades (Hobum Oleochemicals GmbH), Sovermol® grades (Cognis Deutschland GmbH & Co. KG), and Soyol®TM grades (USSC Co.).
  • H-functional starter compounds (F) are, for example, dihydric alcohols such as 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-1,5-pentanediol), 1,6-hexanediol, 1,8-octanediol, 1,10-decanediol, 1,12-dodecanediol, bis-(hydroxymethyl)-cyclohexanes (such as 1,4-bis-(hydroxymethyl)-cyclohexane), triethylene glycol, tetraethylene glycol, polyethylene glycols, dipropylene glycol, tripropylene glycol, poly(ethylene
  • the invention also provides the hydroxyl-containing compound (A) obtainable by the process according to the invention.
  • the compound (A) is sulfur-free.
  • the polyurethane (I) is a polyurethane foam (1-1), wherein the reaction takes place in the presence of a blowing agent (L), preferably water and/or a physical blowing agent.
  • a blowing agent preferably water and/or a physical blowing agent.
  • the polyurethane foam (I-1) is a flexible polyurethane foam (I-1a), a rigid polyurethane foam (I-1b) or a viscoelastic Polyurethane foam (I-lc), whereby the aforementioned foams can be produced using processes known to the person skilled in the art.
  • the flexible polyurethane foam (I-1a) is produced at a density of 90 to 120, wherein the production takes place in the presence of the blowing agent (L) which contains 0.8 to 4.5 parts by weight of water, based on the sum of the parts by weight of components (I-1) and (I-2), wherein the sum of the parts by weight of components (I-1) and (I-2) is 100.
  • the density is defined as the ratio of isocyanate groups to hydroxyl groups multiplied by a factor of 100, with one water molecule contributing 2 hydroxyl groups in this calculation.
  • Flexible polyurethane foams and their production processes are generally known to those skilled in the art, as described, for example, in G. Oertel (ed.): “Polyurethane Handbook", 2nd Edition, Carl-Hanser-Verlag, Kunststoff, Vienna 1993, pp. 177-246.
  • the rigid polyurethane foam (I-1b) is produced at a density of 90 to 600, the production being carried out in the presence of the blowing agent (L) which contains 5 to 25 parts by weight of a blowing agent, preferably a physical blowing agent such as pentane, based on the sum of the parts by weight of components (J-1) and (J-2), the sum of the parts by weight of components (J-1) and (J-2) being 100.
  • Rigid polyurethane foams and their production processes are generally known to the person skilled in the art, as described, for example, in G. Oertel (ed.): “Polyurethane Handbook”, 2nd Edition, Carl-Hanser-Verlag, Kunststoff, Vienna 1993, pp. 247-328.
  • polyoxyalkylene polyols suitable for this purpose can be obtained, for example, by anionic polymerization of alkylene oxides in the presence of alkali metal hydroxides or alkali metal alcoholates as catalysts and with the addition of at least one starter molecule containing 2 to 8 Zerewitinoff-active hydrogen atoms, or by cationic polymerization of alkylene oxides in the presence of Brönsted or Lewis acids such as trifluoromethanesulfonic acid, perchloric acid, antimony pentachloride, boron trifluoride etherate or tris(pentafluorophenyl)borane.
  • Brönsted or Lewis acids such as trifluoromethanesulfonic acid, perchloric acid, antimony pentachloride, boron trifluoride etherate or tris(pentafluorophenyl)borane.
  • polyoxyalkylene polyols in a weight ratio of 90:10 to 10:90, preferably 70:30 to 30:70, advantageously in the aforementioned further polyoxyalkylene polyols, and also polyoxyalkylene polyol dispersions which contain, as the disperse phase, usually in an amount of 1 to 50% by weight, preferably 2 to 25% by weight, inorganic fillers, polyureas, polyhydrazides, polyurethanes containing bonded tert-amino groups and/or melamine.
  • Suitable polyester polyols can be prepared, for example, from organic dicarboxylic acids having 2 to 12 carbon atoms and polyhydric alcohols, preferably diols, having 2 to 12 carbon atoms, preferably 2 to 6 carbon atoms.
  • suitable dicarboxylic acids include: succinic acid, glutaric acid, adipic acid, suberic acid, azelaic acid, sebacic acid, decanedicarboxylic acid, dodecanedicarboxylic acid, maleic acid, fumaric acid, phthalic acid, isophthalic acid, and terephthalic acid.
  • the dicarboxylic acids can be used individually or in mixtures with one another.
  • polyester polyols derived from lactones, e.g., caprolactone, or hydroxycarboxylic acids, e.g., hydroxycaproic acid and hydroxyacetic acid, can also be used.
  • polycondensation of aromatic or aliphatic carboxylic acids with polyhydric alcohols can also be carried out in the liquid phase in the presence of diluents and/or entrainers, such as benzene, toluene, xylene or chlorobenzene, for the azeotropic distillation of the condensation water.
  • diluents and/or entrainers such as benzene, toluene, xylene or chlorobenzene
  • the ratio of dicarboxylic acid (derivative) and polyhydric alcohol to be selected to obtain a desired OH number, functionality and viscosity and the alcohol functionality to be selected can be easily determined by the person skilled in the art.
  • Suitable polycarbonate polyols are those of a type known per se, which can be prepared, for example, by reacting diols such as 1,2-propanediol, 1,4-butanediol, 1,6-hexanediol, diethylene glycol, triethylene glycol, tetraethylene glycol, oligotetramethylene glycol and/or oligohexamethylene glycol with diaryl carbonates and/or dialkyl carbonates, e.g. diphenyl carbonate, dimethyl carbonate and bischloroformates or phosgene.
  • diols such as 1,2-propanediol, 1,4-butanediol, 1,6-hexanediol
  • diethylene glycol triethylene glycol, tetraethylene glycol, oligotetramethylene glycol and/or oligohexamethylene glycol
  • diaryl carbonates and/or dialkyl carbonates e.g. diphen
  • branched-chain and/or unsaturated alkanediols having usually not more than 12 carbon atoms such as 1,2-propanediol, 2-methyl-1,3-propanediol, 3-methyl-1,5-pentanediol, 2,2-dimethyl-1,3-propanediol, 2-butyl-2-ethyl-1,3-propanediol, 2-butene-1,4-diol and 2-butyne-1,4-diol, Diesters of terephthalic acid with glycols having 2 to 4 carbon atoms, such as terephthalic acid bis-ethylene glycol ester or terephthalic acid bis-1,4-butylene glycol ester and hydroxyalkylene ethers of hydroquinone or resorcinol, e.g.
  • alkanolamines having 2 to 12 carbon atoms such as ethanolamine, 2-aminopropanol and 3-amino-2,2-dimethylpropanol, N-alkyldialkanolamines, e.g.
  • butylbenzidine methylene-bis(4-amino-3-benzoic acid methyl ester), 2,4-chloro-4,4'-diamino-diphenylmethane, 2,4- and 2,6-toluylenediamine.
  • Amine catalysts familiar to the person skilled in the art can be used as catalyst (K-1), e.g. tertiary amines such as triethylamine, tributylamine, N-methylmorpholine, N-ethylmorpholine, N,N,N',N'-tetramethylethylenediamine, pentamethyldiethylenetriamine and higher homologues (DE-OS 26 24 527 and 26 24 528), l,4-diazabicyclo-(2,2,2)-octane, N-methyl-N'-dimethylaminoethylpiperazine, bis-(dimethylaminoalkyl)-piperazines (DE-A 26 36 787), N,N-dimethylbenzylamine, N,N-
  • catalysts (Kl) are known Mannich bases made from secondary amines, such as dimethylamine, and aldehydes, preferably formaldehyde, or ketones such as acetone, methyl ethyl ketone or cyclohexanone and phenols, such as phenol or alkyl-substituted phenols.
  • Tertiary amines with hydrogen atoms active towards isocyanate groups can also be used as catalysts (K1), e.g.
  • Silaamines with carbon-silicon bonds as described in US-A 3 620 984, e.g. 2,2,4-trimethyl-2-silamorpholine and 1,3-diethylaminomethyltetramethyldisiloxane, can also be used as catalysts (K1).
  • Tetraalkylammonium hydroxides and hexahydrotriazines are also suitable.
  • the reaction between isocyanate groups and Zerewitinoff-active hydrogen atoms is also greatly accelerated by lactams and azalactams, with an initial association between the lactam and the compound containing acidic hydrogen being formed.
  • amines are used as catalysts (K-1) to catalyze the polyurethane reaction
  • polyoxyalkylene polyols produced under amine catalysis may already contain catalytically active amines.
  • organic metal compounds can be used as catalysts (K-1) for this purpose, preferably organic tin compounds such as tin(II) salts of organic carboxylic acids, e.g., tin(II) acetate, tin(II) octoate, tin(II) ethylhexoate, and tin(II) taurate, and, less preferably, the dialkyltin(IV) salts of mineral acids or organic carboxylic acids, e.g., dibutyltin diacetate, dibutyltin dilaurate, dibutyltin maleate, dioctyltin diacetate, and dibutyltin dichloride.
  • Sulfur-containing compounds such as di-n-octyltin mercaptide (US Pat. No. 3,645,927) can also be used.
  • Catalysts (K-1) that specifically catalyze the trimerization of isocyanate groups are used to produce polyurethane materials with high proportions of so-called poly(isocyanurate) structures ("PIR foams"). Typically, formulations with significant excesses of NCO groups over OH groups are used to produce such materials. PIR foams are typically produced with K values of 180 to 600.
  • Catalysts (K-1) that contribute to the formation of isocyanurate structures are metal salts such as potassium or sodium acetate, sodium octoate, and amino compounds such as 1,3,5-tris(3-dimethylaminopropyl)hexahydrotriazine.
  • the catalysts (K-1) or catalyst combinations of different catalysts (K-1) are generally used in amounts between about 0.001 and 10 wt.%, in particular 0.01 to 4 wt.%, based on the total amount of components (J-1) and (J-2).
  • auxiliaries and additives may optionally be used.
  • examples include surface-active additives such as emulsifiers, foam stabilizers, cell regulators, flame retardants, nucleating agents, antioxidants, stabilizers, lubricants and mold release agents, dyes, dispersing aids, and pigments.
  • emulsifiers include, for example, the sodium salts of castor oil sulfonates or salts of fatty acids with amines such as diethylamine oleate or diethanolamine stearate.
  • Alkali metal or ammonium salts of sulfonic acids such as dodecylbenzenesulfonic acid or dinaphthylmethanedisulfonic acid, or of fatty acids such as ricinoleic acid, or of polymeric fatty acids may also be used as surface-active auxiliaries and additives (K-2).
  • Polyether siloxanes are particularly suitable as foam stabilizers. These compounds are They are generally constructed by combining copolymers of ethylene oxide and propylene oxide with a polydimethylsiloxane residue. Such foam stabilizers can be reactive toward isocyanates or, due to etherification of the terminal OH groups, unreactive toward isocyanates. They are described, for example, in US Pat. Nos.
  • organopolysiloxanes oxyethylated alkylphenols, oxyethylated fatty alcohols, and paraffin oils, as well as cell regulators such as paraffins, fatty alcohols, and dimethylpolysiloxanes, are also suitable.
  • Oligomeric polyacrylates with polyoxyalkylene and fluoroalkane residues as side groups are also suitable for improving the emulsifying effect, the dispersion of the filler, the cell structure, and/or for stabilizing the cell structure.
  • the surface-active substances are typically used in amounts of 0.01 to 5 parts by weight, based on 100 parts by weight of the total amount of components (J1) and (J-2).
  • Reaction retarders e.g., acidic substances such as hydrochloric acid, or organic acids and acid halides, as well as pigments or dyes and known flame retardants, e.g., tris(chloroethyl)phosphate, tricresyl phosphate, or ammonium phosphate and polyphosphate, as well as stabilizers against aging and weathering, plasticizers, and fungicidal and bactericidal substances, may also be added.
  • acidic substances such as hydrochloric acid, or organic acids and acid halides
  • pigments or dyes and known flame retardants e.g., tris(chloroethyl)phosphate, tricresyl phosphate, or ammonium phosphate and polyphosphate, as well as stabilizers against aging and weathering, plasticizers, and fungicidal and bactericidal substances, may also be added.
  • K-2 surface-active auxiliaries and additives
  • foam stabilizers as well as cell regulators, reaction retarders, stabilizers, flame-retardant substances, plasticizers, dyes and fillers, as well as fungistatic and bacteriostatic substances, as well as details on the use and mode of action of these additives, are described in R. Vieweg, A. Höchtlen (eds.): "Kunststoff-Handbuch,” Volume VII, Carl-Hanser-Verlag, Kunststoff 1966, pp. 103-113.
  • Water can be used as an optional blowing agent (E), which reacts in situ with the organic polyisocyanates or with the prepolymers containing isocyanate groups to form carbon dioxide and amino groups, which in turn react with other isocyanate groups to form urea groups and act as a chain extender. If water is added to the polyurethane formulation to adjust the desired density, it is typically used in amounts of 0.001 to 6.0 wt. %, based on the weight of components (J-1), (J-2), (K-1), and (K-2).
  • E optional blowing agent
  • blowing agents (E) instead of water or preferably in combination with water, gases or highly volatile inorganic or organic substances which evaporate under the influence of the exothermic polyaddition reaction and advantageously have a boiling point under atmospheric pressure in the range from -40 to 120 °C, preferably from 10 to 90 °C, can also be used as physical blowing agents.
  • Suitable organic blowing agents are, for example, acetone, ethyl acetate, methyl acetate, halogen-substituted alkanes such as methylene chloride, chloroform, ethylidene chloride, Vinylidene chloride, monofluorotrichloromethane, chlorodifluoromethane, dichlorodifluoromethane, HFCs such as R 134a, R 245fa, and R 365mfc, partially halogenated olefins (so-called HFOs or HCFOs) such as trans-1,3,3,3-tetrafluoropropene or trans-l-chloro-3,3,3-trifluoropropene, and unsubstituted alkanes such as butane, n-pentane, isopentane, cyclopentane, hexane, heptane, or diethyl ether.
  • propellants can also be used as mixtures.
  • suitable inorganic propellants include air, CO2, or N2O.
  • a propellant effect can also be achieved by adding compounds which decompose at temperatures above room temperature with the release of gases, for example nitrogen and/or carbon dioxide, such as azo compounds, e.g. azodicarbonamide or azoisobutyronitrile, or salts such as ammonium bicarbonate, ammonium carbamate or ammonium salts of organic carboxylic acids, e.g. the monoammonium salts of malonic acid, boric acid, formic acid or acetic acid. Details on the use of blowing agents and criteria for the selection of blowing agents are described in R. Vieweg, A.
  • the appropriate amount of solid blowing agents, low-boiling liquids or gases to be used depends on the desired PUR material density and the amount of water used.
  • the required amounts can easily be determined experimentally. Satisfactory results are usually achieved with solids amounts of 0.5 to 35 parts by weight, preferably 2 to 15 parts by weight, liquid amounts of 1 to 30 parts by weight, preferably 3 to 18 parts by weight and/or gas amounts of 0.01 to 80 parts by weight, preferably 10 to 35 parts by weight, in each case based on the weight of the structural components (J-1), (J-2) and (M).
  • the gas loading with e.g. B.
  • Air, carbon dioxide, nitrogen and/or helium can be introduced either via the formulation components (J-1), (J-2), (K-1) and (K-2) or via the polyisocyanate as component (M) or via the components (J-1), (J-2), (K-1) and (K-2) on the one hand and component (M) on the other hand.
  • Suitable are, for example, ethylene diisocyanate, 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate (HDI), 1,12-dodecane diisocyanate, cyclobutane-1,3-diisocyanate, cyclohexane-1,3- and -1,4-diisocyanate and any mixtures of these isomers, 1 isocyanato-3,3,5-trimethyl-5-isocyanatomethyl-cyclohexane (DE-B 1 202 785, US-A 3 401 190), 2,4- and 2,6-hexahydrotoluene diisocyanate and any mixtures of these isomers, hexahydro-1,3- and -1,4-phenylene diisocyanate, pcrhydro-2,4'- and -4,4'-diphenylmethane diisocyanate, 1,3- and 1,4-phenylene
  • suitable polyisocyanates are: triphenylmethane-4,4',4"-triisocyanate, polyphenyl-polymethylene polyisocyanates, as obtained by aniline-formaldehyde condensation and subsequent phosgenation and described, for example, in GB-A 874 430 and GB A 848 671, m- and p-isocyanatophenylsulfonyl isocyanates according to US-A 3 454 606, perchlorinated aryl polyisocyanates, as described in US-A 3 277 138, polyisocyanates containing carbodiimide groups, as described in US-A 3 152 162 and in DE-A 25 04 400, 25 37 685 and 25 52 350, norbornane diisocyanates according to US-A 3 492 301, allophanate-containing polyisocyanates Polyisocyanates as described in GB-A 994 890, BE-B 761 626 and
  • distillation residues containing isocyanate groups obtained during industrial isocyanate production optionally dissolved in one or more of the aforementioned polyisocyanates.
  • Preferred polyisocyanates are those that are readily available industrially, e.g., tolylene 2,4- and 2,6-diisocyanate and any mixtures of these isomers ("TDI”), polyphenylpolymethylene polyisocyanates, such as those produced by aniline-formaldehyde condensation followed by phosgenation (“crude MDI”), and polyisocyanates containing carbodiimide groups, urethane groups, allophanate groups, isocyanurate groups, urea groups, or biuret groups (“modified polyisocyanates”), particularly those modified polyisocyanates derived from tolylene 2,4- and/or 2,6-diisocyanate or from diphenylmethane 4,4'- and/or 2,4'-diisocyanate.
  • TDI tolylene 2,4- and 2,6-diisocyanate and any mixtures of these isomers
  • CAMDI phosgenation
  • modified polyisocyanates particularly
  • Naphthylene 1,5-diisocyanate and mixtures of the polyisocyanates mentioned are also well suited. It is also possible to use prepolymers containing isocyanate groups, which are obtainable by reacting a portion or the entire amount of the hydroxyl-containing compound (A) to be used according to the invention and/or a portion or the entire amount of the isocyanate-reactive components described above, which may be admixed with the hydroxyl-containing compound (A) to be used according to the invention, with at least one aromatic di- or polyisocyanate from the group TDI, MDI, DIBDI, NDI, DDI, preferably with 4,4'-MDI and/or 2,4-TDI and/or 1,5-NDI, to form a polyaddition product containing urethane groups, preferably urethane groups and isocyanate groups.
  • the prepolymers containing isocyanate groups are prepared by reacting exclusively higher molecular weight polyhydroxyl compounds, i.e. the hydroxyl group-containing compound (A) to be used according to the invention, and/or polyetherester polyols, polyether polyols, polyester polyols or polycarbonate polyols with the polyisocyanates, preferably 4,4'-MDI, 2,4-TDI and/or 1,5 NDI.
  • the prepolymers containing isocyanate groups can be produced in the presence of catalysts. However, it is also possible to produce the prepolymers containing isocyanate groups in the absence of catalysts and add them to the reaction mixture later to produce the PUR materials.
  • the polyisocyanate (M) is one or more compounds and is selected from the group consisting of 2,4- and 2,6-tolylene diisocyanate, 4,4'- and 2,4'- and 2,2'-diphenylmethane diisocyanate and polyphenylpolymethylene polyisocyanate, preferably 2,4- and 2,6-tolylene diisocyanate.
  • the ratio of isocyanate groups in the polyisocyanates (M) to the isocyanate-reactive hydrogens in components (J-1), (J-2), (L), (K-1), and (K-2) can be varied widely. Typical ratios are 0.9:1 to 6:1.
  • the invention also provides a polyurethane (I), preferably a polyurethane foam (I-1) or a compact polyurethane (I-2), obtainable by the process according to the invention.
  • a polyurethane preferably a polyurethane foam (I-1) or a compact polyurethane (I-2), obtainable by the process according to the invention.
  • the polyurethane (I), preferably the polyurethane foam (1-1) or the compact polyurethane (1-2) contains oximic urethane bonds, wherein the oximic urethane bonds are formed by reacting the hydroxyl group-containing compound (A) containing oximic hydroxyl groups with the isocyanate groups of the polyisocyanate as component (M).
  • the polyurethane (I), preferably the polyurethane foam (1-1) or the compact polyurethane (1-2), is sulfur-free and the calculated proportion of the oximic urethane bonds in the polyurethane (I), preferably in the polyurethane foam (1-1) or in the compact polyurethane (1-2), is from 20 mol% to 100 mol%, preferably from 25 mol% to 100 mol%, particularly preferably from 30 mol% to 100 mol%, and very particularly preferably from 35 mol% to 100 mol%, based on the sum of all urethane bonds of the polyurethane (I), preferably the polyurethane foam (1-1) or the compact polyurethane (1-2).
  • the invention also provides a process for producing a polyurethane (N) comprising a thermal treatment or an enzymatic treatment, preferably a thermal treatment, of the polyurethane (I) according to the invention, preferably the polyurethane foam (I-1) or the compact polyurethane (I-2) obtained by the process according to the invention.
  • the thermal treatment is carried out at a temperature T(N) of 100 °C to 220 °C, preferably of 130 °C to 200 °C.
  • the thermal treatment is carried out at a pressure p(N) of 50 bar to 300 bar, preferably of 80 bar to 200 bar.
  • the thermal treatment is carried out in a reaction time t(N) of 0.1 min to 20 min, preferably of 0.2 min to 15 min.
  • the thermal treatment is carried out in a co-rotating multi-screw extruder, such as a twin-screw or quadruple-screw extruder, a ring extruder, a co-kneader, or a planetary roller extruder, or in rotor-stator systems.
  • a co-rotating multi-screw extruder such as a twin-screw or quadruple-screw extruder, a ring extruder, a co-kneader, or a planetary roller extruder, or in rotor-stator systems.
  • Other suitable devices are single- or twin-screw large-volume kneaders.
  • the large-volume twin-screw kneaders can be co-rotating or counter-rotating.
  • Examples of large-volume kneaders include: CRP (von List Technology AG), Reacom (Buss-SMS-Canzler GmbH), Reasil (Buss-SMS-Canzler GmbH), KRC Kneter (Kurimoto, Ltd).
  • the polyurethane (N) is a thermoplastic polyurethane (N-1).
  • the invention also relates to a polyurethane (N), preferably a thermoplastic polyurethane (N-1), obtainable by the process according to the invention.
  • N polyurethane
  • N-1 thermoplastic polyurethane
  • the polyurethane (N), preferably the thermoplastic polyurethane (N-1), is sulfur-free.
  • the polyurethane (N), preferably the thermoplastic polyurethane (N-1), contains no oximic urethane bonds. In a preferred embodiment of the invention, the polyurethane (N), preferably the thermoplastic polyurethane (N-1), contains oximic hydroxyl groups.
  • the polyurethane (N), preferably the thermoplastic polyurethane (N-1), contains oximic urethane bonds, wherein the proportion of oximic urethane bonds, based on the sum of all urethane bonds of the polyurethane (N), preferably the thermoplastic polyurethane (N-1), is lower than for the polyurethane (I), preferably the polyurethane foam (I-1) or the compact polyurethane (I-2).
  • the proportion of oximic urethane bonds is preferably determined using an IR method, with the skilled person selecting a suitable IR method based on their specialist knowledge.
  • the proportion of oximic urethane bonds is lower than in the polyurethane (I), wherein the polyurethane (N), preferably the thermoplastic polyurethane (N-1), contains oximic hydroxyl groups.
  • the invention also relates to a process for producing a polyurethane (O) by reacting the polyurethane (N) according to the invention, preferably the thermoplastic polyurethane (N-1), comprising the steps:
  • the temperature T(O) is lower than the temperature T(N).
  • the thermal treatment is carried out at a temperature T(O) of 80 °C to 200 °C, preferably of 110 °C to 180 °C.
  • the thermal treatment is carried out at a pressure p(O) of 50 bar to 300 bar, preferably of 80 bar to 200 bar. In one embodiment of the invention, the thermal treatment is carried out in a reaction time t(O) of 0.1 min to 20 min, preferably of 0.2 min to 15 min.
  • the thermal treatment of the polyurethane (N), preferably the thermoplastic polyurethane (N-1), takes place in a co-rotating multi-screw extruder, such as a twin-screw or four-screw extruder or a ring extruder, a co-kneader or a planetary roller extruder, or in rotor-stator systems.
  • a co-rotating multi-screw extruder such as a twin-screw or four-screw extruder or a ring extruder, a co-kneader or a planetary roller extruder, or in rotor-stator systems.
  • Other suitable devices are single- or twin-screw high-volume kneaders.
  • the large-volume twin-screw kneaders can be co-rotating or counter-rotating.
  • high-volume kneaders examples include CRP (von List Technology AG), Reacom (Buss-SMS-Canzler GmbH), Reasil (Buss-SMS-Canzler GmbH), and KRC Kneter (Kurimoto, Ltd).
  • the invention also provides a polyurethane (O) obtainable by the process according to the invention.
  • the polyurethane (O) is sulfur-free.
  • the polyurethane (O) contains oximic urethane bonds, wherein the proportion of oximic urethane bonds relative to the sum of all urethane bonds of the polyurethane (O) is higher than for the polyurethane (N), preferably the thermoplastic polyurethane (N-1).
  • the proportion of oximic urethane bonds is preferably determined using an IR method, with the skilled person selecting a suitable IR method based on their specialist knowledge.
  • the invention relates to a hydroxyl group-containing compound (A), wherein at least some of the hydroxyl groups are oximic hydroxyl groups, wherein the hydroxyl group-containing compound (A) is composed of the elements carbon, hydrogen, oxygen and nitrogen, wherein the hydroxyl group-containing compound (A) has an OH number (determined by means of DIN 4629-2 (December 2016)) of 10 mg KOH/g to 600 mg KOH/g, preferably of 12 mg KOH/g to 500 mg KOH/g, and wherein the hydroxyl group-containing compound (A) contains oxypropylene units.
  • the invention relates to a hydroxyl group-containing compound (A) according to the first embodiment, wherein the hydroxyl group-containing compound (A) contains oxyethylene and oxypropylene units.
  • the invention relates to a hydroxyl group-containing compound (A) according to the first or second embodiment, wherein the hydroxyl group-containing compound (A) contains at least 3 directly consecutive oxypropylene units.
  • the invention relates to a hydroxyl group-containing compound (A) according to any one of the first to third embodiments, wherein the calculated proportion of the oximic hydroxyl groups is from 20 mol% to 100 mol%, preferably from 25 mol% to 100 mol%, particularly preferably from 30 mol% to 100 mol%, and very particularly preferably from 35 mol% to 100 mol%, based on the sum of all free hydroxyl groups of the hydroxyl group-containing compound.
  • the invention relates to a hydroxyl group-containing compound (A) according to any one of the first to fourth embodiments, wherein the hydroxyl group-containing compound has a calculated hydroxyl group functionality of from 1 to 8, preferably from 2 to 6 and particularly preferably from 2 to 4.
  • the invention relates to a process for preparing a hydroxyl group-containing compound (A), preferably the hydroxyl group-containing compound (A) according to any one of the first to fifth embodiments, comprising the steps: i) reacting a component (B) containing one or more aliphatic hydroxyl group(s) with a component (C) containing (C-1) one or more hydroxyl group-reactive functional group(s) and (C-2) one or more carbonyl group(s), optionally in the presence of a catalyst (D) to form an intermediate (E), and ii) reacting the intermediate (E) with hydroxylamine and/or salts of hydroxylamine, preferably hydroxylamine.
  • the invention relates to a process according to the sixth embodiment, wherein the hydroxyl group-containing compound (A) is composed of the elements carbon, hydrogen, oxygen and nitrogen.
  • the invention relates to a process according to the sixth or seventh embodiment, wherein the aliphatic hydroxyl groups of component (B) are primary and/or secondary hydroxyl groups.
  • the invention relates to a process according to one of the sixth to eighth embodiments, wherein component (B) is obtainable or preferably obtained by reacting an H-functional starter compound (F) with an alkylene oxide (G) in the presence of a catalyst (H).
  • the invention relates to a process of the ninth embodiment, wherein the H-functional starter compound (F) is an amine and/or an alcohol, preferably an alcohol.
  • the invention relates to a process of the tenth embodiment, wherein the H-functional starter compound (F) does not contain any thiol groups.
  • the invention relates to a process of any of the ninth to eleventh embodiments, wherein the H-functional starter compound (F) is composed of the elements carbon, hydrogen, oxygen and nitrogen.
  • the invention relates to a process according to any one of the ninth to twelfth embodiments, wherein the H-functional starter compound (F) is an alcohol, and the alcohol is one or more compounds and is selected from the group consisting of ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 2- Methylpropane-1,3-diol, neopentyl glycol, 1,6-hexanediol, diethylene glycol, dipropylene glycol, glycerin, trimethylolpropane, a difunctional polyether polyol and a trifunctional polyether polyol.
  • the H-functional starter compound (F) is an alcohol
  • the alcohol is one or more compounds and is selected from the group consisting of ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-but
  • the invention relates to a process according to any one of the ninth to thirteenth embodiments, wherein the alkylene oxide (G) is propylene oxide and/or ethylene oxide.
  • the invention relates to a process according to any one of the ninth to fourteenth embodiments, wherein a mixture of ethylene oxide and propylene oxide is used as alkylene oxide (G), and this mixture preferably comprises up to 75% by mass of ethylene oxide, more preferably up to 50% by mass of ethylene oxide and most preferably up to 30% by mass of ethylene oxide, based on the total mass of the mixture of ethylene oxide and propylene oxide.
  • G alkylene oxide
  • the invention relates to a process according to any one of the ninth to fifteenth embodiments, wherein the catalyst (H) is a double metal cyanide (DMC) catalyst, an alkali metal hydroxide, an alkaline earth metal hydroxide and/or an amine, a Lewis acid or a Brensted acid, preferably a double metal cyanide (DMC) catalyst or an alkali metal hydroxide.
  • the catalyst (H) is a double metal cyanide (DMC) catalyst, an alkali metal hydroxide, an alkaline earth metal hydroxide and/or an amine, a Lewis acid or a Brensted acid, preferably a double metal cyanide (DMC) catalyst or an alkali metal hydroxide.
  • DMC double metal cyanide
  • the invention relates to a process according to any one of the ninth to sixteenth embodiments, wherein the hydroxyl group-reactive functional group of component (C) is a carboxylic acid group, a carboxylic acid chloride group or a carboxylic acid ester group, preferably a carboxylic acid group.
  • the invention relates to a process according to the seventeenth embodiment, wherein the hydroxyl group-reactive functional group of component (C) is a carboxylic acid group, and component (C) is one or more compounds and is selected from the group consisting of levulinic acid, acetoacetic acid, pyruvic acid, a-methyllevulinic acid, 3-methyl-4-oxopentanoic acid, 4-oxo-2-propyl-pentanoic acid, 2-acetyl-4-methylpentanoic acid, preferably levulinic acid, acetoacetic acid and pyruvic acid.
  • component (C) is one or more compounds and is selected from the group consisting of levulinic acid, acetoacetic acid, pyruvic acid, a-methyllevulinic acid, 3-methyl-4-oxopentanoic acid, 4-oxo-2-propyl-pentanoic acid, 2-acetyl-4-methylpentanoic acid, preferably levulin
  • the invention relates to a process according to any of the sixth to eighteenth embodiments, wherein the catalyst (D) is one or more compounds selected from the group consisting of tin dichloride, tin dichloride dihydrate, tin(II) 2-ethylhexanoate, dibutyltin dilaurate, titanium tetrabutoxide, tetraisopropyl titanate; bismuth(III) neodecanoate; zinc(II) acetate; manganese(II) acetate; p-toluenesulfonic acid, preferably p-toluenesulfonic acid.
  • the invention relates to a hydroxyl-containing compound (A) obtainable by the process according to any of the sixth to nineteenth embodiments.
  • the invention relates to a process for producing a polyurethane (I), preferably a polyurethane foam (I-1) or a compact polyurethane (I-2) by reacting the components
  • the invention relates to a process according to the twenty-first embodiment, wherein the polyoxyalkylene polyol (J-2) is polyester polyol, a polycarbonate polyol, a polyether carbonate polyol, a polyester carbonate polyol, a polyether ester carbonate polyol and/or a low molecular weight chain extender and/or crosslinking agent having OH numbers or NH numbers of 6 to 1870 mg KOH/g.
  • the polyoxyalkylene polyol (J-2) is polyester polyol, a polycarbonate polyol, a polyether carbonate polyol, a polyester carbonate polyol, a polyether ester carbonate polyol and/or a low molecular weight chain extender and/or crosslinking agent having OH numbers or NH numbers of 6 to 1870 mg KOH/g.
  • the invention relates to a process according to any one of the twenty-first to twenty-third embodiments, wherein the polyisocyanate (M) is one or more compounds and is selected from the group consisting of 2,4- and 2,6-tolylene diisocyanate, 4,4'- and 2,4'- and 2,2'-diphenylmethane diisocyanate and polyphenylpolymethylene polyisocyanate, preferably 2,4- and 2,6-tolylene diisocyanate.
  • the polyisocyanate (M) is one or more compounds and is selected from the group consisting of 2,4- and 2,6-tolylene diisocyanate, 4,4'- and 2,4'- and 2,2'-diphenylmethane diisocyanate and polyphenylpolymethylene polyisocyanate, preferably 2,4- and 2,6-tolylene diisocyanate.
  • the invention relates to a polyurethane (I), preferably polyurethane foam (1-1) or compact polyurethane (1-2), obtainable by the process according to any one of the twenty-first to twenty-fourth embodiments.
  • the invention relates to a polyurethane (I) according to the twenty-fifth embodiment, wherein the polyurethane (I), preferably the polyurethane foam (1-1) or the compact polyurethane (1-2), is sulfur-free and the calculated proportion of the oximic urethane bonds in the polyurethane (I), preferably in the polyurethane foam (1-1) or in the compact polyurethane (1-2), is from 20 mol% to 100 mol%, preferably from 25 mol% to 100 mol%, particularly preferably from 30 mol% to 100 mol%, and very particularly preferably from 35 mol% to 100 mol%, based on the sum of all urethane bonds of the polyurethane (I), preferably of the polyurethane foam (1-1) or of the compact polyurethane (1-2).
  • the invention relates to a use of the hydroxyl group-containing compound (A) according to any one of the first to fifth embodiments or the hydroxyl group-containing compound (A) obtainable by the process according to any one of the sixth to nineteenth embodiments for facilitating the cleavage of urethane bonds in a process for recycling a polyurethane.
  • the invention relates to a process for producing a polyurethane (N) comprising a thermal treatment or an enzymatic treatment, preferably a thermal treatment, of the polyurethane (I), preferably the polyurethane foam (1-1) or the compact polyurethane (1-2) according to the twenty-sixth or twenty-seventh embodiment or obtained by the process according to one of the twenty-first to twenty-fifth embodiments.
  • the invention relates to a method according to the twenty-eighth embodiment, wherein the thermal treatment is carried out at a temperature T(N) of 100°C to 220°C, preferably of 130°C to 200°C.
  • the invention relates to a process according to the twenty-eighth or twenty-ninth embodiment, wherein the thermal treatment is carried out at a pressure p(N) of 50 bar to 300 bar, preferably of 80 bar to 200 bar.
  • the invention relates to a process according to one of the twenty-eighth to thirtieth embodiments, wherein the thermal treatment takes place in a reaction time t(N) of 0.1 min to 20 min, preferably of 0.2 min to 15 min.
  • the invention relates to a process according to any one of the twenty-eighth to thirty-first embodiments, wherein the thermal treatment is carried out in a co-rotating multi-screw extruder, such as a twin-screw or a four-screw extruder or a ring extruder, a co-kneader or a planetary roller extruder or in rotor-stator systems.
  • a co-rotating multi-screw extruder such as a twin-screw or a four-screw extruder or a ring extruder, a co-kneader or a planetary roller extruder or in rotor-stator systems.
  • the invention relates to a process according to any one of the twenty-eighth to thirty-second embodiments, wherein the polyurethane (N) is a thermoplastic polyurethane (N-1).
  • the invention relates to a polyurethane (N), preferably a thermoplastic polyurethane (N-1) obtainable by the process according to one of the twenty-eighth to thirty-third embodiments.
  • the invention relates to a polyurethane (N), preferably a thermoplastic polyurethane (Nl) according to the thirty-fourth or thirty-fifth embodiment, wherein the polyurethane (N), preferably the thermoplastic polyurethane (Nl), does not contain any oximic urethane bonds.
  • the invention relates to a polyurethane (N), preferably a thermoplastic polyurethane (Nl) according to the thirty-fourth or thirty-fifth embodiment, wherein the polyurethane (N), preferably the thermoplastic polyurethane (Nl) contains oximic urethane bonds, wherein the proportion of the oximic urethane bonds, based on the sum of all urethane bonds of the polyurethane (N), preferably of the thermoplastic polyurethane (Nl), is lower than for the polyurethane (I), preferably the polyurethane foam (I-1) or the compact polyurethane (I-2).
  • the invention relates to a polyurethane (N), preferably the thermoplastic polyurethane (N-1) according to the thirty-seventh embodiment, wherein the polyurethane (N), preferably the thermoplastic polyurethane (N-1) contains oximic hydroxyl groups.
  • the invention relates to a process for producing a polyurethane (O) by reacting the polyurethane (N), preferably the thermoplastic polyurethane (N-1) according to one of the thirty-fourth to thirty-eighth embodiments, comprising the steps:
  • the invention relates to a method according to the thirty-ninth embodiment, wherein the temperature T(O) is lower than the temperature T(N).
  • the invention relates to a process according to the thirty-ninth or fortieth embodiment, wherein the thermal treatment is carried out at a temperature T(O) of 80 °C to 200 °C, preferably of 110 °C to 180 °C.
  • the invention relates to a process according to one of the thirty-ninth to forty-first embodiments, wherein the thermal treatment is carried out at a pressure p(O) of 50 bar to 300 bar, preferably of 80 bar to 200 bar.
  • the invention relates to a process according to the thirty-ninth or forty-first embodiment, wherein the thermal treatment is carried out in a reaction time t(O) of 0.1 min to 20 min, preferably of 0.2 min to 15 min.
  • the invention relates to a process according to the thirty-ninth or forty-second embodiment, wherein the thermal treatment is carried out in a co-rotating multi-screw extruder, such as a twin-screw or a four-screw extruder or a ring extruder, a co-kneader or a planetary roller extruder or in rotor-stator systems.
  • a co-rotating multi-screw extruder such as a twin-screw or a four-screw extruder or a ring extruder, a co-kneader or a planetary roller extruder or in rotor-stator systems.
  • the invention relates to a polyurethane (O) obtainable by the process according to any one of the thirty-ninth to forty-third embodiments.
  • the invention relates to a polyurethane (O) according to one of the forty-fourth embodiments, wherein the proportion of oximic urethane bonds based on the sum of all urethane bonds of the polyurethane (O) is higher than for the polyurethane (N), preferably the thermoplastic polyurethane (N-1).
  • OH number The OH numbers (hydroxyl numbers) were determined according to the regulations of DIN 4629-2 (December 2016).
  • Viscosity The viscosities were determined using a rotational viscometer (Physica MCR 72, manufacturer: Anton Paar) according to DIN 53019-1 (September 2008).
  • Acid number The acid number was determined according to DIN EN ISO 2114 (January 2006).
  • NMR The (1H and 13C ) NMR spectra were recorded according to DIN EN ISO/IEC 17025 on a Broker AV III HD 600 NMR spectrometer. CDCh was used as solvent.
  • DMA Dynamic Mechanical Analysis
  • the softening temperature of the polyurethanes (I) was determined from the intersection point of the tangent to the extended base line and the tangent at the steepest point of the decrease of the tensile storage modulus.
  • Arcol® Polyol 1104 Trifunctional polyether polyol based on glycerol with an OH number of 55.5 mg KOH/g obtained by polymerization with 100 wt.% propylene oxide.
  • Arcol® Polyol 1108 Trifunctional polyether polyol based on glycerol with an OH number of 48 mg KOH/g obtained by copolymerization of 12 wt.% ethylene oxide with 88 wt.% propylene oxide.
  • Arcol® Polyol 1004 Bifunctional polyether polyol based on propylene glycol with an OH number of 260 mg KOH/g obtained by polymerization with 100 wt.% propylene oxide.
  • Arcol® Polyol 1030 Trifunctional polyether polyol based on glycerol with an OH number of 400 mg KOH/g obtained by polymerization with 100 wt.% propylene oxide.
  • Component (C) Levulinic acid: 98%, Sigma-Aldrich.
  • Step (i) Preparation of intermediate (E) by esterification of component (B) with component (C):
  • Step (i) Preparation of intermediate (E) by esterification of component (B) with component (C):

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Abstract

La présente invention concerne un composé contenant des groupes hydroxyle oxymiques et son procédé de préparation. L'invention concerne en outre un procédé de préparation d'un polyuréthane, comprenant la réaction du composé contenant des groupes hydroxyle oxymiques, les polyuréthanes résultant et un traitement thermique de ce polyuréthane.
PCT/EP2024/085950 2023-12-21 2024-12-12 Composé contenant des groupes hydroxyle oxymiques et son procédé de préparation Pending WO2025131996A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP23219543.8 2023-12-21
EP23219543.8A EP4574869A1 (fr) 2023-12-21 2023-12-21 Composé contenant des groupes hydroxyles oxime et son procédé de préparation
EP24184323.4 2024-06-25
EP24184323 2024-06-25

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WO2025131996A1 true WO2025131996A1 (fr) 2025-06-26

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DE2537685A1 (de) 1975-08-23 1977-03-03 Bayer Ag Verfahren zur teilweisen carbodiimidisierung der isocyanatgruppen von organischen isocyanaten
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EP0761708A2 (fr) 1995-08-22 1997-03-12 ARCO Chemical Technology, L.P. Compositions contenant des catalyseurs de cyanure de métal double et un polyétherpolyole
WO1997040086A1 (fr) 1996-04-19 1997-10-30 Arco Chemical Technology, L.P. Catalyseurs a haute activite a base de cyanure metallique double
DE19628145A1 (de) 1996-07-12 1998-01-15 Basf Ag Verfahren zur Herstellung von zelligen Polyurethan-Elastomeren
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WO1998016310A1 (fr) 1996-10-16 1998-04-23 Arco Chemical Technology, L.P. Catalyseurs a deux cyanures metalliques, contenant des polymeres fonctionnalises
WO2000047649A1 (fr) 1999-02-11 2000-08-17 Bayer Aktiengesellschaft Catalyseurs a base de cyanures metalliques doubles destines a la preparation de polyether-polyols
WO2001039883A1 (fr) 1999-12-03 2001-06-07 Bayer Aktiengesellschaft Procede de production de catalyseurs de cyanure bimetallique (dmc)
WO2001080994A1 (fr) 2000-04-20 2001-11-01 Bayer Aktiengesellschaft Procede de production de catalyseurs a base de cyanure metallique double
WO2023275029A1 (fr) * 2021-07-02 2023-01-05 Evonik Operations Gmbh Production de mousses de pu à l'aide de polyols recyclés

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US3277138A (en) 1966-10-04 Method for the chlorination of aromatic isocyanates
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GB848671A (en) 1956-11-16 1960-09-21 Ici Ltd Improvements in or relating to the manufacture of polymeric materials
DE1072385B (de) 1958-06-20 1959-12-31 Farbenfabriken Bayer Aktiengesellschaft Leverkusen Bayerwerk Verfahren zur Herstellung von harzartigen, gegebenenfalls noch löslichen, beim Erwärmen Isocyanatgruppen freisetzenden Polyadditionsprodukten
GB874430A (en) 1958-08-15 1961-08-10 Ici Ltd Improvements in or relating to the manufacture of polymeric materials
US3152162A (en) 1959-07-29 1964-10-06 Bayer Ag Polyisocyanate-carbodiimide adducts and process for the production thereof
GB994890A (en) 1961-12-18 1965-06-10 Ici Ltd New organic polyisocyanates and their manufacture
US3455883A (en) 1963-01-09 1969-07-15 Gen Mills Inc Polyisocyanates and derivatives
US3404109A (en) 1963-02-14 1968-10-01 Gen Tire & Rubber Co Production of polyether diols using water as a telogen
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DE1202785B (de) 1964-07-21 1965-10-14 Scholven Chemie Ag Verfahren zur Herstellung von 1-Isocyanato-3-(isocyanatomethyl)-3, 5, 5-trimethylcyclohexan
DE1222067B (de) 1964-11-07 1966-08-04 Bayer Ag Verfahren zur Herstellung von einheitlichen organischen Polyisocyanaten
DE1231688B (de) 1965-04-17 1967-01-05 Bayer Ag Verfahren zur Herstellung von Isocyanatocarbonsaeureestern polyfunktioneller Hydroxyverbindungen
DE1230778B (de) 1965-05-24 1966-12-22 Bayer Ag Verfahren zur Herstellung von acylierten Harnstoffpolyisocyanaten
US3394164A (en) 1965-10-24 1968-07-23 Upjohn Co Stabilized methylenebis-(phenyl isocyanate) compositions
US3492301A (en) 1965-11-01 1970-01-27 Armstrong Cork Co 2,4,6-trisubstituted sulfonylhydrazido-s-triazines
US3567763A (en) 1966-01-06 1971-03-02 Rohm & Haas Ester polyisocyanates
US3629308A (en) 1966-07-25 1971-12-21 Union Carbide Corp Siloxane-oxyalkylene block copolymers
US3644457A (en) 1967-03-08 1972-02-22 Bayer Ag Preparation of stable liquid diphenylmethane diisocyanates
DE1720633A1 (de) 1967-03-15 1971-07-01 Bayer Ag Verfahren zur Herstellung von Polyurethanen
US3620984A (en) 1967-06-27 1971-11-16 Bayer Ag Polyurethane catalysts
US3654106A (en) 1967-11-09 1972-04-04 Bayer Ag Isocyanate-containing telomers and a process for the production thereof
DE2004048A1 (de) 1968-03-13 1970-12-10 Bayer Ag Polyurethanschaeume
US3645927A (en) 1968-05-15 1972-02-29 Bayer Ag Polyurethane catalyst
DE1804361A1 (de) 1968-10-22 1970-05-14 Bayer Ag Aminoaether als Aktivatoren zur Herstellung von Polyurethanen
DE1929034A1 (de) 1969-06-07 1970-12-10 Bayer Ag Verfahren zur Herstellung von flammfeste Urethangruppen aufweisenden Schaumstoffen
BE752261A (fr) 1969-06-20 1970-12-01 Bayer Ag Procede pour la preparation de matieres plastiques presentant des groupes urethane eventuellement cellulaires, resistantes a l'inflammation
BE761626A (fr) 1970-01-17 1971-06-16 Bayer Ag Procede de preparation polyurethanes matieres cellulaires anti-inflammables a base d'isocyanates
US3829505A (en) 1970-02-24 1974-08-13 Gen Tire & Rubber Co Polyethers and method for making the same
US3941849A (en) 1972-07-07 1976-03-02 The General Tire & Rubber Company Polyethers and method for making the same
DE2504400A1 (de) 1975-02-01 1976-08-05 Bayer Ag Lagerstabile, carbodiimidgruppen enthaltende polyisocyanate
DE2523633A1 (de) 1975-05-28 1976-12-16 Bayer Ag Nicht einbaubare, geruchlose katalysatoren fuer die polyurethansynthese
DE2537685A1 (de) 1975-08-23 1977-03-03 Bayer Ag Verfahren zur teilweisen carbodiimidisierung der isocyanatgruppen von organischen isocyanaten
DE2552350A1 (de) 1975-11-21 1977-05-26 Bayer Ag Lagerstabile, carbodiimidgruppen enthaltende polyisocyanate
DE2558523A1 (de) 1975-12-24 1977-07-07 Bayer Ag Verfahren zur herstellung neuer polysiloxan-polyoxyalkylen-copolymerer
DE2618280A1 (de) 1976-04-27 1977-11-17 Bayer Ag Neue katalysatoren fuer die herstellung von polyurethanschaumstoffen
DE2624528A1 (de) 1976-06-01 1977-12-22 Bayer Ag Verfahren zur herstellung von polyurethanschaumstoffen
DE2624527A1 (de) 1976-06-01 1977-12-22 Bayer Ag Verfahren zur herstellung von polyurethanen
DE2636787A1 (de) 1976-08-16 1978-02-23 Bayer Ag Verfahren zur herstellung von polyurethanen
DE2732292A1 (de) 1977-07-16 1979-02-01 Bayer Ag Verfahren zur herstellung von polyurethankunststoffen
US5158922A (en) 1992-02-04 1992-10-27 Arco Chemical Technology, L.P. Process for preparing metal cyanide complex catalyst
US5470813A (en) 1993-11-23 1995-11-28 Arco Chemical Technology, L.P. Double metal cyanide complex catalysts
DE19509819A1 (de) 1994-03-17 1995-09-21 Polyurethane Kasei Kk Mikrozellulares Polyurethanelastomer und Verfahren zu dessen Herstellung
EP0700949A2 (fr) 1994-09-08 1996-03-13 ARCO Chemical Technology, L.P. Catalyseurs hautement actifs de cyanure de métal de double
EP0743093A1 (fr) 1995-05-15 1996-11-20 ARCO Chemical Technology, L.P. Catalyseurs à base de complexe de cyanure métallique double hautement actif
EP0761708A2 (fr) 1995-08-22 1997-03-12 ARCO Chemical Technology, L.P. Compositions contenant des catalyseurs de cyanure de métal double et un polyétherpolyole
WO1997040086A1 (fr) 1996-04-19 1997-10-30 Arco Chemical Technology, L.P. Catalyseurs a haute activite a base de cyanure metallique double
DE19627907A1 (de) 1996-07-11 1998-01-15 Basf Ag Verfahren zur Herstellung von kompakten oder zelligen Polyurethan-Elastomeren und hierfür geeignete Isocyanatprepolymere
DE19628145A1 (de) 1996-07-12 1998-01-15 Basf Ag Verfahren zur Herstellung von zelligen Polyurethan-Elastomeren
WO1998016310A1 (fr) 1996-10-16 1998-04-23 Arco Chemical Technology, L.P. Catalyseurs a deux cyanures metalliques, contenant des polymeres fonctionnalises
WO2000047649A1 (fr) 1999-02-11 2000-08-17 Bayer Aktiengesellschaft Catalyseurs a base de cyanures metalliques doubles destines a la preparation de polyether-polyols
WO2001039883A1 (fr) 1999-12-03 2001-06-07 Bayer Aktiengesellschaft Procede de production de catalyseurs de cyanure bimetallique (dmc)
WO2001080994A1 (fr) 2000-04-20 2001-11-01 Bayer Aktiengesellschaft Procede de production de catalyseurs a base de cyanure metallique double
WO2023275029A1 (fr) * 2021-07-02 2023-01-05 Evonik Operations Gmbh Production de mousses de pu à l'aide de polyols recyclés

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"Polyurethane Handbook", 1993, CARL-HANSER-VERLAG, pages: 113 - 115
"The Polyurethanes Book", 2002, JOHN WILEY & SONS, LTD.
M. IONESCU ET AL., ADVANCES IN URETHANES SCIENCE AND TECHNOLOGY, vol. 14, 1998, pages 151 - 218
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