Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
  • C08G18/48—Polyethers
  • C08G18/50—Polyethers having heteroatoms other than oxygen
  • C08G18/5072—Polyethers having heteroatoms other than oxygen containing sulfur
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
  • C07C309/01—Sulfonic acids
  • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
  • C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
  • C07C309/52—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton the carbon skeleton being further substituted by doubly-bound oxygen atoms
  • C07C309/53—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton the carbon skeleton being further substituted by doubly-bound oxygen atoms the carbon skeleton containing carbon atoms of quinone rings
  • C07C309/54—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton the carbon skeleton being further substituted by doubly-bound oxygen atoms the carbon skeleton containing carbon atoms of quinone rings at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
  • C07C309/56—Y being a hetero atom
• • 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
  • C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
  • C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
  • C08G18/0828—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing sulfonate groups or groups forming them
• • 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
  • C08G18/46—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
  • C08G18/4676—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing sulfur
• • 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
  • C08G18/71—Monoisocyanates or monoisothiocyanates
  • C08G18/715—Monoisocyanates or monoisothiocyanates containing sulfur in addition to isothiocyanate sulfur
• • 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
  • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
  • C08G18/775—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur sulfur

Definitions

• the present invention provides a solution to these problems. Surprisingly, it was found that by reacting polyhydroxy compounds with molar amounts of aromatic isocyanato sulfonic acids, optionally in a mixture with conventional polyisocyanates, novel hydroxy compounds are obtained which have increased polarity and surface-active properties and e.g. Foams made from it give improved fire behavior and high-frequency weldability.
• the present rfindunq E are thus at least one hydroxy group and at least one urethano-arylsulfonklarerios compounds having the average molecular weight of 300 to 12,000.
• Chain links are e.g. B. CH (CH 3 ) or CH 2 groups, ether oxygen atoms, CO groups, sulfur atoms and / or nitrogen atoms.
• the present invention also relates to a process for the preparation of compounds having an average molecular weight of 300 to 12,000 and containing at least one hydroxyl group and at least one urethano-arylsulfonic acid group, characterized in that at least two compounds having a molecular weight of 62 to 10,000 at 0-190 ° having hydroxyl groups C are reacted with aromatic isocyanatosulfonic acids, the equivalent ratio of the total amount of isocyanate groups (including any isocyanate groups present in dimerized form) to sulfonic acid groups 0.5 to 50 and the equivalent ratio of the sum of the hydroxyl groups of the at least two hydroxyl groups having compounds to NCO groups is 1.5 to 30.
• the present invention finally also relates to the use of the compounds according to the invention as a reaction component for polyisocyanates for the production of polyaddition products or polycondensation products.
• OH groups of the polyhydroxy compounds used as starting material are added to the NCO groups and any uretdione groups Ger isocyanatoarylsulfonic acid present, with the formation of higher molecular weight new polyhydroxy compounds which contain at least some urethane groups and one or more contain free sulfonic acid groups.
• the sulfonic acid groups can then be completely or partially neutralized with conventional inorganic or organic bases.
• the hydroxyl group-inhibiting polyesters are e.g. Reaction products of polyhydric, preferably dihydric and optionally additionally trihydric alcohols with polyhydric, preferably dihydric, carboxylic acids.
• polyhydric preferably dihydric and optionally additionally trihydric alcohols
• polyhydric preferably dihydric, carboxylic acids.
• the corresponding polycarboxylic anhydrides or corresponding polycarboxylic esters of lower alcohols or mixtures thereof can also be used to produce the polyesters.
• the polycarboxylic acids can be aliphatic, cycloaliphatic, aromatic and / or heterocyclic in nature and optionally, e.g. by halogen atoms, substituted and / or unsaturated.
• Examples of these include: succinic acid, adipic acid, suberic acid, azelaic acid, sebacic acid, phthalic acid, isophthalic acid, trimellitic acid, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, tetrachlorophthalic acid, malefic acid, malefic acid, malefic acid, malefic acid, malefic acid, malefic acid, malefic acid, malefic acid, malefic acid, malefic acid, malefic acid, malefic acid, malefic acid, malefic acid, malefic acid, malefic acid, malefic acid, malefic acid, fumaric acid, malefic acid, fumaric acid, fatty acid, malefic acid, fumaric acid, fumaric acid, fumaric acid, fatty acid, malefic acid, fumaric acid, such as, with monomeric fatty acids, dimethyl terephthalate, bis-glycol ester of lerephthalic acid.
• polyhydric alcohols are e.g. Ethylene glycol, propylene glycol (1,2) and - (1,3), butylene glycol- (1,4) and - (2,3), hexanediol- (1,6), octanediol- (1,8), neopentylglycol- Cyclohexanedimethanol (1,4-bis-hydroxymethylcyclohexane), 2-methyl-1,3-propanediol, glycerol, trimethylolpropane, hexanetriol- (1,2,6), butanetriol- (1,2,4), trimethylolethane, pentaerythritol, quinite , Mannitol and sorbitol, methylglycoside, also diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycols, dipropylene glycol, polypropylene glycols, dibutylene glycol and polybutylene glyco
• the polyethers which are preferred according to the invention and preferably have two hydroxyl groups are those of the type known per se and are obtained, for example, by polymerizing epoxides such as ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, styrene oxide, epichlorohydrin or 1,1,1-trichloroacetene-3, 4-oxide with itself, for example in the presence of BF 3 , or by addition of these epoxides, optionally in a mixture or in succession, to starting components with reactive hydrogens such as alcohols or amines, for example water, ethylene glycol, propylene glycol (1,3) or - (1,2), 4,4'-Dihydroxy-diphenylpropane, aniline.
• epoxides such as ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, styrene oxide, epichlorohydrin or 1,1,1-trichloroaceten
• Polyethers modified by vinyl polymers such as those e.g. by polymerizing styrene or acrylonitrile in the presence of foleyethers (US Pat. Nos. 3,383,351, 3,304,273, 3,523,093, 3,106,695, German Pat. No. 1,152,536) are also suitable.
• the higher-functionality polyesters which may also be used proportionally, are formed in an analogous manner by alkoxylation of higher-functionality starter molecules known per se, e.g. Ammonia, ethanolamine, ethylenediamine or sucrose.
• polythioethers the condensation products of thiodiglycol with themselves and / or with other glycols, dicarboxylic acids, formaldehyde, aminocarboxylic acids or amino alcohols are mentioned in particular.
• the products are polythio ether, palythio ether theater, polythio ether amide.
• polyacetals examples include the compounds which can be prepared from glycols, such as diethylene glycol, triethylene glycol, 4,4'-dioxethoxy-diphenyldimethyl-, methane, hexanediol and formaldehyde.
• glycols such as diethylene glycol, triethylene glycol, 4,4'-dioxethoxy-diphenyldimethyl-, methane, hexanediol and formaldehyde.
• Polyacetals suitable according to the invention can also be prepared by polymerizing cyclic acetals.
• Suitable polycarbonates containing hydroxyl groups are those of the type known to calibrated, for example by reacting diols such as propanediol (1,3), butenediol (1,4) and / or hexanediol (1,6), diethylene glycol, triethylene glycol Tetraethylene glycol with diaryl carbonates, for example diphenyl carbonate or phosgene, can be prepared.
• diols such as propanediol (1,3), butenediol (1,4) and / or hexanediol (1,6)
• diethylene glycol triethylene glycol Tetraethylene glycol
• diaryl carbonates for example diphenyl carbonate or phosgene
• polyester amides and polyamides include e.g. the predominantly linear condensates obtained from polyvalent saturated and unsaturated carboxylic acids or their anhydrides and polyvalent saturated and unsaturated amino alcohols, diamines, polyamines and their mixtures. Polyhydroxyl compounds already containing urethane or urea groups can also be used.
• polyhydroxy compounds can also be used in which high molecular weight polyadducts or polycondensates are contained in finely dispersed or dissolved form.
• modified polyhydroxyl compounds are obtained if polyaddition reactions (e.g. reactions between polyisocyanates and amino-functional compounds) or polycondensation reactions (e.g. between formaldehyde and phenols and / or amines) are carried out directly in situ in the above-mentioned compounds containing hydroxyl groups.
• Low molecular weight glycols which are mixed with the higher molecular weight polyhydroxy compounds mentioned or also alone Isocyanato sulfonic acids can be reacted are, for example: ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, oligopropylene glycols, (1,3) propylene glycol, butanediol, hexanediol, 2-xthylhexanediol, octanediol, glycerin, trimethylolpropane, dodecanediol.
• Amino alcohols such as ethanolamine, propanolamine, diethanolamine can also be used, provided that all the amino groups present are reacted with isocyanate groups.
• Mono-, di- or polyamines and water can also be used in minor amounts.
• the products obtained after the reaction should contain, apart from OH groups, at most in minor amounts of carboxyl groups or mercapto groups.
• Phosgenation products of condensates of aniline and aldehydes or ketones such as e.g. Acetaldehyde, propionaldehyde, butyraldehyde, acetone, methyl ethyl ketone.
• phosgenation products of condensates of anilines substituted on the nucleus alkyl in particular toluidines with aldehydes or ketones, such as e.g. Formaldehyde, acetaldehyde, butyraldehyde, acetone, methyl ethyl ketone.
• reaction products of the aromatic polyisocyanate mixtures mentioned are also suitable with 0.2-50 mol% Polyols, provided that the viscosity of the reaction products thus obtained does not exceed 50,000 cP at 25 ° C and the NCO content of the reaction products is at least 6% by weight.
• Suitable polyols for modifying the starting materials are, in particular, the polyether and / or polyester polyols known from polyurethane chemistry in the molecular weight range from 200 to 6000, preferably 300 to 4000, and low molecular weight polyols in the molecular weight range from 62 to 200. Examples of such low molecular weight polyols are ethylene glycol, propylene glycol, glycerin, Trimethylolpropane, 1,4,6-hexanetriol.
• Particularly preferred isocyanatoaryl-sulfonic acids are the sulfonation products of 2,4-tolylene diisocyanate and mixtures of 2,4- and 2,5-tolylene diisocyanate, furthermore sulfonation products of the di- and polyisocyanates, which are partially aromatic by sulfonation of aniline / formaldehyde condensates Get polyisocyanates.
• 2,4-tolylene diisocyanate and mixtures of 2,4- and 2,5-tolylene diisocyanate furthermore sulfonation products of the di- and polyisocyanates, which are partially aromatic by sulfonation of aniline / formaldehyde condensates Get polyisocyanates.
• Partially sulfonated polyisocyanate mixtures such as those obtained by phosgenation of aniline / formaldehyde condensates and described in German Offenlegungsschriften 2,227,111, 2,359,614 and 2,359,615 are very particularly preferred.
• Suspensions of diisocyanatotoluene-sulfonic acid dimers and diisocyanatodiphenylmethane sulfonic acid dimers in diisocyanatotoluene or diisocyanatodiphenylmethane are also particularly preferred.
• the isocyanatoarylsulfonic acids to be used in the process according to the invention or their mixtures with non-sulfonated aromatic polyisocyanates are prepared by the known processes of the prior art or in analogy to the known processes of the prior art, as can be seen, for example, from the publications already mentioned, or from U.S. Patent No. 3,826,769.
• the processes of German patent applications P 25 24 476.2 or P 26 15 876.9 are also suitable for the preparation of isocyanatoarylsulfonic acids which can be used in the process according to the invention.
• solutions or suspensions of the exemplified isocyanatoarylsulfonic acids in aliphatic polyisocyanates such as, for example, tetramethylene diisocyanate or hexamethylene diisocyanate and / or in cycloaliphatic or mixed aliphatic-cycloaliphatic polyisocyanates such as, for example, 4,4'-diisocyanatodicyclohexylmethane, 2,4 - or, 2,6-diisocyanato-hexahydrotoluene or 1-isccyanato-3,3,5-trimethyl-5-isocyanatomethyleyelohexane.
• aliphatic polyisocyanates such as, for example, tetramethylene diisocyanate or hexamethylene diisocyanate and / or in cycloaliphatic or mixed aliphatic-cycloaliphatic polyisocyanates such as, for example, 4,4'-diis
• solutions or suspensions of the isocyanato-arylsulfonic acids in aromatic, aliphatic or cycloaliphatic monoisccyanates can also be used.
• the latter compounds are phenyl isocyanate, tusyl isocyanate, n-hexyl isocyanate, 6-chloro-hexyl isocyanate, cyclohexyl isocyanate or methoxymethyl isocyanate.
• sulfonated aromatic monoisocyanates such as, for example, phenyl isocyanate as isocyanatoaryl
• sulfonic acid in combination with unsulfonated polyisocyanates of the type mentioned by way of example.
• the type and proportions of the process according to the invention Settling isocyanates and the degree of sulfonation are often chosen such that the equivalent ratio of isocyanate groups, which are sometimes present in dimerized form, to sulfonic acid groups> 1: 1, in particular between 1.05: 1 and 50: 1, preferably between 2: 1 and 30: 1 , lies.
• a ratio between 2: 1 and 12: 1 is very particularly preferred.
• isocyanato sulfonic acids are those aromatic mono-, di- or polyisocyanates which contain more than one sulfonic acid group and in particular two or three sulfonic acid groups.
• isocyanatopolysulfonic acids are described in DT-OS 2,615,876. If monoisocyanatodisulfonic acids are used (with), the equivalent ratio of NCO groups to SO 3 H groups can also be between 1: 1 and 0.5: 1.
• Monoisocyanato sulfonic acids are preferably used for the preparation of hydroxy compounds with terminal sulfonic acid or sulfonate groups, e.g. B. the sulfonation products of phenyl isocyanate, m-tolyl isocyanate, p-tolyl isocyanate, p-chlorophenyl isocyanate, p-nitrophenyl isocyanate, p-methoxyphenyl isocyanate, p-chloromethyl-pheryl isocyanate, m-chlorophenyl isocyanate, m-chloromethyl-phenyl isocyanate.
• B the sulfonation products of phenyl isocyanate, m-tolyl isocyanate, p-tolyl isocyanate, p-chlorophenyl isocyanate, p-nitrophenyl isocyanate, p-methoxyphenyl isocyan
• the quantitative ratio between polyhydroxy compounds and isocyanatosulfonic acid is usually chosen so that OH-functional products with a molecular weight below 12,000 and preferably below 6,000 are formed. A molar excess of hydroxy-functional components is therefore used, at least 1.5 OH groups being to be accounted for by one NCO group.
• NCO groups are not only to be understood as NCO groups present in free form, but also as dimerized NCO groups present in the form of uretdione groups. It is particularly preferred, the hydroxy compounds used as the starting material only proportionally with sulfonic acid groups to modify, in which can be used in an NCO group to 'to 30 OH groups. An equivalent ratio of OH groups to NCO groups between 2 and 20 is preferred.
• monoisocyanates which contain 1 to 3 sulfonic acid groups can also be used in the context of the present invention. These monoisocyanates are reacted with the starting hydroxy compounds in molar amounts.
• the reaction of the starting hydroxy compounds with the isocyanates containing sulfonic acid groups takes place in principle in a known manner.
• the hydroxy compounds are introduced and the isocyanate component is added with mixing.
• the isocyanate is liquid, as is the case, for example, with partially sulfonated MDI types, the mixing of the components and the subsequent reaction can easily take place at room temperature or at a slightly elevated temperature.
• the choice of temperature in this case depends exclusively on the viscosity of the reaction mixture and on the desired duration of the reaction.
• solid isocyanatoaryl, mono- or polysulfonic acids a suspension is primarily formed during the mixing and it is advisable to carry out the reaction at a temperature at which the solid isocyanate dissolves rapidly.
• Solid isocyanatosulfonic acids can also be used in the form of solutions in organic solvents, liquid esters of an inorganic or organic acid of phosphorus being preferred as solvents (DT-OS 2 650 172).
• any inert solvents such as hydrocarbons, halogenated hydrocarbons, ethers, esters and ketones can of course be added to the reaction mixture.
• the reaction in the absence of solvents or with the small amounts of solvents which are used for pasting or dissolving solid isocyanatosulfonic acids is preferred.
• a preferred procedure consists in the production of asymmetrical hydroxy compounds using the different reactivity of the isocyanate groups.
• a diisocyanatoarylsulfonic acid can first be primed with a monofunctional alcohol, a fatty acid, an amino alcohol. or sec. Amine reactions, e.g. B. 20-70% and then bring the remaining NCO groups to reaction with a di- or polyhydrory compound.
• the surfaces can active properties can be varied in many ways.
• the monofunctional compounds which can be used in addition to the polyhydroxy compounds already listed include e.g. Methanol, ethanol, isopropanol, n-butanol, glycol monomethyl ether, glycol monoethyl ether, diglycol monomethyl ether, n-octanol, n-dodecanol, oleyl alcohol, stearyl alcohol, hydroxy-functional fatty acid ester of glycerol, trimethylol propane, and trimethylol ethanol, stearic acid, linoleic acid, coconut oil fatty acid amino alcohols of this type can be regarded approximately as monofunctional in the context of the procedure described above, owing to the greatly different reactivity of the amino and hydroxy functions), butylamine, sec. butylamine, coconut fatty amine.
• stepwise preparation of such asymmetrical hydroxy compounds is particularly preferably carried out in a solvent, e.g. in acetone or an organic phosphoric acid ester.
• a solvent e.g. in acetone or an organic phosphoric acid ester.
• Short-chain hydrophilic monofunctional compounds are preferably combined with predominantly hydrophobic polyhydroxy compounds and long-chain hydrophobic monofunctional compounds are preferably combined with hydrophilic polyhydroxy compounds.
• the sulfonic acid groups containing hydroxy compounds can be completely or partially neutralized with inorganic or organic bases.
• Suitable neutralizing agents are, for example, organic bases such as monofunctional primary, secondary and tertiary amines such as methylamine, diethylamine, triethylamine, trimethylamine, dimethylamine, ethylamine, tributylamine, Pyridine, aniline, toluidine, alkoxylated amines such as Ethanolamine, diethanolamine, triethanolamine, methyldiethanolamine, dimethylaminoethanol, oleyldiethanolamine, and polyfunctional polyamines, in which the individual amino groups may have different basicity, such as, for example, the polyamines obtained by hydrogenating addition products of acrylonitrile to primary and secondary amines, per- or partially alkylated polyamines such as N, N-dimethylethylenediamine, furthermore compounds such as aminopyridine, N, N-dimethylhydrazine; 2.
• neutralizing agents are guanidines, guanidine carbonate, urea, methylurea, dimethylurea, caprolactam, dimethylformamide, dimethylacetamide, pyrrolidone, and solid inorganic bases such as calcium oxide, calcium hydroxide, calcium carbonate, magnesium oxide; Magnesium carbonate, dolomite, lithium hydroxide, lithium carbonate, zinc oxide, zinc carbonate and basic inorganic fillers.
• the products according to the invention are valuable starting materials for the production of polyurethane plastics by the isocyanate polyaddition process. They are suitable, for example, for the production of compact or cellular elastomers, soft foams and rigid foams, particularly when high demands are placed on the crosslinking density, the fire behavior or the degradability.
• the polyhydroxy compounds according to the invention are suitable, for example, for the production of cushioning materials, mattresses, and elastic ones Underlays, car seats, damping materials, shock absorbers, construction materials, soundproofing insulation, moisture-absorbing materials, eg in the hygiene sector, for the production of substrates for growing plants, as well as for heat and cold protection.
• polyhydroxy compounds according to the invention are very particularly suitable for producing inorganic-organic plastics, for example in analogy to the procedures described in DT-PS 2 310 559, DT-OS 2 227 147, 2 359 608, and for surface coatings, impregnations and adhesives.
• the products according to the present invention are suitable as versatile surface-active compounds, e.g. as emulsifiers.
• a particular advantage of the hydroxy compounds according to the invention is their increased polarity.
• these products are well tolerated with low-molecular glycols such as ethylene glycol, diethylene glycol, 1,4-butanediol, glycerin. Mixtures are homogeneous and therefore stable in storage.
• reaction of the polyhydroxy compounds according to the present invention with polyisocyanates containing sulfonic acid ester groups is particularly favorable.
• the use of the compounds according to the invention is particularly recommended when polyisocyanate components and poly- Hydroxy components initially form emulsions due to incompatibility, which only become homogeneous after a certain induction time. Even very small amounts of the products according to the invention favor the formation of particularly fine-particle emulsions which react much more quickly. Furthermore, the new products influence the pore structure of foams made from them and in many cases bring about a desirable increase in shrub hardness. Finally, the products are also suitable for hydrophobicizing surface-modified inorganic fillers.
• Example 5 The procedure is as in Example 5, but starting from an ent speaking polyether with OH number 28. A yellow-brown, viscous, modified polyether is obtained, OH number: 28.1; Acid number: 4, 7.
• uretdione of diisocyanatctoluenesulfonic acid 200 g are triturated with 373 g of toluene and mixed with 10 kg of a polypropylene glycol ether started on trimethylolpropane with 17% terminal ethylene glycol ether groups of OH number 35 at 50 ° C. with stirring. The temperature is then raised to 60 ° C and the toluene is stripped off by applying a water jet vacuum. The uretdione dissolved practically quantitatively within 9 hours. The modified polyether is finally filtered through a fine metal sieve at 60 ° C. OH number: 34.5; Acid number: 4, 3; Sulfur content: 0.2%.
• the product goes into solution after a short time at 60 ° C.
• toluene-moist uretdione of diisoeyanatotoluenesulfonic acid corresponding to 300 g of dry substance, are mixed with 550 g of toluene thoroughly ground and added to 15 kg of a polypropylene glycol ether started on trimethylolpropane with 13% terminal ethylene glycol ether groups of OH number 28 at 50 ° C with stirring, then the mixture is heated to 65 ° and stirred for 5 hours, during which time the majority of the uretione is in solution goes.
• the foams obtained correspond in mechanical properties and fire behavior to the foam from Example 14.
• the comparison foam requires considerably longer periods of time to rise and harden than the foams described in the examples.
• the surface also remains sticky for much longer.

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• Polyurethanes Or Polyureas (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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• 1977
  • 1977-08-03 DE DE19772735013 patent/DE2735013A1/de not_active Withdrawn
• 1978
  • 1978-07-24 EP EP78100487A patent/EP0000724B1/fr not_active Expired
  • 1978-07-24 DE DE7878100487T patent/DE2860598D1/de not_active Expired
  • 1978-07-31 US US05/929,615 patent/US4174434A/en not_active Expired - Lifetime
  • 1978-08-01 IT IT50566/78A patent/IT1106862B/it active
  • 1978-08-01 JP JP9324478A patent/JPS5427536A/ja active Pending
• 1979
  • 1979-06-15 US US06/048,921 patent/US4224418A/en not_active Expired - Lifetime

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