EP0000724B1 - Composés contenant des groupes hydroxylés et des groupes uréthane-aryle-acide sulfonique, leur procédé de préparation et leur application comme composants de réaction avec des polyisocyanates - Google Patents

Composés contenant des groupes hydroxylés et des groupes uréthane-aryle-acide sulfonique, leur procédé de préparation et leur application comme composants de réaction avec des polyisocyanates Download PDF

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Publication number
EP0000724B1
EP0000724B1 EP78100487A EP78100487A EP0000724B1 EP 0000724 B1 EP0000724 B1 EP 0000724B1 EP 78100487 A EP78100487 A EP 78100487A EP 78100487 A EP78100487 A EP 78100487A EP 0000724 B1 EP0000724 B1 EP 0000724B1
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Prior art keywords
groups
compounds
molecular weight
polyisocyanates
sulfonic acid
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EP78100487A
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German (de)
English (en)
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EP0000724A1 (fr
Inventor
Dieter Dr. Dieterich
Gerhard Dr. Ballé
Hans Georg Dr. Schmelzer
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Bayer AG
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Bayer AG
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—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 has been 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, for. B. foams made from it give improved fire behavior and high frequency weldability.
  • the present invention thus relates to at least one OH-functional chain and at least one urethano-arylsulfonic acid-containing compound having an 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 at least one OH-functional chain and at least one urethano-aryl-sulfonic acid group-containing compound having an average molecular weight of 300 to 12,000, characterized in that compounds having a molecular weight of 62 to 10,000, the at least two Have hydroxyl groups, are reacted at 0-190 ° C with aromatic isocyanatosulfonic acids, the equivalent ratio of the total amount of isocyanate groups (including those optionally in dimerized Form isocyanate groups) to sulfonic acid groups 0.5 to 50 and the equivalent ratio of the sum of the hydroxyl groups of the compounds having at least two hydroxyl groups to NCO groups is 1.5 to 30.
  • the present invention 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 of isocyanatoarylsulfonic acid which may be present, with the formation of higher molecular weight new polyhydroxy compounds which contain at least some urethane groups and one or more free sulfonic acid Groups included.
  • the sulfonic acid groups can then be completely or partially neutralized with conventional inorganic or organic bases.
  • the hydroxyl-containing polyesters are z. B. those as they are mentioned in DE-A 2 647 482, pages 8-9.
  • two hydroxyl-containing polyethers, polyethers modified by vinyl polymers, polythioethers, polyacetals, hydroxyl-containing polycarbonates and polyesteramides and polyamides are, for. B. those as described in DE-A 2 647 482, pages 9, 10 and 11.
  • polyhydroxyl 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) take place directly in situ in the above-mentioned compounds containing hydroxyl groups leaves.
  • 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.
  • the sulfonation products of all known aromatic polyisocyanates can be used as isocyanatoarylsulfonic acids.
  • aromatic polyisocyanates which can be used in the form of their sulfonation products in the process according to the invention are those as described in DE-A 2 647 482, pages 5 and 6.
  • Phosgenation products of condensates of aniline and aldehydes or ketones such as, for. B. acetaldehyde, propionaldehyde, butyraldehyde, acetone, methyl ethyl ketone.
  • phosgenation products of condensates of alkyl-substituted anilines, especially toluidines, with aldehydes or ketones such as. B. formaldehyde, acetaldehyde, butyraldehyde, acetone, methyl ethyl ketone.
  • reaction products of the aromatic polyisocyanate mixtures mentioned with 0.2-50 mol% of polyols are also suitable, 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. % is.
  • Suitable polyols for modifying the starting materials are, in particular, the polyether and / or polyester polyols of the molecular weight range 200 to 6000, preferably 300 to 4000, which are known in polyurethane chemistry, and also low molecular weight polyols of the molecular weight range 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 obtained by phosgenation of aniline / formaldehyde condensates, partial sulfonation of aromatic Get polyisocyanates.
  • partial sulfonation of chemically uniform diisocyanates or binary isomer mixtures gives suspensions, while partial sulfonation of multicomponent mixtures produces homogeneous solutions.
  • it is basically irrelevant whether solutions or suspensions are used.
  • 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 unsulfonated 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 US-A 3 826 769.
  • the processes of DE-A 2 524 476 or 2 615 876 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 isocyanato-arylsulfonic acids in aromatic, aliphatic or cycloaliphatic monoisocyanates can also be used.
  • aromatic, aliphatic or cycloaliphatic monoisocyanates examples of the latter compounds are phenyl isocyanate, tosyl isocyanate, n-hexyl isocyanate, 6-chloro-hexyl isocyanate, cyclohexyl isocyanate or methoxymethyl isocyanate.
  • sulfonated aromatic monoisocyanates such as. . B.
  • phenylisocyanate as isocyanatoaryl in combination with non-sulfonated polyisocyanates of the type exemplified above
  • the nature and proportions of the employed in the present process isocyanates, and the degree of sulfonation are often selected so that the equivalent ratio of optionally partly present in the dimerized form - isocyanate groups to sulfonic acid groups> 1: 1 d.
  • h is in particular between 1.05: 1 and 50: 1, preferably between 2: 1 and 30: 1.
  • 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 DE-A 2 615 876. 1 are as follows: Unless Monoisocyanatodisulfonklaren be used (with), the equivalent ratio of NCO groups to SO s H group can also be between 1: 1 and 0.5.
  • 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-phenyl 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, with at least 1.5 OH groups per NCO group.
  • NCO groups are not only to be understood as NCO groups present in free form, but also in the form of uretdione groups dimerized NCp groups. It is particularly preferred to only partially modify the hydroxy-functional compounds used as starting material with sulfonic acid groups, it being possible to use up to 30 OH groups on one NCO group. 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 readily take place at room temperature or even 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 are particularly preferably used in the form of suspensions, pastes or wet powders, using inert solvents, as described in DE-A 2 640 103.
  • 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 (DE-A 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 polyhydroxy compound.
  • the surface-active properties can be varied in many ways.
  • the monofunctional compounds which can be used in addition to the polyhydroxy compounds already listed include, for. B. 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 esters of glycerol, trimethylol propane, and trimethylol ethanol, stearic acid, linoleic acid, linoleic acid, coconut oil Aminopropanol (amino alcohols of this type can be regarded approximately as monofunctional in the course of the procedure described above due to the greatly different reactivity of the amino and hydroxy functions), butylamine, sec. Butylamine, coconut fatty amine.
  • the stepwise preparation of such asymmetrical hydroxy compounds is particularly preferably carried out in a solvent, for. B. 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 hydroxy compounds containing sulfonic acid groups can be completely or partially neutralized with inorganic or organic bases.
  • Suitable neutralizing agents are e.g. B. 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, dimethylaminoethanolamine polyfunctional polyamines in which the individual amino groups may have different basicity, such as. B.
  • 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
  • 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.
  • Weakly basic neutralizing agents such as urea or caprolactam, as well as basic fillers can also be used in excess in relation to the sulfonic acid groups present.
  • 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. B. for the production of compact or cellular elastomers, soft foams and rigid foams, especially when high demands are placed on the crosslinking density, fire behavior or degradability.
  • the polyhydroxy compounds according to the invention are suitable, for example, for the production of upholstery materials, mattresses, elastic underlays, car seats, damping materials, shock absorbers, construction materials, soundproofing insulation, moisture-absorbing materials, eg. B. in the hygiene sector, for the production of substrates for growing plants, and for heat and cold protection.
  • polyhydroxy compounds according to the invention are very particularly suitable for the preparation of inorganic-organic plastics, for example in analogy to the procedures described in DE-C 2310559, DE-A 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. B. 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 polyhydroxy 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 the compression 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 a corresponding polyether with OH number 28. A yellowish-brown, viscous, modified polyether is obtained.
  • uretdione of diisocyanate-toluenesulfonic acid (cf. Example 1) are triturated with 373 g 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.
  • the product goes into solution after a short time at 60 ° C.
  • toluene-moist uretdione of diisocyanatotoluenesulphonic acid (cf. Example 1), corresponding to 300 g of dry substance, are thoroughly triturated with 550 g of toluene and 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 added. The mixture is then heated to 65 ° and stirred for 5 hours, during which most of the uretdione goes into solution. While stirring for a further 3 hours at 65 ° C., the toluene is distilled off in a water jet vacuum, the product is filtered off at 50 ° C. through a metal sieve of approx. 4 g of undissolved material.
  • the foams obtained correspond in mechanical properties and fire behavior to the foam from Example 14.
  • the comparison foam takes 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (5)

1. Composés comportant au moins une chaîne à fonctionnalité OH et au moins un groupe d'acide uréthano-aryl-sulfonique, ces composés ayant un poids moléculaire moyen de 300 à 12.000.
2. Composés suivant la revendication 1, caractérisés en ce qu'ils comportent au moins une chaîne à fonctionnalité OH contenant 15 à 400 chaînons, ces composés ayant un poids moléculaire de 400 à 12.000.
3. Composés suivant la revendication 2, caractérisés en ce qu'ils comportent au moins une chaîne à fonctionnalité OH contenant 30 à 300 chaînons.
4. Procédé de préparation de composés comportant au moins une chaîne à fonctionnalité OH et au moins un groupe d'acide uréthano-aryl-sulfonique, ces composés ayant un poids moléculaire moyen de 300 à 12.000, caractérisé en ce qu'on fait réagir des composés d'un poids moléculaire de 62 à 10.000, comportant au moins deux groupes hydroxy, avec des acides isocyanato-sulfoniques aromatiques à une température de 0 à 190° C, le rapport équivalent entre la quantité totale des groupes isocyanates (y compris les groupes isocyanates éventuellement présents sous forme dimérisée) et les groupes d'acides sulfoniques étant de 0,5 à 50, tandis que le rapport équivalent entre la somme des groupes hydroxy des composés comportant au moins deux groupes hydroxy et les groupes NCO est de 1,5 à 30.
5. Utilisation des composés suivant la revendication 1 comme composants réactionnels pour les polyisocyanates en vue de préparer des produits de polyaddition et/ou des produits de polycondensation.
EP78100487A 1977-08-03 1978-07-24 Composés contenant des groupes hydroxylés et des groupes uréthane-aryle-acide sulfonique, leur procédé de préparation et leur application comme composants de réaction avec des polyisocyanates Expired EP0000724B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2735013 1977-08-03
DE19772735013 DE2735013A1 (de) 1977-08-03 1977-08-03 Hydroxylgruppen und urethano-aryl- sulfonsaeuregruppenenthaltende verbindungen

Publications (2)

Publication Number Publication Date
EP0000724A1 EP0000724A1 (fr) 1979-02-21
EP0000724B1 true EP0000724B1 (fr) 1981-04-08

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EP78100487A Expired EP0000724B1 (fr) 1977-08-03 1978-07-24 Composés contenant des groupes hydroxylés et des groupes uréthane-aryle-acide sulfonique, leur procédé de préparation et leur application comme composants de réaction avec des polyisocyanates

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US (2) US4174434A (fr)
EP (1) EP0000724B1 (fr)
JP (1) JPS5427536A (fr)
DE (2) DE2735013A1 (fr)
IT (1) IT1106862B (fr)

Families Citing this family (15)

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US4482691A (en) * 1983-09-22 1984-11-13 Ppg Industries, Inc. Air-drying fatty acid-modified acrylic resins
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DE3622609A1 (de) * 1986-07-05 1988-01-07 Bayer Ag Verfahren zur herstellung von fluessig-kristallinen nco-polyurethanpraepolymeren und deren verwendung
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US4939184A (en) * 1989-03-07 1990-07-03 University Of Akron Polyurethane foam
GB2235927B (en) * 1989-09-14 1992-10-21 Asahi Chemical Ind A sulfonic acid group-containing polyurethane and a photosensitive resin composition containing the same
FR2690918B1 (fr) * 1992-05-06 2001-12-28 Poudres & Explosifs Ste Nale Utilisation d'un arylsulfonyluréthanne comme résine garnissante dans les vernis à ongles nitrocellulosiques. Nouveaux arylsulfonyluréthannes et nouveaux vernis à ongles nitrocellulosiques.
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EP0000724A1 (fr) 1979-02-21
IT7850566A0 (it) 1978-08-01
IT1106862B (it) 1985-11-18
US4174434A (en) 1979-11-13
JPS5427536A (en) 1979-03-01
DE2860598D1 (en) 1981-04-30
DE2735013A1 (de) 1979-02-15
US4224418A (en) 1980-09-23

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