Bayer Aktiengesellschaft

Agfa-Gevaert Ag

Gerhard Balle

Werner Rasshofer

Dieter Dieterich

Carlhans Suling

Michael Walkowiak

Hans-Hermann Schulz

Kuno Wagner

Hans G Schmelzer

Jurgen Ick

Heinrich Alberts

Gerhard Grogler

Helmut Reiff

Walter Meckel

Wolfgang Himmelmann

Josef Sanders

Holger Meyborg

Gunter Kolb

Wilhelm Saleck

Fritz Nittel

Peter Vehlewald

Reiner Paul

Manfred Munzer

Hansjurgen Rabe

Kurt Schaupp

Bernd W Leusner

Wilhelm Slawyk

Winfried Schoberth

Adolf Wohnhas, Deceased

The present invention is directed to new aromatic diamines containing sulfonic acid aryl esters corresponding to the formula ##STR1## wherein R.sub.1 represents hydrogen, an optionally branched C.sub.1 -C.sub.6 alkyl radical (preferably a methyl group), a C.sub.1 -C.sub.6 alkoxy radical or a halogen atom (preferably chlorine) and

Aromatic diamines containing sulfonic acid aryl esters, a process for

The compounds of the present invention are obtained by the reaction of carbamoyl lactams (from lactams and polyisocyanates) with polyhydric alcohols or monoamino alcohols in the presence of catalytic quantities of a strong basic catalyst, e.g. an alkali metal alcoholate, at elevated temperatures. The polyols contain urea groups and either ester or amide groups and correspond to formula (I) or (II) ##STR1## The polyols are crystalline, relatively high melting compounds which are used as reactants for the synthesis of polyurethane elastomers, in particular in the form of finely divided components in one-component polyurethane reaction mixtures.

Polyhydroxy compounds containing urea groups and either ester or amide

The present invention is directed to a process for the production of optionally cellular, polyurethane and/or polyurethane-urea moldings having an impervious skin by reacting in a closed mold a reaction mixture containing

Process for the production of optionally cellular moldings

Compounds containing from 0.15 to 20.3 wt. % aromatic amino groups are produced by hydrolyzing an isocyanate compound mixed with water and a solvent or solvent mixture at -20.degree. to 185.degree. C. The isocyanate starting material must contain at least two aromatically bound isocyanate groups and an isocyanate content of from 0.5 to 40 wt. %. The water must be used in at least a stoichiometric amount but is preferably used in excess. The solvent or solvent mixture must contain 50-100 wt. % solvent containing ether and/or thioether bonds. A partly water-soluble solvent may be used in an amount no greater than 50 wt. % total solvent. No acidic or basic catalysts are present during the hydrolysis. The product amine may be isolated by phase separation, filtration or extraction. The amines thus-produced are particularly useful in the production of polyurethane(urea)s.

Polyamines and a process for their production

Polyether-based urethane-group-containing polyamines containing polymers and/or copolymers of unsaturated monomers and, optionally, urea and/or biuret and/or allophanate groups are produced by (a) reacting an NCO-prepolymer in aqueous alkaline solution at 0.degree. to 40.degree. C. to form a carbamate; (b) converting this carbamate to an amine by adding an ion exchanger to the reaction mixture; and (c) separating the polyamine from the reaction mixture. The NCO-prepolymers used as starting materials are prepolymers of (i) polyalkylene ether polyols having a molecular weight of from 1,000 to 10,000 containing from 1 to 60 wt. % of graft (co)polymers of unsaturated monomers; and (ii) excess molar quantities of organic polyisocyanate; and optionally, (iii) a low molecular weight chain-extending agent. The product polyamines have a molecular weight of from 1,000 to 10,000 and contain from 0.65 to 59.3 wt. % graft (co)polymer and from 0.11 to 2.9 wt. % terminal NH.sub.2 groups attached to the ethers by urethane groups in the polyisocyanate. The product polyamines are particularly useful in the production of polyurethanes.

Polymer-containing polyether polyamines and a process for the production

A process of making radically polymerizable compositions suitable for the production of impact resistant optically clear glass like plastic and forming the glass from such compositions is disclosed. Also taught are the polymerizable compositions and the final glass produced. An isocyanate terminated prepolymer based upon a polyol selected from polyesters, polyester amides, polycarbonates and polyacetals and diisocyanates selected from branched aliphatic isocyanates, cycloaliphatic isocyanates and aliphatic or cycloaliphatic isocyanates graft polymerized with vinyl monomers is chain extended with aliphatic or cyloaliphatic diamines while in solution in vinyl monomers consisting mainly of methacrylic acid esters. The chain extension is carried out with a deficit of amine and preferably to a viscosity at 20% solids in the vinyl monomers of between 200 and 30,000 cP at 20.degree. C. The composition is then radically polymerized to form the high impact glass like plastic alloy.

High-impact polymer alloys

Polymer-containing polyether polyamines containing terminal aromatically-bound amino groups are produced by in situ polymerization of a polyether polyamine with an olefinically unsaturated monomer. The polyether polyamine starting material must have terminal aromatic amino groups, a molecular weight of from 800 to 10,000 and an aromatic amino group content of from 0.3 to 16 wt. %. Suitable olefinically unsaturated monomers include .alpha.,.beta.-unsaturated nitriles, aromatic vinyl compounds, .alpha.,.beta.-unsaturated carboxylic acids and esters thereof, vinyl esters, vinyl halides, vinylidene halides, .alpha.,.beta.-unsaturated carboxylic acid amides and aminoalkyl esters of unsaturated carboxylic acids. Acrylonitrile/styrene mixtures are preferred monomers. The starting materials are employed in quantities such that the product modified polyether polyamine contains from 1 to 60 wt. % polymer or graft-polymer. The product polyamines are particularly useful in the production of polyurethanes.

Process for the production of polymer-containing aromatic polyether

Polymer modified polyamines having a polymer content of from 1 to 30 wt. % and an aromatic amino group content of from 1 to 12.5 wt. % are produced by hydrolyzing a polyisocyanate prepolymer in an aqueous alkaline medium. The polyisocyanate prepolymer is polymer modified by in situ polymerization of either the prepolymer or the isocyanate used in making the prepolymer with an unsaturated monomer in the presence of a radical forming polymerization catalyst in a manner such that a solution and/or dispersion is formed. The prepolymer is formed from a relatively high molecular weight polyhydroxyl compound, aromatic polyisocyanate, and optionally a chain extender or crosslinking agent. The aromatic polyisocyanate used is from 60-100 wt. % polyisocyanate of the diphenyl alkane series and from 0 to 60 wt. % tolylene diisocyanate. The preferred unsaturated monomer is acrylonitrile containing up to 20 wt. % comonomer. The polymer modified polyamines of the present invention are particularly useful in the production of polyurethanes.

Polymer modified polyamines and a process for their preparation

The instant invention is directed to a process for the production of dispersions of aminoplast condensates in organic polyhydroxyl compounds by the oligo-condensation or polycondensation of substances capable of aminoplast formation, in said organic polyhydroxyl compounds, the improvement wherein said dispersions are reacted at from about -5.degree. C. to about 180.degree. C. with an amine compound selected from the group consisting of:

Process for the production of aminoplast dispersions

The invention relates to bead polymers, useful in the provision of dental articles and made by bead polymerizing a diamine-lengthened polyurethane and a methacrylate. Also included in the invention are the dental articles made using said bead polymers.

Shaped dental articles

The present invention relates to a process for the production of modified polyether polyols by the radical polymerization of a mixture of acrylonitrile, styrene, a salt of an .alpha.,.beta.-unsaturated monocarboxylic or polycarboxylic acid containing a primary, secondary or tertiary monoamine or polyamine and optionally copolymerizable compounds with a polyether polyol.

Process for the production of modified polyether polyols and their use

The instant invention is directed to a process for the production of dispersions of aminoplast condensates in organic polyhydroxyl compounds by the oligo-condensation or polycondensation of substances capable of aminoplast formation, in said organic polyhydroxy compounds, the improvement wherein said dispersions are reacted at from about -5.degree. C. to about 180.degree. C. with an amine compound selected from the group consisting of:

A two-phase bead polymer having an average bead diameter of 10 to 120.mu., and comprising (A) 88 to 99.5% by weight of a polymer of polymerized units of at least one methacrylic acid ester containing from 1 to 10 carbon atoms in the aliphatic, saturated alcohol component, the methacrylic ester polymer, optionally, containing up to 30% by weight of copolymerized units of at least one monomer selected from acrylic acid esters containing from 1 to 10 carbon atoms in the aliphatic saturated alcohol component, hydroxyalkyl esters of methacrylic acid containing from 2 to 4 carbon atoms in the alkyl group, styrene, vinyl acetate, (meth)acrylamide, (meth)acrylic acid and/or itaconic acid, and (B) 0.5 to 12% by weight of a polyurethane.

Process for the production of bead polymers

The instant invention is directed to a process for the preparation of modified polyether polyols comprising polymerizing of from 1 to 50 parts by weight of a mixture of 20 to 100% by weight (based on the total quantity of monomers) of acrylonitrile and 0 to 80% by weight of styrene in 50 to 99 parts by weight of the polyether polyol in the presence of a polymerization initiator which yields radicals, wherein said polymerization is carried out in the presence of from 0.1 to 1.5% by weight, based on the total quantity of monomers put into the process, of a compound of the formula:

Polyurethane foams and elastomers based on modified polyether polyols

The instant invention is directed to compounds having an average molecular weight of from 300 to 12,000, containing: at least one hydroxyl group and at least one urethano-aryl-sulfonic acid group and a method for their preparation. The process is characterized as a process for the preparation of compounds having a number average molecular weight of from 300 to 12,000 having at least one hydroxyl group and at least one urethano-aryl-sulfonic acid group, comprising: reacting at from 0.degree. to 190.degree. C. (A) compounds having a molecular weight of from 62 to 10,000 having at least two hydroxyl groups; with (B) aromatic isocyanato sulfonic acids, wherein the equivalent ratio of the total quantity of isocyanate groups (including any isocyanate groups present in dimerized form) to sulfonic acid groups is from 0.5:1 to 50:1 and the equivalent ratio of the sum of hydroxyl groups in (A) to NCO groups is from 1.5:1 to 30:1. The invention is also directed to the product by the process.

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Leverkusen, Germany

Gerhard Balle