Bayer Aktiengesellschaft

Holger Meyborg

Werner Rasshofer

Gerhard Grogler

Jurgen Schwindt

Herbert Salzburg

Klaus Konig

Dieter Dieterich

Hans J Meiners

Richard Kopp

Manfred Hajek

Rudolf Fauss

Hans-Walter Illger

Werner Mormann

James M Barnes

Kuno Wagner

Helmut Reiff

Walter Meckel

Manfred Bock

Otto Ganster

Gerhard Balle

Heinz Ziemann

Wilhelm Goyert

Christian Weber

Helmut Kleimann

Peter Seifert

Klaus Recker

Armin Zenner

Willi Eifler

Hans-Jurgen Lienert

Polyamines containing from 0.19 to 20.3 wt. % aromatically bound primary amino groups are produced by hydrolyzing an isocyanate group containing compound in the presence of excess water, a tertiary amine and, optionally an ether solvent. The hydrolysis is carried out at a temperature of from -10.degree. to 150.degree. C. in a manner such that the reaction mixture remains substantially homogeneous. The isocyanate starting material contains aromatically bound isocyanate groups and has an NCO-content of from 0.5 to 40 wt. %. The ether solvent must be water soluble and inert with respect to isocyanates. Co-solvents and catalysts may also be included in the reaction mixture. The product polyamines are particularly useful in the production of polyurethanes.

Polyamines and a process for the production thereof

Polyurethane urea elastomers are produced by reacting polyisocyanates with compounds containing at least two isocyanate reactive hydrogen atoms having a molecular weight of 400 to 10,000 and mononuclear or dinuclear aromatic diamines. The aromatic diamines must have at least one sulfonamide group as a substituent on at least one of their aromatic rings. Known chain lengthening agents, activators, blowing agents, auxiliary agents and additives may also be included in the reaction mixture. Polyurethane elastomers produced by this process have excellent mechanical properties. In particular, such elastomers are soft yet have high tear propagation resistance.

Process for the preparation of polyurethane elastomers

Liquid dianhydrohexitol mixtures are prepared from diacylation products of hexitols and compounds such as organic carboxylic acids, carboxylic acid anhydrides, carboxylic acid halides, ketene and carbonic acid ester derivatives. More specifically, such diacylation products are simultaneously dehydrated and isomerized by subjecting them to a temperature of at least 130.degree. C. in the presence of a strong acid to yield diacylated dianhydro-hexitol isomer mixtures. These isomer mixtures are then converted to dianhydro-hexitol isomer mixtures by hydrolysis or transesterification. Suitable strong acids include proton acids, Lewis acids and heterogeneous acid catalysts (e.g., ion exchange resins). The mixtures of the present invention are characterized by a minimal tendency towards crystallization. These mixtures are particularly useful as chain extending agents in the production of polyurethanes.

Process for the production of dianhydrohexitol mixtures and the

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

The invention relates to an improved process for the production of polyamines containing urethane and/or urea and/or biuret and/or isocyanurate groups and, preferably, also alkylene ether, carbonate and/or acetal groups by the alkaline hydrolysis of corresponding compounds containing terminal aliphatic and/or aromatic isocyanate groups. To this end, the compounds containing terminal NCO-groups, preferably NCO-preadducts, are converted by means of selected bases into the carbamates and neutralized by introduction into equivalent quantities of acid or by the simultaneous introduction of the components in equivalent quantities into a reaction vessel, after which the polyamines are directly isolated by methods known per se. The invention also relates to the use of the polyamines obtained by the process for the production of polyurethanes.

Simplified process for the production of polyamines by the alkaline

Polyamines containing aromatically bound primary amino groups having an NH.sub.2 -content of from 0.19 to 20.3 wt % are produced by a single stage process. A compound containing aromatically bound NCO-groups and having an isocyanate content of from 0.5 to 40 wt % is hydrolyzed with an excess of water in the presence of a water-miscible polar solvent and optionally a catalyst. The hydrolysis is carried out at a temperature of from -10.degree. to 150.degree. C. in a manner such that the reaction mixture is substantially homogeneous. The water-miscible polar solvent generally has a boiling point of from 56.degree. to 250.degree. C. and a dielectric constant of at least 10. This polar solvent is used in a quantity of at least 5 parts solvent for every 100 parts of isocyanate. Tertiary amines are the preferred catalysts. These polyamines are particularly useful in the production of polyurethanes.

Polyamines and a process for their production

Liquid dianhydrohexitol mixtures are prepared from diacylation products of hexitols and compounds such as organic carboxylic acids, carboxylic acid anhydrides, carboxylic acid halides, ketene and carbonic acid ester derivatives. More specifically, such diacylation products are simultaneously dehydrated and isomerized by subjecting them to a temperature of at least 130.degree. C. in the presence of a strong acid to yield diacylated dianhydrohexitol isomer mixtures. These isomer mixtures are then converted to dianhydrohexitol isomer mixtures by hydrolysis or transesterification. Suitable strong acids include proton acids, Lewis acids and heterogeneous acid catalysts (e.g., ion exchange resins). The mixtures of the present invention are characterized by a minimal tendency towards crystallization. These mixtures are particularly useful as chain extending agents in the production of polyurethanes.

Process for the production of dianhydrohexitol mixtures and liquid

Polyurethane elastomers are made by reacting organic polyisocyanates with compounds having at least two groups containing isocyanate-reactive hydrogen atoms and a molecular weight of from 400 to 10,000 and a 1,4-monoanhydro-tetritol in accordance with techniques known to those in the art. Known chain-lengthening agents, auxiliaries and additives may be included in the reaction mixture. The reaction mixtures employed in the process of the present invention have a longer pot life than prior art reaction mixtures. The elastomers produced by this process are shrink stable.

Process for the preparation of polyurethane elastomers using diols of

A compound having a terminal isocyanate group is hydrolyzed to produce a polyamine having a urethane and/or a urea and/or a biuret group. More particularly, a carbamate is made by mixing an isocyanate prepolymer having urethane and/or urea and/or biuret groups present with aqueous base solutions at a temperature of from 0.degree. to 0.degree. C. and in quantities such that the equivalent ratio of hydroxyl to isocyanate groups is between from 0,3:1 to .gtoreq.1,01 to 1. The carbamate is then treated with an acid ion exchanger to form an amine. The amine is then removed from any other material which may be present. A preferred polyamine thus-produced corresponds to the general formula: ##STR1## in which each R radical may represent a divalent straight or branched- chain aliphatic radical; a divalent cycloaliphatic radical; a 4,4'- and/or a 2,4'-dicyclohexylmethane radical; or a 2,4- and/or 2,6-methyl cyclohexane radical. Such an amine may be reacted with a polyisocyanate and optionally with other known additives to form a polyurethane plastic or foam.

Polyamines and processes for the production of such polyamines and of

A process for the preparation of 1,4-3,6-dianhydro-hexitols from hexitols by elimination of water is described, characterized in that gaseous hydrogen halide is used as the acid dehydrating agent optionally with carboxylic acids, carboxylic acid halides and/or carboxylic acid anhydrides in quantities of up to 600 mol percent, based on the hexitols, as cocatalysts. The reaction is carried out in the absence of water and organic solvents, preferably using gaseous hydrogen chloride, temperatures of up to 300.degree. C. and pressures of up to 250 bar. Very high yields are obtained after working up of the product by distillation or extraction.

Process for the preparation of 1,4-3,6-dianhydro-hexitols

A compound having a terminal isocyanate group is hydrolyzed to produce a polyamine having a urethane and/or a urea and/or a biuret group. More particularly, a carbamate is made by mixing an isocyanate prepolymer having urethane and/or urea and/or biuret groups present with aqueous base solutions at a temperature of from 0.degree. to 0.degree. C. and in quantities such that the equivalent ratio of hydroxyl to isocyanate groups is between from 0.3:1 to .gtoreq.1.01 to 1. The carbamate is then treated with an acid ion exchanger to form an amine. The amine is then removed from any other material which may be present. A preferred polyamine thus-produced corresponds to the general formula: ##STR1## in which each R radical may represent a divalent straight or branched-chain aliphatic radical; a divalent cycloaliphatic radical; a 4,4'- and/or a 2,4'-dicyclohexylmethane radical; or a 2,4- and/or 2,6-methyl cyclohexane radical. Such an amine may be reacted with a polyisocyanate and optionally with other known additives to form a polyurethane plastic or foam.

A process for the preparation of homogeneous and cellular polyurethane plastics by the reaction of

Process for the preparation of polyurethane plastics using

A solution of a polyurethane in a polyol is made from (a) the reaction product of a polyisocyanate and a diprimary diol, and (b) a polyether in which the reaction product constitutes from 3 to 60 wt. % of the solution. Suitable diprimary diols have a molecular weight of from 90 to 800 and a structure at both hydroxyl groups corresponding to the general formula: ##STR1## in which R.sub.1 represents chlorine, an alkyl, cycloalkyl, aralkyl or aryl radical having from 1 to 10 carbon atoms, which carbon atoms may be substituted or interrupted by chlorine, ester groups, ether groups, amide groups, urethane groups or nitrile groups, and

Solution of a polyurethane in a polyol and a process for using such a

This invention relates to mixtures of polyols which are liquid at room temperature with functional aldoximes as blowing agents, wherein the aldoxime groups react with polyisocyanates to liberate carbon dioxide and are simultaneously incorporated by means of the functional group thereof into the polyurethane formed. The present invention also relates to a process for the production of polyurethane foams using these incorporated reactive blowing agents as the primary blowing agent in combination with blowing agents known in polyurethane chemistry. The process according to the invention described herein is suitable for the production of various polyurethane foams or cellular polyurethane elastomers, particularly including the production of semi-rigid and rigid polyurethane integral skin foams which are obtained by foaming the reaction mixture in closed molds.

Polyol mixtures containing reactive blowing agents and use thereof for

A polymer precursor containing an oxazolin-2-one ring is made by reacting (a) an amino-reactive group containing compound having at least two groups capable of entering into an addition or condensation reaction with primary or secondary aromatically-bound amino groups with (b) an aromatic amine having at least one primary or secondary aromatically-bound amino group and at least one condensed oxazolin-2-one ring. The reactants are used in quantities such that for each aromatically bound primary or secondary amino group there are from 0.95 to 5 groups present in the amino-reactive group containing compound which are capable of reacting with the amino group. These polymer precursors may be used to produce high molecular weight polymers useful in the production of solid molded products, adhesives, foam plastics and coatings.

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Odenthal, Germany

Holger Meyborg