Air Products and Chemicals, Inc.

Lim International S.a.

Barton Milligan

Jeremiah P Casey

William Edward Starner

Roland E Grandin

Dale D Dixon

William F Burgoyne, Jr

Walter Sibral

Susan M Clift

George B DeLaMater

Herbert F Strohmayer

Andreas R Schmidt

Robert K Pinschmidt, Jr

Thomas A Johnson

Randall J Daughenbaugh

Der-Shing Huang

Michael J Fasolka

Denise B Taylor

Donald G Miller

Nance D Kunz

Eckhart R Becker

This invention relates to an improved catalytic process for producing 2,2,6,6-tetraalkyl-4-oxopiperidines by the reaction of a ketone and ammonia. The improvement resides in using a catalytic amount of a super acid, i.e., a perfluorinated sulfonic acid polymer or perfluorinated alkyl sulfonic acid as the catalyst.

Process for preparing triacetone amine and other oxopiperidines

This invention relates to improved polyurethane systems prepared by reacting an organic polyisocyanate with a hydroxyl containing compound, the improvement comprising utilizing mono tertiary-alkyltoluenediamine where the tertiary-alkyl group is ortho to an amine group as a chain extender or component thereof. The ortho-tertiary-butyltoluenediamine isomer is particular effective for use in reaction injection molding of polyurethanes and can be formulated with polyol as a chain extender mix.

Polyurethane system using monotertiary-alkyltoluenediamine as a cross

The present invention relates to polyurethanes and a method for making polyurethanes by reacting an organic diisocyanate, a glycol having a molecular weight of 500-5000 and a derivative of 2,6-diaminobenzoic acid or a blend comprising derivatives of 2,4-diaminobenzoic acid and 2,6-diaminobenzoic acid. The addition of the 2,6-diaminobenzoic acid derivative to the composition improves polyurethane processability and performance by decreasing chain extender reactivity and increasing hard segment regularity.

Process of preparing polyurethanes cured with 2,6-idaminobenzoic acid

This invention relates to a polyisocyanate prepolymer for polyurethane/urea elastomer synthesis and to the resulting elastomer. The prepolymer is formed by reacting toluenediisocyanate with a long chain polyol under conditions such that essentially a 2:1 adduct is formed. Excess toluenediisocyanate is removed prior to forming the elastomer.

Process for the preparation of polyisocyanate prepolymers and

This invention relates to a class of tertiary-alkyltoluenediamines having alkyl groups ortho to an amine group. More particularly the aromatic diamines are represented by the formulas: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are C.sub.1-3 alkyl groups or R.sub.2 and R.sub.3 are combined to form a C.sub.5-6 membered ring. The above described alkylated aromatic diamines have been found to be well suited for use as a chain extender in forming polyurethane/urea elastomer systems and the mono tert-butyltoluenediamine isomers have been found to be nonmutagenic in the Ames test.

Mono-tertiary-alkylated toluenediamine and derivatives

This invention relates to urethane linked hydroxy aromatic isocyanates and to a process for producing such urethane linked hydroxy aromatic isocyanates. The compositions are formed by reacting one equivalent aromatic diisocyanate with one equivalent of an alkylene polyol under conditions such that only one of the isocyanate groups react with the hydroxyl group of the polyol. Conditions are controlled such that the urethane linked hydroxy aromatic isocyanates are formed. The resulting product is suited for producing a variety of elastomers including a one component polyurethane elastomer.

Urethane linked hydroxy aromatic isocyanates

This invention relates to a solvent-free process for producing polyurethane/urea elastomers wherein an aromatic diisocyanate is reacted with a compound having active Zerewitinoff hydrogen atoms and an aromatic diamine chain extender. The improvement for producing urethanes having a wide range of properties comprises including a urethane-linked diisocyanate in the polyurethane urea elastomer. The urethane-linked diisocyanate is one that is formed by reacting toluenediisocyanate or substituent thereof with a short chain diol under conditions such that the urethane linked diisocyanate comprises two equivalents isocyanate per equivalent diol.

Process for producing polyurethane/urea elastomers

This invention relates to urethane linked mixtures of 2,4- and 2,6-toluenediisocyanates (ULTDI dimers) having low melting points and to a method of forming these systems. The urethane linked toluenediisocyanates containing from 45-90% of the 2,4- and 10-55% of the 2,6- isomer by weight are formed by reacting two moles of an appropriate isomer mix of toluenediisocyanate, with one mole of a specific alkylene glycol, e.g., 1,2-butanediol, diethylene glycol or dipropylene glycol under conditions such that essentially only one of the isocyanate groups on a toluenediisocyanate molecule reacts with a hydroxyl group of the glycol. Conditions are controlled such that the urethane linked toluenediisocyanates are formed. The resulting product, which has two unreacted isocyanate groups, is suited for producing a variety of elastomers including polyurethane polyurethane/urea or polyurea elastomers.

Low melting urethane linked toluenediisocyanates

This invention pertains to a process for preparing hydroxy mononuclear aromatic compounds by reacting an alkali metal hydroxide with a mononuclear aromatic compound, e.g., benzene, xylene or toluene. The reaction is carried out in the presence of a metallic hydrogenation catalyst, suitably copper, nickel, rhodium or cobalt, the metal being present in an amount sufficient for catalyzing the reaction. The hydroxy mononuclear aromatic compound is then formed by adding a protonating agent to the resulting reaction product, with the protonating agent liberating the hydroxy compound from the salt.

Hydroxy aromatic compounds from alkali metal hydroxide and mononuclear

This invention pertains to a process for preparing polyhydroxy aromatic compounds by reacting an alkali metal hydroxide with a hydroxymononuclear aromatic compound, e.g., phenol or resorcinol. The reaction is carried out in the presence of a metallic hydrogenation catalyst, suitably nickel, or cobalt, the metal being present in an amount sufficient for catalyzing the reaction. The polyhydroxy aromatic compound is then formed by adding a protonating agent to the reaction product, with the protonating agent liberating the hydroxy compound from the salt.

Polyhydroxy aromatic compounds from alkali metal hydroxide and

This invention relates to reinforced tire utilizing polyurea or polyurethane formulations having low hysteresis. The polymer having low hysteresis is formed by reacting a prepolymer of an aromatic isocyanate and a high molecular weight difunctional polyol with a chain extender mix comprising an aromatic diamine and difunctional polyol. In these compositions the aromatic diisocyanate and aromatic diamine are selected so that there is substantial symmetry between the molecules. The reinforcement used is preferably an aromatic polyamide.

Reinforced polyurethane tires

This invention pertains to the synthesis of polyurethane systems having low hysteresis. The systems are generated by reacting a prepolymer of a mononuclear diisocyanate and a polyol with a chain extender mix of a mononuclear aromatic diamine and a polyol. The prepolymer should have a free isocyanate content of from 2 to about 12% by weight and the chain extender mix should have an amine to polyol equivalent from about 0.5 to 5:1.

Polyurethane compositions having low hysteresis

This invention pertains to a process for preparing mononuclear aromatic amines by reacting an alkali metal amide with a mononuclear aromatic compound, e.g., benzene and toluene. The reaction is carried out in the presence of a metallic hydrogenation catalyst, suitably copper, nickel, rhodium or cobalt, the metal being present in an amount sufficient for catalyzing the reaction. The amine then is formed by adding a protonating agent to the resulting reaction product formed by the reaction of the alkali metal amide with the aromatic compound. The addition of the protonating agent liberates the amine.

Aromatic amines from alkali metal amide aminating agent and aromatic

In a process for nitrating aromatics using lower valent nitrating agents in trifluoroacetic acid, the product yield of nitroarenes can be significantly increased by maintaining an excess of nitrating agent over the stoichiometric amount during the reaction.

Nitration of aromatics with nitrogen oxides in trifluoroacetic acid

A composition for preparing polyurethanes comprising an organic polyisocyanate; a poly(silyldiamine) of the unit formula ##STR1## wherein the grouping ##STR2## is a divalent organic radical terminated by two nitrogen atoms with R being a divalent organic moiety, or a divalent alicyclic radical in which R and R.sup.1 with the two nitrogens form a cyclic diamine structure, R.sup.1 is hydrogen or a monovalent hydrocarbon, R.sup.2 is a monovalent hydrocarbon, and n is an integer greater than 1; and a polyol. When poly(silyldiamines) of the above formula are reacted with a polyisocyanate prepolymer and a polymeric polyol, elastomeric polyurethanes having good elastomeric properties are obtained.

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Coplay, PA, United States of America

Barton Milligan