Air Products and Chemicals, Inc.

Other

Dixon, Dale D.

Burgoyne, William F., Jr.

Milligan, Barton

Casey, Jeremiah P.

Jeremiah P Casey

William F Burgoyne, Jr

Barton Milligan

Peter A Lucas

Susan M Clift

William Edward Starner

Kenneth Merle Kem

Thomas A Manuel

Gamini Ananda Vedage

Kevin Rodney Lassila

Michael E Ford

Dale D Dixon

Richard Van Carr

Michael Langsam

Robert G Petrella

Jeffrey Raymond Quay

George J Wasilczyk

Michael J Fasolka

Joel Erwin Goldstein

William Franklin Burgoyne, Jr

Marshall L Spector

Menas S Vratsanos

Roland E Grandin

Herbert F Strohmayer

Polyurethane-urea elastomers are made using as a chain extender 2-methyl-1,3-propanediol-bis-p-aminobenzoate which is the reduction product from hydrogenating 2-methyl-1,3-propanediol-bis-p-nitrobenzoate. The latter composition is preferably made by esterifying p-nitrobenzoic acid and 2-methyl-1,3-propanediol using a stoichiometric excess of the diol initially, adequate to render the reaction mixture processible, and after converting to a nonvolatile form sufficient diol to form diester with substantially all of the acid, removing free diol by distillation while continuing the esterification of unreacted acid and transesterification of monoester formed to diester. This process, which can be applied broadly to esterification of other nitroaromatic acids with other aliphatic diols, produces high yields of diester without needing extraneous solvent for processibility and with only water as a by-product. The 2-methyl-1,3-propanediol-bis-p-aminobenzoate exhibits reactivity and processing characteristics which make it a suitable drop-in replacement for MoCA in polyurethane-urea elastomer manufacture.

Diamine chain extenders and method of use

N,N'-Di-(branched alkyl)-alkylenediamine-bis-p-aminobenzamides are useful as chain extenders in the manufacture of polyurethane-urea elastomers. These compositions have remarkably uniform reactivities but can be varied structurally to achieve a range of processibility characteristics by altering the melting points of the chain extenders. The preferred compounds melt in a range of 50.degree. to 175.degree. C. while exhibiting t.sub.5000 reactivities of about four minutes. The combination of processing characteristics, reactivities and physical properties of the elastomer products offers advantages not available in commonly used diamine chain extenders of the prior art.

Branched alkyl-containing aminobenzamides as chain extenders in

Resins which comprise polymers which contain multiple acetal groups have been developed which are useful for crosslinking and adhesion promotion in coating and adhesive applications. The polymers which make up these resins are prepared by the addition of aminoacetals to polymers containing anhydride functionality. The polymers are modified by titration with a tertiary amine or alkali base.

Multiple acetal containing resins

Resins which comprise polymers which contain multiple acetal groups have been developed which are useful for crosslinking and adhesion promotion in coating and adhesive applications. The polymers which make up these resins are prepared by the addition of aminoacetals to polymers containing anhydride functionality. The polymers are modified by titration with ammonia or a primary or secondary amine which solubilizes the polymer in aqueous systems.

Resins for crosslinking and adhesion promotion

Crosslinking agents are provided which are stable in both the solid state and in solution without undergoing uncontrolled self-crosslinking reactions. The crosslinking agents are formed by the amination of compounds having multiple ester moieties using homogeneous catalysis, and provide for formaldehyde-free crosslinking.

Curative coating system

Crosslinking agents for coating and adhesive applications

Resins which comprise polymers which contain multiple acetal groups have been developed which are useful for crosslinking and adhesion promotion in coating and adhesive applications. The polymers which make up these resins are prepared by the addition of aminoacetals to polymers containing anhydride functionality. Optionally, these polymers may be modified by titration with a tertiary amine or alkali base which solubilizes the polymer in aqueous systems.

Multiple acetal containing resins for crosslinking and adhesion promotion

This invention pertains to alkyl substituted bi(cyclohexylamine) and derivatives having a high trans, trans-isomer distribution. This isomer distribution represents a thermodynamic mixture of the isomers and provides for extended pot life and extended thermal properties in epoxy resins which are not seen with the kinetic isomer mixture. The bridged cyclohexylamine and derivatives are represented by the formula: ##STR1## wherein; R.sup.1 is hydrogen or C.sub.1-4 alkyl;

Thermodynamic mixture of alkyl substituted bi(cyclohexylamine) isomers

This invention pertains to alkyl substituted bi(cyclohexylamine) and derivatives having a high trans,trans-isomer distribution. This isomer distribution represents a thermodynamic mixture of the isomers and provides for extended pot life and extended thermal properties in epoxy resins which are not seen with the kinetic isomer mixture. The bridged cyclohexylamine and derivatives are represented by the formula: ##STR1## wherein; R.sup.1 is hydrogen or C.sub.1-4 alkyl;

Alkyl substituted bi(cyclohexylamines)

This invention pertains to alkyl substituted difunctional cyclohexylisocyanates having an isomer distribution. The isocyanates are represented by the formulas: ##STR1## wherein; R.sup.1 is C.sub.1-4 alkyl; R.sup.2 is C.sub.1-4 alkyl and

Alkyl substituted difunctional cyclohexylisocyanates

The invention pertains to tertiary amines used as catalysts for the preparation of polyurethane foams prepared via the catalytic reaction of a polyisocyanate with a polyol in the presence of blowing agents, etc. The tertiary amine catalysts are prepared by reacting an olefinic nitrile with aliphatic polyol having at least secondary hydroxyl functionality in a ratio less than stoichiometric for providing cyanoalkylated polyol having residual hydroxyl functionality. The resulting cyanoalkylated polyol then is reacted with a secondary amine under conditions for effective reductive alkylation. The tertiary amine catalysts, because of residual secondary hydroxyl functionality, provide for uniform dispersion within a polyurethane, formulation; they provude for additional or extended pot life in polyurethane formulations at temperature below reaction condition, and they are bound by reaction on cure.

Tertiary amine catalysts for polurethanes

The invention pertains to tertiary amines used as catalysts for the preparation of polyurethane foams prepared via the catalytic reaction of a polyisocyanate with a polyol in the presence of blowing agents, etc. The tertiary amine catalysts are prepared by reacting an olefinic nitrile with aliphatic polyol having at least secondary hydroxyl functionality in a ratio less than stoichiometric for providing cyanoalkylated polyol having residual hydroxyl functionality. The resulting cyanoalkylated polyol then is reacted with a secondary amine under conditions for effective reductive alkylation. The tertiary amine catalysts, because of residual secondary hydroxyl functionality, provide for uniform dispersion within a polyurethane formulation; they provide for additional or extended pot life in polyurethane formulations at temperatures below reaction condition, and they are bound by reaction on cure.

Tertiary amine catalysts for polyurethanes

This invention relates to ditertiary-butyl substituted bridged di(cyclohexylamines) where the tert-butyl substituent is alpha to the amine group and to polyepoxide formulations incorporating the di(cyclohexylamine). The formula of the diamine is: ##STR1## wherein R is tert-butyl. The di(tertiary butyl)methylene bridged cyclohexylamines have delayed reactivity when incorporated in epoxy resins and they also enhance physical properties in high resilience polyurethane foams.

Sterically hindered ditertiary butyl bridged di(cyclohexylamines)

The present invention relates to a process for the production of polyurethanes wherein a tertiary amine functionality is incorporated into the side chain of an aromatic diamine, preferably a diaminobenzamide, to form a catalytic polyurethane chain extender. These chain extenders are polyurethane catalysts that provide adequate cure without residual odor and safety hazards associated with the more traditional tertiary amine catalysts. When reacted with the isocyanate reactive group the non-tertiary amine portion of the chain extender is bound to the polymeric network. Diffusion of the catalyst species from the polyurethane has been prevented, thus negating odor and toxicity as problems. These aromatic diamines provide enhanced polyurethane physical properties.

Aromatic diamine catalytic chain extenders

This invention relates to polyepoxide resins cured with an amine composition containing 1-methyl-2,6-cyclohexanediamine. The resulting polyepoxide resins generally are more easily processable and have improved thermal stability, greater elongation and enhanced fracture toughness.

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Emmaus, PA, United States of America

Jeremiah P Casey