Air Products and Chemicals, Inc.

Dixon, Dale D.

Burgoyne, William F., Jr.

Milligan, Barton

Casey, Jeremiah P.

Pinschmidt, Robert K., Jr.

Dale D Dixon

William F Burgoyne, Jr

Michael E Ford

Robert K Pinschmidt, Jr

William Franklin Burgoyne, Jr

Randall J Daughenbaugh

Frederick L Herman

Larry J Hayes

Gerald J Mantell

Jeremiah P Casey

Joel Erwin Goldstein

Barton Milligan

Robert K Pinschmidt

Michael S Chen

Robert L Fowlkes

Thomas J Edwards

Burgoyne, Jr William F

William Mayo Smith, Jr

A compound represented by the following formula: ##STR1## wherein R is a C.sub.3 -C.sub.24 olefinically unsaturated organic radical having functionality which renders the nitrogen atom electron deficient, the olefinic unsaturation functionality being polymerizable,

Polymers of self- and diol reactive formaldehyde-free crosslinking

The invention relates to an improved process for producing alkenylated aromatic amines which involves the catalytic reaction of an aromatic amine with a diene. The improvement resides in using a solvent in which the aromatic amine and diene are soluble in the proportions present in the reaction but inert to the reaction.

Process for the catalytic alkenylation of arylamines with conjugated

This invention relates to a process for producing ring alkylated aromatic amines. In the process an aromatic amine is reacted with an olefin using gamma alumina as a catalyst. Under the conditions of the process the catalyst is extremely active and with amines that are capable of alkylation at the ortho and para positions, high selectivity to the ortho alkylated isomer can be achieved. The catalyst is also effective for producing unsymmetrical disubstituted alkyl aromatic amines, e.g., ethyl or propyl toluidine where one ortho position is substituted with a methyl group and the other substituted with an ethyl or propyl group.

Ortho-alkylated aromatic amines via gamma alumina catalyst

This invention relates to a process for producing ring alkylated aromatic amines where the alkyl substituent is ortho to the amino group by reacting an N-alkylated aromatic amine with a C.sub.2-10 olefin in the presence of a solid phase acidic catalyst, e.g., silica-alumina or a zeolite. High conversion and selectivity is achieved by maintaining a mole ratio of olefin to amine of from about 1-10:1 and an operating pressure of at least 50 psig.

Formation of ortho-alkylated aromatic amines from N-alkylated aromatic

Compounds corresponding to the formula: ##STR1## wherein: each R.sub.1 is independently selected from H, a straight chain or branched C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.8 alkoxy, C.sub.2 -C.sub.10 alkenyl or C.sub.3 -C.sub.7 cycloalkenyl group;

N,N'-bis(alkoxyalkyl)-N,N'-(2-haloacetyl)phenylenediamines

This invention relates to organic materials normally susceptible to gradual degradation in the presence of oxygen during use over an extended period of time and of the type in which it is customary to add an antioxidant thereto to prevent degradation. The improvement constituting the basis of this invention comprises including an alkenylated toluenediamine having one alkenyl group ortho to an amine group. More particularly, the alkenylated toluenediamines suited as antioxidants are represented by the formulas: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hydrogen, C.sub.1 to C.sub.3 aliphatic, or R.sub.1 and R.sub.2 or R.sub.3 are bridged via an alkylene radical --(CH.sub.2).sub.y -- wherein y=2 to 5, and at least one of R.sub.1, R.sub.2, R.sub.3, R.sub.4 or R.sub.5 is C.sub.1 or greater.

Alkenylated toluenediamines as antioxidants for organic materials

Compounds having utility as herbicides for the premergement treatment and control of grasses and weeds in crops such as rice and having the general structural formula: ##STR1## wherein each R.sup.1 is independently H or a straight chain or branched C.sub.1-10 alkyl or alkoxy group; R.sup.2 is a straight chain or branched C.sub.1-10 alkylene group; R.sup.3 is --CH.sub.2 (CH.sub.2).sub.m O(CH.sub.2).sub.n CH.sub.3 or ##STR2## where both m and n are integers from 1 to 4; and X is a halogen.

Unsaturated haloacetanilides

This invention relates to a process for producing mono-ortho-ethyl- aniline in high selectivity and at high conversion using a silica-alumina catalyst. The reaction is carried out using a fixed bed reactor. Diethylaniline derivatives are avoided by maintaining preselected mole ratios of ethylene to aniline, preselected temperatures and preselected reaction times.

Process for producing mono-ortho-ethyl-aniline using silica-alumina

This invention relates to a process for producing mono-ortho-tert-butyl-aniline in high security selectivity and at high conversion using a silica-containing catalyst. The reaction is carried out using a fixed bed reactor. Di-tert-butyl derivatives are avoided by maintaining preselected mole ratios of isobutylene to aniline, preselected temperatures and preselected reaction times.

Process for producing mono-ortho-tert-butyl-aniline using silica-alumina

Self- and diol reactive formaldehyde-free crosslinking monomers and

This invention relates to alkenylated diphenyldiisocyanates having at least one alkenyl group ortho to an isocyanate group. More particularly the diphenyldiisocyanates are represented by the formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hydrogen, C.sub.1-3 aliphatic, phenyl, halogen or alkoxy radicals, or R.sub.2 and R.sub.4 or R.sub.5 are bridged via an alkylene radical --(CH.sub.2).sub.y -- wherein y=2 to 5 provided not more than one is phenyl, halogen, or alkoxy, X is methylene, alkylene, or branched C.sub.1 -C.sub.6 alkylene group, oxygen, sulfur, carbonyl, sulfonyl or fluoroalkylene group, n is 0 or 1 and z is 0 or 1. The above described alkenylated diphenyldiisocyanates have been found to be well suited for preparing crosslinkable condensation polymers by providing pendant unsaturation for post curing and polymerization. They are also well suited for preparing polyurethane and polyurea elastomer systems.

Alkenylated diphenyldiisocyanates for use in preparing polyurethane/urea

This invention relates to a class of alkenylated toluenediamines and phenylenediamines having at least one alkenyl group ortho to an amine group. More particularly the aryldiamines are represented by the formula: ##STR1## wherein R is hydrogen or C.sub.1 -C.sub.3 aliphatic, R.sub.1 is hydrogen, R.sub.2 is C.sub.2 -C.sub.4, aliphatic and R.sub.1 and R.sub.2 form an alkylene radical (CH.sub.2).sub.y wherein y=3 or 4, and x is one or two. The above described alkenylated aryldiamine, hereafter referred to as diamino-.beta.-alkyl styrenes, have been found to be well suited as antioxidants and as tri-and tetra functional chain extenders in forming polyurethane/urea elastomers systems and for providing pendant unsaturation for post curing and polymerization.

Cycloalkenyl aryldiamines

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

This invention relates to a class of alkenylated toluenediisocyanates having at least one alkenyl group ortho to an isocyanate group. More particularly the toluendiisocyanates are represented by the formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hydrogen, C.sub.1-3 aliphatic, phenyl, halogen or alkoxy radicals, or R.sub.2 and R.sub.4 or R.sub.5 are bridged via an alkylene radical --(CH.sub.2).sub.y --wherein y=2 to 5, and x is one or two provided that in said formula at least one of R.sub.1, R.sub.2, R.sub.3, R.sub.4 or R.sub.5 is C.sub.1 or greater. The above described alkenylated toluenediisocyanates have been found to be well suited for preparing crosslinkable condensation polymers by providing pendant unsaturation for post curing and polymerization. They are also well suited for preparing polyurethane and polyurea elastomer systems.

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Kutztown, PA, United States of America

Dale D Dixon