Abstract: A method for making flexible epoxy resins by curing an epoxide and a bis-phenol with an aliphatic secondary diamine having the structural formula (I) or (II): where R1 and R2 are each individually an alkyl, alkenyl, aryl, or arylalkyl group having from about 1 to about 20 carbon atoms, and R3 and R4 are each individually an alkyl or alkenyl group having from about 1 to about 20 carbon atoms, or hydrogen.

Abstract: Certain secondary aliphatic diamines are excellent chain extenders in the formation of polyurethanes, polyurea-polyurethane hybrids, and polyurea polymers, both elastomers and coatings, from both monomeric polyisocyanates and isocyanate-terminated prepolymers using the high-pressure impingement mixing reaction technique. These diamines include 1,4-di(alkylamino)cyclohexanes, 1-methyl-2,4-di(alkylamino)-3,5-dialkylcyclohexanes, N,N′-dialkyl isophoronediamine, 1,3-di(1′methyl-1′-alkylaminoethyl)benzene, and 1,6-di(alkylamino)hexane. These chain extenders may be used alone or in combination with other polyamines and with polyols. A broad spectrum of polymeric materials can be formed with a range of diverse properties.

Abstract: Flexible foam resistant to both photochemical and oxidative degradation result from the use of bis(N-alkylaminocyclohexyl)methanes as curing agents for polyisocyanates or polyisocyanate prepolymers. The chain extenders may be used alone or in combination with other polyamines and with polyols. Where the polyisocyanate or polyisocyanate prepolymer is also aliphatic there is outstanding resistance to yellowing.

Abstract: Bis(N-alkylaminocyclohexyl)methanes are excellent chain extenders in the formation of polyurethane and polyurea polymers, both elastomers and coatings, from both monomeric polyisocyanates and isocyanate-terminated prepolymers. Our chain extenders may be used alone or in combination with other polyamines and with polyols. A broad spectrum of polymeric material can be formed with a range of diverse properties.

Abstract: Rigid urea-modified polyisocyanurate foams with improved dimensional stability and flame retardancy have densities of 0.5-20 p.c.f., a limiting oxygen index greater than 22 and dimensional changes at 100% R.H. and 70.degree. C. of less than 2% in any linear dimension and a method of making same. The method comprises reacting an organic polyisocyanate, a blowing agent and an N,N'-dialkyl aromatic diamine in the presence of a trimerization catalyst and, if water is used as the blowing agent, a blowing catalyst, wherein the N,N'-dialkyl aromatic diamine and an amine produced by water, if used, constitute the sole sources of active hydrogen.

Abstract: Rigid urea-modified polyisocyanurate foams with improved dimensional stability and flame retardancy have densities of 1-12 p.c.f., a limiting oxygen index greater than 22 and dimensional changes at 100% R.H. and 70.degree. C. of less than 2% in any linear dimension and a method of making same. The method comprises reacting an organic polyisocyanate, a blowing agent and an N,N'-dialkyl aromatic diamine in the presence of a trimerization catalyst and, if water is used as the blowing agent, a blowing catalyst, wherein the N,N'-dialkyl aromatic diamine and an amine produced by water, if used, constitute the sole sources of active hydrogen.

Abstract: N,N'-di-sec-alkenyl-or-di-sec-alkyl-substituted methylene diphenyl diamines are effective curing agents for making polyurethane foams from MDI-based polyisocyanates. The diamines are especially advantageous since foams of lower density having lower hardness can be obtained without utilizing chlorofluorocarbous (CFC's) and without sacrificing tensile strength, tear strength, SAG or compression set values.

Abstract: The polyurethanes and polyureas resulting from ambient-temperature-curing isocyanate-terminated urethane prepolymers with N-alkyl-substituted aromatic polyamines and, optionally, with an added polyol, but primary amine-free, in the presence of a combination catalyst comprising an aliphatic carboxylic acid, e.g., adipic, stearic, oleic acids, and an organometallic catalyst containing, e.g., tin, mercury, bismuth, etc. are broadly useful as coating on the surface of objects made of metal, wood, glass, plastic or masonry materials such as concrete, bricks, etc. or as castings cured in situ. One-shot and quasi-prepolymer systems are also disclosed. The diamine N,N'-di-(sec-butyl)-4,4'-methylenedianiline is a particularly useful diamine.

Abstract: N,N'-dialkyl- and diarylphenylenediamines are effective curing agents in combination with other polyamines and polyols in reaction injection molding for a diverse class of polyisocyanates. The diamines provide a broad spectrum of cure times, as well as giving elastomers an interesting and useful diversity of properties. Such polyamines may be used as a constituent in a blend of polyamines as the isocyanate-reactive component, in which case the elastomer may be viewed as predominantly a polyurea, or as a constituent in a blend with polyols, in which case the elastomer may be viewed as an elastomer with both urethane and urea segments.

Abstract: The polyurethanes and polyureas resulting from ambient-temperature-curing isocyanate-terminated urethane prepolymers with N-alkyl-substituted aromatic polyamines and, optionally, with an added polyol, but primary amine-free, in the presence of a combination catalyst comprising an aliphatic carboxylic acid, e.g., adipic, stearic, oleic acids, and an organometallic catalyst containing, e.g., tin, mercury, bismuth, etc. are broadly useful as coatings on the surface of objects made of metal, wood, glass, plastic or masonry materials such as concrete, bricks, etc. or as castings cured in situ. One-shot and quasi-prepolymer systems are also disclosed. The diamine N,N'-di-(sec-butyl)-4,4'-methylenedianiline is a particularly useful diamine.

Abstract: Alkylated polyamines which may be viewed as low molecular weight polymers of x-amino-y-methylenephenyl are effective curing agents in combination with other polyamines and polyols in reaction injection molding for a diverse class of polyisocyantates. Alkylation may range from 5 up to 100 percent to afford polyamines with a broad spectrum of cure times, as well as to give elastomers with an interesting and useful diversity of properties. Such polyamines may be used as a constituent in a blend of polyamines as the isocyanate-reactive component, in which case the elastomer may be viewed as predominantly a polyurea, or as a constituent in a blend with polyols, in which case the elastomer may be viewed as an elastomer with both urethane and urea segments.

Abstract: N,N'-dialkyl- and diaylphenylenediamines are effective curing agents in combination with other polyamines and polyols in reaction injection molding for a diverse class of polyisocyanates. The diamines provide a broad spectrum of cure times, as well as giving elastomers an interesting and useful diversity of properties. Such polyamines may be used as a constituent in a blend of polyamines as the isocyanate-reactive component, in which case the elastomer may be viewed as predominantly a polyurea, or as a constituent in a blend with polyols, in which case the elastomer may be viewed as an elastomer with both urethane and urea segments.

Abstract: N,N'-disubstituted diamines are effective curing agents in combination with other polyamines and polyols in reaction injection molding for a diverse class of polyisocyanates. The diamines provide a broad spectrum of cure times, as well as giving elastomers an interesting and useful diversity of properties. Such diamines may be used as a constituent in a blend of polyamines as the isocyanate-reactive component, in which case the elastomer may be viewed as predominantly a polyurea, or as a constituent in a blend with polyols, in which case the elastomer may be viewed as an elastomer with both urethane and urea segments.

Abstract: The polyureas resulting from curing polyfunctional isocyanates having at least three isocyanate groups with a N,N'-dialkylmethylenedianiline are broadly useful as coatings on the surface of objects made of metal, wood, glass, or plastic. The diamine N,N'-di(2-butyl)4,4'-methylenedianiline is a particularly useful diamine. Biurets are an especially desirable class of polyisocyanates for the polyureas of this invention, particularly those arising from polymethylene diisocyanates and aromatic diisocyanates.

Abstract: Partially alkylated polyamines which may be viewed as low molecular weight polymers of x-amino-y-methylenephenyl are effective curing agents in combination with other polyamines and polyols in reaction injection molding for diverse class of polyisocyanates. Alkylation may range from 5 up to 100 percent to afford polyamines with a board spectrum of cure times, as well as to give elastomers with an interesting and useful diversity of properties. Such polyamines may be used as a constituent in a blend of polyamines as the isocyanate-reactive component, in which case the elastomer may be viewed as predominantly a polyurea, or as a constituent in a blend with polyols, in which case the elastomer may be viewed as an elastomer with both urethane and urea segments.

Abstract: Urethane prepolymers cured with a blend of an aromatic alkyl diamine and a polyhydric alcohol having more than two hydroxyl groups show excellent compression set and tensile properties. Ratios of diamine to alcohol in the blend, expressed as equivalents, may vary from 1:1 to 19:1, with optimum properties in the elastomer often resulting from blends with the ratio 2:1 to 4:1.

Abstract: The polyurethanes resulting from curing isocyanate-terminated urethane prepolymers with a N,N'-dialkylmethylenedianiline are broadly useful as coatings on the surface of objects made of metal, wood, glass, or plastic. Such coatings may be made based on either a 1-pack systemor 2-pack system. The diamine N,N'-di(2-butyl)4,4'-methylenedianiline is a particularly useful diamine.

Abstract: Largely alkylated polyamines which may be viewed as low molecular weight polymers of x-amino-y-methylenephenyl are effective curing agents for a diverse class of urethane prepolymers. The resulting polyurethanes are thermosetting polymers with excellent compression set and tensile strength. Because the properties of the resulting polyurethane vary only slightly near the optimum stoichiometry of curing agent-prepolymer, the use of the curing agents of this invention presents the advantage of being very tolerant of operator mixing error.

Abstract: The polyurea resulting from curing polyfunctional isocyanates having at least three groups with a N,N'-dialkylmethylenedianiline are broadly useful as coatings on the surface of objects made of metal, wood, glass, or plastic. Such coatings may be made based on either a 1-pack system or 2-pack system. The diamine N,N'-di(2-butyl)4,4'-methylenedianiline is a particularly useful diamine. Biurets are an especially desirable class of polyisocyanates for the polyureas of this invention.

Abstract: Polyurethanes may be conveniently made by curing isocyanate-terminated urethane prepolymers with a N,N'-dialkylmethylenedianiline. The diamine N,N'-di(2-butyl)-4,4'-methylenedianiline is a particularly useful diamine. The resulting polyurethanes often are thermoplastic rather than thermosetting, making them especially useful as coatings, adhesives, and sealants. Such secondary aromatic diamines have acceptable pot lives and afford products with a variety of properties.