Diamines isophorone

In the multistep production of IPDI, isophorone is first converted to 3-cyano-3,5,5-trknethylcyclohexanone (231—235), then hydrogenated and ammoniated to 3-aminomethyl-3,5,5-trknethyl-l-aminocyclohexane (1) (236,237), also known as isophorone diamine (IPDA). In the final step IPDA is phosgenated to yield IPDI (2) (238). Commercial production of IPDI began in the United States in 1992 with the startup of Olin s 7000 t/yr plant at Lake Charles, Louisiana (239), and the startup of Hbls integrated isophorone derivatives plant in Theodore, Alabama (240). Hbls has a worldwide capacity for IPDA of 40,000 t/yr. 

The ketimine of isophorone diamine is formed by reacting it with methyl isobutylketone, splitting off water in the process. When said ketimine is added to an isocyanate-terminated prepolymer based on IPDI, a semi-stable system is established with a pot life of several hours. The ketimine is a Schiff base and thus can react even in the absence of water. The complexities and advantages of this system are reviewed by Bock and Halpaap [75] ... 

Figure 6-7. N-Cyclohexyl maleimide, 2,5-diaminonorbornylene, isophorone diamine.

Fatty acid amides of isophorone diamine, 2,5-diaminonorbomylene, and 2,2,4-trimethyl-1,6-diaminohexane are particularly suitable for high-tempera-ture and high-pressure applications [971],... 

Isophorone diamine is synthesized traditionally by aminoreduction of iso-phoronenitrile. Raney cobalt was used for this process. More recently, a new two-step process was patented. The first step consists of synthesizing the imine and the second one of hydrogenating the latter. Ra-Ni was used as catalyst at 150°C and 60 bar hydrogen pressure. Under these conditions, the catalyst reduces the nitrile groups and is able to cleave the N-N bonds, too. Ammonia is required to promote primary amine formation during nitrile hydrogenation (Scheme 4.151).554... 

Isophorone diamine (IPDA), 10 395 14 588 cis, Irares-Isophoronediamine physical properties of, 2 500t Isophorone dienamine-acrylonitrile reaction, 13 438... 

Isophorone diamine, a cycloaliphatic amine, has been reported to cause skin sensitization. ... 

Lachapelle JM, Lachapelle-Ketelaer MJ Cross-sensitivity between isophorone diamine and isophorone diisocyanate (IPDI). Contact Derm 5 55, 1979... 

Other cycloaliphatic diamines such as isophorone diamine, bis-p-aminocyclohexylmethane and 1,2-diaminocyclohexane are used as epoxy resin curing agents for both ambient and heat cured epoxy resin systems. While they have advantages, such as light color and good chemical resistance, they provide rather sluggish cure rates at low temperatures. 

Fig.16 S-N fatigue diagram of a bulk diglycidyl ether of bisphenol (DGEBA)/isophoron diamine (IPD) epoxy polymer giving the maximum applied stress as a function of the number of cycles to failure (three-point bending, 25 Hz, stress ratio OminMnax = 0.1) (from [53]). The two dotted lines correspond to theoretical values of the amplitude of the effective tensile stress, Acr, calculated for (a) gross slip condition and (b) under partial slip condition for an imposed displacement ( 10 xm) which corresponds to the experimental contact endurance limit at 105 cycles...

SYNS CYCLOHEXANE, 5-ISOCYANATO-l-(ISOCYANATOMETHYL)-l,3,3-TRIMETHYL-(9CI) IPDI 3-ISOCYANATOMETHYL-3,5,5-TRIMETHYLCYCLO-HEXYLISOCYANATE ISOPHORONE DIAMINE DIISOCYANATE ISOPHORONEDIISOCYANATE, solution, 70%, by weight (DOT) TRIISOCYANATO-ISOCYANURATE, solution, 70%, bv weight (DOT)... 

Pichaud et al. (1999) highlight the chemorheology and dielectrics of the cure of DGEBA with isophorone diamine (IPD). The kinetics are well described by an autocatalytic model and the chemorheology is well described by the Macosko model... 

ISOPHORONE DIAMINE (2855-13-2) Incompatible with organic anhydrides, acrylates, alcohols, aldehydes, alkylene oxides, substituted allyls, cellulose nitrate, cresols, caprolactam solution, epichlorohydrin, ethylene dichloride, isocyanates, ketones, glycols, nitrates, phenols, vinyl acetate. Exothermic decomposition with maleic anhydride. Increases the explosive sensitivity of nitromethane. Corrodes aluminum and steel in the presence of moisture. 

ISOPHORONE DIAMINE DIISOCYANATE (4098-71-9) Combustible liquid (flash point 212°F/100°C). Reacts with water, forming cyanic acid. Incompatible with acids, caustics, alcohols, ammonia, aliphatic amines, alkanolamines, aromatic amines, amides, caprolactam, glycols, mercaptans, strong oxidizers. 

CCRIS 6680 Cyclohexanemethanamine, 5-amino-1,3,3-trimethyl- EINECS 220-666-8 HSDB 4058 Isophorone diamine UN2289 Vestamin TMD. Epoxy curative for flexible coatings, adhesives, castings and composites. Degussa-Hiils Corp. 

BRN 2726467 CCRIS 6252 Cyclohexane, 5-isocyanato-1-(isocyanatomethyl)-l,3,3-trimethyl- EINECS 223-861-6 HSDB 6337 IPDi Isophorone diamine diisocyanate Isophorone diisocyanate UN2290 Vestanat IPDI, Raw matenal for mfg. of light stable polyurethanes. Degussa-Huls Corp. 

Sharping, G., Dalene, M., and Tinnerberg, H., Biological monitoring of hexamethylene-diisocyanate and isophorone-diisocyanate by the determination of hexamethylene-diamine and isophorone-diamine in hydrolyzed urine using liquid-chromatography and mass-spectrometry. Analyst, 119, 2051-2055, 1994. 

A new process for synthesis of 3-aminomethyl-3,5,5-trimethylcyclohexylamine (IPDA) has been investigated. The reaction was performed in two steps. In the first step bis (3-cyano-3,5,5 trimethylcyclohexylidene) azine (IPNA) was synthesized from 3-cyano-3,5,5 trimethyl- 1 oxo cyclohexane (IPN) and hydrazine hydrate in solvent. The reaction yield was nearly quantitative. In the second step the azine (IPNA) was hydrogenated under mild conditions on a Raney nickel or cobalt catalyst in the presence of a small amount of ammonia. Isophorone diamine (IPDA) was obtained at high yields (90-95 %). But the main interest of a such process is to minimize the production of byproducts (aminoalcohol, azabicyclic compound, secondary amine) and to use less severe pressure conditions than those generally employed. 

At the present time isophorone diamine (IPDA) is experiencing a good expansion in its traditional markets such as polyurethanes, paints and varnishes. For this reason a real interest has been shown in the synthesis of IPDA. Until now, this compound was synthesized by aminoreduction of isophoronenitrile (IPN). 

Synonyms/Trade Names IPDI 3-lsocyanatomethyl-3,5,5-trimethylcyclohexyl-isocyanate Isophorone diamine diisocyanate ... 

A key step in the large-scale production of isophorone diamine (IPDA, Degussa) is simultaneous hydrogenation of a nitrile group and reductive amination of a keto function from isophoronenitrile (IPN) to give the corresponding diamine using a catalyst based on cobalt, nickel or ruthenium or mixtures thereof (Eq. 8-15) [4] ... 

Aliphatic primary amines. Common examples are diethylene triamine (DETA), tetraethylene pentamine (TEPA), n-aminoethyl piperazine, and isophorone diamine. They give good room-temperature cure at stoichiometric ratios, but have poor HDT, inconvenient mix ratios, high peak exotherm, and are strongly irritant. Isophorone diamine produces very light colored mixes with good color stability. 

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