Amines are key intermediates in the chemical industry due to their nucleophilic characteristic which confers a high reactivity to them. Thus, they are key monomers for the synthesis of polyamides, polyureas, polyepoxydes, which are all of growing interest in automotive, aerospace, building, or health applications. Despite a growing interest for biobased monomers and polymers, and particularly polyamides, it should be noticed that very few natural amines are available. Actually, there is only chitosan and poly(lysine). In this review we present both fundamental and applied research on the synthesis of biobased primary and secondary amines with current available biobased resources. Their use is described as a building block for material chemistry. Hence, we first recall some background on the synthesis of amines, including the reactivity of amines. Second we focus on the synthesis of biobased amines from all sorts of biomass, from carbohydrate, terpenes, or oleochemical sources. Third, because they need opt...

Biobased Amines: From Synthesis to Polymers; Present and Future.

Amines are produced by reacting at elevated temperature a first reactant which is either an alcohol, an aldehyde or a ketone with a second reactant which is either ammonia, a primary or secondary amine or a nitrile in the presence as catalyst of a composition comprising (i) nickel, (ii) ruthenium, and (iii) at least one other transition metal selected from either the second or third row transition metals, for example palladium, rhenium or iridium.

Process for the production of amines

The present invention is directed to novel organometallic complexes as catalysts for the reaction of compounds with isocyanate and hydroxyl functional groups to form urethane and/or polyurethane and the process employing such catalysts More particularly, the present invention is directed to novel complexes of zinc(II) with substituted amidines These novel catalysts are useful for the production of urethanes and polyurethanes which are important in many industrial applications

Organometallic compositions and coating compositions

A PROCESS FOR THE PRODUCTION OF URETDIONE GROUP-CONTAINING COMPOUNDS, THE COMPOUNDS OBTAINED ACCORDING TO THIS PROCESS AND THE USE THEREOF IN THE PRODUCTION OF POLYURETHANE PLASTICS MATERIAL ABSTRACT OF THE DISCLOSURE The invention is directed to a process for the production of uretdione group-containing compounds by dimerizing at least a part of the isocyanate groups of organic isocyanates in the presence of compounds containing phosphorus-nitrogen bonds as dimerization catalysts, characterized in that the reaction is carried out in the presence, as co-catalysts, of H-active organic compounds having a pKa-value of at least 6, which have at least one hydrogen atom bound to oxygen, sulphur or nitrogen. The invention also relates to the uretdione group-containing compounds obtained according to this process and to their use for the production of plastics materials according to the isocyanate-polyaddition process.

Process for the production of uretdione group-containing compounds, the compounds obtained according to this process and the use thereof in the production of polyurethane plastics material

The prodn. of uretedione gp-contg. poly-addn. prods. (I) based on polyisocyanate-uretediones with at least 2 free NCO gps. (II), diols (III) and opt. mono-alcohols or mono-amines is carried out as a continuous process in the absence of solvent. Pref. the reaction is carried out in an intensive kneader, pref. a single or twin screw extruder, esp. pref. a twin screw extruder at up to 190 (pref. up to 180, esp. pref. up to 170) degrees C. The kneader has suitably equipped mixing chambers and a screw geometry designed to produce intensive, rapid mixing, with a highly viscous prod. stream and intensive heat exchange, together with a constant flow along the mixer and the most uniform residence time possible. The reactants and catalyst are fed into the extruder in separate streams, with more than 2 prod. streams, these can be combined, the diols and/or mono-alcohols and/or catalysts can be combined with inert additives as one stream. The inlets for the various streams can be varied in sequence and operated at different times.

Process for the preparation of polyaddition products containing uretdione groups and their use in polyurethane-lacquer systems

OF THE DISCLOSURE A process for the preparation of a uretedione, comprises the steps of: (i)dimerizing at least one C6-15 (cyclo)aliphatic diisocyanate under substantially anhydrous conditions in the presence of a pyridine of the formula wherein R1 and R2 are, independent from one another, a C1-4 alkyl group or R1 and R2 taken together with the attached nitrogen form a pyrrolidine, piperidine or morpholine ring, to form a reaction mixture containing said uretedione, and (ii) isolating said uretedione from said reaction mixture by vacuum thin layer evaporation after the degree of dimerization in said reaction mixture has reached 10-80% By this process, a substantially isocyanurate-free uretedione is produced. The product is useful, for example, in the production of a polyurethane paint.

Process for the preparation of (cyclo)aliphatic uretediones

A process for producing a substantially isocyanurate-free uretidione dimer of isophorone diisocyanate, which is more than 98% decomposable by heat to isophorone diisocyanate, which comprises dimerizing isophorone diisocyanate, optionally in an inert organic solvent, in the presence of a catalyst of the formula X m P(NR 2 ) 3-m wherein m=0, 1, 2; X=Cl OR of R wherein R is selected from the group consisting of the same or different aklyl radical, aralkyl radical, cycloalkyl radical, substituted cycloalkyl radical and radicals wherein two or more of the aforementioned radicals form a hererocyclic ring together with the nitrogen atom; at temperatures of 0°-80° C., isolating the resulting 1,3-diazacyclobutane-2,4-dione, after 5-70% conversion, without previous inactivation of the catalyst, from the reaction mixture as the residue of a thin film distillation and isolating the catalyst and monomer as the distillate.

Uretidione dimer of isophorone diisocyanate and method of preparation

Polyadditionsprodukte aus uretdiongruppenhaltigem Isophorondiisocyanat, das in der Hitze zu 98 % in Isophorondiisocyanat ruckspaltbar ist, und Diolen und gegebenenfalls Monoalkoholen und Monoaminen. Ein Verfahren zur Herstellung dieser Polyadditionsprodukte, wobei man das uretdiongruppenhaltige Isophorondiisocyanat mit Diolen in einem NCO/OH-Verhaitnis von 1 : 0,5 bis 1 : 0,9 bzw. 0,5 : 1 bis 0,9 : 1 versetzt und das erhaltene Polyadditionsprodukt gegebenenfalls ganz oder teilweise mit Monoalkoholen bzw. Monoaminen zur Reaktion bringt. Als Diole sind insbesondere Ethylenglykol, Butandiol-(1,4), Hexandiol-(1,6), Diethylenglykol und 3-Methylpentadiol-(1,5) geeignet. Als Monoalkohole kommen insbesondere Methanol, Ethanol, 2-Ethylhexanol, Butanol und Cyclohexanol in Betracht. Die Reaktionskomponenten konnen in Losung umgesetzt werden.

Verfahren zur Herstellung von uretdiongruppenhaltigen Polyadditionsprodukten sowie die danach hergestellten Produkte

In a process for the trimerization of diisocyanates in the presence of a catalyst comprising quaternary ammonium salts of organic acids having the formula: ##STR1## wherein X represents the same or different radicals selected from the group consisting of C 1 -C 20 alkyl, C 3 -C 8 cycloalkyl, and C 2 -C 20 aralkyl; two X radicals taken together with at least one other heteroatom forming a hetero-ring and three X radicals taken together with the quaternary nitrogen atoms forming a hetero-ring through a common hetero-atom such that said heterocyclic ring structure is selected from the group consisting of triethylene diamine, methyl triethylene diamine, quinuclidine, N-methylmorpholine, N-ethylmorpholine, and N,N'-dimethylpiperazine; R is alkyl, cycloalkyl or aralkyl, R" is R or hydrogen; R+R" together form a C 1 -C 12 alkyl radical; R' is hydrogen, hydroxyl or a C 1 -C 12 alkyl radical, optionally containing a CH.sub.(3-b) Z b group, wherein b=1 to 3 and Z is OH, the improvement comprising: reacting said diisocyanate with said catalyst in an amount of 0.02 to 0.1% by weight calculated on the weight of the compound to be trimerized at a temperature ranging from 40° to 120° C.

Process for the trimerization of diisocyanates

Primare Amine und/oder Diamine aus Oxoverbindungen, Ammoniak und Wasserstoff lassen sich mit hoherer Ausbeute als nach den bekannten Verfahren herstellen, wenn man die Oxoverbindungen vor der hydrierenden Amminierung einer Vorreaktion mit Ammoniak in Gegenwart von Iminbildungskatalysatoren unterwirft. Primary amines and / or diamines from oxo compounds, ammonia and hydrogen can be produced at a higher yield than by the known methods when subjecting the oxo compounds before hydrogenating Amminierung a preliminary reaction with ammonia in the presence of Iminbildungskatalysatoren. Dazu werden vorzugsweise mit Ammonium beladene anorganische oder organische Ionenaustauscher und/oder im Reaktionsgemisch unlosliche Ammoniumsalze, gegebenenfalls auf Tragerstoffen, verwendet. These preferably are loaded with inorganic or organic ammonium ion exchanger and / or in the reaction mixture insoluble ammonium salts, optionally used on carriers.

Werner Dr. Hübel

Papers

Process for the preparation of (cyclo)aliphatic uretediones

Uretidione dimer of isophorone diisocyanate and method of preparation

Verfahren zur Herstellung von uretdiongruppenhaltigen Polyadditionsprodukten sowie die danach hergestellten Produkte

Process for the trimerization of diisocyanates

Process for the preparation of primary mono- and diamines from oxo-compounds