Chemische Werke Huls Aktiengesellschaft

Chemische Werke Huels Aktiengesellschaft

Veba-chemie Aktiengesellschaft

Chemische Werke

Werner Hubel

Josef Disteldorf

Elmar Wolf

Horst Schnurbusch

Rainer Gras

Werner Flakus

Manfred Zur Hausen

Karl Schmitt

Gunter Kriebel

Gunter Hasser

Werner Nagengast

Johannes Reiffer

Isocyanate-uretdiones having the formula: ##STR1## wherein the R groups are identical or different and are hydrocarbon groups having the formulas: ##STR2## and n is an integral or fractional number from 1 to 5. Production of the isocyanate-uretdiones, which can be dissociated by heat up to an extent of greater than 70%, is accomplished through dimerization of aliphatic diisocyanates having the formula: ##STR3## with a phosphine catalyst having the formula:

Isocyanate-uretdiones and a method for their production

This invention relates to a process for the production of organic isocyanates by the continous hot phosgenation of amines, whereby the solids are retained in the reactor by an appropriate separator and the isocyanate formed during the reaction is constantly removed from the reactor. Preferably the amount of solids of the suspension in the reactor is set so that the amount of the isocyanate taken off per unit of time reaches a maximum.

Process for continuous hot phosgenation of amines

A process for producing polyalkylpiperidylamines of the formula (I): ##STR1## wherein R.sub.1 is hydrogen or a C.sub.1 -C.sub.12 alkylradical; R.sub.2 and R.sub.3 are each C.sub.1 -C.sub.5 alkylradicals or R.sub.2 and R.sub.3, taken together, are --(CH)--.sub.a or --CH.sub.2 --NR.sub.1 --C(R.sub.5,R.sub.6)--CH.sub.2 --; R.sub.4 is a C.sub.2 -C.sub.18 alkylene radical, which is unsubstituted or substituted by C.sub.1 -C.sub.3 alkyl; a C.sub.5 -C.sub.12 cycloalkylene radical, which is unsubstituted or is methyl-substituted; a cycloalkylene radical of the formula ##STR2## where the cyclohexyl rings are unsubstituted or are methyl-substituted; or groups of the formula --(CH.sub.2).sub.k --X--[CH.sub.2).sub.m --X]--.sub.n (CH.sub.2).sub.p --, where X is --O--, --NH--, --NR.sub.5 and R.sub.5 and R.sub.6 are each a C.sub.1 -C.sub.5 alkyl radical and a is 4 or 5, k is 2 or 3, n is 0-3 and p is 2 or 3; which process involves reductively alkylating an alkylated 4-aminopiperidine of the formula (II): ##STR3## with a difunctional alcohol of the formula HO--R.sub.4 --OH, wherein R.sub.1 and R.sub.4 have the above definitions.

Process for the production of polyalkylpiperidylamines

A method for producing a polyaddition product of isophorone diisocyanate and diols which comprises, reacting a uretidione group-containing dimer of isophoronediisocyanate, which is decomposable by heat into 98% isophorone diisocyanate, with a diol, wherein the ratio of NCO to OH groups is such that the final polyaddition product has free terminal NCO groups, or free terminal OH groups.

Polyaddition products containing uretidione groups and process for their

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.sub.m P(NR.sub.2).sub.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.degree.-80.degree. 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

Polyisocyanatoisocyanurates of the formula ##STR1## wherein the R groups may be the same or different and are aliphatic divalent radicals selected from the group consisting of divalent aliphatic radicals having the formulas ##STR2## and n is a whole or fractional number from 1 to 5, are useful as isocyanate hardeners in polyurethane resin coatings.

Isocyanatoisocyanurates

A polyurethane powder enamel free of volatile cleavage products comprising an adduct of the uretidinedione dimer of isophorone diisocyanate with a diol, wherein the adduct has the formula ##STR1## wherein R= ##STR2## X=NCO or ##STR3## R'=a divalent aliphatic, cycloaliphatic, aromatic or araliphatic hydrocarbon radical or a diol, n&gt;1, and

Polyurethane powder enamels free of cleavage products as well as enamel

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.sub.1 -C.sub.20 alkyl, C.sub.3 -C.sub.8 cycloalkyl, and C.sub.2 -C.sub.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.sub.1 -C.sub.12 alkyl radical; R' is hydrogen, hydroxyl or a C.sub.1 -C.sub.12 alkyl radical, optionally containing a CH.sub.(3-b) Z.sub.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.degree. to 120.degree. C.

Process for the trimerization of diisocyanates

A stoving enamel comprising (a) 30-70% by weight of a mixture of a polymer containing hydroxyl groups having a hydroxyl number between 40 and 240 mg KOH/g with an isocyanurate-free derivative of isophorone diisocyanate containing uretidinedione groups and blocked isocyanate groups, (b) 0-3% by weight of a cross-linking catalyst, (c) 30-60% by weight of an organic solvent, (d) 0-65% by weight of a filler or pigment, (e) 0-5% by weight of a dye, and (f) optionally 0.1-3% by weight of leveling agents, gloss improvers, antioxidants, and/or stabilizers, has improved storage stability, reduced curing time and reduced liberation of blocking agent during cure.

Stoving enamel containing blocked isocyanates

A method of preparing 2,4,6-triketohexahydrotriazines which comprises catalytically trimerizing an organic isocyanate at 60.degree.-150.degree. C. in an inert, polar solvent present in an amount of 5-40 weight % with respect to the quantity of said isocyanate, in the presence of 0.1-5 weight % of a catalyst of the formula ##STR1## or hydrated derivatives of said catalyst, wherein R is selected from the group consisting of hydrogen and C.sub.1 -C.sub.4 alkyl, and Me.sup.+2 is a bivalent metal cation; interrupting the trimerization at a conversion of about 50% by cooling; and then isolating the 2,4,6-triketohexahydrotriazine.

Method for the production of 2,4,6-triketohexahydrotriazines

A method for the preparation of high-melting resins which comprises polymerizing a butadiene-rich C.sub.4 -cut of C.sub.4 -olefins with a liquified protonated Friedel-Crafts catalyst of the formula

Method for the preparation of high melting C.sub.4 -hydrocarbon resins

Methyl isobutyl ketone is produced in a one-step process by contacting acetone and hydrogen at a temperature of from about 50.degree.-200.degree.C and a pressure between 50-100 atm, preferably 60-100 atm, in the presence of a catalyst composed of a cation exchange resin having from 0.001 to 0.1 weight percent of a noble metal distributed in monoatomic form therein.

Growing community of inventors

Herne, Germany

Werner Hubel