Trimerization Process To Form The Triazine Ring Patents (Class 544/193)
-
Patent number: 4487928Abstract: The present invention thus relates to a process for the preparation of polyisocyanates having isocyanurate groups by the trimerization of part of the isocyanate groups of organic polyisocyanates or of mixtures of di- and mono-isocyanates in the presence of basic compounds as trimerization catalysts, with termination of the trimerization reaction by the addition of a catalyst poison, characterized in that the trimerization catalysts used are 1:1-complexes of (i) basic sodium or potassium compounds and (ii) 1,4,7,10,13-pentaoxacylopentadecane or 1,4,7,10,13,16-hexaoxacyclooctadecane.This invention also relates to solutions suitable as catalyst components for this process, comprising 1:1-complexes of (i) basic sodium or potassium compounds and (ii) 1,4,7,10,13-pentaoxacyclopentadecane or 1,4,7,10,13,16-hexaoxacyclooctadecane dissolved in polar lacquer solvents and/or at least one compound within the molecular weight range of about 32 to 250 which has alcoholic hydroxyl groups and is liquid at room temperature.Type: GrantFiled: December 23, 1981Date of Patent: December 11, 1984Assignee: Bayer AktiengesellschaftInventors: Roland Richter, Hanns P. M/u/ ller, Kuno Wagner
-
Patent number: 4454317Abstract: 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.Type: GrantFiled: July 23, 1982Date of Patent: June 12, 1984Assignee: Chemische Werke Huls AktiengesellschaftInventors: Josef Disteldorf, Werner Hubel, Elmar Wolf
-
Patent number: 4454296Abstract: The present invention provides novel triisocyanate compounds of the formula: ##STR1## wherein ##STR2## stands for ##STR3## the production thereof and the use thereof for polyurethane resins, especially, for solvent-free or high solids polyurethane coatings.Type: GrantFiled: April 22, 1982Date of Patent: June 12, 1984Assignee: Takeda Chemical Industries, Ltd.Inventors: Kimiya Fujinami, Ichiro Minato, Koichi Shibata
-
Patent number: 4426460Abstract: Improved rigid urethane and isocyanurate foam compositions having improved fire resistance are described. The urethane foams are based on furan compositions having the formula: ##STR1## and from about 100% to about 500% of a stoichiometric amount of a reactive polyisocyanate to produce a foamable composition, and sufficient blowing agent to create a foam having a density from about 1.5 to about 5 pounds per cubic foot. The product has improved fire resistence. The disclosure also described the method of decreasing the flame hazard potential of a rigid foam by adding two urethane or isocyanurate foaming ingredients the appropriate amount of one or more of the compositions listed above. The polymers described are chiefly made from adding propelyne oxide to bis (hydroxymethyl) furan.Type: GrantFiled: August 10, 1981Date of Patent: January 17, 1984Assignee: Quaker Oats CompanyInventor: William J. Pentz
-
Patent number: 4413123Abstract: 1,3,5-triacrylylhexahydro-s-triazine is prepared as a solution in excess of about 10 weight percent and in yields of up to about 99 percent of theoretical by reacting acrylonitrile and trioxane with a catalytic amount of an acid having a Hammet activity function (H.sub.o) in excess of about 7.3 utilizing methylene chloride as the reaction medium.Type: GrantFiled: March 29, 1982Date of Patent: November 1, 1983Assignee: Union Carbide CorporationInventors: Louis B. Conte, Jr., Walter T. Reichle
-
Patent number: 4412073Abstract: Monomeric or polymeric isocyanurates, e.g., polyisocyanate/polyisocyanurates, are prepared by catalytically cyclotrimerizing an isocyanate, e.g., an aliphatic or cycloaliphatic isocyanate, in the presence of an aminosilyl catalysis initiator, e.g., a mono- or diaminosilane, a silylurea or a silazane, having the structural formula:R.sub.(4-n) Si--NR'R"].sub.n (I)wherein R is a saturated or unsaturated, aliphatic, cycloaliphatic, aryl, aralkyl or alkylaryl monovalent hydrocarbon radical, or halo or cyano substituted such radical, and further wherein any two radicals R may together form a single divalent such hydrocarbon radical; R' is R, SiR.sub.3 or an amido radical having the structural formula: ##STR1## wherein R'" is R or SiR.sub.3, with R being as above defined, and further wherein R', when R' is neither the amido radical nor SiR.sub.Type: GrantFiled: February 1, 1982Date of Patent: October 25, 1983Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Jean Robin
-
Patent number: 4382125Abstract: A stable isocyanurate-modified polyisocyanate prepared by trimerizing an organic polyisocyanate mixture of 45 to 70 percent by weight of diphenylmethane diisocyanate having an isomer mixture of 40 to 100 weight percent, 4,4'-, 0 to 50 weight percent 2,4-, and 0 to 10 weight percent 2,2'-diphenylmethane diisocyanate and from 30 to 55 percent by weight polymethylene polyphenylene polyisocyanate with an isocyanurate content of 20 to 33 percent by weight. Polyurethane isocyanurate foams prepared from the reaction of these isocyanates with active hydrogen compounds selected from the group consisting of diethylene glycol and ethylene oxide adducts of trimethylolpropane, trimethylolethane, and glycerine exhibit good K- factors, low friability and low smoke density.Type: GrantFiled: November 30, 1981Date of Patent: May 3, 1983Assignee: BASF Wyandotte CorporationInventors: Thirumurti Narayan, Peter T. Kan, John T. Patton, Jr.
-
Patent number: 4379905Abstract: The subject of the invention is a process for the preparation of polyisocyanates containing isocyanurate groups which comprises trimerizing a proportion of the isocyanate groups of organic polyisocyanates or mixtures of di- and monoisocyanates in the presence of basic alkali metal compounds as catalysts and terminating the trimerization reaction by the addition of a catalyst poison, characterized in that the trimerization catalysts are complexes of(i) basic alkalimetal compounds and(ii) acyclic organic compounds which(a) have at least 6 alkylene oxide units of the formula --R--O--, wherein R represents C.sub.1 -C.sub.Type: GrantFiled: January 6, 1982Date of Patent: April 12, 1983Assignee: Bayer AktiengesellschaftInventors: Ingo Stemmler, Hanns P. Muller, Kuno Wagner
-
Patent number: 4359550Abstract: Polyisocyanurate polymers are prepared by the polymerization of organic polyisocyanates in organic solvents employing trimerization catalysts. After deactivation of the catalysts and removal of the solvents, these polymers may be dispersed in polyols which are employed for the preparation of cellular and non-cellular polyurethane products displaying improved load bearing properties.Type: GrantFiled: January 19, 1981Date of Patent: November 16, 1982Assignee: BASF Wyandotte CorporationInventors: Thirumurti Narayan, Gerhard G. Ramlow, Peter T. Kan
-
Patent number: 4359541Abstract: Polyisocyanurate polymers are prepared by polymerization of polyisocyanates in organic solvents employing trimerization catalysts. The polyisocyanates are reacted with monofunctional active hydrogen compounds prior to polymerization or subsequent to the polymerization. These polymers may be dispersed in polyols for the preparation of cellular and non-cellular polyurethane products having improved physical properties.Type: GrantFiled: January 19, 1981Date of Patent: November 16, 1982Assignee: BASF Wyandotte CorporationInventors: John T. Patton, Jr., Thirumurti Narayan, Gerhard G. Ramlow
-
Patent number: 4335219Abstract: The reaction of an isocyanate such as toluene diisocyanate with itself to form an isocyanurate or with an active hydrogen compound such as diethylene glycol to form a urethane is catalyzed by the presence of an ar-ammonium areneoxide such as 4-dodecyl-2-trimethylammonium phenoxide.Type: GrantFiled: April 6, 1981Date of Patent: June 15, 1982Assignee: The Dow Chemical CompanyInventors: Donald H. Clarke, George J. Pomranky, Donald L. Schmidt
-
Patent number: 4326043Abstract: Polyisocyanurate polymers are prepared by polymerization of polyisocyanates in organic solvents employing trimerization catalysts. The polyisocyanates are reacted with halogenated alcohols subsequent to polymerization. These polymers may be dispersed in polyols for the preparation of cellular and non-cellular polyurethane products having improved flame retardant physical properties.Type: GrantFiled: January 19, 1981Date of Patent: April 20, 1982Assignee: BASF Wyandotte CorporationInventors: Thirumurti Narayan, John T. Patton, Jr.
-
Patent number: 4324879Abstract: The present invention is concerned with an improved process for the production of partially trimerized hexamethylene diisocyanate which yields isocyanurate isocyanates which have low viscosity and low monomer contents by the use of a quaternary ammonium hydroxide catalyst which is hydroxyalkyl substituted at its N atom.Type: GrantFiled: May 19, 1980Date of Patent: April 13, 1982Assignee: Bayer AktiengesellschaftInventors: Manfred Bock, Josef Pedain, Walter Uerdingen
-
Patent number: 4306051Abstract: A method for the production of blocked isocyanate- and isocyanurate group-containing compounds which comprises reacting a monomeric cycloaliphatic polyisocyanate to form an intermediate mixture comprising an isocyanurate containing at least two free isocyanate groups; and blocking the intermediate isocyanurate mixture with dimethylketoxime at 50.degree.-120.degree. C., wherein the amount of said dimethylketoxime is such that one equivalent of NCO group reacts with one equivalent of the dimethylketoxime. A mixture containing isocyanurate and blocked isocyanate groups which comprises at least 10% by weight of a cycloaliphatic isocyanurate containing at least two isocyanate groups blocked with dimethylketoxime and a monomeric polyisocyanate blocked with dimethylketoxime in such amounts as necessary to complete 100% by weight of the mixture, and wherein the unblocked NCO-group content of the monomeric polyisocyanate is less than 0.5% by weight.Type: GrantFiled: March 28, 1980Date of Patent: December 15, 1981Assignee: Chemische Werke Huls AGInventors: Rainer Gras, Elmar Wolf
-
Patent number: 4293680Abstract: The instant invention is directed to a process for the production of diisocyanate mixtures of 2,4-diisocyanato toluene and 2,6-diisocyanato toluene, having from 36 to 90% by weight, based on the total mixture, of 2,6-diisocyanato toluene, comprising: trimerizing some of the isocyanate groups of a diisocyanate mixture of 2,4-diisocyanato toluene and 2,6-diisocyanato toluene, having a maximum content of 2,6-diisocyanato toluene of 35% by weight based on the total mixture and isolating from the reaction mixture which is thus obtained, a diisocyanate mixture having an increased content of 2,6-diisocyanato toluene.The invention is also directed to the use of these mixtures as synthesis components in the production of polyurethane elastomers.Type: GrantFiled: August 6, 1980Date of Patent: October 6, 1981Assignee: Bayer AktiengesellschaftInventors: Jan Mazanek, Hanns P. Nuller
-
Patent number: 4291161Abstract: The compound of N,N',N"-trimethyl trithioisocyanurate and the novel compound N,N',N"-trimethyl 2-iminodithioisocyanurate have been found to be effective in protecting rice against Pyricylaria oryzae.Type: GrantFiled: February 25, 1980Date of Patent: September 22, 1981Assignee: Dupaar International Research B.V.Inventors: Hendrik Dolman, Johannes Kuipers
-
Patent number: 4283535Abstract: 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.Type: GrantFiled: May 14, 1979Date of Patent: August 11, 1981Assignee: Chemische Werke Huls AGInventors: Josef Disteldorf, Werner Hubel, Elmar Wolf
-
Patent number: 4282356Abstract: A compound, with hypoglycaemic activity, having formula (II) or a pharmaceutically acceptable quaternary ammonium or acid addition salt thereof: ##STR1## wherein X represents oxygen or sulphur;n represents zero or 1;R.sup.7 represents hydrogen or C.sub.1-6 alkyl;R.sup.1 and R.sup.2 are the same or different and represent hydrogen, C.sub.1-6 alkyl, phenyl, benzyl, or C.sub.3-6 cycloalkyl;R.sup.3 represents hydrogen, C.sub.1-6 alkyl, phenyl or benzyl;R.sup.4 represents hydrogen or C.sub.1-6 alkyl;R.sup.5 represents C.sub.1-6 alkyl, phenyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl, and C.sub.1-6 alkoxy; or benzyl optionally substituted with up to 3 groups selected from halogen, C.sub.1-6 alkyl and C.sub.1-6 alkoxy; or R.sup.4 and R.sup.5 together represent the remaining members of a 5- or 6-membered ring optionally containing an oxygen, sulphur or additional nitrogen atom and being optionally substituted with C.sub.1-6 alkyl, carboxy or C.sub.1-6 alkoxycarbonyl; andR.sup.Type: GrantFiled: June 10, 1980Date of Patent: August 4, 1981Assignee: Beecham Group LimitedInventor: Barrie C. C. Cantello
-
Patent number: 4265798Abstract: Potassium salt of 2-pyrrolidinone is used as a catalyst to cyclotrimerize an organic diisocyanate, yielding a mixture of monomeric cyclotrimerized product (isocyanurate) and oligomers thereof, soluble in common organic solvents and vinyl monomers. The catalyst can be used to make one-shot isocyanurate-crosslinked polyurethanes. Prepolymers and moisture-curing coating compositions can also be prepared.Type: GrantFiled: February 11, 1980Date of Patent: May 5, 1981Assignee: Uniroyal Ltd.Inventor: Anupama Mishra
-
Patent number: 4264498Abstract: A process for preparing an azetidinone of the formula: ##STR1## which comprises reacting a C-unsubstituted methyleneamine of the formula: ##STR2## with R.sup.2 --CH.sub.2 COOH, its acid halide or anhydride, in the presence of boron trihalide and an organic base, wherein R.sup.1 is an organic residue bearing a carboxy group or its derivative and R.sup.2 is azido, substituted amino, halogen, acyloxy, alkoxy, aryloxy or aralkoxy.Type: GrantFiled: February 21, 1979Date of Patent: April 28, 1981Assignee: Fujisawa Pharmaceutical Co., Ltd.Inventors: Takashi Kamiya, Masashi Hashimoto, Osamu Nakaguti, Teruo Oku, Yoshiharu Nakai, Hidekazu Takeno
-
Patent number: 4255569Abstract: The instant invention is directed to a process for the production of isocyanate polyisocyanates containing at least 50%, by weight, of tris-isocyanatomonoisocyanurates and at most 3%, by weight, of isocyanurate-free diisocyanate. The process comprises catalytically trimerizing the organic diisocyanates free from isocyanurate groups and terminating the trimerization reaction by deactivation of the catalyst after 5 to 40% of the isocyanate groups of the isocyanurate-free diisocyanate have been trimerized. The unreacted isocyanurate-free diisocyanate is then distilled off in the presence of from 1 to 30%, by weight, based on the end product obtained as distillation residue, of an inert liquid distillation aid which boils at a temperature at least 50.degree. C. above the boiling point of the isocyanurate-free diisocyanate.The invention is also directed to the products produced by this process.Type: GrantFiled: May 4, 1979Date of Patent: March 10, 1981Assignee: Bayer AktiengesellschaftInventors: Hans-Jurgen Muller, Rudolf Hombach, Manfred Dollhausen, Joachim Zirner
-
Patent number: 4255453Abstract: A process for the production of isocyanates by the addition of carbon monoxide to a metal or aryl carbamate.Type: GrantFiled: August 16, 1977Date of Patent: March 10, 1981Inventor: Robert K. Jordan
-
Patent number: 4246132Abstract: A method for the production of blocked isocyanate-and isocyanurate group-containing compounds which comprises:transforming a monomeric aliphatic or cycloaliphatic polyisocyanate or a mixture thereof into an intermediate mixture comprising an isocyanurate containing at least 2 free isocyanate groups; andblocking said intermediate isocyanurate mixture with dimethylketoxime at 50.degree.-120.degree. C.;wherein the amount of said dimethylketoxime is such that one equivalent of NCO group reacts with one equivalent of said dimethylketoxime.The mixtures of the present invention are particularly suited as co-catalysts for the anionic polymerization of epsilon-caprolactam, as well as hardeners for higher functional thermoplastic compounds which contain Zerewitinoff-active hydrogen atoms.Type: GrantFiled: July 20, 1978Date of Patent: January 20, 1981Assignee: Chemische Werke Huls AGInventors: Rainer Gras, Elmar Wolf
-
Patent number: 4216316Abstract: A process is disclosed for the preparation of alkyl cyanates, alkyl isocyanurates, multifunctional alkyl cyanates, and oligomers of multifunctional alkyl isocyanates by reacting cyanogen halide with the corresponding thallium(I) salt of an alkanol at reduced temperatures, optionally in the presence of an inert solvent. Subsequently, warming the resulting product to ambient temperature causes isomerization to the corresponding aliphatic isocyanate and ultimately oligomerization to form trialkyl isocyanurate or oligomers of multifunctional alkyl isocyanates.Type: GrantFiled: February 8, 1979Date of Patent: August 5, 1980Assignee: The Dow Chemical CompanyInventor: Edward E. Flagg
-
Patent number: 4182887Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is mono- or di-substituted amino, where the substituents are selected from the group consisting of alkyl of 1 to 6 carbon atoms, cyclohexyl, allyl and benzyl; unsubstituted, mono-substituted or di-substituted pyrrolidino, piperidino, hexamethyleneimino, morpholino, piperazino, thiomorpholino, 1-oxido-thiomorpholino or 1,1-dioxido-thiomorpholino, where the substituents are selected from the group consisting of methyl, hydroxymethyl, hydroxyl, phenyl and benzyl; 1,2,5,6-tetrahydropyridino; 1,2,3,4-tetrahydroisoquinolino; indolino; or 3,6-ethylene-hexamethyleneimino;R.sub.2 is hydrogen, methyl or benzyl; andR.sub.3 is hydrogen, halogen, alkyl of 1 to 3 carbon atoms or alkoxy of 1 to 3 carbon atoms;and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as antiphlogistics and antithrombotics.Type: GrantFiled: September 19, 1977Date of Patent: January 8, 1980Assignee: Boehringer Ingelheim GmbHInventors: Josef Roch, Erich Muller, Berthold Narr, Josef Nickl, Walter Haarmann
-
Patent number: 4159262Abstract: Triazine compounds and cross-linked polymer compositions are made by heating aromatic nitriles to a temperature in the range of from about 100.degree. C. to about 700.degree. C., and preferably in the range of from about 200.degree. C. to about 350.degree. C. in the presence of a catalyst or mixture of catalysts selected from one or more of the following groups: (A) organic sulfonic and sulfinic acids, (B) organic phosphonic and phosphinic acids, and (C) metallic acetylacetonates, at a pressure in the range of from about atmospheric pressure to about 10,000 p.s.i., and preferably in the range of from about 200 p.s.i. to about 750 p.s.i.Type: GrantFiled: May 12, 1977Date of Patent: June 26, 1979Assignee: The United States of America as represented by the Administrator, National Aeronautics and Space AdministrationInventor: Li-Chen Hsu
-
Patent number: 4145544Abstract: Disclosed is a process for the preparation of ethylenically unsaturated isocyanurates which comprises a first step of trimerizing an aromatic polyisocyanate in the presence of an isocyanate trimerization catalyst and an ethylenically unsaturated solvent wherein at least 20% by weight of the solvent is an ethylenically unsaturated polar solvent, to form an isocyanate-containing isocyanurate and a second step of reacting the isocyanate-containing isocyanurate with a monohydric alcohol containing a vinylidene group to form an ethylenically unsaturated isocyanurate. The resulting solution of an ethylenically unsaturated isocyanurate dissolved in an ethylenically unsaturated solvent may be cured to form resins having excellent high temperature resistant properties.Type: GrantFiled: July 27, 1977Date of Patent: March 20, 1979Assignee: ICI Americas Inc.Inventor: Erich Kuehn
-
Patent number: 4124545Abstract: Novel compounds which upon heating are converted into the corresponding phenol which is a catalyst for the trimerization of compounds having isocyanato groups to form isocyanurates have the formula: ##STR1## in which N REPRESENTS AN INTEGER OF FROM 1 TO 4A represents an aromatic hydrocarbon group obtained by removing the NCO group from a monomeric aromatic monoisocyanate containing 6 - 14 carbon atoms,R.sub.1 and R.sub.2 may be the same or different and represent a C.sub.1 to C.sub.6 alkyl group or a polymethylene chain containing 4 to 8 carbon atoms which together with the nitrogen atom form a heterocyclic ring,R.sub.3 may be hydrogen, chlorine, bromine or a C.sub.1 - C.sub.18 -alkyl group.Type: GrantFiled: June 22, 1977Date of Patent: November 7, 1978Assignee: Bayer AktiengesellschaftInventors: Jurgen Hocker, Hans-Joachim Diehr, Rudolf Merten
-
Patent number: 4113945Abstract: A novel catalyst system is described that is useful in the trimerization of organic isocyanates. The system comprises (1) N,N',N"-trisdialkylaminoalkyl-s-hexahydrotriazine and (2) a compound selected from the group consisting of 3,5-bis(N,N-dialkylaminoalkyl)-1,3,5-tetrahydrooxadiazine, 5-(N,N-dialkylaminoalkyl)-1,3,5-dihydrodioxazine and the mixtures thereof.Type: GrantFiled: July 1, 1977Date of Patent: September 12, 1978Assignee: Armstrong Cork CompanyInventor: William J. Kauffman
-
Patent number: 4076494Abstract: Disclosed is a preparation, for use in the production of inks for transfer printing, which preparation comprises, in intimate admixture, a disperse dye and/or dispersion optical brightener, sublimable in the range of from 180.degree. to 220.degree. C, and a dispersing aid being a compound of formula I, ##STR1## in which R.sub.1, R.sub.2 and R.sub.3, independently, are straight or branched chain C.sub.2-8 alkylene radicals, the OH groups being bound other than onto the carbon atoms adjacent the nitrogen atoms,The production and use thereof.Type: GrantFiled: November 3, 1976Date of Patent: February 28, 1978Assignee: Sandoz Ltd.Inventors: Johann Schuster, Karl Taubert
-
Patent number: 4061856Abstract: Triazine compounds and cross-linked polymer compositions are made by heating aromatic nitriles to a temperature in the range of from about 100.degree.0 C. to about 700.degree. C., and preferably in the range of from about 200.degree. C. to about 350.degree. C. in the presence of a catalyst or mixture of catalysts selected from one or more of the following groups: (A) organic sulfonic and sulfinic acids, (B) organic phosphonic and phosphinic acids, and (C) metallic acetylacetonates, at a pressure in the range of from about atmospheric pressure to about 10,000 p.s.i., and preferably in the range of from about 200 p.s.i. to about 750 p.s.i.Type: GrantFiled: October 10, 1974Date of Patent: December 6, 1977Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventor: Li-Chen Hsu
-
Patent number: 4059610Abstract: Isocyanic acid derivatives are prepared by reacting an organic halogen compound with an alkali cyanate in N,N-disubstituted organic acid amides, N,N-disubstituted sulfonic acid amides, sulfoxides, sulfones or macrocyclic polyethers, at 70.degree. to 200.degree. C, in the presence of organic polyhalogen compounds selected from compounds having dihalogenomethyl group, dihalogenomethylene group, or trihalogenomethyl group and tetrahalogenomethane, in an amount in the range of from 1 to 20 weight percent based on the weight of said organic halogen compounds.Type: GrantFiled: May 14, 1976Date of Patent: November 22, 1977Assignee: Kao Soap Co., Ltd.Inventors: Susumu Handa, Yoshiaki Tanaka, Atsushi Nishibata, Sadashi Ueda, Yoshiaki Inamoto, Masahiro Saito, Fumio Tanimoto, Hisao Kitano