Carbodiimides (i.e., Hn=c=nh, Wherein Substitution May Be Made For Hydrogen Only) Patents (Class 564/252)
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Patent number: 5650476Abstract: A process for producing a polycarbodiimide resin powder, which includes reacting an organic diisocyanate in the presence of a carbodiimidization catalyst in a solvent to produce a polycarbodiimide resin and obtaining the resin in a powder form, where the organic diisocyanate is represented by the following formula ##STR1## where R.sub.1 is a lower alkyl group or a lower alkoxyl group, or ##STR2## where R.sub.2 and R.sub.3 are independently a hydrogen atom, a lower alkyl group or a lower alkoxyl group, and X is an oxygen atom or a methylene group, or ##STR3## where R.sub.4 and R.sub.5 are independently a hydrogen atom, a lower alkyl group or a lower alkoxyl group; the solvent is a mixed solvent of a good solvent to polycarbodiimide resin and a poor solvent to the resin, having a precipitation number of 30-80; and when the reaction has reached a certain stage, the reaction system is cooled to make the system a slurry of a polycarbodiimide, and then the polycarbodiimide is obtained in a powder form.Type: GrantFiled: October 11, 1995Date of Patent: July 22, 1997Assignee: Nisshinbo Industries, Inc.Inventors: Satoshi Amano, Tomoki Nakamura, Takahiko Ito, Hideshi Tomita, Norimasa Nakamura
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Patent number: 5648537Abstract: The invention relates to a new process for the synthesis of a disubstituted carbodiimide, including a first stage of phosgenation of an N,N'-disubstituted urea in an organic solvent medium.After this first stage ammonia is added to the reaction mixture without preliminary isolation of any intermediate compound.The process is simple, relatively inexpensive and the yield is high.Disubstituted carbodiimides are organic synthesis intermediates used especially in pharmaceutical chemistry as coupling agents in peptide synthesis.Type: GrantFiled: January 16, 1996Date of Patent: July 15, 1997Assignee: Societe Nationale des Poudres et ExplosifsInventors: Patricia Hussenet, Philippe Le Goff, Gerard Sennyey
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Patent number: 5637769Abstract: The present invention provides: a urea-modified carbodiimide represented by the following general formula ##STR1## (wherein each R is a C.sub.1 -C.sub.12 alkyl group or a C.sub.3 -C.sub.10 cycloalkyl group; each Z is a C.sub.1 -C.sub.12 alkylene group, a C.sub.3 -C.sub.10 cycloalkylene group, a C.sub.4 -C.sub.16 alkylene group having a cyclic or non-cyclic structure, or a C.sub.8 -C.sub.16 alkylene group having an aromatic ring; n is an integer of 1-50; and each m is an integer of 1 or 2), and a process for producing the above urea-modified carbodiimide, which comprises (1) reacting an organic aliphatic diisocyanate represented by the following general formulaO.dbd.C.dbd.N--Z--N.dbd.C.dbd.Type: GrantFiled: June 27, 1995Date of Patent: June 10, 1997Assignee: Nisshinbo Industries, Inc.Inventors: Yasuo Imashiro, Ikuo Takahashi, Naofumi Horie, Takeshi Yamane
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Patent number: 5623085Abstract: A method for reducing the amount of microfoam in a spray-applied clear waterborne composition is provided, the clear waterborne composition including an emulsion-polymerized addition polymer bearing at least one first reactive group and a reactive modifier bearing one second reactive group and a water-soluble group, the second reactive group being reactive with the first reactive group; applying the composition to a substrate using a spray method; and drying the composition. A reduced amount of microfoam improves the clarity of a film of the composition. Also provided are monofunctional carbodiimide reactive modifiers and substrates bearing the spray-applied clear compositions.Type: GrantFiled: June 6, 1995Date of Patent: April 22, 1997Assignee: Rohm and Haas CompanyInventors: Matthew S. Gebhard, Linda S. Smith, James C. Day
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Patent number: 5621138Abstract: 4,4'-disubstituted bis-(2,6-diisopropylphenyl)carbodiimides of the formula (I) ##STR1## where R is 1-methyl-1-phenylethyl, phenoxy or tert-butyl, a process for their preparation, their use as stabilizers against hydrolytic degradation of polyaddition and polycondensation products containing ester groups, and the novel 4-(1-methyl-1-phenylethyl)-2,6-diisopropyl-, 4-phenoxy-2,6-diisopropyl- and 4-tert-butyl-2,6-diisopropylphenyl isocyanates which can be used for their preparation.Type: GrantFiled: January 30, 1996Date of Patent: April 15, 1997Assignee: BASF AktiengesellschaftInventors: Friedhelm Lehrich, Siegmund Pohl, Bernd Bruchmann, Helmut Tesch, Roland Minges, Johann Swoboda, Manfred Genz, Guenter Scholz, Joachim Streu
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Patent number: 5597942Abstract: Novel carbodiimides and/or oligomeric polycarbodiimides containing terminal isocyanate, urethane and/or urea groups are obtainable, for example, by condensation of 1,3-bis(1-methyl-1-isocyanatoethyl)benzene with elimination of carbon dioxide followed, if desired, by reaction of all or some of the free isocyanate groups of the resultant (poly)carbodiimides with aliphatic, cycloaliphatic or araliphatic amines, alcohols and/or alkoxypolyoxyalkylene alcohols, and are used as stabilizers against hydrolytic degradation of polyaddition and polycondensation products containing ester groups.Type: GrantFiled: January 30, 1996Date of Patent: January 28, 1997Assignee: BASF AktiengesellschaftInventors: Siegmund Pohl, Friedhelm Lehrich, Manfred Genz, Bernd Bruchmann, Helmut Tesch, Roland Minges, Joachim Streu
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Patent number: 5574083Abstract: Disclosed are certain aromatic polycarbodiimides. Also disclosed is the use of an aromatic polycarbodiimide containing only aromatic carbodiimide groups as a cross-linker for a coating binder polymer bearing carboxyl groups.Type: GrantFiled: April 29, 1994Date of Patent: November 12, 1996Assignee: Rohm and Haas CompanyInventors: Ward T. Brown, James C. Day
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Patent number: 5532414Abstract: 4,4'-disubstituted bis-2,6-diisopropylphenyl)carbodiimides of the formula (I) ##STR1## where R is 1-methyl-1-phenylethyl, phenoxy or tert-butyl, a process for their preparation, their use as stabilizers against hydrolytic degradation of polyaddition and polycondensation products containing ester groups, and the novel 4-(1-methyl-1-phenylethyl)-2,6-diisopropyl-, 4-phenoxy-2,6-diisopropyl- and 4-tert-butyl-2,6-diisopropylphenyl isocyanates which can be used for their preparation.Type: GrantFiled: September 24, 1993Date of Patent: July 2, 1996Assignee: BASF AktiengesellschaftInventors: Friedhelm Lehrich, Siegmund Pohl, Bernd Bruchmann, Helmut Tesch, Roland Minges, Johann Swoboda, Manfred Genz, Guenter Scholz, Joachim Streu
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Patent number: 5504241Abstract: There is now provided a carbodiimide or polycarbodiimide of the formula: ##STR1## where the R radicals are identical or different and are selected from the group consisting of --NHCONHR.sup.1 --, --NHCONR.sup.1 R.sup.2 --, and --NHCOOR.sup.3 --, where R.sup.1 and R.sup.2 may be identical or different and are alkyl, cycloalkyl, or aralkyl, and R.sup.3 is identical to R.sup.1 or is alkoxypolyoxyalkylene, and n is an integer from 0 to 10.There is also provided an ester containing plastic which contains this carbodiimide as an anti-hydrolysis agent. The plastics may be a polyurethane cellular or non-cellular elastomer or thermoplastic.Type: GrantFiled: March 7, 1995Date of Patent: April 2, 1996Assignee: BASF AktiengesellschaftInventors: Siegmund Pohl, Friedhelm Lehrich, Manfred Genz, Bernd Bruchmann, Helmut Tesch, Roland Minges, Joachim Streu
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Patent number: 5498747Abstract: The present invention relates to novel carbodiimides or oligomeric polycarbodiimides containing terminal isocyanate, urea and/or urethane groups, methods for their preparation, and their use as hydrolysis stabilizers.Type: GrantFiled: March 7, 1995Date of Patent: March 12, 1996Assignee: BASF AktiengesellschaftInventors: Siegmund Pohl, Friedhelm Lehrich, Manfred Genz, Bernd Bruchmann, Helmut Tesch, Roland Minges, Joachim Streu
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Patent number: 5434305Abstract: A process for the production of aromatic carbodiimides by carbodiimidization of aromatic monoisocyanates in the presence of distillable organic phosphorus compounds as catalyst at 120.degree. to 220.degree. C. up to a maximum degree of carbodiimidization of 80% and subsequent removal by distillation of the unreacted starting isocyanate together with the catalyst from the reaction mixture, optionally together with subsequent preparation by distillation, together with the carbodiimides obtainable in accordance with this process.Type: GrantFiled: December 6, 1993Date of Patent: July 18, 1995Assignee: Rhein Chemie Rheinau GmbHInventors: Hans-Joachim Hennig, Wolfgang Alter, Jorg Lussmann
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Patent number: 5373080Abstract: The present invention provides a process for producing a polycarbodiimide resin from an aliphatic diisocyanate and a terminal-blocking agent in the presence of a carbodiimidization catalyst, wherein the aliphatic diisocyanate is tetramethylxylylene diisocyanate represented by the following formula ##STR1## and polymerization is conducted using no solvent. The polycarbodiimide resin obtained by the above process has good storage stability and excellent miscibility with organic solvents.Type: GrantFiled: August 3, 1993Date of Patent: December 13, 1994Assignee: Nisshinbo Industries, inc.Inventors: Yasuo Imashiro, Ikuo Takahashi
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Patent number: 5360933Abstract: The present invention provides a tetramethylxylylene carbodiimide represented by the following formula ##STR1## wherein R is a monoisocyanate residue and n represents an integer of 1 or more. Said carbodiimide has good storage stability owing to reduced reactivity and gives good handleability in a reaction with an active hydrogen compound.Type: GrantFiled: December 17, 1992Date of Patent: November 1, 1994Assignee: Nisshinbo Industries, Inc.Inventors: Yasuo Imashiro, Ikuo Takahashi
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Patent number: 5357021Abstract: Novel reactive carbodiimide compounds and their method of preparation are disclosed. These reactive carbodiimide compounds are especially useful in automotive paint compositions and more particularly in low volatile organic content (VOC) automotive paint compositions.Type: GrantFiled: July 21, 1993Date of Patent: October 18, 1994Assignee: BASF CorporationInventors: Anthony J. Tye, George G. Beck, Patrick J. Mormile
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Patent number: 5354888Abstract: Organic carbodiimides are produced by carbodiimidization of isocyanate groups with catalysts of the phospholine type. At the end of the carbodiimidization reaction, the catalyst system is removed by introducing carbon dioxide in vacuo at temperatures of from about 100.degree. to about 250.degree. C. The carbodiimides produced by this process are particularly useful as stabilizers for plastics.Type: GrantFiled: January 24, 1994Date of Patent: October 11, 1994Assignee: Bayer AktiengesellschaftInventor: Hans-Joachim Scholl
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Patent number: 5352400Abstract: Processes are provided for making polycarbodiimides with high carbodiimide contents from isocyanates, and for selectively making mixed aryl-tertiary carbodiimides from isocyanates. Also provided are carbodiimides containing alpha-methylstyryl groups, and polymers made therefrom. All of these polymers and compounds are useful in coatings, and for other applications.Type: GrantFiled: April 29, 1992Date of Patent: October 4, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventor: Michael W. J. West
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Patent number: 5349087Abstract: Processes are provided for making polycarbodiimides with high carbodiimide contents from isocyanates, and for selectively making mixed aryl-tertiary carbodiimides from isocyanates. Also provided are carbodiimides containing alpha-methylstyryl groups, and polymers made therefrom. All of these polymers and compounds are useful in coatings, and for other applications.Type: GrantFiled: July 13, 1993Date of Patent: September 20, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventor: Michael W. J. West
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Patent number: 5258481Abstract: The invention describes a new type of multi-functional water-dispersible crosslinking agents. These crosslinking agents are products consisting of oligomeric compounds containing carbodiimide functions and other reactive functional groups. Further the invention describes aqueous dispersions, emulsions or solutions with such crosslinking agents. Finally the invention comprises a process for the preparation of the crosslinking agent according to the invention.Type: GrantFiled: April 3, 1992Date of Patent: November 2, 1993Assignee: Stahl Holland B. V.Inventors: Laurentius C. J. Hesselmans, Johanna A. M. van den Goorbergh
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Patent number: 5246993Abstract: Oligomeric carbodiimides having an average degree of condensation of from 2 to 30, obtainable by oligocondensation ofa) from 40 to 100 mol % of 2,4'-diisocyanatodiphenylmethane or of a 3,3',5,5'-tetra-C.sub.1 -C.sub.4 -alkyl-4,4'-diisocyanatodiphenylmethane andb) from 0 to 60 mol % of a further bi- or polyfunctional aromatic isocyanate andc) if desired, complete or partial reaction of the remaining free isocyanate groups of the oligomers with an aliphatic, araliphatic or cycloaliphatic alcohol or amine,are used mainly for stabilizing polyester-containing polyurethanes against hydrolytic degradation.Type: GrantFiled: August 7, 1992Date of Patent: September 21, 1993Assignee: BASF AktiengesellschaftInventors: Deitrich Scherzer, Roland Minges, Friedhelm Lehrich, Werner Langer
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Patent number: 5208378Abstract: A process for the production of a water-soluble carbodiimide, which comprises(1) allowing ethyl isothiocyanate to react with N,N-dimethyl-1,3-propanediamine in an aromatic hydrocarbon solvent (first reaction step),(2) removing hydrogen sulfide from a thiourea derivative formed in the first reaction step upon adding a hydrogen sulfide removing agent without isolating the thiourea derivative (second reaction step), and(3) recovering a water-soluble carbodiimide from the resulting reaction mixture.Type: GrantFiled: July 18, 1991Date of Patent: May 4, 1993Assignee: Research Association for Utilization of Light OilInventors: Takahiro Yoneyama, Masaki Odagiri, Makoto Imanari
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Patent number: 5136006Abstract: Carbodiimide compounds having the following structural formula are claimed: ##STR1## Z being selected from the group consisting of the following moieties: ##STR2## wherein R.sub.1 represents an alkylidene radical;R.sub.2 represents hydrogen or an alkyl radical;R.sub.3 represents an alkyl radical, an aromatic hydrocarbon moiety or a cycloaliphatic hydrocarbon moiety or substituted derivatives thereof;R.sub.4 represents an aromatic hydrocarbon moiety;R.sub.5 represents an alkyl radical; andx is an integer ranging from 1 to 6.Polymers containing moieties of at least two such carbodiimide compounds depending therefrom are also claimed and are useful in the formulation of coating compositions which harden or cure at low temperatures.Type: GrantFiled: January 8, 1992Date of Patent: August 4, 1992Assignee: PPG Industries, Inc.Inventors: Padmanabhan Sundararaman, James A. Claar, Charles M. Kania
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Patent number: 5117059Abstract: Branched, monodisperse, multifunctional carbodiimides which are particularly useful as cross-linkers for carboxyl-containing resins.Type: GrantFiled: January 24, 1991Date of Patent: May 26, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: James W. Tylor
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Patent number: 5114975Abstract: The invention relates to novel substituted aryloxyphenylthioureas, aryloxyphenylisothioureas and aryloxyphenylcarobodiimides of formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.12 alkyl, unsubstituted or substituted by one or more halogen atoms and/or C.sub.1 -C.sub.6 alkoxy groups; C.sub.3 -C.sub.8 cycloalkyl, unsubstituted or substituted by one or more C.sub.1 -C.sub.3 alkyl groups; or C.sub.3 -C.sub.8 cycloalkyl-C.sub.1 -C.sub.4 alkyl,R.sub.2 and R.sub.3 are each C.sub.1 -C.sub.5 alkyl or C.sub.5 -C.sub.6 cycloalkyl,R.sub.4 is hydrogen, methyl or --CHO,R.sub.5 is halogen; C.sub.1 -C.sub.4 alkyl, unsubstituted or substituted by one or more halogen atoms; C.sub.1 -C.sub.4 alkoxy, unsubstituted or substituted by one or more halogen atoms; or is a --CH.dbd.CH).sub.2, --CH.sub.2).sub.3 or --CH.sub.2).sub.4 bridge in 2,3- or 3,4-position,n is 0, 1, 2, 3 or 4,Z is --NH--CS--NH--, --N.dbd.C(SR.sub.6)--NH-- or --N.dbd.C.dbd.N--; andR.sub.6 is C.sub.1 -C.sub.Type: GrantFiled: April 3, 1991Date of Patent: May 19, 1992Assignee: Ciba-Geigy CorporationInventors: Manfred Boger, Jozef Drabek, Josef Ehrenfreund
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Patent number: 5108653Abstract: Disclosed are surface-active polycarbodiimides containing a hydrophilic portion and a hydrophobic portion joined through the reaction of a carbodiimide group with a reactive functional group. The surface-active polycarbodiimides may be linear or branched, monodisperse or polydisperse, but preferably are of the branched, monodisperse type. The surface-active polycarbodiimides are useful as surfactants, and are particularly useful as emulsifiers in cross-linkable, carboxyl-containing resin systems, such as aqueous latexes.Type: GrantFiled: June 12, 1991Date of Patent: April 28, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: James W. Taylor
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Patent number: 5107021Abstract: The invention relates to polyfluoroalkyl nitrogen compounds of general formula:R.sub.F --(CH.sub.2).sub.2 --Xin which X denotes an isothiocynate --N.dbd.C.dbd.S, carbodiimide --N.dbd.C.dbd.N(CH.sub.2).sub.2 --R'.sub.F or thiourea --NH--CS--A group, A denoting an optionally substituted amino group, and each of the symbols R.sub.F and R'.sub.F denotes a perfluoroalkyl radical.These compounds, prepared from the corresponding azides R.sub.F (CH.sub.2).sub.2 N.sub.3 or amines R.sub.F (CH.sub.2).sub.2 NH.sub.2, can be used as surface-active agents or precursors of such agents.Type: GrantFiled: April 12, 1991Date of Patent: April 21, 1992Assignee: Societe ATOCHEMInventors: Eric Bollens, Francois Szonyi, Aime Cambon
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Patent number: 5105010Abstract: Carbodiimide compounds having the following structural formula are claimed: ##STR1## Z being selected from the group consisting of the following moieties: ##STR2## wherein R.sub.1 represents an alkylidene radical;R.sub.2 represents hydrogen or an alkyl radical;R.sub.3 represents an alkyl radical, an aromatic hydrocarbon moiety or a cycloaliphatic hydrocarbon moiety or substituted derivatives thereof;R.sub.4 represents an aromatic hydrocarbon moiety;R.sub.5 represents an alkyl radical; andx is an integer ranging from 1 to 6.Polymers containing moieties of at least two such carbodiimide compounds depending therefrom are also claimed and are useful in the formulation of coating compositions which harden or cure at low temperatures.Type: GrantFiled: June 13, 1991Date of Patent: April 14, 1992Assignee: PPG Industries, Inc.Inventors: Padmanabhan Sundararaman, James A. Claar, Charles M. Kania
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Patent number: 5047588Abstract: Disclosed are surface-active polycarbodiimides containing a hydrophilic portion and a hydrophobic portion joined through the reaction of a carbodiimide group with a reactive functional group. The surface-active polycarbodiimides may be linear or branched, monodisperse or polydisperse, but preferably are of the branched, monodispers type. The surface-active polycarbodiimides are useful as surfactants, and are particularly useful as emulsifiers in cross-linkable, carboxyl-containing resin systems, such as aqueous latexes.Type: GrantFiled: January 30, 1989Date of Patent: September 10, 1991Assignee: Union Carbide Chemicals and Plastics Technology CorporationInventor: James W. Taylor
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Patent number: 5030738Abstract: To synthesize molecules with antiulcer action, specifically ranitidine, niperotidine and cimetidine, having the formula: ##STR1## wherein R.sub.1 is hydrogen or together with R.sub.2 represents the rest of a cycloaliphatic or heterocyclic optionally substituted ring with 5 or 6 carbon atoms, R.sub.2 represents H, alkyl, alkyl substituted with a simple or substituted aromatic ring or with a single or substituted heterocyclic ring, Ar represents a simple or substituted phenyl group, a simple or substituted heterocyclic aromatic group, N=1, 2, 3, 4, 5 or 6 and X represents CH--NO.sub.2, S, N--C.tbd.N, the compound (II) is prepared through the following process sequence: ##STR2## wherein Z=H, NO.sub.2, halogen and R.sub.3 =--(CH.sub.2).sub.n Ar, --(CH.sub.2).sub.n --SH, --(CH.sub.2).sub.n --S--S--(CH.sub.2).sub.n, --(CH.sub.2).sub.n --S--CH.sub.2 Ar Y being halogen.Type: GrantFiled: May 22, 1990Date of Patent: July 9, 1991Assignee: Janus Farmaceutici S.r.l.Inventor: Alberto Reiner
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Patent number: 5026730Abstract: The invention relates to novel substituted anilinophenylthioureas, anilinophenylisothioureas and anilinophenylcarbodiimides of formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.12 alkyl, unsubstituted or substituted by one or more halogen atoms and/or C.sub.1 -C.sub.6 alkoxy groups; C.sub.3 -C.sub.8 cycloalkyl, unsubstituted or substituted by one or more C.sub.1 -C.sub.3 alkyl groups; or C.sub.3 -C.sub.8 cycloalkyl-C.sub.1 -C.sub.4 alkyl,R.sub.2 and R.sub.3 are each C.sub.1 -C.sub.5 alkyl or C.sub.5 -C.sub.6 cycloalkyl,R.sub.4 is hydrogen, methyl or --CHO,R.sub.5 is halogen; C.sub.1 -C.sub.4 alkyl, unsubstituted or substituted by one or more halogen atoms; C.sub.1 -C.sub.4 alkoxy, unsubstituted or substituted by one or more halogen atoms; or is a --CH.dbd.CH--.sub.2, --CH.sub.2--3 or --CH.sub.2--4 bridge in 2,3- or 3,4-position,n is 0, 1, 2, 3 or 4,Z is --NH--CS--NH--, --N.dbd.C(SR.sub.6)--NH-- or --N.dbd.C.dbd.N--; andR.sub.6 is C.sub.1 -C.sub.Type: GrantFiled: August 11, 1988Date of Patent: June 25, 1991Assignee: Ciba-Geigy CorporationInventors: Manfred Boger, Jozef Drabek, Josef Ehrenfreund
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Patent number: 5026910Abstract: The invention relates to polyfluoroaklyl nitrogen compounds of general formula:R.sub.F --(CH.sub.2).sub.2 --Xin which X denotes an isothiocyanate --N.dbd.C.dbd.S, carbodiimide --N.dbd.C.dbd.N(CH.sub.2).sub.2 --R'.sub.F or thiourea --NH--CS--A group, A denoting an optionally substituted amino group, and each of the symbols R.sub.F and R'.sub.F denotes a perfluoroalkyl radical.these compounds, prepared from the corresponding axides R.sub.F (CH.sub.2).sub.2 N.sub.3 or amines R.sub.F(CH.sub.2).sub.2 NH.sub.2, can be used as surface-active agents or precursors of such agents.Type: GrantFiled: May 22, 1990Date of Patent: June 25, 1991Assignee: Societe AtochemInventors: Eric Bollens, Francois Szonyi, Aime Cambon
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Patent number: 4990232Abstract: The photooxidation of N,N'-substituted thioureas with oxygen in the presence of an acid-trapping agent gives N,N'-substituted carbodiimides. The carbodiimides can be converted into cyanoguanidines, which are suitable as latent curing agents for epoxy resins.Type: GrantFiled: September 2, 1988Date of Patent: February 5, 1991Assignee: Ciba-Geigy CorporationInventor: Alex Alder
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Patent number: 4968720Abstract: Novel substituted phenyl-thioureas, -isothioureas and -carbodiimides of formula I ##STR1## in which R.sub.1 is C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 alkyl mono- or poly-substituted by halogen and/or by C.sub.1 -C.sub.6 alkoxy, C.sub.3 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.8 cycloalkyl mono- or poly-substituted by C.sub.1 -C.sub.3 alkyl, or is C.sub.3 -C.sub.8 cycloalkyl-C.sub.1 -C.sub.4 alkyl; each of R.sub.2 and R.sub.3 is C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.6 cycloalkyl or C.sub.5 -C.sub.6 cycloalkenyl; each of R.sub.4 and R.sub.5 is hydrogen or C.sub.1 -C.sub.4 alkyl; each R.sub.6 is halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy or a --CH.dbd.CH.sub.2, --CH.sub.2 or --CH.sub.2 bridge in the 2,3- or 3,4-position; n is 0, 1 or 2; Z is --NH--CS--NH--, --N.dbd.C(SR.sub.7 --NH-- or --N.dbd.C.dbd.N--, and R.sub.7 is C.sub.1 -C.sub.10 alkyl or C.sub.3 -C.sub.Type: GrantFiled: August 12, 1988Date of Patent: November 6, 1990Assignee: Ciba-Geigy CorporationInventor: Josef Ehrenfreund
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Patent number: 4965389Abstract: The invention relates to novel phenoxyphenylthioureas, phenoxyphenylisothioureas and phenoxyphenylcarbodiimides of formula I ##STR1## wherein R.sub.1 is C.sub.3 -C.sub.7 cycloalkyl or C.sub.5 -C.sub.6 cycloalkenyl,R.sub.2 is C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.6 cycloalkyl or C.sub.5 -C.sub.6 cycloalkyenyl,R.sub.3 is C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.6 cycloalkyl, 1-cyclopropylethyl or C.sub.3 -C.sub.5 alkenyl,R.sub.4 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy or CF.sub.3,n is an integer from 1 to 3,Z is --NH--CS--NH--, --N.dbd.C(SR.sub.5)--NH-- or --N.dbd.C.dbd.N--, andR.sub.5 is C.sub.1 -C.sub.5 alkyl or allyl,and to salts thereof, to the preparation of these compounds and to intermediates for their synthesis. The invention further relates to the use of the novel compounds in pest control and to pesticidal compositions which contain at least one compound of formula I. The preferred utility is the control of pests of animals and plants.Type: GrantFiled: March 1, 1988Date of Patent: October 23, 1990Assignee: Ciba-Geigy CorporationInventor: Josef Ehrenfreund
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Patent number: 4921876Abstract: The invention relates to novel substituted carbodiimides of the formula ##STR1## wherein R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.5 alkoxy, C.sub.1 -C.sub.5 alkoxy which is substituted by 1 to 7 halogen atoms, or is C.sub.1 -C.sub.5 alkylthio;R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.10 alkyl or C.sub.1 -C.sub.5 alkoxy;R.sub.3 is hydrogen, C.sub.1 -C.sub.10 alkyl, halogen, phenoxy, phenylthio, or is phenoxy or phenylthio, each mono- or disubstituted by a member selected from the group consisting of halogen, methyl, ethyl, C.sub.1 -C.sub.3 haloalkyl containing 1 to 7 halogen atoms and cyano, or is pyridyloxy or pyridyloxy which is mono- or disubstituted by a member selected from the group consisting of halogen and C.sub.1 -C.sub.3 haloalkyl containing 1 to 7 halogen atoms;R.sub.4 is C.sub.1 -C.sub.12 alkyl, alkoxyalkyl containing a total of 2 to 10 carbon atoms, C.sub.3 -C.sub.10 cycloalkyl, C.sub.3 -C.sub.10 cycloalkylmethyl, C.sub.3 -C.sub.Type: GrantFiled: December 22, 1988Date of Patent: May 1, 1990Assignee: Ciba-Geigy CorporationInventors: Manfred Boger, Josef Drabek
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Patent number: 4910339Abstract: The present invention is directed to isocyanate derivatives containing about 2 to 30% by weight of carbodiimide groups, --N.dbd.C.dbd.N--, on a statistical average at least about 0.8 carbodiimide groups per molecule, about 5 to 200 milliequivalents per 100 g of solids of chemically incorporated sulfonate groups and, optionally, 0 to about 25%, based on solids, of chemically incorporated ethylene oxide units, --CH.sub.2 --CH.sub.2 --O--, in polyether chains. The present invention is also directed to a process for the preparation of these isocyanate derivatives and to their use as additives for aqueous dispersions or solutions of plastics containing carboxyl groups or groups convertible into carboxyl groups.Type: GrantFiled: March 27, 1986Date of Patent: March 20, 1990Assignee: Bayer AktiengesellschaftInventors: Wolfgang Henning, Walter Meckel
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Patent number: 4820863Abstract: Disclosed are surface-active polycarbodiimides containing a hydrophilic portion and a hydrophobic portion joined through the reaction of a carbodiimide group with a reactive functional group. The surface-active polycarbodiimides may be linear or branched, monodisperse or polydisperse, but preferably are of the branched, monodisperse type. The surface-active polycarbodiimides are useful as surfactants, and are particularly useful as emulsifiers in cross-linkable, carboxyl-containing resin systems, such as aqueous latexes.Type: GrantFiled: March 31, 1986Date of Patent: April 11, 1989Assignee: Union Carbide CorporationInventor: James W. Taylor
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Patent number: 4812466Abstract: The invention relates to novel substituted carbodiimides of the formula ##STR1## wherein R.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.5 alkoxy, C.sub.1 -C.sub.5 alkoxy which is substituted by 1 to 7 halogen atoms, or is C.sub.1 -C.sub.5 alkylthio;R.sub.2 is hydrogen, halogen, C.sub.1 -C.sub.10 alkyl or C.sub.1 -C.sub.5 alkoxy;R.sub.3 is hydrogen, C.sub.1 -C.sub.10 alkyl, halogen, phenoxy, phenylthio, or is phenoxy or phenylthio, each mono- or disubstituted by a member selected from the group consisting of halogen, methyl, ethyl, C.sub.1 -C.sub.3 haloalkyl containing 1 to 7 halogen atoms and cyano, or is pyridyloxy or pyridyloxy which is mono- or disubstituted by a member selected from the group consisting of halogen and C.sub.1 -C.sub.3 haloalkyl containing 1 to 7 halogen atoms;R.sub.4 is C.sub.1 -C.sub.12 alkyl, alkoxyalkyl containing a total of 2 to 10 carbon atoms, C.sub.3 -C.sub.10 cycloalkyl, C.sub.3 -C.sub.10 cycloalkylmethyl, C.sub.3 -C.sub.Type: GrantFiled: October 26, 1987Date of Patent: March 14, 1989Assignee: Ciba-Geigy CorporationInventors: Manfred Boger, Jozef Drabek
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Patent number: 4487964Abstract: Mixed aliphatic/aromatic polycarbodiimides can be prepared by first heating aliphatic mono- and diisocyanates with a phospholene oxide catalyst and then feeding the aromatic mono and/or diisocyanates in an inert solvent to the reaction mixture, thus preparing cross-linking agents for carboxylated latexes used in making roofing materials, hardboard, pressure sensitive adhesives and the like.Type: GrantFiled: February 24, 1983Date of Patent: December 11, 1984Assignee: Union Carbide CorporationInventors: Stuart L. Watson, Jr., Gordon R. Humphreys
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Patent number: 4467395Abstract: An AC metallized film capacitor having a plurality of electrodes separated by a dielectric spacer contains as its impregnant system an ester dielectric fluid and 2 to 10% of a N,N-substituted carbodiimide to improve capacitance retention characteristics.Type: GrantFiled: February 25, 1983Date of Patent: August 21, 1984Assignee: Sprague Electric CompanyInventor: Sidney D. Ross
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Patent number: 4321394Abstract: The instant invention is directed to a process for the production of addition compounds of compounds containing hydroxyl groups and carbodiimides substantially free from isocyanate groups, comprising reacting the reactants in the presence of from 0.01 to 3% by weight, based on the reaction mixture, of a metal catalyst, the improvement wherein a tin compound is used as said metal catalyst.Type: GrantFiled: September 24, 1980Date of Patent: March 23, 1982Assignee: Bayer AktiengesellschaftInventors: Walter Schafer, Kuno Wagner, Kurt Findeisen