Trimerization Process To Form The Triazine Ring Patents (Class 544/193)
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Patent number: 12104007Abstract: An allophanate group-containing polyisocyanate composition that contributes to the formation of a polyurethane resin with fewer bubbles is provided. Disclosed is an allophanate group-containing polyisocyanate composition (C) including a reaction product of diphenylmethane diisocyanate (A) and a hydroxyl group-containing compound (B), wherein the hydroxyl group-containing compound (B) includes a hydroxyl group-containing polymethylsiloxane compound (B-1) in an amount of 1 ppm or more and 300 ppm or less.Type: GrantFiled: July 24, 2019Date of Patent: October 1, 2024Assignee: TOSOH CORPORATIONInventors: Mitsushige Ikemoto, Futoshi Oota
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Patent number: 10991981Abstract: This nonaqueous electrolyte secondary battery is provided with a positive electrode, a negative electrode and a non-aqueous electrolyte. The non-aqueous electrolyte contains: a non-aqueous solvent that contains a fluorine-containing cyclic carbonate; an isocyanuric acid derivative such as triallyl isocyanurate; and a cyclic carboxylic acid anhydride such as diglycolic acid anhydride.Type: GrantFiled: December 14, 2017Date of Patent: April 27, 2021Assignee: PANASONIC INTELLECTUAL PROPERTY MANAGEMENT CO., LTD.Inventors: Masaki Hasegawa, Yuanlong Zhong
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Patent number: 10717805Abstract: The invention relates to a process for producing polyisocyanurate plastics, comprising the following steps: (a) providing a polyisocyanate composition A) which contains oligomeric polyisocyanates and is low in monomeric diisocyanates, where the isocyanurate structure content in the polyisocyanate composition A) is at least 50 mol %, based on the sum total of the oligomeric structures from the group consisting of uretdione, isocyanurate, allophanate, biuret, iminooxadiazinedione and oxadiazinetrione structure that are present in the polyisocyanate composition A); (b) catalytically trimerizing the polyisocyanate composition A), where (i) the catalytic trimerization is conducted at ambient temperatures of at least 80° C.; (ii) the catalytic trimerization is conducted within less than 12 hours at least up to a degree of conversion at which only still not more than 20% of the isocyanate groups originally present in the polyisocyanate composition A) are present.Type: GrantFiled: April 21, 2016Date of Patent: July 21, 2020Assignee: Covestro Deutschland AGInventors: Mathias Matner, Dirk Achten, Hans-Josef Laas, Heiko Hocke, Dieter Mager
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Patent number: 9908964Abstract: A process for providing isocyanurate modified methyl diphenyl diisocyanate is provided, the process comprises determine the NCO-value of the MDI; define the NCO-value for MDI; define a ratio of the volume of the MDI to be trimerised over volume of the MDI not to be trimerised; determine, in function of this ratio, the NCO-value of the isocyanurate modified MDI to be provided and the NCO-value of the MDI a target NCO-value for the part of MDI to be trimerised; divide the MDI in two part according to the defined ratio; provide a trimerised part of the MDI by trimerising one of these parts until the target NCO-value is obtained; and terminate the trimerisation by killing the trimerisation catalyst and blend the two parts with each other.Type: GrantFiled: March 1, 2011Date of Patent: March 6, 2018Assignee: HUNTSMAN INTERNATIONAL LLCInventors: Nicole Mangelschots, Joris Karel Peter Bosman
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Patent number: 9840579Abstract: Thixotropic polyol dispersions are described. The dispersions contain a dispersed phase of polyurethane-isocyanurate particles. They can be made by reacting a low equivalent weight polyol with a polyisocyanate in the presence of an isocyanate trimerization catalyst while dispersed in a base polyol. These polyol dispersions are useful as the resin component of curable systems such as formulated coatings, sealants or adhesives.Type: GrantFiled: September 11, 2014Date of Patent: December 12, 2017Assignee: Dow Global Technologies LLCInventors: Irena Amici-Kroutilova, Paul Cookson, Daniel Hoenhener, Francois Casati
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Patent number: 9815739Abstract: The present invention provides an oil or gas wellbore polymeric cement comprising the reaction product of an aliphatic isocyanate, a trimerization catalyst, and a catalyst retarder, wherein the reaction occurs in the wellbore at a temperature of at least 250° F. (121° C.). Also provided is a method of reducing fluid loss from an oil or gas well, comprising producing a polyisocyanurate cement by combining an aliphatic isocyanate, a trimerization catalyst, and a catalyst retarder within a wellbore at a temperature of at least 250° F. (121° C.). The various embodiments of the invention meet the controllability and minimized toxicity needed for this application. Standard aliphatic polyisocyanates reduce handling concerns while providing the reactivity response that fits this temperature range.Type: GrantFiled: October 30, 2015Date of Patent: November 14, 2017Assignee: Covestro LLCInventors: David P Zielinski, Michael K. Jeffries
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Patent number: 9631043Abstract: A stable partly cured polyisocyanate composition is disclosed which comprises polyisocyanurate (intermediate polyisocyanurate comprising material) and which is further curable. Furthermore a process for making the intermediate (partly cured) polyisocyanurate comprising material and a process for further curing the partly cured polyisocyanurate composition is disclosed. Also polyisocyanurate comprising materials made or obtainable from partly cured intermediate polyisocyanurate comprising material are disclosed and processes for further curing a partly cured polyisocyanurate comprising composition (intermediate material).Type: GrantFiled: June 18, 2013Date of Patent: April 25, 2017Assignee: HUNTSMAN INTERNATIONAL LLCInventors: Christian Esbelin, Hugo Verbeke, Hans Godelieve Guido Verbeke
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Patent number: 9567359Abstract: A material with the empirical formula C3N3P is made by polymerizing P(CN)3 in a polar aprotic solvent such as acetonitrile, by heating, irradiation with ultraviolet light, and/or using a polymerization initiator and/or a catalyst.Type: GrantFiled: June 22, 2016Date of Patent: February 14, 2017Assignee: The United States of America, as represented by the Secretary of the NavyInventors: Albert Epshteyn, Brian L. Chaloux
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Patent number: 9481758Abstract: The invention relates to a polyisocyanurate comprising isocyanurate rings linked by linker groups coupled to the nitrogen atoms of said rings. The polyisocyanurate may be microporous or mesoporous or both microporous and mesoporous.Type: GrantFiled: April 9, 2009Date of Patent: November 1, 2016Assignee: Agency for Science, Technology & ResearchInventors: Yugen Zhang, Jackie Y. Ying, Siti Nurhanna Binte Riduan
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Patent number: 9409936Abstract: A new graphitic material has the empirical formula C3N3P and comprises triazine rings bound together by phosphorus atoms, and/or other 5- or 6-membered rings with various carbon, nitrogen, and phosphorous connectivity. The material is made by polymerizing P(CN)3, for example by using a temperature of at least 220° C. and an elevated pressure, optionally as high as 1500° C. and 12 GPa.Type: GrantFiled: August 6, 2015Date of Patent: August 9, 2016Assignee: The United States of America, as represented by the Secretary of the NavyInventors: Albert Epshteyn, Brendan Yonke, Timothy Strobel, Huiyang Gou
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Patent number: 9376405Abstract: The instant invention relates to novel water soluble bis-(triazinylamino)-stilbene optical brightening agents, a process for their preparation and their use for whitening natural and synthetic materials.Type: GrantFiled: April 17, 2012Date of Patent: June 28, 2016Assignee: CLARIANT INTERNATIONAL LTDInventors: Cedric Klein, Frederic Reveaud, Andrew Clive Jackson, David Atkinson
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Patent number: 8952120Abstract: An isocyanurate type polyisocyanate composition which is derived from an aliphatic diisocyanate monomer and an alcohol and satisfies all of the following requirements when it contains substantially no aliphatic diisocyanate monomer and substantially no solvent: 1) the viscosity at 25° C. is 500-1,500 mPa·s; 2) the isocyanurate trimer concentration is 60-95 mass %; 3) when the number of allophanate bonds is expressed as A and the number of isocyanurate bonds is expressed as B, the proportion of the allophanate bonds, a=(A/(A+B))×100, is 1-30%; and 4) when the number of urethodione bonds is expressed as D, the proportion of the urethodione bonds, d=(D/(B+D))×100, is less than 2%.Type: GrantFiled: September 21, 2006Date of Patent: February 10, 2015Assignee: Asahi Kasei Chemicals CorporationInventors: Yoshiyuki Asahina, Masakazu Yamauchi
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Patent number: 8785440Abstract: The present invention provides compounds useful as inhibitors of Btk, compositions thereof, and methods of using the same.Type: GrantFiled: September 3, 2010Date of Patent: July 22, 2014Assignees: Biogen Idec MA, Inc., Sunesis Pharmaceuticals, Inc.Inventors: Minna Bui, Patrick Conlon, Julio H. Cuervo, Daniel A. Erlanson, Junfa Fan, Bing Guan, Brian T. Hopkins, Tracy J. Jenkins, Gnanasambandam Kumaravel, Alexey A. Lugovskoy, Doug Marcotte, Noel Powell, Daniel Scott, Laura Silvian, Art Taveras, Deping Wang, Min Zhong
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Publication number: 20130324720Abstract: A system and process for melamine production by gas-phase quenching method and its process are provided. The said system includes a urea scrubber, after which a fluidized bed reactor, a hot-air cooler, a hot-air filter, a crystallizer and a melamine collector are installed in series successively, where the said melamine collector is connected to the said urea scrubber and the said fluidized bed reactor is connected to a carrier gas pre-heater which is connected to a carrier gas compressor; the said system further includes a gas-liquid separator which is connected to the said urea scrubber which is connected to a crystallizer; wherein a cool air blower is provided between the said gas-liquid separator and the crystallizer. The production system of the invention has the advantages of high productivity, stable operation, low energy consumption, low investment and high economic value of tail gas.Type: ApplicationFiled: April 20, 2012Publication date: December 5, 2013Applicants: SICHUAN GOLDEN-ELEPHANT SINCERITY CHEMICAL CO.,LTD, BEIJING EDGEIN TECHNOLOGY CO., LTD.Inventors: Yin Tang, Zhongwu Yuan, Yuande Gong, Mingda Yin, Xiuzhen Yang, Duanyang Chen, Jianglin Yi, Lin Lei, Chaohui Liu, Xuchu Li, Xikun Xiong, Hui Chen, Deli Kong, Wenmao Jiang, Gang Li, Lihong Guo, Zhongyun Li, Guangsong Lan, Guohua Yuan, Xiangdong Kuang
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Publication number: 20130303758Abstract: The present invention relates to a novel process for preparing polyisocyanates having isocyanurate groups by a partial trimerization of (cyclo)aliphatic diisocyanates in the presence of at least one trimerization catalyst from the group of ammonium salts of lactames and to the use of the thus obtainable polyisocyanates having isocyanurate groups as a polyisocyanate component in polyurethane coatings.Type: ApplicationFiled: May 8, 2013Publication date: November 14, 2013Applicant: BASF SEInventors: Frederic LUCAS, Angelika Maria STEINBRECHER, Philippe DESBOIS
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Patent number: 8445622Abstract: The present invention relates to a process for preparing polyisocyanates by oligomerization of isocyanates.Type: GrantFiled: November 30, 2007Date of Patent: May 21, 2013Assignee: BASF SEInventors: Horst Binder, Hubert Graf
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Patent number: 8415471Abstract: This invention relates to flexible cycloaliphatic diisocyanate trimers and a process for the preparation of these. These flexible products are allophanate-modified, partially trimerized cycloaliphatic diisocyanates and are characterized by a low Tg. More specifically, the Tg of the resultant product ranges from about ?30° C. to about 40° C., after the excess monomer has been removed from the product.Type: GrantFiled: November 29, 2007Date of Patent: April 9, 2013Assignee: Baver MaterialScience LLCInventors: Myron W. Shaffer, Michael K. Jeffries, David P. Zielinski
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Patent number: 8373004Abstract: The present invention relates to a novel process for preparing colorless, isocyanurate group-comprising polyisocyanates of (cyclo)aliphatic diisocyanates.Type: GrantFiled: March 27, 2008Date of Patent: February 12, 2013Assignee: BASF SEInventors: Harald Schaefer, Carl Jokisch, Horst Binder, Matthias Kroner, Alexander Bayer
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Publication number: 20130023659Abstract: A process for providing isocyanurate modified methyl diphenyl diisocyanate is provided, the process comprises determine the NCO-value of the MDI; define the NCO-value for MDI; define a ratio of the volume of the MDI to be trimerised over volume of the MDI not to be trimerised; determine, in function of this ratio, the NCO-value of the isocyanurate modified MDI to be provided and the NCO-value of the MDI a target NCO-value for the part of MDI to be trimerised; divide the MDI in two part according to the defined ratio; provide a trimerised part of the MDI by trimerising one of these parts until the target NCO-value is obtained; and terminate the trimerisation by killing the trimerisation catalyst and blend the two parts with each other.Type: ApplicationFiled: March 1, 2011Publication date: January 24, 2013Applicant: Huntsman International LLCInventors: Nicole Mangelschots, Joris Karel Peter Bosman
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Patent number: 8324249Abstract: The invention relates to tetrahydropyridinyl and dihydropyrrolyl compounds of Formula (I): and pharmaceutically acceptable salts, prodrugs, or solvates thereof, wherein X, Y, Z, R1, R2, m, and n are defined as set forth in the specification. The invention is also directed to the use of compounds of Formula (I) to treat a disorder responsive to the blockade of calcium channels, and particularly N-type calcium channels. Compounds of the present invention are especially useful for treating pain.Type: GrantFiled: August 3, 2009Date of Patent: December 4, 2012Assignees: Purdue Pharma L.P., Shionogi & Co., Ltd.Inventors: Hidenori Mikamiyama, Chiyou Ni, Bin Shao, Laykea Tafesse
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Patent number: 8269044Abstract: Disclosed is a method for producing a primary amine compound represented by the formula (3): wherein, Ar is as defined below, which is characterized in that a halogen compound represented by the formula (1): wherein, Ar represents an unsubstituted aromatic group such as a phenyl group, a naphthyl group, a pyridyl group, a furyl group, a thienyl group, a pyrrolyl group, an oxazolyl group, an isoxazolyl group or a pyrimidinyl group, or an aromatic group obtained by substituting such an unsubstituted aromatic group with 1-3 substituents; and X represents a halogen atom, ammonia and formaldehyde are reacted with each other, thereby obtaining a hexahydrotriazine compound represented by the formula (2): wherein, Ar is as defined above, and then the thus-obtained hexahydrotriazine compound is decomposed. By this method, a primary amine compound can be commercially advantageously produced by using a low-cost ammonia while suppressing production of a secondary amine as a by-product.Type: GrantFiled: December 14, 2006Date of Patent: September 18, 2012Assignee: Sumitomo Chemical Company, LimitedInventors: Naoyuki Takano, Kazuyuki Tanaka, Shinzo Seko
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Patent number: 8148488Abstract: Disclosed is a polyisocyanate composition which is excellent in both curability and drying characteristic. The polyisocyanate composition contains at least one compound selected from aliphatic diisocyanates, at least one compound selected from alicyclic diisocyanates and at least one compound selected from polyols, while satisfying all of the following conditions; i) the diisocyanate monomer concentration is not more than 3 mass %, ii) the polyol component concentration is 1-50 mass %; and iii) the glass transition temperature is from ?50° C. to 0° C.Type: GrantFiled: March 1, 2005Date of Patent: April 3, 2012Assignee: Asahi Kasei Chemicals CorporationInventors: Yoshiyuki Asahina, Masakazu Yamauchi, Hironori Katagawa
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Patent number: 8119799Abstract: The present invention relates to novel catalysts for preparing polyisocyanates having isocyanurate groups by a partial trimerization of (cyclo)aliphatic diisocyanates.Type: GrantFiled: March 9, 2005Date of Patent: February 21, 2012Assignee: BASF AktiengesellschaftInventors: Horst Binder, Hubert Graf, Frank Braun, Bernd Spies, Heinrich Kieslich
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Publication number: 20110201709Abstract: The instant invention provides an isocyanate trimerisation catalyst system, a precursor formulation, a process for trimerising isocyanates, rigid foams made therefrom, and a process for making such foams. The trimerisation catalyst system comprises: (a) an imidazolium or imidazolinium cation; and (b) an isocyanate-trimer inducing anion; wherein said trimerisation catalyst system has a trimerisation activation temperature in the range of equal to or less than 73° C. The precursor formulation comprises: (1) at least 25 percent by weight of polyol, based on the weight of the precursor formulation; (2) less than 15 percent by weight of a trimerisation catalyst system, based on the weight of the precursor formulation, comprising; (a) an imidazolium or imidazolinium cation; and (c) an isocyanate-trimer inducing anion; wherein said trimerisation catalyst system has a trimerisation activation temperature in the range of equal to or less than 73° C.Type: ApplicationFiled: November 9, 2009Publication date: August 18, 2011Applicant: Dow Global Technologies LLCInventors: Phillip Athey, Nathan Wilmot, Richard Keaton, David A. Babb, Cecile Boyer, Timothy Morley
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Patent number: 7989576Abstract: A triazine derivative represented by formula (I) below: where, in formula (I), each of M1a, M1b, M2a and M2b is a divalent group comprising one or more substituted or non-substituted aromatic rings; each of n1 and n2 is 0 or 1; each of R1 and R2 represents a hydrogen atom or substituent; and X represents a substituent; is disclosed.Type: GrantFiled: February 28, 2008Date of Patent: August 2, 2011Assignee: Fujifilm CorporationInventors: Aiko Yoshida, Hiroshi Takeuchi
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Patent number: 7825243Abstract: A process is provided for the production of isocyanatosilane from silylorganocarbamate in a cracking zone with a predetermined portion of purged reaction medium undergoing conversion in a trimerization zone to silylisocyanurate.Type: GrantFiled: June 3, 2005Date of Patent: November 2, 2010Assignee: Momentive Performance Materials Inc.Inventors: R. Shawn Childress, Patrick J. Burns
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Publication number: 20100121054Abstract: The present invention provides a process that enables a substituted methylamine compound which is useful as an intermediate for the production of agricultural chemicals and medicines, to be produced easily, with good yield, and at low cost, and also provides a production intermediate thereof. The process comprises a step of reacting a hexamethylenetetraammonium salt compound represented by a formula (I) with a base to obtain an N-methylidene-substituted methylamine oligomer represented by a formula (II) or a mixture of two or more of the oligomers, and a step of hydrolyzing the N-methylidene-substituted methylamine oligomer represented by formula (II) or the mixture of two or more of the oligomers in the presence of an acid.Type: ApplicationFiled: April 24, 2007Publication date: May 13, 2010Applicant: Nippon Soda Co., Ltd.Inventors: Yasushi Shibata, Tsutomu Imagawa
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Patent number: 7556910Abstract: The present invention relates to a photosensitive composition comprising a triazine-based photoactive compound containing oxime ester. The photosensitive composition according to the present invention has good sensitivity, retention rate, mechanical strength, heat resistance, chemical resistance and developing durability since it contains, as photopolymerization initiator, a compound having an oxime ester group and a triazine group in one molecule and thus effectively absorbs UV radiation. Therefore, the photosensitive composition according to the present invention is advantageous not only in curing of materials for color filters, resin black matrixes, column spacers, overcoats and passivation films of liquid crystal displays, but also in high temperature process characteristics.Type: GrantFiled: November 29, 2006Date of Patent: July 7, 2009Assignee: LF Chem, Ltd.Inventors: Sung Hyun Kim, Kyung Jun Kim, Dong Chang Choi, Jeong Ae Yoon, Hee Kwan Park, Geun Young Cha, Keon Woo Lee, Il Eok Kwon, Dong Kung Oh, Jong Hyun Park, Xiang Li Li, Han Soo Kim, Min Young Lim, Chang Ho Cho
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Patent number: 7553963Abstract: This invention relates to storage-stable, liquid, partially trimerized and allophanized polyisocyanates having an NCO group content of 15 to 41% by weight, and comprising 5 to 85% by weight of toluene diisocyanate, 5 to 85% by weight of a polyisocyanate of the diphenyl-methane series and an organic compound or mixture thereof. The present invention also relates to a process for the preparation of the storage-stable, liquid, partially trimerized and allophanized polyisocyanates; to storage-stable, liquid urethane prepolymers of these partially trimerized and allophanized polyisocyanates; and to a process for the production of these storage-stable, liquid, urethane prepolymers.Type: GrantFiled: October 29, 2003Date of Patent: June 30, 2009Assignee: Bayer MaterialScience LLCInventors: William E. Slack, Hersel T. Kemp, II
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Patent number: 7524435Abstract: The use of a compound comprising a nitrogenous heterocyclic group with five cyclic members including, at least two nitrogen atoms, one of the nitrogen atoms bearing a hydrogen atom to promote the opening/closing reaction of uretidione cycles in the presence of a nucleophile compound provided that, when the nitrogenous heterocyclic group is imidazole, the opening/closing reaction is not the closing reaction of the uretidione cycle in the presence of a quaternary ammonium salt.Type: GrantFiled: February 23, 2005Date of Patent: April 28, 2009Assignee: Rhodia ChimieInventor: Jean-Marie Bernard
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Patent number: 7449574Abstract: The present invention relates to a triazine based photoactive compound containing an oxime ester group. The compound according to the present invention is a photoactive compound containing both an oxime ester group and a triazine group in one molecule, has excellent radical-generating efficiency due to effective absorption of UV radiation, particularly i-line (365 nm) radiation and can function as an effective initiator for photopolymerization of various compounds containing unsaturated groups, particularly an acryl compound.Type: GrantFiled: November 6, 2006Date of Patent: November 11, 2008Assignee: LG Chem, Ltd.Inventors: Sung Hyun Kim, Jeong Ae Yoon, Raisa Kharbash, Han Soo Kim, Xiang Li Li, Min Young Lim, Chang Ho Cho
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Patent number: 7439357Abstract: A process for preparing a thiazole compound of formula (3): wherein X1 represents a hydrogen atom or a halogen atom comprising reacting a compound of formula (1): wherein X1 is as defined above, and X2 represents a halogen atom, with ammonia and formaldehyde to obtain a hexahydrotriazine compound of formula (2): wherein X1 is as defined above, and hydrolyzing the compound of formula (2).Type: GrantFiled: June 10, 2005Date of Patent: October 21, 2008Assignee: Sumitomo Chemical Company, LimitedInventors: Naoyuki Takano, Shinzo Seko, Kazuyuki Tanaka
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Patent number: 7317112Abstract: A method of dimerizing isocyanates using sulphonamide anions as a dimerization catalyst for the isocyanates and also to a process for preparing oligomeric isocyanates using such catalysts.Type: GrantFiled: August 4, 2004Date of Patent: January 8, 2008Assignee: Bayer MaterialScience AGInventors: Jürgen Köcher, Hans-Josef Laas
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Patent number: 7205374Abstract: A method of preparing an adhesive, the method comprising combining an isocyanate, a polyhydroxyl phenol-containing compound, a polyol, and a trimerization catalyst.Type: GrantFiled: October 10, 2003Date of Patent: April 17, 2007Assignee: BFS Diversified Products, LLCInventors: John W. Fieldhouse, Joseph J. Kalwara, Edward G. Kane, John B. Letts
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Patent number: 7091341Abstract: A method is described of preparing (poly)isocyanurate polyisocyanates by catalytic cyclotrimerization of isocyanates. A catalytic system is used which includes a cyclotrimerization catalyst based on a quatemary ammonium salt and imidazole as a cocatalyst.Type: GrantFiled: August 14, 2003Date of Patent: August 15, 2006Assignee: Rhodia ChimieInventors: Denis Revelant, Jean-Marie Bernard
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Patent number: 7060817Abstract: The present invention relates to the use of sulphonamide salts as catalysts for oligomerizing isocyanates and also to a process for NCO oligomerization using the catalysts of the invention.Type: GrantFiled: August 4, 2004Date of Patent: June 13, 2006Assignee: Bayer MaterialScience AGInventors: Jürgen Köcher, Reinhard Halpaap
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Patent number: 7001973Abstract: A low-viscosity polyisocyanate of reduced color, containing isocyanurate groups is prepared by partially trimerizing an aliphatic and/or cycloaliphatic diisocyanate in the presence of 0.02 to 2% weight, based on the weight of the diisocyanate starting material, of at least one trimerization catalyst containing a quarternary amine component and then removing excess diisocyanate from the reaction medium.Type: GrantFiled: March 26, 2003Date of Patent: February 21, 2006Assignee: Degussa AGInventors: Stephan Kohlstruk, Ingo Bockhoff, Michael Ewald, Rainer Lomoelder
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Patent number: 6992186Abstract: The invention relates to a novel process for preparing low-monomer-content trimers based on 2,4- and/or 2,6-diisocyanatotoluene (TDI). A catalytic trimerization is carried out in a mixture of from 20 to 80% by weight of a diisocyanate component containing at least 80% by weight of 2,4- and/or 2,6-diisocyanatotoluene, from 20 to 80% by weight of solvent, and 0–20% by weight of an alcohol component, and also phenolic catalysts containing dialkylamino-methyl groups. In the course of ongoing trimerization, in one or more steps, additional monomeric 2,v4-diisocyanatotoluene is metered in.Type: GrantFiled: June 30, 2003Date of Patent: January 31, 2006Assignee: Bayer AktiengesellschaftInventors: Martin Brahm, Oswald Wilmes, Joachim Simon
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Patent number: 6936678Abstract: The invention relates to a novel process for preparing low-monomer-content trimers based on 2,4- and 2,6-diisocyanatotoluene (TDI) and to the use thereof in coatings. The trimers are produced from a mixture of from 20 to 80% by weight of diisocyanate component containing at least 80% by weight of 2,4- and/or 2,6-diisocyanatotoluene and from 20 to 80% by weight of solvents and/or diluents and also phenolic catalysts containing dialkylaminomethyl groups.Type: GrantFiled: June 30, 2003Date of Patent: August 30, 2005Assignee: Bayer AktiengesellschaftInventors: Martin Brahm, Joachim Simon, Oswald Wilmes, Jürgen Walloschek
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Patent number: 6875243Abstract: Catalysts and processes for preparing polyisocyanates containing isocyanurate groups, and their use, wherein the catalysts are represented by the following formula (1): [Hl?Xm?Fn?]p·[R(4?q)Si(NR1R2)q]r??(I), wherein n=m+l with 1?m/n>0, and l?0, p>0 and r>0, and the ratio p/r is any value, q=1 or 2, and R, R1, R2 and X are as defined.Type: GrantFiled: November 27, 2002Date of Patent: April 5, 2005Assignee: Degussa AGInventors: Michael Ewald, Manuela Windmueller, Waltraud Poersch, Stephan Kohlstruk
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Publication number: 20040204585Abstract: It has been now surprisingly discovered after extensive research that 2-halo-4,6-bisaryl-1,3,5-triazine can be prepared with unprecedented selectivity, efficiency, mild conditions, and in high yield by the reaction of cyanuric halide with aromatics in the presence of at least one Lewis acid and at least one reaction promoter. This reaction is also unprecedently general as a variety of aromatics can be used to produce a wide selection of 2-halo-4,6-bisaryl-1,3,5-triazines. The novel approach includes the use of the reaction promoters in combination with at least one Lewis acid under certain reaction conditions to promote the formation of 2-halo-4,6-bisaryl-1,3,5-triazine compounds from cyanuric halide. Preferably, the Lewis acids and reaction promoters are combined to form a complex. 2-Halo-4,6-bisaryl-1,3,5-triazines are key intermediates for making 2-(2-oxyaryl)-4,6-bisaryl-1,3,5-triazine class of UV absorbers.Type: ApplicationFiled: April 30, 2004Publication date: October 14, 2004Inventors: Ram B. Gupta, Dennis J. Jakiela, Sampath Venimadhavan, Russell C. Cappadona, Venkatrao K. Pai
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Patent number: 6800721Abstract: The unsaturated oligophenol cyanates of the general formula [A—]n[B—A—]xB[—A]m (I) in which A is a group of formula: and B is a group of formula: where R1, R2 and R3 are each hydrogen or a bond with a group B, there being either one or two bonds with group B; and both R4 and R4′ as well as R5 and R5′ separately or jointly represent a direct bond or hydrogen and a bond with a group A, there being either one or two bonds with A. The indices m and n are 0 or 1 but not both 1 at the same time and x is a whole number between 0 and 10, where at least one of the numbers, m, n and x is not 0. The unsaturated oligophenol cyanates can be prepared by reacting the corresponding oligophenols with cyanogen chloride. The have a low viscosity and owing to their double bonds are able to undergo free-radical polymerization.Type: GrantFiled: February 9, 2001Date of Patent: October 5, 2004Assignee: Lonza AGInventors: Ulrich Daum, Alessandro Falchetto
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Patent number: 6797739Abstract: The preset invention relates to a photosensitive composition, and provides a triazine-based compound comprising new functionalized alkylthio groups of which long term storage characteristics at room temperature as well as photochemical activity as a photopolymerization initiator are superior.Type: GrantFiled: September 27, 2002Date of Patent: September 28, 2004Assignee: LG Chemical Co., Ltd.Inventors: Sung-Hyun Kim, Chul-Woo Lee, Jin-Seuk Kim, Jae-Hwan Lee, Dong-Chang Choi, Hyuk-Jin Cha
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Patent number: 6765111Abstract: The present invention is directed to a process for the production of polyisocyanates containing isocyanurate groups by trimerizing a portion of the isocyanate groups of hexamethylene diisocyanate using N,N,N-trialkyl-N-benzyl-quaternary ammonium hydroxides as the trimerization catalyst, terminating the trimerization reaction at the desired degree of trimerization by adding a catalyst poison and/or by thermally deactivating the catalyst and removing unreacted hexamethylene diisocyanate to a residual content of at most 0.2% by weight, characterized in that a) the hexamethylene diisocyanate used as starting material is freed from carbon dioxide to a residual content of less than 20 ppm (weight) and b) the catalyst is used in a quantity of less than about 0.03% by weight, based on the weight of the hexamethylene diisocyanate used.Type: GrantFiled: January 16, 1997Date of Patent: July 20, 2004Assignee: Bayer AktiengesellschaftInventors: Josef Pedain, Manfred Bock, Carl-Gerd Dieris
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Patent number: 6703471Abstract: Low-odor, storage-stable monomer-containing polyisocyanurate is prepared from isophorone diisocyanate by conducting a partial trimerization for 3 minutes to 3 hours in the presence of 0.05-2% by weight of a catalyst, based on the weight of the diisocyanate, the catalyst having the formula [R—NX3]m⊕mY⊖ wherein Y⊖ is a carboxylic acid anion of 4-8 carbons, R is a &bgr;-hydroxyalkyl group of 2-6 carbons, X is an alkylene group of 2-3 carbons and m is a number from 1.0 to 2.0. The three radicals X form a ring with the quaternary nitrogen by way of a common nitrogen atom, which may be partly &bgr;-hydroxyalkylated, said ring optionally having an OH group positioned &agr;, &bgr; or &ggr; to the nitrogen. The reaction proceeds at a temperature of 0-160° C.Type: GrantFiled: June 27, 2002Date of Patent: March 9, 2004Assignee: Degussa AGInventors: Stephan Kohlstruk, Manfred Kreczinski, Rainer Lomölder
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Publication number: 20040024213Abstract: The invention relates to a novel process for preparing low-monomer-content trimers based on 2,4- and 2,6-diisocyanatotoluene (TDI) and to the use thereof in coatings. The trimers are produced from a mixture of from 20 to 80% by weight of diisocyanate component containing at least 80% by weight of 2,4- and/or 2,6-diisocyanatotoluene and from 20 to 80% by weight of solvents and/or diluents and also phenolic catalysts containing dialkylaminomethyl groups.Type: ApplicationFiled: June 30, 2003Publication date: February 5, 2004Inventors: Martin Brahm, Joachim Simon, Oswald Wilmes, Jurgen Walloschek
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Publication number: 20040024212Abstract: The invention concerns a method for catalytic (cyclo)condensation of monomer isocyanates, characterised in that it comprises: a) reacting starting monomer isocyanates with a catalyst comprising a mineral or organic salt of a compound of formula (I), wherein Y− is selected among: a negatively charged oxygen atom, and a carbonaceous radical comprising a negative charge borne by an atom of column VB of the periodic table or by an oxygen atom advantageously by a nitrogen atom and whereof the bond with the silicon of formula (I) is borne by an atom of column VB of the periodic table, advantageously by a nitrogen atom; wherein R1, R2 and R3, identical or different, represent a monovalent hydrocarbon radical having advantageously 1 to 30 carbon atoms, or a precursor of said compound, at a temperature of at least 20° C. and advantageously of at least 40° C. and not more than 200° C., advantageously not more than 150° C.Type: ApplicationFiled: June 12, 2003Publication date: February 5, 2004Inventors: Jean-Marie Bernard, Damien Bonneau, Marc Visseau
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Publication number: 20040006228Abstract: The invention relates to a novel process for preparing low-monomer-content trimers based on 2,4- and/or 2,6-diisocyanatotoluene (TDI). A catalytic trimerization is carried out in a mixture of from 20 to 80% by weight of a diisocyanate component containing at least 80% by weight of 2,4- and/or 2,6-diisocyanatotoluene, from 20 to 80% by weight of solvent, and 0-20% by weight of an alcohol component, and also phenolic catalysts containing dialkylamino-methyl groups. In the course of ongoing trimerization, in one or more steps, additional monomeric 2,v4-diisocyanatotoluene is metered in.Type: ApplicationFiled: June 30, 2003Publication date: January 8, 2004Inventors: Martin Brahm, Oswald Wilmes, Joachim Simon
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Patent number: 6653432Abstract: The invention concerns a (cyclo)trimerisation method for isocyanates having at least two isocyanate functions, characterised in that it comprises: a) reacting initial isocyanate monomers having at least two isocyanate functions, optionally in the presence of other monomers reactive with the isocyanate monomers having at least two isocyanate functions at a temperature of at least 20° C., advantageously at least 50° C., and lower than 200° C., advantageously lower than 150° C., in the presence of a compound comprising at least one rare earth alcoholate function; b) stopping the reaction by inactivating the catalyst or its derivative forms in the reaction medium at a transformation rate of at least 2.5% and at most 90% of the initial isocyanate functions; and optionally c) distilling the reaction medium to eliminate the unreacted monomers.Type: GrantFiled: June 18, 2002Date of Patent: November 25, 2003Assignee: Rhodia ChimieInventors: Frédéric Dallemer, Jean-Marie Bernard, Denis Revelant, Frédéric Leising
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Patent number: 6642382Abstract: The invention concerns a method for cyclotrimerization of isocyanate functions by action of a catalyst based on quaternary ammonium or phosphonium. The invention is characterised in that said isocyanate functions are branched and said onium ions are selected among those whereof the total amount of carbons is not more than 30 and not less than 12; and whereof the counterion is selected among the anions corresponding to weak acids whereof the pKA is not less than 8, preferably not less than 10, more preferably not less than 12, whereof the substituents are aliphatic compounds and do not have an unsaturation in beta; and said onium ions comprise at least 2 radicals of more than 6, advantageously more than 10, preferably more than 12 carbon atoms.Type: GrantFiled: November 12, 2002Date of Patent: November 4, 2003Assignee: Rhodia ChimieInventors: Jean-Marie Bernard, Frédéric Dallemer, Denis Revelant