Nitrogen-containing Reactant Is A Heterocyclic Ring Compound Containing At Least One Nitrogen Atom As A Ring Member Or Is Nitrogen-containing Aromatic Compound Patents (Class 528/163)
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Patent number: 9698377Abstract: A copolymer according to the present disclosure is provided, which includes 30 to 80 mol % of a repeating unit represented by formula (I), 5 to 25 mol % of a repeating unit represented by formula (II), and 5 to 30 mol % of a repeating unit represented by formula (III): wherein R1 is C6-C13 aryl group, C7-C13 aralkyl group, C6-C8 halogenated aryl group or C7-C8 aryloxyalkyl group; R3 is C3-C16 alkyl group or C3-C6 alkoxy substituted alkyl group; R5 is a single bond or C1-C3 alkylene group, R6 and R7 are independently C1-C3 alkoxy group, R8 is polysiloxane with methyl and phenyl groups; and R2, R4 and R9 are independently hydrogen or methyl. In addition, a resin composition, a packaging film and a package structure including the same are provided.Type: GrantFiled: December 21, 2016Date of Patent: July 4, 2017Assignee: INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTEInventors: Ming-Tzung Wu, Te-Yi Chang, Yao-Jheng Huang, Yun-Yu Lai
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Patent number: 9012122Abstract: A modified novolak phenolic resin is obtained by reacting a novolak phenolic resin containing at least 50 wt % of p-cresol with a crosslinker. This method increases the molecular weight of the existing novolak phenolic resin containing at least 50 wt % of p-cresol to such a level that the resulting modified novolak phenolic resin has heat resistance enough for the photoresist application.Type: GrantFiled: October 24, 2012Date of Patent: April 21, 2015Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Yoshinori Hirano, Hideyoshi Yanagisawa
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Patent number: 9000120Abstract: Epoxy adhesive compositions contain a heat-activatable catalyst. The heat-activatable catalyst includes a tertiary amine catalyst and a novolac resin that has a weight average molecular weight of at least 3000. One-component epoxy adhesive formulations that contain the heat-activatable catalyst have unexpectedly good storage stability.Type: GrantFiled: June 27, 2011Date of Patent: April 7, 2015Assignee: Dow Global Technologies LLCInventors: Ming Ming, Shaoguang Feng, Yan Fei Liu, Andreas Lutz, Robert D. Froese, Glenn G. Eagle, Gary L. Jialanella, Eric E. Cole, Michael R. Golden
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Patent number: 8975359Abstract: The present invention relates to polymers comprising one or more (repeating) unit(s) of the formula (I), and at least one (repeating) unit(s) which is selected from repeating units of the formula (II), (III) and (IV); and polymers of the formula III, or IV and their use as organic semiconductor in organic devices, especially in organic photovoltaics (solar cells) and photodiodes, or in a device containing a diode and/or an organic field effect transistor. The polymers according to the invention have excellent solubility in organic solvents and excellent film-forming properties. In addition, high efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when the polymers according to the invention are used in organic field effect transistors, organic photovoltaics (solar cells) and photodiodes.Type: GrantFiled: October 21, 2009Date of Patent: March 10, 2015Assignee: BASF SEInventors: Mathias Düggeli, Mahmoud Zaher Eteish, Pascal Hayoz, Olivier Frédéric Aebischer, Marta Fonrodona Turon, Mathieu G. R. Turbiez
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Patent number: 8946376Abstract: The present invention relates to 1,4-diketopyrrolo[3,4-c]pyrrole (DPP) derivatives of the below formula to their manufacture; to their use as organic semiconductors, e.g. in semiconductor devices, especially a sensor, a diode, a photodiode, an organic field effect transistor, a transistor for flexible displays, and/or a solar cell (photovoltaic cell); to such semiconductor devices comprising diketopyrrolopyrrol derivatives of the formula I as a semiconducting effective means, and to devices containing said semiconductor devices. The compounds of the formula I have excellent solubility in organic solvents. High efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when said compounds are used in semiconductor devices or organic photovoltaic (PV) devices.Type: GrantFiled: September 27, 2011Date of Patent: February 3, 2015Assignee: BASF SEInventors: Frank Würthner, Sabin-Lucian Suraru, Pascal Hayoz
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Patent number: 8921506Abstract: A copolymer includes a first unit and at least two units different from the first unit. An organic solar cell includes a first electrode, a second electrode opposite the first electrode, and one or more organic material layers interposed between the first electrode and the second electrode and including a photoactive layer, and one or more of the organic material layers include the copolymer. A method for fabricating an organic solar cell includes preparing a substrate, forming a first electrode on a region of rear sides of the substrate, forming on the first electrode an organic material layer containing the copolymer, and forming a second electrode on the organic material layer.Type: GrantFiled: August 3, 2012Date of Patent: December 30, 2014Assignee: LG Chem, Ltd.Inventors: Taiho Park, Gang-Young Lee, Minjeong Im, Seulki Song, Jinseck Kim, Jaechol Lee, Hangken Lee, Songrim Jang, Keun Cho
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Patent number: 8865861Abstract: A Pechmann dye based polymer of formula 1, below, is provided.Type: GrantFiled: December 27, 2012Date of Patent: October 21, 2014Assignee: Xerox CorporationInventors: Anthony J. Wigglesworth, Yiliang Wu, Ping Liu
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Patent number: 8853349Abstract: Conjugated polymers and small molecules including the nonplanar aromatic 1,6-methano[10]annulene ring structure along with aromatic subunits, such as diketopyrrolopyrrole, and 2,1,3-benzothiadiazole, substituted with alkyl chains in a “Tail In,” “Tail Out,” or “No Tail” regiochemistry are disclosed.Type: GrantFiled: December 14, 2012Date of Patent: October 7, 2014Inventors: John D. Tovar, Benjamin C. Streifel, Patricia A. Peart
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Patent number: 8809484Abstract: An extended isoindigo polymer of Formula (I), below, is provided.Type: GrantFiled: December 27, 2012Date of Patent: August 19, 2014Assignee: Xerox CorporationInventors: Anthony J. Wigglesworth, Yiliang Wu
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Patent number: 8691931Abstract: Polymers which can be used in p-type materials for organic electronic devices and photovoltaic cells. Compounds, monomers, dimers, trimers, and polymers comprising: wherein A1 and A2 each independently comprise a fused ring system comprising at least two fused rings directly covalently linked to the pyrrole rings. Good photovoltaic efficiency and lifetime can be achieved. The R group can provide solubility, environmental stability, and fine tuning of spectroscopic and/or electronic properties. Different polymer microstructures can be prepared which encourage multiple band gaps and broad and strong absorptions. The carbonyl can interact with adjacent thiophene rings to provide backbone with rigidity, induce planarity, and reduce and/or eliminate intramolecular chain twisting defects.Type: GrantFiled: September 1, 2010Date of Patent: April 8, 2014Assignee: Plextronics, Inc.Inventors: Christopher T. Brown, Christophe René Gaston Grenier, Chad Landis, Elena E. Sheina, Ting Xu
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Patent number: 8691930Abstract: A polymer represented by Formula 1 below: wherein functional groups and n are defined as in the specification.Type: GrantFiled: March 30, 2011Date of Patent: April 8, 2014Assignee: Samsung Display Co., Ltd.Inventors: Jae-Yong Lee, Hee-Yeon Kim, Seung-Gak Yang, Yoon-Hyun Kwak, Jeoung-In Yi
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Patent number: 8598299Abstract: A semiconductor composition for producing a semiconducting layer with consistently high mobility is disclosed. The semiconductor composition includes a diketopyrrolopyrrole-thiophene copolymer and a non-aromatic halogenated hydrocarbon solvent. The copolymer has a structure disclosed within. Preferably, the non-aromatic halogenated hydrocarbon solvent contains at least 2 carbon atoms and at least 3 halogen atoms.Type: GrantFiled: December 6, 2011Date of Patent: December 3, 2013Assignee: Xerox CorporationInventors: Yiliang Wu, Anthony James Wigglesworth, Ping Liu
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Patent number: 8476397Abstract: A polymer compound comprising a residue of a compound represented by the following formula (0): wherein Ar0 represents a substituent such as a hydrogen atom, an alkyl group, an alkoxy group, an aryl group and the like, or a group represented by the following formula (A), at least two Ar0s are groups represented by the following formula (A), R0 represents a substituent such as an alkyl group, an alkoxy group, an aryl group and the like, l and m represent an integer of 0 to 3, wherein A0 represents —N? or —C(R2)?. R2 represents a substituent such as a hydrogen atom, an alkyl group, an alkoxy group, an aryl group and the like.Type: GrantFiled: June 26, 2009Date of Patent: July 2, 2013Assignee: Sumitomo Chemical Company, LimitedInventor: Satoshi Kobayashi
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Patent number: 8309066Abstract: Cationic benzoxazine (co)polymers wherein at least 5% of all nitrogen atoms are in the form of quaternary nitrogen atoms, and to a method for producing said polymers. The invention also relates to a washing and cleaning agent, a textile treatment agent or a cosmetic agent containing at least one cationic benzoxazine (co)polymer according to the invention.Type: GrantFiled: November 9, 2011Date of Patent: November 13, 2012Assignee: Henkel AG & Co. KGaAInventors: Andreas Taden, Stefan Kreiling, Rainer Schoenfeld, Paula Barreleiro, Thomas Eiting
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Patent number: 8288504Abstract: The present invention is directed to a method for preparing a cyclic guanidine comprising reacting (i) a cyanamide, (ii) a polyamine, and (iii) a weak acid. The present invention is also directed to a coating composition comprising the cyclic guanidine.Type: GrantFiled: March 10, 2010Date of Patent: October 16, 2012Assignee: PPG Industries Ohio, Inc.Inventors: Steven R. Zawacky, Charles R. Hickenboth, Richard F. Karabin, Gregory J. McCollum, Thomas C. Moriarity
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Patent number: 8158744Abstract: A polymer of Formula (I) wherein R1, R2, Ar1, Ar2, and n are as described herein. The polymer may be used in a semiconducting layer of an electronic device.Type: GrantFiled: March 1, 2011Date of Patent: April 17, 2012Assignee: Xerox CorporationInventors: Yiliang Wu, Ping Liu, Anthony James Wigglesworth, Nan-Xing Hu
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Publication number: 20120058069Abstract: Cationic benzoxazine (co)polymers wherein at least 5% of all nitrogen atoms are in the form of quaternary nitrogen atoms, and to a method for producing said polymers. The invention also relates to a washing and cleaning agent, a textile treatment agent or a cosmetic agent containing at least one cationic benzoxazine (co)polymer according to the invention.Type: ApplicationFiled: November 9, 2011Publication date: March 8, 2012Inventors: Andreas Taden, Stefan Kreiling, Rainer Schoenfeld, Paula Barreleiro, Thomas Eiting
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Publication number: 20120047664Abstract: The invention relates to washing and cleaning agents for washing or cleaning colored textile surface structures, used for improving the color-fastness thereof. The aim was substantially met by adding polymers obtained by the polymerization of benzoxazine monomers to the agent.Type: ApplicationFiled: November 9, 2011Publication date: March 1, 2012Applicant: Henkel AG & Co. KGaAInventors: Paula Barreleiro, Thomas Eiting, Andreas Taden, Siglinde Erpenbach
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Publication number: 20120046424Abstract: Compositions and methods for forming condensates and resin compositions are provided. In one embodiment, a condensate is formed from a reaction mixture including a triazine monomer, an arylhydroxy monomer, an aldehyde monomer and an acid catalyst having a pKa value of greater than 3.8. The condensates contain up to 28 wt. % of nitrogen and have a melt viscosity of 3,000 cps or less at 175° C. The condensates may have a solubility of at least 80 wt. % solids dissolved in an organic solvent for 120 hours or greater. Also disclosed are methods for the manufacture of the condensate as well as the condensate's use in fire-retardant epoxy resin compositions suitable for the manufacture of laminates for electronic applications. There is also disclosed a glycidylated triazine-arylhydroxy-aldehyde condensate of this invention.Type: ApplicationFiled: August 17, 2010Publication date: February 23, 2012Inventors: Ganapathy S. Viswanathan, Raman C. Subrayan, Vinay Malhotra
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Publication number: 20110306735Abstract: The invention relates to a hydroxy-aromatic resin, prepared by bringing together and letting react a hydroxy-aromatic compound of formula (I) and an alkanol hemiacetal compound of formula (II). Formula (I) is: wherein R1, R2, R3, R4 and R5 may be the same or may be different and are H, OH, a C1-C20 alkyl group, or an oligomeric or polymeric system, whereby at least one of the set consisting of R1, R3, and R5 is H, Formula (II) is: wherein R6 is a C1-C12 alkyl group, aryl group, aralkyl group or cycloalkyl group and wherein R12 is H, a C1-C12 alkyl group, aryl group, aralkyl group or cycloalkyl group. The invention further relates to use of the resin in adhesives, laminates, and coatings.Type: ApplicationFiled: August 24, 2011Publication date: December 15, 2011Applicant: DSM IP Assets B.V.Inventor: Rudolfus Antonius Theodorus Maria VAN BENTHEM
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Patent number: 7932344Abstract: A polymer has a structure represented by: wherein each R is independently selected from hydrogen, an optionally substituted hydrocarbon, and a hetero-containing group, each M is conjugated moiety selected from: and substituted derivatives and combinations thereof, a represents a number that is at least 1; b represents a number from 1 to 20; n represents a number from 2 to 500 a represents a number that is at least 1, b represents a number from 0 to 20, n represents a number from 2 to 5000, each X is independently selected from S, Se, 0, and NR?, where each R? is independently selected from hydrogen, an optionally substituted hydrocarbon, and a hetero-containing group, each Z is independently one of an optionally substituted hydrocarbon, a hetero-containing group, and a halogen, d represents a number which is at least 1, and e represents a number from zero to 2.Type: GrantFiled: September 6, 2007Date of Patent: April 26, 2011Assignee: Xerox CorporationInventor: Yuning Li
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Patent number: 7910684Abstract: A thin film transistor device includes a semiconductor layer. The semiconductor layer includes a compound comprising a chemical structure represented by: wherein each R is independently selected from hydrogen, an optionally substituted hydrocarbon, and a hetero-containing group, each Ar is independently selected from optionally substituted aryl and heteroaryl groups, each M is an optional, conjugated moiety, a represents a number that is at least 1, b represents a number from 0 to 20, and n represents a number that is at least 1.Type: GrantFiled: September 6, 2007Date of Patent: March 22, 2011Assignee: Xerox CorporationInventor: Yuning Li
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Patent number: 6916505Abstract: A water-soluble composition including a water soluble polyamine adduct which is a reaction product of: (a) an alkoxy group modified polyepoxide resin containing an average of at least 1.5 epoxide groups per molecule; and (b) a Mannich base polyamine. The Mannich base polyamine is a reaction product of a polyamine containing at least two amino groups with a N-Mannich condensate prepared from a reaction of a phenolic compound, an aldehyde, and a secondary amine wherein the secondary amine of the N-Mannich condensate is replaced by one of the at least two amino groups of the polyamine, and wherein the ratio of the Mannich base polyamine to the alkoxy group modified polyepoxide resin contains an excess of an active amine hydrogen relative to epoxide groups so that the water soluble polyamine adduct has an amine hydrogen equivalent weight of at most 1000 based on solids content.Type: GrantFiled: March 4, 2003Date of Patent: July 12, 2005Assignee: Air Products and Chemicals, Inc.Inventors: William R. Raymond, Michael Cook
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Patent number: 6706809Abstract: Infinitely water soluble, storage stable, low molecular weight, amine-modified resins/binders (e.g., phenol-formaldehyde resole resins and binders made therefrom) are used to produce low odor fiberglass products, such as fiberglass insulation for automobile headliners and room dividers. The cured, bonded fiberglass products have low TMA (trimethylamine) emission because the free formaldehyde in the resin has been scavenged with melamine, which resists thermal decomposition, and because the binder contains a relatively low urea content, which is a TMA contributor. The resole resin production process includes adding two different formaldehyde scavengers (e.g., melamine and urea) to produce a modified phenol-formaldehyde resole resin. This resole resin is produced into a binder by mixing with water, optionally in the presence of a latent acid catalyst (e.g., an ammonium salt of a strong acid).Type: GrantFiled: November 21, 2001Date of Patent: March 16, 2004Assignee: Georgia-Pacific Resins, Inc.Inventors: Kim Tutin, W. Hayes Ingram, Mary L. Epling, Kurt D. Gabrielson, James T. Wright, Carl R. White
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Patent number: 6706845Abstract: Phenol formaldehyde resins that have low free formaldehyde when produced, that maintain their low free formaldehyde levels during storage, and that demonstrate low levels of formaldehyde emissions during processing, curing, and thereafter.Type: GrantFiled: November 21, 2001Date of Patent: March 16, 2004Assignee: Georgia-Pacific Resins, Inc.Inventors: W. Hayes Ingram, Ted M. McVay, Mary Letchas
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Patent number: 6657016Abstract: A polyester resin composition comprising 50 equivalents/ton or more of an aromatic ring in the resin and at least one thermosetting resin selected from the group consisting of melamine resin, urea resin, benzoguanamine resin and phenol resin. The aromatic ring in the polyester resin has a phenolic hydroxyl group and at least one of ortho-position and para-position of the aromatic ring to the phenolic hydroxyl group is a hydrogen atom. The resin composition has excellent toughness at ambient temperature and heat resistance.Type: GrantFiled: March 14, 2002Date of Patent: December 2, 2003Assignee: Toyo Boseki Kabushiki KaishaInventor: Takeshi Yatsuka
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Patent number: 6617029Abstract: The present invention relates to a nitrogen-containing epoxy resin of the following formula: wherein R's are the same or different and each represents a hydrogen atom or —R13—C6-10 aryl-(OR14)p, and the aryl group is optionally substituted with C1-6 alkyl group, in which R13 represents a C1-6 alkylene group or a phenylene —CH2— group optionally substituted with a hydroxy group, R14 represents a glycidyl group, and p is an integer of 1 or 2, provided that at least one R group is not a hydrogen atom; R1 represents a phenyl group or —N(R)2 group in which R is defined as above. The resin is produced from sequentially reacting melamine derivatives with aldehydes, phenolic compounds, and epihalohydrin.Type: GrantFiled: January 4, 2002Date of Patent: September 9, 2003Assignee: Chang Chun Plastics Co., Ltd.Inventors: Kuen-Yuan Hwang, Hong-Hsing Chen, Chih-Fu Chen, Huan-Chang Chao
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Patent number: 6605354Abstract: There is disclosed a triazine-phenol-aldehyde condensate which contains at least 15% of nitrogen, has a melt viscosity of not greater than 2,000 cps at 175° C. and a solubility of at least 80% by weight at 25° C. by the 90:10 methanol:water method. Also disclosed are methods for the manufacture of the condensate as well as its use in fire-retardant epoxy resin compositions suitable for the manufacture of laminates for electronic applications. Additionally, disclosed is a composition comprising a physical mixture of a triazine-phenol-aldehyde condensate with benzoguanamine and/or acetoguanamine wherein the mixture contains from about 0.5% to 20% of benzoguanamine, acetoguanamine and mixtures thereof based on the weight of the condensate. There is also disclosed a glycidylated triazine-phenol-aldehyde condensate of this invention.Type: GrantFiled: August 28, 2001Date of Patent: August 12, 2003Assignee: Borden Chemical, Inc.Inventor: Arthur H. Gerber
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Patent number: 6515047Abstract: An epoxy resin composition used for semiconductor encapsulating, laminated boards or electrical insulation is prepared from a thermosetting resin composition containing: (A) an epoxy resin and (B) a phenol resin represented by the following general formula (1): wherein R1 and R2 are a hydrogen atom or alkyl group having 1 to 4 carbon atoms, and R3 is an amino group, alkyl group having 1 to 4 carbon atoms, phenyl group, vinyl group or the like, and wherein m is an integer of 1 or 2.Type: GrantFiled: February 15, 2001Date of Patent: February 4, 2003Assignee: Resolution Performance ProductsInventors: Takao Fukuzawa, Takayoshi Hirai, Tetsuro Imura, Yoshinobu Ohnuma
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Publication number: 20020193552Abstract: The present invention provides a flame retardant phenol resin material which includes a phenol condensate, wherein a poly-aromatic compound obtained by a reaction of phenols (A) to aromatics (B) except for phenols and a heterocyclic compound (C) including nitrogen as heteroatom are condensed via aldehydes (D), and also provides a flame retardant epoxy resin material which includes an epoxy resin obtained by glycidyl-etherification of at least a part of phenolic hydroxyl groups of a poly-aromatic compound obtained by a reaction of phenols (A) to aromatics (B) except for phenols and a heterocyclic compound (C) including nitrogen as heteroatom are condensed via aldehydes (D).Type: ApplicationFiled: February 19, 2002Publication date: December 19, 2002Applicant: NEC CORPORATIONInventors: Yukihiro Kiuchi, Masatoshi Iji, Makoto Soyama
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Patent number: 6410776Abstract: The invention relates to a process for the preparation of resols by reacting phenolic compounds with aldehydes with catalysis by metal salts whose cation can easily be precipitated as low-solubility salts in industrial processes. In this process, a dispersant is added to the reaction mixture comprising phenolic compound, aldehyde and metal salt before, during or after the condensation reaction, and a complexing agent is admixed after the condensation reaction is complete and after the dispersant has been admixed. The resultant resins are transparent even after neutralization using sulphuric acid.Type: GrantFiled: October 4, 2000Date of Patent: June 25, 2002Assignee: Bakelite AGInventors: Willi Roll, Axel Bottcher, Walter Napp, Peter Fricke
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Patent number: 6392003Abstract: The present invention provides a flame retardant phenol resin material which includes a phenol condensate, wherein a poly-aromatic compound obtained by a reaction of phenols (A) to aromatics (B) except for phenols and a heterocyclic compound (C) including nitrogen as heteroatom are condensed via aldehydes (D), and also provides a flame retardant epoxy resin material which includes an epoxy resin obtained by glycidyl-etherification of at least a part of phenolic hydroxyl groups of a poly-aromatic compound obtained by a reaction of phenols (A) to aromatics (B) except for phenols and a heterocyclic compound (C) including nitrogen as heteroatom are condensed via aldehydes (D).Type: GrantFiled: December 15, 1999Date of Patent: May 21, 2002Assignee: NEC CorporationInventors: Yukihiro Kiuchi, Masatoshi Iji, Makoto Soyama
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Patent number: 6391967Abstract: This invention discloses a flame retarding thermoplastic resin composition, which is comprised of (i) a thermoplastic resin and (ii) a phenolic resin compound as a flame retardant, wherein the phenolic resin compound contains a nitrogen-containing heterocycle and phosphorus. Since the flame retarding thermoplastic resin composition of this invention does not contain halogen, and has excellent flame retardant properties and high heat resistance, it is useful in producing parts and products in the fields of electronics, electricity and automobile.Type: GrantFiled: February 11, 2000Date of Patent: May 21, 2002Assignee: Chang Chun Plastics Co., Ltd.Inventors: Kuen-Yuan Hwang, Hong-Hsing Chen, Ying-Ling Liu, Wen-Tsai Tsai
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Publication number: 20020007038Abstract: Improved anti-reflective coating compositions for use in integrated circuit manufacturing processes and methods of forming these compositions are provided. Broadly, the compositions are formed by heating a solution comprising a compound including specific compounds (e.g., alkoxy alkyl melamines, alkoxy alkyl benzoguanamines) under acidic conditions so as to polymerize the compounds and form polymers having an average molecular weight of at least about 1,000 Daltons. The monomers of the resulting polymers are joined to one another via linkage groups (e.g., —CH2—, —CH2—O—CH2—) which are bonded to nitrogen atoms on the respective monomers. The polymerized compound is mixed with a solvent and applied to a substrate surface after which it is baked to form an anti-reflective layer. The resulting layer has high k values, improved etch rates, and can be formulated for both conformal and planar applications.Type: ApplicationFiled: May 30, 2001Publication date: January 17, 2002Inventors: Rama Puligadda, Runhui Huang
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Patent number: 6031064Abstract: Condensation products obtained by condensation of(A) a mixture consisting of(a) a triazine of the general formula I ##STR1## and (b) a mixture consisting of(b1) a triazine of the general formula II ##STR2## (b2) a substituted melamine of the general formula III ##STR3## (B) phenols withformaldehyde or formaldehyde-donating compounds are useful for producing shaped articles, especially fibers and foams.Type: GrantFiled: August 28, 1998Date of Patent: February 29, 2000Assignee: BASF AktiengesellschaftInventors: Erhard Guenther, Wolfgang Reuther
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Patent number: 5952440Abstract: A curable, alkaline, melamine modified phenol-formaldehyde resin is prepared from an initial phenol-formaldehyde resole resin containing from 0.5 to 2.5 percent of free formaldehyde by scavenging formaldehyde with 1 to 12 parts of melamine for each 100 parts of the initial resin wherein the molar ratio of formaldehyde to melamine is 0.2 to 1.5 moles of formaldehyde for each mole of melamine to reduce the free formaldehyde to less than 70% of that in the initial resin and prepare a storage stable resin which contains less than 0.7% of free formaldehyde and which maintains its stability under application conditions. An ammonium salt of strong acid and additional water is incorporated in the melamine modified resin to prepare an alkaline binder. The binder is sprayed on to fiberglass with low formaldehyde emissions, good stability and rapid cure in the acid range.Type: GrantFiled: November 3, 1997Date of Patent: September 14, 1999Assignee: Borden Chemical, Inc.Inventors: Wayne R. Walisser, Calvin K. Johnson
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Patent number: 5952447Abstract: Disclosed is a phenol resin composition containing a specific triazines-modified novolak phenol resin comprising phenols, triazines and aldehydes, and a method for producing the triazines-modified novolak phenol resin comprising the steps of as a first step reaction, successively effecting processes (i), (ii) and (iii), wherein said process (i) is a process for adjusting a pH of a system of a mixture of phenols, triazines and aldehydes in a range of 5 to 10, said process (ii) is a process for reacting said mixture under the condition that the aldehydes are not volatilized and said process (iii) is a process for removing a reaction water in the system; then as a second step reaction, successively effecting said processes (ii) and (iii) at a higher temperature than that of the first step reaction; thereafter as a third step reaction, successively effecting said processes (ii) and (iii) at a higher temperature than that of the second step reaction; and further, depending upon a necessity, repeating the second stType: GrantFiled: May 8, 1998Date of Patent: September 14, 1999Assignee: Dainippon Ink and Chemicals, Inc.Inventor: Takashi Ikeda
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Patent number: 5939515Abstract: Condensation of products obtained by condensation of a mixture comprising(A) from 90 to 99.9 mol % of a mixture consisting essentially of(a) from 30 to 100 mol % of melamine and(b) from 0 to 70 mol % of a substituted melamine of the formula I ##STR1## where X, X' and X" are as defined in the specification, or mixtures of melamines I, and(c) from 1 to 70 mol %, based on (a)+(b), of a substituted triazine of the formula II ##STR2## where R", Z' and Z" are as defined in the specification, or mixtures of triazines II, and(B) from 0.1 to 10 mol %, based on (A) (a), (A) (b) and (B), of phenols which are unsubstituted or are substituted by radicals selected from the group consisting of C.sub.1 -C.sub.9 -alkyl and hydroxyl, C.sub.1 -C.sub.4 -alkanes substituted by two or three phenol groups, di(hydroxyphenyl)sulfones or mixtures of these phenols,withformaldehyde or formaldehyde-supplying compounds in a molar ratio of melamine, substituted melamine I and triazine II to formaldehyde within the range from 1:1.15 to 1:4.Type: GrantFiled: January 29, 1998Date of Patent: August 17, 1999Assignee: BASF AktiengesellschaftInventors: Erhard Guenther, Wolfgang Reuther
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Patent number: 5916999Abstract: A process for producing continuous filament fibers from a hydroxy- or amino-alkyl-melamine modified melamine-formaldehyde condensation product comprises filtering the highly concentrated aqueous solution of the melamine-formaldehyde condensation product, forcing the filtrate through a spinneret, drying the extruded filaments in a drying shaft by means of hot air, and treating the dried filaments in a tempering oven at temperatures which rise gradually to a maximum temperature of from 160 to 250.degree. C. to cure the precondensate.Type: GrantFiled: October 9, 1997Date of Patent: June 29, 1999Assignee: BASF AktiengesellschaftInventors: Heinz Berbner, Hartmut Gihr, Uwe Rachwalsky, Hans Dieter Zettler
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Patent number: 5916966Abstract: Disclosed is a stabilized phenolic resin melamine dispersion comprising a liquid alkaline resole resin composition and solid melamine crystal dispersed throughout the resin composition. The liquid alkaline resole resin composition comprises the reaction product of combining formaldehyde and phenol at a formaldehyde to phenol mole ratio of about 0.5:1 to about 3.5:1 in the presence of a basic catalyst. The melamine crystal to phenol mole ratio ranges from about 0.01:1 to about 1:1. Moreover, the composition has a free formaldehyde content of at most about 0.5 weight percent. A method for making this dispersion is also disclosed.Type: GrantFiled: August 28, 1996Date of Patent: June 29, 1999Assignee: Borden Chemical, Inc.Inventor: Wayne Richard Walisser
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Patent number: 5763558Abstract: A process for hardening a composition and a hardenable composition, in wh there are used:at least one novolac resin;at least one hardener of the resin, selected from the group consisting of substituted melamines;at least one compound comprising at least one ##STR1## group, this compound being without methylol group and ether group corresponding to methylol, and/or at least one reagent capable of giving such a compound under the conditions of the hardening.The hardening of the resin is caused by the action of heat.Type: GrantFiled: June 11, 1996Date of Patent: June 9, 1998Assignee: Compagnie Generale Des Etablissements Michelin-Michelin & CieInventors: Brigitte Marie Chauvin, Olivier Durel
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Patent number: 5708121Abstract: This invention relates to an emulsifiable melamine-modified phenolic resole resin composition useful as a binder for glass fibers. The invention is more particularly directed to the process of preparing the resole resin composition using an alkaline condensation in the presence of a polyhydroxyl compound.Type: GrantFiled: March 7, 1997Date of Patent: January 13, 1998Assignee: Georgia-Pacific Resins, Inc.Inventors: Claude Phillip Parks, Kurt Forrest Anderson
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Patent number: 5684114Abstract: A two-part adhesive is provided wherein the first part comprises a stable aqueous alkaline monohydroxylic phenolic resole resin solution containing a methylene donor such as oxazolidine or a methylolurea and the second part comprises a stable resorcinolic resin precondensate having a shortage of formaldehyde and optionally containing a catalyst such as an ester functional compound for the resole resin. The resin in each part exhibits viscosity stability of an unmodified resin until mixed with the other part wherein the methylene donor, of the first part catalyzes the resorcinolic resin of the second part and the catalyst, when used, of the second part catalyzes the monohydroxylic phenolic resole resin of the first part. The adhesive finds utility in the production of structural lignocellulosic panels.Type: GrantFiled: June 7, 1995Date of Patent: November 4, 1997Assignee: Borden Chemical, Inc.Inventors: Earl K. Phillips, William D. Detlefsen, Fred E. Carlson
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Patent number: 5681916Abstract: Urea-modified, highly reactive phenolic resins useful as center-layer bonding agents in the manufacture of particleboard are provided by condensing phenol and formaldehyde until shortly before gelation takes place such that, after addition of urea, relatively low-alkaline, urea-modified phenolic resins are obtained which my optionally be stored and to which, shortly before processing them into glues for center-layer particles, alkali is added in sufficient quantities to ensure rapid cross-linking of the phenolic resin.Type: GrantFiled: June 29, 1995Date of Patent: October 28, 1997Assignee: RWE-DEA Aktiengesellschaft fur Mineraloel und ChemieInventors: Adolf Buschfeld, Matthias Lattekamp, Manfred Gramse, Hans-Jurgen Krezmin
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Patent number: 5629083Abstract: A process for the production of modified phenol-aldehyde resins includes the use of a modifier selected from melamine, urea, and other suitable nonvolatile organic compounds. The phenolic component of the resins preferably includes a difunctional phenolic compound. The inventive resins resist precuring and are particularly useful in blowline blending procedures.Type: GrantFiled: June 7, 1995Date of Patent: May 13, 1997Assignee: Masonite CorporationInventor: Zygmunt Teodorczyk
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Patent number: 5623032Abstract: A process for preparing ashless and low-ash phenolic resole resins having no amine odor, and a process for preparing storage-stable mixtures or premix solutions of phenol-formaldehyde resin and urea or unrea-formaldehyde resins. These processes react phenol and formaldehyde in the presence of an effective catalytic amount of a low-volatile and strongly basic tertiary amino alcohol either alone or in combination with an inorganic base.Type: GrantFiled: June 23, 1995Date of Patent: April 22, 1997Assignee: Angus Chemical CompanyInventor: Gaoming Wu
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Patent number: 5621052Abstract: Novel aminoplast anchored UV stabilizers are provided. Compared to unanchored stabilizers, the anchored stabilizers disclosed herein have increased compatibility with coating resins and have reduced volatility due to higher molecular weights resulting from anchoring. A process for preparing the anchored stabilizers by the reaction of unanchored stabilizers with alkoxymethylated aminoplasts in a sulfuric acid medium is also provided. The unanchored stabilizers include 2-(2-hydroxyaryl)benzotriazoles, 2-hydroxybenzophenones, 2-(2-hydroxyaryl)-4,6-diaryl-1,3,5-triazines, salicylic acid derivatives, 2-hydroxyoxanilides, and blocked derivatives thereof as well as mixtures of two or more stabilizers. The aminoplasts include alkoxymethylated derivatives of glycolurils, melamines, and benzoguanamines.Type: GrantFiled: December 29, 1992Date of Patent: April 15, 1997Assignee: Cytec Technology Corp.Inventors: Jeno G. Szita, Paul S. Waterman
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Patent number: 5605986Abstract: Novel aminoplast anchored UV stabilizers are provided. Compared to unanchored stabilizers, the anchored stabilizers disclosed herein have increased compatibility with coating resins and have reduced volatility due to higher molecular weights resulting from anchoring. A process for preparing the anchored stabilizers by the reaction of unanchored stabilizers with alkoxymethylated aminoplasts in a sulfuric acid medium is also provided. The unanchored stabilizers include 2-(2-hydroxyaryl)benzotriazoles, 2-hydroxybenzophenones, 2-(2-hydroxyaryl)-4,6-diaryl-1,3,5-triazines, salicylic acid derivatives, 2-hydroxyoxanilides, and blocked derivatives thereof as well as mixtures of two or more stabilizers. The aminoplasts include alkoxymethylated derivatives of glycolurils, melamines, and benzoguanamines.Type: GrantFiled: May 23, 1995Date of Patent: February 25, 1997Assignee: Cytec Technology Corp.Inventors: Jeno G. Szita, Paul S. Waterman
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Patent number: 5530031Abstract: Water-insoluble condensation products, obtained by the condensation of a mixture containing as essential components(A) from 80 to 99.9 mol %, based on the sum of (A), (B) and (C), of a mixture consisting essentially of(a) from 30 to 99 mol % of melamine and(b) from 1 to 70 mol % of a substituted melamine of the formula I ##STR1## where X, X' and X" are each selected from the group consisting of --NH.sub.2, --NHR and --NRR', and X, X' and X" are not all --NH.sub.2 at one and the same time, and R and R' are each selected from the group consisting of hydroxy-C.sub.2 -C.sub.10 -alkyl, hydroxy-C.sub.2 -C.sub.4 -alkyl-(oxa-C.sub.2 -C.sub.4 -alkyl).sub.n, where n is from 1 to 5, and amino-C.sub.2 -C.sub.12 -alkyl, or mixtures of melamines I,(B) from 0.Type: GrantFiled: September 9, 1994Date of Patent: June 25, 1996Assignee: BASF AktiengesellschaftInventors: Erhard Guenther, Wolfgang Reuther, Uwe Kirchgassner
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Patent number: 5368803Abstract: A fibrous resinated panel is provided which when used in a closed environment releases relatively minor amounts of trimethylamines, aldehydes and phenolic compounds into the closed environment. The panel is formed by compressing a fibrous mat impregnated with a thermosetting resin system in a mold cavity defined between an upper and a lower inner mold surface at a temperature between 400.degree. to 600.degree. for 45 to 90 seconds whereby the thermosetting resin is substantially cured and the mat is shaped to conform to a desired contour prior to removing the mat from the mold cavity. The thermosetting resin system used to impregnate the mat includes an essentially aqueous A-stage form resole-melamine composition containing residues of free melamine(s) to free aldehyde(s) to free phenolic compound(s) in a molar equivalent ratio ranging from about 0.2:1.5:1 to about 0.8:3.5:1.Type: GrantFiled: February 12, 1993Date of Patent: November 29, 1994Assignee: United Technologies Automotive, Inc.Inventors: Mark J. Brow, Ronald P. Pitsch