Plural Benzene Rings Bonded Directly To Isocyanate Groups (e.g., Diisocyanatodiphenylmethane, Etc.) Patents (Class 560/359)
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Patent number: 5258548Abstract: A method for preventing coloration of an aromatic isocyanate compound, which is characterized in that an organic phosphite ester of formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are, the same or different, each a C.sub.4-20 hydrocarbon group, 2,6-di-tert.-butyl-4-methylphenol and triphenyl phosphite are added to the aromatic isocyanate compound.Type: GrantFiled: September 3, 1992Date of Patent: November 2, 1993Assignee: Sumitomo Bayer Urethane Co., Ltd.Inventor: Toshiaki Imokawa
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Patent number: 5179227Abstract: A fractionation process of a methylene bridged polyphenylene polyisocyanate mixture obtained by phosgenating condensation product of aniline and formaldehyde is disclosed.In order to apply the above mixture to a variety of uses, the process separates the mixture into fractions by giving primary attention to the content of 4,4'-and 2,4'-isomer of diphenylmethane diisocyanate and at the same time reduces the content of impurities having acidity and hydrolyzable chlorine.Type: GrantFiled: October 23, 1991Date of Patent: January 12, 1993Assignee: Mitsui Toatsu Chemicals Inc.Inventors: Noritoshi Ishida, Zunzi Tashima, Mitsunori Shimamatsu, Kazunari Nitta, Takashi Nagou
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Patent number: 5171468Abstract: Disclosed herein are a polyiscoyanate comprising a mixture of aromatic polyisocyanates represented by the general formula: ##STR1## wherein A is a phenylene group, alkylene group, alkyl-substituted phenylene group, diphenylene group, diphenyl ether group or naphthylenyl group, R.sub.1 is a halogen atom, lower alkoxy group with a carbon number of 4 or less or lower alkyl group with a carbon number of 5 or less, R.sub.1 s may be the same or different from each other and may form a ring, l is 1 or 2, m is an integer of 0-3, and n is a integer of 0-300, and a production process thereof.Type: GrantFiled: October 11, 1991Date of Patent: December 15, 1992Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Kiyoshi Shikai, Ryuzi Haseyama, Kouzou Hayashi, Katsuyoshi Sasagawa, Akihiro Yamaguchi
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Patent number: 5130454Abstract: Polytetrahydrofuran derivatives of the general formula ##STR1## where n is from 2 to 70, X is the bridge member --NH-- or --O-- and R.sup.1 and R.sup.4 are each hydrogen or various radicals.Type: GrantFiled: December 19, 1990Date of Patent: July 14, 1992Assignee: BASF AktiengesellschaftInventors: Eckhard Hickmann, Ulrich Koehler, Hardo Siegel
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Patent number: 5043473Abstract: The present invention is directed to a liquid, storage-stable isocyanate prepolymer having an isocyanate group content of from 10 to 30% by weight, prepared by reacting:i) a polyamine containing at least two aromatically bound primary amino groups prepared by hydrolyzing an isocyanate compound having an isocyanate group content of from 0.5 to 40% by weight, withii) an isocyanate mixture comprisinga) from 50 to 100% by weight of diphenylmethane diisocyanates of which from 3 to 50% by weight consist of the 2,2'- and 2,4'-isomers, andb) the balance being polyphenylpolymethylene polyisocyanates, with the proviso that if said mixture comprises from 95 to 100% by weight of diphenylmethane diisocyanate, at least 15% by weight of said diisocyanate consisting of the 2,2'- and 2,4'-isomers.Type: GrantFiled: May 11, 1988Date of Patent: August 27, 1991Assignee: Mobay CorporationInventors: William E. Slack, Clarence D. Blue
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Patent number: 5043472Abstract: This invention relates to storage-stable solid isocyanate compositions that are substantially crystalline at room temperature comprising the reaction products of organic isocyanates with substoichiometric quantities of 2-methyl-1,3-propanediol.This invention further to a method of using the solid isocyanate compositions of the invention in the preparation of polyurethane products.Type: GrantFiled: December 21, 1989Date of Patent: August 27, 1991Assignee: Mobay CorporationInventor: Robson Mafoti
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Patent number: 4975514Abstract: A polyisocyanate composition containing an amide-modified product, obtained by modifying a polyisocyanate compound with a polybasic carboxylic acid in an equivalent ratio of carboxyl groups/isocyanate groups being at most 0.9.Type: GrantFiled: May 8, 1989Date of Patent: December 4, 1990Assignee: Asahi Glass Company, Ltd.Inventors: Hiroyuki Watanabe, Hiroshi Washita, Kazuhiko Kuga
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Patent number: 4910333Abstract: The present invention is directed to a process for the production of an isocyanate which is both stable and liquid at 25.degree. C. comprising reacting(i) diphenylmethane diisocyanate,(ii) an organic material containing two or more hydroxy groups, said organic material forming a product solid at 25.degree. C. when reacted with diphenylmethane diisocyanate in an amount such that the resultant solid product would have an isocyanate group content of from 10 to 30% by weight, and(iii) from 1 to 6% by weight, based on the combined weight of (i), (ii) and (iii), of tripropylene glycol, the amounts of components (i), (ii) and (iii) being such that the resultant product has an isocyanate group content of from about 10 to 30% by weight.Type: GrantFiled: June 3, 1987Date of Patent: March 20, 1990Assignee: Mobay CorporationInventor: William E. Slack
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Patent number: 4898971Abstract: The present invention is directed to a liquid, storage-stable isocyanate prepolymer having an isocyanate group content of from 3 to 30% by weight, prepared by reacting(i) a methyl substituted diisocyanato diphenylmethane with(ii) a polyamine of the structure ##STR1## where R represents an m-valent residue obtained by the removal of m-functional groups from a compound having m-functional groups and having a molecular weight of from 76 to about 10,000,X represents --O--, ##STR2## R.sup.1 represents hydrogen or an inert substituent, R.sup.2 represents hydrogen, a C.sub.1 to C.sub.5 alkyl group or a phenyl group,n is 1 or 2, andm is an integer of from 2 to 8.Type: GrantFiled: January 23, 1989Date of Patent: February 6, 1990Assignee: Mobay CorporationInventor: William E. Slack
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Patent number: 4888125Abstract: .alpha.-(4-isocyanatophenoxy)-.psi.-(4-isocyanato-3-methyl-phenoxy)-alkanes and mixtures thereof with the corresponding methyl-free and/or dimethyl substituted diisocyanates are made by phosgenating the corresponding diamine(s). These diisocyanates do not form a precipitate when reacted with a polyol and produce polyurethanes having outstanding properties.Type: GrantFiled: December 3, 1987Date of Patent: December 19, 1989Assignee: Bayer AktiengesellschaftInventors: Klaus Konig, Peter Heitkamper
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Patent number: 4870206Abstract: New compounds containing isocyanatophenoxy groups, corresponding to ##STR1## wherein R.sup.1 denotes a residue of a n-valent polyhydroxyl compound having a molecular weight of about 92-6000, R.sup.2 denotes hydrogen or methyl group and n denotes an integer of from 3 to 8 were found to be suitable as hardeners in the preparation of adhesives.Type: GrantFiled: June 24, 1988Date of Patent: September 26, 1989Assignee: Bayer AktiengesellschaftInventors: Josef Sanders, Rudolf Hombach, Helmut Reiff, Dieter Dieterich, Manfred Dollhausen
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Patent number: 4845283Abstract: This invention relates to alkenylated diphenyldiisocyanates having at least one alkenyl group ortho to an isocyanate group. More particularly the diphenyldiisocyanates are represented by the formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hydrogen, C.sub.1-3 aliphatic, phenyl, halogen or alkoxy radicals, or R.sub.2 and R.sub.4 or R.sub.5 are bridged via an alkylene radical --(CH.sub.2).sub.y -- wherein y=2 to 5 provided not more than one is phenyl, halogen, or alkoxy, X is methylene, alkylene, or branched C.sub.1 -C.sub.6 alkylene group, oxygen, sulfur, carbonyl, sulfonyl or fluoroalkylene group, n is 0 or 1 and z is 0 or 1.The above described alkenylated diphenyldiisocyanates have been found to be well suited for preparing crosslinkable condensation polymers by providing pendant unsaturation for post curing and polymerization. They are also well suited for preparing polyurethane and polyurea elastomer systems.Type: GrantFiled: October 14, 1987Date of Patent: July 4, 1989Assignee: Air Products and Chemicals, Inc.Inventors: William F. Burgoyne, Jr., Dale D. Dixon
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Patent number: 4761498Abstract: The instant invention is directed to diisocyanates based on diphenylmethane which may be methyl-substituted and which are characterized in particular by isocyanate groups in the 3,4'- and optionally in the 3,2'-position. The instant invention is also directed to a number of independent processes for their production and to their use as isocyanate component in the production of polyurethanes.Type: GrantFiled: March 20, 1987Date of Patent: August 2, 1988Assignee: Bayer AktiengesellschaftInventors: Hartmut Knofel, Michael Brockelt, Gerhard Wegener
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Patent number: 4657940Abstract: The present invention is directed to 4,4'-diisocyanato phenylbenzylether, its method of production by reaction of the corresponding diamine with phosgene and the use of the diisocyanate for the production of polyisocyanate polyaddition products, preferably polyurethane plastics.Type: GrantFiled: February 13, 1986Date of Patent: April 14, 1987Assignee: Bayer AktiengesellschaftInventors: Klaus Konig, Peter Heitkamper
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Patent number: 4650899Abstract: A liquid composition comprising a mixture of isomers of essentially diisocyanates having the diphenylmethane structure, the distribution by weight of isomers in the composition for each 100 parts by weight of the composition being:32 to 55% of the 4,4' isomer,30 to 45% of the 2,4' isomer,5 to 12% of the 3,4' isomer,4 to 10% of the 2,2' isomer, and2 to 5% of the 2,3' isomer;and the method of making the composition by first reacting a benzyl halide with benzene, followed by nitration, hydrogenation, and phosgenation.Type: GrantFiled: April 26, 1984Date of Patent: March 17, 1987Assignee: AtochemInventors: Jacques Kervennal, Henri Mathais, Raymond Commandeur
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Patent number: 4613687Abstract: A polyisocyanate or mixture of polyisocyanates in which the main component(s) correspond to the formula: ##STR1## in which R.sub.1, R.sub.2, and R.sub.3 each represent hydrogen or a saturated alkyl group containing from 1 to 12 carbon atoms, provided that at least two of these radicals represent hydrogen; andm, n, o and p each represent 0 or 1, provided that when m, n, o and/or p represent 0, the free valency is taken up by a hydrogen atom and that the sum of m+n+o+p is greater than 1 on a statistical average.Such polyisocyanate or mixture of polyisocyanates may be produced by first reacting a 4-nitrobenzyl halide, a 3-nitrobenzyl halide, a benzyl halide, a benzyl alcohol or a nitrobenzyl chloride isomer mixture with nitrobenzene, an alkyl-substituted nitrobenzene, an alkyl benzene or benzene in the presence of a Friedel-Crafts or an acid catalyst.Type: GrantFiled: August 17, 1981Date of Patent: September 23, 1986Assignee: Bayer AktiengesellschaftInventors: Hartmut Knofel, Michael Brockelt
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Patent number: 4611083Abstract: The invention relates to urea group-containing polyisocyanate mixtures which are liquid at room temperature and have an isocyanate group content of from 15 to 30 weight percent and a diphenylmethane diisocyanate content of from 55 to 90 weight percent, obtained through the reaction of(A) polyoxyalkylene polyamines having a functionality of from 2 to 5 and an amine number from 20 to 250 with a polyisocyanate (B) selected from the group consisting of(B1) a mixture of diphenylmethane diisocyanates and polyphenyl polymethylene polyisocyanates having a diphenylmethane diisocyanate content of from 55 to 90 weight percent or(B2) at least one diphenylmethane diisocyanate isomer.The polyisocyanate mixtures claimed in the invention are used to prepare dense or cellular polyurethane and/or polyisocyanurate plastics, in particular, flexible polyurethane foams.Type: GrantFiled: November 23, 1984Date of Patent: September 9, 1986Assignee: BASF AktiengesellschaftInventors: Ingolf Buethe, Matthias Marx, Willibald Schonleben
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Patent number: 4597910Abstract: Bis-(4-isocyanatophenoxy)-alkanes corresponding to the formula ##STR1## in which R represents a divalent, saturated aliphatic hydrocarbon radical having from 2 to 6 carbon atoms with at least two carbon atoms between the two ether oxygen atoms, andR' represents hydrogen or a methyl group with R' being the same on both rings,are produced by phosgenating the corresponding diamine or an adduct of the corresponding diamine. These diisocyanates are particularly useful in the production of isocyanate addition products having outstanding physical and mechanical properties.Type: GrantFiled: November 8, 1985Date of Patent: July 1, 1986Assignee: Bayer AktiengesellschaftInventors: Klaus Konig, Peter Heitkamper
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Patent number: 4597909Abstract: The present invention is directed to a process for the production of polyamines of the diphenylmethane series having a high diamine content and a low 2,2'-diamino-diphenylmethane content by condensing aniline with formaldehyde in the presence of hydrochloric acid as catalyst, neutralizing the acid catalyst at the end of the condensation reaction and working up the polyamine mixture thus obtained by distillation, characterized in that(a) in a first reaction stage, from 2.0 to 3.5 moles of aniline are reacted with 1 mole of formaldehyde in the presence of hydrochloric acid or a condensation product produced from 2.0 to 3.5 moles of aniline and 1 mole of formaldehyde in the absence of acid catalyst is reacted in the presence of hydrochloric acid at a degree of protonation maintained at 40 to 60% at temperatures below 50.degree. C.Type: GrantFiled: February 21, 1985Date of Patent: July 1, 1986Assignee: Bayer AktiengesellschaftInventors: Berthold Keggenhoff, Enno Mahlmann, Willi Eifler, Gunther Ellendt
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Patent number: 4595744Abstract: Low melting point compositions, comprising a mixture of diisocyanate isomers having the diphenylethane structure, and containing by weight about:35 to 55% of 2,4' isomer,15 to 40% of 4,4' isomer,10 to 25% of 2,2' isomer,3 to 10% of 3,4' isomer, and3 to 8% of 2,3' isomer;to the method of making such compositions by the nitration of aromatic diphenylethane rings, followed by a hydrogenation and phosgenation; and polyurethanes formed utilizing such compositions.Type: GrantFiled: December 7, 1984Date of Patent: June 17, 1986Assignee: AtochemInventors: Jacques Kervennal, Henri Mathais
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Patent number: 4587058Abstract: A diisocyanate corresponding to the general formula: ##STR1## in which R.sub.1, R.sub.2 and R.sub.3 represent hydrogen or a C.sub.2 -C.sub.12 alkyl group provided that two of the radicals R.sub.1, R.sub.2 and R.sub.3 represent hydrogen and the third represents an alkyl group containing from 2 to 12 carbon atoms. Mixtures of diisocyanates in which the described diisocyanate is a major substituent are also within the scope of this disclosure. Such compounds and mixtures are made by reacting a nitrobenzyl halide, an unsubstituted benzyl halide or a benzyl alcohol in the presence of a Friedel-Crafts catalyst with an alkylbenzene or a nitroalkylbenzene and then converting the nitro groups to amino groups by hydrogenation or reduction. The thus-produced amino compound is then phosgenated to form the diisocyanate.The compounds and mixtures of the present invention are useful in the production of polyurethane plastics.Type: GrantFiled: August 7, 1981Date of Patent: May 6, 1986Assignee: Bayer AktiengesellschaftInventors: Hartmut Knofel, Michael Brockelt