Having -c(=x)-, Wherein X Is Chalcogen, Attached Indirectly To A Piperdine Ring By Nonionic Bonding Patents (Class 546/190)
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Patent number: 4537960Abstract: N- and O-substituted carbamates are prepared by reacting urea with an aminopropanol at 140.degree. C. or above. The compounds obtained by the novel process are useful starting materials for the preparation of textile finishing agents, stabilizers, plasticizers, dyes and crop protection agents.Type: GrantFiled: September 2, 1983Date of Patent: August 27, 1985Assignee: BASF AktiengesellschaftInventors: Franz Merger, Gerhard Nestler, Friedrich Towae
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Patent number: 4533499Abstract: A process for the production of a compound of formula ##STR1## which comprises reacting a compound of formula ##STR2## or a mixture of the compounds (2a) and (2b) with a compound ZH or a compound of formula ##STR3## or a mixture of the compounds (2c) and (2d) with a compound YH, both reactions under acidic conditions, wherein X and Y are the same or different and each represents an aromatic carbocyclic radical having an unsubstituted or substituted amino group in the para position to the indicated bond, or a heterocyclic group, and Z represents an aryl radical of formula ##STR4## wherein R.sub.1 and R.sub.2 independently of one another represent hydrogen, C.sub.1 -C.sub.12 alkyl, C.sub.2 -C.sub.8 -alkoxyalkyl, cycloalkyl, aralkyl, aryl, or substituted alkyl, cycloalkyl, aralkyl or aryl, or R.sub.1 and R.sub.Type: GrantFiled: April 6, 1984Date of Patent: August 6, 1985Assignee: Ciba-Geigy CorporationInventors: Malcolm C. Clark, John B. Henshall, Derrick A. Hart
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Patent number: 4532348Abstract: 1-(Substituted phenylthiocarbamyl) 3,3-disubstituted formamidine compounds having the structural formula ##STR1## wherein n is 1, 2 or 3,R is alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 6 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogen, nitro, acyl having 1 to 4 carbon atoms, hydroxyl and ##STR2## wherein R.sup.3 and R.sup.4 have the same meaning as R.sup.1 and R.sup.2 defined below,R.sup.1 and R.sup.2 are the same or different and are alkyl having 1 to 6 carbon atoms, or taken together represent the chain --(CH.sub.2).sub.p --(X).sub.m --(CH.sub.2).sub.q and forming a ring structure with the nitrogen to which they are bound wherein p is 1, 2 or 3, q is 2 or 3, X represents --O--, --S--, --SO--, --SO.sub.2 --, --NR.sup.3 --, R.sup.3 is hydrogen or alkyl having 1 to 6 carbon atoms, and m is 0 or 1 and their use as pharmaceutical agents.Type: GrantFiled: July 16, 1980Date of Patent: July 30, 1985Assignee: Stauffer Chemical CompanyInventors: Ferenc M. Pallos, Jack R. DeBaun, Eugene G. Teach
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Patent number: 4529760Abstract: Oligomers of 2,2,6,6-tetramethylpiperidinol polycarboxylic acid esters are provided having the formula: ##STR1## wherein: Z is the residue of an aliphatic or aromatic or nitriloaliphatic or hydroxy aliphatic polycarboxylic acid having from three to six carboxylic acid groups and from one to thirty carbon atoms; ##STR2## wherein R.sub.3 is hydrogen, alkyl and hydroxyalkyl having from one to about twenty carbon atoms; cycloalkyl having from six to about twenty carbon atoms; aryl having from six to about twenty carbon atoms; or cycloalkylene with the N in the ring and having from two to five carbon atoms;R is alkylene having from two to about twelve carbon atoms; cycloalkylene having from three to about twelve carbon atoms; phenylene having from six to about twenty carbon atoms; mixed alkylenecycloalkylene or alkylene phenylene or oxyalkylene having from two to about twelve carbon atoms; ##STR3## wherein R.sub.4 is alkyl having from one to about six carbon atoms;R.sub.Type: GrantFiled: November 1, 1983Date of Patent: July 16, 1985Assignee: Adeka Argus Chemical Co., Ltd.Inventors: William E. Leistner, Motonobu Minagawa, Yutaka Nakahara, Tohru Haruna, Atsushi Nishimura
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Patent number: 4526891Abstract: This invention relates to compounds of the formula: ##STR1## where X is hydrogen, halogen, lower alkoxy, lower alkyl, nitro, hydroxyl and CF.sub.3 ; R is H, and lower alkyl, R.sub.1 is CH.sub.3 SO.sub.3 and ##STR2## where R.sub.2 and R.sub.3 are the same or different and are hydrogen, lower alkyl, mesyl (CH.sub.3 SO.sub.Type: GrantFiled: March 10, 1983Date of Patent: July 2, 1985Assignee: Hoechst Roussel Pharmaceuticals Inc.Inventors: Lawrence L. Martin, Linda L. Setescak
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Patent number: 4500662Abstract: Polysubstituted .alpha.-aminoacetamides of the formula ##STR1## wherein R.sup.1 is tert-alkyl; R.sup.4 is alkyl, phenyl, substituted phenyl, cycloalkyl, piperidinyl, tetraalkylpiperidinyl or an alkylene (.alpha.-aminoacetamide). These compounds are prepared by first reacting an .alpha.-haloacetamide with a base to form an .alpha.-lactam intermediate which in turn is reacted with a primary amine. The compounds are useful as stabilizers of polymeric materials against ultraviolet light degradation.Type: GrantFiled: September 29, 1982Date of Patent: February 19, 1985Assignee: The B. F. Goodrich CompanyInventor: John T. Lai
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Patent number: 4499220Abstract: Copolymer light stabilizers are provided having at least one 2,2,6,6-tetraalkyl piperidyl group in the molecule and a molecular weight within the range from about 1000 to about 20,000, that are copolymers of a maleic or fumaric acid ester containing a 2,2,6,6-tetraalkyl piperidyl group in the alcohol group of the formula: ##STR1## wherein ##STR2## R.sub.2 is alkyl or R.sub.1 ; X is ##STR3## R.sub.6 is lower alkyl; R.sub.3 is hydrogen or alkyl;R.sub.4 is hydrogen or methyl;R.sub.5 is alkylene;Y is ##STR4## R.sub.7 is alkylene; and at least one monomer selected from the group consisting of aliphatic carboxylic acid vinyl ester having from two to eight carbon atoms; alkyl vinyl ethers having from one to eighteen carbon atoms; triallyl isocyanurate; pinene; and tricyclo-(5.2.1.0.sup.2.6)-decene-3; and synthetic resin compositions having improved light stability comprising per 100 parts by weight of resin from 0.001 to 5 parts by weight of the polymeric light stabilizer.Type: GrantFiled: May 20, 1982Date of Patent: February 12, 1985Assignee: Adeka Argus Chemical Co., Ltd.Inventors: Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata
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Patent number: 4489008Abstract: Hydrolytically stable hydroxyl-terminated liquid polymers that are useful in the preparation of polyurethanes prepared by reacting at least one aminoalcohol with a carboxyl-terminated liquid polymer having a carbon-carbon backbone. The hydroxyl-terminated polymers have the formula ##STR1## wherein B is a carbon-carbon backbone, X is HO-- or HO--Y-- a univalent radical obtained by removing a hydrogen atom from an amine group of aminoalcohol containing one primary or secondary hydroxyl group and one primary or secondary amine group per molecule, and the polymers contain an average of greater than 1.5 terminal hydroxyl groups per molecule.Type: GrantFiled: August 9, 1982Date of Patent: December 18, 1984Assignee: The B. F. Goodrich CompanyInventor: Changkiu K. Riew
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Patent number: 4486428Abstract: Bicyclic fused benzenoid compounds of the formula ##STR1## and pharmaceutically acceptable cationic and acid addition salts thereof, where M is O, CH.sub.2 or NR.sub.6 ; R.sub.6 is hydrogen, formyl, carbobenzyloxy or certain carboalkoxyalkyl, alkanoyl, alkyl, aralkyl or aralkylcarbonyl groups;A' is:(1) A where one of A and B is hydrogen such that when A is hydrogen, B is C(R.sub.2 R.sub.3)(CH.sub.2).sub.f Q and f is 1 or 2; when B is hydrogen, A is C(R.sub.2 R.sub.3)(CH.sub.2).sub.f Q and f is 0 or 1, when taken together A and OR.sub.1 form a lactone or certain derivatives thereof;(2) A' is ##STR2## (3) A' is Q.sub.3 ; Q is CO.sub.2 R.sub.7, COR.sub.8, C(OH)R.sub.8 R.sub.9, CN, CONR.sub.12 R.sub.13, CH.sub.2 NR.sub.12 R.sub.13, CH.sub.2 NHCOR.sub.14, CH.sub.2 NHSO.sub.2 R.sub.17 or 5-tetrazoyl;Q.sub.3 is ##STR3## 5-tetrazolyl, CH.sub.2 CONHCOR.sub.7, COOH or certain ester, amide, carboximido or sulfonimido derivatives thereof, CONHOH, CONHCONH.sub.2, or COCH.sub.2 Q.sub.4 where Q.sub.Type: GrantFiled: January 13, 1983Date of Patent: December 4, 1984Assignee: Pfizer Inc.Inventors: James F. Eggler, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4481148Abstract: Hydroxyl-containing liquid polymers having an aliphatic polymeric backbone and sulfide linkages near the terminal portions of the polymer molecule are prepared by polymerizing (1) at least one of selected vinylidene monomers having at least one terminal CH.sub.2 .dbd.C< group per monomer molecule, together with (2) at least one hydroxyl-containing disulfide in the presence of (3) ultraviolet radiation.Type: GrantFiled: March 16, 1981Date of Patent: November 6, 1984Assignee: The B. F. Goodrich CompanyInventor: Changkiu K. Riew
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Patent number: 4481315Abstract: Compounds which contain, in their molecule, at least one 2-(2'-hydroxyphenyl)-benztriazole group or one 2-hydroxybenzophenone group and at least one polyalkylpiperidine group are effective light stabilizers for organic materials, in particular for polymers. The use of the compounds as light stabilizers for lacquers is of particular importance.Type: GrantFiled: February 28, 1983Date of Patent: November 6, 1984Assignee: Ciba-Geigy CorporationInventors: Jean Rody, Mario Slongo
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Patent number: 4479950Abstract: Compounds of the structure ##STR1## wherein: P and Q are independently hydrogen, halo, CF.sub.3, OR.sub.1, SR.sub.1, sulfamoyl, alkyl and NR.sub.1 R.sub.2 ;R.sub.1, and R.sub.2 are independently hydrogen, alkyl, aminoalky, aryl, aralkyl, heteroaryl or cycloalkyl;Y is OH, OR.sub.1, NH.sub.2, or, N(R.sub.1 R.sub.2); andM is alkyl, cycloalkyl, aryl, aminoalkyl, aralkyl, heteroaryl or heterocyclicwherein:the alkyl groups and the alkyl moieties of aminoalkyl, alkoxy and thioalkyl contain from 1 to 6 carbon atoms; the cycloalkyl group contains from 3 to 8 carbon atoms; the aryl group contains from 6 to 10 carbon atoms; the aralkyl group contains from 7 to 16 carbon atoms; and the hetero group is selected from pyrrolidyl, piperidinyl, morpholinyl, pyridyl, quinolinyl, furyl, furfuryl and thienyl; and where Y is a hydroxy, their pharmaceutically acceptable, non-toxic alkali, alkaline earth and amine salts, have angiotensin converting enzyme inhibitory activity.Type: GrantFiled: November 5, 1982Date of Patent: October 30, 1984Assignee: USV Pharmaceutical CorporationInventors: Paul R. Menard, Howard Jones, John T. Suh
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Patent number: 4477616Abstract: Tetra-2,2,6,6-tetramethyl-4-piperidinyl)-3-methyl-5-(1',2'-biscarboxylate)- ethyl-cyclohexane or 3-cyclohexene-1,2-dicarboxylates are provided having the formula (I) or (II): ##STR1## wherein: R.sub.1 is selected from the group consisting of hydrogen, --O, alkyl, hydroxy alkyl and epoxyalkyl having from one to about eighteen carbon atoms, acyl having from one to about eighteen carbon atoms, cycloalkyl having from three to about eighteen carbon atoms; phenyl; phenalkyl and alkylphenyl having from seven to about twenty-four carbon atoms;R.sub.2 is lower alkyl having from one to about six carbon atoms; andX is selected from the group consisting of: ##STR2## as well as stabilized synthetic resin compositions comprising such piperidinyl compounds.Type: GrantFiled: March 3, 1983Date of Patent: October 16, 1984Assignee: Adeka Argus Chemical Co., Ltd.Inventors: Motonobu Minagawa, Yutaka Nakahara, Toshihiro Shibata
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Patent number: 4473694Abstract: Process for the synthesis of hindered polysubstituted .alpha.-amino acetamides which comprises first reacting an .alpha.-haloacetamide with a base to form an intermediate .alpha.-lactam which in turn is reacted with a primary or secondary amine. The product thus obtained can comprise a multifunctional compound having one or more hindered amino moieties. These compounds are highly effective as UV stabilizers in a variety of plastics, especially the alpha monoolefins.Type: GrantFiled: September 29, 1982Date of Patent: September 25, 1984Assignee: The B. F. Goodrich CompanyInventor: John T. Lai
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Patent number: 4468488Abstract: Poly(piperidylamine) alkanes represented by the Formula (I) or (II): ##STR1## and synthetic resin compositions having improved resistance to deterioration by light containing such compounds.Type: GrantFiled: February 28, 1983Date of Patent: August 28, 1984Assignee: Adeka Argus Chemical Co., Ltd.Inventors: Motonobu Minagawa, Yutaka Nakahara, Toshihiro Shibata, Ryozo Arata
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Patent number: 4468352Abstract: The distyrylbiphenyls of the formula ##STR1## in which X and X' independently of one another are a direct bond, oxygen, sulfur, --O--C.sub.1-3 -alkylene-CON(R.sub.4)----CON(R.sub.4)--, --O--C.sub.1-3 -alkylene-COO--, OCO or --COO--, with the proviso that if n+n'=O, X and Y' may not be --CON(R.sub.4)-- or O--C.sub.1-3 -alkylene-CON(R.sub.4)--, and if n+n'=2 and X and X' are --CON(R.sub.4)-- or --COO--, A.sup..crclbar. may not be a phosphite or phosphonate anion, and Y and Y' independently of one another are C.sub.1-20 -alkylene, R.sub.1 and R.sub.1 ' independently of one another are unsubstituted or substituted C.sub.1-8 -alkyl or C.sub.3-4 -alkenyl, or R.sub.1 together with R.sub.2, or R.sub.1 ' together with R.sub.2 ', is a heterocyclic ring, R.sub.2 and R.sub.2 ' independently of one another are unsubstituted or substituted C.sub.1-8 -alkyl or C.sub.3-4 -alkenyl, or R.sub.2 together with R.sub.1, or R.sub.2 ' together with R.sub.1 ', is a heterocyclic ring, or R.sub.1 and R.sub.2, or R.sub.1 ' and R.sub.Type: GrantFiled: April 28, 1982Date of Patent: August 28, 1984Assignee: Ciba-Geigy CorporationInventors: Christian Luthi, Hans R. Meyer, Kurt Weber
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Patent number: 4463001Abstract: The present invention relates to new 6-substituted 6H-dibenzo [b,d]pyran derivatives, to a process for their preparation and pharmaceutical and veterinary compositions containing them.Type: GrantFiled: October 1, 1981Date of Patent: July 31, 1984Assignee: Farmitalia Carlo Erba S.p.A.Inventors: Piero Melloni, Paolo Salvadori, Pier P. Lovisolo
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Patent number: 4463168Abstract: The instant invention relates to a process for the formation of polylactone polymers which are terminated on one end by a tertiary amine group, and on the other end by a hydroxyl group. An .epsilon.-caprolactone is reacted with an aromatic organic amine in the presence of a catalyst.Type: GrantFiled: December 23, 1983Date of Patent: July 31, 1984Assignee: Exxon Research and Engineering Co.Inventor: Robert D. Lundberg
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Patent number: 4460725Abstract: Polyethers containing 2,2,6,6-tetramethyl piperidinyl carboxylic acid ester or ether groups are provided, comprising polymeric units having the structure ##STR1## wherein X is selected from the group consisting of: ##STR2## R.sub.1 is selected from the group consisting of hydrogen, --O, alkyl, hydroxy alkyl and epoxyalkyl having from one to about eighteen carbon atoms, acyl having from one to about eighteen carbon atoms, cycloalkyl having from three to about eighteen carbon atoms; phenyl; phenalkyl and alkylphenyl having from seven to about twenty-four carbon atoms;R.sub.2 is hydrogen or hydroxy;n.sub.1 is 0 or 1;R.sub.3 is lower alkyl having from one to about six carbon atoms; andn is the average number of such units in the polymer; as well as stabilized synthetic resin compositions comprising such polyethers.Type: GrantFiled: March 7, 1983Date of Patent: July 17, 1984Inventors: William E. Leistner, Motonobu Minagawa, Naohiro Kubota, Toshihiro Shibata, Ryozo Arata
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Patent number: 4447428Abstract: Prostanoid compounds are described having the formula: ##STR1## where A is a cyclopentane ring, which is substituted by oxo and/or hydroxy or etherified hydroxy and may be saturated or unsaturated; X is --CH.dbd.CH--or --(CH.sub.2).sub.2 --; R is alkyl having a terminal --COOH or ester group; and Y is amino or substituted amino, particularly heterocyclic amino.The compounds have bronchodilator activity and/or inhibit blood platelet aggregation.The preparation and pharmaceutical formulation of the compounds is also described.Type: GrantFiled: July 15, 1983Date of Patent: May 8, 1984Assignee: Glaxo Group LimitedInventors: Eric W. Collington, Harry Finch, Roger F. Newton
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Patent number: 4444928Abstract: Polymers or oligometic compounds of the general formula ##STR1## in which X, X.sup.a and X.sup.b are an ester, amide or cyano group, Y, Y.sup.a and Y.sup.b are --O-- or --NR.sup.10 --, R.sup.1, R.sup.1a and R.sup.1b are a group which contains a polyalkylpiperidine radical, and R.sup.1a can also be alkyl, and R.sup.3, R.sup.3a and R.sup.3b are alkylene, alkenylene, arylene-dialkylene, cycloalkylene-dialkylene or monooxa-alkylene or polyoxa-alkylene, can be prepared by the polycondensation of malonic acid esters or amides or cyanoacetic acid esters or amides with difunctional compounds, preferably dihalogen compounds, in the presence of bases. The products obtained have a molecular weight of 800 to 20,000 and are outstanding light stabilizers for organic polymers.Type: GrantFiled: August 4, 1982Date of Patent: April 24, 1984Assignee: Ciba-Geigy CorporationInventor: Friedrich Karrer
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Patent number: 4439565Abstract: Oligomeric esteramides having recurring structural units of the formula ##STR1## where G is a hindered amine radical of formula I or II ##STR2## in which R.sup.1 is hydrogen or alkyl having 1 to 4 carbon atoms, R.sup.2 is hydrogen, alkyl having 1 to 12 carbon atoms, allyl, benzyl, acetyl, acryloyl or cyano, Z.sub.1 is a direct bond, --NHCH.sub.2 CH.sub.2 --, --NHCH.sub.2 CH.sub.2 CH.sub.2 -- or --OCH.sub.2 CH.sub.2 --, Z.sub.2 is ethylene or trimethylene, E is a divalent aliphatic, aromatic or alicyclic radical and L is unsubstituted or substituted alkylene, are useful light stabilizers for plastics.Type: GrantFiled: November 10, 1982Date of Patent: March 27, 1984Assignee: Ciba-Geigy CorporationInventors: Roland A. E. Winter, Roger F. Malherbe, Frank Tieh-Yin Fu
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Patent number: 4438112Abstract: Prostanoids are described of the formulae ##STR1## (and the salts thereof) in which: X is cis or trans --CH.dbd.CH-- or CH.sub.2 CH.sub.2 --;R.sup.1 is C.sub.1-7 alkyl terminated by --COOR.sup.10 where R.sup.10 is H, C.sub.1-6 alkyl or aralkyl;Y is a saturated heterocyclic amino group; andR.sup.4 is aralkyl (in which the aryl portion is substituted by alkylthio, alkylsulphinyl, alkylsulphonyl, alkanoylamino, aroylamino, phenalkyl, aminosulphonyl, alkanoylaminosulphonyl, phenylsulphonyl, nitro, tetrazolyl, substituted phenyl or thienyl).These compounds inhibit blood platelet aggregation and have bronchodilatory action, and may be formulated for use as anti-asthmatics and antithrombotic agents.Type: GrantFiled: September 17, 1982Date of Patent: March 20, 1984Assignee: Glaxo Group LimitedInventors: Eric W. Collington, Peter Hallett, Christopher J. Wallis, John Bradshaw
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Patent number: 4435334Abstract: Compounds which contain ammonium groups and sulphonic acid groups and which, in the betaine form, correspond to the formula ##STR1## wherein X denotes --CO-- or --SO.sub.2 --,R.sub.1 denotes hydrogen or alkyl,R.sub.2, R.sub.3 and R.sub.4, independently of one another denote alkyl, alkenyl or aralkyl, orR.sub.4 denotes ##STR2## Y denotes alkylene or xylylene, m denotes 1 or 2,n denotes 0 or 1, andR.sub.5 and R.sub.6, independently of one another, denote hydrogen, alkyl, alkoxy or halogen,and in addition, if n=1,R.sub.2 or R.sub.4 denotes amino, alkylamino, dialkylamino, aryl or cycloalkyl,R.sub.2 and R.sub.3, together with the nitrogen atom which is bonded to them, denote a 5-membered or 6-membered ring,R.sub.2, R.sub.3 and R.sub.4, together with the nitrogen atom which is bonded to them, denote a pyridinium ring, a group of the formula ##STR3## or hydrogen, Y denotes arylene, benzylene or a radical of the formula ##STR4## Z denotes a direct bond, --(CH.sub.2).sub.p --, --O--, --O--(CH.sub.2).sub.Type: GrantFiled: December 28, 1981Date of Patent: March 6, 1984Assignee: Bayer AktiengesellschaftInventors: Frank-Michael Stohr, Peter Wild, Horst Nickel
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Patent number: 4423174Abstract: Synthetic resin compositions of improved resistance to deterioration by heat and light are provided containing a 2,2,6,6-tetramethyl piperidyl ether having the formula: ##STR1## The compounds of the invention can be prepared by the reaction of the 2,2,6,6-tetramethyl piperidyl alcohol R.sub.1 -OH with (poly) trimethylol alkane, (poly) pentaerthritol, or an alcohol containing an oxetane ring, to form the ether.The etherification is carried out by the conventional method, for example, by the reaction of R.sub.1 -OH with the organic sulfonate of the above-mentioned alcohols, or by the reaction of R.sub.1 -OH with the halogenated above-mentioned alcohols in the presence of an alkali or acid acceptor.The compounds where n is equal to 2 or more can be prepared by chain opening polymerization of the corresponding compound containing the oxetane ring.Type: GrantFiled: July 26, 1982Date of Patent: December 27, 1983Assignee: Adeka Argus Chemical Co., Ltd.Inventors: Motonobu Minagawa, Naohiro Kubota, Ryoji Kimura
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Patent number: 4419354Abstract: This disclosure describes certain substituted 9,10-bis(2-aminoethoxy)anthracenes which are useful as modulators of the immune response system in warm-blooded animals and for inducing the regression of tumors in such animals.Type: GrantFiled: June 3, 1982Date of Patent: December 6, 1983Assignee: American Cyanamid CompanyInventors: Ralph G. Child, Stanley A. Lang, Jr.
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Patent number: 4412021Abstract: Polyalkylpiperidyl-ureas of the formula I ##STR1## in which m is 1-4, X, R.sup.2 and R.sup.3 are monovalent substituents and R.sup.1 is a m-valent radical, can be prepared from the corresponding 4-aminopiperidines by reaction with carbamoyl chlorides. They are outstanding stabilizers for plastics, and especially for polyolefins, to protect them against degradation by the action of light.Type: GrantFiled: February 23, 1982Date of Patent: October 25, 1983Assignee: Ciba-Geigy CorporationInventor: Friedrich Karrer
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Patent number: 4409213Abstract: Prostanoid compounds are described having the formula: ##STR1## where A is a cyclopentane ring, which is substituted by oxo and/or hydroxy or etherified hydroxy and may be saturated or unsaturated; X is --CH.dbd.CH-- or --(CH.sub.2).sub.2 --; R is alkyl having a terminal --COOH or ester group; and Y is amino or substituted amino, particularly heterocyclic amino.The compounds have bronchodilator activity and/or inhibit blood platelet aggregation.The preparation and pharmaceutical formulation of the compounds is also described.Type: GrantFiled: November 10, 1982Date of Patent: October 11, 1983Assignee: Glaxo Group LimitedInventors: Eric W. Collington, Harry Finch, Roger F. Newton, Christopher J. Wallis
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Patent number: 4405737Abstract: N-2-Hydroxypropyl piperidines are provided, as well as a process for preparing these compounds, having the formula: ##STR1## wherein X is selected from the group consisting of , ##STR2## wherein R.sub.1 is selected from the group consisting of hydrogen; alkyl; alkenyl; cycloalkyl; alkaryl; hydroxyalkyl; oxyalkyl; acyl and aroyl having from one to about eighteen carbon atoms;R.sub.2 and R.sub.3 are each selected from the group consisting of alkyl, alkenyl, cycloalkyl, alkaryl, hydroxyalkyl, oxyalkyl and haloalkyl having from one to about eighteen carbon atoms;R.sub.4, R.sub.5 and R.sub.6 each are selected from the group consisting of hydrogen, alkyl, alkenyl, cycloalkyl, alkaryl, hydroxyalkyl, oxyalkyl and haloalkyl having from one to about eighteen carbon atoms; and --CH.sub.2 --O--R.sub.1 ;n is 1 or 2; andY, when n is 1, is hydroxy or ##STR3## and when n is 2, is oxyoxygen.Type: GrantFiled: February 5, 1982Date of Patent: September 20, 1983Assignee: Adeka Argus Chemical Co., Ltd.Inventors: Bunji Hirai, Naohiro Kubota, Kazuo Sugibuchi
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Patent number: 4404301Abstract: Polymeric light stabilizers are provided having at least one 2,2,6,6-tetraalkyl piperidyl group in the molecule and a molecular weight within the range from about 1000 to about 20,000, that are polymers of an unsaturated carboxylic acid ester selected from the group consisting of unsaturated cycloaliphatic mono-, di, and tri-carboxylic acid esters having from seven to about thirty carbon atoms; unsaturated branched-chain aliphatic di- and tri-carboxylic acid esters having from four to about thirty carbon atoms; sorbic acid ester, 3,8-nonadienyl acid ester, oleic acid ester, linolenic acid ester and ricinoleic acid ester; or copolymers of at least one thereof with another copolymerizable unsaturated monomer; and synthetic resin compositions having improved light stability comprising per 100 parts by weight of resin from 0.001 to 10 parts by weight of the polymeric light stabilizer.Type: GrantFiled: April 22, 1982Date of Patent: September 13, 1983Assignee: Adeka Argus Chemical Co., Ltd.Inventors: Naohiro Kubota, Toshihiro Shibata, Ryozo Arata
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Patent number: 4395508Abstract: New polycondensates of alkyl-substituted piperidines are disclosed. These new polycondensates are useful for stabilizing thermoplastic polymers, in particular polyolefins, against sunlight, heat and oxidation.A process for producing the new polycondensates is also disclosed, as well as the polymeric compositions stabilized with said new polycondensates.Type: GrantFiled: July 29, 1981Date of Patent: July 26, 1983Assignee: Montedison S.p.A.Inventors: Giuseppe Nelli, Roberto Oriani
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Patent number: 4377690Abstract: Novel ligands of the general formula wherein r is 1 or 2, and L is a piperidine which is substituted by at least one enolate group in the 1-position or 4-position and wherein the ring nitrogen is sterically hindered by alkyl substituents in the adjacent positions. These ligands are useful in preparing light stabilizers.Type: GrantFiled: June 8, 1981Date of Patent: March 22, 1983Assignee: Ciba-Geigy CorporationInventor: Paul Moser
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Patent number: 4371695Abstract: New N-alkyl-piperidine derivatives of hydroxy-benzyl-malonic acid are disclosed. These new compounds are useful for stabilizing thermoplastic polymers, in particular polyole fins, against sunlight, heat and oxidation.A process for producing the new compounds is also disclosed, as well as the use thereof as stabilizers of polymers and polymeric compositions.Type: GrantFiled: June 3, 1981Date of Patent: February 1, 1983Assignee: Montedison S.p.A.Inventors: Piero Di Battista, Francesco Gratani
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Patent number: 4348524Abstract: Compounds of the formula I ##STR1## in which m is 0 or 1 and n is 1 or 2 and R, R.sup.1, R.sup.2, Z and X are as defined in claim 1, and also salts of these compounds, are valuable light stabilizers for organic materials, especially for polymers. The compounds of the formula I can be prepared from the corresponding 4-sec.-aminopiperidines by reaction with cyclic dicarboxylic acid anhydrides and appropriate further reactions.Type: GrantFiled: March 17, 1981Date of Patent: September 7, 1982Assignee: Ciba-Geigy CorporationInventors: Friedrich Karrer, Paul Moser
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Patent number: 4342756Abstract: Compounds are described of the formula ##STR1## (and their salts and solvates) in which: X is cis or trans --CH.dbd.CH--;R.sup.1 is C.sub.1-7 alkyl terminated by --COOR.sup.3 where R.sup.3 is H, C.sub.1-6 alkyl or C.sub.7-10 aralkyl;Y is a saturated heterocyclic amino group having 5-8 ring members; andR.sup.2 is C.sub.2-4 alkanoyl, C.sub.3-6 alkenyl (optionally substituted), C.sub.1-12 alkyl, or substituted or unsubstituted phenylalkyl, biphenylalkyl or naphthylalkyl.These compounds inhibit blood platelet aggregation and bronchoconstriction and may be formulated for use as antithrombotic and anti-asthmatic agents.Type: GrantFiled: April 29, 1981Date of Patent: August 3, 1982Assignee: Glaxo Group LimitedInventors: Eric W. Collington, Peter Hallett, Christopher J. Wallis, John Bradshaw, Norman F. Hayes
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Patent number: 4339576Abstract: 1-[(3- or 4-Benzoylphenyl)-lower-alkyl]-[(CH.sub.2).sub.n --N.dbd.B]-substituted-piperidines, useful as anti-asthmatic, anti-allergic, anti-cholinergic, bronchodilator and anti-inflammatory agents, are prepared by alkylation of an appropriate substituted piperidine with a (3- or 4-benzoylphenyl)-lower-alkyl halide or tosylate; by reaction of a 1-[2-(3- or 4-lithiophenyl)-lower-alkyl]-[(CH.sub.2).sub.n --N.dbd.B]-substituted-piperidine with benzonitrile and hydrolysis of the resulting benzimidoyl compound; or by reduction of a 1-[.alpha.-(3- or 4-benzoylphenyl)-lower-alkanoyl]-[(CH.sub.2).sub.n --N.dbd.B]-substituted-piperidine. The analogous carbinols are prepared by reduction, with an alkali metal borohydride, of the ketone.Type: GrantFiled: August 24, 1981Date of Patent: July 13, 1982Assignee: Sterling Drug Inc.Inventor: Bernard L. Zenitz
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Patent number: 4332954Abstract: Cyclic sulfoperfluoroaliphaticcarboxylic acid anhydrides, amide derivatives thereof, a process for making the same, curable compositions containing cyclic sulfoperfluoroaliphaticcarboxylic acid anhydrides or amide derivatives thereof and cationically-sensitive monomers, and a process for using cyclic sulfoperfluoroaliphaticcarboxylic acid anhydrides or amide derivatives thereof as catalysts for the cure of cationically-sensitive monomers.Type: GrantFiled: January 30, 1981Date of Patent: June 1, 1982Assignee: Minnesota Mining and Manufacturing CompanyInventor: Robert J. Koshar
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Patent number: 4323691Abstract: Described are compounds of the formula ##STR1## wherein ##STR2## wherein Z is hydrogen or loweralkyl, R.sub.5 and R.sub.6 may be the same or different and are hydrogen, loweralkyl or together are alkylene of 4 or 5 carbon atoms,R.sub.2 is hydrogen, halo, haloloweralkyl, loweralkyl, loweralkoxy, loweralkylthio or ##STR3## wherein R.sub.5 and R.sub.6 are previously defined, R.sub.3 is hydroxy, alkoxy, branched alkoxy, adamantyloxy, morpholino, amino or amino substituted by loweralkyl or alkylene of 4 or 5 carbon atoms,R.sub.4 is hydrogen or loweralkyl, andX.sub.1 and X.sub.2 are hydrogen, loweralkyl, halo or when substituted on adjacent carbon atoms of the benzene ring form a 1,3-butadienylene linkage, Y is oxygen or sulfur, and pharmaceutically acceptable salts thereof. The compounds are effective as diuretic agents in increasing urinary excretion.Type: GrantFiled: December 1, 1980Date of Patent: April 6, 1982Assignee: Abbott LaboratoriesInventors: Carroll W. Ours, Cheuk M. Lee
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Patent number: 4321373Abstract: This invention relates to 2-hydroxy-3-naphthoic acid amides of the general formula: ##STR1## wherein R.sub.1 is hydrogen, a substituted or unsubstituted alkyl, cycloalkyl, aralkyl, or aryl group, and R.sub.2 and R.sub.3 are identical or different and are hydrogen, a substituted or unsubstituted alkyl, cycloalkyl, aralkyl, or aryl group, or, together with the nitrogen atom to which they are attached, a substituted or unsubstituted heterocyclic group. The compounds are useful as coupling components for diazo printing.Type: GrantFiled: August 29, 1980Date of Patent: March 23, 1982Assignee: Hoechst AktiengesellschaftInventor: Siegfried Scheler
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Patent number: 4317819Abstract: The invention provides compounds of general formula ##STR1## and physiologically acceptable salts, hydrates and bioprecursors thereof, in whichY and Z, which may be the same or different, each represent oxygen, sulphur, .dbd.CHNO.sub.2 or .dbd.NR.sub.3 where R.sub.3 is hydrogen, nitro, cyano, lower alkyl, aryl, alkylsulphonyl or arylsulphonyl;p has a value from 2 to 12;R.sub.1 represents ##STR2## in which R.sub.4 and R.sub.5 which may be the same or different, each represent hydrogen, lower alkyl, cycloalkyl, lower alkenyl, aralkyl or lower alkyl interrupted by an oxygen atom or a group >N-R.sub.6 in which R.sub.6 represents hydrogen or lower alkyl, or R.sub.4 and R.sub.5 together with the nitrogen atom to which they are attached form a 5 to 7-membered saturated heterocyclic ring which may contain an additional oxygen atom or the group >NR.sub.Type: GrantFiled: December 5, 1980Date of Patent: March 2, 1982Assignee: Glaxo Group LimitedInventors: John W. Clitherow, Barry J. Price, John Bradshaw, Michael Martin-Smith
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Patent number: 4317767Abstract: New N-alkyl-piperidine derivatives of hydroxy-benzyl-malonic acid are disclosed. These new compounds are useful for stabilizing thermoplastic polymers, in partcular polyole fins, against sunlight, heat and oxidation.A process for producing the new compounds is also disclosed, as well as the use thereof as stabilizers of polymers and polymeric compositions.Type: GrantFiled: January 30, 1980Date of Patent: March 2, 1982Assignee: Montedison S.p.A.Inventors: Piero Di Battista, Francesco Gratani
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Patent number: 4316837Abstract: Polyalkylated 4-aminopiperidine derivatives having the formula: ##STR1## wherein R is a C.sub.1 -C.sub.19 alkyl group, a cycloalkyl group of from 5 to 7 carbon atoms, an unsubstituted aryl group, an aryl group substituted with one or more C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy groups, an aralkyl group having 7 or 8 carbon atoms, or ##STR2## where x is an integer from 0 to 4 inclusive and R' is C.sub.1 -C.sub.4 alkyl, which are useful as stabilizers for synthetic polymers are disclosed. Also disclosed are compositions stable to photo-deterioration comprising said polyalkylated 4-aminopiperidine derivatives and a synthetic polymer.Type: GrantFiled: September 10, 1980Date of Patent: February 23, 1982Assignee: Carstab CorporationInventors: Kenneth R. Molt, Mary J. Zestermann
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Patent number: 4316903Abstract: Compounds of the structure: ##STR1## where A is either ##STR2## where R.sub.1 to R.sub.4 are various substituents are active as antibacterials and antifungals.Type: GrantFiled: May 5, 1978Date of Patent: February 23, 1982Assignee: Merck & Co., Inc.Inventors: Nathaniel Grier, Richard A. Dybas, Bruce E. Witzel
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Patent number: 4310668Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl of 1 to 5 carbon atoms or --CO--(CH.sub.2).sub.p --NR'R" wherein p is 0 or an integer from 1 to 4; each of R' and R" when taken individually is hydrogen or alkyl of 1 to 4 carbon atoms; R' and R" when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrrolo, pyrrolidino, morpholino and N-alkylpiperazino having from 1 to 4 carbon atoms in the alkyl group;R.sub.2 is selected from hydrogen, alkanoyl of 1 to 6 carbon atoms and benzoyl;R.sub.3 is selected from hydrogen, methyl and ethyl;R.sub.4 is selected from hydrogen, alkyl of 1 to 6 carbon atoms and benzyl;Z is selected from:(a) alkylene having from one to nine carbon atoms;(b) --(alk.sub.1).sub.m --X--(alk.sub.2).sub.n -- wherein each of (alk.sub.1) and (alk.sub.2) is alkylene having from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.Type: GrantFiled: December 22, 1980Date of Patent: January 12, 1982Assignee: Pfizer Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4310529Abstract: Compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, benzyl, benzoyl, alkanoyl of 1 to 5 carbon atoms or --CO--(CH.sub.2).sub.p --NR'R" wherein p is 0 or an integer from 1 to 4; each of R' and R" when taken individually is hydrogen or alkyl of 1 to 4 carbon atoms; R' and R" when taken together with the nitrogen to which they are attached form a 5- or 6-membered heterocyclic ring selected from piperidino, pyrrolo, pyrrolidino, morpholino and N-alkylpiperazino having from 1 to 4 carbon atoms in the alkyl group;R.sub.2 is selected from hydrogen, alkanoyl of 1 to 6 carbon atoms and benzoyl;R.sub.3 is selected from hydrogen, methyl and ethyl;R.sub.4 is selected from hydrogen, alkyl of 1 to 6 carbon atoms and benzyl;Z is selected from:(a) alkylene having from one to nine carbon atoms;(b) --(alk.sub.1).sub.m --X--(alk.sub.2).sub.n --wherein each of (alk.sub.1) and (alk.sub.2) is alkylene having from 1 to 9 carbon atoms, with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.Type: GrantFiled: December 22, 1980Date of Patent: January 12, 1982Assignee: Pfizer Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4289686Abstract: Compounds which contain, in their molecule, at least one 2-(2'-hydroxyphenyl)-benztriazole group or one 2-hydroxybenzophenone group and at least one polyalkylpiperidine group are effective light stabilizers for organic materials, in particular for polymers. The use of the compounds as light stabilizers for lacquers is of particular importance.Type: GrantFiled: September 17, 1979Date of Patent: September 15, 1981Assignee: Ciba-Geigy CorporationInventors: Jean Rody, Mario Slongo
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Patent number: 4284829Abstract: Compounds useful for pharmacological and medicinal purposes having the formulae ##STR1## wherein R is H, C.sub.1 -C.sub.5 alkanoyl; R.sub.1 is H, benzyl, C.sub.1 14 C.sub.5 alkanoyl, P(O)(OH).sub.2, --CO(CH.sub.2).sub.2 COOH or a basic acyl group; each of R.sub.2 and R.sub.4 is H, C.sub.1 -C.sub.6 alkyl, phenyl, pyridyl or (CH.sub.2).sub.y C.sub.6 H.sub.5 ; y is 1-4; R.sub.3 is H or CH.sub.3 ; Z is C.sub.1 -C.sub.13 alkylene or --(alk.sub.1).sub.m --O--(alk.sub.2).sub.n --; each of (alk.sub.1) and (alk.sub.2) is C.sub.1 -C.sub.13 alkylene with the proviso that the summation of carbon atoms in (alk.sub.1) plus (alk.sub.2) is not greater than 13; each of m and n is 0 or 1; and W is H, pyridyl, phenyl, fluorophenyl or chlorophenyl; intermediates therefor and methods for their preparation and use.Type: GrantFiled: December 22, 1978Date of Patent: August 18, 1981Assignee: Pfizer Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4271294Abstract: Compounds of the formula I ##STR1## wherein Ar.sup.1 and Ar.sup.2 represent unsubstituted or substituted phenyl, R.sup.1 represents hydrogen, alkyl, alkoxy, hydroxyalkyl, allyl, benzyl or a group --O--R.sup.2 -NR.sup.3 R.sup.4, R.sup.2 represents alkylene and --NR.sup.3 R.sup.4 is an open chain or cyclic organic amino group, are effective initiators for the photopolymerization of unsaturated compounds or for the photocrosslinking of polyolefins. They can be obtained by different methods which are in themselves known, in particular by reaction of the corresponding haloalkyl ethers or haloalkyl ketals with primary or secondary amines.Type: GrantFiled: March 13, 1980Date of Patent: June 2, 1981Assignee: Ciba-Geigy CorporationInventors: Louis Felder, Rudolf Kirchmayr, Rinaldo Kusler
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Patent number: 4265803Abstract: The invention entitled "Polymers containing polyalkylpiperidines and use thereof as stabilizers" provides a class of polymers in which groups containing sterically hindered polyalkylpiperidines are linked in the main chain of the polymers via bridging members containing 2-hydroxy-1,3-trimethylene groups.The polymers show superior stabilizing effects for various synthetic polymers such as polyolefins against degradation thereof induced by light and/or heat. The polymers have advantages, as compared with known stabilizer compounds, that they hardly volatile upon processing with heating or during storage of articles containing thereof, and that they are resistant to extraction with solvents from articles containing thereof.Type: GrantFiled: August 7, 1978Date of Patent: May 5, 1981Assignee: Sankyo Company LimitedInventors: Nobuo Soma, Syoji Morimura, Takao Yoshioka, Tomoyuki Kurumada
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Patent number: 4247694Abstract: The invention relates to metal salts of hydroxybenzoic acids which are complexed with a 4-amino-polyalkylpiperidine derivative or to mixed metal salts of a hydroxybenzoic acid and a polyalkylpiperidine carboxylic acid which may be complexed or not with an 4-amino-polyalkylpiperidine. The metal cation may be that of a di- or trivalent metal such as Ni, Co, Al, Zn or Ca. From hydroxybenzoic acids the 3,5-di-tert.butylbenzoic acid is preferred.These salts are valuable light stabilizers for plastics, especially for polyolefins, styrene polymers and polyamides or polyurethanes respectively. The salts show a strong tendency to retain water. For high compatibility with plastics a low water content is of importance.Type: GrantFiled: October 10, 1978Date of Patent: January 27, 1981Assignee: Ciba-Geigy CorporationInventor: Michael Rasberger