Patents by Inventor Robert A. Garner
Robert A. Garner has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 4349218Abstract: Fluoran compounds of the formula ##STR1## wherein one of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represents n-alkyl having 6 to 12 carbon atoms and the other R's, independently of each other, represent hydrogen, alkyl having 1 to 12 carbon atoms, alkoxyalkyl having 2 to 8 carbon atoms or benzyl optionally substituted in the ring by nitro, halogen or alkyl having 1 to 6 carbon atoms.The fluoran compounds are particularly useful as color formers which give intense dark green color when they are brought into contact with an electron-accepting co-reactant.Type: GrantFiled: October 3, 1979Date of Patent: September 14, 1982Inventors: Robert Garner, Jean C. Petitpierre
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Patent number: 4349679Abstract: Phthalide compounds of the formula ##STR1## wherein A and B, independently of the other, represent a monovalent radical of the formula ##STR2## wherein X.sub.1 represents an amino group of the formula ##STR3## X.sub.2 represents halogen or an amino group of the formula ##STR4## W is hydrogen or halogen, R.sub.1 and T.sub.1 each represents alkyl of at most 12 carbon atoms which is unsubstituted or substituted by halogen, hydroxyl, cyano, lower alkoxy or lower alkylcarbonyloxy, cycloalkyl, phenyl, benzyl or phenyl or benzyl which are substituted by halogen, nitro, lower alkyl or lower alkoxy, R.sub.2 and T.sub.2 each represents hydrogen, alkyl of at most 12 carbon atoms, which is unsubstituted or substituted by halogen, hydroxyl cyano, lower alkoxy or lower alkyl-carbonyloxy; cycloalkyl, benzyl or benzyl which is substituted by halogen, nitro, lower alkyl or lower alkoxy, and T.sub.2 may also represent acyl having 1 to 8 carbon atoms or each pair of substituents R.sub.1 and R.sub.2 or T.sub.1 and T.sub.Type: GrantFiled: May 10, 1979Date of Patent: September 14, 1982Assignee: Giba-Geigy CorporationInventors: Robert Garner, Michael J. Whitehead
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Patent number: 4302393Abstract: Fluoran compounds of the formula ##STR1## wherein one of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 represents n-alkyl having 6 to 12 carbon atoms and the other R's, independently of each other, represent hydrogen, alkyl having 1 to 12 carbon atoms, alkoxyalkyl having 2 to 8 carbon atoms or benzyl optionally substituted in the ring by nitro, halogen or alkyl having 1 to 6 carbon atoms.The fluoran compounds are particularly useful as color formers which give intense dark green color when they are brought into contact with an electron-accepting co-reactant.Type: GrantFiled: November 9, 1979Date of Patent: November 24, 1981Assignee: Ciba-Geigy CorporationInventors: Robert Garner, Jean C. Petitpierre
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Patent number: 4295663Abstract: A 3-indolyl-3-bis-aminophenyl-phthalide compound of the formula ##STR1## wherein R.sub.1 represents alkyl which has at most 12 carbon atoms and is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, cycloalkyl, or unsubstituted or substituted phenyl or benzyl wherein the substituents are halogen, nitro, lower alkyl or lower alkoxy,R.sub.2 represents hydrogen, alkyl which has at most 12 carbon atoms and is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, cycloalkyl, or benzyl which is unsubstituted or substituted by halogen, nitro, lower alkyl or lower alkoxy, orR.sub.1 and R.sub.2 together with the nitrogen atom linking them represent a 5- or 6-membered heterocyclic radical,X.sub.1 and X.sub.2 independently of one another represent hydrogen, lower alkyl, cycloalkyl, benzyl which is unsubstituted or substituted by halogen, nitro, lower alkyl or lower alkoxy, or acyl having 1 to 8 carbon atoms, and X.sub.Type: GrantFiled: August 25, 1980Date of Patent: October 20, 1981Assignee: Ciba-Geigy CorporationInventors: Jean C. Petitpierre, Robert Garner
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Patent number: 4277400Abstract: Anhydride compounds of the formula ##STR1## wherein A is an optionally substituted amino-phenyl or optionally substituted 3-indolyl radical, Hal represents halogen, Z represents hydrogen, alkyl of 1 to 4 carbon atoms or an optionally substituted phenyl radical and n is 1 to 4; these anhydrides are particularly useful as starting materials for the manufacture of halogenated 3-aryl-3-indolyl-phthalides or fluoran derivatives.Type: GrantFiled: May 10, 1979Date of Patent: July 7, 1981Assignee: Ciba-Geigy CorporationInventors: Robert Garner, Michael J. Whitehead
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Patent number: 4252975Abstract: A 3-indolyl-3-bis-aminophenyl-phthalide compound of the formula ##STR1## wherein R.sub.1 represents alkyl which has at most 12 carbon atoms and is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, cycloalkyl, or unsubstituted or substituted phenyl or benzyl wherein the substituents are halogen, nitro, lower alkyl or lower alkoxy,R.sub.2 represents hydrogen, alkyl which has at most 12 carbon atoms and is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, cycloalkyl, or benzyl which is unsubstituted or substituted by halogen, nitro, lower alkyl or lower alkoxy, orR.sub.1 and R.sub.2 together with the nitrogen atom linking them represent a 5- or 6-membered heterocyclic radical,X.sub.1 and X.sub.2 independently of one another represent hydrogen, lower alkyl, cycloalkyl, benzyl which is unsubstituted or substituted by halogen, nitro, lower alkyl or lower alkoxy, or acyl having 1 to 8 carbon atoms, and X.sub.Type: GrantFiled: December 21, 1978Date of Patent: February 24, 1981Assignee: Ciba-Geigy CorporationInventors: Jean C. Petitpierre, Robert Garner
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Patent number: 4186134Abstract: Phthalides of the formula ##STR1## wherein R.sub.1 and R.sub.2, independently of the other, represent hydrogen, alkyl with 1 to 12 carbon atoms, alkoxyalkyl with 2 to 8 carbon atoms, cycloalkyl with 5 or 6 carbon atoms, benzyl or phenyl, X represents alkyl with 1 to 12 carbon atoms, alkoxy with 1 to 12 carbon atoms or acyloxy with 2 to 12 carbon atoms, Y represents alkyl with 2 to 12 carbon atoms, alkoxy with 3 to 12 carbon atoms or acyloxy with 2 to 12 carbon atoms, Z represents hydrogen, alkyl having 1 to 12 carbon atoms or phenyl, U represents alkyl having 3 to 12 carbon atoms, benzyl or cyanoethyl, or may also represent W when R.sub.1 and R.sub.2 both are benzyl, W represents hydrogen, methyl or ethyl and n is 1 or 2, the benzene rings A and B may be substituted by an amino group optionally substituted by alkyl with 1 to 6 carbon atoms and the benzene ring B may also be substituted by nitro or halogen.Type: GrantFiled: September 19, 1977Date of Patent: January 29, 1980Assignee: Ciba-Geigy CorporationInventors: Robert Garner, Jean C. Petitpierre
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Patent number: 4180656Abstract: An azomethine compound of the general formula ##STR1## wherein A and B, independently of the other, represent naphthylene or phenylene which are unsubstituted or substituted by halogen, cyano, nitro, lower alkyl, lower alkoxy, benzyloxy or phenoxy,X represents a group of the formula ##STR2## R.sub.1 and Y.sub.1 each represents alkyl of at most 12 carbon atoms which is unsubstituted or substituted by halogen, hydroxyl, cyano, lower alkoxy or lower alkyl-carbonyloxy; cycloalkyl, phenyl, benzyl or phenyl or benzyl which are substituted by halogen, nitro, lower alkyl or lower alkoxy,R.sub.2 and Y.sub.2 each represents hydrogen, alkyl of at most 12 carbon atoms which is unsubstituted or substituted by halogen, hydroxyl, cyano, lower alkoxy or lower alkyl-carbonyloxy; cycloalkyl, benzyl or benzyl which is substituted by halogen, nitro, lower alkyl or lower alkoxy or each pair of substituentsR.sub.1 and R.sub.2 or Y.sub.1 and Y.sub.Type: GrantFiled: April 15, 1977Date of Patent: December 25, 1979Assignee: Ciba-Geigy CorporationInventor: Robert Garner
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Patent number: 4153609Abstract: A 3-indolyl-3-bis-aminophenyl-phthalide compound of the formula ##STR1## wherein R.sub.1 represents alkyl which has at most 12 carbon atoms and is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, cycloalkyl, or unsubstituted or substituted phenyl or benzyl wherein the substituents are halogen, nitro, lower alkyl or lower alkoxy,R.sub.2 represents hydrogen, alkyl which has at most 12 carbon atoms and is unsubstituted or substituted by halogen, hydroxyl, cyano or lower alkoxy, cycloalkyl, or benzyl which is unsubstituted or substituted by halogen, nitro, lower alkyl or lower alkoxy, orR.sub.1 and R.sub.2 together with the nitrogen atom linking them represent a 5- or 6-membered heterocyclic radical,X.sub.1 and X.sub.2 independently of one another represent hydrogen, lower alkyl, cycloalkyl, benzyl which is unsubstituted or substituted by halogen, nitro, lower alkyl or lower alkoxy, or acyl having 1 to 8 carbon atoms, and X.sub.Type: GrantFiled: January 10, 1977Date of Patent: May 8, 1979Assignee: Ciba-Geigy CorporationInventors: Jean C. Petitpierre, Robert Garner
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Patent number: 4115450Abstract: Bis-aminoarylethane compounds of the general formula ##STR1## wherein R.sub.1 and R.sub.2, which can be the same or different, represent hydrogen, alkyl of at most 12 carbon atoms which is unsubstituted or substituted by cyano or halogen, alkoxyalkyl of 2 to 8 carbon atoms, benzyl or phenyl,R.sub.3 represents hydrogen, halogen, nitro, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms,X represents an electrophilic group andY represents an inert organic group or an electrophilic group, orX and Y, together with the linkage carbon atom to which they are attached, represent a carbocylic or 5- or 6-membered heterocyclic ring which contains a keto group adjacent to the linkage carbon atom, with the 5-membered heterocyclic ring containing no nitrogen ring members adjacent to each other.These compounds are particularly useful as color formers which give intense violet to green colors of excellent light fastness when they are brought into contact with an electron-accepting co-reactant.Type: GrantFiled: March 3, 1977Date of Patent: September 19, 1978Assignee: Ciba-Geigy CorporationInventors: Robert Garner, Jean Claude Petitpierre
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Patent number: 4102893Abstract: A process for the manufacture of color formers comprising reaction of 2 moles of an indole in the presence of a condensation agent with about 1 mole of an anhydride of the formula ##STR1## wherein A is the residue of a benzene or naphthalene or of a heterocyclic ring, the new color formers obtained by reacting 2 moles of an indole with a halogen- or nitro-substituted phthalic anhydride, or the anhydride of a vicinal naphthalene pyridine or quinoline dicarboxylic acid, the new 3,3-bis-(indol-3-yl)-phthalides substituted at the nitrogen atom with aralkyl or alkyl with 6 to 18 carbon atoms or alkenyl radicals with 3 to 18 carbon atoms or substituted alkyl or alkylene groups with 1 to 18 and 3 to 18 carbon atoms respectively and pressure sensitive recording paper containing at least one of the new color formers.Type: GrantFiled: December 6, 1976Date of Patent: July 25, 1978Assignee: Ciba-Geigy AGInventors: Robert Garner, Max Dunnenberger
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Patent number: 4072690Abstract: Indolyl methylene leuco dyestuffs of the formula ##STR1## wherein X.sub.1 and X.sub.2 independently of the other, represent alkyl with 2 to 12 carbon atoms, alkenyl with at most 12 carbon atoms or phenylalkyl with 1 to 4 carbon atoms in the alkyl part, Y.sub.1 and Y.sub.2 independently of the other, represent hydrogen, alkyl with 1 to 12 carbon atoms or phenyl, Z represents alkyl with 1 to 12 carbon atoms, alkenyl with at most 12 carbon atoms, aryl, aralkyl or a heterocyclic residue and the rings A and B may be further substituted by cyano, nitro, halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms or acyl with 1 to 8 carbon atoms, said methylene compounds are particularly useful as slow developing color formers in pressure-sensitive recording material and exhibit good light and air stability.Type: GrantFiled: January 23, 1975Date of Patent: February 7, 1978Assignee: Ciba-Geigy CorporationInventors: Robert Garner, John B. Henshall, Jean-Claude Petitpierre
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Patent number: 4062866Abstract: Phthalides of the formula ##STR1## wherein R.sub.1 and R.sub.2, independently of the other, represent hydrogen, alkyl with 1 to 12 carbon atoms, alkoxyalkyl with 2 to 8 carbon atoms, cycloalkyl with 5 or 6 carbon atoms, benzyl or phenyl, X represents alkyl with 1 to 12 carbon atoms, alkoxy with 1 to 12 carbon atoms or acyloxy with 2 to 12 carbon atoms, Y represents alkyl with 2 to 12 carbon atoms, alkoxy with 3 to 12 carbon atoms or acyloxy with 2 to 12 carbon atoms, Z represents hydrogen, alkyl having 1 to 12 carbon atoms or phenyl, U represents alkyl having 3 to 12 carbon atoms, benzyl or cyanoethyl, or may also represent W when R.sub.1 and R.sub.2 both are benzyl, W represents hydrogen, methyl or ethyl and n is 1 or 2, the benzene rings A and B may be substituted by an amino group optionally substituted by alkyl with 1 to 6 carbon atoms and the benzene ring B may also be substituted by nitro or halogen.Type: GrantFiled: May 17, 1976Date of Patent: December 13, 1977Assignee: Ciba-Geigy CorporationInventors: Robert Garner, Jean Claude Petitpierre
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Patent number: 4055358Abstract: Nitro-phthalides of the formula ##STR1## in which E is a radical of the formula ##STR2## X and X' each represents alkyl with 1 to 12 carbon atoms, alkoxy with 1 to 12 carbon atoms or acyloxy with 2 to 12 carbon atoms, and X may also be hydrogen. Z represents hydrogen, alkyl having 1 to 12 carbon atoms or phenyl, Y represents hydrogen, alkyl having 1 to 12 carbon atoms, benzyl or cyanoethyl, R.sub.1, R.sub.2, R.sub.1 ' and R.sub.2 ', independently of the other, represents hydrogen, alkyl with 1 to 12 carbon atoms, alkoxyalkyl with 2 to 8 carbon atoms, cycloalkyl with 5 or 6 carbon atoms, benzyl or phenyl and the benzene ring B may be further substituted by halogen, nitro or an amino group optionally substituted by alkyl with 1 to 6 carbon atoms.The nitro-phthalides are particularly useful as color formers which give intense green, blue-green or blue colors when they are brought into contact with an electron-accepting co-reactant.Type: GrantFiled: March 15, 1976Date of Patent: October 25, 1977Assignee: Ciba-Geigy CorporationInventors: Robert Garner, Jean Claude Petitpierre
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Patent number: 4054718Abstract: A heat-sensitive recording material which contains as color former at least one compound of the general formula ##STR1## wherein R.sub.1 and R.sub.2, which can be the same or different, represent hydrogen, alkyl of at most 12 carbon atoms which is unsubstituted or substituted by cyano or halogen, alkoxyalkyl of 2 to 8 carbon atoms, benzyl or phenyl, R.sub.3 represents hydrogen, halogen, nitro, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, andZ represents alkenyl of at most 12 carbon atoms, unsubstituted or ring-substituted aralkyl or aralkenyl, or represents the radical of a reactive organic methylene compound or of a heterocyclic compound which does not contain active methylene groups.Type: GrantFiled: January 21, 1976Date of Patent: October 18, 1977Assignee: Ciba-Geigy CorporationInventors: Robert Garner, Jean Claude Petitpierre
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Patent number: 4046776Abstract: Lactone compounds of the formula ##STR1## wherein X represents alkyl with 1 to 12 carbon atoms, alkoxy with 1 to 12 carbon atoms or acyloxy with 2 to 12 carbon atoms,Y represents an optionally substituted 2-pyrrolyl, 3-indolyl or 3-carbazolyl radical,The nitrogen ring A represents a heterocyclic radical which optionally includes a further hetero atom as a ring member and the ring B represents a 6-membered aromatic or heterocyclic ring which may have an aromatic condensed ring and both the ring B and the condensed ring may be substituted. These lactone compounds are particularly useful as color formers which give intense green-blue, blue or violet-blue colors when they are brought into contact with an electron-accepting co-reactant.Type: GrantFiled: April 2, 1975Date of Patent: September 6, 1977Assignee: Ciba-Geigy CorporationInventors: Robert Garner, Jean-Claude Petitpierre
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Patent number: 4039557Abstract: Thermoreactive recording material comprising at least a support, a binder, a color former and an electron accepting substance, wherein the color former is a compound of the formula ##STR1## wherein R.sub.1 and R.sub.2, independently of the other, represent hydrogen, alkyl with 1 to 12 carbon atoms, alkoxyalkyl with 2 to 8 carbon atoms, cycloalkyl with 5 or 6 carbon atoms, benzyl or phenyl,X and Y, independently of the other, represent alkyl with 1 to 12 carbon atoms, alkoxy with 1 to 12 carbon atoms, phenyl or phenyl substituted by methyl, nitro, halogen, amino or an amino group mono- or disubstituted by alkyl with 1 to 12 carbon atoms, acyl with 2 to 12 carbon atoms or by benzyl, and the benzene ring A may be substituted by 1 to 4 halogen atoms.Type: GrantFiled: January 22, 1976Date of Patent: August 2, 1977Assignee: Ciba-Geigy AGInventors: Robert Garner, Jean Claude Petitpierre
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Patent number: 4025089Abstract: Pressure-sensitive copying or recording material which contains, in its color-producing system, as the color former, at least one azomethine compound of the formula ##STR1## WHEREIN R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each represent hydrogen, alkyl of 1 to 4 carbon atoms, cyanoalkyl of 2 to 5 carbon atoms, unsubstituted benzyl or phenyl, or benzyl or phenyl substituted by halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, orR.sub.1 and R.sub.2 conjointly represent alkylene of 4 to 5 carbon atoms and/or R.sub.3 and R.sub.4 conjointly represent alkylene of 4 or 5 carbon atoms,X.sub.1 and X.sub.2 each represent hydrogen, halogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms,A represents naphthylene or phenylene which is unsubstituted or substituted by halogen, alkyl of 1 to 5 carbon atoms,Alkoxy of 1 to 4 carbon atoms, phenoxy, halogenophenoxy or acylamino of 1 to 9 carbon atoms, and n is 1 or 2.Type: GrantFiled: August 3, 1976Date of Patent: May 24, 1977Assignee: Ciba-Geigy CorporationInventors: Robert Garner, Jean-Claude Petitpierre
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Patent number: 4022802Abstract: A process for the manufacture of N-substituted indoles, wherein an indole is treated with a base in dimethyl sulphoxide, or in a dipolar aprotic solvent with a tertiary acid amide group, such as dimethyl formamide, and subsequently reacted with an alkylating or aralkylating agent and the new indoles carrying in the 1-position an alkyl radical with at least 6 carbon atoms or an alkenyl radical with at least 3 carbon atoms, or an alkyl or alkenyl radical which is substituted with halogen, a hydroxy, cyano, carboxy, lower alkoxy, alkylamino or alkoxycarbonyl group.Type: GrantFiled: May 12, 1975Date of Patent: May 10, 1977Assignee: Ciba-Geigy AGInventors: Robert Garner, Max Dunnenberger
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Patent number: 4011237Abstract: Heterocyclic substituted chromenopyrazoles having the general formula ##STR1## wherein THE NITROGEN-CONTAINING RING A represents a heterocyclic radical which may contain a further heteroatom in the ring,X and Y, independently of the other, represent alkyl of 1 to 12 carbon atoms, alkoxy of 1 to 12 carbon atoms, phenyl or phenyl which is substituted by alkyl of 1 to 4 carbon atoms, nitro, halogen, amino or by an amino group which is mono or disubstituted by alkyl of 1 to 12 carbon atoms, acyl of 2 to 12 carbon atoms or by benzyl, andWherein the benzene ring B is unsubstituted or is substituted by a nitro group or by 1 to 4 halogen atoms. These chromenopyrazoles are particularly useful as color formers which give strong orange, orange red or brownish orange colors when they are brought into contact with an electron-accepting co-reactant.Type: GrantFiled: October 24, 1975Date of Patent: March 8, 1977Assignee: Ciba-Geigy CorporationInventors: Jean Claude Petitpierre, Robert Garner