Patents by Inventor Robert F. Romanet
Robert F. Romanet 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: 7153641Abstract: A photographic element comprising a light-sensitive silver halide emulsion layer containing a 1H-pyrazolo[1,5-b][1,2,4]triazole coupler represented by structure (I): wherein R1, R2, and R3 are independently selected unsubstituted alkyl groups comprising of 3 or less carbons with the proviso that one or more of the R1, R2, and R3 groups can be joined to form a ring; R is a straight, cyclic or branched aliphatic carbon chain group and contains at least 9 aliphatic carbon atoms; each R? is an independently selected alkyl or halogen substituent, n is 0 to 3, and R?, when present, does not include an R? in the ring position between the pyrazolotriazole nucleus and the sulfonamide; and X is hydrogen or halogen.Type: GrantFiled: January 18, 2005Date of Patent: December 26, 2006Assignee: Eastman Kodak CompanyInventors: Robert F. Romanet, Michael W. Crawley, Susan M. Fischer
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Patent number: 6852480Abstract: Disclosed is a photographic element comprising a light sensitive silver halide emulsion layer and, having associated with that layer a 1H-pyrazolo[1,5-b]-1,2,4-triazole dye forming coupler having a fully substituted carbon atom at the 6-position, a chloro group at the 7-position, and, at the 2-position, a phenyl ring substituted in the meta position with a carbonamido substituent containing an ?-sulfone moiety. Photographic elements containing these couplers exhibit desirable bleach-fix and activity characteristics.Type: GrantFiled: December 18, 2003Date of Patent: February 8, 2005Assignee: Eastman Kodak CompanyInventors: Robert F. Romanet, Frank D. Coms, Susan M. Fischer
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Patent number: 6787294Abstract: Disclosed is a photographic element comprising a light sensitive silver halide emulsion layer and, having associated with that layer, a 1H-pyrazo[1,5-b]-1,2,4-triazole dye forming coupler having a fully substituted carbon atom at the 6-position, a chloro group at the 7-position, and, at the 2-position, a propionic ester moiety.Type: GrantFiled: June 24, 2003Date of Patent: September 7, 2004Assignee: Eastman Kodak CompanyInventors: Robert F. Romanet, Susan M. Fischer, David G. Lincoln, Gary M. Russo
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Publication number: 20040110962Abstract: Disclosed is a process for forming a 1H-pyrazolo (1,5-b)-[1,2,4]-triazole compound by ring closing a pyrazoloamidine compound comprising reacting the amidine with an oxidizing agent having a reduction potential vs Ag/AgCl that is more positive than −0.16V and less than +1.43V in the presence of a halogen atom. The invention also discloses certain triazole compounds that are successfully made by the conventional process. The process and compounds of the invention provide improved yields and reduce or eliminate unwanted side-reactions.Type: ApplicationFiled: November 6, 2003Publication date: June 10, 2004Inventors: Ileana Place, John W. Harder, Robert F. Romanet, William B. Vreeland
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Patent number: 6657066Abstract: Disclosed is a process for forming a 1H-pyrazolo (1,5-b)-[1,2,4]-triazole compound by ring closing a pyrazoloamidine compound comprising reacting the amidine with an oxidizing agent having a reduction potential vs Ag/AgCl that is more positive than −0.16V and less than +1.43V in the presence of a halogen atom. The invention also discloses certain triazole compounds that are successfully made by the conventional process. The process and compounds of the invention provide improved yields and reduce or eliminate unwanted side-reactions.Type: GrantFiled: December 10, 2002Date of Patent: December 2, 2003Assignee: Eastman Kodak CompanyInventors: Ileana Place, John W. Harder, Robert F. Romanet, William B. Vreeland
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Patent number: 6593477Abstract: Disclosed is a process for forming an N-acylamino pyrazole comprising contacting a N-acyl-3-oxo-imino ether compound either with a salt of hydrazine in the presence of a base or with hydrazine.Type: GrantFiled: October 29, 2002Date of Patent: July 15, 2003Assignee: Eastman Kodak CompanyInventors: Robert F. Romanet, Susan M. Fischer
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Patent number: 6416943Abstract: The invention provides a color photographic element suitable for forming both a colored dye image and a neutral silver-based image, comprising a support bearing at least one light-sensitive silver halide emulsion layer containing a coupler capable of forming a colored dye upon development, and bearing a further light-sensitive silver halide emulsion layer containing a coupler which is capable of releasing a thiovinyl group upon development that is capable of reacting to form a neutral silver-based image.Type: GrantFiled: November 14, 2000Date of Patent: July 9, 2002Assignee: Eastman Kodak CompanyInventors: Robert F. Romanet, Susan D. Hill, Stephen P. Singer, Anabisdally I. Bodden
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Patent number: 6296997Abstract: Disclosed is a photographic element comprising a light-sensitive silver halide emulsion layer having associated therewith a bicyclic azole dye-forming coupler compound having Formula I: wherein: BA represents a bicyclic azole coupler nucleus with —(C(R1)(R2))P— bonded to a ring carbon in a non-coupling position of the coupler nucleus; p is 1 or 2, and each R1 and R2 is independently selected from H and a substituent group, provided that any two of R1 and R2 may join to form a ring; Ra and Rb are each independently selected from H and a substituent group, provided that substituent groups may join to form a ring; each Y is an independently selected substituent and m is 0-4; X is selected from the group consisting of —C(O)—, —S(O)2—, —S(O)—, and —P(O)(OH)—; W is a connecting group having a chain of up to four atoms between X and Z, and n=0 or 1; and a) when n=0, Z is —NHR5 where R5 is H or a substituent, andType: GrantFiled: November 7, 2000Date of Patent: October 2, 2001Assignee: Eastman Kodak CompanyInventors: Robert F. Romanet, William B. Vreeland, John W. Harder, Christopher T. Brown, Scott R. Conley, Michael P. Youngblood
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Patent number: 6291152Abstract: Disclosed is a photographic element comprising a light-sensitive silver halide emulsion layer having associated therewith a bicyclic azole dye-forming coupler, having appended to a ring carbon at a non-coupling position thereof a substituent group represented by the formula: wherein the arrow represents the point of attachment of the substituent group to a non-coupling position of the coupler; R1, R2, R3 and R4 are independently selected hydrogen or substituent groups, provided that any two of R1, R2, R3 and R4 may join to form a ring; Ra and Rb are independently hydrogen or a substituent; each Rc and Rd is an independently selected hydrogen or an alkyl or aryl group, provided that any two of them may join to form a ring and n is 1 to 10; Re is hydrogen or an alkyl or aryl group; each Y is an independently selected substituent group and m is from 0 to 4; and Z is a substituent selected from the group consisting of —C(O)R5, —S(O)2R5, —SOR5, —P(═O)(R6)2 and &Type: GrantFiled: November 7, 2000Date of Patent: September 18, 2001Assignee: Eastman Kodak CompanyInventors: Paul A. Burns, Robert F. Romanet, Susan M. Fischer, David G. Lincoln, Paul P. Spara
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Patent number: 5985532Abstract: The invention provides a photographic element comprising a light sensitive silver halide emulsion layer having associated therewith a dye-forming coupler having formula I: ##STR1## wherein R.sub.1 is selected from the group consisting of alkyl, aryl, and heterocyclic groups;R.sub.2 is selected from the group consisting of hydrogen, alkyl, aryl, and heterocyclic groups;W is C(O) or S(O).sub.2 ;R.sub.3 is selected from the group consisting of alkyl, alkoxy, aryl, aryloxy, and amino groups;each R.sub.4 is independently selected from the group consisting of alkyl, alkoxy, aryl, aryloxy, and alkylamino groups, and n is an integer from 1 to 4;Y is a substituent; andX is H or a coupling-off group;provided that the number of carbon atoms contained in R.sub.1, R.sub.2, R.sub.3 and R.sub.4 combined is at least 18 and provided further that any two or more of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 may be joined to form a ring.Type: GrantFiled: October 4, 1996Date of Patent: November 16, 1999Assignee: Eastman Kodak CompanyInventors: Judith A. Bose, Louis E. Friedrich, David Hoke, Joan C. Potenza, Robert F. Romanet, Stephen P. Singer, Ronald R. Valente
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Patent number: 5985533Abstract: The invention provides a photographic element comprising a silver halide emulsion layer having associated therewith a dye-forming coupler represented by formula II: whereinX is hydrogen or a coupling-off group;R.sup.1, R.sup.2, and R.sup.3 are independently selected alkyl groups, provided that any two of R.sup.1, R.sup.2, and R.sup.3 may join to form a ring;R.sup.4 is hydrogen or a substituent, provided that R.sup.3 and R.sup.4 may join to form a ring when R.sup.4 is a substituent;R.sup.a is hydrogen or a substituent;Y is a substituent with at least one Y substituent having a formula selected from the group consisting of --CONR.sup.b R.sup.c, --NHCOR.sup.d, and --SO.sub.2 R.sup.e, wherein R.sup.b, R.sup.c, and R.sup.d are independently selected from the group consisting of H, alkyl, aryl, and heterocyclic groups and R.sup.e is selected from the group consisting of an alkyl group, an aryl group, a heterocyclic group, --NR.sup.g R.sup.h, and --OR.sup.i wherein R.sup.g, R.sup.h, and R.sup.Type: GrantFiled: February 16, 1998Date of Patent: November 16, 1999Assignee: Eastman Kodak CompanyInventors: Robert F. Romanet, Paul A. Burns, Susan M. Fischer, Paul P. Spara, Rajiv P. Balasubramanian, David G. Lincoln, Daniel L. Kapp
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Patent number: 5972587Abstract: The invention provides a photographic element comprising a silver halide emulsion layer having associated therewith a dye-forming coupler represented by formula II: ##STR1## wherein X is hydrogen or a coupling-off group;R.sup.1, R.sup.2, and R.sup.3 are independently selected alkyl groups, provided that any two of R.sup.1, R.sup.2 and R.sup.3 may join to form a ring;R.sup.4 is hydrogen or a substituent, provided that R.sup.3 and R.sup.4 may join to form a ring when R.sup.4 is a substituent;R.sup.a is hydrogen or a substituent;each Y is an independently selected substituent with at least one Y substituent in the 2-position (relative to oxygen) having the formula --NHSO.sub.2 R.sup.f, wherein R.sup.f is an alkyl or aryl group, and n is from 1 to 5.The element exhibits improved magenta dye light stability.Type: GrantFiled: February 16, 1998Date of Patent: October 26, 1999Assignee: Eastman Kodak CompanyInventors: Robert F. Romanet, Paul A. Burns, Susan M. Fischer, Paul P. Spara, Rajiv P. Balasubramanian, David G. Lincoln
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Patent number: 5972574Abstract: Disclosed is a photographic element comprising a silver halide emulsion layer having associated therewith a dye-forming coupler represented by Formula I: ##STR1## wherein R" represents the group ##STR2## in which R.sup.1, R.sup.2, and R.sup.3 independently selected all groups, provided that any two of R.sup.1, R.sup.2, and R.sup.3 may join to form a ring;R.sup.4 is hydrogen or a substituent, provided that R.sup.3 and R.sup.4 may join to form a ring when R.sup.4 is a substituent; andW is a specified substituent having the formula: ##STR3## and wherein the remaining substituents are as described in the specification. The use of the coupler of Formula I lends improved manufacturability and dye light stability to the element.Type: GrantFiled: January 15, 1997Date of Patent: October 26, 1999Assignee: Eastman Kodak CompanyInventors: Susan M. Fischer, Robert F. Romanet, Daniel L. Kapp, Paul A. Burns, Paul P. Spara, Rakesh Jain, William R. Schleigh
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Patent number: 5681691Abstract: The invention provides a photographic element comprising a light sensitive silver halide emulsion layer having associated therewith a dye-forming coupler having formula I: ##STR1## wherein R.sub.1 is selected from the group consisting of alkyl, aryl, and heterocyclic groups;R.sub.2 is selected from the group consisting of hydrogen, alkyl, aryl, and heterocyclic groups;W is C(O) or S(O).sub.2 ;R.sub.3 is selected from the group consisting of alkyl and aryl groups having a calculated logP of at least 9;Y is a substituent; andX is H or a coupling-off group.Type: GrantFiled: October 4, 1996Date of Patent: October 28, 1997Assignee: Eastman Kodak CompanyInventors: Judith A. Bose, Louis E. Friedrich, David Hoke, Joan C. Potenza, Robert F. Romanet, Stephen P. Singer, Ronald R. Valente
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Patent number: 5565572Abstract: There are described intermediates for the preparation of known pyrazoloazole photographic magenta dye forming couplers and processes for making and using these intermediates. The intermediates are low molecular weight compounds represented by the structure: ##STR1## wherein: R, X, R.sup.1 and Y are defined herein.The process for making these intermediates involves diazotizing a 5-amino-1H-pyrazole to produce a 5-diazo-1H-pyrazole, then condensing the diazotized product with an active methine or methylene compound having a pKa of 14 or less to produce a substituted hydrazone and then subjecting the hydrazone to cyclization and reduction, in either order.Type: GrantFiled: June 7, 1995Date of Patent: October 15, 1996Assignee: Eastman Kodak CompanyInventors: Joan C. Potenza, Chang K. Kim, David Hoke, Robert F. Romanet
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Patent number: 5457210Abstract: There are described intermediates for the preparation of known pyrazoloazole photographic magenta dye forming couplers and processes for making and using these intermediates. The intermediates are low molecular weight compounds represented by the structure: ##STR1## wherein: R, X, R.sup.1 and Y are defined herein.The process for making these intermediates involves diazotizing a 5-amino-1H-pyrazole to produce a 5-diazo-1H-pyrazole, then condensing the diazotized product with an active methine or methylene compound having a pKa of 14 or less to produce a substituted hydrazone and then subjecting the hydrazone to cyclization and reduction, in either order.Type: GrantFiled: April 22, 1994Date of Patent: October 10, 1995Assignee: Eastman Kodak CompanyInventors: Chang K. Kim, Joan C. Potenza, Francesco DeBellis, David Hoke, Robert F. Romanet
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Patent number: 5302496Abstract: Novel pyrazoloazole dye-forming couplers contain on the azole ring a group containing a carbon atom bonded directly to the azole ring and wherein this carbon atom is bonded directly to a nitrogen atom in the group. Such couplers provide advantageous bathochromic hue shift in dyes formed from the couplers. These couplers are useful in photographic silver halide materials and processes.Type: GrantFiled: September 18, 1992Date of Patent: April 12, 1994Assignee: Eastman Kodak CompanyInventors: Robert F. Romanet, Teh-Hsuan Chen
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Patent number: 5256529Abstract: A magenta dye-forming pyrazolotriazole coupler solubilized by one or two sulfonamido groups results in a coupler having increased coupling activity, low fog and good dispersability. The couplers are useful in photographic elements and react with oxidized silver halide to form dyes, and/or to release photographically useful groups.Type: GrantFiled: July 27, 1992Date of Patent: October 26, 1993Assignee: Eastman Kodak CompanyInventors: Robert F. Romanet, Hans G. Ling, David Hoke
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Patent number: 5183728Abstract: Novel pyrazoloazole dye-forming couplers contain on the azole ring a group containing a carbon atom bonded directly to the azole ring and wherein this carbon atom is bonded directly to a nitrogen atom in the group. Such couplers provide advantageous bathochromic hue shift in dyes formed from the couplers. These couplers are useful in photographic silver halide materials and processes.Type: GrantFiled: September 12, 1990Date of Patent: February 2, 1993Assignee: Eastman Kodak CompanyInventors: Robert F. Romanet, Teh-Hsuan Chen
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Patent number: 4892805Abstract: Novel pyrazoloazole dye-forming couplers containing at least one polyether group (A) comprising at least three ether (--O--) groups and terminated by a hydroxy, carboxy or sulfonamido group enables increased reactivity of the coupler in a photographic element and process. The couplers are useful in color photographic silver halide materials and processes.Type: GrantFiled: October 31, 1988Date of Patent: January 9, 1990Assignee: Eastman Kodak CompanyInventors: Arlyce T. Bowne, Robert F. Romanet, Sharon E. Normandin