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).

  • Patent number: 7153641
    Abstract: 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: Grant
    Filed: January 18, 2005
    Date of Patent: December 26, 2006
    Assignee: Eastman Kodak Company
    Inventors: Robert F. Romanet, Michael W. Crawley, Susan M. Fischer
  • Patent number: 6852480
    Abstract: 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: Grant
    Filed: December 18, 2003
    Date of Patent: February 8, 2005
    Assignee: Eastman Kodak Company
    Inventors: Robert F. Romanet, Frank D. Coms, Susan M. Fischer
  • Patent number: 6787294
    Abstract: 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: Grant
    Filed: June 24, 2003
    Date of Patent: September 7, 2004
    Assignee: Eastman Kodak Company
    Inventors: Robert F. Romanet, Susan M. Fischer, David G. Lincoln, Gary M. Russo
  • Publication number: 20040110962
    Abstract: 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: Application
    Filed: November 6, 2003
    Publication date: June 10, 2004
    Inventors: Ileana Place, John W. Harder, Robert F. Romanet, William B. Vreeland
  • Patent number: 6657066
    Abstract: 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: Grant
    Filed: December 10, 2002
    Date of Patent: December 2, 2003
    Assignee: Eastman Kodak Company
    Inventors: Ileana Place, John W. Harder, Robert F. Romanet, William B. Vreeland
  • Patent number: 6593477
    Abstract: 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: Grant
    Filed: October 29, 2002
    Date of Patent: July 15, 2003
    Assignee: Eastman Kodak Company
    Inventors: Robert F. Romanet, Susan M. Fischer
  • Patent number: 6416943
    Abstract: 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: Grant
    Filed: November 14, 2000
    Date of Patent: July 9, 2002
    Assignee: Eastman Kodak Company
    Inventors: Robert F. Romanet, Susan D. Hill, Stephen P. Singer, Anabisdally I. Bodden
  • Patent number: 6296997
    Abstract: 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, and
    Type: Grant
    Filed: November 7, 2000
    Date of Patent: October 2, 2001
    Assignee: Eastman Kodak Company
    Inventors: Robert F. Romanet, William B. Vreeland, John W. Harder, Christopher T. Brown, Scott R. Conley, Michael P. Youngblood
  • Patent number: 6291152
    Abstract: 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: Grant
    Filed: November 7, 2000
    Date of Patent: September 18, 2001
    Assignee: Eastman Kodak Company
    Inventors: Paul A. Burns, Robert F. Romanet, Susan M. Fischer, David G. Lincoln, Paul P. Spara
  • Patent number: 5985532
    Abstract: 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: Grant
    Filed: October 4, 1996
    Date of Patent: November 16, 1999
    Assignee: Eastman Kodak Company
    Inventors: Judith A. Bose, Louis E. Friedrich, David Hoke, Joan C. Potenza, Robert F. Romanet, Stephen P. Singer, Ronald R. Valente
  • Patent number: 5985533
    Abstract: 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: Grant
    Filed: February 16, 1998
    Date of Patent: November 16, 1999
    Assignee: Eastman Kodak Company
    Inventors: Robert F. Romanet, Paul A. Burns, Susan M. Fischer, Paul P. Spara, Rajiv P. Balasubramanian, David G. Lincoln, Daniel L. Kapp
  • Patent number: 5972587
    Abstract: 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: Grant
    Filed: February 16, 1998
    Date of Patent: October 26, 1999
    Assignee: Eastman Kodak Company
    Inventors: Robert F. Romanet, Paul A. Burns, Susan M. Fischer, Paul P. Spara, Rajiv P. Balasubramanian, David G. Lincoln
  • Patent number: 5972574
    Abstract: 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: Grant
    Filed: January 15, 1997
    Date of Patent: October 26, 1999
    Assignee: Eastman Kodak Company
    Inventors: Susan M. Fischer, Robert F. Romanet, Daniel L. Kapp, Paul A. Burns, Paul P. Spara, Rakesh Jain, William R. Schleigh
  • Patent number: 5681691
    Abstract: 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: Grant
    Filed: October 4, 1996
    Date of Patent: October 28, 1997
    Assignee: Eastman Kodak Company
    Inventors: Judith A. Bose, Louis E. Friedrich, David Hoke, Joan C. Potenza, Robert F. Romanet, Stephen P. Singer, Ronald R. Valente
  • Patent number: 5565572
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: October 15, 1996
    Assignee: Eastman Kodak Company
    Inventors: Joan C. Potenza, Chang K. Kim, David Hoke, Robert F. Romanet
  • Patent number: 5457210
    Abstract: 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: Grant
    Filed: April 22, 1994
    Date of Patent: October 10, 1995
    Assignee: Eastman Kodak Company
    Inventors: Chang K. Kim, Joan C. Potenza, Francesco DeBellis, David Hoke, Robert F. Romanet
  • Patent number: 5302496
    Abstract: 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: Grant
    Filed: September 18, 1992
    Date of Patent: April 12, 1994
    Assignee: Eastman Kodak Company
    Inventors: Robert F. Romanet, Teh-Hsuan Chen
  • Patent number: 5256529
    Abstract: 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: Grant
    Filed: July 27, 1992
    Date of Patent: October 26, 1993
    Assignee: Eastman Kodak Company
    Inventors: Robert F. Romanet, Hans G. Ling, David Hoke
  • Patent number: 5183728
    Abstract: 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: Grant
    Filed: September 12, 1990
    Date of Patent: February 2, 1993
    Assignee: Eastman Kodak Company
    Inventors: Robert F. Romanet, Teh-Hsuan Chen
  • Patent number: 4892805
    Abstract: 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: Grant
    Filed: October 31, 1988
    Date of Patent: January 9, 1990
    Assignee: Eastman Kodak Company
    Inventors: Arlyce T. Bowne, Robert F. Romanet, Sharon E. Normandin