The Hetero Ring Is Six-membered And Contains Nitrogen (e.g., Pyridine, Etc.) Patents (Class 534/766)
  • Patent number: 4965346
    Abstract: The novel dyes of the general formula I ##STR1## where X is hydrogen or C.sub.1-C.sub.4 -alkyl or is phenyl which is unsubstituted or substituted by fluorine, chlorine, bromine, methyl, methoxy or nitro, Y is cyano, a carboxylic ester group or nitro, Z is cyano, acetyl, benzoyl or unsubstituted or substituted carbamyl, or X and Z or Y and Z may simultaneously be a carboxylic ester group, and R.sup.1 and R.sup.2 independently of one another are each hydrogen or unsubstituted or substituted alkyl or aryl, are very useful for dyeing polyesters, polyester/cellulose blends or thermoplastics.
    Type: Grant
    Filed: March 16, 1989
    Date of Patent: October 23, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Johannes Dehnert, Gunther Lamm, Hermann Loeffler
  • Patent number: 4960873
    Abstract: Isothiazoleazo dyes I ##STR1## where R.sup.1 is H, halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy and A is the radical of a coupling component are used predominantly as disperse dyes for dyeing hydrophobic organic fibers and fiber materials.
    Type: Grant
    Filed: March 9, 1989
    Date of Patent: October 2, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Guenter Hansen, Gunther Lamm, Helmut Reichelt, Ernst Schefczik
  • Patent number: 4952681
    Abstract: Compounds of the formula I ##STR1## where X is fluorine, chlorine, bromine, SO.sub.2 E or unsubstituted or substituted hydroxyl or mercapto, E is alkyl, alkenyl, cycloalkyl, aralkyl, aryl, chlorine or unsubstituted or substituted hydroxyl or amino, Y is cyano, nitro, alkanoyl, aroyl, alkylsulfonyl, arylsulfonyl, carboxyl, a carboxylic ester group or unsubstituted or substituted carbamyl, T is hydrogen, C.sub.1 -C.sub.4 -alkyl, a radical which can be introduced by electrophilic substitution or a radical of the formula --CH.dbd.B, in which B is a radical of a methylene-active compound or of an amine, and K is a radical of a coupling component, are disclosed. They are useful for dyeing synthetic fibers or plastics.
    Type: Grant
    Filed: July 27, 1988
    Date of Patent: August 28, 1990
    Assignee: Sandoz AG
    Inventors: Guenter Hansen, Ernst Schefczik, Karl-Heinz Etzbach, Helmut Reichelt, Hermann Loeffler
  • Patent number: 4929720
    Abstract: Isothiazole dyes of the formula ##STR1## where X is substituted or unsubstituted C.sub.1 -C.sub.8 -alkyl or substituted or unsubstituted phenyl,Y is hydrogen, cyano, chlorine or bromine,R.sup.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,R.sup.2 is hydrogen, cyano, carbamoyl, C.sub.1 -C.sub.4 -monoalkyl- or -dialkyl-carbamoyl, C.sub.1 -C.sub.6 -alkanoyl, C.sub.1 -C.sub.6 -alkoxycarbonyl or 2-(C.sub.1 -C.sub.4 -alkoxy)-ethoxycarbonyl andR.sup.3 is hydrogen, C.sub.1 -C.sub.8 -alkyl which may be substituted and/or interrupted by one or two oxygen atoms, or is C.sub.5 -C.sub.7 -cycloalkyl, C.sub.3 -C.sub.6 -alkenyl or phenyl, are useful for dyeing synthetic fibers.
    Type: Grant
    Filed: November 10, 1988
    Date of Patent: May 29, 1990
    Assignee: Basf Aktiengesellschaft
    Inventors: Guenter Hansen, Ernst Schefczik, Helmut Reichelt
  • Patent number: 4855412
    Abstract: Compounds of the general formula ##STR1## where D is a radical of the formula ##STR2## and one of the two radicals L.sup.1 and L.sup.2 is unsubstituted amino and the other the radical ##STR3## where R.sup.1 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.2 -C.sub.4 -alkyl or C.sub.1 -C.sub.8 -acyloxy-C.sub.2 -C.sub.4 -alkyl,R.sup.2 is C.sub.2 -C.sub.10 -alkylene or C.sub.2 -C.sub.10 -alkylene is interrupted by oxygen,T is C.sub.1 -C.sub.8 -alkanoyl which is unsubstituted or is substituted by chlorine or methoxy,B.sup.1 is C.sub.1 -C.sub.4 -alkyl or benzyl or phenyl, which are each unsubstituted or are each substituted by methyl, methoxy or chlorine,B.sup.2 is B.sup.1, hydrogen, halogen, cyano or C.sub.1 -C.sub.5 -alkoxycarbonyl,X.sup.1 is hydrogen, nitro, cyano, C.sub.1 -C.sub.9 -alkoxycarbonyl, C.sub.1 -C.sub.9 -mono- or -dialkylaminocarbonyl, trifluoromethyl, methylsulfonyl or ethylsulfonyl,X.sup.2 is nitro or C.sub.1 -C.sub.5 -alkoxycarbonyl,X.sup.3 is X.sup.
    Type: Grant
    Filed: April 24, 1987
    Date of Patent: August 8, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Johannes Dehnert, Gunther Lamm, Hermann Loeffler
  • Patent number: 4855413
    Abstract: The novel dyes of the general formula I ##STR1## where X is hydrogen or C.sub.1 14 C.sub.4 -alkyl or is phenyl which is unsubstituted or substituted by fluorine, chlorine, bromine, methyl, methoxy or nitro, Y is cyano, a carboxylic ester group or nitro, Z is cyano, acetyl, benzoyl or unsubstituted or substituted carbamyl, or X and Z or Y and Z may simultaneously be a carboxylic ester group, and R.sup.1 and R.sup.2 independently of one another are each hydrogen or unsubstituted or substituted alkyl or aryl, are very useful for dyeing polyesters, polyester/cellulose blends or thermoplastics.
    Type: Grant
    Filed: April 28, 1988
    Date of Patent: August 8, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Johannes Dehnert, Gunther Lamm, Hermann Loeffler
  • Patent number: 4826505
    Abstract: A monoazo pyridone compound of the following formula, ##STR1## wherein X is a member selected from hydrogen, halogeno, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, aralkoxycarbonyl, alkylsulfonyl, arylsulfonyl, carbamoyl, sulfamoyl or cyano, and R is alkyl, alkenyl, cycloalkyl, phenyl or anilino, with the provisos that X is a member selected from those defined above except for hydrogen, chloro, methyl and methoxy when R is ethyl, and X is a member selected from those defined above except for alkyl when R is iso-butyl, which is stable under dyeing conditions, and useful for dyeing hydrophobic fiber materials to give dyed products of a deep, fast and brilliant color of greenish yellow to orange.
    Type: Grant
    Filed: February 8, 1988
    Date of Patent: May 2, 1989
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masao Nishikuri, Kiyoyasu Hashimoto, Hideo Hattori
  • Patent number: 4774324
    Abstract: Compounds of the general formula I ##STR1## where X is unsubstituted or substituted alkyl, cycloalkyl, aralkyl or aryl, Y is chlorine, bromine, carbamyl or cyano, Z is hydrogen, carbamyl, cyano or acetyl, R is hydrogen or C.sub.1 -C.sub.3 -alkyl, R.sup.1 and R.sup.3 independently of one another are each hydrogen or unsubstituted or substituted alkyl, alkenyl, cycloalkyl, aralkyl or aryl, R.sup.2 is hydrogen or unsubstituted or substituted alkyl and R.sup.1 and R.sup.2, together with the nitrogen atom, form a saturated 5-membered or 6-membered ring, are particularly useful for dyeing textile fibers.
    Type: Grant
    Filed: March 7, 1986
    Date of Patent: September 27, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Hermann Loeffler, Ernst Schefczik
  • Patent number: 4754022
    Abstract: The invention relates to novel cationic isothiazolazo compounds of the formula ##STR1## wherein R.sub.1 is unsubstituted or substituted C.sub.1 -C.sub.4 alkylR.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl,R.sub.3 is hydrogen or C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted by halogen, cyano, C.sub.1 -C.sub.4 alkoxy or by phenyl which is in turn unsubstituted or substituted by methyl, methoxy and/or halogen,R.sub.5 and R.sub.6 are each independently of the other hydrogen or C.sub.1 -C.sub.4 alkylR.sub.7 is hydrogen, C.sub.1 -C.sub.4 alkyl or phenyl,Y is the direct bond or the group ##STR2## wherein R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.8 and R.sub.9 are each hydrogen and, if Y is the direct bond, they are each independently of the other hydrogen or C.sub.1 -C.sub.4 alkyl, andX.sup..crclbar. is an anion. These compounds can be used as dyes for dyeing or printing in particular polyacrylonitrile materials in blue shades.
    Type: Grant
    Filed: October 24, 1985
    Date of Patent: June 28, 1988
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Moser
  • Patent number: 4685934
    Abstract: Monoazo compounds of formula ##STR1## wherein R.sub.1 is a coupling component radical,R.sub.1 is C.sub.1-6 alkyl; C.sub.1-6 alkyl substituted by 1 or 2 substituents selected from chloro, cyano, hydroxy, C.sub.1-4 alkoxy, phenyl and phenyl substituted by 1 or 2 substituents selected from chloro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, carboxy, sulfo, sulfamoyl and acetamido; C.sub.5-7 cycloalkyl; C.sub.5-7 cycloalkyl substituted by 1 to 3 C.sub.1-4 alkyl groups; phenyl; phenyl substituted by 1 to 3 substituents selected from chloro, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, acetamido (maximum of 1), carboxy (maximum of 1), sulfo (maximum of 1) and --SO.sub.2 NR.sub.7 R.sub.8 (maximum of 1); 1- or 2-naphthyl or 1- or 2-naphthyl substituted by sulfo,whereineach of R.sub.7 and R.sub.8 is independently hydrogen; C.sub.1-4 alkyl; C.sub.1-4 alkyl monosubstituted by hydroxy or phenyl; cyclohexyl; phenyl or phenyl monosubstituted by chloro, methyl or methoxy, or--NR.sub.7 R.sub.
    Type: Grant
    Filed: July 12, 1985
    Date of Patent: August 11, 1987
    Assignee: Sandoz Ltd.
    Inventors: Francois Benguerel, Roland Mislin
  • Patent number: 4668775
    Abstract: A compound of the formula: ##STR1## wherein K is a radical of a coupling component, R is a radical of a methylene-active compound, X is hydrogen or unsubstituted or substituted alkyl, aryl, or hetaryl and Y is cyano, nitro, alkanoyl, aroyl, alkylsulfonyl, arylsulfonyl, carboxyl, a carboxylic ester group or unsubstituted or substituted carbamyl. The present compound is useful for the dyeing of polyesters, nylons, cellulose esters and blends of polyesters and cellulose fibers.
    Type: Grant
    Filed: July 24, 1985
    Date of Patent: May 26, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Udo Bergmann, Erwin Hahn, Guenter Hansen
  • Patent number: 4650860
    Abstract: A compound having the formula: ##STR1## where X is hydrogen, chlorine or bromine, B is hydrogen, methyl, ethyl or propyl, and one of the radicals R.sup.1 or R.sup.2 is phenyl which is unsubtituted or mono- or poly-substituted by chlorine, methyl, ethyl, t-butyl, phenoxy, methoxy, ethoxy, propoxy or butoxy, and the other is C.sub.2 -C.sub.8 -alkyl which is unsubstituted or substituted by C.sub.1 -C.sub.8 -alkoxy or phenyl, or is allyl, cyclopentyl, cyclohexyl, methylcyclohexyl, ##STR2## The compounds of formula (I) are used as dyes, preferably for cellulose and cellulose-containing fabrics.
    Type: Grant
    Filed: June 26, 1985
    Date of Patent: March 17, 1987
    Assignee: BASF Aktiengesellschaft
    Inventors: Johannes Dehnert, Gunther Lamm
  • Patent number: 4619992
    Abstract: A compound of the formula: ##STR1## where R is hydrogen, C.sub.1 -C.sub.4 -alkyl, phenyl, chlorophenyl, methylphenyl, methoxyphenyl or nitrophenyl; R.sup.1 is allyl, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkyl substituted by C.sub.1 -C.sub.8 -alkoxy, phenoxy, phenyl or C.sub.1 -C.sub.8 -alkanoyloxy, cyclopentyl, cyclohexyl, methylcyclohexyl, norbornyl, phenyl or phenyl substituted by chlorine, methyl or alkoxy; R.sup.2 is C.sub.1 -C.sub.10 -alkanoyl, C.sub.1 -C.sub.10 -alkanoyl substituted by alkoxy or phenoxy, cyclohexanoyl, benzoyl, benzoyl substituted by chlorine, methyl or methoxy, C.sub.1 -C.sub.8 -alkoxycarbonyl, aminocarbonyl, phenylaminocarbonyl, CH.sub.3 NHCO, C.sub.2 H.sub.5 NHCO, C.sub.3 H.sub.7 NHCO, C.sub.4 H.sub.9 NHCO, (CH.sub.3).sub.2 NCO, CH.sub.3 SO.sub.2, C.sub.6 H.sub.5 SO.sub.2 or p--CH.sub.3 --C.sub.6 H.sub.4 --SO.sub.2 ; or R.sup.1 and R.sup.2, together with the nitrogen atom, form a ring system, and K is a radical of a coupling component.
    Type: Grant
    Filed: March 12, 1985
    Date of Patent: October 28, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Udo Bergmann, Johannes P. Dix, Guenter Hansen, Ernst Schefczik
  • Patent number: 4562248
    Abstract: Azo dyes having the general formula ##STR1## in which each of X, Y and Z are independently selected from H and a variety of substituents, preferably provided that at least one of X and Y is a substituent selected, for example, from --CN, halogen, alkyl, and alkylsulfonyl, and C is the residue of a phenol, naphthol, indole, imidazothiazole, pyrazolone, thiazole, isothiazole or pyrazole type disperse dye coupling component. These dyes which are unexpectedly non-phototropic produce yellow to orange shades on hydrophobic fibers and exhibit improvements in one or more properties such as dyeability, dye exhaustion rate, light fastness, nonblooming, pH stability, build, fastness to ozone and nitrogen oxide, crock and wash fastness, migration, transfer, and pH stability on polyester, polyamide and other fibers including cellulose ester.
    Type: Grant
    Filed: November 25, 1983
    Date of Patent: December 31, 1985
    Assignee: Eastman Kodak Company
    Inventors: Max A. Weaver, Jean C. Fleischer
  • Patent number: 4529406
    Abstract: A monoazo compound of the formula, ##STR1## wherein X is hydrogen atom or lower alkyl group; Z is hydrogen atom, halogen atom, alkyl group, acylamino group, benzoylamino group or alkylsulfonylamino group; R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently are hydrogen atom or alkyl group, provided that R.sub.1, R.sub.2, R.sub.3 and R.sub.4 cannot simultaneously be hydrogen atoms; and R.sub.5 is hydrogen atom, alkyl group, substituted alkyl group, alkenyl group, cycloalkyl group, aralkyl group or phenyl group.
    Type: Grant
    Filed: July 18, 1983
    Date of Patent: July 16, 1985
    Assignee: Research Association of Dyestuff Manufacturers
    Inventors: Kiyoyasu Hashimoto, Akira Murata, Kiyoteru Kojima, Toshio Nakamatzu, Akira Takeshita
  • Patent number: 4515716
    Abstract: Diaminopyridine-based azo dyes for cellulose-containing fibers, represented by the following formula: ##STR1## and the other is hydrogen, phenyl, benzyl, allyl, or alkyl which are unsubstituted or substituted by hydroxyl or lower alkoxy(whereinA is methylene, ethylene, propylene, or 1,3-butylene;n is 0 or 1;Y.sup.1 and Y.sup.2, which are the same or different, are hydrogen, alkyl, alkenyl, cyclohexyl, aryl, or aralkyl which are unsubstituted or substituted by cyano, hydroxy, lower alkoxy, or dialkylamino, or Y.sup.1 and Y.sup.2 together form a 5- or 6-membered heterocyclic ring (NY.sup.1 Y.sup.2) containing one nitrogen, the total number of carbon atoms of Y.sup.1 and Y.sup.2 being 18 or less;R.sup.1 is nitro, cyano, methylsulfonyl, phenylsulfonyl, mono-lower alkylaminosulfonyl, di-lower alkylaminosulfonyl, acetyl, or benzoyl;R.sup.2 and R.sup.3, which are the same or different, are hydrogen, trifluoromethyl, halogen, or cyano;R.sup.
    Type: Grant
    Filed: September 3, 1982
    Date of Patent: May 7, 1985
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Toshio Niwa, Toshio Hihara
  • Patent number: 4505857
    Abstract: Compounds of the formula ##STR1## in which K is the radical of a coupling component of the aniline, .alpha.-naphthylamine, pyrazolone, aminopyrazole, indole, tetrahydroquinoline, thiazole, phenol, naphthol, pyridine or pyridone series.R is --CHO, --CH.dbd.C(CN)--R.sub.1, --CH.dbd.CH--R.sub.2, --CH.dbd.C(NO.sub.2)--R.sub.3, --CH.dbd.NOH or --CN,wherein R.sub.1 is (C.sub.1-10 alkoxycarbonyl; (C.sub.1-10 alkoxy)carbonyl monosubstituted by chloro, bromo, cyano, hydroxy, C.sub.1-2 alkoxy, (C.sub.1-2 alkyl)carbonyloxy or (C.sub.1-2 alkoxy)carbonyl; (C.sub.1-10 alkoxy)carbonyl disubstituted by hydroxy and by chloro or bromo; (C.sub.3-8 alkenyl)oxycarbonyl; (C.sub.3-8 chloroalkenyl)oxycarbonyl; (C.sub.3-8 bromoalkenyl)oxycarbonyl; propynyloxycarbonyl; benzyloxycarbonyl; chlorobenzyloxycarbonyl; nitrobenzyloxycarbonyl; C.sub.1-4 alkylsulfonyl; phenylsulfonyl; tolylsulfonyl; carbamoyl; (C.sub.1-2 alkyl)carbamoyl; di(C.sub.
    Type: Grant
    Filed: March 10, 1981
    Date of Patent: March 19, 1985
    Assignee: Sandoz Ltd.
    Inventor: Robert Egli
  • Patent number: 4500455
    Abstract: Diaminopyridine dyes for dyeing cellulose-containing fibers, particularly cellulose fibers and polyester-cellulose fibers in from orange to bluish red, with excellent fastness to light. The dyes are represented by the formula (I): ##STR1## X is a hydrogen atom, or a halogen atom; Y is an alkoxy group containing from 1 to 5 carbon atoms, --O--R.sup.10 --O--R.sup.11, or a phenoxy group; andn is 2 or 3, and wherein R.sup.1 is a nitro group, a cyano group, a methylsulfonyl group, a phenylsulfonyl group, a mono- or di-lower alkylaminosulfonyl group, an acetyl group, or a benzoyl group; R.sup.2 and R.sup.3 are each a hydrogen atom, a trifluoromethyl group, a halogen atom, or a cyano group; R.sup.4 is a hydrogen atom, a lower alkyl group, a mono- or di-lower alkylaminosulfonyl group, a mono- or di-lower alkylcarbamoyl group, or an acetylamino group; R.sup.5 and R.sup.6 are each a hydrogen atom, a halogen atom, or a lower alkyl group; R.sup.7 is a lower alkyl group; R.sup.8 is a hydrogen atom or a halogen atom; R.
    Type: Grant
    Filed: July 21, 1982
    Date of Patent: February 19, 1985
    Assignee: Mitsubishi Chemical Industries, Limited
    Inventors: Toshio Niwa, Toshio Hihara, Yukiharu Shimizu
  • Patent number: 4495099
    Abstract: Nondiffusible compounds capable of releasing at least one diffusible magenta dye moiety having the formula: ##STR1## wherein: (a) X represents the atoms necessary to complete a 5- or 6-membered heterocyclic ring;(b) Y represents the atoms necessary to complete a 5- or 6-membered heterocyclic fused ring;(c) CAR represents a ballasted carrier moiety capable of releasing the diffusible magenta dye moiety as a function of development of a silver halide emulsion layer under alkaline conditions;(d) R represents a hydroxy group, a salt thereof, or a hydrolyzable precursor thereof, or CAR which is linked to the dye moiety through an oxygen atom thereon; and(e) n is 0, 1 or 2, with the proviso that when n is 0, then R is CAR which is linked to the dye moiety through an oxygen atom thereon.
    Type: Grant
    Filed: June 15, 1983
    Date of Patent: January 22, 1985
    Assignee: Eastman Kodak Company
    Inventors: Steven Evans, James K. Elwood
  • Patent number: 4495100
    Abstract: Nondiffusible compounds capable of releasing at least one diffusible cyan dye moiety having the formula: ##STR1## wherein: (a) Y represents the atoms necessary to complete a 5- or 6-membered aromatic heterocyclic fused ring;(b) CAR represents a ballasted carrier moiety capable of releasing the diffusible cyan dye moiety as a function of development of a silver halide emulsion layer under alkaline conditions;(c) R represents a hydroxy group, a salt thereof, or a hydrolyzable precursor thereof, or CAR which is linked to the dye moiety through an oxygen atom thereon; and(d) n is 0, 1 or 2 with the proviso that when n is 0, then R is CAR which is linked to the dye moiety through an oxygen atom thereon.
    Type: Grant
    Filed: June 15, 1983
    Date of Patent: January 22, 1985
    Assignee: Eastman Kodak Company
    Inventors: James A. Reczek, James K. Elwood
  • Patent number: 4495098
    Abstract: Coordination complexes of a polyvalent metal ion and a nondiffusible compound capable of releasing at least one diffusible cyan dye moiety having the formula: ##STR1## wherein: (a) Y represents the atoms necessary to complete a 5- or 6-membered aromatic heterocyclic fused ring;(b) CAR represents a ballasted carrier moiety capable of releasing the diffusible cyan dye moiety as a function of development of a silver halide emulsion layer under alkaline conditions;(c) R represents a hydroxy group, a salt thereof, or a hydrolyzable precursor thereof, or CAR which is linked to the dye moiety through an oxygen atom thereon; and(d) n is 0, 1 or 2 with the proviso that when n is 0, then R is CAR which is linked to the dye moiety through an oxygen atom thereon.
    Type: Grant
    Filed: June 15, 1983
    Date of Patent: January 22, 1985
    Assignee: Eastman Kodak Company
    Inventors: James A. Reczek, James K. Elwood
  • Patent number: 4491481
    Abstract: A pigment composition comprising(a) an organic pigment and(b) from 0.5% to 20% by weight, based on the weight of organic pigment, of a pigment derivative having the formula:A--[N.dbd.N--B].sub.nwherein n is 1 or 2, A is an aryl or heterocyclic residue, B is an aryl or heterocyclic residue and wherein A and/or B contains a residue having the formula: ##STR1## wherein Z is a group of atoms necessary to complete a benzimidazole, pyridine, benzodiazepine, quinoline, isoquinoline or naphthimidazole residue, gives printing inks and especially paint media having improved tinctorial strength, gloss and especially improved rheological properties.
    Type: Grant
    Filed: September 23, 1980
    Date of Patent: January 1, 1985
    Assignee: Ciba-Geigy Corporation
    Inventors: George H. Robertson, David Price, Raymond N. Birrell