DE2227461A1 - NEW COLORS - Google Patents

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Publication number
DE2227461A1
DE2227461A1 DE2227461A DE2227461A DE2227461A1 DE 2227461 A1 DE2227461 A1 DE 2227461A1 DE 2227461 A DE2227461 A DE 2227461A DE 2227461 A DE2227461 A DE 2227461A DE 2227461 A1 DE2227461 A1 DE 2227461A1
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Prior art keywords
cyano
benzene
group
butadien
bis
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DE2227461A
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German (de)
Inventor
Johannes George Jacobus Kok
Rudolf Van Moorselaar
Aart Noordermeer
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Koninklijke Philips NV
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Philips Gloeilampenfabrieken NV
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/315—Compounds containing carbon-to-nitrogen triple bonds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
    • C09B23/005—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof
    • C09B23/0058—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof the substituent being CN
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0066—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of a carbocyclic ring,(e.g. benzene, naphtalene, cyclohexene, cyclobutenene-quadratic acid)
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/14—Styryl dyes
    • C09B23/143—Styryl dyes the ethylene chain carrying a COOH or a functionally modified derivative, e.g.-CN, -COR, -COOR, -CON=, C6H5-CH=C-CN
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/24—Anthracenes; Hydrogenated anthracenes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Plural Heterocyclic Compounds (AREA)

Description

PHN.5702,PHN.5702,

PORMELBLATTPORMEL SHEET

.X X' R-(R1J1n-CH=C(CN)-(R2) - C; ^C- (R'3)„, - Οίο») =.XX 'R- (R 1 J 1n -CH = C (CN) - (R 2 ) - C; ^ C- (R' 3 ) ", - Οίο") =

CH-(R' ) , - R«
ν 1 'πι'CH- (R '), - R «
ν 1 'πι'

C CC C

I iI i

Y Y'Y Y '

CH9(CN) -CH 9 (CN) -

- CH- CH = O= O —- C ^
\
Y· C ^
\
Y · XX (R.
X'(R.
X ' >p> p - C
C
I
Y- C
C.
I.
Y I "
Y I "
Y — C '
I
Y»- C '
I.
Y » CH =CH = C(CN)-(R2 C (CN) - (R 2

(1)(1)

(2)(2)

- CH9(CN) (3)- CH 9 (CN) (3)

. - CH9 (CN). - CH 9 (CN)

8 8 7/09978 8 7/0997

Claims (1)

PHN.5702.PHN.5702. PATENTANSPRÜCHE: PATENT CLAIMS : 1. Verbindungen der allgemeinen Formel 1 (siehe Formelblatt), in der R und R1 eine mono-, bi- oder trizyklische aromatische Gruppe darstellen, die höchstens 3 Substituenten trägt oder unsubstituiert ist, R1 und R' eine Alkenylengruppe mit 2n (n = 1 - 5) Kohlenstoffatomen und η konjugierten .doppelten Kohlenstoff-Kohlenstoff-Bindungen in der Kette darstellen, welche Gruppe mit Alkyl (1 oder 2 C-Atome), Phenyl oder Alkyl (1 oder 2 C-Atome) und Phenyl substituiert sein kann, R2 und R'„ eine Vinylgruppe, eine Carbonylgruppe oder eine 1,4-Phenylengruppe darstellen, X und X1 ein Wasserst off atom, eine Methylgruppe oder zusammen ein Sauerstoffatom, ein Schwefelatom, eine Aethenylengruppe, eine Aethylengruppe oder eine Benzogruppe darstellen, Y und Y* ein Wasserstoffatom, eine Methylgruppe oder, wenn X und X1 eine Benzogruppe bilden, zusammen eine Benzogruppe darstellen, und m, m1, ρ und p1 den Wert 0 oder 1 aufweisen, mit der Massgabe, dass, wenn X und X1 zusammen ein Sauerstoffatom, ein Schwefelatom oder eine Aethenylengruppe darstellen und nicht mindestens eine der Gruppen R und Ii1 eine p.Aminophenylgruppe, in der die Aminogruppe 1 oder 2 aus Alkyl und Phenyl gewählte Substituenten trägt, eine Phenylgruppe mit an der Parastelle einem Substituenten, der eine doppelte Bindung in Konjugation mit der Phenylgruppe hat, oder eine bi- oder trizyklische aromatische Gruppe darstellt, die Summe von m, m1, ρ und p' grosser oder gleich 1 ist.1. Compounds of general formula 1 (see formula sheet), in which R and R 1 represent a mono-, bi- or tricyclic aromatic group which carries a maximum of 3 substituents or is unsubstituted, R 1 and R 'an alkenylene group with 2n (n = 1 - 5) carbon atoms and η conjugated double carbon-carbon bonds in the chain, which group can be substituted with alkyl (1 or 2 carbon atoms), phenyl or alkyl (1 or 2 carbon atoms) and phenyl , R 2 and R '"represent a vinyl group, a carbonyl group or a 1,4-phenylene group, X and X 1 represent a hydrogen atom, a methyl group or together an oxygen atom, a sulfur atom, an ethenylene group, an ethylene group or a benzo group, Y and Y * represent a hydrogen atom, a methyl group or, if X and X 1 form a benzo group, together represent a benzo group, and m, m 1 , ρ and p 1 have the value 0 or 1, with the proviso that when X and X 1 together represent an oxygen atom , represent a sulfur atom or an ethenylene group and not at least one of the groups R and Ii 1 a p.Aminophenylgruppe in which the amino group has 1 or 2 substituents selected from alkyl and phenyl, a phenyl group with a substituent at the para, which has a double bond in conjugation with the phenyl group, or represents a bi- or tricyclic aromatic group, the sum of m, m 1 , ρ and p 'is greater than or equal to 1. 2, Verbindungen nach Anspruch 1, dadurch gekennzeichnet, dass R und R« Phenyl, Naphtyl, Anthryl, Benzfuryl, Anthrachinyl,2, connections according to claim 1, characterized in that that R and R «phenyl, naphthyl, anthryl, benzfuryl, anthrachinyl, 209882/0997209882/0997 PHN. 5702.PHN. 5702. Naphthachinyl, Furyl, Thienyl, Pyrrolyl, Indolyl oder Pyridyl darstellen, die höchstens 3 Substituenten tragen, die gewählt sind aus der Gruppe Halogen, Nitro, Phenyl, Benzoyl, Styryl, Hydroxyl, Mercapto, Cyano, Carboxyl, Trifluormethyl, p.Hydroxyphenylazo, Amino, Alkenyl mit bis zu 18 Kohlenstoffatomen, 3,5-Dichlortriaziiioxy, Alkyl, Cycloalkyl, Alkoxy, Trialkylammonium, p.Dlalkylaminophenyl, Alkoxycarbonyl, Halogenoalkyl, Alkylthio und Cyanoalkyl, wobei die Alkylgruppen höchstens 18 Kohlenstoffatome enthalten, S0„M, wobei M ein Alkalimetallatom ist, Methylendioxy, Acyloxy, Acylamino mit höchstens 18 Kohlenstoffatomen, mono- und disubstituiertes Amino, wobei der Substituent aus Alkyl mit höchstens 18 Kohlenstoffatomen, Halogenäthyl, Cyanoäthyl, Hydroxyäthyl und Phenyl gewählt ist.Naphthachinyl, furyl, thienyl, pyrrolyl, indolyl or pyridyl represent, which carry a maximum of 3 substituents selected from the group halogen, nitro, phenyl, benzoyl, styryl, Hydroxyl, mercapto, cyano, carboxyl, trifluoromethyl, p.hydroxyphenylazo, Amino, alkenyl with up to 18 carbon atoms, 3,5-dichlorotriaziiioxy, alkyl, cycloalkyl, alkoxy, trialkylammonium, p.Dlalkylaminophenyl, alkoxycarbonyl, haloalkyl, Alkylthio and cyanoalkyl, where the alkyl groups contain a maximum of 18 carbon atoms, S0 "M, where M is an alkali metal atom is methylenedioxy, acyloxy, acylamino with a maximum of 18 carbon atoms, mono- and disubstituted Amino, where the substituent is made up of alkyl having a maximum of 18 carbon atoms, haloethyl, cyanoethyl, hydroxyethyl and Phenyl is chosen. 3. 1,4-Bis(1-cyano-4-phenylbutadien-1,3-yl-1)benzol.3. 1,4-bis (1-cyano-4-phenylbutadien-1,3-yl-1) benzene. 4. 1,4-Bis ri-cyano-2(4-dimethylaminophenyl)vinyl-1!benzol.4. 1,4-Bis ri-cyano-2 (4-dimethylaminophenyl) vinyl-1! Benzene. 5. 1,4-Bis(i-cyano-6-phenylhexatrien-i,3f5-yl-1)benzol.5. 1,4-bis (i-cyano-6-phenylhexatrien-i, 3f5-yl-1) benzene. 6. 1,4-Bis(1-cyano-e-phenyloctatetraen-i,3 »5,7-yl-1)benzol.6. 1,4-bis (1-cyano-e-phenyloctatetraen-i, 3 »5,7-yl-1) benzene. 7. 1,4-Bis ri-cyano-2(2-chlor-4-dimethylaminophenyl)-vinyl-1[benzol· 7. 1,4-Bis ri-cyano-2 (2-chloro-4-dimethylaminophenyl) vinyl-1 [benzene 8. 1-l*1Cyano-2(4-dimethylaminophenyl) vinyl-1 f -4( 1 -cyano-8-phenyloctatetraen-1f3»5i7-yl-1)benzol. 8. 1-1 * 1 cyano-2 (4-dimethylaminophenyl) vinyl-1 f -4 (1 -cyano-8-phenyloctatetraen-1 f 3 »5i7-yl-1) benzene. 9. 1-j1Cyano-2(4-dimethylaminophenyl)vinyl-1J-4li-cyano~2 (3-natriumsulfonat-4-methoxyphenyl)vinyl-i1 benzol.9. 1-j1Cyano-2 (4-dimethylaminophenyl) vinyl-1J-4li-cyano-2 (3-sodium sulfonate-4-methoxyphenyl) vinyl-i1 benzene. 10. 1-ii-Cyano-2(4-dimethylaminophenyl)vinyl-1*j -4ii-cyano-2 (4-nitrophenyl)vinyl-1J benzol,10. 1-ii-cyano-2 (4-dimethylaminophenyl) vinyl-1 * j -4ii-cyano-2 (4-nitrophenyl) vinyl-1J benzene, 11. 2,5-Bis(1-cyano-4-phenylbutadien-1,3-yl-i)furan.11. 2,5-bis (1-cyano-4-phenylbutadien-1,3-yl-i) furan. 12. 2,5-Bis(1-cyano-4-phenylbutadien-1,3-yl-1)thiofen.12. 2,5-bis (1-cyano-4-phenylbutadien-1,3-yl-1) thiofen. 20938 2/099720938 2/0997 y-y- - 1Ψ - PHN.5702.- 1 Ψ - PHN.5702. 13. 1 ,4-Bisf 1-cyano-4(p-n,dodeoylphenyl-butadien-1 ,3-yl-.il13. 1, 4-Bisf 1-cyano-4 (p-n, dodeoylphenyl-butadiene-1, 3-yl-.il benzol.benzene. 14. 1 ,4-Bis/1-cyano-4(p.ph.enylph.enyl)butadien-1 ,3-yl-ij benzol14. 1, 4-bis / 1-cyano-4 (p.ph.enylph.enyl) butadien-1, 3-yl-ij benzene 15. 1 ,4-Bisl1-cyano-4(o-nitrophenyl)butadien-1 ,3-yl-1_l benzol.15. 1,4-Bisl1-cyano-4 (o-nitrophenyl) butadien-1,3-yl-1-benzene. 16. 1,4-Bisl1-cyano-4(p.methoxyphenyl)butadien-1,3-yl-Vl benzol,16. 1,4-Bisl1-cyano-4 (p.methoxyphenyl) butadien-1,3-yl-Vl benzene, 17. 1,4-Bis/1-cyano-4(p-n.butoxyphenyl)butadien-1»3-yl-IJ benzol.17. 1,4-bis / 1-cyano-4 (p-n.butoxyphenyl) butadien-1 »3-yl-IJ benzene. 18. 1,4-Bisn-cyano-4(3,4-dimethoxyphenyl)butadien-1,3-yl-iJ benzol,18. 1,4-Bisn-cyano-4 (3,4-dimethoxyphenyl) butadien-1,3-yl-iJ benzene, 19. 1t4-Bisj1-cyano-4(p.hydroxphenyl)butadien-1,3-yl-VJ benzol19. 1 t 4-Bisj1-cyano-4 (p.hydroxphenyl) butadien-1,3-yl-VJ benzene 20. 1,4-Bisl1-cyano-4(p.chlorphenyl)butadien-1,3-yl-ijbenzol,20. 1,4-Bisl1-cyano-4 (p.chlorphenyl) butadien-1,3-yl-ijbenzene, 21. 1,4-Bisl1-cyano-4(3-natriumsulfonyl-4-raethoxyphenyl) butadien-1,3-yl-11 benzol.21. 1,4-Bisl1-cyano-4 (3-sodium sulfonyl-4-raethoxyphenyl) butadien-1,3-yl-11 benzene. 22. 1,4-Bis^1-cyano-4(p.dimethylaminopheny1)butadien-1,3-y benzol«22. 1,4-Bis ^ 1-cyano-4 (p.dimethylaminopheny1) butadien-1,3-y benzene" 23. 1,4-Bis/1-cyano-2ip.(p.dimethylaminophenylazo)phenylL -^l J 23. 1,4-Bis / 1-cyano-2ip. (P.dimethylaminophenylazo) phenylL - ^ l J vinyl-1 »benzol.vinyl-1 »benzene. 2k, 1 ,^-BisM-cyano-^^-diphenylbutadien-i ,3-yl-1Jbenzol. 2k, 1, ^ - BisM-cyano - ^^ - diphenylbutadien-i, 3-yl-1Jbenzene. 25. 1 ,4-Bisfi-cyano-MoC .furyl)butadien-1 ,3-yl-Ijbenzol,25.1, 4-Bisfi-cyano-MoC .furyl) butadien-1, 3-yl-Ijbenzol, 26. 1 ,4-Bisfi-cyano-6(o( .furyl)hexatrien-1 ,3,5-yl-iJbenzol.26. 1,4-Bisfi-cyano-6 (o (.furyl) hexatrien-1, 3,5-yl-iJbenzene. 27. 1f4-Bisli-cyano-8(oC -furyl)octatetraen-1,3,5»7-yl-iJ27. 1 f 4-Bisli-cyano-8 (oC -furyl) octatetraen-1,3,5 »7-yl-iJ benzol.benzene. 28. 1 tk-B±sjj\ -cyano-3methyl-4-phenylbutadien-1 ,3-yl-iJbeniiol.28. 1 t kB ± sjj \ -cyano-3methyl-4-phenylbutadien-1,3-yl-iJbeniiol. 29. 1 t4-Bis]j-cyano-4(oC -thienyl)butadien-1 ,3-yl-VJbenzol.29. 1 t 4-bis] j-cyano-4 (oC -thienyl) butadien-1,3-yl-v-benzene. 30. 1 ,4-Bis [jl-cyano-2(4-methoxynaf>tyl-1 )vinyl-1 ]benzol, 31 . 1,4-Bisjj-cyano-2(anthryl-9)vinyl-iJ benzol.30. 1,4-Bis [jl-cyano-2 (4-methoxynaf > tyl-1) vinyl-1] benzene, 31. 1,4-Bisjj-cyano-2 (anthryl-9) vinyl-iJ benzene. 32. 1,4-Bisri-cyano-2(indolyl-3)vinyl-i] benzol.32. 1,4-Bisri-cyano-2 (indolyl-3) vinyl-i] benzene. PHN. 5702.PHN. 5702. 33. 1,4-Bisli-cyano-4(4-methylphenyl)-butadien-1,3-yl-i j benzol.33. 1,4-Bisli-cyano-4 (4-methylphenyl) -butadien-1,3-yl-i j benzene. 34. 1 ,4-BisM -cyano-4(4-methoxyphenyl)-butadien-1 ,3-.yl-.i7 benzol,34.1, 4-BisM -cyano-4 (4-methoxyphenyl) -butadiene-1, 3-.yl-.i7 benzene, 35. 1|4-Bisl1-cyano-4(4-n.butoxyphenyl)-butadien-1,3-yl-1J benzol,35.1 | 4-Bisl1-cyano-4 (4-n-butoxyphenyl) -butadien-1,3-yl-1J benzene, 36. 1,4-BisM-cyano-4(3,4-dimethoxyphenyl)-butadien-1,3-yl-iJ benzol,36. 1,4-BisM-cyano-4 (3,4-dimethoxyphenyl) -butadien-1,3-yl-iJ benzene, 37. 1t4-Bisl1-cyano-4(4-dimethylaminophenyl)-butadien-1f3-yl-1!benzol. 37. 1t4-Bisl1-cyano-4 (4-dimethylaminophenyl) -butadien-1 f 3-yl-1! Benzene. 38. 1 ,4-BisM-cyano-4(oC -thienyl )-butadien-1 ,3-yl-1 !benzol.38.1, 4-BisM-cyano-4 (oC -thienyl) -butadien-1, 3-yl-1! Benzene. 39. 1 ,4-BisJj-cyano-8(o<, furyl )-octatetraen-1 ,3 ,5 , 7-yl-iJ benzol,39. 1,4-BisJj-cyano-8 (o <, furyl) -octatetraen-1, 3, 5, 7-yl-iJ benzene, 40. 1t4-Bis(j-cyano-2(9-athryl)-vinyl-iJ benzol.40. 1 t 4-bis (j-cyano-2 (9-athryl) vinyl-iJ benzene. 41. 1,4-Bis£i -cyano-4(3-natriumsulfonyl-4-methoxyphenyl)-butadien-1,3^yI-I] benzol,41. 1,4-Bis £ i -cyano-4 (3-sodium sulfonyl-4-methoxyphenyl) -butadiene-1,3 ^ yI-I] benzene, 42. Verfahren zur Herstellung neuer Farbstoffe, dadurch gekennzeichnet, dass die Verbindungen der Formel 1, in der R und R1 eine mono-, bi- oder trizyklische aromatische Gruppe darstellen, die höchstens 3 Substituenten trägt oder unsubstituiert ist, R- und R1 eine Alkenylengruppe mit 2n(n =1-5) Kohlenstoffatomen und η konjugierten doppelten Kohlenstoff-Kohlenstoff-Bindungen in der Kette darstellen, welche Gruppe mit Alkyl (t oder 2 C-Atome), Phenyl oder Alkyl (1 oder 2 C-Atome) und Phenyl substituiert sein kann, R2 und R*2 eine Vinylgruppe, eine Carbonylgruppe oder eine 1,4-Phenylengruppe darstellen, X und Xf ein Wasserstoffatom, eine Methylgruppe oder zusammen ein Sauerstoffatom, ein Schwefelatom,42. Process for the preparation of new dyes, characterized in that the compounds of the formula 1 in which R and R 1 represent a mono-, bi- or tricyclic aromatic group which carries at most 3 substituents or is unsubstituted, R- and R 1 represent an alkenylene group with 2n (n = 1-5) carbon atoms and η conjugated double carbon-carbon bonds in the chain, which group with alkyl (t or 2 carbon atoms), phenyl or alkyl (1 or 2 carbon atoms) and phenyl can be substituted, R 2 and R * 2 represent a vinyl group, a carbonyl group or a 1,4-phenylene group, X and X f a hydrogen atom, a methyl group or together an oxygen atom, a sulfur atom, 209882/0997209882/0997 - y( - pun.5702.- y (- pun. 5702. eine Aethenylengruppe, eine Aethylengruppe oder eine Benzogruppe, Y und Y1 ein Wasserstoffatom, ein Methylgruppe oder, wenn X und X1 eine Benzogruppe bilden, zusammen eine Benzogruppe darstellen, und m, m', ρ und p1 den Wert 0 oder 1 aufweisen, mit der Massgabe, dass, wenn X und X1 zusammen ein Sauerstoffatom, ein Schwefelatom oder eine Aethenylengruppe .darstellen und nicht mindestens eine der Gruppen R und R1 eine p.Aminophenylgruppe, in der die Aminogruppe 1 oder 2 aus Alkyl und Phenyl gewählte Substituenten trägt, eine Phenylgruppe mit . ■ an der Parastelle einem Substituenten, der eine doppelte Bindung in Konjugation mit der Phenylgruppe hat, oder eine bi— oder trizyklische aromatische Gruppe darstellt, die Summe von m, m1, ρ und p1 grosser oder gleich 1 ist, durch zur Herstellung von Verbindungen dieses Typs bekannte Verfahren und durch diesen Verfahren analoge Verfahren hergestellt werden. ·an ethenylene group, an ethylene group or a benzo group, Y and Y 1 a hydrogen atom, a methyl group or, if X and X 1 form a benzo group, together represent a benzo group, and m, m ', ρ and p 1 have the value 0 or 1 , with the proviso that when X and X 1 together represent an oxygen atom, a sulfur atom or an ethenylene group and not at least one of the groups R and R 1 is a p.aminophenyl group in which the amino group 1 or 2 is selected from alkyl and phenyl Bears substituents, a phenyl group. ■ at the para a substituent which has a double bond in conjugation with the phenyl group, or represents a bicyclic or tricyclic aromatic group, the sum of m, m 1 , ρ and p 1 is greater than or equal to 1, by for the production of Compounds of this type are known processes and processes analogous to these processes can be prepared. · 43. Verfahren nach Anspruch 42, dadurch gekennzeichnet, dass man ein Aldehyd oder ein Gemisch von Aldehyden der Formel 2 in Gegenwart einer Base mit einem Dinitril der Formel 3 reagieren lässt in welchen Formeln die Symbole die gleiche Bedeutung wie in der Formel 1 haben,43. The method according to claim 42, characterized in that that an aldehyde or a mixture of aldehydes of the formula 2 in the presence of a base with a dinitrile of Formula 3 reacts in which formulas the symbols have the same meaning as in formula 1, 44. Verfahren nach Anspruch 42, dadurch gekennzeichnet, dass man eine Verbindung der Formel 4 in Gegenwart einer Base mit einem Aldehyd der Formel 2 reagieren lasst, in welcher Formel die Symbole die gleiche Bedeutung wie- in der Formel 1 haben· 45· Verfahren zum Farben synthetischer Harze, dadurch gekennzeichnet, tlaes synthetische Harze innig mit einer Vorbindung nach Anspruch 1 gemischt werden·44. The method according to claim 42, characterized in that that a compound of formula 4 is allowed to react with an aldehyde of formula 2 in the presence of a base, in which formula the symbols have the same meaning as in the Formula 1 have · 45 · process for coloring synthetic resins, thereby characterized, tlaes synthetic resins intimately with a Pre-binding according to claim 1 are mixed 2η αaa;/αη972η αaa; / αη97 PHN.5702.PHN.5702. 46. Synthetische Harze, die mit der Verbindung nach Anspruch 1 gefärbt sind,46. Synthetic resins which are colored with the compound according to claim 1, 47» Verfahren zum Anfärben von Fasern, Geweben und Strickereien aus synthetischen Harzen und Wolle, dadurch gekennzeichnet, dass die Fasern, Gewebe und Strickereien mit einer Dispersion einer Verbindung nach Anspruch 1 in Wasser in Berührung gebracht werden.47 »Process for dyeing fibers, fabrics and knitting made of synthetic resins and wool, characterized in that the fibers, fabrics and knitting with a dispersion of a compound according to claim 1 in water. 48, Verfahren nach Anspruch 38, dadurch gekennzeichnet, dass Fasern, Gewebe und Strickereien aus Polyester oder Polyamid anschliessend während einer oder mehrerer Minuten einer Wärmebehandlung bei etwa 2000C unterworfen werden. 49· Fasern, Gewebe und Strickereien aus synthetischen Harzen und Wolle, die mit einer Verbindung nach Anspruch gefärbt sind.48. The method according to claim 38, characterized in that fibers, fabrics and knitwear made of polyester or polyamide are then subjected to a heat treatment at approximately 200 ° C. for one or more minutes. 49 · Fibers, fabrics and knits made of synthetic resins and wool, which are dyed with a compound according to claim. 50, Verfahren zur Herstellung gefärbter Firnisse in Farben, dadurch gekennzeichnet, dass die üblichen Bindemittel innig mit einer Verbindung nach Anspruch 1, gegebenenfalls zusammen mit den üblichen Hilfsstoffen, gemischt werden.50, Process for the production of colored varnishes in colors, characterized in that the usual binders intimately with a compound according to claim 1, optionally together with the usual auxiliaries. 51, Firnisse und Farben, die mit der Verbindung nach Anspruch 1 gefärbt sind.51, varnishes and paints colored with the compound of claim 1. 52, Verfahren zur Herstellung gefärbter Putzmassen, dadurch gekennzeichnet, dass die üblichen Bestandteile für Putzmassen innig mit einer Verbindung nach Anspruch 1 gemischt werden» 52, a method for producing colored plaster compounds, characterized in that the usual components for plaster compounds are intimately mixed with a compound according to claim 1 » 53· Putzmassen, die mit einer Verbindung nach Anspruch gefärbt sind,53 plastering compounds colored with a compound according to claim 54. Verfahren zur Herstellung von Tinten, dadurch gekennzeichnet, dass die üblichen Bestandteile für Tinten54. Process for the production of inks, characterized in that that the usual ingredients for inks 2098827099720988270997 PHN.5702.PHN.5702. mit einer Verbindung nach Anspruch 1 gemischt werden, 55· Tinten, die mit einer Verbindung nach Anspruch 1 gefärbt sind.are mixed with a compound according to claim 1, 55 · inks which are mixed with a compound according to claim 1 are colored. 209882/0997209882/0997
DE2227461A 1971-06-25 1972-06-06 NEW COLORS Withdrawn DE2227461A1 (en)

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Publication number Priority date Publication date Assignee Title
BE573004A (en) * 1957-11-15
DE1061955B (en) * 1956-07-18 1959-07-23 Sandoz Ag Spun-dyed threads or fibers
US3257394A (en) * 1962-08-20 1966-06-21 Du Pont Substantive methine dyes
BE688621A (en) * 1965-10-22 1967-03-31
BE736514A (en) * 1968-09-24 1969-12-31

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1061955B (en) * 1956-07-18 1959-07-23 Sandoz Ag Spun-dyed threads or fibers
CH358534A (en) * 1956-07-18 1961-11-30 Sandoz Ag Process for the preparation of new water-insoluble styryl dyes
BE573004A (en) * 1957-11-15
US3257394A (en) * 1962-08-20 1966-06-21 Du Pont Substantive methine dyes
BE688621A (en) * 1965-10-22 1967-03-31
BE736514A (en) * 1968-09-24 1969-12-31

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NL169605C (en) 1982-08-02
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BE785400A (en) 1972-12-27
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