EP0005251A2 - Procédé de préparation de sulfinates de 4,4'-diaminobenzhydrol et de ses produits de substitution, et papier-calque contenant ces produits - Google Patents

Procédé de préparation de sulfinates de 4,4'-diaminobenzhydrol et de ses produits de substitution, et papier-calque contenant ces produits Download PDF

Info

Publication number
EP0005251A2
EP0005251A2 EP79101293A EP79101293A EP0005251A2 EP 0005251 A2 EP0005251 A2 EP 0005251A2 EP 79101293 A EP79101293 A EP 79101293A EP 79101293 A EP79101293 A EP 79101293A EP 0005251 A2 EP0005251 A2 EP 0005251A2
Authority
EP
European Patent Office
Prior art keywords
optionally substituted
general formula
radical
independently
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP79101293A
Other languages
German (de)
English (en)
Other versions
EP0005251A3 (en
EP0005251B1 (fr
Inventor
Roderich Dr. Raue
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0005251A2 publication Critical patent/EP0005251A2/fr
Publication of EP0005251A3 publication Critical patent/EP0005251A3/xx
Application granted granted Critical
Publication of EP0005251B1 publication Critical patent/EP0005251B1/fr
Expired legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
    • B41M5/132—Chemical colour-forming components; Additives or binders therefor
    • B41M5/136—Organic colour formers, e.g. leuco dyes

Definitions

  • the alkyl radicals mentioned in the formulas (I) and (II) are generally those having 1 to 6 carbon atoms.
  • the alkyl radicals mentioned under D can have up to 20 carbon atoms.
  • Particularly suitable substituents of the alkyl radicals are, for example, halogen, hydroxy, C 1 -C 4 alkoxy or cyano.
  • Aryl is preferably understood to mean phenyl or 1- or 2-naphthyl and aralkyl benzyl and ⁇ -phenyl-C 1 -C 4 -alkyl.
  • the phenyl rings can be substituted by, for example, 1-4 radicals, such as halogen, C 1 -C 4 -alkyl, hydroxy, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl, carboxyl, amidocarbonyl, cyano, nitro, amidosulfonyl, C 1 -C 3 -Alkylcarbonylamino or Benzoylamino be substituted.
  • Cycloalkyl is especially cyclopentyl and cyclohexyl, e.g. can be substituted by 1-4 radicals, especially methyl.
  • heterocyclic rings which are formed by R and R 2 or by R 3 and R 4 with the adjacent nitrogen atom are the piperidine, N-methylpiperazine and the morpholine ring.
  • heterocyclic rings which are formed by R 1 and / or R 2 being bound to the aromatic radical A or by R 3 and / or R 4 being bound to the aromatic radical B are julolidine, lilolidine, N-methyltetrahydroquinoline and 1,2- Called dimethylindoline.
  • a and B preferably represent a 1,4-phenylene or 1,4-naphthylene radical. These residues can be 1 - substituted 4 substituents such as C 1 -C 4 alkyl, C 1 -C 4 alkoxy or halogen.
  • Halogen is understood to mean in particular fluorine, chlorine and bromine.
  • Suitable hetaryl residues D are e.g. the quinoline (5), quinoline (6) and indazole (7) residues.
  • the process according to the invention is very particularly suitable for the preparation of sulfinates of Michler's hydrol (4,4'-tetramethyldiamino-benzhydrol).
  • Suitable solvents are monohydric and polyhydric alcohols, and also their ethers, for example methanol, ethanol, propanol, methyl glycol, ethyl glycol, butyl glycol, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, ethylene glycol, methyl glycol acetate, ethylene glycol and acetonitrile diacetate, ethylene glycol and acetic acid.
  • ethers for example methanol, ethanol, propanol, methyl glycol, ethyl glycol, butyl glycol, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, ethylene glycol, methyl glycol acetate, ethylene glycol and acetonitrile diacetate, ethylene glycol and acetic acid.
  • Suitable starting materials of the general formula II are: 4,4'-diaminobenzhydrol, 4,4'-tetramethyldiaminobenzhydrol, 4,4'-tetraethyldiaminobenzhydrol, 4,4'-tetramethyldiamino-2,2'-dimethoxybenzohydrol, 4,4'- Tetramethyldiamino-2,2'-dimethylbenzhydrol, 4,4'-Bisbenzylmethylaminobenzhydrol, 4,4'-Bisbenzylvesthylaminobenzhydrol, 4,4-Bisdibenzylaminobenzhydrol, 4,4'-Bisphenylmethylaminobenzhydrol, 4,4'-Bisphenylvesthylaminobenzhydro1,4,4-Bisobethylethyläthyloxäth , 4 tetrachloroethyl diaminobenzhydrol, 4,4'-bispipe
  • Suitable low-molecular organic mono- or dicarboxylic acids are, for example, formic acid, acetic acid, propionic acid, glycolic acid, methoxyacetic acid, ethoxyacetic acid, oxalic acid, maleic acid and succinic acid. Acetic acid is preferred among these carboxylic acids.
  • Suitable sulfinic acids of the formula III are, for example, methanesulfinic acid, ethanesulfinic acid, propanesulfinic acid, butanesulfinic acid, decanesulfinic acid, dodecanesulfinic acid, octadecansulfinic acid, benzylsulfinic acid, 4-methylbenzylsulfinic acid, 4-chlorobenzylsulfinic acid, cyclohexylsulfinsulfonic acid, 2-benzene sulfonic acid, benzenesulfonic acid , 2-methylbenzenesul finic acid, 4-ethylbenzenesulfinic acid, 4-methoxybenzenesulfinic acid, 4-ethoxybenzenesulfinic acid and 4-acetylaminobenzenesulfinic acid.
  • 4-methylbenzenesulfinic acid is particularly preferred.
  • the reaction can be carried out at a temperature of 20-100 ° C, the preferred temperature range is 20-40 ° C.
  • Suitable solvents are: methanol, isopropanol, ethylene glycol, methyl glycol, ethyl glycol, butyl glycol, methyl glycol acetate, ethylene glycol diacetate, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, dioxane, tetrahydrofuran and acetonitrile.
  • Suitable hydrols are: 4,4'-tetramethyldiamino-2,2'-dimethoxybenzhydrol, 4,4'-tetramethyldiamino-2,2'-dimethylbenzhydrol, 4,4'-bisbenzylmethylaminobenzhydrol, 4,4'-bisbenzylethylaminobenzhydrol, 4, 4'-bisdibenzylaminobenzhydrol, 4,4'-bisphenylmethylaminobenzhydrol, 4,4'-bisphenylethylaminobenzhydrol, 4,4'-bisethylethylethylaminobenzhydrol, 4,4'-bischlorethylethylaminobenzhydrol, 4,4'-bispiperidinobenzhydrol, 4,4'-bismorpholinobenzhydrol, 4,4'-bismorpholinobenzhydrol '-Bis-N-methylpiperazinobenzhydrol, bis- (N-methyl-6

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Color Printing (AREA)
EP79101293A 1978-05-10 1979-04-30 Procédé de préparation de sulfinates de 4,4'-diaminobenzhydrol et de ses produits de substitution, et papier-calque contenant ces produits Expired EP0005251B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19782820486 DE2820486A1 (de) 1978-05-10 1978-05-10 Verfahren zur herstellung von sulfinaten des 4,4'diaminobenzhydrols und seiner substitutionsprodukte
DE2820486 1978-05-10

Publications (3)

Publication Number Publication Date
EP0005251A2 true EP0005251A2 (fr) 1979-11-14
EP0005251A3 EP0005251A3 (en) 1979-12-12
EP0005251B1 EP0005251B1 (fr) 1981-01-07

Family

ID=6039051

Family Applications (1)

Application Number Title Priority Date Filing Date
EP79101293A Expired EP0005251B1 (fr) 1978-05-10 1979-04-30 Procédé de préparation de sulfinates de 4,4'-diaminobenzhydrol et de ses produits de substitution, et papier-calque contenant ces produits

Country Status (3)

Country Link
EP (1) EP0005251B1 (fr)
JP (1) JPS54148762A (fr)
DE (2) DE2820486A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2478090A1 (fr) * 1980-03-14 1981-09-18 Ciba Geigy Ag Procede pour la preparation de sulfinates de composes du benzhydrol
EP0138159A2 (fr) * 1983-10-13 1985-04-24 Bayer Ag Matériel d'enregistrement thermosensible, préparation et emploi de polymères modifiés par l'acide comme accepteurs dans ce matériel

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3193404A (en) * 1959-03-19 1965-07-06 Davis Chester Associated dye salts and method of forming colored indicia therewith
FR2173268A1 (fr) * 1972-02-24 1973-10-05 Basf Ag

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3193404A (en) * 1959-03-19 1965-07-06 Davis Chester Associated dye salts and method of forming colored indicia therewith
FR2173268A1 (fr) * 1972-02-24 1973-10-05 Basf Ag

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2478090A1 (fr) * 1980-03-14 1981-09-18 Ciba Geigy Ag Procede pour la preparation de sulfinates de composes du benzhydrol
EP0138159A2 (fr) * 1983-10-13 1985-04-24 Bayer Ag Matériel d'enregistrement thermosensible, préparation et emploi de polymères modifiés par l'acide comme accepteurs dans ce matériel
EP0138159A3 (en) * 1983-10-13 1986-05-21 Bayer Ag Heat-sensitive registration material, preparation thereof, and use of acid-modified polymers in such materials

Also Published As

Publication number Publication date
JPS5735911B2 (fr) 1982-07-31
JPS54148762A (en) 1979-11-21
DE2820486A1 (de) 1979-11-15
EP0005251A3 (en) 1979-12-12
DE2960119D1 (en) 1981-02-26
EP0005251B1 (fr) 1981-01-07

Similar Documents

Publication Publication Date Title
DD280320A5 (de) Herstellung von zwischenprodukten der oxophthalazinyl-essigsaeuren mit benzothiazol oder anderen heterocyclischen seitenketten
EP0005251B1 (fr) Procédé de préparation de sulfinates de 4,4'-diaminobenzhydrol et de ses produits de substitution, et papier-calque contenant ces produits
EP0067352B1 (fr) Procédé de préparation d'acides S-aryl-thioglycoliques
EP0144668A1 (fr) Procédé pour la préparation de dérivés 3,4,6-trisubstitués de l'alkylthio-3 triazine, 1,2,4 one-5
DE2835450C3 (de) Verfahren zur Herstellung von 3,3-Bis-(4-dimethylaminophenyl)-6-dimethylaminophthalid (Kristallviolettlacton)
CH636332A5 (en) Process for preparing monoalkylated dihydroxybenzenes
EP0005475A1 (fr) Procédé de préparation du 4,4'-diaminobenzhydrol et de ses produits de substitution
DE2406972C3 (de) Verfahren zur Herstellung von 5-Sulfamoylanthranilsäuren
DE1266425C2 (de) Verfahren zur herstellung von anthrachinon-dispersionsfarbstoffen und deren verwendung
EP0327792B1 (fr) 3-(4-Amino-2-hydroxyphényl)-1-oxoisoindolénines, procédé pour leur préparation et leur saponification en acides 2-(4-amino-2-hydroxybenzoyl)-benzoiques
DE2215048A1 (de) Verfahren zur herstellung von 2eckige klammer auf bis-(4', 4"-dialkylamino)benzhydryl eckige klammer zu -5-aminobenzoesaeuren
DE2360202C2 (de) Verfahren zur Herstellung von 4-Chlor-benzothiazolverbindungen
EP0573999A1 (fr) Procédé pour la préparation d'esters tétroniques
EP0002721B1 (fr) Procédé de préparation d'hydrazines
DE2462459C3 (de) 5-Halogen-pyrazo!-4-carboxa!dehyde und Verfahren zu ihrer Herstellung
DE2335760A1 (de) 1,4-dihydro-4-oxo-chinolincarbonsaeure-derivate, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate
DE749975C (de) Verfahren zur Herstellung von N-Acetoacetylabkoemmlingen von Aminoverbindungen
DE2841825A1 (de) Verfahren zur herstellung von 1,2,3- thiadiazol-5-yl-harnstoffen
EP0090769A2 (fr) Procédé pour la préparation de la 1,2,5,6-tétrahydro-4H-pyrrolo(3,2,1-ij)-quinoléin-4-one et 5-halo-1,2,3-(1,2-dihydropyrrolo)-4-quinolones intermédiaires
AT242128B (de) Verfahren zur Herstellung von neuen Benzofuryl-(3)-äthylaminen und deren Salzen
DE1543625C (de) Verfahren zur Herstellung von 2 Amino 4 acylamino phenolathern
AT330781B (de) Verfahren zur herstellung von chinazolinonen
EP0602549A1 (fr) Acide 4-hydroxy-2,3,5-trifluorbenzoique et son procédé de préparation
DE2247496A1 (de) Verfahren zur herstellung von photographischen farbkupplern
DE1152420B (de) Verfahren zur Herstellung von Iminodibenzylderivaten

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

17P Request for examination filed
AK Designated contracting states

Designated state(s): CH DE FR GB

AK Designated contracting states

Designated state(s): CH DE FR GB

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Designated state(s): CH DE FR GB

REF Corresponds to:

Ref document number: 2960119

Country of ref document: DE

Date of ref document: 19810226

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19840331

Year of fee payment: 6

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19840402

Year of fee payment: 6

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 19840515

Year of fee payment: 6

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: CH

Effective date: 19860430

GBPC Gb: european patent ceased through non-payment of renewal fee
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19861231

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19870101

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Effective date: 19881118

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT