Classifications

• • 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
  • C09B11/00—Diaryl- or thriarylmethane dyes
  • C09B11/02—Diaryl- or thriarylmethane dyes derived from diarylmethanes
• • 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

• This invention relates to the N-halophenyl derivatives of "leucauramine having the general structure :"less; which may be I used as -color reacta nts because-they :turntoa dark blue 7 orggreen blue.color on con ing llltO adsorption contact with acidic svtypesvof: inorganic-42cmikaolin, beutonite, -alunrinumgsulfate;; zeolitemateri'ahsilica Cgels, magnesium trisilioate, and zinc sulphide, among others, and are useful in solution forxprintingtin eolor on paper eoated or-filled -with such adsorbents. Qtherwise, they are very' light-stable and annospherically stable both in their leucauramine forms and in their colored states.
• the leucauramine derivative is usually dissolved in a suitable solvent and carried as droplets in a hydrophilic colloid film coating on the rear of the ovenlyingshee't.”
• a hydrophilic colloid film coating on the rear of the ovenlyingshee't.
• halogenated derivatives of N-phenyl leucauramine are much more suitable for the manifold systems mentioned than the known utih'alogenated N-phenyl leucauramine, because they are less volatile, they have increased solubility in oil, and theya're much more stable com 2 pounds in the leuco form when subjected to atmospheric conditions and light.
• Such a record sheet is disclosedin U. S. Patent 2,505,470 which issued, on the application oh BarrttKtfir'een-fon April 25, 1950.
• a one process of nialcing the novel compounds consists of the steps of condensing molar equivalents of Michlers hydrol and a selectediehalogenated aniline in hot ethyl alcohol; concentrating :the reaction mixture as far as necessary to cause precipitation on cooling; filtering; purifying the crude material by treating a benzene solution of it with fullers earth and activated charcoal; and then precipitating out the reaction product by the addition of petroleum ether.
• the general equation for this reaction is as--. follows:
• m-chlorophenyl and p-chlorophenyl derivatives may be made by using in place of the o-chloroaniline used in the example, m-chloroaniline or the p-chloroaniline.
• o-bromop'henyl, m-brornophenyl, and p-bromophenyl derivatives may be made by using, instead of the chlorinated anilines, the selected brominated anilines, using the same relative molecular proportions.
• the dichlorophenyl, trichlorophenyl, tetrachlorophenyl, dibromophenyl, tribromophenyl, and tetrabromophenyl derivatives may be made in the same manner by using the selected halogenated aniline in the same molecular proportions.
• N-(2,4-dichlorophenyl)leucauramine is prepared by taking:
• trichlorophenyl, tribromophenyl, tetrachlorophenyl and tetrabromophenyl derivatives may be made simply by choosing the selected ha1o-' genated aniline for the reaction using the same molecular proportions.
• N-chloro-bromophenyl derivatives may be made in exactly the same way by using anilines in which both bromine and chlorine are substituted in the same phenyl group.
• R is taken from the group consisting of o-halo; m-halo; p-halo; 2,3-dihalo; 2,4-dahal0; 2,5-dihalo; 3,4- dihalo; 3,5-dihalo; 2,3,4-trihalo; 2,3,5-trihalo; 3,4,5-trihalo; 2,4,5-trihalo; and 2,3,4,5tetrahalo, and in which the halo substituent in any position may be taken from the group consisting of chlorine and bromine.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Priority Applications (3)

Applications Claiming Priority (1)

Publications (1)

Family

ID=24171919

Family Applications (1)

Country Status (2)

Cited By (10)

• 0
  • NL NL96329D patent/NL96329C/xx active
  • NL NL210412D patent/NL210412A/xx unknown
• 1955
  • 1955-11-01 US US544376A patent/US2828341A/en not_active Expired - Lifetime

Non-Patent Citations (1)

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