US2828341A - N-halophenyl derivatives of leucauramine - Google Patents

N-halophenyl derivatives of leucauramine Download PDF

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Publication number
US2828341A
US2828341A US544376A US54437655A US2828341A US 2828341 A US2828341 A US 2828341A US 544376 A US544376 A US 544376A US 54437655 A US54437655 A US 54437655A US 2828341 A US2828341 A US 2828341A
Authority
US
United States
Prior art keywords
leucauramine
derivatives
halophenyl
dibromo
grams
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.)
Expired - Lifetime
Application number
US544376A
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English (en)
Inventor
Clyde S Adams
Marjorie J Cormack
Frazier Mary Lou
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.)
NCR Voyix Corp
National Cash Register Co
Original Assignee
NCR Corp
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
Priority to NL96329D priority Critical patent/NL96329C/xx
Priority to NL210412D priority patent/NL210412A/xx
Application filed by NCR Corp filed Critical NCR Corp
Priority to US544376A priority patent/US2828341A/en
Application granted granted Critical
Publication of US2828341A publication Critical patent/US2828341A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US544376A 1955-11-01 1955-11-01 N-halophenyl derivatives of leucauramine Expired - Lifetime US2828341A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
NL96329D NL96329C (enrdf_load_stackoverflow) 1955-11-01
NL210412D NL210412A (enrdf_load_stackoverflow) 1955-11-01
US544376A US2828341A (en) 1955-11-01 1955-11-01 N-halophenyl derivatives of leucauramine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US544376A US2828341A (en) 1955-11-01 1955-11-01 N-halophenyl derivatives of leucauramine

Publications (1)

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US2828341A true US2828341A (en) 1958-03-25

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
US544376A Expired - Lifetime US2828341A (en) 1955-11-01 1955-11-01 N-halophenyl derivatives of leucauramine

Country Status (2)

Country Link
US (1) US2828341A (enrdf_load_stackoverflow)
NL (2) NL96329C (enrdf_load_stackoverflow)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2981733A (en) * 1958-05-12 1961-04-25 Allied Chem N-bis(p-dialkylaminophenyl)methyl derivatives of nitrogen-containing saturated heterocyclic compounds
US2983756A (en) * 1958-05-13 1961-05-09 Allied Chem Aliphatic amino derivatives of bis (p-dialkylaminophenyl) methane
US3001887A (en) * 1957-09-20 1961-09-26 Mead Corp Paper manufacture
US3225039A (en) * 1961-11-30 1965-12-21 Shell Oil Co N-trityl-morpholines and process for their production
US3239564A (en) * 1960-12-02 1966-03-08 Reeder Earl 2 n-substituted amino halobenzo-phenones
US3239366A (en) * 1961-11-21 1966-03-08 Ncr Co Thermotransfer sheet material and copying systems utilizing same
US3277173A (en) * 1963-06-13 1966-10-04 Mobay Chemical Corp Process for preparing aromatic polyamines
US3336296A (en) * 1962-10-26 1967-08-15 American Home Prod Preparation of 5-substituted-2h-1, 4-benzodiazepin-2-one-4-oxides
US4927802A (en) * 1988-12-09 1990-05-22 Ppg Industries, Inc. Pressure-sensitive multi-part record unit
US5194390A (en) * 1988-07-05 1993-03-16 Miles Inc. Composition for the assay of albumin

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3001887A (en) * 1957-09-20 1961-09-26 Mead Corp Paper manufacture
US2981733A (en) * 1958-05-12 1961-04-25 Allied Chem N-bis(p-dialkylaminophenyl)methyl derivatives of nitrogen-containing saturated heterocyclic compounds
US2983756A (en) * 1958-05-13 1961-05-09 Allied Chem Aliphatic amino derivatives of bis (p-dialkylaminophenyl) methane
US3239564A (en) * 1960-12-02 1966-03-08 Reeder Earl 2 n-substituted amino halobenzo-phenones
US3239366A (en) * 1961-11-21 1966-03-08 Ncr Co Thermotransfer sheet material and copying systems utilizing same
US3225039A (en) * 1961-11-30 1965-12-21 Shell Oil Co N-trityl-morpholines and process for their production
US3336296A (en) * 1962-10-26 1967-08-15 American Home Prod Preparation of 5-substituted-2h-1, 4-benzodiazepin-2-one-4-oxides
US3277173A (en) * 1963-06-13 1966-10-04 Mobay Chemical Corp Process for preparing aromatic polyamines
US5194390A (en) * 1988-07-05 1993-03-16 Miles Inc. Composition for the assay of albumin
US4927802A (en) * 1988-12-09 1990-05-22 Ppg Industries, Inc. Pressure-sensitive multi-part record unit

Also Published As

Publication number Publication date
NL96329C (enrdf_load_stackoverflow)
NL210412A (enrdf_load_stackoverflow)

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