GB1431493A - Dye precursors for pressure-sensitive recording material - Google Patents

Dye precursors for pressure-sensitive recording material

Info

Publication number
GB1431493A
GB1431493A GB2701773A GB2701773A GB1431493A GB 1431493 A GB1431493 A GB 1431493A GB 2701773 A GB2701773 A GB 2701773A GB 2701773 A GB2701773 A GB 2701773A GB 1431493 A GB1431493 A GB 1431493A
Authority
GB
United Kingdom
Prior art keywords
carbon atoms
pyridine
ammonia
dye precursor
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.)
Expired
Application number
GB2701773A
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.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik 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 BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB1431493A publication Critical patent/GB1431493A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Color Printing (AREA)
  • Pyridine Compounds (AREA)

Abstract

1431493 Compounds used in pressure sensitive recording or copying materials BADISCHE ANILIN- & SODA-FABRIK AG 6 June 1973 [7 June 1972] 27017/73 Heading C4P [Also in Division D2] The dye precursor in a pressure-sensitive recording or copying material is a 4-(41-aminophenyl)-pyridine of general formula in which R<SP>1</SP> and R<SP>2</SP> are each independently hydrogen or an alkyl or aryl group of one to eight carbon atoms which may bear alkoxy or halogen as a substitute; R<SP>3</SP> is hydrogen or alkyl of one to five carbon atoms; R<SP>4</SP> is alkyl of 1-4 carbon atoms, haloalkyl of 1-4 carbon atoms, cyanalkyl of which the alkyl moiety contains from 1-4 carbon atoms, an aryl or aralkyl of one to eight carbon atoms which may bear alkoxy as a substitute; R<SP>5</SP> and R<SP>6</SP> are each independently hydrogen or carbalkoxy or two to five carbon atoms; and R<SP>3</SP> and R<SP>4</SP> may be closed into a ring. Many examples of specified radicals are given. The dye precursor may be prepared by many conventional methods, for example by condensation of 4-(4<SP>1</SP>-aminophenyl)- pyrylium salts with ammonia or agents which disengage ammonia or by condensation of a 4-aminobenzaldehyde of the general formula or an arylvinylketone of the formula with a ketone of formula in the presence of ammonia or an agent which disengages ammonia. A list of preferred starting materials are given. In one example for the preparation of the dye precursor, pyridine, benzoyl chloride and copper powder are heated for an hour at 100-105‹ C. Methylbenzylaniline is added at 70-80‹ C. and heating at 100-105‹ C. continued. Toluene is added, the resultant precipitate being dissolved in hydrochloric acid. After clarification and recrystallization from ethanol and water, 4-(4<SP>1</SP>-methylbenzylaminophenyl)-pyridine is obtained. In a second example, p-dimethylaminobenzaldehyde, acetophenone and ammonium acetate are heated under reflux in glacial acetic acid. The precipitate is recrystallized from ethanol being 2,6-diphenyl-4-(41-dimethylaminophenyl)-pyridine. The 4-(4<SP>1</SP>-aminophenyl) pyridines may be mixed with another dye precursor, e.g. crystal violet lactone, N-phenyl leucoauramine, N- benzoyl-leucomethylene blue and, in dissolved form micro-encapsulated. The capsules are applied together with a binder to paper. A visible trace on another, acidic, surface results when the capsules are ruptured by pressure.
GB2701773A 1972-06-07 1973-06-06 Dye precursors for pressure-sensitive recording material Expired GB1431493A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19722227597 DE2227597C2 (en) 1972-06-07 1972-06-07 Pressure sensitive recording material

Publications (1)

Publication Number Publication Date
GB1431493A true GB1431493A (en) 1976-04-07

Family

ID=5847008

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2701773A Expired GB1431493A (en) 1972-06-07 1973-06-06 Dye precursors for pressure-sensitive recording material

Country Status (10)

Country Link
JP (1) JPS539127B2 (en)
BE (1) BE800522A (en)
CA (1) CA1002819A (en)
CH (1) CH578949A5 (en)
DD (1) DD104474A5 (en)
DE (1) DE2227597C2 (en)
FR (1) FR2188509A5 (en)
GB (1) GB1431493A (en)
IT (1) IT988214B (en)
SE (1) SE400508B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5518647A (en) * 1978-07-26 1980-02-08 Matsushita Electric Ind Co Ltd Light transmittable particle for forming color images
US4372582A (en) * 1981-03-30 1983-02-08 Minnesota Mining And Manufacturing Company Stabilizer for electron doner-acceptor carbonless copying systems
JP4320811B2 (en) * 1998-12-07 2009-08-26 コニカミノルタホールディングス株式会社 Organic electroluminescence device

Also Published As

Publication number Publication date
DD104474A5 (en) 1974-03-12
JPS539127B2 (en) 1978-04-04
DE2227597B1 (en) 1974-01-17
FR2188509A5 (en) 1974-01-18
BE800522A (en) 1973-12-06
IT988214B (en) 1975-04-10
DE2227597A1 (en) 1974-01-17
JPS4949716A (en) 1974-05-14
DE2227597C2 (en) 1974-08-15
CH578949A5 (en) 1976-08-31
CA1002819A (en) 1977-01-04
SE400508B (en) 1978-04-03

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee