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
  • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
  • C09B11/26—Triarylmethane dyes in which at least one of the aromatic nuclei is heterocyclic
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
  • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
  • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
  • B01J13/02—Making microcapsules or microballoons
  • B01J13/025—Applications of microcapsules not provided for in other subclasses
• • 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
  • B41M5/145—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
• • 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
  • B41M5/145—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
  • B41M5/1455—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring characterised by fluoran compounds

Definitions

• a pressure-sensitive copying paper comprising a support having coated thereon microcapsules containing an organic solvent solution of a compound which, when in contact with an electron acceptable solid acid, forms a color dye and is represented by the following formula:
• alkyl group having from one to 17 carbon atoms, an aryl group, an amino group, an acylamino group and an alkoxy group having from one to five carbon atoms.
• This invention relates to a pressure-sensitive copying paper and in particular, it is concerned with a pressure-sensitive copying paper using as a color former a compound represented by the following general formula:
• R and R are alkyl groups of one to five carbon atoms or benzyl groups
• X is an alkyl group of one to five carbon atoms or an aryl group
• Y is an alkyl group of one to 17 carbon atoms, an aryl group, an amino group, an acylamino group or an alkoxy group.
• Ordinary pressure-sensitive copying paper consists of an upper paper onto which is coated a substantially colorless organic compound having an electron-donating property and a color forming reactivity (hereinafter referred to as a color former") dissolved in an organic solvent and incorporated in microcapsules and a lower paper, onto which is coated electron-acceptable solid acid. If necessary, an intermediate paper layer is provided onto one side thereof is coated the colorformer-containing microcapsules and on the other side thereof is coated a solid acid, and a support on one side of which the microcapsules and solid acid are coated.
• a color former color forming reactivity
• the papers are pressed locally in such a manner that the microcapsules-containing layer and the solid acid-containing layer are contacted, whereby the microcapsules in this pressurized area are broken and the color former is reacted with the solid acid, thus color forming.
• the paper may be pressed for color forming by means of a typewriter, for example.
• color formers coloring in red and blue are the following: leuco triphenylmethane derivatives, leuco methylene blue acyl derivatives, and triphenylmethane and xanthene phthalide derivatives having lactone rings.
• color formers coloring in yellow orange to orange red there are not many color formers coloring in yellow orange to orange red.
• These color formers have the following disadvantages. That is to say, o-hydroxybenzalacetophenone has a low color forming density. 2-(4-hydroxystyryl)-3,3-dimethyl- 3I-l-indole or 2-(4-acetamidestry1)-3,3-dimethyl-3H-indole (cf. Japan Pat. publication No.
• 21033/1966 has a high color forming density and relatively strong light resistance after color forming, but the light resistance before color forming and water resistance after color forming are weak. If a color former coloring in yellow-orange to orange-red is obtained which has a higher color density, higher color forming speed and stronger light resistance and water resistance before and after color forming than those known in the art, a pressuresensitive copying paper coloring in yellow-orange to orangered as well as a pressure-sensitive copying paper coloring in an optional color such as black or blue-black used together with a known color former coloring in red or blue will be given. This advantage enlarges the application of pressure-sensitive copying papers.
• a pressure-sensitive copying paper according to the present invention using the compound of the foregoing general formula has an excellent stability in air before color forming, is free from coloring and lowering of the color forming ability, colored in yelloworange to orange-red immediately when contacted with an electron-accepting solid, acid, thus resulting in a high color density and is strongly resistant to light and water after color forming,
• a known color former coloring in red or blue it colors in various colors such as black and blue-black without being desensitized.
• the pressure-sensitive copying paper of the present invention For the production of the pressure-sensitive copying paper of the present invention using the compound represented by the general formula, a method of making microcapsules by utilizing the complexed coacervation is employed, for example, which is disclosed in US. Pat. Nos. 2,548,366, 2,800,457 and 2,800,458 as being well-known to those skilled in the art.
• the instant invention is characterized by the use of the compound represented by the foregoing general formula as a color former.
• the characteristics of the pressure-sensitive copying paper are independent from the production method thereof.
• the amount of the color former used is generally 0.5-5 percent by weight based on the organic solvent.
• EXAMPLE 1 Three grams of each of the color formers (I)-(Il) was The color former was dissolved in g. of trichlorodiphenyl. To the resulting solution were added 20 g. of gum arabic and g. of water at 50 C. to given an emulsion, further, 20 g. of acid-treated gelatin and 160 g. of water and then acetic acid were added, while stirring to adjust the pH to 5. Then, 500 g. of water was added thereto to advance the coacervation to form a thickened liquid film of gelatin-gum arabic around the oil drop of trichlorodiphenyl dissolving the color former. After adjusting the pH to 4.4, 3.8 g.
• the thus capsulized liquid was coated onto a sheet of paper by roll coating or by air knife coating and then dried.
• the coated paper upper paper
• another sheet of paper lower paper
• an electron-accepting solid acid such as acid clay. active clay, attapulgite, zeolite or bentonite and pressed by means of a pencil or typewriter, there instantaneously occurred a thick color formation on the pressed area of the lower sheet of paper.
• a yellow-orange color was noted in the color formers (l), (2), (4,), (5), (6) and (10) orange in (3). (7). and (11); and orange-red in (8) and (9).
• These color formed dyes were scarcely faded even though exposed to direct sunlight for a long time or wetted with water.
• EXAMPLE 2 l The pressure-sensitive copying paper as claimed in claim The procedure of example 1 was repeated, except that 1.51 l saldh electromacgpiable i a memtier g. of the color former (2) was used with the known color for- Se ecte mm t B group conslstmg 0 an acid c an acme mers, i.e., 0.3 g. of Benzoyl Leuco Methylene blue, 0.5 g. of i g l Succlmc acid tanmc l hite Green Lactone 0 7 of Cr stal Violet Lactone lc an Pema? Drop Ma ac 8- y t 5 4.
• a pressure-sensitive copying paper comprising a support 8 'P "Y auramme and 8- of Rhodamme B having coated thereon an electron-acceptable solid acid and Anilinolactam.
• EXAMPLE 3 R The procedure of example 1 was repeated, except that 0.3 N- f g. of the color former (4) and 0.7 g. of the color forrner (8) were used with 0.5 g. of Benzoyl Leuco Methylene Blue, 2.0 g.
• a pressure-sensitive copying paper comprising and under paper having coated thereon an electron-acceptable solid acid and an upper paper having coated thereon microcapsules containing an organic solvent solution of a compound which is in contact with said electron-acceptable solid acid to form a color dye and is represented by the following formula:
• a pressure-sensitive copying paper comprising a support X having coated thereon microcapsules containing an organic i; ⁇ solvent solution of a compound which, when in contact with N N an electron acceptable solid acid, forms a color dye and is i represented by the following formula: C Y
• R and R each represents a member selected from I the group consisting of an alkyl group having from one to five carbon atoms and a benzyl group
• X represents a member selected from the group consisting of an alkyl group having from one to five carbon atoms and an aryl group
• Y wherein R and R each represents a member selected from represents a member selected from the group consisting of an the group consisting of an alkyl group having from one to five alkyl group having from one to 17 carbon atoms, an aryl carbon atoms and a benzyl group
• X represents a member group, an amino group, an acylamino group and an alkoxy selected from the group consisting of an alkyl group having group having from one to five carbon atoms.

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

Applications Claiming Priority (1)

Publications (1)

Family

ID=12841656

Family Applications (1)

Country Status (4)

Cited By (35)

Families Citing this family (1)

Citations (3)

• 1969
  • 1969-07-14 GB GB1264636D patent/GB1264636A/en not_active Expired
  • 1969-07-14 IE IE960/69A patent/IE33222B1/xx unknown
  • 1969-07-14 ES ES369481A patent/ES369481A1/es not_active Expired
  • 1969-07-15 US US842008A patent/US3617335A/en not_active Expired - Lifetime

Patent Citations (3)

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