US3692800A - Photochromic compound - Google Patents

Photochromic compound Download PDF

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Publication number
US3692800A
US3692800A US872604A US3692800DA US3692800A US 3692800 A US3692800 A US 3692800A US 872604 A US872604 A US 872604A US 3692800D A US3692800D A US 3692800DA US 3692800 A US3692800 A US 3692800A
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US
United States
Prior art keywords
group
compound
carbon atoms
alkyl group
photochromic
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Expired - Lifetime
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US872604A
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English (en)
Inventor
Hisatake Ono
Chiaki Osada
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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Application filed by Fuji Photo Film Co Ltd filed Critical Fuji Photo Film Co Ltd
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/685—Compositions containing spiro-condensed pyran compounds or derivatives thereof, as photosensitive substances

Definitions

  • R and R each is an alkyl group having one to five carbon atoms or a phenyl group
  • R is a hydrogen atom, an alkyl group having one to five carbon atoms, a halogen atom, a nitro group, a cyano group, a carboxyl group substituted by an alkyl group having one to five carbon atoms, or an alkoxyl group
  • R and R each is a hydrogen atom, a nitro group, a halogen atom, a formyl group or an alkoxyl group
  • X is a cyano group or a carboxyl group substituted by an alkyl group having one to five carbon atoms
  • n is l to 4.
  • the present invention relates to photochromic compounds and compositions.
  • a compound represented by the above formula, in which X is a hydrogen atom, is publicly known as a photochromic compound.
  • the compound is remarkably affected by polarity during practical use as a photochromic compound, and therefore, has the defeet that the selection range of a high molecular weight material used as a carrier and a solvent used in combination therewith is very narrow.
  • R and R each is an alkyl group having one to five carbon atoms or a phenyl group
  • R is a hydrogen atom, an alkyl group having one to five carbon atoms, a halogen atom, a nitro group, a cyano group, a carboxyl group substituted by an alkyl group having one to five carbon atoms, or an alkoxyl group
  • R, and R each is a hydrogen atom, a nitro group, a halogen atom, a formyl group or an alkoxyl group
  • X is a cyano group or a carboxyl group substituted by an alkyl group having one to five carbon atoms
  • n is l to 4.
  • Novel compositions are also provided.
  • Objects of the invention are to provide improved photochromic compounds and compositions.
  • the present invention relates to a photochromic compound represented by the formula halogen atom, a nitro group, a cyano group, a carboxyl group substituted by an alkyl group having one to five carbon atoms, or an alkoxyl group, R, and R each is a hydrogen atom, a nitro group, a halogen atom, a formyl group or an alkoxyl group, X is a cyano group or a carboxyl group substituted by an alkyl group having one to five carbon atoms, and n is I to 4.
  • the compounds represented by the above formula are colorless when dissolved in a non-polar solvent such as benzene, toluene, etc., and turn greenish blue when irradiated with ultraviolet rays.
  • common paper, baryta paper, high molecular weight resinous support, such as polyethylene terephthalate, cellulose triacetate films, etc., glass metals, etc. can be used.
  • composition of the present invention is colorless in its ordinary state, but, upon being irradiated with sun light, ultraviolet rays from a mercury lamp, etc. thereon, turns blue or bluish green. The compound returns to its original stage upon being allowed to stand in the dark or upon being heated.
  • FIG. 1 is a graph showing the change in the absorption spectrum of a film coated with the photochromic composition of the present invention and dried, the absorption spectrum being shown both before and after irradiation with ultraviolet rays.
  • FIG. I shows the change of absorption spectrum of the compound represented by the above formula in which X is a nitrile group, R, and R are a methyl group, R. is 5 CH R is 6'-NO and R is a hydrogen atom.
  • numeral I shows the change before irradiation with ultraviolet rays and numeral 2 shows the changes after irradiation.
  • a mercury lamp made by Toshiba SHE-I00 was used as the light source.
  • the compound represented by the above formula is generally obtained by dissolving a 2-methyl indolenine derivative and a salicylaldehyde derivative in absolute ethanol, adding triethylamine thereto, refluxing, distilling out the solvent after reaction, and appropriately treating the residue.
  • Photochromic materials using the present compound are exemplified by photochromic materials used for photography and printing, which are obtained by coating the above-described composition onto a high molecular weight resinous base, or a baryta paper, etc.; photochromic materials for furniture, obtained by coating a curtain, glass, etc.; and a photochromic material used as a filter, etc.
  • the photochromic material obtained by coating a solution of thiscompound in benzene-polystyrene onto a polyethylene terephthalate film and then drying was colorless in its ordinary state, but, upon being contacted with a photographic positive film or negative film and irradiated with ultraviolet rays, was colored to give a blue positive or negative image at those portions where the light was transmitted.
  • the image thus obtained returned to its colorless state upon being allowed to stand in the dark.
  • EXAMPLE 2 4.l g. of 1-'y-ethylcarboxypropyl-2,3,3-triethylindolenium bromide and 2.1 g. of S-nitrosalicylaldehyde were reacted in the same manner as in Example 1 to obtain 2 g. of the yellow-white crystals of l-y-ethylcarboxypropyl-3,3-dimethyl6-nitrospiro(indoline-2,2'-2' h-chromene). its melting point was 1 17 to l 18C.
  • EXAMPLE 3 3.5 g. of l-'y-cyanopropyl-2,3,3-trimethyl chloroindolenium bromide and 2 g. of 3-methoxy-5- nitro-salicylaldehyde were reacted in the same manner as in Example 1 to obtain l.8 g. of the faint green crystals of l-'y-cyanopropyl-3,3-dimethyl-6'-nitro-8'- methoxyspiro (indoline-2,2'-2'H-chromene). lts melting point was 173 to l74C. A solution of this compound in benzene was colorless, but immediately turned blue upon being irradiated with sun light, and returned to colorless soon after being placed in the dark.
  • EXAMPLE 4 3.4 g. of l-'y-cyanopropyl-2,3,S-trimethyl-S- chloroindolenium bromide and 1.7 g. of S-nitrosalicylaldehyde were reacted in the same manner as in Example to obtain 2.0 g. of the yellow crystals of l-ycyanopropyl-3,3-dimethyl-5-chloro-6'-nitrospiro(indoline-2,2'-2'l-l-chromene). lts melting point was 198 to 200C. The properties of this compound were almost the same as that in Example 1.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
US872604A 1968-10-30 1969-10-30 Photochromic compound Expired - Lifetime US3692800A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP43079152A JPS4948632B1 (US06605200-20030812-C00035.png) 1968-10-30 1968-10-30

Publications (1)

Publication Number Publication Date
US3692800A true US3692800A (en) 1972-09-19

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US872604A Expired - Lifetime US3692800A (en) 1968-10-30 1969-10-30 Photochromic compound

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US (1) US3692800A (US06605200-20030812-C00035.png)
JP (1) JPS4948632B1 (US06605200-20030812-C00035.png)
BE (1) BE740831A (US06605200-20030812-C00035.png)
DE (1) DE1954041C3 (US06605200-20030812-C00035.png)
FR (1) FR2021914A1 (US06605200-20030812-C00035.png)
GB (1) GB1246186A (US06605200-20030812-C00035.png)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7300727B2 (en) 2004-04-29 2007-11-27 Xerox Corporation Method for forming temporary image
US7214456B2 (en) * 2004-04-29 2007-05-08 Xerox Corporation Reimageable medium
US7205088B2 (en) 2004-04-29 2007-04-17 Xerox Corporation Reimageable medium with light absorbing material

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3242122A (en) * 1961-09-18 1966-03-22 Ncr Co Thermo-colorable record copy sheet and coating composition

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3242122A (en) * 1961-09-18 1966-03-22 Ncr Co Thermo-colorable record copy sheet and coating composition

Also Published As

Publication number Publication date
BE740831A (US06605200-20030812-C00035.png) 1970-04-01
JPS4948632B1 (US06605200-20030812-C00035.png) 1974-12-23
GB1246186A (en) 1971-09-15
DE1954041C3 (de) 1974-08-01
DE1954041A1 (de) 1970-05-14
FR2021914A1 (US06605200-20030812-C00035.png) 1970-07-24
DE1954041B2 (de) 1973-12-20

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