US3692800A - Photochromic compound - Google Patents
Photochromic compound Download PDFInfo
- 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
- Authority
- US
- United States
- Prior art keywords
- group
- compound
- carbon atoms
- alkyl group
- photochromic
- 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
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 45
- 125000000217 alkyl group Chemical group 0.000 abstract description 19
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 10
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 10
- 125000005843 halogen group Chemical group 0.000 abstract description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 abstract description 8
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 3
- 229910001864 baryta Inorganic materials 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- -1 polyethylene terephthalate Polymers 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- HGKHVFKBOHFYSS-UHFFFAOYSA-N 2-hydroxy-3-methoxy-5-nitrobenzaldehyde Chemical compound COC1=CC([N+]([O-])=O)=CC(C=O)=C1O HGKHVFKBOHFYSS-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 150000001450 anions Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical class OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- 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.
Landscapes
- 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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP43079152A JPS4948632B1 (enrdf_load_stackoverflow) | 1968-10-30 | 1968-10-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3692800A true US3692800A (en) | 1972-09-19 |
Family
ID=13681972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US872604A Expired - Lifetime US3692800A (en) | 1968-10-30 | 1969-10-30 | Photochromic compound |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3692800A (enrdf_load_stackoverflow) |
| JP (1) | JPS4948632B1 (enrdf_load_stackoverflow) |
| BE (1) | BE740831A (enrdf_load_stackoverflow) |
| DE (1) | DE1954041C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2021914A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1246186A (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7300727B2 (en) | 2004-04-29 | 2007-11-27 | Xerox Corporation | Method for forming temporary image |
| US7205088B2 (en) | 2004-04-29 | 2007-04-17 | Xerox Corporation | Reimageable medium with light absorbing material |
| US7214456B2 (en) | 2004-04-29 | 2007-05-08 | Xerox Corporation | Reimageable medium |
Citations (1)
| 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 |
-
1968
- 1968-10-30 JP JP43079152A patent/JPS4948632B1/ja active Pending
-
1969
- 1969-10-27 DE DE1954041A patent/DE1954041C3/de not_active Expired
- 1969-10-27 BE BE740831D patent/BE740831A/xx unknown
- 1969-10-28 GB GB52809/69A patent/GB1246186A/en not_active Expired
- 1969-10-29 FR FR6937086A patent/FR2021914A1/fr not_active Withdrawn
- 1969-10-30 US US872604A patent/US3692800A/en not_active Expired - Lifetime
Patent Citations (1)
| 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 |
|---|---|
| DE1954041C3 (de) | 1974-08-01 |
| GB1246186A (en) | 1971-09-15 |
| BE740831A (enrdf_load_stackoverflow) | 1970-04-01 |
| DE1954041A1 (de) | 1970-05-14 |
| DE1954041B2 (de) | 1973-12-20 |
| FR2021914A1 (enrdf_load_stackoverflow) | 1970-07-24 |
| JPS4948632B1 (enrdf_load_stackoverflow) | 1974-12-23 |
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