JPH0436381A - Photochromic composition - Google Patents
Photochromic compositionInfo
- Publication number
- JPH0436381A JPH0436381A JP2139882A JP13988290A JPH0436381A JP H0436381 A JPH0436381 A JP H0436381A JP 2139882 A JP2139882 A JP 2139882A JP 13988290 A JP13988290 A JP 13988290A JP H0436381 A JPH0436381 A JP H0436381A
- Authority
- JP
- Japan
- Prior art keywords
- color
- photochromic
- leuco dye
- spiropyran
- light
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 19
- 230000002441 reversible effect Effects 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 4
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 4
- 150000002500 ions Chemical class 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 abstract 2
- 238000000862 absorption spectrum Methods 0.000 description 7
- 239000003086 colorant Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000010586 diagram Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- OALHHIHQOFIMEF-UHFFFAOYSA-N 3',6'-dihydroxy-2',4',5',7'-tetraiodo-3h-spiro[2-benzofuran-1,9'-xanthene]-3-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 OALHHIHQOFIMEF-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
Landscapes
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は光を照射することによって種々の色に呈色し、
その後暗所に放置することによって消色する可逆性フォ
トクロミック組成物に関するものである。[Detailed Description of the Invention] [Industrial Application Field] The present invention is characterized by the fact that the invention changes color by irradiating it with light,
The present invention relates to a reversible photochromic composition whose color disappears by leaving it in a dark place.
従来の７オトクロミツク組成物は光によって変色する化
合物を単独で用いている。したがって、変色する色相に
は限りがあり、また、変色後の色相が異なるフォトクロ
ミック化合物を製造するためには、そのような発色をす
る化合物を合成する必要があるため、多大な時間と労力
を要する。また、呈色濃度を高めるためには高価なフォ
トクロミック化合物を多量に用いる必要がある。Conventional 7 otochromic compositions use only a compound that changes color when exposed to light. Therefore, there is a limit to the hue that can change color, and in order to produce photochromic compounds that have different hues after color change, it is necessary to synthesize compounds that produce such color, which requires a great deal of time and effort. . Furthermore, in order to increase the color density, it is necessary to use a large amount of expensive photochromic compounds.
上述のように、従来の技術では変色する色には限りがあ
り、変色後の色相が異なり、また呈色濃度の大きい化合
物を合成するのは困難であった。As described above, in the conventional techniques, there is a limit to the colors that can change, the hue after the change is different, and it is difficult to synthesize a compound that has a large color density.
本発明では少量の７オトクロミツク化合物を用いて種々
の色に呈色し、また呈色濃度の大きいフォトクロミック
組成物を簡便に製造する手段を提供する。The present invention provides a means for easily producing photochromic compositions that can be colored in various colors and have a high color density using a small amount of a 7-otochromic compound.
本発明では光によってイオン的に開裂するスピロピラン
等のフォトクロミック化合物と、種々の色に呈色するロ
イコ染料を組合せて使用する。即ち、スピロピランは光
照射によってイオン的に開裂し、ロイコ染料と反応する
ことによって種々の色に呈色するが、暗所に放置するこ
とによって元のスピロピランとロイコ染料に分離して無
色となる。色を変えるためにはロイコ染料の種類を変え
ればよい。ロイコ染料としてはフェノールフタレーン類
、フルオレセイン類等種々の化合物を用いることができ
る。In the present invention, a photochromic compound such as spiropyran that is ionically cleaved by light and a leuco dye that develops various colors are used in combination. That is, spiropyran is ionically cleaved by light irradiation and develops various colors by reacting with leuco dye, but when left in a dark place, it separates into the original spiropyran and leuco dye and becomes colorless. To change the color, you can change the type of leuco dye. As the leuco dye, various compounds such as phenolphthalenes and fluoresceins can be used.
上記のように調製したフォトクロミック組成物はフォト
クロミック化合物とロイコ染料とが反応することによっ
て呈色する。反応式を第１図に示す。即ち、１１１スピ
ロピランとロイコ染料（フェノールフタレーン）を混合
し、溶剤に溶解したフォトクロミック組成物は無色の液
体である。しかし、（２）光照射によりスピロピランが
イオン的に開裂し、（３）このイオン的に開裂したスピ
ロピランは直ちにロイコ染料と反応して赤紫色に発色す
る。なお、（３）の構造を有する化合物は暗所に放置す
ることによす、元のスピロピランとロイコ染料に分離し
無色となる。この際、ロイコ染料の種類を変えることに
よって種々の色のフォトクロミック組成物を簡便に製造
することができる。また、親和性の異なるフォトクロミ
ック化合物とロイコ染料を用いることにより、発色時間
及び消色時間の異なるものが製造できる。The photochromic composition prepared as described above develops color due to the reaction between the photochromic compound and the leuco dye. The reaction formula is shown in Figure 1. That is, a photochromic composition in which 111 spiropyran and leuco dye (phenolphthalene) are mixed and dissolved in a solvent is a colorless liquid. However, (2) spiropyran is ionically cleaved by light irradiation, and (3) this ionically cleaved spiropyran immediately reacts with the leuco dye to develop a reddish-purple color. Note that when the compound having the structure (3) is left in a dark place, it separates into the original spiropyran and the leuco dye and becomes colorless. At this time, photochromic compositions of various colors can be easily produced by changing the type of leuco dye. Furthermore, by using a photochromic compound and a leuco dye that have different affinities, it is possible to produce products with different color development times and color erasure times.
実施例によって本発明をさらに詳細に説明するが、本発
明はこの例によってなんら限定されるものではない。The present invention will be explained in more detail with reference to examples, but the present invention is not limited to these examples in any way.
東京化成製Ｔ３６６（１，３，３−トリメチルインドリ
ノ−６′−二トロベンゾピリロスピラン） Ｏ，ＤＯ２
ｅとフェノールフタレーン２０９をテトラヒドロフラン
に溶解して１００ｍ１溶液とした。前記Ｔ３６６の単独
溶液では紫外線を照射すると青紫色に発色するが、Ｔａ
２Ｏとフェノールフタレーンの混合物に紫外線を照射す
ると赤紫色に発色する。Ｔａ２Ｏの紫外線照射前後の吸
収スペクトルを第２図に示す。Tokyo Kasei T366 (1,3,3-trimethylindolino-6'-nitrobenzopyrillospiran) O,DO2
e and phenolphthalene 209 were dissolved in tetrahydrofuran to make a 100 ml solution. The T366 alone solution develops a blue-purple color when irradiated with ultraviolet rays, but Ta
When a mixture of 2O and phenolphthalene is irradiated with ultraviolet light, it develops a reddish-purple color. Figure 2 shows the absorption spectra of Ta2O before and after UV irradiation.
また、Ｔａ２Ｏとフェノールフタレーンの混合物の紫外
線照射前後の吸収スペクトルを第３図に示す。Further, FIG. 3 shows the absorption spectra of a mixture of Ta2O and phenolphthalene before and after irradiation with ultraviolet rays.
Ｔ３６６単独の場合紫外線照射後の吸収スペクトルのピ
ークは５８０ ｎｍであるが、Ｔａ２Ｏとフェノールフ
タレーンの混合物の場合、吸収スペクトルのピークは５
４５ｎｍに移動している。In the case of T366 alone, the peak of the absorption spectrum after UV irradiation is 580 nm, but in the case of a mixture of Ta2O and phenolphthalene, the peak of the absorption spectrum is 580 nm.
It has moved to 45 nm.
なお、このフォトクロミック組成物はフォトクロミック
化合物を単独で用いたものよりも消色時間は長いが、暗
所で徐々に消色して元の無色となる。Although this photochromic composition has a longer decoloring time than one using a photochromic compound alone, it gradually decolors in a dark place and returns to its original colorless state.
上述したように、フォトクロミック化合物とロイコ染料
を組合せることによって、種々の色相に発色する可逆性
フォトクロミック組成物を簡便に製造することができる
。発色後の色相を変えるためには、ロイコ染料の種類を
変えればよい。また、この組成物はロイコ染料を用いて
いるため呈色濃度は大きい。As described above, by combining a photochromic compound and a leuco dye, a reversible photochromic composition that develops colors in various hues can be easily produced. In order to change the hue after coloring, the type of leuco dye can be changed. Furthermore, since this composition uses a leuco dye, the color density is high.
なお、この組成物は溶液状であるため、マイクロカプセ
ル化することにより、種々の材料に応用することが可能
である。例えばマイクロカプセル化した材料を、紙、プ
ラスチック等に塗布することにより特殊な効果を有する
可逆性の光変色性材料を製造することができ、偽造防止
、真偽判別等に利用できる。また、玩具等の用途にも利
用できる。Note that since this composition is in the form of a solution, it can be applied to various materials by microcapsulating it. For example, a reversible photochromic material with special effects can be produced by applying microencapsulated material to paper, plastic, etc., and can be used for counterfeit prevention, authenticity determination, etc. It can also be used for toys, etc.
第１図はスピロピラン類とフェノールフタレーンとの一
般的な反応式を示す図。
第２図はＴａ２Ｏ（１，３，３−）ツメチルインドリノ
−６′−二トロペンゾビリ口スビラン〕の紫外線照射前
後の吸収スペクトルを示す図。
第３図はＴａ２Ｏとフェノールフタレーンの混合物の紫
外線照射前後の吸収スペクトルを示す図。
（フェノールフタレーン）
第１図
（赤紫色）
スピロピラン（Ｔ３６６）とフェノールフタレイ／の反
応式Ｔ３６６の吸収スペク
トルFIG. 1 is a diagram showing a general reaction formula between spiropyrans and phenolphthalene. FIG. 2 is a diagram showing the absorption spectra of Ta2O(1,3,3-)tumethylindolino-6'-nitropenzobirigachisubiran] before and after irradiation with ultraviolet rays. FIG. 3 is a diagram showing the absorption spectra of a mixture of Ta2O and phenolphthalene before and after irradiation with ultraviolet rays. (phenolphthalene) Figure 1 (red purple) Absorption spectrum of reaction formula T366 between spiropyran (T366) and phenolphthalei/
Claims (1)
トクロミック化合物とフェノールフタレーン、フルオレ
セイン等のイオンによって発色するロイコ染料を組合せ
、溶剤を用いて溶解した可逆性フォトクロミック組成物
。 ２、上記組成物をマイクロカプセル化して製造した可逆
性フォトクロミック材料。[Scope of Claims] 1. A reversible photochromic composition in which a photochromic compound that is ionically cleaved by light, such as spiropyran, and a leuco dye that develops color with ions, such as phenolphthalene or fluorescein, are combined and dissolved using a solvent. 2. A reversible photochromic material produced by microencapsulating the above composition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13988290A JP2813763B2 (en) | 1990-05-31 | 1990-05-31 | Photochromic composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13988290A JP2813763B2 (en) | 1990-05-31 | 1990-05-31 | Photochromic composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0436381A true JPH0436381A (en) | 1992-02-06 |
| JP2813763B2 JP2813763B2 (en) | 1998-10-22 |
Family
ID=15255778
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13988290A Expired - Fee Related JP2813763B2 (en) | 1990-05-31 | 1990-05-31 | Photochromic composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2813763B2 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6998214B2 (en) * | 2001-07-13 | 2006-02-14 | The Trustees Of Boston College | Methods for three-dimensional optical data storage and retrieval |
| JP2008120862A (en) * | 2006-11-09 | 2008-05-29 | Pilot Ink Co Ltd | Photochromic microcapsule |
| JP2008120861A (en) * | 2006-11-09 | 2008-05-29 | Pilot Ink Co Ltd | Photochromic material and photochromic resin composition using the same |
| WO2010037660A1 (en) * | 2008-10-02 | 2010-04-08 | Basf Se | Multi color, photoactive, color changing compositions and uv dosimeters |
| US20120288690A1 (en) * | 2009-11-16 | 2012-11-15 | Basf Se | Multi color, photoactive, color changing compositions |
| CN114685832A (en) * | 2022-03-04 | 2022-07-01 | 湖北宜美特全息科技有限公司 | Fluorescent anti-counterfeiting film with photochromic function and preparation method and application thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62184455A (en) * | 1986-01-25 | 1987-08-12 | モートン インターナショナル インコーポレイテッド | Photopolymerizing composition |
-
1990
- 1990-05-31 JP JP13988290A patent/JP2813763B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62184455A (en) * | 1986-01-25 | 1987-08-12 | モートン インターナショナル インコーポレイテッド | Photopolymerizing composition |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6998214B2 (en) * | 2001-07-13 | 2006-02-14 | The Trustees Of Boston College | Methods for three-dimensional optical data storage and retrieval |
| US7282320B2 (en) * | 2001-07-13 | 2007-10-16 | The Trustees Of Boston College | Apparatus for three-dimensional optical data storage and retrieval |
| JP2008120862A (en) * | 2006-11-09 | 2008-05-29 | Pilot Ink Co Ltd | Photochromic microcapsule |
| JP2008120861A (en) * | 2006-11-09 | 2008-05-29 | Pilot Ink Co Ltd | Photochromic material and photochromic resin composition using the same |
| WO2010037660A1 (en) * | 2008-10-02 | 2010-04-08 | Basf Se | Multi color, photoactive, color changing compositions and uv dosimeters |
| US20110293908A1 (en) * | 2008-10-02 | 2011-12-01 | Basf Se | Multi color, photoactive, color changing compositions and uv dosimeters |
| US8501053B2 (en) * | 2008-10-02 | 2013-08-06 | Basf Se | Multi color, photoactive, color changing compositions and UV dosimeters |
| US20120288690A1 (en) * | 2009-11-16 | 2012-11-15 | Basf Se | Multi color, photoactive, color changing compositions |
| CN114685832A (en) * | 2022-03-04 | 2022-07-01 | 湖北宜美特全息科技有限公司 | Fluorescent anti-counterfeiting film with photochromic function and preparation method and application thereof |
| CN114685832B (en) * | 2022-03-04 | 2023-04-18 | 湖北宜美特全息科技有限公司 | Fluorescent anti-counterfeiting film with photochromic function and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2813763B2 (en) | 1998-10-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |