JP4485213B2 - Reversible thermochromic composition and reversible thermochromic microcapsule pigment containing the same - Google Patents
Reversible thermochromic composition and reversible thermochromic microcapsule pigment containing the same Download PDFInfo
- Publication number
- JP4485213B2 JP4485213B2 JP2004012778A JP2004012778A JP4485213B2 JP 4485213 B2 JP4485213 B2 JP 4485213B2 JP 2004012778 A JP2004012778 A JP 2004012778A JP 2004012778 A JP2004012778 A JP 2004012778A JP 4485213 B2 JP4485213 B2 JP 4485213B2
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- Japan
- Prior art keywords
- color
- temperature
- reversible thermochromic
- acid
- temperature range
- 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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- 239000000203 mixture Substances 0.000 title claims description 52
- 239000003094 microcapsule Substances 0.000 title claims description 44
- 239000000049 pigment Substances 0.000 title claims description 41
- 238000011161 development Methods 0.000 claims description 42
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- 238000006243 chemical reaction Methods 0.000 claims description 3
- 230000003247 decreasing effect Effects 0.000 claims description 2
- -1 phenyl indolyl Chemical group 0.000 description 40
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- 230000000052 comparative effect Effects 0.000 description 12
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- LZFVXMOMDUCLJV-UHFFFAOYSA-N nonyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCCCCCCCC LZFVXMOMDUCLJV-UHFFFAOYSA-N 0.000 description 1
- YPVZSWAJJTUWSN-UHFFFAOYSA-N nonyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCC YPVZSWAJJTUWSN-UHFFFAOYSA-N 0.000 description 1
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- WRPMUZXHQKAAIC-CZIZESTLSA-N octadecyl (e)-octadec-9-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCC\C=C\CCCCCCCC WRPMUZXHQKAAIC-CZIZESTLSA-N 0.000 description 1
- ZFCUBQOYWAZKNO-ZPHPHTNESA-N octadecyl (z)-docos-13-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCC\C=C/CCCCCCCC ZFCUBQOYWAZKNO-ZPHPHTNESA-N 0.000 description 1
- TZXYSEYEGNHPQI-UHFFFAOYSA-N octadecyl dodecanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCC TZXYSEYEGNHPQI-UHFFFAOYSA-N 0.000 description 1
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- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- FSJWPESNOACHDX-UHFFFAOYSA-N octan-2-yl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OC(C)CCCCCC FSJWPESNOACHDX-UHFFFAOYSA-N 0.000 description 1
- RZPJLYNNGLQFSH-UHFFFAOYSA-N octan-3-yl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC(CC)CCCCC RZPJLYNNGLQFSH-UHFFFAOYSA-N 0.000 description 1
- ZVOOTAVWWKKSMX-UHFFFAOYSA-N octan-3-yl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC(CC)CCCCC ZVOOTAVWWKKSMX-UHFFFAOYSA-N 0.000 description 1
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- YYZUSRORWSJGET-UHFFFAOYSA-N octanoic acid ethyl ester Natural products CCCCCCCC(=O)OCC YYZUSRORWSJGET-UHFFFAOYSA-N 0.000 description 1
- CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 1
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- YPUOCYKJOLQYQS-KTKRTIGZSA-N oleylanilide Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)NC1=CC=CC=C1 YPUOCYKJOLQYQS-KTKRTIGZSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- GARQDIVXKVBJFP-UHFFFAOYSA-N p-Octylacetophenone Chemical compound CCCCCCCCC1=CC=C(C(C)=O)C=C1 GARQDIVXKVBJFP-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- BLUCLILBMXJZEJ-UHFFFAOYSA-N pentadecyl butyrate Chemical compound CCCCCCCCCCCCCCCOC(=O)CCC BLUCLILBMXJZEJ-UHFFFAOYSA-N 0.000 description 1
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- CNUKXAPRIPMHEX-UHFFFAOYSA-N pentadecyl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCCC CNUKXAPRIPMHEX-UHFFFAOYSA-N 0.000 description 1
- XRONBWIVNVRBIF-UHFFFAOYSA-N pentadecyl dodecanoate Chemical compound CCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCC XRONBWIVNVRBIF-UHFFFAOYSA-N 0.000 description 1
- ZJJQVISBZSCPCM-UHFFFAOYSA-N pentadecyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC ZJJQVISBZSCPCM-UHFFFAOYSA-N 0.000 description 1
- IKYYXKWKFNBGJA-UHFFFAOYSA-N pentadecyl octanoate Chemical compound CCCCCCCCCCCCCCCOC(=O)CCCCCCC IKYYXKWKFNBGJA-UHFFFAOYSA-N 0.000 description 1
- VIGFCAKEBCTBRO-UHFFFAOYSA-N pentan-3-yl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OC(CC)CC VIGFCAKEBCTBRO-UHFFFAOYSA-N 0.000 description 1
- KGWZZYZGKLHJTL-UHFFFAOYSA-N pentan-3-yl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(CC)CC KGWZZYZGKLHJTL-UHFFFAOYSA-N 0.000 description 1
- JIMNZICTZXMMIE-UHFFFAOYSA-N pentan-3-yl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(CC)CC JIMNZICTZXMMIE-UHFFFAOYSA-N 0.000 description 1
- PQWBDPUBNMEITD-UHFFFAOYSA-N pentyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCCCC PQWBDPUBNMEITD-UHFFFAOYSA-N 0.000 description 1
- YGDMPMKCHSXJJF-UHFFFAOYSA-N pentyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCCCCC YGDMPMKCHSXJJF-UHFFFAOYSA-N 0.000 description 1
- QPXYWTUZRZEUAK-UHFFFAOYSA-N pentyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCCCCC QPXYWTUZRZEUAK-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- BOTNYLSAWDQNEX-UHFFFAOYSA-N phenoxymethylbenzene Chemical compound C=1C=CC=CC=1COC1=CC=CC=C1 BOTNYLSAWDQNEX-UHFFFAOYSA-N 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- IZQHTCYPZWOMFQ-UHFFFAOYSA-N propan-2-yl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OC(C)C IZQHTCYPZWOMFQ-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229940094908 stearyl myristate Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- PVJXQWMBHUOOCK-UHFFFAOYSA-N tetradecyl decanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCC PVJXQWMBHUOOCK-UHFFFAOYSA-N 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- ZDIXOWNDGFVYNK-UHFFFAOYSA-N tridecan-3-one Chemical compound CCCCCCCCCCC(=O)CC ZDIXOWNDGFVYNK-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- AAEAAZAPXYHUIW-UHFFFAOYSA-N tridecyl butyrate Chemical compound CCCCCCCCCCCCCOC(=O)CCC AAEAAZAPXYHUIW-UHFFFAOYSA-N 0.000 description 1
- JFOWPZXGNKSOTH-UHFFFAOYSA-N tridecyl decanoate Chemical compound CCCCCCCCCCCCCOC(=O)CCCCCCCCC JFOWPZXGNKSOTH-UHFFFAOYSA-N 0.000 description 1
- VBCBSDJKFLGBIX-UHFFFAOYSA-N tridecyl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCC VBCBSDJKFLGBIX-UHFFFAOYSA-N 0.000 description 1
- INJZMNQWJIWOEA-UHFFFAOYSA-N tridecyl dodecanoate Chemical compound CCCCCCCCCCCCCOC(=O)CCCCCCCCCCC INJZMNQWJIWOEA-UHFFFAOYSA-N 0.000 description 1
- QEIJVPZRDAHCHE-UHFFFAOYSA-N tridecyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCC QEIJVPZRDAHCHE-UHFFFAOYSA-N 0.000 description 1
- GKAVWWCJCPVMNR-UHFFFAOYSA-N tridecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCC GKAVWWCJCPVMNR-UHFFFAOYSA-N 0.000 description 1
- CTWLAMKOJQOQLN-UHFFFAOYSA-N tridecyl tetradecanoate Chemical compound CCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC CTWLAMKOJQOQLN-UHFFFAOYSA-N 0.000 description 1
- 229940113164 trimyristin Drugs 0.000 description 1
- WENNKWXPAWNIOO-UHFFFAOYSA-N undecan-5-one Chemical compound CCCCCCC(=O)CCCC WENNKWXPAWNIOO-UHFFFAOYSA-N 0.000 description 1
- 229940057402 undecyl alcohol Drugs 0.000 description 1
- ZBUPFBRWKJDEAX-UHFFFAOYSA-N undecyl decanoate Chemical compound CCCCCCCCCCCOC(=O)CCCCCCCCC ZBUPFBRWKJDEAX-UHFFFAOYSA-N 0.000 description 1
- JHDNXONYKMEEBK-UHFFFAOYSA-N undecyl dodecanoate Chemical compound CCCCCCCCCCCOC(=O)CCCCCCCCCCC JHDNXONYKMEEBK-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NCSMRDAYUUPTTK-UHFFFAOYSA-N undecyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCC NCSMRDAYUUPTTK-UHFFFAOYSA-N 0.000 description 1
- FOROCIRSIXDJQG-UHFFFAOYSA-N undecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCC FOROCIRSIXDJQG-UHFFFAOYSA-N 0.000 description 1
- MRXRZUAPYOLFFW-UHFFFAOYSA-N undecyl octanoate Chemical compound CCCCCCCCCCCOC(=O)CCCCCCC MRXRZUAPYOLFFW-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Images
Description
本発明は、温度変化により可逆的に変色する可逆熱変色性組成物及びそれを内包した可逆熱変色性マイクロカプセル顔料に関する。 The present invention relates to a reversible thermochromic composition that reversibly discolors with a change in temperature and a reversible thermochromic microcapsule pigment encapsulating the composition.
従来より、発色状態からの降温過程で消色を開始し、特定温度以下で完全消色状態を呈し、引き続く昇温過程で発色を開始し、発色状態に復帰する可逆熱変色性を示す組成物に関して、幾つかの提案が開示されている。
前記組成物は大別すると二つのタイプに分けることができ、第1のタイプは変色温度を境として、その前後で変色し、変色前後の両状態のうち常温域では特定の一方の状態しか存在しえない。即ち、もう一方の状態はその状態が発現するのに要する熱または冷熱が適用されている間は維持されるが、前記熱または冷熱の適用がなくなれば常温域で呈する元の状態に戻る、温度−色濃度曲線に関して比較的小さいヒステリシス幅(ΔH)を示して変色する可逆熱変色性組成物である(例えば、特許文献1、2参照)。
第2のタイプは、温度を変色温度域より低温側から上昇させていく場合と、逆に変色温度域より高温側から下降させていく場合とで大きく異なる経路を辿って変色する、温度−色濃度曲線に関して大きいヒステリシス幅(ΔH)を示して変色し、変色に要した熱又は冷熱の適用を取り去った後にあっても、低温側トリガーと高温側トリガーとの間の温度域で前記低温側トリガー以下又は高温側トリガー以上で変色させた色彩を互変的に記憶保持可能な感温変色性色彩記憶性組成物である(例えば、特許文献3参照)。
前記した組成物はヒステリシス幅(ΔH)の大小が異なるものの、図1の温度−色濃度曲線に示す如き変色挙動を呈する。前記変色挙動は、(イ)電子供与性呈色性有機化合物と(ロ)電子受容性化合物との呈色反応の生起温度を決める(ハ)反応媒体に依存し、特定される。
The composition can be roughly divided into two types. The first type changes color before and after the color change temperature, and there is only one specific state in the normal temperature range of both states before and after the color change. I can't. That is, the other state is maintained while the heat or cold necessary for the state to develop is applied, but when the heat or cold is not applied, the temperature returns to the original state exhibited in the normal temperature range. A reversible thermochromic composition that changes color with a relatively small hysteresis width (ΔH) with respect to the color density curve (see, for example, Patent Documents 1 and 2).
The second type is a temperature-color that changes color by following a very different path between when the temperature is raised from the lower temperature side than the color change temperature range and when the temperature is lowered from the higher temperature side than the color change temperature range. The low temperature side trigger is changed in the temperature range between the low temperature side trigger and the high temperature side trigger even after removing the heat or cold heat required for the color change with a large hysteresis width (ΔH) with respect to the density curve. This is a temperature-sensitive color-changing color memory composition capable of reversibly storing and holding the color changed by the following or higher temperature trigger (for example, see Patent Document 3).
The above-described composition exhibits a discoloration behavior as shown in the temperature-color density curve of FIG. 1 although the hysteresis width (ΔH) is different. The discoloration behavior is specified depending on (c) the reaction medium that determines the occurrence temperature of the color reaction between (a) the electron-donating color-forming organic compound and (b) the electron-accepting compound.
本発明者は、前記した可逆熱変色性組成物の発色状態における変色挙動について更に検討した結果、特定の(ロ)電子受容性化合物を用いることにより、前記温度−色濃度曲線を変位させることを見出し、本発明を完成させた。
本発明は、従来の(イ)、(ロ)、(ハ)三成分系の変色特性に改良を加えた可逆熱変色性組成物及びそれを内包した可逆熱変色性マイクロカプセル顔料を提供するものであり、特に示温分野に好適な変色特性を有するものである。
As a result of further study on the discoloration behavior of the reversible thermochromic composition in the coloring state, the present inventor has found that the temperature-color density curve can be displaced by using a specific (b) electron accepting compound. The headline and the present invention were completed.
The present invention provides a reversible thermochromic composition in which the conventional (I), (B), and (C) three-component system discoloration properties are improved, and a reversible thermochromic microcapsule pigment containing the same. In particular, it has a discoloration characteristic suitable for the temperature indicating field.
本発明は、(イ)電子供与性呈色性有機化合物、(ロ)電子受容性化合物、(ハ)前記(イ)と(ロ)の呈色反応の生起温度を決める反応媒体を含み、色濃度−温度曲線の関係において、発色状態から温度が上昇する過程で消色開始温度(T3 )に達すると消色し始め、完全消色温度(T4 )以上では完全に消色し、消色状態から温度が下降する過程で発色開始温度(T2 )に達すると発色し始め、完全発色温度(T1 )以下では完全に発色する変色挙動を示す可逆熱変色性組成物において、(ロ)電子受容性化合物として4,4−オキシビスフェノールを含んでなり、発色開始温度(T2 )以下の温度域に、発色状態から自然に消色する自然消色温度域(X)と発色状態を保持する発色保持温度域(Y)を有することを特徴とする可逆熱変色性組成物を要件とする。
更には、前記自然消色温度域(X)が下記式(1)を満たし、且つ、発色保持温度域(Y)が下記式(2)を満たすこと、
T2 −20≦X≦T2 (1)
Y<T2 −20 (2)
消色促進剤として、石油系炭化水素樹脂を含んでなることを要件とする。
更には、前記可逆熱変色性組成物をマイクロカプセルに内包してなる可逆熱変色性マイクロカプセル顔料を要件とする。
The present invention includes (a) an electron-donating color-forming organic compound, (b) an electron-accepting compound, (c) a reaction medium that determines the temperature at which the color reaction of (a) and (b) occurs. concentration - in the context of temperature curve, and in the course of temperature rise from the colored state reaches a decoloring starting temperature (T 3) begins to decoloring, completely decolorized a complete decoloring temperature (T 4) above, consumption In a reversible thermochromic composition that exhibits a color-changing behavior that begins to develop when the color development start temperature (T 2 ) is reached in the process of decreasing the temperature from the color state and completely develops below the complete color development temperature (T 1 ). ) Containing 4,4-oxybisphenol as an electron-accepting compound, and having a natural color erasing temperature range (X) and a color developing state in which the color disappears naturally from a color developing state in a temperature range below the color developing start temperature (T 2 ). Reversible thermal change characterized by having color retention temperature range (Y) Sex composition and requirements.
Furthermore, the natural decoloring temperature range (X) satisfies the following formula (1), and the color retention temperature range (Y) satisfies the following formula (2).
T 2 −20 ≦ X ≦ T 2 (1)
Y <T 2 -20 (2)
It is a requirement that it comprises a petroleum hydrocarbon resin as a decoloring accelerator.
Furthermore, a reversible thermochromic microcapsule pigment obtained by encapsulating the reversible thermochromic composition in microcapsules is a requirement.
本発明は、発色開始温度(T2 )以下の温度域に、発色状態から自然に消色する自然消色温度域と発色状態を保持する発色保持温度域を有する可逆熱変色性組成物及びそれを内包した可逆熱変色性マイクロカプセル顔料を提供でき、特に示温分野に好適である。 The present invention relates to a reversible thermochromic composition having a natural color erasing temperature range in which a color is naturally erased from a color development state and a color development holding temperature range in which the color development state is maintained in a temperature range below a color development start temperature (T 2 ). Can be provided, and is particularly suitable for the temperature indicating field.
以下に可逆熱変色性組成物の色濃度−温度曲線におけるヒステリシス特性について詳しく説明する。
図1において、縦軸に色濃度、横軸に温度が表されている。温度変化による色濃度の変化は矢印に沿って進行する。ここで、Aは完全消色状態に達する最低温度T4 (以下、完全消色温度と称す)における濃度を示す点であり、Bは完全発色状態を保持できる最高温度T3 (以下、消色開始温度と称す)における濃度を示す点であり、Cは完全消色状態を保持できる最低温度T2 (以下、発色開始温度と称す)における濃度を示す点であり、Dは完全呈色状態に達する最高温度T1 (以下、完全発色温度と称す)における濃度を示す点である。
The hysteresis characteristics in the color density-temperature curve of the reversible thermochromic composition will be described in detail below.
In FIG. 1, the vertical axis represents color density and the horizontal axis represents temperature. The change in color density due to the temperature change proceeds along the arrow. Here, A is a point indicating the density at the minimum temperature T 4 (hereinafter referred to as a complete color erasing temperature) that reaches the complete color erasing state, and B is the maximum temperature T 3 (hereinafter referred to as the color erasing) that can maintain the complete color development state. C is a point indicating the density at the lowest temperature T 2 (hereinafter referred to as the color development start temperature) at which a completely decolored state can be maintained, and D is a fully colored state. This is a point indicating the density at the maximum temperature T 1 reached (hereinafter referred to as the complete color development temperature).
本発明は、(ロ)電子受容性化合物として4,4−オキシビスフェノールを配合することにより、発色開始温度(T2 )以下の温度域に、発色状態から自然に消色する自然消色温度域と発色状態を保持する発色保持温度域を有するものである。
この点について説明すれば、図2の色濃度−温度曲線の破線で示したように発色開始温度(T2 )以下の特定温度域で発色状態から自然に消色する自然消色温度域(X)が存在する。
消色状態から温度が下降して完全発色温度(T1 )に達すると、可逆熱変色性組成物は完全に発色するが、T2 以下の温度、且つ、自然消色温度域(X)で温度を一定に保つと、矢印に示されるように徐々に発色状態から消色して点線のように発色濃度が低下する変色挙動を示す。
また、温度が下降して完全発色温度(T1 )に達した後、昇温しても発色開始温度(T2 )以下の温度であれば、温度を一定に保つと、矢印に示されるように徐々に発色状態から消色して点線のように発色濃度が低下する変色挙動を示す。
消色の度合いはT2 に近い温度になる程大きくなり、発色濃度が低下する傾向にある。なお、いったん消色して発色濃度が低下すると、その後冷却しても発色濃度が回復することはなく、発色濃度が低下した状態は維持される。
元の発色濃度に復帰させるためには、完全消色温度(T4 )まで昇温させた後、降温させることにより、完全発色温度(T1 )に達して濃度が回復する。
本発明の可逆熱変色性組成物は、前記した自然消色温度域(X)と共に、発色状態を保持する発色保持温度域(Y)も有する。
発色保持温度域(Y)は発色開始温度(T2 )以下の温度域で存在する。
前記発色保持温度域(Y)では、自然消色温度域(X)のように徐々に発色状態から消色することなく、発色濃度は維持される。
In the present invention, (b) a natural color erasing temperature range in which a color is naturally erased from a color development state in a temperature range below the color development start temperature (T 2 ) by blending 4,4-oxybisphenol as an electron accepting compound. And a color development holding temperature range for maintaining the color development state.
Explaining this point, as indicated by the broken line of the color density-temperature curve in FIG. 2, the natural color erasing temperature range (X that naturally erases from the color development state in a specific temperature range below the color development start temperature (T 2 ). ) Exists.
When the temperature drops from the decolored state and reaches the complete color development temperature (T 1 ), the reversible thermochromic composition is completely colored, but at a temperature below T 2 and in the natural color erasure temperature range (X). When the temperature is kept constant, the color change behavior gradually decreases from the color development state as indicated by the arrow and the color density decreases as shown by the dotted line.
Further, when the temperature drops and reaches the complete color development temperature (T 1 ), if the temperature is not higher than the color development start temperature (T 2 ) even if the temperature is increased, the temperature is kept constant as indicated by the arrow. Fig. 3 shows the discoloration behavior in which the color density gradually decreases from the colored state and the color density decreases as shown by the dotted line.
The degree of decoloration increases as the temperature approaches T 2 , and the color density tends to decrease. In addition, once the color is erased and the color density is lowered, the color density is not recovered even after cooling, and the state where the color density is lowered is maintained.
In order to return to the original color density, the temperature is raised to the complete color erasing temperature (T 4 ) and then lowered to reach the full color temperature (T 1 ) and the density is recovered.
The reversible thermochromic composition of the present invention also has a color retention temperature range (Y) for maintaining a color development state in addition to the natural decoloration temperature range (X) described above.
The color development holding temperature range (Y) exists in a temperature range below the color development start temperature (T 2 ).
In the color retention temperature range (Y), the color density is maintained without gradually erasing from the color development state as in the natural color erasure temperature range (X).
なお、自然消色温度域(X)は、T2 −15≦X≦T3 の温度域であり、発色保持温度域(Y)は、Y<T2 −15の温度域であることが好ましい。
前述のように、本発明の可逆熱変色性組成物が発色開始温度(T2 )以下の温度域に、発色状態から自然に消色する自然消色温度域と発色状態を保持する発色保持温度域を有するのは、適用される(ロ)成分自体の結晶性が高く、特に脂肪族性雰囲気下で結晶性が強いこと、及び、(ロ)成分自体が強い極性を備えており、(ハ)成分中で一旦溶解した(ロ)成分が徐々に系外にて結晶化し始め、自然に消色する傾向を示すことによるものと推察される。
The natural decoloring temperature range (X) is preferably a temperature range of T 2 -15 ≦ X ≦ T 3 , and the color development holding temperature range (Y) is preferably a temperature range of Y <T 2 -15. .
As described above, the reversible thermochromic composition of the present invention has a natural color erasing temperature range in which a color is erased naturally from a color development state and a color development holding temperature at which the color development state is maintained in a temperature range below the color development start temperature (T 2 ). The (B) component itself has high crystallinity, particularly high crystallinity in an aliphatic atmosphere, and (B) the component itself has a strong polarity. It is inferred that the component (b) once dissolved in the component (b) starts to crystallize gradually outside the system and tends to discolor naturally.
可逆熱変色性組成物において、(ロ)電子受容性化合物としては4,4−オキシビスフェノールが用いられる。 In the reversible thermochromic composition, 4,4-oxybisphenol is used as the (b) electron accepting compound.
前記(イ)電子供与性呈色性有機化合物としては、従来より公知のジフェニルメタンフタリド類、フェニルインドリルフタリド類、インドリルフタリド類、ジフェニルメタンアザフタリド類、フェニルインドリルアザフタリド類、フルオラン類、スチリノキノリン類、ジアザローダミンラクトン類等が挙げられ、以下にこれらの化合物を例示する。
3,3−ビス(p−ジメチルアミノフェニル)−6−ジメチルアミノフタリド、
3−(4−ジエチルアミノフェニル)−3−(1−エチル−2−メチルインドール−3−イル)フタリド、
3,3−ビス(1−n−ブチル−2−メチルインドール−3−イル)フタリド、
3,3−ビス(2−エトキシ−4−ジエチルアミノフェニル)−4−アザフタリド、
3−〔2−エトキシ−4−(N−エチルアニリノ)フェニル〕−3−(1−エチル−2−メチルインドール−3−イル)−4−アザフタリド、
3,6−ジメトキシフルオラン、3,6−ジ−n−ブトキシフルオラン、
2−メチル−6−(N−エチル−N−p−トリルアミノ)フルオラン、
3−クロロ−6−シクロヘキシルアミノフルオラン、
2−メチル−6−シクロヘキシルアミノフルオラン、
2−(2−クロロアニリノ)−6−ジ−n−ブチルアミノフルオラン、
2−(3−トリフルオロメチルアニリノ)−6−ジエチルアミノフルオラン、
2−(N−メチルアニリノ)−6−(N−エチル−N−p−トリルアミノ)フルオラン、
1,3−ジメチル−6−ジエチルアミノフルオラン、
2−クロロ−3−メチル−6−ジエチルアミノフルオラン、
2−アニリノ−3−メチル−6−ジエチルアミノフルオラン、
2−アニリノ−3−メチル−6−ジ−n−ブチルアミノフルオラン、
2−キシリジノ−3−メチル−6−ジエチルアミノフルオラン、
1,2−ベンツ−6−ジエチルアミノフルオラン、
1,2−ベンツ−6−(N−エチル−N−イソブチルアミノ)フルオラン、
1,2−ベンツ−6−(N−エチル−N−イソアミルアミノ)フルオラン、
2−(3−メトキシ−4−ドデコキシスチリル)キノリン、
スピロ〔5H−(1)ベンゾピラノ(2,3−d)ピリミジン−5,1′(3′H)イソベンゾフラン〕−3′−オン,2−(ジエチルアミノ)−8−(ジエチルアミノ)−4−メチル−、
スピロ〔5H−(1)ベンゾピラノ(2,3−d)ピリミジン−5,1′(3′H)イソベンゾフラン〕−3′−オン,2−(ジ−n−ブチルアミノ)−8−(ジ−n−ブチルアミノ)−4−メチル−、
スピロ〔5H−(1)ベンゾピラノ(2,3−d)ピリミジン−5,1′(3′H)イソベンゾフラン〕−3′−オン,2−(ジ−n−ブチルアミノ)−8−(ジエチルアミノ)−4−メチル−、
スピロ〔5H−(1)ベンゾピラノ(2,3−d)ピリミジン−5,1′(3′H)イソベンゾフラン〕−3′−オン,2−(ジ−n−ブチルアミノ)−8−(N−エチル−N−i−アミルアミノ)−4−メチル−、
スピロ〔5H−(1)ベンゾピラノ(2,3−d)ピリミジン−5,1′(3′H)イソベンゾフラン〕−3′−オン,2−(ジ−n−ブチルアミノ)−8−(ジ−n−ブチルアミノ)−4−フェニル。
更には、蛍光性の黄色〜赤色の発色を発現させるのに有効な、ピリジン系、キナゾリン系、ビスキナゾリン系化合物等を挙げることができる。
Examples of the (i) electron donating color-forming organic compound include conventionally known diphenylmethane phthalides, phenyl indolyl phthalides, indolyl phthalides, diphenyl methane azaphthalides, phenyl indolyl azaphthalides , Fluorans, stylinoquinolines, diazarhodamine lactones, etc., and these compounds are exemplified below.
3,3-bis (p-dimethylaminophenyl) -6-dimethylaminophthalide,
3- (4-diethylaminophenyl) -3- (1-ethyl-2-methylindol-3-yl) phthalide,
3,3-bis (1-n-butyl-2-methylindol-3-yl) phthalide,
3,3-bis (2-ethoxy-4-diethylaminophenyl) -4-azaphthalide,
3- [2-ethoxy-4- (N-ethylanilino) phenyl] -3- (1-ethyl-2-methylindol-3-yl) -4-azaphthalide,
3,6-dimethoxyfluorane, 3,6-di-n-butoxyfluorane,
2-methyl-6- (N-ethyl-Np-tolylamino) fluorane,
3-chloro-6-cyclohexylaminofluorane,
2-methyl-6-cyclohexylaminofluorane,
2- (2-chloroanilino) -6-di-n-butylaminofluorane,
2- (3-trifluoromethylanilino) -6-diethylaminofluorane,
2- (N-methylanilino) -6- (N-ethyl-Np-tolylamino) fluorane,
1,3-dimethyl-6-diethylaminofluorane,
2-chloro-3-methyl-6-diethylaminofluorane,
2-anilino-3-methyl-6-diethylaminofluorane,
2-anilino-3-methyl-6-di-n-butylaminofluorane,
2-xylidino-3-methyl-6-diethylaminofluorane,
1,2-benz-6-diethylaminofluorane,
1,2-benz-6- (N-ethyl-N-isobutylamino) fluorane,
1,2-benz-6- (N-ethyl-N-isoamylamino) fluorane,
2- (3-methoxy-4-dodecoxystyryl) quinoline,
Spiro [5H- (1) benzopyrano (2,3-d) pyrimidine-5,1 '(3'H) isobenzofuran] -3'-one, 2- (diethylamino) -8- (diethylamino) -4-methyl −,
Spiro [5H- (1) benzopyrano (2,3-d) pyrimidine-5,1 '(3'H) isobenzofuran] -3'-one, 2- (di-n-butylamino) -8- (di -N-butylamino) -4-methyl-,
Spiro [5H- (1) benzopyrano (2,3-d) pyrimidine-5,1 '(3'H) isobenzofuran] -3'-one, 2- (di-n-butylamino) -8- (diethylamino) ) -4-methyl-,
Spiro [5H- (1) benzopyrano (2,3-d) pyrimidine-5,1 '(3'H) isobenzofuran] -3'-one, 2- (di-n-butylamino) -8- (N -Ethyl-Ni-amylamino) -4-methyl-,
Spiro [5H- (1) benzopyrano (2,3-d) pyrimidine-5,1 '(3'H) isobenzofuran] -3'-one, 2- (di-n-butylamino) -8- (di -N-Butylamino) -4-phenyl.
Furthermore, there can be mentioned pyridine-based, quinazoline-based, bisquinazoline-based compounds and the like that are effective in developing fluorescent yellow to red color development.
(ハ)前記(イ)、(ロ)による電子授受反応を特定温度域において可逆的に生起させる反応媒体である化合物としては、炭化水素類、ハロゲン化炭化水素類、スルフィド類、エーテル類、ケトン類、エステル類、酸アミド類、アルコール類、ワックス類等の従来より汎用の反応媒体が総て有効であり、中分子量ポリマー類の如く、半液状物質であっても良く、これらの化合物の一種又は二種以上を適用できる。前記各化合物を用いてマイクロカプセル化及び二次加工に応用する場合は低分子量のものは高熱処理を施すとカプセル系外に蒸散するので、安定的にカプセル内に保持させるために、炭素数10以上の化合物が有効である。 (C) Compounds that are reaction media for reversibly causing the electron transfer reaction in (a) and (b) above in a specific temperature range include hydrocarbons, halogenated hydrocarbons, sulfides, ethers, and ketones. Conventionally, general-purpose reaction media such as alcohols, esters, acid amides, alcohols, waxes and the like are all effective, and they may be semi-liquid substances such as medium molecular weight polymers, and are one kind of these compounds. Or 2 or more types can be applied. When the above compounds are used for microencapsulation and secondary processing, those having a low molecular weight evaporate out of the capsule system when subjected to a high heat treatment. The above compounds are effective.
スルフィド類としては、ジ−n−オクチルスルフィド、ジ−n−ノニルスルフィド、ジ−n−デシルスルフィド、ジ−n−ドデシルスルフィド、ジ−n−テトラデシルスルフィド、ジ−n−ヘキサデシルスルフィド、ジ−n−オクタデシルスルフィド、オクチルドデシルスルフィド、ジフェニルスルフィド、ジベンジルスルフィド、ジトリルスルフィド、ジエチルフェニルスルフィド、ジナフチルスルフィド、4,4′−ジクロロ−ジフェニルスルフィド、2,4,5,4′−テトラクロロ−ジフェニルスルフィド等を例示できる。 The sulfides include di-n-octyl sulfide, di-n-nonyl sulfide, di-n-decyl sulfide, di-n-dodecyl sulfide, di-n-tetradecyl sulfide, di-n-hexadecyl sulfide, di- -N-octadecyl sulfide, octyldodecyl sulfide, diphenyl sulfide, dibenzyl sulfide, ditolyl sulfide, diethylphenyl sulfide, dinaphthyl sulfide, 4,4'-dichloro-diphenyl sulfide, 2,4,5,4'-tetrachloro -A diphenyl sulfide etc. can be illustrated.
エーテル類としては、総炭素数10以上の脂肪族エーテル類として、ジペンチルエーテル、ジヘキシルエーテル、ジヘプチルエーテル、ジオクチルエーテル、ジノニルエーテル、ジデシルエーテル、ジウンデシルエーテル、ジドデシルエーテル、ジトリデシルエーテル、ジテトラデシルエーテル、ジペンタデシルエーテル、ジヘキサデシルエーテル、ジオクタデシルエーテル、デカンジオールジメチルエーテル、ウンデカンジオールジメチルエーテル、ドデカンジオールジメチルエーテル、トリデカンジオールジメチルエーテル、デカンジオールジエチルエーテル、ウンデカンジオールジエチルエーテル等、脂環式エーテル類として、s−トリオキサン等。芳香族エーテル類として、フェニルエーテル、ベンジルフェニルエーテル、ジベンジルエーテル、ジ−p−トリルエーテル、1−メトキシナフタレン、3,4,5−トリメトキシトルエン等を例示できる。 Examples of ethers include aliphatic ethers having a total carbon number of 10 or more, dipentyl ether, dihexyl ether, diheptyl ether, dioctyl ether, dinonyl ether, didecyl ether, diundecyl ether, didodecyl ether, ditridecyl ether, Ditetradecyl ether, dipentadecyl ether, dihexadecyl ether, dioctadecyl ether, decane diol dimethyl ether, undecane diol dimethyl ether, dodecane diol dimethyl ether, tridecane diol dimethyl ether, decane diol diethyl ether, undecane diol diethyl ether, etc. Examples of ethers include s-trioxane. Examples of aromatic ethers include phenyl ether, benzyl phenyl ether, dibenzyl ether, di-p-tolyl ether, 1-methoxynaphthalene, 3,4,5-trimethoxytoluene and the like.
ケトン類としては、総炭素数が10以上の脂肪族ケトン類として、2−デカノン、3−デカノン、4−デカノン、2−ウンデカノン、3−ウンデカノン、4−ウンデカノン、5−ウンデカノン、6−ウンデカノン、2−ドデカノン、3−ドデカノン、4−ドデカノン、5−ドデカノン、2−トリデカノン、3−トリデカノン、2−テトラデカノン、2−ペンタデカノン、8−ペンタデカノン、2−ヘキサデカノン、3−ヘキサデカノン、9−ヘプタデカノン、2−ペンタデカノン、2−オクタデカノン、2−ノナデカノン、10−ノナダカノン、2−エイコサノン、11−エイコサノン、2−ヘンエイコサノン、2-ドコサノン、ラウロン、ステアロン等、総炭素数が12乃至24のアリールアルキルケトン類として、n−オクタデカノフェノン、n−ヘプタデカノフェノン、n−ヘキサデカノフェノン、n−ペンタデカノフェノン、n−テトラデカノフェノン、4−n−ドデカアセトフェノン、n−トリデカノフェノン、4−n−ウンデカノアセトフェノン、n−ラウロフェノン、4−n−デカノアセトフェノン、n−ウンデカノフェノン、4−n−ノニルアセトフェノン、n−デカノフェノン、4−n−オクチルアセトフェノン、n−ノナノフェノン、4−n−ヘプチルアセトフェノン、n−オクタノフェノン、4−n−ヘキシルアセトフェノン、4−n−シクロヘキシルアセトフェノン、4−tert−ブチルプロピオフェノン、n−ヘプタフェノン、4−n−ペンチルアセトフェノン、シクロヘキシルフェニルケトン、ベンジル−n−ブチルケトン、4−n−ブチルアセトフェノン、n−ヘキサノフェノン、4−イソブチルアセトフェノン、1−アセトナフトン、2−アセトナフトン、シクロペンチルフェニルケトン等、アリールアリールケトン類として、ベンゾフェノン、ベンジルフェニルケトン、ジベンジルケトン等、脂環式ケトンとして、シクロオクタノン、シクロドデカノン、シクロペンタデカノン、4−tert−ブチルシクロヘキサノン等を例示できる。 As the ketones, as aliphatic ketones having a total carbon number of 10 or more, 2-decanone, 3-decanone, 4-decanone, 2-undecanone, 3-undecanone, 4-undecanone, 5-undecanone, 6-undecanone, 2-dodecanone, 3-dodecanone, 4-dodecanone, 5-dodecanone, 2-tridecanone, 3-tridecanone, 2-tetradecanone, 2-pentadecanone, 8-pentadecanone, 2-hexadecanone, 3-hexadecanone, 9-heptadecanone, 2- N as arylalkyl ketones having a total carbon number of 12 to 24, such as pentadecanone, 2-octadecanone, 2-nonadecanone, 10-nonadacanone, 2-eicosanone, 11-eicosanone, 2-heneicosanone, 2-docosanone, laurone and stearone -Octadecanopheno N-heptadecanophenone, n-hexadecanophenone, n-pentadecanophenone, n-tetradecanophenone, 4-n-dodecanacetophenone, n-tridecanophenone, 4-n-undecanoacetophenone, n-laurophenone, 4-n-decanoacetophenone, n-undecanophenone, 4-n-nonylacetophenone, n-decanophenone, 4-n-octylacetophenone, n-nonanophenone, 4-n-heptylacetophenone, n- Octanophenone, 4-n-hexylacetophenone, 4-n-cyclohexylacetophenone, 4-tert-butylpropiophenone, n-heptaphenone, 4-n-pentylacetophenone, cyclohexylphenylketone, benzyl-n-butylketone, 4- n-Butyl acetofe Non-, n-hexanophenone, 4-isobutylacetophenone, 1-acetonaphthone, 2-acetonaphthone, cyclopentylphenylketone, arylaryl ketones, benzophenone, benzylphenylketone, dibenzylketone, etc. Examples include octanone, cyclododecanone, cyclopentadecanone, and 4-tert-butylcyclohexanone.
エステル類としては、炭素数10以上のエステル類が有効であり、脂肪族及び脂環或いは芳香環を有する一価カルボン酸と、脂肪族及び脂環或いは芳香環を有する一価アルコールの任意の組み合わせから得られるエステル類、脂肪族及び脂環或いは芳香環を有する多価カルボン酸と、脂肪族及び脂環或いは芳香環を有する一価アルコールの任意の組み合わせから得られるエステル類、脂肪族及び脂環或いは芳香環を有する一価カルボン酸と、脂肪族及び脂環或いは芳香環を有する多価アルコールの任意の組み合わせから得られるエステル類が挙げられ、具体的にはカプリル酸エチル、カプリル酸オクチル、カプリル酸ステアリル、カプリン酸ミリスチル、カプリン酸ステアリル、カプリン酸ドコシル、ラウリン酸2−エチルヘキシル、ラウリン酸n−デシル、ミリスチン酸3−メチルブチル、ミリスチン酸セチル、パルミチン酸イソプロピル、パルミチン酸ネオペンチル、パルミチン酸ノニル、パルミチン酸シクロヘキシル、ステアリン酸n−ブチル、ステアリン酸2−メチルブチル、ステアリン酸3,5,5−トリメチルヘキシル、ステアリン酸n−ウンデシル、ステアリン酸ペンタデシル、ステアリン酸ステアリル、ステアリン酸シクロヘキシルメチル、ベヘン酸イソプロピル、ベヘン酸ヘキシル、ベヘン酸ラウリル、ベヘン酸ベヘニル、安息香酸セチル、p−tert−ブチル安息香酸ステアリル、フタル酸ジミリスチル、フタル酸ジステアリル、シュウ酸ジミリスチル、シュウ酸ジセチル、マロン酸ジセチル、コハク酸ジラウリル、グルタル酸ジラウリル、アジピン酸ジウンデシル、アゼライン酸ジラウリル、セバシン酸ジ−(n−ノニル)、1,18−オクタデシルメチレンジカルボン酸ジネオペンチル、エチレングリコールジミリステート、プロピレングリコールジラウレート、プロピレングリコールジステアレート、ヘキシレングリコールジパルミテート、1,5−ペンタンジオールジミリステート、1,2,6−ヘキサントリオールトリミリステート、1,4−シクロヘキサンジオールジデシル、1,4−シクロヘキサンジメタノールジミリステート、キシレングリコールジカプリネート、キシレングリコールジステアレート等を例示できる。 As the esters, esters having 10 or more carbon atoms are effective, and any combination of a monovalent carboxylic acid having an aliphatic and alicyclic or aromatic ring and a monohydric alcohol having an aliphatic and alicyclic or aromatic ring. Esters, aliphatic and alicyclic rings obtained from any combination of esters, aliphatic and alicyclic or aromatic polyvalent carboxylic acids obtained from the above and monohydric alcohols having aliphatic and alicyclic or aromatic rings Or esters obtained from any combination of monovalent carboxylic acid having an aromatic ring and aliphatic and alicyclic or polyhydric alcohol having an aromatic ring, specifically, ethyl caprylate, octyl caprylate, capryl Stearyl acid, myristyl caprate, stearyl caprate, docosyl caprate, 2-ethylhexyl laurate, lauric N-decyl acid, 3-methylbutyl myristate, cetyl myristate, isopropyl palmitate, neopentyl palmitate, nonyl palmitate, cyclohexyl palmitate, n-butyl stearate, 2-methylbutyl stearate, 3,5,5 stearates -Trimethylhexyl, n-undecyl stearate, pentadecyl stearate, stearyl stearate, cyclohexylmethyl stearate, isopropyl behenate, hexyl behenate, lauryl behenate, behenyl behenate, cetyl benzoate, p-tert-butylbenzoic acid Stearyl, dimyristyl phthalate, distearyl phthalate, dimyristyl oxalate, dicetyl oxalate, dicetyl malonate, dilauryl succinate, dilauryl glutarate, diuric adipate Decyl, dilauryl azelate, di- (n-nonyl) sebacate, dineopentyl 1,18-octadecylmethylenedicarboxylate, ethylene glycol dimyristate, propylene glycol dilaurate, propylene glycol distearate, hexylene glycol dipalmitate, 1 , 5-pentanediol dimyristate, 1,2,6-hexanetriol trimyristate, 1,4-cyclohexanediol didecyl, 1,4-cyclohexanedimethanol dimyristate, xylene glycol dicaprinate, xylene glycol di Examples include stearate.
又、飽和脂肪酸と分枝脂肪族アルコールのエステル、不飽和脂肪酸又は分枝もしくは置換基を有する飽和脂肪酸と分岐状であるか又は炭素数16以上の脂肪族アルコールのエステル、酪酸セチル、酪酸ステアリル及び酪酸ベヘニルから選ばれるエステル化合物も有効である。
具体的には、酪酸2−エチルヘキシル、ベヘン酸2−エチルヘキシル、ミリスチン酸2−エチルヘキシル、カプリン酸2−エチルヘキシル、ラウリン酸3,5,5−トリメチルヘキシル、パルミチン酸3,5,5−トリメチルヘキシル、ステアリン酸3,5,5−トリメチルヘキシル、カプロン酸2−メチルブチル、カプリル酸2−メチルブチル、カプリン酸2−メチルブチル、パルミチン酸1−エチルプロピル、ステアリン酸1−エチルプロピル、ベヘン酸1−エチルプロピル、ラウリン酸1−エチルヘキシル、ミリスチン酸1−エチルヘキシル、パルミチン酸1−エチルヘキシル、カプロン酸2−メチルペンチル、カプリル酸2−メチルペンチル、カプリン酸2−メチルペンチル、ラウリン酸2−メチルペンチル、ステアリン酸2−メチルブチル、ステアリン酸2−メチルブチル、ステアリン酸3−メチルブチル、ステアリン酸1−メチルヘプチル、ベヘン酸2−メチルブチル、ベヘン酸3−メチルブチル、ステアリン酸1−メチルヘプチル、ベヘン酸1−メチルヘプチル、カプロン酸1−エチルペンチル、パルミチン酸1−エチルペンチル、ステアリン酸1−メチルプロピル、ステアリン酸1−メチルオクチル、ステアリン酸1−メチルヘキシル、ラウリン酸1,1−ジメチルプロピル、カプリン酸1−メチルペンチル、パルミチン酸2−メチルヘキシル、ステアリン酸2−メチルヘキシル、ベヘン酸2−メチルヘキシル、ラウリン酸3,7−ジメチルオクチル、ミリスチン酸3,7−ジメチルオクチル、パルミチン酸3,7−ジメチルオクチル、ステアリン酸3,7−ジメチルオクチル、ベヘン酸3,7−ジメチルオクチル、オレイン酸ステアリル、オレイン酸ベヘニル、リノール酸ステアリル、リノール酸ベヘニル、エルカ酸3,7−ジメチルオクチル、エルカ酸ステアリル、エルカ酸イソステアリル、イソステアリン酸セチル、イソステアリン酸ステアリル、12−ヒドロキシステアリン酸2−メチルペンチル、18−ブロモステアリン酸2−エチルヘキシル、2−ケトミリスチン酸イソステアリル、2−フルオロミリスチン酸2−エチルヘキシル、酪酸セチル、酪酸ステアリル、酪酸ベヘニル等を例示できる。
In addition, esters of saturated fatty acids and branched fatty alcohols, unsaturated fatty acids or branched or substituted saturated fatty acids and esters of fatty alcohols having 16 or more carbon atoms, cetyl butyrate, stearyl butyrate and Ester compounds selected from behenyl butyrate are also effective.
Specifically, 2-ethylhexyl butyrate, 2-ethylhexyl behenate, 2-ethylhexyl myristate, 2-ethylhexyl caprate, 3,5,5-trimethylhexyl laurate, 3,5,5-trimethylhexyl palmitate, 3,5,5-trimethylhexyl stearate, 2-methylbutyl caproate, 2-methylbutyl caprylate, 2-methylbutyl caprate, 1-ethylpropyl palmitate, 1-ethylpropyl stearate, 1-ethylpropyl behenate, 1-ethylhexyl laurate, 1-ethylhexyl myristate, 1-ethylhexyl palmitate, 2-methylpentyl caproate, 2-methylpentyl caprylate, 2-methylpentyl caprate, 2-methylpentyl laurate, 2-stearate Mechi Butyl, 2-methylbutyl stearate, 3-methylbutyl stearate, 1-methylheptyl stearate, 2-methylbutyl behenate, 3-methylbutyl behenate, 1-methylheptyl stearate, 1-methylheptyl behenate, caproic acid 1 -Ethylpentyl, 1-ethylpentyl palmitate, 1-methylpropyl stearate, 1-methyloctyl stearate, 1-methylhexyl stearate, 1,1-dimethylpropyl laurate, 1-methylpentyl caprate, palmitic acid 2-methylhexyl, 2-methylhexyl stearate, 2-methylhexyl behenate, 3,7-dimethyloctyl laurate, 3,7-dimethyloctyl myristate, 3,7-dimethyloctyl palmitate, 3, stearate 7-Jime Ruoctyl, 3,7-dimethyloctyl behenate, stearyl oleate, behenyl oleate, stearyl linoleate, behenyl linoleate, 3,7-dimethyloctyl erucate, stearyl erucate, isostearyl erucate, cetyl isostearate, isostearic acid Examples include stearyl acid, 2-methylpentyl 12-hydroxystearate, 2-ethylhexyl 18-bromostearate, isostearyl 2-ketomyristate, 2-ethylhexyl 2-fluoromyristate, cetyl butyrate, stearyl butyrate, behenyl butyrate, etc. it can.
更には、特公平4−17154号公報に開示したカルボン酸エステル化合物、例えば、分子中に置換芳香族環を含むカルボン酸エステル、無置換芳香族環を含むカルボン酸と炭素数10以上の脂肪族アルコールのエステル、分子中にシクロヘキシル基を含むカルボン酸エステル、炭素数6以上の脂肪酸と無置換芳香族アルコール又はフェノールのエステル、炭素数8以上の脂肪酸と分岐脂肪族アルコール又はエステル、ジカルボン酸と芳香族アルコール又は分岐脂肪族アルコールのエステル、ケイ皮酸ジベンジル、ステアリン酸ヘプチル、アジピン酸ジデシル、アジピン酸ジラウリル、アジピン酸ジミリスチル、アジピン酸ジセチル、アジピン酸ジステアリル、トリラウリン、トリミリスチン、トリステアリン、ジミリスチン、ジステアリン等を用いることもできる。 Furthermore, the carboxylic acid ester compound disclosed in Japanese Patent Publication No. 4-17154, for example, a carboxylic acid ester containing a substituted aromatic ring in the molecule, a carboxylic acid containing an unsubstituted aromatic ring, and an aliphatic having 10 or more carbon atoms Esters of alcohol, carboxylic acid ester having a cyclohexyl group in the molecule, fatty acid having 6 or more carbon atoms and unsubstituted aromatic alcohol or phenol, fatty acid having 8 or more carbon atoms and branched aliphatic alcohol or ester, dicarboxylic acid and aromatic Esters of aliphatic or branched aliphatic alcohols, dibenzyl cinnamate, heptyl stearate, didecyl adipate, dilauryl adipate, dimyristyl adipate, dicetyl adipate, distearyl adipate, trilaurin, trimyristin, tristearin, dimyristin , Distearin It can also be used.
炭素数9以上の奇数の脂肪族一価アルコールと炭素数が偶数の脂肪族カルボン酸から得られる脂肪酸エステル化合物、n−ペンチルアルコール又はn−ヘプチルアルコールと炭素数10乃至16の偶数の脂肪族カルボン酸より得られる総炭素数17乃至23の脂肪酸エステル化合物も有効である。
具体的には、酢酸n−ペンタデシル、酪酸n−トリデシル、酪酸n−ペンタデシル、カプロン酸n−ウンデシル、カプロン酸n−トリデシル、カプロン酸n−ペンタデシル、カプリル酸n−ノニル、カプリル酸n−ウンデシル、カプリル酸n−トリデシル、カプリル酸n−ペンタデシル、カプリン酸n−ヘプチル、カプリン酸n−ノニル、カプリン酸n−ウンデシル、カプリン酸n−トリデシル、カプリン酸n−ペンタデシル、ラウリン酸n−ペンチル、ラウリン酸n−ヘプチル、ラウリン酸n−ノニル、ラウリン酸n−ウンデシル、ラウリン酸n−トリデシル、ラウリン酸n−ペンタデシル、ミリスチン酸n−ペンチル、ミリスチン酸n−ヘプチル、ミリスチン酸n−ノニル、ミリスチン酸n−ウンデシル、ミリスチン酸n−トリデシル、ミリスチン酸n−ペンタデシル、パルミチン酸n−ペンチル、パルミチン酸n−ヘプチル、パルミチン酸n−ノニル、パルミチン酸n−ウンデシル、パルミチン酸n−トリデシル、パルミチン酸n−ペンタデシル、ステアリン酸n−ノニル、ステアリン酸n−ウンデシル、ステアリン酸n−トリデシル、ステアリン酸n−ペンタデシル、エイコサン酸n−ノニル、エイコサン酸n−ウンデルシ、エイコサン酸n−トリデシル、エイコサン酸n−ペンタデシル、ベヘン酸n−ノニル、ベヘン酸n−ウンデシル、ベヘン酸n−トリデシル、ベヘン酸n−ペンタデシルを例示できる。
Fatty acid ester compound obtained from an odd aliphatic monohydric alcohol having 9 or more carbon atoms and an aliphatic carboxylic acid having an even carbon number, n-pentyl alcohol or n-heptyl alcohol and an even aliphatic carboxylic acid having 10 to 16 carbon atoms A fatty acid ester compound having a total carbon number of 17 to 23 obtained from an acid is also effective.
Specifically, n-pentadecyl acetate, n-tridecyl butyrate, n-pentadecyl butyrate, n-undecyl caproate, n-tridecyl caproate, n-pentadecyl caproate, n-nonyl caprylate, n-undecyl caprylate, N-tridecyl caprylate, n-pentadecyl caprylate, n-heptyl caprate, n-nonyl caprate, n-undecyl caprate, n-tridecyl caprate, n-pentadecyl caprate, n-pentyl laurate, lauric acid n-heptyl, n-nonyl laurate, n-undecyl laurate, n-tridecyl laurate, n-pentadecyl laurate, n-pentyl myristate, n-heptyl myristate, n-nonyl myristate, n-myristate Undecyl, n-tridecyl myristate, N-pentadecyl ristinate, n-pentyl palmitate, n-heptyl palmitate, n-nonyl palmitate, n-undecyl palmitate, n-tridecyl palmitate, n-pentadecyl palmitate, n-nonyl stearate, stearic acid n-undecyl, n-tridecyl stearate, n-pentadecyl stearate, n-nonyl eicosanoate, n-underci eicosanoate, n-tridecyl eicosanoate, n-pentadecyl eicosanoate, n-nonyl behenate, n-behenate Examples include undecyl, n-tridecyl behenate, and n-pentadecyl behenate.
アルコール類としては、デシルアルコール、ウンデシルアルコール、ドデシルアルコール、トリデシルアルコール、テトラデシルアルコール、ペンタデシルアルコール、ヘキサデシルアルコール、ヘプタデシルアルコール、オクタデシルアルコール、エイコシルアルコール、ドコシルアルコール等の脂肪族一価の飽和アルコール、アリルアルコール、オレイルアルコール等の脂肪族不飽和アルコール、シクロペンタノール、シクロヘキサノール、シクロオクタノール、シクロドデカノール、4−tert−ブチルシクロヘキサノール等の脂環式アルコール、4−メチルベンジルアルコール、ベンツヒドロール等の芳香族アルコール、ポリエチレングリコール等の多価アルコールを例示できる。 Alcohols include aliphatic decyl alcohol, undecyl alcohol, dodecyl alcohol, tridecyl alcohol, tetradecyl alcohol, pentadecyl alcohol, hexadecyl alcohol, heptadecyl alcohol, octadecyl alcohol, eicosyl alcohol, docosyl alcohol, etc. Aliphatic unsaturated alcohols such as saturated saturated alcohols, allyl alcohols and oleyl alcohols, cyclopentanols, cyclohexanols, cyclooctanols, cyclododecanols, alicyclic alcohols such as 4-tert-butylcyclohexanols, 4-methylbenzyl Examples thereof include aromatic alcohols such as alcohol and benzhydrol, and polyhydric alcohols such as polyethylene glycol.
酸アミド類としては、アセトアミド、プロピオン酸アミド、酪酸アミド、カプロン酸アミド、カプリル酸アミド、カプリン酸アミド、ラウリン酸アミド、ミリスチン酸アミド、パルミチン酸アミド、ステアリン酸アミド、ベヘン酸アミド、オレイン酸アミド、エルカ酸アミド、ベンズアミド、カプロン酸アニリド、カプリル酸アニリド、カプリン酸アニリド、ラウリン酸アニリド、ミリスチン酸アニリド、パルミチン酸アニリド、ステアリン酸アニリド、ベヘニン酸アニリド、オレイン酸アニリド、エルカ酸アニリド、カプロン酸N−メチルアミド、カプリル酸N−メチルアミド、カプリン酸N−メチルアミド、ラウリン酸N−メチルアミド、ミリスチン酸N−メチルアミド、パルミチン酸N−メチルアミド、ステアリン酸N−メチルアミド、ベヘン酸N−メチルアミド、オレイン酸N−メチルアミド、エルカ酸N−メチルアミド、ラウリン酸N−エチルアミド、ミリスチン酸N−エチルアミド、パルミチン酸N−エチルアミド、ステアリン酸N−エチルアミド、オレイン酸N−エチルアミド、ラウリン酸N−ブチルアミド、ミリスチン酸N−ブチルアミド、パルミチン酸N−ブチルアミド、ステアリン酸N−ブチルアミド、オレイン酸N−ブチルアミド、ラウリン酸N−オクチルアミド、ミリスチン酸N−オクチルアミド、パルミチン酸N−オクチルアミド、ステアリン酸N−オクチルアミド、オレイン酸N−オクチルアミド、ラウリン酸N−ドデシルアミド、ミリスチン酸N−ドデシルアミド、パルミチン酸N−ドデシルアミド、ステアリン酸N−ドデシルアミド、オレイン酸N−ドデシルアミド、ジラウリン酸アミド、ジミリスチン酸アミド、ジパルミチン酸アミド、ジステアリン酸アミド、ジオレイン酸アミド、トリラウリン酸アミド、トリミリスチン酸アミド、トリパルミチン酸アミド、トリステアリン酸アミド、トリオレイン酸アミド、コハク酸アミド、アジピン酸アミド、グルタル酸アミド、マロン酸アミド、アゼライン酸アミド、マレイン酸アミド、コハク酸N−メチルアミド、アジピン酸N−メチルアミド、グルタル酸N−メチルアミド、マロン酸N−メチルアミド、アゼライン酸N−メチルアミド、コハク酸N−エチルアミド、アジピン酸N−エチルアミド、グルタル酸N−エチルアミド、マロン酸N−エチルアミド、アゼライン酸N−エチルアミド、コハク酸N−ブチルアミド、アジピン酸N−ブチルアミド、グルタル酸N−ブチルアミド、マロン酸N−ブチルアミド、アジピン酸N−オクチルアミド、アジピン酸N−ドデシルアミド等を例示できる。 Acid amides include acetamide, propionic acid amide, butyric acid amide, caproic acid amide, caprylic acid amide, capric acid amide, lauric acid amide, myristic acid amide, palmitic acid amide, stearic acid amide, behenic acid amide, oleic acid amide , Erucic acid amide, benzamide, caproic acid anilide, caprylic acid anilide, capric acid anilide, lauric acid anilide, myristic acid anilide, palmitic acid anilide, stearic acid anilide, behenic acid anilide, oleic acid anilide, erucic acid anilide, caproic acid N -Methylamide, caprylic acid N-methylamide, capric acid N-methylamide, lauric acid N-methylamide, myristic acid N-methylamide, palmitic acid N-methylamide, stearic acid N-methylamide Behenic acid N-methylamide, oleic acid N-methylamide, erucic acid N-methylamide, lauric acid N-ethylamide, myristic acid N-ethylamide, palmitic acid N-ethylamide, stearic acid N-ethylamide, oleic acid N-ethylamide, lauric acid N-butyramide, myristic acid N-butylamide, palmitic acid N-butyramide, stearic acid N-butyramide, oleic acid N-butyramide, lauric acid N-octylamide, myristic acid N-octylamide, palmitic acid N-octylamide, stearin Acid N-octylamide, oleic acid N-octylamide, lauric acid N-dodecylamide, myristic acid N-dodecylamide, palmitic acid N-dodecylamide, stearic acid N-dodecylamide, oleic acid -Dodecylamide, dilauric acid amide, dimyristic acid amide, dipalmitic acid amide, distearic acid amide, dioleic acid amide, trilauric acid amide, trimyristic acid amide, tripalmitic acid amide, tristearic acid amide, trioleic acid amide, Succinic acid amide, adipic acid amide, glutaric acid amide, malonic acid amide, azelaic acid amide, maleic acid amide, succinic acid N-methylamide, adipic acid N-methylamide, glutaric acid N-methylamide, malonic acid N-methylamide, azelaic acid N-methylamide, succinic acid N-ethylamide, adipic acid N-ethylamide, glutaric acid N-ethylamide, malonic acid N-ethylamide, azelaic acid N-ethylamide, succinic acid N-butylamide, adipic acid N-buty Examples include luamide, glutaric acid N-butyramide, malonic acid N-butylamide, adipic acid N-octylamide, and adipic acid N-dodecylamide.
前記した(イ)、(ロ)、(ハ)からなる必須三成分を含むことにより可逆熱変色性組成物を得ることができる。
尚、前記(イ)、(ロ)、(ハ)成分の配合割合は、濃度、変色温度、変色形態や各成分の種類に左右されるが、一般的に所望の変色特性が得られる成分比は、(イ)成分1に対して、(ロ)成分0.1〜50、好ましくは0.5〜20、(ハ)成分1〜800、好ましくは5〜200の範囲である(前記割合はいずれも重量部である)。
A reversible thermochromic composition can be obtained by including the essential three components consisting of (a), (b) and (c).
The mixing ratio of the components (A), (B), and (C) depends on the concentration, the color change temperature, the color change form, and the type of each component, but generally the component ratio that provides the desired color change characteristics. Is (B) component 0.1 to 50, preferably 0.5 to 20, (C) component 1 to 800, preferably 5 to 200 (the ratio is All are parts by weight).
更に、前記可逆熱変色性組成物中に、石油系炭化水素樹脂を含有させることにより、自然消色温度域(X)で温度を一定に保った際、消色を促進させることができる。
前記石油系炭化水素樹脂としては、
低分子量ポリスチレン樹脂〔三洋化成(株)製、商品名:ハイマーST−95(分子量5,000)〕、〔三洋化成(株)製、商品名:ハイマーST−130、分子量50,000〕、〔三洋化成(株)製、商品名:ハイマーST−150、分子量60,000〕、〔理化ハーキュレス(株)製、商品名:ピコラスティックA−5、分子量317〕、〔理化ハーキュレス(株)製、商品名:ピコラスティックA−25、分子量348〕、[理化ハーキュレス(株)製、商品名:ピコラスティックA−75、分子量917〕、〔理化ハーキュレス(株)製、商品名:ピコラスティックD−125、分子量53,200〕、〔理化ハーキュレス(株)製、商品名:ピコラスティックD−150〕、〔理化ハーキュレス(株)製、商品名:エンデックス155、分子量6, 200〕、〔理化ハーキュレス(株)製、商品名:エンデックス160、分子量8, 200〕、
アクリルスチレン共重合樹脂〔三洋化成(株)製、商品名:ハイマーSBM−100、分子量15,000〕、〔三洋化成(株)製、商品名:ハイマーSBM−73F、分子量40,000〕、〔三洋化成(株)製、商品名:ハイマーSAM−955、分子量10,000〕、
テルペン系樹脂〔理化ハーキュレス(株)製、商品名:ピコライトA−115、分子量833〕、〔理化ハーキュレス(株)製、商品名:ピコライトS−115、分子量1,710〕、〔理化ハーキュレス(株)製、商品名:ピコライトC−115、分子量902〕、
フェノール変性テルペン樹脂〔理化ハーキュレス(株)製、商品名:ピコフィンT−125〕、〔理化ハーキュレス(株)製、商品名:ピコフィンA−125〕、
α−メチルスチレン樹脂〔理化ハーキュレス(株)製、商品名:クリスタレックス3085、分子量664〕、〔理化ハーキュレス(株)製、商品名:クリスタレックス5140、分子量3,950〕、〔理化ハーキュレス(株)製、商品名:クリスタレックス3025〕、〔理化ハーキュレス(株)製、商品名:クリスタレックス3070〕、〔理化ハーキュレス(株)製、商品名:クリスタレックス3100、分子量1020〕、〔理化ハーキュレス(株)製、商品名:クリスタレックス1120、分子量2420〕、
ビニルスチレン/α−メチルスチレン共重合樹脂〔理化ハーキュレス(株)製、商品名:ピコテックスLC、分子量950〕、〔理化ハーキュレス(株)製、商品名:ピコテックス100、分子量1,740〕、〔理化ハーキュレス(株)製、商品名:ピコテックス120、分子量3,190〕、
石油系不飽和炭化水素樹脂〔理化ハーキュレス(株)製、商品名:ピコタックB、分子量1,890〕、〔理化ハーキュレス(株)製、商品名:ピコタック95、分子量1,410〕、〔理化ハーキュレス(株)製、商品名:ピコペール100、分子量3,120〕、水添石油系樹脂〔理化ハーキュレス(株)製、商品名:リガレッツ−1018、分子量407〕、〔理化ハーキュレス(株)製、商品名:リガレッツ−1078、分子量819〕、〔理化ハーキュレス(株)製、商品名:リガレッツ−1094 分子量535〕等を例示できる。
Further, by including a petroleum hydrocarbon resin in the reversible thermochromic composition, decolorization can be promoted when the temperature is kept constant in the natural decoloring temperature range (X).
As the petroleum hydrocarbon resin,
Low molecular weight polystyrene resin [manufactured by Sanyo Kasei Co., Ltd., trade name: Hymer ST-95 (molecular weight 5,000)], [manufactured by Sanyo Kasei Co., Ltd., trade name: Hymer ST-130, molecular weight 50,000], [ Sanyo Chemical Co., Ltd., trade name: Heimer ST-150, molecular weight 60,000], [Rika Hercules Co., Ltd., trade name: pico-stick A-5, molecular weight 317], [Rika Hercules Co., Ltd., Product name: Picola stick A-25, molecular weight 348], [Rika Hercules Co., Ltd., trade name: Picola stick A-75, molecular weight 917], [Rika Hercules Co., Ltd., trade name: Picola stick D-125 , Molecular weight 53,200], [Rika Hercules Co., Ltd., trade name: Picola stick D-150], [Rika Hercules Co., Ltd., trade name: Endeck Scan 155, molecular weight of 6, 200], [Rika Hercules Co., Ltd. under the trade name: en index 160, molecular weight of 8, 200],
Acrylic styrene copolymer resin [manufactured by Sanyo Kasei Co., Ltd., trade name: Hymer SBM-100, molecular weight 15,000], [manufactured by Sanyo Kasei Co., Ltd., trade name: Hymer SBM-73F, molecular weight 40,000], [ Sanyo Chemical Co., Ltd., trade name: Hymer SAM-955, molecular weight 10,000],
Terpene resin [Rika Hercules Co., Ltd., trade name: Picolite A-115, molecular weight 833], [Rika Hercules Co., Ltd., trade name: Picolite S-115, molecular weight 1,710], [Rika Hercules Co., Ltd. Product name: Picolite C-115, molecular weight 902],
Phenol-modified terpene resin [Rika Hercules Co., Ltd., trade name: Picofin T-125], [Rika Hercules Co., Ltd., trade name: Picofin A-125],
α-methylstyrene resin (Rika Hercules Co., Ltd., trade name: Crystallex 3085, molecular weight 664), [Rika Hercules Co., Ltd., trade name: Crystallex 5140, molecular weight 3,950], [Rika Hercules Co., Ltd. Product name: Crystallex 3025], [Rika Hercules Co., Ltd., product name: Crystallex 3070], [Rika Hercules Co., Ltd., product name: Crystallex 3100, molecular weight 1020], [Rika Hercules ( Product name: Crystallex 1120, molecular weight 2420],
Vinylstyrene / α-methylstyrene copolymer resin (Rika Hercules Co., Ltd., trade name: Picotex LC, molecular weight 950), [Rika Hercules Co., Ltd., trade name: Picotex 100, molecular weight 1,740], [Rika Hercules Co., Ltd., trade name: Picotex 120, molecular weight 3,190],
Petroleum unsaturated hydrocarbon resin [Rika Hercules Co., Ltd., trade name: Picotac B, molecular weight 1,890], [Rika Hercules Co., Ltd., trade name: Picotac 95, molecular weight 1,410], [Rika Hercules Product name: Pico Pale 100, molecular weight 3,120], hydrogenated petroleum resin [Rika Hercules Co., Ltd., product name: Rigarets-1018, molecular weight 407], [Rika Hercules Co., Ltd., product Name: Rigarets-1078, molecular weight 819], [Rika Hercules Co., Ltd., trade name: Rigalets-1094 molecular weight 535] and the like.
なお、可逆熱変色性組成物の光劣化を防止するために光安定剤を0.3〜24重量部、好ましくは0.8〜16重量部の割合で含有することができる。
前記光安定剤としては、(イ)成分の光反応による励起状態によって生ずる光劣化を防止する紫外線吸収剤、酸化防止剤や、カロチン類、色素類、アミン類、フェノール類、ニッケル錯体類、スルフィド類等の一重項酸素消光剤、オキシドジスムスターゼとコバルト、及びニッケルの錯体等のスーパーオキシドアニオン消光剤、オゾン消光剤等の酸化反応を抑制する化合物を挙げることができる。
In order to prevent photodegradation of the reversible thermochromic composition, the light stabilizer can be contained in an amount of 0.3 to 24 parts by weight, preferably 0.8 to 16 parts by weight.
Examples of the light stabilizer include ultraviolet absorbers, antioxidants, carotenes, dyes, amines, phenols, nickel complexes, sulfides that prevent photodegradation caused by the excited state due to the photoreaction of component (a). Examples thereof include singlet oxygen quenchers such as superoxide anion quenchers such as complexes of oxide dismutase and cobalt and nickel, and compounds that suppress oxidation reactions such as ozone quenchers.
前記した可逆熱変色性組成物はマイクロカプセルに内包したり、樹脂中に分散して顔料形態として使用することが好ましい。これにより、種々の使用条件において可逆熱変色性組成物を同一の組成に保ち、化学的、物理的に安定な顔料を構成でき、同一の作用効果を奏することができる。
前記マイクロカプセル化は、従来より公知の界面重合法、in Situ重合法、液中硬化被覆法、水溶液からの相分離法、有機溶媒からの相分離法、融解分散冷却法、気中懸濁被覆法、スプレードライング法等があり、用途に応じて適宜選択される。更にマイクロカプセルの表面には、目的に応じて更に二次的な樹脂皮膜を設けて耐久性を付与させたり、表面特性を改質させて実用に供することもできる。
マイクロカプセル中に可逆熱変色性組成物を内包する際、前記光安定剤は可逆熱変色性組成物と共にマイクロカプセルに内包してもよいし、色材として適用される際に用いられるビヒクル中に添加することもできる。又、前記光安定剤をマイクロカプセルに内包すると共に、ビヒクル中にも添加することができる。
The reversible thermochromic composition described above is preferably encapsulated in microcapsules or dispersed in a resin and used as a pigment. Thereby, the reversible thermochromic composition can be maintained in the same composition under various use conditions, and a chemically and physically stable pigment can be constituted, and the same effects can be achieved.
The microencapsulation includes conventionally known interfacial polymerization method, in situ polymerization method, in-liquid curing coating method, phase separation method from aqueous solution, phase separation method from organic solvent, melt dispersion cooling method, air suspension coating Method, spray drying method, etc., which are appropriately selected according to the application. Further, a secondary resin film may be provided on the surface of the microcapsule according to the purpose to impart durability, or the surface characteristics may be modified for practical use.
When the reversible thermochromic composition is encapsulated in the microcapsule, the light stabilizer may be encapsulated in the microcapsule together with the reversible thermochromic composition, or in a vehicle used when applied as a coloring material. It can also be added. In addition, the light stabilizer can be encapsulated in a microcapsule and added to the vehicle.
本発明の可逆熱変色性組成物又はそれを用いた顔料は、各種ビヒクルに分散して、印刷インキや塗料の形態として印刷物、塗装物を得たり、成形用樹脂にブレンドして汎用の成形手段により各種の成形体を得ることができる。また、ワックス状或いはペースト状媒体に分散させて色材の形態となすこともできる。
更に、非熱変色性の染料、或いは顔料を適宜、併用して、色変化を多彩化させることができる。
前記可逆熱変色性組成物を用いることにより、示温分野、装飾分野、玩具分野、教習要素等、多様な分野に適用性を有する。
The reversible thermochromic composition of the present invention or a pigment using the same is dispersed in various vehicles to obtain a printed material or a coated material in the form of printing ink or paint, or blended with a molding resin for general-purpose molding means. Thus, various molded products can be obtained. Further, it can be dispersed in a waxy or pasty medium to form a color material.
Furthermore, the color change can be diversified by appropriately using a non-thermochromic dye or pigment in combination.
By using the reversible thermochromic composition, the composition has applicability in various fields such as a temperature display field, a decoration field, a toy field, and a learning element.
以下に実施例を示すが、本発明は実施例に限定されるものではない。
実施例1
可逆熱変色性組成物を内包したマイクロカプセル顔料の調製
(イ)成分として2−(ジブチルアミノ)−8−(ジペンチルアミノ)−4−メチル−スピロ〔5H−〔1〕ベンゾピラノ〔2,3−g〕ピリミジン−5,1′(3′H)−イソベンゾフラン〕−3−オン1.0重量部、(ロ)成分として4,4′−オキシビスフェノール6.0重量部、(ハ)成分としてカプリン酸ステアリル30.0重量部、セチルアルコール15.0重量部からなる可逆熱変色性組成物を均一に加温溶解し、壁膜材料として芳香族イソシアネートプレポリマー30.0重量部、助溶剤50.0重量部を加えた後、8%ポリビニルアルコール水溶液中で乳化した。
乳化後、水溶性脂肪族変性アミン2.5重量部を加え、更に攪拌を続けて可逆熱変色性マイクロカプセル顔料懸濁液を得た。
前記可逆熱変色性マイクロカプセル顔料懸濁液を遠心分離によりマイクロカプセル顔料を単離した。
尚、前記マイクロカプセル顔料はピンク色から無色の可逆的熱変色性を示す。
Examples are shown below, but the present invention is not limited to the examples.
Example 1
Preparation of Microcapsule Pigment Encapsulating Reversible Thermochromic Composition (A) 2- (Dibutylamino) -8- (dipentylamino) -4-methyl-spiro [5H- [1] benzopyrano [2,3- g) Pyrimidine-5,1 ′ (3′H) -isobenzofuran] -3-one 1.0 part by weight, (b) component 4,4′-oxybisphenol 6.0 part by weight, (c) component A reversible thermochromic composition composed of 30.0 parts by weight of stearyl caprate and 15.0 parts by weight of cetyl alcohol is uniformly heated and dissolved, and 30.0 parts by weight of an aromatic isocyanate prepolymer as a wall film material, and a cosolvent 50 After adding 0.0 part by weight, the mixture was emulsified in an 8% aqueous polyvinyl alcohol solution.
After emulsification, 2.5 parts by weight of a water-soluble aliphatic modified amine was added, and stirring was continued to obtain a reversible thermochromic microcapsule pigment suspension.
The microcapsule pigment was isolated by centrifuging the reversible thermochromic microcapsule pigment suspension.
The microcapsule pigment exhibits a reversible thermochromic property from pink to colorless.
実施例2
可逆熱変色性組成物を内包したマイクロカプセル顔料の調製
(イ)成分として2−(ジブチルアミノ)−8−(ジペンチルアミノ)−4−メチル−スピロ〔5H−〔1〕ベンゾピラノ〔2,3−g〕ピリミジン−5,1′(3′H)−イソベンゾフラン〕−3−オン1.0重量部、(ロ)成分として4,4′−オキシビスフェノール6.0重量部、(ハ)成分としてカプリン酸ステアリル30.0重量部、セチルアルコール15.0重量部、消色促進剤として石油系炭化水素樹脂〔理化ハーキュレス(株)製、商品名:クリスタレックス3085〕5.0重量部からなる可逆熱変色性組成物を均一に加温溶解し、壁膜材料として芳香族イソシアネートプレポリマー30.0重量部、助溶剤50.0重量部を加えた後、8%ポリビニルアルコール水溶液中で乳化した。
乳化後、水溶性脂肪族変性アミン2.5重量部を加え、更に攪拌を続けて可逆熱変色性マイクロカプセル顔料懸濁液を得た。
前記可逆熱変色性マイクロカプセル顔料懸濁液を遠心分離によりマイクロカプセル顔料を単離した。
尚、前記マイクロカプセル顔料はピンク色から無色の可逆的熱変色性を示す。
Example 2
Preparation of Microcapsule Pigment Encapsulating Reversible Thermochromic Composition (A) 2- (Dibutylamino) -8- (dipentylamino) -4-methyl-spiro [5H- [1] benzopyrano [2,3- g) Pyrimidine-5,1 ′ (3′H) -isobenzofuran] -3-one 1.0 part by weight, (b) component 4,4′-oxybisphenol 6.0 part by weight, (c) component A reversible composition comprising 30.0 parts by weight of stearyl caprate, 15.0 parts by weight of cetyl alcohol, and 5.0 parts by weight of a petroleum hydrocarbon resin [manufactured by Rika Hercules Co., Ltd., trade name: Crystallex 3085] as a decoloring accelerator. The thermochromic composition is uniformly heated and dissolved. After adding 30.0 parts by weight of an aromatic isocyanate prepolymer and 50.0 parts by weight of a co-solvent as a wall film material, 8% polyvinyl alcohol is added. Emulsified in aqueous solution.
After emulsification, 2.5 parts by weight of a water-soluble aliphatic modified amine was added, and stirring was continued to obtain a reversible thermochromic microcapsule pigment suspension.
The microcapsule pigment was isolated by centrifuging the reversible thermochromic microcapsule pigment suspension.
The microcapsule pigment exhibits a reversible thermochromic property from pink to colorless.
実施例3
可逆熱変色性組成物を内包したマイクロカプセル顔料の調製
(イ)成分として2−(ジブチルアミノ)−8−(ジペンチルアミノ)−4−メチル−スピロ〔5H−〔1〕ベンゾピラノ〔2,3−g〕ピリミジン−5,1′(3′H)−イソベンゾフラン〕−3−オン1.0重量部、(ロ)成分として4,4′−オキシビスフェノール6.0重量部、(ハ)成分としてミリスチン酸ステアリル30.0重量部、ステアリルアルコール15.0重量部、消色促進剤として石油系炭化水素樹脂〔三洋化成(株)製、商品名:ピコラスティックA−75〕5.0重量部からなる可逆熱変色性組成物を均一に加温溶解し、壁膜材料として芳香族イソシアネートプレポリマー30.0重量部、助溶剤50.0重量部を加えた後、8%ポリビニルアルコール水溶液中で乳化した。
乳化後、水溶性脂肪族変性アミン2.5重量部を加え、更に攪拌を続けて可逆熱変色性マイクロカプセル顔料懸濁液を得た。
前記可逆熱変色性マイクロカプセル顔料懸濁液を遠心分離によりマイクロカプセル顔料を単離した。
尚、前記マイクロカプセル顔料はピンク色から無色の可逆的熱変色性を示す。
Example 3
Preparation of Microcapsule Pigment Encapsulating Reversible Thermochromic Composition (A) 2- (Dibutylamino) -8- (dipentylamino) -4-methyl-spiro [5H- [1] benzopyrano [2,3- g) Pyrimidine-5,1 ′ (3′H) -isobenzofuran] -3-one 1.0 part by weight, (b) component 4,4′-oxybisphenol 6.0 part by weight, (c) component From 30.0 parts by weight of stearyl myristate, 15.0 parts by weight of stearyl alcohol, and 5.0 parts by weight of petroleum hydrocarbon resin [manufactured by Sanyo Chemical Co., Ltd., trade name: Picola stick A-75] as a decolorization accelerator. The reversible thermochromic composition is uniformly heated and dissolved, and 30.0 parts by weight of an aromatic isocyanate prepolymer and 50.0 parts by weight of a co-solvent are added as a wall film material, and then 8% polyvinyl alcohol. Emulsified in an aqueous solution.
After emulsification, 2.5 parts by weight of a water-soluble aliphatic modified amine was added, and stirring was continued to obtain a reversible thermochromic microcapsule pigment suspension.
The microcapsule pigment was isolated by centrifuging the reversible thermochromic microcapsule pigment suspension.
The microcapsule pigment exhibits a reversible thermochromic property from pink to colorless.
実施例4
可逆熱変色性組成物を内包したマイクロカプセル顔料の調製
(イ)成分として2−(ジブチルアミノ)−8−(ジペンチルアミノ)−4−メチル−スピロ〔5H−〔1〕ベンゾピラノ〔2,3−g〕ピリミジン−5,1′(3′H)−イソベンゾフラン〕−3−オン1.0重量部、(ロ)成分として4,4′−オキシビスフェノール6.0重量部、(ハ)成分としてラウリン酸ステアリル30.0重量部、ステアリルアルコール15.0重量部、消色促進剤として石油系炭化水素樹脂〔三洋化成(株)製、商品名:ピコラスティックA−75〕5.0重量部からなる可逆熱変色性組成物を均一に加温溶解し、壁膜材料として芳香族イソシアネートプレポリマー30.0重量部、助溶剤50.0重量部を加えた後、8%ポリビニルアルコール水溶液中で乳化した。
乳化後、水溶性脂肪族変性アミン2.5重量部を加え、更に攪拌を続けて可逆熱変色性マイクロカプセル顔料懸濁液を得た。
前記可逆熱変色性マイクロカプセル顔料懸濁液を遠心分離によりマイクロカプセル顔料を単離した。
尚、前記マイクロカプセル顔料はピンク色から無色の可逆的熱変色性を示す。
Example 4
Preparation of Microcapsule Pigment Encapsulating Reversible Thermochromic Composition (A) 2- (Dibutylamino) -8- (dipentylamino) -4-methyl-spiro [5H- [1] benzopyrano [2,3- g) Pyrimidine-5,1 ′ (3′H) -isobenzofuran] -3-one 1.0 part by weight, (b) component 4,4′-oxybisphenol 6.0 part by weight, (c) component From 30.0 parts by weight of stearyl laurate, 15.0 parts by weight of stearyl alcohol, 5.0 parts by weight of petroleum-based hydrocarbon resin [manufactured by Sanyo Chemical Co., Ltd., trade name: Picorastic A-75] as a decolorization accelerator The reversible thermochromic composition is uniformly heated and dissolved, and 30.0 parts by weight of an aromatic isocyanate prepolymer and 50.0 parts by weight of a co-solvent are added as a wall film material. Emulsified in solution.
After emulsification, 2.5 parts by weight of a water-soluble aliphatic modified amine was added, and stirring was continued to obtain a reversible thermochromic microcapsule pigment suspension.
The microcapsule pigment was isolated by centrifuging the reversible thermochromic microcapsule pigment suspension.
The microcapsule pigment exhibits a reversible thermochromic property from pink to colorless.
実施例5
可逆熱変色性組成物を内包したマイクロカプセル顔料の調製
(イ)成分として2−(ジブチルアミノ)−8−(ジペンチルアミノ)−4−メチル−スピロ〔5H−〔1〕ベンゾピラノ〔2,3−g〕ピリミジン−5,1′(3′H)−イソベンゾフラン〕−3−オン1.0重量部、(ロ)成分として4,4′−オキシビスフェノール6.0重量部、(ハ)成分としてカプリン酸セチル30.0重量部、ミリスチルアルコール15.0重量部、消色促進剤として石油系炭化水素樹脂〔理化ハーキュレス(株)製、商品名:クリスタレックス3085〕5.0重量部からなる可逆熱変色性組成物を均一に加温溶解し、壁膜材料として芳香族イソシアネートプレポリマー30.0重量部、助溶剤50.0重量部を加えた後、8%ポリビニルアルコール水溶液中で乳化した。
乳化後、水溶性脂肪族変性アミン2.5重量部を加え、更に攪拌を続けて可逆熱変色性マイクロカプセル顔料懸濁液を得た。
前記可逆熱変色性マイクロカプセル顔料懸濁液を遠心分離によりマイクロカプセル顔料を単離した。
尚、前記マイクロカプセル顔料はピンク色から無色の可逆的熱変色性を示す。
Example 5
Preparation of Microcapsule Pigment Encapsulating Reversible Thermochromic Composition (A) 2- (Dibutylamino) -8- (dipentylamino) -4-methyl-spiro [5H- [1] benzopyrano [2,3- g) Pyrimidine-5,1 ′ (3′H) -isobenzofuran] -3-one 1.0 part by weight, (b) component 4,4′-oxybisphenol 6.0 part by weight, (c) component A reversible composition comprising 30.0 parts by weight of cetyl caprate, 15.0 parts by weight of myristyl alcohol, and 5.0 parts by weight of a petroleum hydrocarbon resin [manufactured by Rika Hercules Co., Ltd., trade name: Crystallex 3085] as a decoloring accelerator. The thermochromic composition is uniformly heated and dissolved. After adding 30.0 parts by weight of an aromatic isocyanate prepolymer and 50.0 parts by weight of a co-solvent as a wall film material, 8% polyvinyl alcohol is added. Emulsified in aqueous solution.
After emulsification, 2.5 parts by weight of a water-soluble aliphatic modified amine was added, and stirring was continued to obtain a reversible thermochromic microcapsule pigment suspension.
The microcapsule pigment was isolated by centrifuging the reversible thermochromic microcapsule pigment suspension.
The microcapsule pigment exhibits a reversible thermochromic property from pink to colorless.
比較例1
可逆熱変色性組成物を内包したマイクロカプセル顔料の調製
(ロ)成分として4,4′−(2−メチルプロピリデン)ビスフェノール6.0重量部を用いた以外は実施例1と同様の方法によりマイクロカプセル顔料を得た。
Comparative Example 1
Preparation of microcapsule pigment encapsulating reversible thermochromic composition (b) By the same method as in Example 1 except that 6.0 parts by weight of 4,4 '-(2-methylpropylidene) bisphenol was used as component. A microcapsule pigment was obtained.
比較例2
可逆熱変色性組成物を内包したマイクロカプセル顔料の調製
(ロ)成分として4,4′−(2−メチルプロピリデン)ビスフェノール6.0重量部を用いた以外は実施例3と同様の方法によりマイクロカプセル顔料を得た。
Comparative Example 2
Preparation of microcapsule pigment encapsulating reversible thermochromic composition (b) By the same method as in Example 3, except that 6.0 parts by weight of 4,4 '-(2-methylpropylidene) bisphenol was used as component. A microcapsule pigment was obtained.
比較例3
(ロ)成分として4,4′−(2−メチルプロピリデン)ビスフェノール6.0重量部を用いた以外は実施例4と同様の方法によりマイクロカプセル顔料を得た。
Comparative Example 3
A microcapsule pigment was obtained in the same manner as in Example 4 except that 6.0 parts by weight of 4,4 ′-(2-methylpropylidene) bisphenol was used as the component (b).
比較例4
(ロ)成分として4,4′−(2−メチルプロピリデン)ビスフェノール6.0重量部を用いた以外は実施例5と同様の方法によりマイクロカプセル顔料を得た。
Comparative Example 4
A microcapsule pigment was obtained in the same manner as in Example 5 except that 6.0 parts by weight of 4,4 ′-(2-methylpropylidene) bisphenol was used as the component (b).
測定試料の作成
前記各マイクロカプセル顔料40重量部をエチレン−酢酸ビニルエマルジョン中に分散した可逆熱変色性インキを用いて、スクリーン印刷により上質紙に所定の大きさの円を印刷して測定試料を得た。
Preparation of measurement sample Using a reversible thermochromic ink in which 40 parts by weight of each of the microcapsule pigments are dispersed in an ethylene-vinyl acetate emulsion, a circle of a predetermined size is printed on a high-quality paper by screen printing. Obtained.
変色温度測定
前記測定試料を色差計〔TC−3600型色差計、東京電色(株)製〕の所定箇所にセットし、10℃/分の速度で完全消色温度(T4 )以上まで加熱した後、10℃/分の速度で降温させて発色開始温度(T2 )を測定した。
その結果、実施例1、2、比較例1の測定試料の発色開始温度(T2 )は29℃であり、実施例3、比較例2の測定試料の発色開始温度(T2 )は42℃であり、実施例4、比較例3の測定試料の発色開始温度(T2 )は29℃であり、実施例5、比較例4の測定試料の発色開始温度(T2 )は20℃であった。
Discoloration temperature measurement The measurement sample is set at a predetermined position of a color difference meter [TC-3600 type color difference meter, manufactured by Tokyo Denshoku Co., Ltd.] and heated to a complete decoloring temperature (T 4 ) or higher at a rate of 10 ° C./min. Thereafter, the temperature was lowered at a rate of 10 ° C./min, and the color development start temperature (T 2 ) was measured.
As a result, the color development start temperature (T 2 ) of the measurement samples of Examples 1 and 2 and Comparative Example 1 was 29 ° C., and the color development start temperature (T 2 ) of the measurement samples of Example 3 and Comparative Example 2 was 42 ° C. The color development start temperature (T 2 ) of the measurement samples of Example 4 and Comparative Example 3 is 29 ° C., and the color development start temperature (T 2 ) of the measurement samples of Example 5 and Comparative Example 4 is 20 ° C. It was.
消色試験
実施例1、2、比較例1の各測定試料を色差計〔TC−3600型色差計、東京電色(株)製〕の所定箇所にセットし、25℃、20℃、15℃、10℃、5℃の各温度で1時間放置した後、明度値を測定した。
実施例3、比較例2の各測定試料を色差計〔TC−3600型色差計、東京電色(株)製〕の所定箇所にセットし、35℃、30℃、25℃、20℃、15℃の各温度で1時間放置した後、明度値を測定した。
実施例4、比較例3の各測定試料を色差計〔TC−3600型色差計、東京電色(株)製〕の所定箇所にセットし、25℃、20℃、15℃、10℃、5℃の各温度で1時間放置した後、明度値を測定した。
実施例5、比較例4の各測定試料を色差計〔TC−3600型色差計、東京電色(株)製〕の所定箇所にセットし、15℃、10℃、5℃、0℃、−5℃の各温度で1時間放置した後、明度値を測定した。
Discoloration test Each measurement sample of Examples 1 and 2 and Comparative Example 1 was set in a predetermined position of a color difference meter [TC-3600 type color difference meter, manufactured by Tokyo Denshoku Co., Ltd.], and 25 ° C, 20 ° C, 15 ° C. The lightness value was measured after standing at 10 ° C. and 5 ° C. for 1 hour.
Each measurement sample of Example 3 and Comparative Example 2 is set at a predetermined position of a color difference meter [TC-3600 type color difference meter, manufactured by Tokyo Denshoku Co., Ltd.], and 35 ° C., 30 ° C., 25 ° C., 20 ° C., 15 The lightness value was measured after standing at each temperature of 1 ° C. for 1 hour.
Each measurement sample of Example 4 and Comparative Example 3 was set at a predetermined position of a color difference meter [TC-3600 type color difference meter, manufactured by Tokyo Denshoku Co., Ltd.], and 25 ° C., 20 ° C., 15 ° C., 10 ° C., 5 The lightness value was measured after standing at each temperature of 1 ° C. for 1 hour.
Each measurement sample of Example 5 and Comparative Example 4 is set at a predetermined position of a color difference meter [TC-3600 type color difference meter, manufactured by Tokyo Denshoku Co., Ltd.], and is 15 ° C., 10 ° C., 5 ° C., 0 ° C., − After standing at each temperature of 5 ° C. for 1 hour, the brightness value was measured.
以下の表に各温度における明度値を示す。
T1 完全発色温度
T2 発色開始温度
T3 消色開始温度
T4 完全消色温度
T 1 complete color temperature T 2 color start temperature T 3 color erase start temperature T 4 complete color erase temperature
Claims (4)
T2 −20≦X≦T2 (1)
Y<T2 −20 (2) The reversible thermochromic composition according to claim 1, wherein the natural decoloring temperature range (X) satisfies the following formula (1), and the color development holding temperature range (Y) satisfies the following formula (2).
T 2 −20 ≦ X ≦ T 2 (1)
Y <T 2 -20 (2)
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JPH08311357A (en) * | 1995-05-17 | 1996-11-26 | Fuji Photo Film Co Ltd | Indolylazaphthalide compound and recording material using the compound |
JPH0931345A (en) * | 1995-05-17 | 1997-02-04 | Fuji Photo Film Co Ltd | Indolylazaphthalide compound and recording material using the same |
JPH1036725A (en) * | 1996-07-22 | 1998-02-10 | Pilot Ink Co Ltd | Microcapsule pigment having color memory of temperature-sensitive change in color |
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JP2000347447A (en) * | 1999-03-31 | 2000-12-15 | Toshiba Corp | Erasable image forming material, paper medium, method for erasing image, writing pen and thermal transfer ink ribbon |
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JPH01180382A (en) * | 1988-01-12 | 1989-07-18 | Oji Paper Co Ltd | Thermal recording material |
JPH05294063A (en) * | 1991-06-29 | 1993-11-09 | Ricoh Co Ltd | Reversible thermal color forming composition and recording medium and display medium using the same |
JPH0839936A (en) * | 1994-08-02 | 1996-02-13 | Pilot Ink Co Ltd | Temperature-sensitive color changeable hue memory composition |
JPH08276654A (en) * | 1995-04-07 | 1996-10-22 | Fuji Photo Film Co Ltd | Indolylazaphthalide compound and recording material employing it |
JPH08311356A (en) * | 1995-05-17 | 1996-11-26 | Fuji Photo Film Co Ltd | Indolylazaphthalide compound and recording material using the compound |
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JPH1036725A (en) * | 1996-07-22 | 1998-02-10 | Pilot Ink Co Ltd | Microcapsule pigment having color memory of temperature-sensitive change in color |
JPH1095174A (en) * | 1996-09-25 | 1998-04-14 | Oji Paper Co Ltd | Reversible thermal recording medium |
JP2000347447A (en) * | 1999-03-31 | 2000-12-15 | Toshiba Corp | Erasable image forming material, paper medium, method for erasing image, writing pen and thermal transfer ink ribbon |
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