JP6535236B2 - Reversible thermochromic microcapsule pigment - Google Patents
Reversible thermochromic microcapsule pigment Download PDFInfo
- Publication number
- JP6535236B2 JP6535236B2 JP2015129618A JP2015129618A JP6535236B2 JP 6535236 B2 JP6535236 B2 JP 6535236B2 JP 2015129618 A JP2015129618 A JP 2015129618A JP 2015129618 A JP2015129618 A JP 2015129618A JP 6535236 B2 JP6535236 B2 JP 6535236B2
- Authority
- JP
- Japan
- Prior art keywords
- ester
- general formula
- hydroxybenzoic acid
- compound
- alkyl group
- 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.)
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- 230000002441 reversible effect Effects 0.000 title claims description 49
- 239000003094 microcapsule Substances 0.000 title claims description 26
- 239000000049 pigment Substances 0.000 title claims description 25
- -1 Hydroxybenzoic acid ester compounds Chemical class 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 238000010438 heat treatment Methods 0.000 claims description 11
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 150000008282 halocarbons Chemical class 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 4
- 238000006276 transfer reaction Methods 0.000 claims description 4
- 238000002845 discoloration Methods 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000000034 method Methods 0.000 description 9
- XQXPVVBIMDBYFF-UHFFFAOYSA-N para-hydroxyphenylacetic acid Natural products OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
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- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 230000001747 exhibiting effect Effects 0.000 description 4
- 230000006698 induction Effects 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
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- 239000000126 substance Substances 0.000 description 4
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- 239000004593 Epoxy Substances 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- UYEMGAFJOZZIFP-UHFFFAOYSA-N alpha-resorcylic acid Natural products OC(=O)C1=CC(O)=CC(O)=C1 UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
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- 239000003973 paint Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
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- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
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- HMSWAIKSFDFLKN-UHFFFAOYSA-N Hexacosane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCC HMSWAIKSFDFLKN-UHFFFAOYSA-N 0.000 description 2
- 238000012695 Interfacial polymerization Methods 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
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- 239000000975 dye Substances 0.000 description 2
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- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- YYLACZAXCCJCJO-UHFFFAOYSA-N heptacos-1-ene Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC=C YYLACZAXCCJCJO-UHFFFAOYSA-N 0.000 description 2
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- 239000004611 light stabiliser Substances 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- IGGUPRCHHJZPBS-UHFFFAOYSA-N nonacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCC IGGUPRCHHJZPBS-UHFFFAOYSA-N 0.000 description 2
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Landscapes
- Heat Sensitive Colour Forming Recording (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Description
本発明は可逆熱変色性マイクロカプセル顔料に関する。更に詳細には、消色状態からの加熱により発色する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 reversibly thermochromic microcapsule pigments. More particularly, the present invention relates to a reversible thermochromic microcapsule pigment which develops color upon heating from a decolored state.
従来、（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）、（ロ）による電子授受反応を可逆的に生起させる反応媒体からなる可逆熱変色性組成物のうち、（ロ）成分としてヒドロキシ安息香酸エステルを用いることによって、消色状態からの加熱により発色状態を示し、降温により消色状態に復帰する変色挙動を示す可逆熱変色性組成物及びそれを内包したマイクロカプセル顔料が開示されている(例えば、特許文献１参照)。
前記可逆熱変色性組成物は、加熱により発色状態を示すものの、発色する温度が高く、日常生活温度や日常生活温度近傍の温度で容易に発色させることは困難であった。また、日常生活温度や日常生活温度近傍の温度で発色させる可逆熱変色性組成物が得られたとしても、発色状態における色濃度が低く、実用性を満足させていなかった。
そこで、（イ）、（ロ）、（ハ）成分と共に（ニ）成分として特定のスチレン系化合物を添加することにより、生活環境温度域や日常生活温度近傍の温度で容易に消色状態からの加熱により発色状態を呈し、再び消色状態に復帰する変色挙動を呈すると共に、発色時の色濃度が高い可逆熱変色性組成物を内包した可逆熱変色性マイクロカプセル顔料が開示されている(例えば、特許文献２参照)。
Conventionally, a reversible thermal discoloration comprising a reaction medium that reversibly causes the electron transfer reaction by (i) electron donating color forming organic compound, (ii) electron accepting compound, and (iii) the above (i) and (ii) Reversibly thermochromic composition exhibiting a color forming state by heating from a decoloring state by using a hydroxybenzoic acid ester as the component (ii) of the coloring composition and exhibiting a color changing behavior returning to the decoloring state by temperature lowering And the microcapsule pigment which included it is disclosed (for example, refer patent document 1).
Although the reversible thermochromic composition shows a colored state by heating, the temperature at which color is developed is high, and it has been difficult to easily develop color at temperatures close to the daily life temperature and the daily life temperature. In addition, even if a reversible thermochromic composition which produces color at a temperature of the daily life temperature or a temperature close to the daily life temperature is obtained, the color density in the colored state is low and the practicability is not satisfied.
Therefore, by adding a specific styrenic compound as the component (ii) together with the components (i), (ii) and (iii), it is possible to easily remove color from the decolored state at temperatures near the living environment temperature range and the daily life temperature. There is disclosed a reversible thermochromic microcapsule pigment which exhibits a color forming state by heating and returns to a decoloring state again and incorporates a reversible thermochromic composition having a high color density at the time of color forming (for example, , Patent Document 2).
本発明者らは、この種の可逆熱変色性組成物を内包した可逆熱変色性マイクロカプセル顔料について鋭意検討した結果、（イ）、（ロ）、（ハ）、（ニ）成分と共に（ホ）成分として特定の化合物を添加することによって、生活環境温度域や日常生活温度近傍の温度で容易に消色状態からの加熱により発色状態を呈し、再び消色状態に復帰する変色挙動を呈すると共に、消色時の色消えを向上させた可逆熱変色性組成物を内包した可逆熱変色性マイクロカプセル顔料が得られることを見出し、本発明を完成させた。 As a result of intensive investigations on reversibly thermochromic microcapsule pigments in which this type of reversibly thermochromic composition is contained, the present inventors found that (a), (b), (c) and (d) together with the components ) By adding a specific compound as a component, it exhibits a colored state by heating from the decolored state easily at temperatures near the living environment temperature range and the daily life temperature, and exhibits a color change behavior that returns to the decolored state again It has been found that a reversibly thermochromic microcapsule pigment containing a reversibly thermochromic composition having improved decoloring upon decoloring can be obtained, and the present invention has been completed.
本発明は、（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して下記一般式（１）で示されるヒドロキシ安息香酸エステル化合物と、（ハ）前記（イ）、（ロ）による電子授受反応を可逆的に生起させる反応媒体として鎖式炭化水素類、脂環族炭化水素類、芳香族炭化水素類、ハロゲン化炭化水素類から選ばれる化合物と、（ニ）軟化点が５℃以上、且つ、重量平均分子量が２００乃至１０万のスチレン系化合物と、（ホ）下記一般式（２）又は（３）から選ばれる化合物とからなる消色状態からの加熱により発色状態となる可逆熱変色性組成物をマイクロカプセルに内包した可逆熱変色性マイクロカプセル顔料を要件とする。
更には、前記一般式（１）で示されるヒドロキシ安息香酸エステル化合物のアルキル基が、炭素数１０乃至２０の直鎖アルキル基であること、前記（ロ）電子受容性化合物として一般式（１）で示されるヒドロキシ安息香酸エステル化合物と、下記一般式（４）で示されるヒドロキシフェニル酢酸エステル化合物を用いてなること等を要件とする。
Furthermore, the alkyl group of the hydroxybenzoic acid ester compound represented by the general formula (1) is a linear alkyl group having 10 to 20 carbon atoms, and the general formula (1) as the (ii) electron accepting compound And a hydroxyphenylacetic acid ester compound represented by the following general formula (4).
本発明は、生活環境温度域や日常生活温度近傍の温度で容易に消色状態からの加熱により発色状態を呈し、再び消色状態に復帰する可逆的変色挙動を呈すると共に、消色時の色消えを向上させた、教習要素、玩具、装飾等、多様な分野に適用可能な可逆熱変色性マイクロカプセル顔料を提供できる。 The present invention exhibits a reversible color change behavior in which a color development state is exhibited by heating from the color extinction state easily at a temperature near the living environment temperature range or the daily life temperature, and returns to the color extinction state again It is possible to provide reversible thermochromic microcapsule pigments applicable to various fields such as teaching elements, toys, decorations, etc. with improved fade-out.
前記（イ）電子供与性呈色性有機化合物としては、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、ピリジン類、キナゾリン類、ビスキナゾリン類等が挙げられる。
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−ジフェニルアミノフルオラン、
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−クロロアミノ）−６−ジブチ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−メトキシ−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−アニリノ−３−メトキシ−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−ｇ）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−ｇ）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−ｇ）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−ｇ）ピリミジン−５，１′（３′Ｈ）イソベンゾフラン〕−３−オン、
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、
３−（２−メトキシ−４−ジメチルアミノフェニル）−３−（１−ブチル−２−メチルインドール−３−イル）−４，５，６，７−テトラクロロフタリド、
３−（２−エトキシ−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）−４，５，６，７−テトラクロロフタリド、
３−（２−エトキシ−４−ジエチルアミノフェニル）−３−（１−ペンチル−２−メチルインドール−３−イル）−４，５，６，７−テトラクロロフタリド、
４，５，６，７−テトラクロロ−３−[４−（ジメチルアミノ）−２−メチルフェニル]−３−（１−エチル−２−メチル−１Ｈ−インドール−３−イル）−１（３Ｈ）−イソベンゾフラノン、
３′，６′−ビス〔フェニル（２−メチルフェニル）アミノ〕−スピロ［イソベンゾフラン−１（３Ｈ），９′−〔９Ｈ〕キサンテン］−３−オン、
３′，６′−ビス〔フェニル（３−メチルフェニル）アミノ〕−スピロ［イソベンゾフラン−１（３Ｈ），９′−〔９Ｈ〕キサンテン］−３−オン、
３′，６′−ビス〔フェニル（３−エチルフェニル）アミノ〕−スピロ［イソベンゾフラン−１（３Ｈ），９′−〔９Ｈ〕キサンテン］−３−オン、
４−［２，６−ビス（２−エトキシフェニル）−４−ピリジニル］−Ｎ，Ｎ−ジメチルベンゼンアミン、
２−（４′−ジメチルアミノフェニル）−４−メトキシ−キナゾリン、
４，４′−（エチレンジオキシ）−ビス〔２−（４−ジエチルアミノフェニル）キナゾリン〕等を挙げることができる。
なお、フルオラン類としては、キサンテン環を形成するフェニル基に置換基を有する前記化合物の他、キサンテン環を形成するフェニル基に置換基を有すると共にラクトン環を形成するフェニル基にも置換基（例えば、メチル基等のアルキル基、クロロ基等のハロゲン原子）を有する青色や黒色を呈する化合物であってもよい。
As the (i) electron donating color forming organic compound, diphenylmethane phthalides, phenyl indolyl phthalides, indolyl phthalides, diphenyl methane azaphthalides, phenyl indolyl azaphthalides, fluorans, Stylinoquinolines, diazarhodamine lactones, pyridines, quinazolines, bisquinazolines and the like can be mentioned.
These compounds are illustrated 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-Diphenylaminofluoran,
3,6-dimethoxyfluoran,
3,6-di-n-butoxyfluoran,
2-Methyl-6- (N-ethyl-Np-tolylamino) fluoran,
3-chloro-6-cyclohexylaminofluoran,
2-Methyl-6-cyclohexylaminofluoran,
2- (2-chloroamino) -6-dibutylaminofluoran,
2- (2-chloroanilino) -6-di-n-butylaminofluoran,
2- (3-Trifluoromethylanilino) -6-diethylaminofluoran,
2- (N-methylanilino) -6- (N-ethyl-Np-tolylamino) fluoran,
1,3-Dimethyl-6-diethylaminofluoran,
2-chloro-3-methyl-6-diethylaminofluoran,
2-anilino-3-methyl-6-diethylaminofluoran,
2-anilino-3-methoxy-6-diethylaminofluoran,
2-anilino-3-methyl-6-di-n-butylaminofluoran,
2-anilino-3-methoxy-6-di-n-butylaminofluoran,
2-xylidino-3-methyl-6-diethylaminofluoran,
1,2-Benz-6-diethylaminofluoran,
1,2-Benz-6- (N-ethyl-N-isobutylamino) fluoran,
1,2-Benz-6- (N-ethyl-N-isoamylamino) fluoran,
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-g) pyrimidin-5,1 '(3'H) isobenzofuran] -3-one;
2- (di-n-butylamino) -8- (di-n-butylamino) -4-methyl-spiro [5H- (1) benzopyrano (2,3-g) pyrimidine-5,1 '(3') H) Isobenzofuran] -3-one,
2- (di-n-butylamino) -8- (diethylamino) -4-methyl-spiro [5H- (1) benzopyrano (2,3-g) pyrimidine-5,1 '(3'H) isobenzofuran] -3- on,
2- (di-n-butylamino) -8- (N-ethyl-N-i-amylamino) -4-methyl-spiro [5H- (1) benzopyrano (2,3-g) pyrimidine-5,1 '(3'H) Isobenzofuran] -3-one,
2- (dibutylamino) -8- (dipentylamino) -4-methyl-spiro [5H- (1) benzopyrano (2,3-g) pyrimidine-5,1 '(3'H) -isobenzofuran] -3 -On,
3- (2-methoxy-4-dimethylaminophenyl) -3- (1-butyl-2-methylindol-3-yl) -4,5,6,7-tetrachlorophthalide,
3- (2-Ethoxy-4-diethylaminophenyl) -3- (1-ethyl-2-methylindol-3-yl) -4,5,6,7-tetrachlorophthalide,
3- (2-Ethoxy-4-diethylaminophenyl) -3- (1-pentyl-2-methylindol-3-yl) -4,5,6,7-tetrachlorophthalide,
4,5,6,7-Tetrachloro-3- [4- (dimethylamino) -2-methylphenyl] -3- (1-ethyl-2-methyl-1H-indol-3-yl) -1 (3H )-Isobenzofuranone,
3 ', 6'-bis [phenyl (2-methylphenyl) amino] -spiro [isobenzofuran-1 (3H), 9'-[9H] xanthene] -3-one,
3 ', 6'-bis [phenyl (3-methylphenyl) amino] -spiro [isobenzofuran-1 (3H), 9'-[9H] xanthene] -3-one,
3 ', 6'-bis [phenyl (3-ethylphenyl) amino] -spiro [isobenzofuran-1 (3H), 9'-[9H] xanthene] -3-one,
4- [2,6-bis (2-ethoxyphenyl) -4-pyridinyl] -N, N-dimethylbenzenamine,
2- (4'-dimethylaminophenyl) -4-methoxy-quinazoline,
4,4 '-(ethylenedioxy) -bis [2- (4-diethylaminophenyl) quinazoline] etc. can be mentioned.
As the fluorans, in addition to the above-mentioned compounds having a substituent in the phenyl group forming the xanthene ring, the substituents also in the phenyl group forming the xanthene ring and the lactone ring (for example Or a compound exhibiting a blue color or a black color having an alkyl group such as a methyl group, or a halogen atom such as a chloro group.
前記（ロ）電子受容性化合物としては、一般式（１）で示されるヒドロキシ安息香酸エステルが用いられる。
前記ヒドロキシ安息香酸エステルのアルキル基は、炭素数が１０〜２２の直鎖又は側鎖アルキル基である。炭素数が１０未満或いは２２を越えるアルキル基を有する系では結晶性が低いため実用性を満足させない。変色特性、発色濃度等、より実用性能を考慮した場合、該化合物のアルキル基は、炭素数１２〜２０の直鎖アルキル基であることが更に好ましい。
以下にヒドロキシ安息香酸エステルを例示する。
３−ヒドロキシ安息香酸デシルエステル、３−ヒドロキシ安息香酸ウンデシルエステル、
３−ヒドロキシ安息香酸ドデシルエステル、３−ヒドロキシ安息香酸トリデシルエステル、３−ヒドロキシ安息香酸テトラデシルエステル、３−ヒドロキシ安息香酸ペンタデシルエステル、３−ヒドロキシ安息香酸ヘキサデシルエステル、３−ヒドロキシ安息香酸ヘプタデシルエステル、３−ヒドロキシ安息香酸オクタデシルエステル、３−ヒドロキシ安息香酸ノナデシルエステル、３−ヒドロキシ安息香酸エイコシルエステル、３−ヒドロキシ安息香酸ヘンエイコシルエステル、３−ヒドロキシ安息香酸ドコシルエステル、４−ヒドロキシ安息香酸デシルエステル、４−ヒドロキシ安息香酸ウンデシルエステル、４−ヒドロキシ安息香酸ドデシルエステル、４−ヒドロキシ安息香酸トリデシルエステル、４−ヒドロキシ安息香酸テトラデシルエステル、４−ヒドロキシ安息香酸ペンタデシルエステル、４−ヒドロキシ安息香酸ヘキサデシルエステル、４−ヒドロキシ安息香酸ヘプタデシルエステル、４−ヒドロキシ安息香酸オクタデシルエステル、４−ヒドロキシ安息香酸ノナデシルエステル、４−ヒドロキシ安息香酸エイコシルエステル、４−ヒドロキシ安息香酸ヘンエイコシルエステル、４−ヒドロキシ安息香酸ドコシルエステル、３，４−ジヒドロキシ安息香酸デシルエステル、３，４−ジヒドロキシ安息香酸ウンデシルエステル、３，４−ジヒドロキシ安息香酸ドデシルエステル、３，４−ジヒドロキシ安息香酸トリデシルエステル、３，４−ジヒドロキシ安息香酸テトラデシルエステル、３，４−ジヒドロキシ安息香酸ペンタデシルエステル、３，４−ジヒドロキシ安息香酸ヘキサデシルエステル、３，４−ジヒドロキシ安息香酸ヘプタデシルエステル、３，４−ジヒドロキシ安息香酸オクタデシルエステル、３，４−ジヒドロキシ安息香酸ノナデシルエステル、３，４−ジヒドロキシ安息香酸エイコシルエステル、３，４−ジヒドロキシ安息香酸ヘンエイコシルエステル、３，４−ジヒドロキシ安息香酸ドコシルエステル、３，５−ジヒドロキシ安息香酸デシルエステル、３，５−ジヒドロキシ安息香酸ウンデシルエステル、３，５−ジヒドロキシ安息香酸ドデシルエステル、３，５−ジヒドロキシ安息香酸トリデシルエステル、３，５−ジヒドロキシ安息香酸テトラデシルエステル、３，５−ジヒドロキシ安息香酸ペンタデシルエステル、３，５−ジヒドロキシ安息香酸ヘキサデシルエステル、３，５−ジヒドロキシ安息香酸ヘプタデシルエステル、３，５−ジヒドロキシ安息香酸オクタデシルエステル、３，５−ジヒドロキシ安息香酸ノナデシルエステル、３，５−ジヒドロキシ安息香酸エイコシルエステル、３，５−ジヒドロキシ安息香酸ヘンエイコシルエステル、３，５−ジヒドロキシ安息香酸ドコシルエステル。
また、前記一般式（１）で示されるヒドロキシ安息香酸エステルと、一般式（４）で示されるヒドロキシフェニル酢酸エステル化合物を併用することもできる。
前記ヒドロキシフェニル酢酸エステル化合物のアルキル基は、炭素数が１０〜２０の直鎖又は側鎖アルキル基である。炭素数が１０未満或いは２０を越えるアルキル基を有する系では結晶性が低いため実用性を満足させない。また、変色特性や発色濃度に優れる等、実用性能を考慮すると炭素数１２〜２０の直鎖アルキル基であることが好ましい。
前記ヒドロキシフェニル酢酸エステル化合物としては、４−ヒドロキシフェニル酢酸デシル、４−ヒドロキシフェニル酢酸ウンデシル、４−ヒドロキシフェニル酢酸ドデシル、４−ヒドロキシフェニル酢酸トリデシル、４−ヒドロキシフェニル酢酸テトラデシル、４−ヒドロキシフェニル酢酸ペンタデシル、４−ヒドロキシフェニル酢酸ヘキサデシル、４−ヒドロキシフェニル酢酸ヘプタデシル、４−ヒドロキシフェニル酢酸オクタデシル、４−ヒドロキシフェニル酢酸ノナデシル、４−ヒドロキシフェニル酢酸エイコシル、４−ヒドロキシフェニル酢酸ヘンエイコシル、４−ヒドロキシフェニル酢酸ドコシルが挙げられる。
As the (ii) electron accepting compound, a hydroxybenzoic acid ester represented by the general formula (1) is used.
The alkyl group of the hydroxybenzoic acid ester is a linear or branched alkyl group having 10 to 22 carbon atoms. A system having an alkyl group having less than 10 carbon atoms or more than 22 carbon atoms does not satisfy practicality because of low crystallinity. In consideration of practical properties such as color-change characteristics, color density and the like, the alkyl group of the compound is more preferably a linear alkyl group having 12 to 20 carbon atoms.
The hydroxybenzoic acid ester is illustrated below.
3-hydroxybenzoic acid decyl ester, 3-hydroxybenzoic acid undecyl ester,
3-hydroxybenzoic acid dodecyl ester, 3-hydroxybenzoic acid tridecyl ester, 3-hydroxybenzoic acid tetradecyl ester, 3-hydroxybenzoic acid pentadecyl ester, 3-hydroxybenzoic acid hexadecyl ester, 3-hydroxybenzoic acid hepta Decyl ester, 3-hydroxybenzoic acid octadecyl ester, 3-hydroxybenzoic acid nonadecyl ester, 3-hydroxybenzoic acid eicosyl ester, 3-hydroxybenzoic acid helicosyl ester, 3-hydroxybenzoic acid docosyl ester, 4- Hydroxybenzoic acid decyl ester, 4-hydroxybenzoic acid undecyl ester, 4-hydroxybenzoic acid dodecyl ester, 4-hydroxybenzoic acid tridecyl ester, 4-hydroxybenzoic acid tetradecyl Ester, 4-hydroxybenzoic acid pentadecyl ester, 4-hydroxybenzoic acid hexadecyl ester, 4-hydroxybenzoic acid heptadecyl ester, 4-hydroxybenzoic acid octadecyl ester, 4-hydroxybenzoic acid nonadecyl ester, 4-hydroxybenzoic acid Acid eicosyl ester, 4-hydroxybenzoic acid helicosyl ester, 4-hydroxybenzoic acid docosyl ester, 3,4-dihydroxybenzoic acid decyl ester, 3,4-dihydroxybenzoic acid undecyl ester, 3,4-dihydroxy Benzoic acid dodecyl ester, 3,4-dihydroxybenzoic acid tridecyl ester, 3,4-dihydroxybenzoic acid tetradecyl ester, 3,4-dihydroxybenzoic acid pentadecyl ester, 3,4-dihydroxy anhydride Aromatic acid hexadecyl ester, 3,4-dihydroxybenzoic acid heptadecyl ester, 3,4-dihydroxybenzoic acid octadecyl ester, 3,4-dihydroxybenzoic acid nonadecyl ester, 3,4-dihydroxybenzoic acid eicosyl ester, 3 , 4-Dihydroxybenzoic acid Heneicosyl ester, 3,4-Dihydroxybenzoic acid docosyl ester, 3,5-dihydroxybenzoic acid decyl ester, 3,5-dihydroxybenzoic acid undecyl ester, 3,5-dihydroxybenzoic acid Dodecyl ester, 3,5-dihydroxybenzoic acid tridecyl ester, 3,5-dihydroxybenzoic acid tetradecyl ester, 3,5-dihydroxybenzoic acid pentadecyl ester, 3,5-dihydroxybenzoic acid hexadecyl ester, 3,5 - Hydroxybenzoic acid heptadecyl ester, 3,5-dihydroxybenzoic acid octadecyl ester, 3,5-dihydroxybenzoic acid nonadecyl ester, 3,5-dihydroxybenzoic acid eicosyl ester, 3,5-dihydroxybenzoic acid hehenicosyl ester , 3,5-dihydroxybenzoic acid docosyl ester.
Further, the hydroxybenzoic acid ester represented by the general formula (1) and the hydroxyphenylacetic acid ester compound represented by the general formula (4) can be used in combination.
The alkyl group of the hydroxyphenyl acetic acid ester compound is a linear or branched alkyl group having 10 to 20 carbon atoms. A system having an alkyl group having less than 10 carbon atoms or more than 20 carbon atoms has low crystallinity and thus is not practical. Further, in consideration of practical performance such as excellent color-change characteristics and coloring density, it is preferably a linear alkyl group having 12 to 20 carbon atoms.
Examples of the hydroxyphenylacetic acid ester compounds include decyl 4-hydroxyphenylacetate, undecyl 4-hydroxyphenylacetate, dodecyl 4-hydroxyphenylacetate, tridecyl 4-hydroxyphenylacetate, tetradecyl 4-hydroxyphenylacetate, pentadecyl 4-hydroxyphenylacetate 4-hydroxyphenylacetic acid hexadecyl, 4-hydroxyphenylacetic acid heptadecyl, 4-hydroxyphenylacetic acid octadecyl, 4-hydroxyphenylacetic acid nonadecyl, 4-hydroxyphenylacetic acid eicosyl, 4-hydroxyphenylacetic acid heheikosyl, 4-hydroxyphenylacetic acid docosyl It can be mentioned.
（ハ）前記（イ）、（ロ）による電子授受反応を可逆的に生起させる反応媒体としては、鎖式炭化水素類、脂環族炭化水素類、芳香族炭化水素類、ハロゲン化炭化水素類から選ばれる化合物が用いられる。
前記化合物を用いることにより、（イ）成分と（ロ）成分の反応による発色性に対する減感性が小さく、加熱発色の変色挙動と色濃度の向上に効果的に機能する。
なお、前記（ロ）成分のヒドロキシ安息香酸エステルはアルキル基の炭素数が大きい程、結晶性が高い傾向にあり、（ハ）成分の添加により結晶性の高いヒドロキシ安息香酸エステルを低温領域の変色温度で使用可能となる。
前記炭化水素類としては、ペンタデカン、ヘキサデカン、ヘプタデカン、オクタデカン、ノナデカン、エイコサン、ヘンエイコサン、ドコサン、トリコサン、テトラコサン、ペンタコサン、ヘキサコサン、ヘプタコサン、オクタコサン、ノナコサン、トリアコンタン等の飽和炭化水素類、１−ペンタデセン、１−ヘキサデセン、１−ヘプタデセン、１−オクタデセン、１−ノナデセン、１−エイコセン、１−ヘンエイコセン、１−ドコセン、１−トリコセン、１−テトラコセン、１−ペンタコセン、１−ヘキサコセン、１−ヘプタコセン、１−オクタコセン、１−ノナコセン、１−トリアコンテン等の不飽和鎖式炭化水素類を例示できる。
脂環式炭化水素類としては、シクロオクタン、シクロドデカン、ｎ−ペンタデシルシクロヘキサン、ｎ−オクタデシルシクロヘキサン、ｎ−ノナデシルシクロヘキサン、デカヒドロナフタレン等を例示できる。
芳香族炭化水素類としては、ドデシルベンゼン、ビフェニル、エチルビフェニル、４−ベンジルベンゼン、フェニルトリルメタン、ジフェニルエタン、１，３−ジフェニルベンゼン、ジベンジルトルエン、メチルナフタレン、２，７−ジイソプロピルナフタレン、メチルテトラリン、ナフチルフェニルメタン等を例示できる。
ハロゲン化炭化水素類としては、１−ブロモデカン、１−ブロモウンデカン、１−ブロモドデカン、１−ブロモトリデカン、１−ブロモテトラデカン、１−クロロテトラデカン、１−ブロモペンタデカン、１−ブロモヘキサデカン、１−クロロヘキサデカン、１−ヨードヘキサデカン、１−ブロモヘプタデカン、１−ブロモオクタデカン、１−クロロオクタデカン、１−ヨードオクタデカン、１−ブロモエイコサン、１−クロロエイコサン、１−ブロモドコサン、１−クロロドコサン等を例示できる。
(C) As a reaction medium for causing the electron transfer reaction reversibly by the (A) and (B), chain hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons The compound selected from is used.
By using the above-mentioned compound, the desensitizing property to the coloration by the reaction of the (i) component and the (ii) component is small, and it effectively functions to improve the color change behavior and color density of the heating color formation.
The higher the number of carbon atoms in the alkyl group, the higher the crystallinity of the hydroxybenzoic acid ester of the component (ii), the higher the crystallinity of the hydroxybenzoic acid ester. Available at temperature.
Saturated hydrocarbons such as pentadecane, hexadecane, heptadecane, octadecane, nonadecane, eicosane, hecoicosan, docosan, trichosan, tetracosan, pentacosan, hexacosan, heptacosan, octacosan, nonacosane, triacontan, 1-pentadecene 1-hexadecene, 1-heptadecene, 1-octadecene, 1-nonadecene, 1-eicosene, 1-henicosene, 1-docosene, 1-trichocene, 1-tetracocene, 1-pentacocene, 1-hexacocene, 1-heptacosene, 1- Unsaturated chain hydrocarbons such as octacosene, 1-nonacosene, 1-triaconten and the like can be exemplified.
Examples of alicyclic hydrocarbons include cyclooctane, cyclododecane, n-pentadecylcyclohexane, n-octadecylcyclohexane, n-nonadecylcyclohexane, decahydronaphthalene and the like.
As aromatic hydrocarbons, dodecylbenzene, biphenyl, ethylbiphenyl, 4-benzylbenzene, phenyltolylmethane, diphenylethane, 1,3-diphenylbenzene, dibenzyltoluene, methylnaphthalene, 2,7-diisopropylnaphthalene, methyl Examples thereof include tetralin and naphthylphenylmethane.
As halogenated hydrocarbons, 1-bromodecane, 1-bromoundecane, 1-bromododecane, 1-bromotridecane, 1-bromotetradecane, 1-chlorotetradecane, 1-bromopentadecane, 1-bromohexadecane, 1- Chlorohexadecane, 1-iodohexadecane, 1-bromoheptadecane, 1-bromooctadecane, 1-chlorooctadecane, 1-iodooctadecane, 1-bromoeicosane, 1-chloroeicosane, 1-bromodocosane, 1-chlorodocosane etc. It can be illustrated.
前記（ニ）軟化点が５℃以上、且つ、重量平均分子量が２００乃至１０万のスチレン系化合物を以下に例示する。
前記スチレン系化合物は重量平均分子量が２００乃至６０００ものが好適に用いられる。
なお、重量平均分子量は、ＧＰＣ法（ゲル浸透クロマトグラフ法）により測定する。
前記スチレン系化合物としては、低分子量ポリスチレン、スチレン−α−メチルスチレン系共重合体、α−メチルスチレン重合体、α−メチルスチレンとビニルトルエンの共重合体等が挙げられる。
低分子量ポリスチレンとしては、三洋化成工業（株）製、商品名：ハイマーＳＢ−７５（重量平均分子量２０００）、ハイマーＳＴ−９５（重量平均分子量４０００）等が用いられる。
スチレン−α−メチルスチレン系共重合体としては、理化ハーキュレス（株）製、商品名：ピコラスチックＡ５（重量平均分子量３１７）、ピコラスチックＡ７５（重量平均分子量９１７）等が用いられる。
α−メチルスチレン重合体としては、理化ハーキュレス（株）製、商品名：クリスタレックス３０８５（重量平均分子量６６４）、クリスタレックス３１００（重量平均分子量１０２０）、クリスタレックス１１２０（重量平均分子量２４２０）等が用いられる。
α−メチルスチレンとビニルトルエンの共重合体としては、理化ハーキュレス（株）製、商品名：ピコテックスＬＣ（重量平均分子量９５０）、ピコテックス１００（重量平均分子量１７４０）等が用いられる。
前記スチレン系化合物は単独で用いてもよいし、２種類以上を併用して用いることもできる。
The styrene compounds having a softening point of 5 ° C. or more and a weight average molecular weight of 200 to 100,000 are exemplified below.
The styrene-based compound preferably has a weight average molecular weight of 200 to 6,000.
The weight average molecular weight is measured by the GPC method (gel permeation chromatography method).
Examples of the styrene compound include low molecular weight polystyrene, styrene-α-methylstyrene copolymer, α-methylstyrene polymer, copolymer of α-methylstyrene and vinyl toluene, and the like.
As low molecular weight polystyrene, Sanyo Chemical Industries, Ltd. make, brand name: Hymer SB-75 (weight average molecular weight 2000), Hymer ST-95 (weight average molecular weight 4000) etc. are used.
As the styrene-α-methylstyrene copolymer, trade name: Picolastic A5 (weight average molecular weight 317), Picolastic A75 (weight average molecular weight 917), etc. are used.
As the α-methylstyrene polymer, manufactured by Rika Hercules Co., Ltd., trade name: Christarex 3085 (weight average molecular weight 664), Christarex 3100 (weight average molecular weight 1020), Christarex 1120 (weight average molecular weight 2420), etc. Used.
As a copolymer of α-methylstyrene and vinyltoluene, trade name: Picotex LC (weight average molecular weight 950), Picotex 100 (weight average molecular weight 1740), etc. are used.
The styrenic compounds may be used alone or in combination of two or more.
前記（ホ）成分として一般式（２）又は（３）から選ばれる化合物を添加することにより、消色時の色消えを向上させることができる。
前記一般式（３）で示される化合物としては、下記構造の化合物が挙げられる。
As a compound shown by the said General formula (3), the compound of the following structure is mentioned.
前記（イ）、（ロ）、（ハ）、（ニ）、（ホ）成分の割合は、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１〜２００、好ましくは５〜１００、（ニ）成分０．１〜１０．０、好ましくは０．５〜５．０、（ホ）成分０．１〜５．０、好ましくは０．５〜２．０の範囲である（前記割合はいずれも重量部である）。 The proportions of the components (a), (b), (c), (d) and (e) depend on the concentration, the color change temperature, the color change form and the type of each component, but generally the desired properties The component ratio obtained is (b) component 0.1 to 50, preferably 0.5 to 20, and (c) component 1 to 200, preferably 5 to 100, with respect to component (1). Component 0.1 to 10.0, preferably 0.5 to 5.0, (e) Component 0.1 to 5.0, preferably 0.5 to 2.0 (all of the above ratios are Parts by weight).
前記可逆熱変色性組成物はマイクロカプセルに内包して使用される。それは、酸性物質、塩基性物質、過酸化物等の化学的に活性な物質又は他の溶剤成分と接触しても、その機能を低下させることがないことは勿論、耐熱安定性が保持できるためであり、種々の使用条件において可逆熱変色性組成物は同一の組成に保たれ、同一の作用効果を奏することができるからである。
なお、マイクロカプセル化は、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。
前記可逆熱変色性マイクロカプセル顔料は、粒子径０．１〜１００μｍ、好ましくは３〜３０μｍの範囲が実用性を満たす。
なお、粒子径の測定はレーザ回折／散乱式粒子径分布測定装置〔（株）堀場製作所製；ＬＡ−３００〕を用いて測定し、その数値を基に平均粒子径（メジアン径）を体積基準で算出する。
The reversible thermochromic composition is used by being enclosed in microcapsules. Even if it comes in contact with chemically active substances such as acidic substances, basic substances, peroxides, etc. or other solvent components, of course, its function is not degraded and heat stability can be maintained. The reversibly thermochromic composition can be maintained at the same composition under various conditions of use and can exhibit the same effect.
Microcapsulation can be performed by 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, melting dispersion cooling method, air suspension coating method And spray-drying methods, etc., which are appropriately selected according to the application. Furthermore, depending on the purpose, a secondary resin film may be further provided on the surface of the microcapsule to impart durability, or the surface characteristics may be modified to be put to practical use.
The reversible thermochromic microcapsule pigment has a particle diameter of 0.1 to 100 [mu] m, preferably 3 to 30 [mu] m.
The particle diameter is measured using a laser diffraction / scattering particle diameter distribution measuring apparatus (manufactured by Horiba, Ltd .; LA-300), and the average particle diameter (median diameter) is based on the volume based on the numerical value. Calculated by
前記各（イ）、（ロ）、（ハ）、（ニ）、（ホ）成分は各々二種以上の化合物の混合であってもよく、更には機能に支障のない範囲で光安定剤を添加することができる。
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、可視光線吸収剤、赤外線吸収剤、酸化防止剤、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、酸化反応を抑制する化合物が挙げられ、０．３〜２４重量％、好ましくは０．８〜１６重量％の割合で系中に配合される。なかでも、前記紫外線吸収剤と、酸化防止剤及び／又は一重項酸素消光剤を併用した系にあっては、耐光性の向上に特に効果的である。
又、老化防止剤、帯電防止剤、極性付与剤、揺変性付与剤、消泡剤等を必要に応じて添加して機能を向上させることもできる。
更には、非熱変色性の一般染料や顔料を配合することもできる。
Each of the components (a), (b), (c), (d) and (e) may be a mixture of two or more compounds, and a light stabilizer may be added to the extent that there is no problem with the function. It can be added.
Examples of the light stabilizer include UV absorbers, visible light absorbers, infrared absorbers, antioxidants, carotenes, dyes, amines, and the like that prevent photodegradation caused by the excited state of the component (i). Singlet oxygen quenchers such as phenols, nickel complexes, sulfides, etc., superoxide anion quenchers such as complexes of oxide dismutase with cobalt and nickel, ozone quenchers, etc., compounds that inhibit oxidation reaction 0.3 to 24% by weight, preferably 0.8 to 16% by weight. Among them, in the system in which the ultraviolet light absorber and the antioxidant and / or the singlet oxygen quencher are used in combination, it is particularly effective to improve the light resistance.
In addition, an antiaging agent, an antistatic agent, a polarity imparting agent, a thixotropy imparting agent, an antifoaming agent, and the like can be added as needed to improve the function.
Furthermore, non-thermochromic general dyes and pigments can also be blended.
前記（イ）、（ロ）、（ハ）、（ニ）、（ホ）成分よりなる可逆熱変色性組成物を内包した可逆熱変色性マイクロカプセル顔料の変色特性を説明する。
消色状態を呈する可逆熱変色性組成物は、加熱過程において発色開始温度（Ｔ１）の温度より発色し始め、完全発色温度（Ｔ２）に達すると完全発色状態となり、降温する過程で消色誘発温度迄冷却した可逆熱変色性組成物は放置すると消色する。
The discoloring characteristics of the reversibly thermochromic microcapsule pigment encapsulating the reversibly thermochromic composition comprising the components (A), (B), (C), (D) and (E) will be described.
The reversible thermochromic composition exhibiting a decolored state starts to develop color from the temperature of color development initiation temperature (T 1 ) in the heating process, becomes fully colored when it reaches the fully colored temperature (T 2 ), and disappears in the process of temperature decrease. The reversibly thermochromic composition cooled to the color-induced temperature until the color fades upon standing.
前記可逆熱変色性マイクロカプセル顔料は、膜形成材料であるバインダーを含む媒体中に分散されて、インキ、塗料などの可逆熱変色性材料として適用され、従来より公知の方法、例えば、スクリーン印刷、オフセット印刷、グラビヤ印刷、コーター、タンポ印刷、転写等の印刷手段、刷毛塗り、スプレー塗装、静電塗装、電着塗装、流し塗り、ローラー塗り、浸漬塗装、等の手段により、紙、合成紙、布帛、植毛或いは起毛布、不織布、合成皮革、レザー、プラスチック、ガラス、陶磁器、木材、石材等の支持体上に可逆熱変色層を形成したり、或いは支持体中に分散することができる。
更には、溶融状態の熱可塑性プラスチック中に混練して一体化された材料として適用できる。
The reversibly thermochromic microcapsule pigment is dispersed in a medium containing a binder which is a film forming material, and is applied as a reversibly thermochromic material such as an ink, a paint, etc., and conventionally known methods such as screen printing, Paper, synthetic paper, by means of offset printing, gravure printing, coater, printing, such as transfer, printing, brush coating, spray coating, electrostatic coating, electrodeposition coating, flow coating, roller coating, dip coating, etc. The reversibly thermochromic layer can be formed on or dispersed in a support such as fabric, flocked or raised, nonwoven fabric, synthetic leather, leather, plastic, glass, china, wood, stone and the like.
Furthermore, it is possible to knead it in a molten thermoplastic resin and apply it as an integrated material.
本発明の可逆熱変色性組成物に用いられる組成を以下の表に示す。
なお、表中の（ ）内の数字は質量部を示し、以下の配合量を示す数字はいずれも質量部である。
The compositions used for the reversible thermochromic composition of the present invention are shown in the following table.
In addition, the number in () of a table | surface shows a mass part, and all the numbers which show the following compounding quantities are mass parts.
表中の（ニ）成分について、ピコラスチックＡ−７５は、低分子量ポリスチレン樹脂、軟化点７５℃であり、ピコラスチックＤ−１２５は、低分子量ポリスチレン樹脂、軟化点１２５℃である。
表中の（ホ）成分について、化合物Ａは一般式（２）で示される化合物であり、化合物１、５、７、９は表に示される一般式（３）で示される化合物である。
With regard to the component (d) in the table, picolastic A-75 is a low molecular weight polystyrene resin, with a softening point of 75 ° C, and picolastic D-125 is a low molecular weight polystyrene resin, with a softening point of 125 ° C.
As for the component (e) in the table, the compound A is a compound represented by the general formula (2), and the compounds 1, 5, 7 and 9 are compounds represented by the general formula (3) shown in the table.
各可逆熱変色性組成物を加温溶融して相溶体とした後、エポキシ樹脂及びアミン硬化剤による界面重合反応によりエポキシ樹脂皮膜で内包されたマイクロカプセル形態の可逆熱変色性マイクロカプセル顔料を得た。
前記可逆熱変色性マイクロカプセル顔料について、以下の測定試料を作成した後、以下の測定方法により変色温度を測定した。
After each reversible thermochromic composition is heated and melted to form a compatible substance, a reversible thermochromic microcapsule pigment encapsulated in an epoxy resin film is obtained by interfacial polymerization reaction with an epoxy resin and an amine curing agent. The
The following measurement samples were prepared for the reversibly thermochromic microcapsule pigment, and then the color change temperature was measured by the following measurement method.
測定試料
前記可逆熱変色性マイクロカプセル顔料４０部をエチレン−酢酸ビニルエマルジョン中に分散してなる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印刷した印刷物を測定試料とした。
Measurement sample A printed matter printed on wood free paper by screen printing was used as a measurement sample, using a reversibly thermochromic ink prepared by dispersing 40 parts of the reversibly thermochromic microcapsule pigment in an ethylene-vinyl acetate emulsion.
測定方法
実施例１乃至８の測定試料を色差計〔ＴＣ−３６００型色差計、（株）東京電色製〕の所定箇所にセットし、０℃から６０℃の温度幅で速度１０℃／分にて加熱する。
６０℃迄加熱した後、消色誘発温度（−１０℃）迄冷却し、放置して消色させた
実施例９及び１０の測定試料を色差計〔ＴＣ−３６００型色差計、（株）東京電色製〕の所定箇所にセットし、０℃から６０℃の温度幅で速度１０℃／分にて加熱する。
６０℃迄加熱した後、消色誘発温度（５℃）迄冷却し、放置して消色させた。
各実施例の色変化、発色開始温度（Ｔ１）、完全発色温度（Ｔ２）、消色誘発温度、消色誘発温度迄冷却して消色するのに要した時間を以下の表に示す。
Measurement method The measurement samples of Examples 1 to 8 are set at predetermined positions of a color difference meter (TC-3600 color difference meter, manufactured by Tokyo Denshoku Co., Ltd.), and the temperature range of 0 ° C. to 60 ° C. is 10 ° C./min. Heat at.
The sample was heated to 60 ° C., cooled to the decoloring induction temperature (−10 ° C.), allowed to stand and decolorized The color difference meter [TC-3600 type color difference meter, Tokyo Co., Ltd. It is set at a predetermined position of [made by electric color], and heated at a speed of 10 ° C./minute at a temperature range of 0 ° C. to 60 ° C.
After heating to 60 ° C., it was cooled to the decoloring induction temperature (5 ° C.) and left to decolorize.
The color change, color development start temperature (T 1 ), complete color development temperature (T 2 ), decoloration induction temperature, decoloration induction temperature of each example are shown in the following table for the time required for decoloration by cooling. .
応用例１
実施例１で作製した可逆熱変色性組成物を内包したマイクロカプセル顔料３０．０部、蛍光顔料（ピンク色）２．０部、アクリル樹脂エマルジョン５０．０部、消泡剤３．０部、ターペンエマルジョン１５．０部からなる可逆熱変色性スクリーンインキを調製した。
ポリエステルタフタに前記可逆熱変色性スクリーンインキを用いてスクリーン印刷により印刷し、可逆熱変色層を形成して可逆熱変色性シートを得た。
前記可逆熱変色性シートは４３℃以上に加温すると紫色を呈する。
前記可逆熱変色性シートを０℃の冷凍庫に３０分以上冷却する。その後冷凍庫から取り出すと前記可逆熱変色性シートはピンク色を呈する。
Application Example 1
30.0 parts of a microcapsule pigment containing the reversible thermochromic composition prepared in Example 1, 2.0 parts of a fluorescent pigment (pink), 50.0 parts of an acrylic resin emulsion, 3.0 parts of an antifoamer, A reversibly thermochromic screen ink consisting of 15.0 parts of a tarpen emulsion was prepared.
It printed by screen printing using the said reversible thermochromic screen ink on the polyester taffeta, and formed the reversible thermochromic layer, and obtained the reversible thermochromic sheet.
The reversible thermochromic sheet exhibits a purple color when heated to 43 ° C. or higher.
The reversible thermochromic sheet is cooled in a freezer at 0 ° C. for 30 minutes or more. Thereafter, when it is removed from the freezer, the reversible thermochromic sheet exhibits a pink color.
応用例２
実施例１０で作製した可逆熱変色性組成物を内包したマイクロカプセル顔料５０．０部を、アマニ油系オフセットインキビヒクル５０．０部中に均一に分散混合して、可逆熱変色性オフセットインキを調製した。
上質紙に前記オフセットインキを用いてオフセット印刷を行ない、可逆熱変色層を形成して可逆熱変色性シートを得た。
前記シートは５４℃以上に加温すると桃色を呈する。
前記可逆熱変色性シートを５℃の冷蔵庫で３０分以上冷却する。その後冷蔵庫から取り出して放置すると前記可逆熱変色性シートは無色を呈する。
Application example 2
50.0 parts of the microcapsule pigment encapsulating the reversible thermochromic composition prepared in Example 10 is uniformly dispersed and mixed in 50.0 parts of linseed oil-based offset ink vehicle to obtain a reversible thermochromic offset ink Prepared.
Offset printing was performed on wood free paper using the above-mentioned offset ink to form a reversible thermochromic layer to obtain a reversible thermochromic sheet.
The sheet exhibits a pink color when heated to 54 ° C. or higher.
The reversible thermochromic sheet is cooled in a refrigerator at 5 ° C. for 30 minutes or more. Thereafter, when it is taken out of the refrigerator and left to stand, the reversible thermochromic sheet becomes colorless.
応用例３
実施例７で作製した可逆熱変色性組成物を内包したマイクロカプセル顔料１０．０部、一般顔料（青色）１．０部、５０％アクリル樹脂／キシレン溶液４５．０部、キシレン１５．０部、メチルイソブチルケトン２３．０部、ポリイソシアネート系硬化剤６．０部からなるビヒクル中に攪拌混合して可逆熱変色性スプレー塗料を調製した。
ミニチュア電車全体に前記可逆熱変色性スプレー塗料をスプレー塗装して可逆熱変色層を形成して可逆熱変色性ミニチュア電車を得た。
前記可逆熱変色性ミニチュア電車は４２℃以上に加温すると紫色を呈する。
前記可逆熱変色性ミニチュア電車を０℃の冷凍庫で３０分以上冷却する。その後冷凍庫から取り出して放置すると前記可逆熱変色性ミニチュア電車は青色を呈する。
Application example 3
10.0 parts of a microcapsule pigment encapsulating the reversible thermochromic composition prepared in Example 7, 1.0 part of a general pigment (blue), 45.0 parts of a 50% acrylic resin / xylene solution, 15.0 parts of xylene A reversible thermochromic spray paint was prepared by stirring and mixing in a vehicle consisting of 23.0 parts of methyl isobutyl ketone and 6.0 parts of a polyisocyanate-based curing agent.
The reversible thermochromic spray paint was spray coated on the entire miniature train to form a reversible thermochromic layer to obtain a reversible thermochromic miniature train.
The reversible thermochromic miniature train exhibits a purple color when heated to 42 ° C. or higher.
The reversible thermochromic miniature train is cooled in a 0 ° C. freezer for at least 30 minutes. The reversible thermochromic miniature train then exhibits a blue color when removed from the freezer and left to stand.
応用例４
実施例９で作製した可逆熱変色性組成物を内包したマイクロカプセル顔料３３．３部、硬質タイプの液状エポキシ樹脂６６．４部、消泡剤０．３部を均一に分散練合させて得られた可逆熱変色性エポキシインキ中に常温硬化型の脂肪族ポリアミド２０．０部を添加し、攪拌混合して可逆熱変色性エポキシインキを調製した。
陶磁器製カップ表面に前記可逆熱変色性エポキシインキを用いてステンレススチール製１００メッシュスクリーン版にて曲面スクリーン印刷を行ない、７０℃で６０分間、加熱硬化して可逆熱変色層を形成して可逆熱変色性カップを得た。
前記可逆熱変色性カップは４９℃以上に加温すると青色を呈する。
前記可逆熱変色性カップを５℃の冷凍庫で３０分以上冷却する。その後冷凍庫から取りて放置すると前記可逆熱変色性カップは無色を呈する。
Application 4
Obtained by uniformly dispersing and kneading 33.3 parts of the microcapsule pigment encapsulating the reversible thermochromic composition prepared in Example 9, 66.4 parts of a hard type liquid epoxy resin, and 0.3 parts of an antifoaming agent. In the above reversible thermochromic epoxy ink, 20.0 parts of a room temperature curing type aliphatic polyamide was added and mixed by stirring to prepare a reversible thermochromic epoxy ink.
Curved screen printing is performed with a stainless steel 100 mesh screen plate using the above-mentioned reversible thermochromic epoxy ink on the surface of a ceramic cup, and heat curing is carried out at 70 ° C. for 60 minutes to form a reversible thermochromic layer and reversible heat A discolored cup was obtained.
The reversibly thermochromic cup exhibits a blue color when heated to 49 ° C. or higher.
The reversible thermochromic cup is cooled for 30 minutes or more in a 5 ° C. freezer. The reversible thermochromic cup then becomes colorless when taken out of the freezer and left to stand.
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