JP7443335B2 - Reversible thermochromic microcapsule pigment - Google Patents
Reversible thermochromic microcapsule pigment Download PDFInfo
- Publication number
- JP7443335B2 JP7443335B2 JP2021509112A JP2021509112A JP7443335B2 JP 7443335 B2 JP7443335 B2 JP 7443335B2 JP 2021509112 A JP2021509112 A JP 2021509112A JP 2021509112 A JP2021509112 A JP 2021509112A JP 7443335 B2 JP7443335 B2 JP 7443335B2
- Authority
- JP
- Japan
- Prior art keywords
- reversible thermochromic
- microcapsule pigment
- pigment according
- compound
- color
- 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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- 239000002562 thickening agent Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- MCJUNPPODVYJBD-UHFFFAOYSA-N triacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO MCJUNPPODVYJBD-UHFFFAOYSA-N 0.000 description 1
- OLTHARGIAFTREU-UHFFFAOYSA-N triacontane Natural products CCCCCCCCCCCCCCCCCCCCC(C)CCCCCCCC OLTHARGIAFTREU-UHFFFAOYSA-N 0.000 description 1
- REZQBEBOWJAQKS-UHFFFAOYSA-N triacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO REZQBEBOWJAQKS-UHFFFAOYSA-N 0.000 description 1
- VBCBSDJKFLGBIX-UHFFFAOYSA-N tridecyl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCC VBCBSDJKFLGBIX-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 229940113164 trimyristin Drugs 0.000 description 1
- 229960001947 tripalmitin Drugs 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- FKVMWDZRDMCIAJ-UHFFFAOYSA-N undecanamide Chemical compound CCCCCCCCCCC(N)=O FKVMWDZRDMCIAJ-UHFFFAOYSA-N 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- UPIXQYOSHAJORT-UHFFFAOYSA-N undecyl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCC UPIXQYOSHAJORT-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
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/26—Triarylmethane dyes in which at least one of the aromatic nuclei is heterocyclic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/28—Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
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 specifically, the present invention relates to a reversible thermochromic microcapsule pigment that develops color by heating from a decolorized state.
従来、(a)電子供与性呈色性有機化合物、(b)電子受容性化合物、(c)(a)及び(b)成分による電子授受反応を可逆的に生起させる反応媒体を含んでなる可逆熱変色性組成物のうち、(b)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となり、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てなる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)。
これらの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。
Conventionally, a reversible reaction medium comprising (a) an electron-donating color-forming organic compound, (b) an electron-accepting compound, and (c) a reaction medium that reversibly causes an electron-donating reaction between components (a) and (b). Among the thermochromic compositions, by using a hydroxybenzoic acid ester as the component (b), a reversible thermochromic composition exhibits discoloration behavior in which it becomes a colored state by heating from a decolored state and returns to the decolored state by cooling. A compound and a microcapsule pigment containing the same have been disclosed (for example, see Patent Document 1).
Although these reversible thermochromic compositions develop color when heated, the temperature at which the color develops is high, and it has been difficult to easily develop color at or near daily life temperature. Furthermore, even if a reversible thermochromic composition that develops color at or near daily life temperature is obtained, the color density in the developed state is low and does not satisfy practicality.
本発明者は、消色状態からの加熱により発色する可逆熱変色性組成物について鋭意検討した結果、(b)成分として特定のヒドロキシフェニル酢酸エステル化合物を用い、且つ、(d)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となり、再び消色状態に復帰する変色挙動を示すと共に、発色時の色濃度が高い可逆熱変色性組成物を内包してなる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 studies on reversible thermochromic compositions that develop color upon heating from a decolorized state, the present inventors found that a specific hydroxyphenylacetic acid ester compound is used as the component (b), and a specific hydroxyphenylacetic acid ester compound is used as the component (d). By adding a compound, it exhibits discoloration behavior in which it easily changes from a decolorized state to a colored state by heating in the living environment temperature range or at a temperature close to the daily living temperature, and then returns to the decolored state again, and the color density at the time of coloring changes. The present invention was completed based on the discovery that a reversible thermochromic microcapsule pigment containing a reversible thermochromic composition having a high viscosity can be obtained.
本発明による可逆熱変色性マイクロカプセル顔料は、
(a)電子供与性呈色性有機化合物と、
(b)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フェニル酢酸エステル化合物と、
(c)(a)及び(b)成分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、及びハロゲン化炭化水素類からなる群から選ばれる化合物と、
(d)軟化点が5℃以上、且つ、質量平均分子量が200~10万のスチレン系化合物と
を含んでなる可逆熱変色性組成物を内包してなる。
Rは、炭素数12~22の、直鎖又は分岐の、アルキル基を示し、
X、Y、及びZは、それぞれ独立に水素または水酸基であり、それらのうち二つ又は三つが水酸基であり、残りは水素である)
The reversible thermochromic microcapsule pigment according to the present invention comprises:
(a) an electron-donating color-forming organic compound;
(b) a hydroxyphenylacetate compound represented by the following general formula (1) as an electron-accepting compound;
(c) The reaction medium for reversibly causing the electron transfer reaction between components (a) and (b) is selected from the group consisting of chain hydrocarbons, alicyclic hydrocarbons, and halogenated hydrocarbons. compound and
(d) A reversible thermochromic composition containing a styrene compound having a softening point of 5° C. or higher and a mass average molecular weight of 200 to 100,000.
R represents a linear or branched alkyl group having 12 to 22 carbon atoms,
X, Y, and Z are each independently hydrogen or a hydroxyl group, two or three of them are hydroxyl groups, and the rest are hydrogen)
本発明による可逆熱変色性液状組成物は、上記の可逆熱変色性マイクロカプセル顔料と、ビヒクルとを含んでなる。 The reversible thermochromic liquid composition according to the present invention comprises the above-mentioned reversible thermochromic microcapsule pigment and a vehicle.
本発明による積層体は、支持体と、上記のマイクロカプセル顔料とを含んでなる可逆熱変色層とを具備してなる。 The laminate according to the present invention comprises a support and a reversible thermochromic layer containing the above-mentioned microcapsule pigment.
本発明による成形体は、支持体に、上記のマイクロカプセル顔料が含まれている。 In the molded article according to the present invention, the support contains the above-mentioned microcapsule pigment.
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となり、再び消色状態に復帰する可逆的変色挙動を示すと共に、発色時の色濃度が高く、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 reversible discoloration behavior in which it easily changes from a decolored state to a colored state by heating in the living environment temperature range or at a temperature close to daily living temperature, and returns to the decolored state again, and the color density at the time of coloring is It is possible to provide reversible thermochromic microcapsule pigments that are highly expensive and can be applied to various fields such as educational elements, toys, and decorations.
以下に各成分について具体的に化合物を例示する。
本発明の(a)成分、即ち電子供与性呈色性有機化合物は、色を決める成分であって、顕色剤である(b)成分に電子を供与し、発色する化合物である。
電子供与性呈色性有機化合物としては、フタリド化合物、フルオラン化合物、スチリノキノリン化合物、ジアザローダミンラクトン化合物、ピリジン化合物、キナゾリン化合物、ビスキナゾリン化合物等が挙げられ、これらのうちフタリド化合物及びフルオラン化合物が好ましい。
フタリド化合物としては、例えばジフェニルメタンフタリド化合物、フェニルインドリルフタリド化合物、インドリルフタリド化合物、ジフェニルメタンアザフタリド化合物、フェニルインドリルアザフタリド化合物、及びそれらの誘導体などが挙げられ、これらの中でも、フェニルインドリルアザフタリド化合物、ならびにそれらの誘導体が好ましい。
また、フルオラン化合物としては、例えば、アミノフルオラン化合物、アルコキシフルオラン化合物、及びそれらの誘導体が挙げられる。
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-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-アザフタリド、
3-(2-ヘキシルオキシ-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-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-(2-アセトアミド-4-ジエチルアミノフェニル)-3-(1-プロピルインドール-3-イル)-4-アザフタリド、
3,6-ビス(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-(3-トリフルオロメチルアニリノ)-6-ジペンチルアミノフルオラン、
2-(ジベンジルアミノ)-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、
2-アニリノ-3-メチル-6-(N-エチル-N-p-トリルアミノ)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-(ジブチルアミノ)-8-(ジペンチルアミノ)-4-メチル、
4,5,6,7-テトラクロロ-3-〔4-(ジメチルアミノ)-2-メトキシフェニル〕-3-(1-ブチル-2-メチル-1H-インドール-3-イル)-1(3H)-イソベンゾフラノン、
4,5,6,7-テトラクロロ-3-〔4-(ジエチルアミノ)-2-エトキシフェニル〕-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、
4,5,6,7-テトラクロロ-3-〔4-(ジエチルアミノ)-2-エトキシフェニル〕-3-(1-ペンチル-2-メチル-1H-インドール-3-イル)-1(3H)-イソベンゾフラノン、
4,5,6,7-テトラクロロ-3-[4-(ジエチルアミノ)-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、
2,6-ビス(2′-エチルオキシフェニル)-4-(4′-ジメチルアミノフェニル)ピリジン、
2,6-ビス(2′,4′-ジエチルオキシフェニル)-4-(4′-ジメチルアミノフェニル)ピリジン、
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。
Specific examples of compounds for each component are shown below.
The component (a) of the present invention, that is, the electron-donating color-forming organic compound, is a component that determines color, and is a compound that donates electrons to component (b), which is a color developer, to develop color.
Examples of the electron-donating color-forming organic compound include phthalide compounds, fluoran compounds, styrinoquinoline compounds, diazalhodamine lactone compounds, pyridine compounds, quinazoline compounds, bisquinazoline compounds, and among these, phthalide compounds and fluoran compounds are preferred. .
Examples of phthalide compounds include diphenylmethane phthalide compounds, phenylindolylphthalide compounds, indolylphthalide compounds, diphenylmethane azaphthalide compounds, phenylindolyl azaphthalide compounds, and derivatives thereof. , phenylindolyl azaphthalide compounds, and derivatives thereof are preferred.
Furthermore, examples of the fluoran compound include aminofluoran compounds, alkoxyfluoran compounds, and derivatives thereof.
Examples of these compounds are shown 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-diethylaminophenyl)-3-(1-ethyl-2-methylindol-3-yl)-4-azaphthalide,
3-(2-hexyloxy-4-diethylaminophenyl)-3-(1-ethyl-2-methylindol-3-yl)-4-azaphthalide,
3-[2-ethoxy-4-(N-ethylanilino)phenyl]-3-(1-ethyl-2-methylindol-3-yl)-4-azaphthalide,
3-(2-acetamido-4-diethylaminophenyl)-3-(1-propylindol-3-yl)-4-azaphthalide,
3,6-bis(diphenylamino)fluorane,
3,6-dimethoxyfluorane,
3,6-di-n-butoxyfluorane,
2-methyl-6-(N-ethyl-Np-tolylamino)fluoran,
3-chloro-6-cyclohexylaminofluorane,
2-methyl-6-cyclohexylaminofluorane,
2-(2-chloroamino)-6-dibutylaminofluorane,
2-(2-chloroanilino)-6-di-n-butylaminofluorane,
2-(3-trifluoromethylanilino)-6-diethylaminofluorane,
2-(3-trifluoromethylanilino)-6-dipentylaminofluorane,
2-(dibenzylamino)-6-diethylaminofluorane,
2-(N-methylanilino)-6-(N-ethyl-Np-tolylamino)fluoran,
1,3-dimethyl-6-diethylaminofluorane,
2-chloro-3-methyl-6-diethylaminofluorane,
2-anilino-3-methyl-6-diethylaminofluorane,
2-anilino-3-methoxy-6-diethylaminofluorane,
2-anilino-3-methyl-6-di-n-butylaminofluorane,
2-anilino-3-methoxy-6-di-n-butylaminofluorane,
2-xylidino-3-methyl-6-diethylaminofluorane,
2-anilino-3-methyl-6-(N-ethyl-Np-tolylamino)fluoran,
1,2-benz-6-diethylaminofluorane,
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-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-N-i-amylamino)-4-methyl,
Spiro[5H-(1)benzopyrano(2,3-d)pyrimidine-5,1'(3'H)isobenzofuran]-3'-one, 2-(dibutylamino)-8-(dipentylamino)-4 -Methyl,
4,5,6,7-tetrachloro-3-[4-(dimethylamino)-2-methoxyphenyl]-3-(1-butyl-2-methyl-1H-indol-3-yl)-1(3H )-isobenzofuranone,
4,5,6,7-tetrachloro-3-[4-(diethylamino)-2-ethoxyphenyl]-3-(1-ethyl-2-methyl-1H-indol-3-yl)-1(3H) -isobenzofuranone,
4,5,6,7-tetrachloro-3-[4-(diethylamino)-2-ethoxyphenyl]-3-(1-pentyl-2-methyl-1H-indol-3-yl)-1(3H) -isobenzofuranone,
4,5,6,7-tetrachloro-3-[4-(diethylamino)-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,
2,6-bis(2'-ethyloxyphenyl)-4-(4'-dimethylaminophenyl)pyridine,
2,6-bis(2',4'-diethyloxyphenyl)-4-(4'-dimethylaminophenyl)pyridine,
2-(4'-dimethylaminophenyl)-4-methoxy-quinazoline,
4,4'-(ethylenedioxy)-bis[2-(4-diethylaminophenyl)quinazoline]
etc. can be mentioned.
In addition to the above-mentioned compounds having a substituent on the phenyl group forming the xanthene ring, examples of fluoranes include compounds having a substituent on the phenyl group forming the xanthene ring and also substituents on the phenyl group forming the lactone ring (e.g. , an alkyl group such as a methyl group, or a halogen atom such as a chloro group) that exhibits blue or black color.
(b)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フェニル酢酸エステル化合物が用いられる。
Rは、炭素数12~22の、直鎖又は分岐の、アルキル基を示し、
X、Y、及びZは、それぞれ独立に、水素又は水酸基であり、それらのうち二つ又は三つが水酸基であり、
好ましくはX、Y、及びZのうち、二つが水酸基であり、一つが水素である。
更に好ましくはX及びYが水酸基であり、Zが水素である。具体的には、一般式(2)で示される3,4-ジヒドロキシフェニル酢酸エステル化合物が好ましいものであり、これは発色時の色濃度が高いため好適に用いられる。
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12~22の、直鎖又は分岐の、アルキル基、好ましくは炭素数が14~22の、直鎖又は分岐の、アルキル基である。炭素数が12未満或いは22を越えるアルキル基を有する化合物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12~22の直鎖アルキル基であることが好ましく、より好ましくは炭素数16~22の直鎖アルキル基、更に好ましくは16~20の直鎖アルキル基、より更に好ましくは16~18の直鎖アルキル基である。
ヒドロキシフェニル酢酸エステル化合物としては、3,4-ジヒドロキシフェニル酢酸ドデシル、3,4-ジヒドロキシフェニル酢酸トリデシル、3,4-ジヒドロキシフェニル酢酸テトラデシル、3,4-ジヒドロキシフェニル酢酸2-メチルトリデシル、3,4-ジヒドロキシフェニル酢酸ペンタデシル、3,4-ジヒドロキシフェニル酢酸ヘキサデシル、3,4-ジヒドロキシフェニル酢酸2-エチルテトラデシル、3,4-ジヒドロキシフェニル酢酸ヘプタデシル、3,4-ジヒドロキシフェニル酢酸2-メチルヘキサデシル、3,4-ジヒドロキシフェニル酢酸オクタデシル、3,4-ジヒドロキシフェニル酢酸2-メチルヘプチルデシル、3,4-ジヒドロキシフェニル酢酸2-エチルヘキサデシル、3,4-ジヒドロキシフェニル酢酸ノナデシル、3,4-ジヒドロキシフェニル酢酸エイコシル、3,4-ジヒドロキシフェニル酢酸2-メチルノナデシル、3,4-ジヒドロキシフェニル酢酸2-エチルオクタデシル、3,4-ジヒドロキシフェニル酢酸ヘンエイコシル、3,4-ジヒドロキシフェニル酢酸ドコシル、3,5-ジヒドロキシフェニル酢酸ドデシル、3,5-ジヒドロキシフェニル酢酸トリデシル、3,5-ジヒドロキシフェニル酢酸テトラデシル、3,5-ジヒドロキシフェニル酢酸2-メチルトリデシル、3,5-ジヒドロキシフェニル酢酸ペンタデシル、3,5-ジヒドロキシフェニル酢酸ヘキサデシル、3,5-ジヒドロキシフェニル酢酸2-エチルテトラデシル、3,5-ジヒドロキシフェニル酢酸ヘプタデシル、3,5-ジヒドロキシフェニル酢酸2-メチルヘキサデシル、3,5-ジヒドロキシフェニル酢酸オクタデシル、3,5-ジヒドロキシフェニル酢酸2-メチルヘプチルデシル、3,5-ジヒドロキシフェニル酢酸2-エチルヘキサデシル、3,5-ジヒドロキシフェニル酢酸ノナデシル、3,5-ジヒドロキシフェニル酢酸エイコシル、3,5-ジヒドロキシフェニル酢酸2-メチルノナデシル、3,5-ジヒドロキシフェニル酢酸2-エチルオクタデシル、3,5-ジヒドロキシフェニル酢酸ヘンエイコシル、3,5-ジヒドロキシフェニル酢酸ドコシルが挙げられる。更には、さらには、X、Y、およびZのすべてが水酸基であるものとして、3,4,5-トリヒドロキシフェニル酢酸ドデシル、3,4,5-トリヒドロキシフェニル酢酸トリデシル、3,4,5-トリヒドロキシフェニル酢酸テトラデシル、3,4,5-トリヒドロキシフェニル酢酸2-メチルトリデシル、3,4,5-トリヒドロキシフェニル酢酸ペンタデシル、3,4,5-トリヒドロキシフェニル酢酸ヘキサデシル、3,4,5-トリヒドロキシフェニル酢酸2-エチルテトラデシル、3,4,5-トリヒドロキシフェニル酢酸ヘプタデシル、3,4,5-トリヒドロキシフェニル酢酸2-メチルヘキサデシル、3,4,5-トリヒドロキシフェニル酢酸オクタデシル、3,4,5-トリヒドロキシフェニル酢酸2-メチルヘプチルデシル、3,4,5-トリヒドロキシフェニル酢酸2-エチルヘキサデシル、3,4,5-トリヒドロキシフェニル酢酸ノナデシル、3,4,5-トリヒドロキシフェニル酢酸エイコシル、3,4,5-トリヒドロキシフェニル酢酸2-メチルノナデシル、3,4,5-トリヒドロキシフェニル酢酸2-エチルオクタデシル、3,4,5-トリヒドロキシフェニル酢酸ヘンエイコシル、3,4,5-トリヒドロキシフェニル酢酸ドコシルなども用いることができる。一般に水酸基が多い化合物は、発色時の色濃度が高い傾向にある。
(b) As the electron-accepting compound, a hydroxyphenylacetate compound represented by general formula (1) is used.
R represents a linear or branched alkyl group having 12 to 22 carbon atoms,
X, Y, and Z are each independently hydrogen or a hydroxyl group, and two or three of them are hydroxyl groups,
Preferably, two of X, Y, and Z are hydroxyl groups and one is hydrogen.
More preferably, X and Y are hydroxyl groups, and Z is hydrogen. Specifically, a 3,4-dihydroxyphenylacetic acid ester compound represented by the general formula (2) is preferred, and this is suitably used because it has a high color density during color development.
The alkyl group of the hydroxyphenylacetate compound is a straight-chain or branched alkyl group having 12 to 22 carbon atoms, preferably a straight-chain or branched alkyl group having 14 to 22 carbon atoms. Compounds having an alkyl group having less than 12 carbon atoms or more than 22 carbon atoms have low crystallinity and are therefore unsatisfactory for practical use. In addition, in consideration of practical performance such as excellent discoloration properties and color density, linear alkyl groups having 12 to 22 carbon atoms are preferable, more preferably linear alkyl groups having 16 to 22 carbon atoms, and still more preferably 16 to 22 carbon atoms. ~20 straight chain alkyl groups, even more preferably 16 to 18 straight chain alkyl groups.
Examples of hydroxyphenylacetate compounds include dodecyl 3,4-dihydroxyphenylacetate, tridecyl 3,4-dihydroxyphenylacetate, tetradecyl 3,4-dihydroxyphenylacetate, 2-methyltridecyl 3,4-dihydroxyphenylacetate, 3, Pentadecyl 4-dihydroxyphenylacetate, hexadecyl 3,4-dihydroxyphenylacetate, 2-ethyltetradecyl 3,4-dihydroxyphenylacetate, heptadecyl 3,4-dihydroxyphenylacetate, 2-methylhexadecyl 3,4-dihydroxyphenylacetate , 3,4-dihydroxyphenylacetate octadecyl, 3,4-dihydroxyphenylacetate 2-methylheptyldecyl, 3,4-dihydroxyphenylacetate 2-ethylhexadecyl, 3,4-dihydroxyphenylacetate nonadecyl, 3,4-dihydroxy Eicosyl phenylacetate, 2-methylnonadecyl 3,4-dihydroxyphenylacetate, 2-ethyl octadecyl 3,4-dihydroxyphenylacetate, heneicosyl 3,4-dihydroxyphenylacetate, docosyl 3,4-dihydroxyphenylacetate, 3,5-dihydroxy Dodecyl phenylacetate, tridecyl 3,5-dihydroxyphenylacetate, tetradecyl 3,5-dihydroxyphenylacetate, 2-methyltridecyl 3,5-dihydroxyphenylacetate, pentadecyl 3,5-dihydroxyphenylacetate, 3,5-dihydroxyphenyl Hexadecyl acetate, 2-ethyltetradecyl 3,5-dihydroxyphenylacetate, heptadecyl 3,5-dihydroxyphenylacetate, 2-methylhexadecyl 3,5-dihydroxyphenylacetate, octadecyl 3,5-dihydroxyphenylacetate, 3,5 -2-methylheptyldecyl dihydroxyphenylacetate, 2-ethylhexadecyl 3,5-dihydroxyphenylacetate, nonadecyl 3,5-dihydroxyphenylacetate, eicosyl 3,5-dihydroxyphenylacetate, 2-dihydroxyphenylacetate, 3,5-dihydroxyphenylacetate Examples include methylnonadecyl, 2-ethyloctadecyl 3,5-dihydroxyphenylacetate, heneicosyl 3,5-dihydroxyphenylacetate, and docosyl 3,5-dihydroxyphenylacetate. Furthermore, all of X, Y, and Z are hydroxyl groups, such as 3,4,5-trihydroxyphenylacetic acid dodecyl, 3,4,5-trihydroxyphenylacetic acid tridecyl, 3,4,5 -Tetradecyl trihydroxyphenylacetate, 2-methyltridecyl 3,4,5-trihydroxyphenylacetate, pentadecyl 3,4,5-trihydroxyphenylacetate, hexadecyl 3,4,5-trihydroxyphenylacetate, 3,4 , 2-ethyltetradecyl 5-trihydroxyphenylacetate, 3,4,5-heptadecyl trihydroxyphenylacetate, 2-methylhexadecyl 3,4,5-trihydroxyphenylacetate, 3,4,5-trihydroxyphenyl Octadecyl acetate, 2-methylheptyldecyl 3,4,5-trihydroxyphenylacetate, 2-ethylhexadecyl 3,4,5-trihydroxyphenylacetate, nonadecyl 3,4,5-trihydroxyphenylacetate, 3,4 , 5-eicosyl trihydroxyphenylacetate, 2-methylnonadecyl 3,4,5-trihydroxyphenylacetate, 2-ethyl octadecyl 3,4,5-trihydroxyphenylacetate, heneicosyl 3,4,5-trihydroxyphenylacetate, Docosyl 3,4,5-trihydroxyphenylacetate and the like can also be used. In general, compounds with many hydroxyl groups tend to have high color density when developed.
(c)(a)及び(b)成分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、及びハロゲン化炭化水素類からなる群から選ばれる化合物が用いられる。
(c)成分の化合物を用いることにより、(a)成分と(b)成分の反応による発色性に対する減感性が小さく、加熱による発色する変色挙動と色濃度の向上に効果的に機能する。
なお、(b)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、(c)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。
鎖式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鎖式炭化水素類、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。
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) The reaction medium for reversibly causing the electron transfer reaction between components (a) and (b) is selected from the group consisting of chain hydrocarbons, alicyclic hydrocarbons, and halogenated hydrocarbons. Compounds are used.
By using the compound of component (c), there is little desensitization to the color development caused by the reaction between component (a) and component (b), and it functions effectively in improving color change behavior and color density due to heating.
In addition, the higher the number of carbon atoms in the alkyl group, the higher the crystallinity of the hydroxybenzoic acid ester of the component (b), and by adding the component (c), the hydroxybenzoic acid ester with high crystallinity has a discoloration temperature in the low temperature range. It becomes available for use.
Examples of chain hydrocarbons include saturated chain hydrocarbons such as pentadecane, hexadecane, heptadecane, octadecane, nonadecane, eicosane, heneicosane, docosane, tricosane, tetracosane, pentacosane, hexacosane, heptacosane, octacosane, nonacosane, and triacontane; -Pentadecene, 1-hexadecene, 1-heptadecene, 1-octadecene, 1-nonadecene, 1-eicosene, 1-heneicosene, 1-docosene, 1-tricosene, 1-tetracosene, 1-pentacosene, 1-hexacosene, 1-heptacosene Examples include unsaturated chain hydrocarbons such as , 1-octacosene, 1-nonacosene, and 1-triacontene.
Examples of alicyclic hydrocarbons include cyclooctane, cyclododecane, n-pentadecylcyclohexane, n-octadecylcyclohexane, n-nonadecylcyclohexane, and decahydronaphthalene.
Examples of halogenated hydrocarbons include 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. I can give an example.
(d)軟化点が5℃以上、且つ、質量平均分子量が200~10万のスチレン系化合物を以下に例示する。
スチレン系化合物は質量平均分子量が200~6000ものが好適に用いられる。
なお、質量平均分子量は、GPC法(ゲル浸透クロマトグラフ法)により測定する。
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(質量平均分子量2000)、ハイマーST-95(質量平均分子量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(質量平均分子量317)、ピコラスチックA75(質量平均分子量917)、理化ハーキュレス(株)製、商品名:ピコラスチックD125(質量平均分子量3000)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(質量平均分子量664)、クリスタレックス3100(質量平均分子量1020)、クリスタレックス1120(質量平均分子量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(質量平均分子量950)、ピコテックス100(質量平均分子量1740)等が用いられる。
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。
(d)成分を添加することにより、反応媒体である、鎖式炭化水素類、脂環族炭化水素類、芳香族炭化水素類、およびハロゲン化炭化水素類からなる群から選ばれる化合物の極性が変化するため、(b)成分の反応媒体に対する溶解性が減少し、徐々に(b)成分の結晶化が進行することになる。そのため、発色状態から降温過程で消色誘発温度迄冷却した可逆熱変色性組成物を内包してなる可逆熱変色性マイクロカプセル顔料(以下、簡単に、マイクロカプセル顔料ということがある)は放置すると消色する。
(d) Examples of styrenic compounds having a softening point of 5° C. or higher and a mass average molecular weight of 200 to 100,000 are listed below.
Styrene compounds having a mass average molecular weight of 200 to 6,000 are preferably used.
Note that the mass average molecular weight is measured by GPC method (gel permeation chromatography method).
Examples of the styrene compound include low molecular weight polystyrene, styrene-α-methylstyrene copolymer, α-methylstyrene polymer, and copolymer of α-methylstyrene and vinyltoluene.
As the low molecular weight polystyrene, products such as Hymer SB-75 (mass average molecular weight 2000) and Hymer ST-95 (mass average molecular weight 4000) manufactured by Sanyo Chemical Industries, Ltd. are used.
Examples of the styrene-α-methylstyrene copolymer include products manufactured by Rika Hercules Co., Ltd., trade names: Picolastic A5 (mass average molecular weight 317), Picolastic A75 (mass average molecular weight 917), manufactured by Rika Hercules Co., Ltd. Trade name: Picolastic D125 (mass average molecular weight 3000) or the like is used.
As α-methylstyrene polymers, products manufactured by Rika Hercules Co., Ltd., product names: Crystallex 3085 (mass average molecular weight 664), Crystallex 3100 (mass average molecular weight 1020), Crystallex 1120 (mass average molecular weight 2420), etc. used.
As the copolymer of α-methylstyrene and vinyltoluene, products such as Picotex LC (mass average molecular weight 950) and Picotex 100 (mass average molecular weight 1740) manufactured by Rika Hercules Co., Ltd. are used.
The styrene compounds may be used alone or in combination of two or more.
By adding component (d), the polarity of the reaction medium, a compound selected from the group consisting of chain hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, and halogenated hydrocarbons, can be changed. As a result, the solubility of component (b) in the reaction medium decreases, and crystallization of component (b) gradually progresses. Therefore, if a reversible thermochromic microcapsule pigment (hereinafter simply referred to as a microcapsule pigment) containing a reversible thermochromic composition that has been cooled from a colored state to a discoloration-inducing temperature during the cooling process is left unattended. Decolorize.
本発明によるマイクロカプセル顔料は、(e)融点が50℃以上の、アルコール類、エステル類、エーテル類、ケトン類、酸アミド類、及び芳香族炭化水素類からなる群から選ばれる化合物(以下、簡単に、(e)成分ということがある)を更に含むことが好ましい。(e)成分を以下に例示する。
アルコール類としては、ヘキサデカン1-オール、ヘプタデカン1-オール、オクタデカン1-オール、ノナデカン1-オール、エイコサン1-オール、ヘンエイコサン1-オール、ドコサン1-オール、テトラコサン1-オール、ヘキサコサン1-オール、オクタコサン1-オール、トリアコンタン1-オール等が挙げられる。
The microcapsule pigment according to the present invention comprises (e) a compound selected from the group consisting of alcohols, esters, ethers, ketones, acid amides, and aromatic hydrocarbons having a melting point of 50°C or higher (hereinafter referred to as It is preferable to further include (sometimes simply referred to as component (e)). The component (e) is illustrated below.
Examples of alcohols include hexadecane 1-ol, heptadecan 1-ol, octadecane 1-ol, nonadecan 1-ol, eicosan 1-ol, heneicosan 1-ol, docosan 1-ol, tetracosan 1-ol, hexacosan 1-ol, Examples include octacosan 1-ol and triacontan 1-ol.
エステル類としては、ラウリン酸エイコシル、ラウリン酸ベヘニル、ラウリン酸テトラコシル、ラウリン酸ヘキサコシル、ラウリン酸オクタコシル、ミリスチン酸セチル、ミリスチン酸ステアリル、ミリシチン酸エイコシル、ミリスチン酸ベヘニル、ミリスチン酸テトラコシル、ミリスチン酸ヘキサコシル、ミリスチン酸オクタコシル、パルミチン酸ミリスチル、パルミチン酸セチル、パルミチン酸ステアリル、パルミチン酸エイコシル、パルミチン酸ベヘニル、パルミチン酸テトラコシル、パルミチン酸ヘキサコシル、パルミチン酸オクタコシル、ステアリン酸セチル、ステアリン酸ステアリル、ステアリン酸エイコシル、ステアリン酸ベヘニル、ステアリン酸テトラコシル、ステアリン酸ヘキサコシル、ステアリン酸オクタコシル、エイコ酸デシル、エイコ酸ウンデシル、エイコ酸トリデシル、エイコ酸ミリスチル、エイコ酸セチル、エイコ酸ステアリル、エイコ酸エイコシル、エイコ酸ドコシル、エイコ酸テトラコシル、エイコ酸ヘキサコシル、エイコ酸オクタコシル、ベヘン酸メチル、ベヘン酸ヘキシル、ベヘン酸オクチル、ベヘン酸デシル、ベヘン酸ウンデシル、ベヘン酸ラウリル、ベヘン酸トリデシル、ベヘン酸ミリスチル、ベヘン酸セチル、ベヘン酸ステアリル、ベヘン酸エイコシル、べへン酸ベヘニル、ベヘン酸テトラコシル、ベヘン酸ヘキサコシル、ベヘン酸オクタコシル、シュウ酸ジステアリル、シュウ酸ジエイコシル、シュウ酸ベヘニル、コハク酸ジステアリル、コハク酸エイコシル、コハク酸ベヘニル、グルタル酸ジステアリル、グルタル酸ジエイコシル、グルタル酸ベヘニル、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、アジピン酸エイコシル、アジピン酸ベヘニル、スベリン酸ジセチル、スベリン酸ジステアリル、スベリン酸ジエイコシル、スベリン酸ベヘニル、アゼライン酸ミリスチル、アゼライン酸ジセチル、アゼライン酸ジステアリル、アゼライン酸エイコシル、アゼライン酸ベヘニル、セバシン酸ジミリスチル、セバシン酸ジセチル、セバシン酸ジステアリル、セバシン酸ジエイコシル、セバシン酸ジベヘニル、1,14-テトラデカメチレンジカルボン酸ジトリデシル、1,14-テトラデカメチレンジカルボン酸ジミリスチル、1,14-テトラデカメチレンジカルボン酸ジセチル、1,14-テトラデカメチレンジカルボン酸ジパルミチル、1,14-テトラデカメチレンジカルボン酸ジステアリル、1,14-テトラデカメチレンジカルボン酸ジエイコシル、1,14-テトラデカメチレンジカルボン酸ジベヘニル、1,16-ヘキサデカメチレンジカルボン酸ジラウリル、1,16-ヘキサデカメチレンジカルボン酸ジトリデシル、1,16-ヘキサデカメチレンジカルボン酸ジミリスチル、1,16-ヘキサデカメチレンジカルボン酸ジセチル、1,16-ヘキサデカメチレンジカルボン酸ジパルミチル、1,16-ヘキサデカメチレンジカルボン酸ジステアリル、1,16-ヘキサデカメチレンジカルボン酸ジエイコシル、1,16-ヘキサデカメチレンジカルボン酸ジベヘニル、1,18-オクタデカメチレンジカルボン酸ジデシル、1,18-オクタデカメチレンジカルボン酸ジラウリル、1,18-オクタデカメチレンジカルボン酸ジトリデシル、1,18-オクタデカメチレンジカルボン酸ジミリスチル、1,18-オクタデカメチレンジカルボン酸ジセチル、1,18-オクタデカメチレンジカルボン酸ジパルミチル、1,18-オクタデカメチレンジカルボン酸ジステアリル、1,18-オクタデカメチレンジカルボン酸ジエイコシル、1,18-オクタデカメチレンジカルボン酸ジベヘニル、1,20-エイコシルメチレンジカルボン酸ジデシル、1,20-エイコシルメチレンジカルボン酸ジラウリル、1,20-エイコシルメチレンジカルボン酸ジトリデシル、1,20-エイコシルメチレンジカルボン酸ジミリスチル、1,20-エイコシルメチレンジカルボン酸ジセチル、1,20-エイコシルメチレンジカルボン酸ジパルミチル、1,20-エイコシルメチレンジカルボン酸ジステアリル、1,20-エイコシルメチレンジカルボン酸ジエイコシル、1,20-エイコシルメチレンジカルボン酸ジベヘニル、トリミリスチン、トリパルミチン、トリステアリン、トリノナデカノイン、カプロン酸コレステロール、カプリル酸コレステロール、カプリン酸コレステロール、ウンデカン酸コレステロール、ラウリン酸コレステロール、ミリスチン酸コレステロール、パルミチン酸コレステロール、ステアリン酸コレステロール、エイコサン酸コレステロール、ベヘン酸コレステロール等が挙げられる。 Esters include eicosyl laurate, behenyl laurate, tetracosyl laurate, hexacosyl laurate, octacosyl laurate, cetyl myristate, stearyl myristate, eicosyl myristate, behenyl myristate, tetracosyl myristate, hexacosyl myristate, myristicin. Octacosyl acid, myristyl palmitate, cetyl palmitate, stearyl palmitate, eicosyl palmitate, behenyl palmitate, tetracosyl palmitate, hexacosyl palmitate, octacosyl palmitate, cetyl stearate, stearyl stearate, eicosyl stearate, behenyl stearate , Tetracosyl stearate, Hexacosyl stearate, Octacosyl stearate, Decyl eicoate, Undecyl eicoate, Tridecyl eicoate, Myristyl eicoate, Cetyl eicoate, Stearyl eicoate, Eicosyl eicoate, Docosyl eicoate, Tetracosyl eicoate, Eico Hexacosyl acid, octacosyl eicoate, methyl behenate, hexyl behenate, octyl behenate, decyl behenate, undecyl behenate, lauryl behenate, tridecyl behenate, myristyl behenate, cetyl behenate, stearyl behenate, eicosyl behenate , behenyl behenate, tetracosyl behenate, hexacosyl behenate, octacosyl behenate, distearyl oxalate, diicosyl oxalate, behenyl oxalate, distearyl succinate, eicosyl succinate, behenyl succinate, distearyl glutarate, Dieicosyl glutarate, behenyl glutarate, dimyristyl adipate, dicetyl adipate, distearyl adipate, eicosyl adipate, behenyl adipate, dicetyl suberate, distearyl suberate, dieicosyl suberate, behenyl suberate, myristyl azelate, Dicetyl azelate, distearyl azelate, eicosyl azelate, behenyl azelate, dimyristyl sebacate, dicetyl sebacate, distearyl sebacate, dieicosyl sebacate, dibehenyl sebacate, ditridecyl 1,14-tetradecamethylenedicarboxylate, 1 , dimyristyl 14-tetradecamethylenedicarboxylate, dicetyl 1,14-tetradecamethylenedicarboxylate, dipalmityl 1,14-tetradecamethylenedicarboxylate, distearyl 1,14-tetradecamethylenedicarboxylate, 1,14-tetradeca dieicosyl methylenedicarboxylate, dibehenyl 1,14-tetradecamethylenedicarboxylate, dilauryl 1,16-hexadecamethylenedicarboxylate, ditridecyl 1,16-hexadecamethylenedicarboxylate, dimyristyl 1,16-hexadecamethylenedicarboxylate, 1 , dicetyl 16-hexadecamethylene dicarboxylate, dipalmityl 1,16-hexadecamethylene dicarboxylate, distearyl 1,16-hexadecamethylene dicarboxylate, dieicosyl 1,16-hexadecamethylene dicarboxylate, 1,16-hexadeca Dibehenyl methylene dicarboxylate, didecyl 1,18-octadecamethylene dicarboxylate, dilauryl 1,18-octadecamethylene dicarboxylate, ditridecyl 1,18-octadecamethylene dicarboxylate, dimyristyl 1,18-octadecamethylene dicarboxylate, 1 , dicetyl 18-octadecamethylenedicarboxylate, dipalmityl 1,18-octadecamethylenedicarboxylate, distearyl 1,18-octadecamethylenedicarboxylate, dieicosyl 1,18-octadecamethylenedicarboxylate, 1,18-octadeca Dibehenyl methylenedicarboxylate, didecyl 1,20-eicosylmethylenedicarboxylate, dilauryl 1,20-eicosylmethylenedicarboxylate, ditridecyl 1,20-eicosylmethylenedicarboxylate, dimyristyl 1,20-eicosylmethylenedicarboxylate, 1 , dicetyl 20-eicosylmethylene dicarboxylate, dipalmityl 1,20-eicosylmethylene dicarboxylate, distearyl 1,20-eicosyl methylene dicarboxylate, dieicosyl 1,20-eicosyl methylene dicarboxylate, 1,20-eicosyl Dibehenyl methylenedicarboxylate, trimyristin, tripalmitin, tristearin, trinonadecanoin, cholesterol caproate, cholesterol caprylate, cholesterol caprate, cholesterol undecanoate, cholesterol laurate, cholesterol myristate, cholesterol palmitate, cholesterol stearate , cholesterol eicosanoate, cholesterol behenate, and the like.
エーテル類としては、ペンタデシルエーエル、ジヘキサデシルエーテル、ジオクタデシルエーテル、ジエイコシルエーテル、ジドコシルエーテル等が挙げられる。 Examples of the ethers include pentadecyl ether, dihexadecyl ether, dioctadecyl ether, dieicosyl ether, and didocosyl ether.
ケトン類としては、ジオクチルケトン、ジノニルケトン、ジウンデシルケトン、ジトリデシルケトン、ジペンタデシルケトン、ジヘプタデシルケトン、ジノナデシルケトン、フェニルオクチルケトン、フェニルウンデシルケトン、フェニルトリデシルケトン、フェニルペンタデシルケトン、フェニルヘプタデシルケトン等が挙げられる。 Ketones include dioctyl ketone, dinonyl ketone, diundecyl ketone, ditridecyl ketone, dipentadecyl ketone, diheptadecyl ketone, dinonadecyl ketone, phenyl octyl ketone, phenyl undecyl ketone, phenyl tridecyl ketone, and phenyl pentadecyl. Examples include ketone, phenylheptadecyl ketone, and the like.
酸アミド類としては、ヘキシルアミド、ヘプチルアミド、オクチルアミド、ノニルアミド、デシルアミド、ウンデシルアミド、ラウリルアミド、トリデシルアミド、ミリスチルアミド、パルミチルアミド、ステアリルアミド、エイコシルアミド、ベヘニルアミド、ヘキサコシルアミド、オクタコシルアミド等が挙げられる。 Acid amides include hexylamide, heptylamide, octylamide, nonylamide, decylamide, undecylamide, laurylamide, tridecylamide, myristylamide, palmitylamide, stearylamide, eicosylamide, behenylamide, and hexacosylamide. Examples include amide, octacosylamide, and the like.
芳香族炭化水素類としては、ビフェニル、オルトターフェニル、メタターフェニル、パラターフェニル、テルチオフェン等が挙げられる。 Examples of aromatic hydrocarbons include biphenyl, orthoterphenyl, metaterphenyl, paraterphenyl, and terthiophene.
(e)成分として下記表に記載された化合物を用いることもできる。
発色状態から降温過程で(d)成分によって(b)成分の結晶化が進行して消色するが、完全に消色するまでに時間がかかることがあり、(e)成分を添加することにより更に結晶化を促進させ、消色鋭敏性を向上させることができる。 In the process of cooling down from the colored state, component (d) causes the crystallization of component (b) to progress and the color disappears, but it may take some time for the color to completely disappear, so adding component (e) Furthermore, crystallization can be promoted and decolorization sensitivity can be improved.
(a)、(b)、(c)、(d)成分の割合は、色濃度、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、(a)成分1に対して、(b)成分0.1~50、好ましくは0.5~20、(c)成分1~200、好ましくは5~100、(d)成分0.1~10.0、好ましくは0.5~5.0の範囲、(e)成分0.1~5.0、好ましくは0.1~3.0の範囲である(前記した割合はいずれも質量部である)。 The ratio of components (a), (b), (c), and (d) depends on the color density, discoloration temperature, discoloration form, and type of each component, but generally the component ratio that provides the desired characteristics (a) component 1, (b) component 0.1 to 50, preferably 0.5 to 20, (c) component 1 to 200, preferably 5 to 100, and (d) component 0.1. ~10.0, preferably in the range of 0.5 to 5.0, and component (e) in the range of 0.1 to 5.0, preferably 0.1 to 3.0 (all of the above ratios are by weight). ).
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。
可逆熱変色性組成物を内包してなるマイクロカプセル顔料は、粒子径0.1~100μm、好ましくは0.5~30μm、より好ましくは1~20μmの範囲が実用性を満たす。
尚、粒子径及び平均粒子径の測定は、マウンテック社製の画像解析式粒度分布測定ソフトウェア「マックビュー」を用いて粒子の領域を判定し、粒子の領域の面積から投影面積円相当径(Heywood径)を算出し、その値による等体積球相当の粒子の粒子径及び平均粒子径として測定した値である。また、全ての粒子或いは大部分の粒子の粒子径が0.2μmを超える場合には、粒度分布測定装置(ベックマン・コールター株式会社製、製品名:Multisizer 4e)を用いてコールター法により等体積球相当の粒子の粒子径及び平均粒子径として測定することも可能である。
更に、コールター法による測定装置を用いて計測した数値を基にしてキャリブレーションしたレーザー回折/散乱式粒子径分布測定装置(装置名:LA-300、株式会社堀場製作所製)を用いて、体積基準の粒子径及び平均粒子径(メジアン径)を測定しても良い。
The reversible thermochromic composition is used by being encapsulated in microcapsules. It not only does not deteriorate its function even when it comes into contact with chemically active substances such as acidic substances, basic substances, peroxides, or other solvent components, but also maintains heat-resistant stability. This is because the reversible thermochromic composition can maintain the same composition under various usage conditions and exhibit the same effects.
The microcapsule pigment containing the reversible thermochromic composition satisfies practicality when the particle diameter is in the range of 0.1 to 100 μm, preferably 0.5 to 30 μm, and more preferably 1 to 20 μm.
In addition, to measure the particle size and average particle size, the area of the particle is determined using the image analysis type particle size distribution measuring software "Macview" manufactured by Mountech, and the projected area circle equivalent diameter (Heywood) is determined from the area of the particle area. This is the value measured as the particle diameter and average particle diameter of particles equivalent to an equal volume sphere based on the calculated value. In addition, if the particle diameter of all or most of the particles exceeds 0.2 μm, equal volume spheres should be measured by the Coulter method using a particle size distribution analyzer (manufactured by Beckman Coulter, Inc., product name: Multisizer 4e). It is also possible to measure the particle size of the corresponding particles and the average particle size.
Furthermore, using a laser diffraction/scattering particle size distribution measuring device (device name: LA-300, manufactured by Horiba, Ltd.) that was calibrated based on the values measured using a measuring device using the Coulter method, the volume standard The particle diameter and average particle diameter (median diameter) may be measured.
尚、各成分は各々2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。
光安定剤としては、(a)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質量%、好ましくは0.8~16質量%の割合で配合される。なかでも、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、一般染顔料(非熱変色性)を配合することもできる。
Incidentally, each component may be a mixture of two or more kinds of compounds, and furthermore, a light stabilizer can be added within a range that does not impede the function.
Examples of light stabilizers include ultraviolet absorbers, visible light absorbers, infrared absorbers, antioxidants, carotenes, pigments, amines, and phenols that prevent photodeterioration caused by the excited state caused by the photoreaction of component (a). Examples include compounds that suppress oxidation reactions, such as singlet oxygen quenchers such as nickel complexes, sulfides, superoxide anion quenchers such as complexes of oxide dismustase and cobalt, and nickel, and ozone quenchers. It is blended in a proportion of 0.3 to 24% by weight, preferably 0.8 to 16% by weight. Among these, a system in which a UV absorber is used in combination with an antioxidant and/or a singlet oxygen quencher is particularly effective in improving light resistance.
Furthermore, anti-aging agents, antistatic agents, polarizers, thixotropy agents, antifoaming agents, etc. can be added as necessary to improve functionality.
Furthermore, general dyes and pigments (non-thermochromic) can also be blended.
(a)、(b)、(c)、及び(d)成分、又は、(a)、(b)、(c)、(d)、及び(e)成分を含んでなる可逆熱変色性組成物を内包してなる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。
T1は、好ましくは15~35℃であり、より好ましくは15~27℃である。T2は、好ましくは25~50℃であり、より好ましくは25~40℃である。
Reversible thermochromic composition comprising components (a), (b), (c), and (d), or components (a), (b), (c), (d), and (e) The color change characteristics of microcapsule pigments containing substances will be explained.
A reversible thermochromic composition that exhibits a decolorized state begins to develop color at the coloring start temperature (T 1 ) during the heating process, becomes fully colored when it reaches the complete coloring temperature (T 2 ), and disappears in the process of cooling down. A reversible thermochromic composition cooled to a color-inducing temperature will discolor when left to stand.
T 1 is preferably 15-35°C, more preferably 15-27°C. T 2 is preferably 25-50°C, more preferably 25-40°C.
可逆熱変色性マイクロカプセル顔料は、必要により添加剤を含むビヒクル中に分散させて液状組成物とすることで、(i)スクリーン印刷、オフセット印刷、プロセス印刷、グラビヤ印刷、コーター、タンポ印刷等に用いられる印刷インキ、(ii)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、浸漬塗装等に用いられる塗料、(iii)マーキングペン用、ボールペン用、万年筆用、筆ペン用等の筆記具用インキや,(iv)塗布具用インキ、(v)絵の具、(vi)化粧料、または(vii)繊維用着色液等の可逆熱変色性液状組成物に利用できる。 By dispersing the reversible thermochromic microcapsule pigment in a vehicle containing additives as necessary to form a liquid composition, it can be used in (i) screen printing, offset printing, process printing, gravure printing, coater printing, tampon printing, etc. Printing inks used, (ii) Paints used for brush coating, spray coating, electrostatic coating, electrodeposition coating, flow coating, roller coating, dip coating, etc., (iii) For marking pens, ballpoint pens, fountain pens, and brushes. It can be used in reversible thermochromic liquid compositions such as inks for writing instruments such as pens, (iv) inks for applicators, (v) paints, (vi) cosmetics, or (vii) coloring liquids for textiles.
添加剤としては、樹脂、架橋剤、硬化剤、乾燥剤、可塑剤、粘度調整剤、分散剤、紫外線吸収剤、赤外線吸収剤、酸化防止剤、光安定剤、溶解助剤、沈降防止剤、平滑剤、ゲル化剤、消泡剤、つや消し剤、浸透剤、pH調整剤、発泡剤、カップリング剤、保湿剤、防かび剤、防腐剤、防錆剤等が挙げられる。 Additives include resins, crosslinking agents, curing agents, desiccants, plasticizers, viscosity modifiers, dispersants, ultraviolet absorbers, infrared absorbers, antioxidants, light stabilizers, solubilizers, antisettling agents, Smoothing agents, gelling agents, antifoaming agents, matting agents, penetrating agents, pH adjusting agents, foaming agents, coupling agents, humectants, fungicides, preservatives, rust preventives, etc. are included.
本発明による液状組成物のビヒクルとしては、有機溶剤を含む油性ビヒクル、或いは、水と、必要により有機溶剤を含む水性ビヒクルが挙げられる。 Vehicles for the liquid composition according to the present invention include oil-based vehicles containing organic solvents, or aqueous vehicles containing water and, if necessary, organic solvents.
本発明において用いることができる有機溶剤としては、エタノール、プロパノール、ブタノール、グリセリン、ソルビトール、トリエタノールアミン、ジエタノールアミン、モノエタノールアミン、エチレングリコール、ジエチレングリコール、チオジエチレングリコール、ポリエチレングリコール、プロピレングリコール、ブチレングリコール、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノブチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノブチルエーテル、プロピレングリコールモノブチルエーテル、エチレングリコールモノメチルエーテルアセテート、スルフォラン、2-ピロリドン、N-メチル-2-ピロリドン等を挙げることができる。 Organic solvents that can be used in the present invention include ethanol, propanol, butanol, glycerin, sorbitol, triethanolamine, diethanolamine, monoethanolamine, ethylene glycol, diethylene glycol, thiodiethylene glycol, polyethylene glycol, propylene glycol, butylene glycol, and ethylene. Glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monobutyl ether, ethylene glycol monomethyl ether acetate, sulfolane, 2-pyrrolidone, N-methyl-2 - Pyrrolidone, etc. can be mentioned.
液状組成物としては、ビヒクル中に剪断減粘性付与剤を含む剪断減粘性液状組成物、ビヒクル中に水溶性高分子凝集剤を含み、顔料を緩やかな凝集状態に懸濁させた凝集性液状組成物を挙げることができる。 Examples of the liquid composition include a shear-thinning liquid composition containing a shear-thinning viscosity imparting agent in a vehicle, and a flocculating liquid composition containing a water-soluble polymer flocculant in a vehicle and suspending pigment in a mildly agglomerated state. I can name things.
液状組成物が剪断減粘性付与剤を含むことにより、例えばインキ組成物として利用した場合に、顔料の凝集、沈降を抑制することができると共に、筆跡の滲みを抑制することができるため、良好な筆跡を形成できる。 When the liquid composition contains a shear thinning agent, for example, when used as an ink composition, it is possible to suppress aggregation and sedimentation of pigments, and also to suppress blurring of handwriting, making it a good product. Can form handwriting.
更に、剪断減粘性付与剤を含むインキ組成物をボールペンに充填する場合、不使用時のボールとチップの間隙からのインキ漏れを防止したり、筆記先端部を上向き(正立状態)で放置した場合のインキ組成物の逆流を防止することができる。 Furthermore, when filling a ballpoint pen with an ink composition containing a shear thinning agent, it is necessary to prevent ink from leaking from the gap between the ball and the tip when not in use, or to prevent the writing tip from being left facing upward (in an upright position). This can prevent backflow of the ink composition.
剪断減粘性付与剤としては、キサンタンガム、ウェランガム、構成単糖がグルコースとガラクトースの有機酸修飾ヘテロ多糖体であるサクシノグリカン(平均分子量約100万乃至800万)、グアーガム、ローカストビーンガム及びその誘導体、ヒドロキシエチルセルロース、アルギン酸アルキルエステル類、メタクリル酸のアルキルエステルを主成分とする分子量10万~15万の重合体、グルコマンナン、寒天やカラゲニン等の海藻より抽出されるゲル化能を有する増粘多糖類、ベンジリデンソルビトール及びベンジリデンキシリトール又はこれらの誘導体、架橋性アクリル酸重合体、無機質微粒子、ポリグリセリン脂肪酸エステル、ポリオキシエチレンソルビタン脂肪酸エステル、ポリエチレングリコール脂肪酸エステル、ポリオキシエチレンアルキルエーテル、ポリオキシプロピレンアルキルエーテル、ポリオキシエチレンアルキルフェニルエーテル、脂肪酸アミド等のHLB値が8~12のノニオン系界面活性剤、ジアルキル又はジアルケニルスルホコハク酸の塩類。N-アルキル-2-ピロリドンとアニオン系界面活性剤の混合物、ポリビニルアルコールとアクリル系樹脂の混合物を例示できる。 Examples of shear thinning agents include xanthan gum, welan gum, succinoglycan (average molecular weight of about 1 million to 8 million), which is an organic acid-modified heteropolysaccharide whose constituent monosaccharides are glucose and galactose, guar gum, locust bean gum, and derivatives thereof. , hydroxyethylcellulose, alginate alkyl esters, polymers with a molecular weight of 100,000 to 150,000 whose main components are alkyl esters of methacrylic acid, glucomannan, thickeners with gelling ability extracted from seaweed such as agar and carrageenan. Saccharides, benzylidene sorbitol and benzylidene xylitol or their derivatives, cross-linked acrylic acid polymers, inorganic fine particles, polyglycerin fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyethylene glycol fatty acid esters, polyoxyethylene alkyl ethers, polyoxypropylene alkyl ethers , nonionic surfactants with an HLB value of 8 to 12 such as polyoxyethylene alkylphenyl ether, fatty acid amide, and salts of dialkyl or dialkenyl sulfosuccinic acids. Examples include a mixture of N-alkyl-2-pyrrolidone and anionic surfactant, and a mixture of polyvinyl alcohol and acrylic resin.
本発明に用いることができる水溶性高分子凝集剤としては、ポリビニルピロリドン、ポリエチレンオキサイド、水溶性多糖類等が挙げられる。 Examples of water-soluble polymer flocculants that can be used in the present invention include polyvinylpyrrolidone, polyethylene oxide, and water-soluble polysaccharides.
水溶性多糖類としてはトラガントガム、グアーガム、プルラン、サイクロデキストリン、水溶性セルロース誘導体等が挙げられ、水溶性セルロース誘導体の具体例としてはメチルセルロース、ヒドロキシエチルセルロース、ヒドロキシプロピルセルロース、ヒドロキシエチルメチルセルロース、ヒドロキシプロピルメチルセルロース等が挙げられる。 Examples of water-soluble polysaccharides include gum tragacanth, guar gum, pullulan, cyclodextrin, water-soluble cellulose derivatives, etc. Specific examples of water-soluble cellulose derivatives include methylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxyethylmethylcellulose, hydroxypropylmethylcellulose, etc. can be mentioned.
また、液状組成物をインキ組成物としてボールペンに充填して用いる場合は、オレイン酸等の高級脂肪酸、長鎖アルキル基を有するノニオン性界面活性剤、ポリエーテル変性シリコーンオイル、チオ亜燐酸トリ(アルコキシカルボニルメチルエステル)やチオ亜燐酸トリ(アルコキシカルボニルエチルエステル)等のチオ亜燐酸トリエステル、ポリオキシエチレンアルキルエーテル又はポリオキシエチレンアルキルアリールエーテルのリン酸モノエステル、ポリオキシエチレンアルキルエーテル又はポリオキシエチレンアルキルアリールエーテルのリン酸ジエステル、或いは、それらの金属塩、アンモニウム塩、アミン塩、アルカノールアミン塩等の潤滑剤を添加してボール受け座の摩耗を防止することが好ましい。 In addition, when the liquid composition is used as an ink composition by being filled into a ballpoint pen, higher fatty acids such as oleic acid, nonionic surfactants having long-chain alkyl groups, polyether-modified silicone oil, tri(alkoxy thiophosphite), etc. thiophosphite triesters such as carbonyl methyl ester) and thiophosphite tri(alkoxycarbonylethyl ester), phosphoric acid monoesters of polyoxyethylene alkyl ether or polyoxyethylene alkylaryl ether, polyoxyethylene alkyl ether or polyoxyethylene It is preferable to add a lubricant such as a phosphoric acid diester of alkylaryl ether, or a metal salt, ammonium salt, amine salt, or alkanolamine salt thereof to prevent wear of the ball seat.
更に、2,5-ジメルカプト-1,3,4-チアジアゾール及び/又はその塩を含有させることにより、インキのpHが酸性或いはアルカリ領域であっても、一度凍結したインキが再度解凍された後に生じるマイクロカプセル顔料の分散不良や凝集を抑制でき、インキの粘度の上昇やそれに伴う筆跡カスレや淡色化を防止することができると共に、ボールペンに用いる場合はボールの腐食を防止することもできる。 Furthermore, by containing 2,5-dimercapto-1,3,4-thiadiazole and/or its salt, even if the pH of the ink is in the acidic or alkaline range, the ink that has been frozen once is thawed again. It can suppress poor dispersion and agglomeration of microcapsule pigments, prevent an increase in ink viscosity and the resulting blurring and lightening of handwriting, and when used in ballpoint pens, it can also prevent ball corrosion.
その他、必要に応じて(i)アクリル樹脂、スチレンマレイン酸共重合物、セルロース誘導体、ポリビニルピロリドン、ポリビニルアルコール、デキストリン等の、紙面への固着性や粘性を付与する樹脂、(ii)炭酸ナトリウム、燐酸ナトリウム、酢酸ソーダ等の無機塩類、水溶性のアミン化合物等の有機塩基性化合物等のpH調整剤、(iii)ベンゾトリアゾール、トリルトリアゾール、ジシクロヘキシルアンモニウムナイトライト、ジイソプロピルアンモニウムナイトライト、サポニン等の防錆剤、(iv)フェノール、1,2-ベンズチアゾリン3-オンのナトリウム塩、安息香酸ナトリウム、デヒドロ酢酸ナトリウム、ソルビン酸カリウム、パラオキシ安息香酸プロピル、2,3,5,6-テトラクロロ-4-(メチルスルフォニル)ピリジン等の防腐剤或いは防黴剤、(v)尿素、ノニオン系界面活性剤、還元又は非還元デンプン加水分解物、トレハロース等のオリゴ糖類、ショ糖、サイクロデキストリン、ぶどう糖、デキストリン、ソルビット、マンニット、ピロリン酸ナトリウム等の湿潤剤、(vi)消泡剤、(vii)分散剤、(viii)インキ組成物の浸透性を向上させるフッ素系界面活性剤やノニオン系の界面活性剤を添加してもよい。 In addition, as necessary, (i) resins that impart adhesion to the paper surface and viscosity, such as acrylic resins, styrene-maleic acid copolymers, cellulose derivatives, polyvinylpyrrolidone, polyvinyl alcohol, and dextrins, (ii) sodium carbonate, pH adjusters such as inorganic salts such as sodium phosphate and sodium acetate, organic basic compounds such as water-soluble amine compounds, (iii) preventive agents such as benzotriazole, tolyltriazole, dicyclohexylammonium nitrite, diisopropylammonium nitrite, saponin, etc. Rust agent, (iv) Phenol, sodium salt of 1,2-benzthiazolin 3-one, sodium benzoate, sodium dehydroacetate, potassium sorbate, propyl paraoxybenzoate, 2,3,5,6-tetrachloro-4 - Preservatives or antifungal agents such as (methylsulfonyl)pyridine, (v) urea, nonionic surfactants, reduced or non-reduced starch hydrolysates, oligosaccharides such as trehalose, sucrose, cyclodextrin, glucose, dextrin , wetting agents such as sorbitol, mannitol, and sodium pyrophosphate, (vi) antifoaming agents, (vii) dispersants, and (viii) fluorine-based surfactants and nonionic surfactants that improve the permeability of ink compositions. Agents may also be added.
液状組成物の全質量に対し、好ましくは5~40質量%、より好ましくは10~40質量%、さらに好ましくは10~30質量%の可逆熱変色性マイクロカプセル顔料を含有することができる。マイクロカプセル顔料の含有量が上記の範囲であることにより、望ましい発色濃度が達成でき、更にインキ組成物として用いた場合にはその流出性の低下を防止することができる。 The reversible thermochromic microcapsule pigment can be contained in an amount of preferably 5 to 40% by weight, more preferably 10 to 40% by weight, and still more preferably 10 to 30% by weight based on the total weight of the liquid composition. When the content of the microcapsule pigment is within the above range, a desired color density can be achieved, and furthermore, when used as an ink composition, a decrease in flowability can be prevented.
本発明による液状組成物を収容することができる筆記具について説明する。一実施形態において、筆記具は、インキ組成物を収容した軸筒及び軸筒内のインキを導出するペン体を備えてなる。ペン体としては、マーキングペン体、ボールペン体、筆ペン体等が挙げられる。マーキングペン体としては、繊維チップ、フェルトチップ、プラスチックチップ等のマーキングチップが挙げられる。ボールペン体としては、ボールペンチップが挙げられる。 A writing instrument capable of containing the liquid composition according to the present invention will be described. In one embodiment, the writing instrument includes a barrel housing an ink composition and a pen body that draws out the ink inside the barrel. Examples of the pen body include a marking pen body, a ballpoint pen body, a brush pen body, and the like. Examples of the marking pen body include marking tips such as fiber tips, felt tips, and plastic tips. Examples of the ballpoint pen body include a ballpoint pen tip.
本発明によるマイクロカプセル顔料は、支持体と組み合わせて、積層体とすることができ、マイクロカプセル顔料を含んでなる可逆熱変色層と支持体とを具備してなる。また、支持体にマイクロカプセル顔料が含まれている成形体であってもよい。
具体的には、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て積層体を得たり、或いは支持体中に分散して成形体を得ることができる。
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成形体を得ることもできる。
The microcapsule pigment according to the present invention can be combined with a support to form a laminate, which comprises a reversible thermochromic layer containing the microcapsule pigment and the support. Moreover, a molded article in which the support contains a microcapsule pigment may be used.
Specifically, microcapsule pigments are dispersed in a medium containing a binder, which is a film-forming material, and applied as reversible thermochromic materials such as inks and paints, using conventionally known methods such as screen printing, Paper, synthetic paper, A laminate can be obtained by forming a reversible thermochromic layer on a support such as fabric, flocked or raised fabric, non-woven fabric, synthetic leather, leather, plastic, glass, ceramics, wood, stone, etc., or it can be dispersed in a support. A molded article can be obtained.
Furthermore, it is also possible to obtain a molded article as an integrated material by kneading it into a thermoplastic in a molten state.
マイクロカプセル顔料を適用した製品として具体的には、以下のものを例示することができる。
(1)玩具類
人形及び動物形象玩具、人形及び動物形象玩具用毛髪、人形の家及び家具、衣類、帽子、鞄、靴等の人形用付属品、アクセサリー玩具、ぬいぐるみ、描画玩具、玩具用絵本、ジグソーパズル等のパズル玩具、積木玩具、ブロック玩具、粘土玩具、流動玩具、こま、凧、楽器玩具、料理玩具、鉄砲玩具、捕獲玩具、背景玩具、乗物、動物、植物、建築物、食品等を模した玩具等、
(2)衣類
Tシャツ、トレーナー、ブラウス、ドレス、水着、レインコート、スキーウェア等の被服、靴や靴紐等の履物、ハンカチ、タオル、ふろしき等の布製身の回り品、手袋、ネクタイ、帽子等、
(3)屋内装飾品
絨毯、カーテン、カーテン紐、テーブル掛け、敷物、クッション、額縁、造花、写真立て等、
(4)家具
布団、枕、マットレス等の寝具、照明器具、冷暖房器具等、
(5)装飾品
指輪、腕輪、ティアラ、イヤリング、髪止め、付け爪、リボン、スカーフ等、時計、眼鏡等、
(6)文房具類
筆記具、スタンプ具、消しゴム、下敷き、定規、粘着テープ等、
(7)日用品
口紅、アイシャドー、マニキュア、染毛剤、付け爪、付け爪用塗料等の化粧品、歯ブラシ等、
(8)台所用品
コップ、皿、箸、スプーン、フォーク、鍋、フライパン等、
(9)その他
カレンダー、ラベル、カード、記録材、及び偽造防止用の各種印刷物、絵本等の書籍、鞄、包装用容器、刺繍糸、運動用具、釣り具、コースター、楽器、カイロ、蓄冷剤、財布等の袋物、傘、乗物、建造物、温度検知用インジケーター、教習具等。
Specific examples of products to which microcapsule pigments are applied include the following.
(1) Toys Dolls and animal-shaped toys, hair for dolls and animal-shaped toys, doll houses and furniture, clothing, accessories for dolls such as hats, bags, shoes, accessory toys, stuffed animals, drawing toys, picture books for toys , puzzle toys such as jigsaw puzzles, building blocks toys, block toys, clay toys, fluid toys, spinning tops, kites, musical instrument toys, cooking toys, gun toys, capture toys, background toys, vehicles, animals, plants, buildings, food, etc. imitation toys, etc.
(2) Clothing Clothing such as T-shirts, sweatshirts, blouses, dresses, swimsuits, raincoats, ski wear, footwear such as shoes and shoelaces, cloth personal items such as handkerchiefs, towels, and furoshiki, gloves, ties, hats, etc.
(3) Indoor decorations carpets, curtains, curtain strings, table hangers, rugs, cushions, picture frames, artificial flowers, photo frames, etc.
(4) Furniture, bedding such as futons, pillows, and mattresses, lighting equipment, air conditioning equipment, etc.
(5) Accessories Rings, bangles, tiaras, earrings, hair clips, false nails, ribbons, scarves, etc., watches, glasses, etc.
(6) Stationery writing instruments, stamps, erasers, pads, rulers, adhesive tape, etc.
(7) Daily necessities Cosmetics such as lipstick, eye shadow, nail polish, hair dye, artificial nails, paint for artificial nails, toothbrushes, etc.
(8) Kitchen utensils: cups, plates, chopsticks, spoons, forks, pots, frying pans, etc.
(9) Other calendars, labels, cards, recording materials, various printed materials for preventing counterfeiting, books such as picture books, bags, packaging containers, embroidery thread, exercise equipment, fishing gear, coasters, musical instruments, body warmers, cold storage agents, Bags such as wallets, umbrellas, vehicles, buildings, temperature detection indicators, teaching materials, etc.
実施例1~14
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。
Examples 1 to 14
The composition used in the reversible thermochromic composition of the present invention is shown in the table below.
In addition, the numbers in parentheses in the table indicate parts by mass, and all the numbers indicating the blending amounts below are parts by mass.
表中の(d)成分について、ピコラスチックA75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D125は、低分子量ポリスチレン樹脂、軟化点125℃であり、ピコラスチックA5は、低分子量ポリスチレン樹脂、軟化点5℃である。
表中の(e)成分に記載された化合物1、2、6とは、(e)成分を例示した表に記載された各化合物である。
Regarding component (d) in the table, Picolastic A75 is a low molecular weight polystyrene resin with a softening point of 75°C, Picolastic D125 is a low molecular weight polystyrene resin with a softening point of 125°C, and Picolastic A5 is a low molecular weight polystyrene resin with a softening point of 125°C. Polystyrene resin, softening point 5°C.
Compounds 1, 2, and 6 listed as component (e) in the table are each compound listed in the table illustrating component (e).
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マイクロカプセル顔料を得た。
マイクロカプセル顔料について、以下の測定試料を作製した後、以下の測定方法により変色温度を測定した。
After heating and melting each reversible thermochromic composition to form a compatible solution, a microcapsule pigment in the form of a microcapsule encapsulated in an epoxy resin film was obtained by an interfacial polymerization reaction using an epoxy resin and an amine curing agent.
Regarding the microcapsule pigment, the following measurement samples were prepared, and then the discoloration temperature was measured by the following measurement method.
測定試料
マイクロカプセル顔料の変色特性は、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60部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 The color change characteristics of the microcapsule pigment were measured using a printed matter printed on high-quality paper by screen printing using a reversible thermochromic ink prepared by dispersing 40 parts of the microcapsule pigment in 60 parts of ethylene-vinyl acetate emulsion. And so.
測定方法
実施例1~14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40℃の温度幅で速度10℃/分にて加熱する。
40℃迄加熱した後、消色誘発温度迄冷却し、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、発色時の色濃度(明度値)を以下の表に示す。
Measurement method The measurement samples of Examples 1 to 14 were set at the specified location of a color difference meter [TC-3600 type color difference meter, manufactured by Tokyo Denshoku Co., Ltd.], and the temperature range was 0°C to 40°C at a speed of 10°C/min. Heat it up.
After heating to 40° C., the mixture was cooled to a temperature that induces decolorization and left to decolor.
The table below shows the color change, color development start temperature (T 1 ), complete color development temperature (T 2 ), decolorization induction temperature, and color density (brightness value) at the time of color development for each example.
比較例1、2
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。
Comparative examples 1 and 2
The compositions used in the reversible thermochromic composition are shown in the table below.
In addition, the numbers in parentheses in the table indicate parts by mass, and all the numbers indicating the blending amounts below are parts by mass.
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マイクロカプセル顔料を得た。
マイクロカプセル顔料について、以下の測定試料を作製した後、以下の測定方法により変色温度を測定した。
After heating and melting each reversible thermochromic composition to form a compatible solution, a microcapsule pigment in the form of a microcapsule encapsulated in an epoxy resin film was obtained by an interfacial polymerization reaction using an epoxy resin and an amine curing agent.
Regarding the microcapsule pigment, the following measurement samples were prepared, and then the discoloration temperature was measured by the following measurement method.
測定試料
マイクロカプセル顔料の変色特性は、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60部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 The color change characteristics of the microcapsule pigment were measured using a printed matter printed on high-quality paper by screen printing using a reversible thermochromic ink prepared by dispersing 40 parts of the microcapsule pigment in 60 parts of ethylene-vinyl acetate emulsion. And so.
測定方法
比較例1及び2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40℃の温度幅で速度10℃/分にて加熱する。
40℃迄加熱した後、消色誘発温度迄冷却し、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、発色時の色濃度(明度値)を以下の表に示す。
なお、表中の明度値は、小さいほど濃度が高く、大きいほど濃度が低いことを示している。
Measurement method: The measurement samples of Comparative Examples 1 and 2 were set at the specified location of a color difference meter [TC-3600 type color difference meter, manufactured by Tokyo Denshoku Co., Ltd.] and heated at a speed of 10 °C/min in a temperature range of 0 °C to 40 °C. Heat it up.
After heating to 40° C., the mixture was cooled to a temperature that induces decolorization and left to decolor.
The table below shows the color change, color development start temperature (T 1 ), complete color development temperature (T 2 ), decolorization induction temperature, and color density (brightness value) at the time of color development for each example.
Note that the smaller the brightness value in the table, the higher the density, and the larger the brightness value, the lower the density.
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。
可逆熱変色性シートは26℃以上に加温すると紫色を呈する。
可逆熱変色性シートを18℃迄冷却した後、放置する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 microcapsule pigment encapsulating the reversible thermochromic composition prepared in Example 1, 2.0 parts of fluorescent pigment (pink), 50.0 parts of acrylic resin emulsion, 3.0 parts of antifoaming agent, A reversible thermochromic screen ink consisting of 15.0 parts of turpentine emulsion was prepared.
A reversible thermochromic sheet was obtained by printing on polyester taffeta by screen printing using a reversible thermochromic screen ink to form a reversible thermochromic layer.
The reversible thermochromic sheet takes on a purple color when heated to 26°C or higher.
When the reversible thermochromic sheet is cooled to 18° C. and left to stand, the reversible thermochromic sheet exhibits a pink color.
応用例2
実施例2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。
シートは38℃以上に加温すると青色を呈する。
可逆熱変色性シートを26℃迄冷却した後、放置すると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 containing the reversible thermochromic composition prepared in Example 2 was uniformly dispersed and mixed in 50.0 parts of a linseed oil-based offset ink vehicle to form a reversible thermochromic offset ink. Prepared.
Offset printing was performed on high-quality paper using the offset ink to form a reversible thermochromic layer to obtain a reversible thermochromic sheet.
The sheet takes on a blue color when heated above 38°C.
When the reversible thermochromic sheet is cooled to 26° C. and left to stand, the reversible thermochromic sheet becomes colorless.
応用例3
実施例3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。
可逆熱変色性カップは50℃以上に加温すると青色を呈する。
可逆熱変色性カップを35℃迄冷却した後、放置すると可逆熱変色性カップは無色を呈する。
Application example 3
33.3 parts of the microcapsule pigment encapsulating the reversible thermochromic composition prepared in Example 3, 66.4 parts of hard type liquid epoxy resin, and 0.3 part of antifoaming agent were uniformly dispersed and kneaded. 20.0 parts of room temperature curing aliphatic polyamide was added to the reversible thermochromic epoxy ink and mixed with stirring to prepare a reversible thermochromic epoxy ink.
Curved screen printing is performed on the surface of the ceramic cup using a stainless steel 100 mesh screen plate using reversible thermochromic epoxy ink, and the material is heated and cured at 70°C for 60 minutes to form a reversible thermochromic layer, resulting in reversible thermochromic change. Got a sex cup.
The reversible thermochromic cup takes on a blue color when heated above 50°C.
When the reversible thermochromic cup is cooled to 35° C. and left to stand, the reversible thermochromic cup becomes colorless.
応用例4
実施例4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、蛍光顔料(ピンク色)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。
可逆熱変色性ミニチュア電車は32℃以上に加温すると紫色を呈する。
可逆熱変色性ミニチュア電車を24℃迄冷却した後、放置するとの前記可逆熱変色性ミニチュア電車はピンク色を呈する。
Application example 4
10.0 parts of microcapsule pigment encapsulating the reversible thermochromic composition prepared in Example 4, 1.0 part of fluorescent pigment (pink), 45.0 parts of 50% acrylic resin/xylene solution, 15.0 parts of xylene 1 part, 23.0 parts of methyl isobutyl ketone, and 6.0 parts of a polyisocyanate curing agent were stirred and mixed to prepare a reversible thermochromic spray paint.
A reversible thermochromic miniature train was obtained by spray painting the entire miniature train with a reversible thermochromic spray paint to form a reversible thermochromic layer.
The reversible thermochromic miniature train takes on a purple color when heated above 32°C.
When the reversible thermochromic miniature electric car is cooled to 24° C. and then left to stand, the reversible thermochromic miniature electric car exhibits a pink color.
応用例5
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、青色顔料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カーを得た。
可逆熱変色性ミニチュアカーは38℃以上に加温すると紫色を呈する。
可逆熱変色性ミニチュアカーを26℃迄冷却した後、放置するとの可逆熱変色性ミニチュアカーは青色を呈する。
Application example 5
10.0 parts of microcapsule pigment encapsulating the reversible thermochromic composition prepared in Example 7, 1.0 part of blue pigment, 45.0 parts of 50% acrylic resin/xylene solution, 15.0 parts of xylene, methyl isobutyl A reversible thermochromic spray paint was prepared by stirring and mixing in a vehicle consisting of 23.0 parts of ketone and 6.0 parts of a polyisocyanate curing agent.
A reversible thermochromic miniature car was obtained by spray painting the entire miniature train with a reversible thermochromic spray paint to form a reversible thermochromic layer.
The reversible thermochromic miniature car takes on a purple color when heated above 38°C.
When the reversible thermochromic miniature car is cooled to 26° C. and then left to stand, the reversible thermochromic miniature car exhibits a blue color.
応用例6
実施例5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、黄色顔料0.04部、12ナイロン樹脂(融点178℃)1000.0部、紫外線吸収剤10.0部を混合し、ヘンシェルミキサーで分散した後、押出成形機を用いて可逆熱変色性12ナイロン樹脂ペレット(可逆熱変色性成形用樹脂組成物)を得た。
可逆熱変色性成形用樹脂組成物を用いて溶融紡糸を行ない、成形体として可逆熱変色性フィラメントを得た。
フィラメントを用いて人形の頭に植毛を施した。
フィラメントは32℃以上に加温すると青色と黄色が混色となった緑色を呈する。
フィラメントを10℃迄冷却した後、放置するとの前記フィラメントは黄色を呈する。
Application example 6
50.0 parts of microcapsule pigment encapsulating the reversible thermochromic composition prepared in Example 5, 0.04 part of yellow pigment, 1000.0 parts of 12 nylon resin (melting point 178°C), 10.0 parts of ultraviolet absorber After mixing and dispersing with a Henschel mixer, reversible thermochromic 12 nylon resin pellets (reversible thermochromic molding resin composition) were obtained using an extruder.
A reversible thermochromic molding resin composition was melt-spun to obtain a reversible thermochromic filament as a molded article.
Hair was transplanted onto the doll's head using filament.
When the filament is heated above 32°C, it takes on a green color that is a mixture of blue and yellow.
After cooling the filament to 10° C., the filament assumes a yellow color when left to stand.
応用例7
実施例6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部を、アクリル酸エステル樹脂エマルジョン45.0部、消泡剤1.0部、希釈水23.0部からなるビヒクル中に混合し、180メッシュスクリーンで濾過して可逆熱変色性スプレー塗料を得た。
スプレー塗料をスプレーガン(口径0.6mm)に充填して白色布帛(支持体)の全面に塗装を施した後、乾燥させて可逆熱変色層を形成して可逆熱変色性布帛を得た。
布帛を縫製して、水着を作製した。
水着38℃以上に加温すると青色を呈する。
水着を20℃迄冷却した後、放置するとの前記水着は白色を呈する。
Application example 7
30.0 parts of the microcapsule pigment containing the reversible thermochromic composition prepared in Example 6 was mixed with 45.0 parts of acrylic ester resin emulsion, 1.0 part of antifoaming agent, and 23.0 parts of dilution water. Mixed into a vehicle and filtered through a 180 mesh screen to obtain a reversible thermochromic spray paint.
A spray gun (diameter 0.6 mm) was filled with the spray paint to coat the entire surface of a white fabric (support), and then dried to form a reversible thermochromic layer to obtain a reversible thermochromic fabric.
A swimsuit was made by sewing fabric.
When the swimsuit is heated above 38℃, it turns blue.
When the swimsuit is left to stand after being cooled to 20° C., the swimsuit takes on a white color.
応用例8
実施例8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。
シート上からSEBS製の摩擦具を用いて擦過して摩擦熱を発生させ、32℃以上に加温すると青色を呈する。
可逆熱変色性シートを5℃迄冷却した後、放置すると前記可逆熱変色性シートは白色を呈する。
Application example 8
50.0 parts of the microcapsule pigment containing the reversible thermochromic composition prepared in Example 8 was uniformly dispersed and mixed in 50.0 parts of a linseed oil-based offset ink vehicle to form a reversible thermochromic offset ink. Prepared.
Offset printing was performed on high-quality paper using the offset ink to form a reversible thermochromic layer to obtain a reversible thermochromic sheet.
The sheet is rubbed with a friction tool made of SEBS to generate frictional heat, and when heated to 32° C. or higher, it turns blue.
When the reversible thermochromic sheet is cooled to 5° C. and left to stand, the reversible thermochromic sheet exhibits a white color.
応用例9
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。
シート上から通電加熱具を用いて32℃以上に加温すると青色を呈する。
可逆熱変色性シートを24℃迄冷却した後、暫く放置すると可逆熱変色性シートは白色を呈する。
Application example 9
50.0 parts of the microcapsule pigment containing the reversible thermochromic composition prepared in Example 9 was uniformly dispersed and mixed in 50.0 parts of a linseed oil-based offset ink vehicle to form a reversible thermochromic offset ink. Prepared.
Offset printing was performed on high-quality paper using offset ink to form a reversible thermochromic layer to obtain a reversible thermochromic sheet.
When the sheet is heated to 32° C. or higher using an electric heating tool, it turns blue.
After the reversible thermochromic sheet is cooled to 24° C. and left for a while, the reversible thermochromic sheet exhibits a white color.
Claims (11)
(b)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フェニル酢酸エステル化合物と、
(c)前記(a)成分及び(b)成分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、脂環族炭化水素類及びハロゲン化炭化水素類からなる群から選ばれる化合物と、
(d)軟化点が5℃以上、且つ、質量平均分子量が200~10万のスチレン系化合物と
を含んでなり、消色状態からの加熱により発色状態となり、発色状態からの降温により消色状態となる可逆熱変色性組成物を内包してなる、可逆熱変色性マイクロカプセル顔料。
Rは、炭素数12~22の、直鎖又は分岐の、アルキル基を示し、
X、Y、及びZは、それぞれ独立に、水素または水酸基であり、それらのうち二つ又は三つが水酸基であり、残りは水素である) (a) an electron-donating color-forming organic compound;
(b) a hydroxyphenylacetate compound represented by the following general formula (1) as an electron-accepting compound;
(c) The reaction medium for reversibly causing the electron transfer reaction between the components (a) and (b) is selected from the group consisting of chain hydrocarbons, alicyclic hydrocarbons, and halogenated hydrocarbons. A compound that is
(d) Contains a styrene compound with a softening point of 5°C or higher and a mass average molecular weight of 200 to 100,000, which becomes a colored state by heating from a colorless state, and a colorless state by cooling from a colored state. A reversible thermochromic microcapsule pigment containing a reversible thermochromic composition.
R represents a linear or branched alkyl group having 12 to 22 carbon atoms,
X, Y, and Z are each independently hydrogen or a hydroxyl group, two or three of them are hydroxyl groups, and the rest are hydrogen)
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