JPWO2018143473A1 - Temperature-responsive color material - Google Patents
Temperature-responsive color material Download PDFInfo
- Publication number
- JPWO2018143473A1 JPWO2018143473A1 JP2018566168A JP2018566168A JPWO2018143473A1 JP WO2018143473 A1 JPWO2018143473 A1 JP WO2018143473A1 JP 2018566168 A JP2018566168 A JP 2018566168A JP 2018566168 A JP2018566168 A JP 2018566168A JP WO2018143473 A1 JPWO2018143473 A1 JP WO2018143473A1
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- Japan
- Prior art keywords
- pigment
- organic
- compound
- dye
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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Classifications
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- 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/12—Obtaining compounds having alkyl radicals, or alkyl radicals substituted by hetero atoms, bound to the phthalocyanine skeleton
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Abstract
【解決課題】新規な温度応答性色材を提供すること。【解決手段】(i)室温付近に融点等の転移点を有する有機化合物、及び(ii)少なくとも1種の顔料、有機色素又は赤外線吸収色素を含み、前記有機化合物、及び前記顔料、有機色素又は赤外線吸収色素はカプセルにより内包されている色材。【選択図】なしTo provide a novel temperature-responsive color material. (I) an organic compound having a transition point such as a melting point near room temperature, and (ii) at least one pigment, organic dye or infrared absorbing dye, the organic compound, and the pigment, organic dye or Infrared absorbing pigment is a color material that is encapsulated in capsules. [Selection figure] None
Description
本発明は、温度により光学特性が変化する色材に関する。 The present invention relates to a color material whose optical characteristics change with temperature.
温度により光学特性、即ち各波長における吸収、反射率、透過率が変化することをサーモクロミズムと呼ぶ。有機・無機化合物を問わずサーモクロミック特性を有する物質は多く知られており、分子構造の変化、コンフォメーションの変化等様々なタイプのものが存在する。 The change in optical characteristics, that is, absorption, reflectance, and transmittance at each wavelength depending on temperature is called thermochromism. Many substances having thermochromic properties are known regardless of whether they are organic or inorganic compounds, and there are various types such as changes in molecular structure and changes in conformation.
カプセル内包型ロイコ染料は、ある温度領域で分子構造の変化を起こすサーモクロミック材料として知られており(非特許文献1)、市販されている。しかしながら、カプセル内包型ロイコ染料のような分子構造が変化するタイプの材料は長時間紫外線や高温に曝されると退色するという問題がある。 Encapsulated leuco dyes are known as thermochromic materials that cause a change in molecular structure in a certain temperature range (Non-Patent Document 1) and are commercially available. However, there is a problem that materials of a type whose molecular structure changes, such as an encapsulated leuco dye, fades when exposed to ultraviolet rays or high temperatures for a long time.
近年、サーモクロミック材料の新たな応用として、反射材との組み合わせによる温度可変型遮熱効果が報告されている(非特許文献2)。このシステムでは、高温時には吸収帯が消失し、太陽光を反射することでさらなる昇温を防ぐ一方、低温時には吸収帯が発現し、太陽光を吸収することで昇温することができる。このサーモクロミック材料を用いたシステムでは、太陽光吸収率の変化、耐光性及び耐熱性が重要となる。 In recent years, as a new application of a thermochromic material, a temperature-variable heat shielding effect by a combination with a reflective material has been reported (Non-patent Document 2). In this system, the absorption band disappears at a high temperature, and further temperature rise is prevented by reflecting sunlight, while the absorption band appears at a low temperature and the temperature can be raised by absorbing sunlight. In a system using this thermochromic material, changes in sunlight absorption rate, light resistance and heat resistance are important.
フタロシアニン錯体は、低濃度溶液中では単量体として存在し、700nm付近にシャープなQ吸収帯を有する。一方、固体(すべての分子が会合している)状態では、フタロシアニン錯体間の強いπ−π相互作用により、Q吸収帯はブロードになる(図1)。このような劇的なスペクトル変化を、室温付近の温度変化により達成できれば、新規な温度可変型遮熱材料へ発展することが期待できる。しかしながら、このような温度可変型遮熱材料に用いることができる有効な色材は開発されていなかった。 The phthalocyanine complex exists as a monomer in a low concentration solution, and has a sharp Q absorption band in the vicinity of 700 nm. On the other hand, in the solid state (all molecules are associated), the Q absorption band becomes broad due to the strong π-π interaction between the phthalocyanine complexes (FIG. 1). If such a dramatic spectral change can be achieved by a temperature change near room temperature, it can be expected to develop into a new temperature-variable heat shielding material. However, an effective color material that can be used for such a temperature-variable heat shielding material has not been developed.
本発明は、新規な温度応答性色材を提供することを目的とする。より具体的には、本発明は、化学反応に伴う分子構造が変化するタイプではなく、分子の会合による光吸収の変化を用いた温度応答性(サーモクロミック)色材を提供することを目的とする。 An object of the present invention is to provide a novel temperature-responsive color material. More specifically, an object of the present invention is to provide a temperature responsive (thermochromic) coloring material using a change in light absorption due to association of molecules, not a type in which the molecular structure accompanying a chemical reaction changes. To do.
本発明者らは、分子の会合状態の変化により光吸収が変化するフタロシアニン錯体等の色素に着目し、その光吸収の変化を制御する方法を検討したところ、室温付近に相転移温度を有する液晶性分子や有機溶媒中にフタロシアニン錯体を混合することにより、フタロシアニン錯体等のサーモクロミック特性を制御できることを見出した。即ち、液晶性分子や有機溶媒が固体状態にある場合はフタロシアニン錯体等の色素も分子会合しているためブロードなQ吸収帯を有するが、液晶性分子等が液晶又は液体状態になるとフタロシアニン錯体等は単量体として存在し、シャープなQ吸収帯を有する。
しかしながら、液晶性分子や有機溶媒が液晶又は液体状態になると、サーモクロミック色材として安定した形態を保持することが困難となるため、実用的に使用する上で制約があった。The present inventors focused on dyes such as phthalocyanine complexes whose light absorption changes due to changes in the association state of the molecules, and studied a method for controlling the change in light absorption. As a result, liquid crystals having a phase transition temperature near room temperature. The present inventors have found that thermochromic properties of phthalocyanine complexes and the like can be controlled by mixing phthalocyanine complexes in organic molecules and organic solvents. That is, when a liquid crystal molecule or an organic solvent is in a solid state, a dye such as a phthalocyanine complex is also associated with a molecule, and thus has a broad Q absorption band. However, when a liquid crystal molecule or the like is in a liquid crystal or liquid state, the phthalocyanine complex Exists as a monomer and has a sharp Q absorption band.
However, when liquid crystalline molecules or organic solvents are in a liquid crystal or liquid state, it is difficult to maintain a stable form as a thermochromic color material, and thus there is a limitation in practical use.
そこで、本発明者らは鋭意検討したところ、室温付近に相転移温度を有する液晶性分子や有機溶媒と、フタロシアニン錯体等の分子の会合状態の変化により光吸収が変化する顔料、有機色素又は赤外線吸収色素との混合物をカプセル化することにより、サーモクロミック特性を効率的に制御できる色材を提供できることを見出し、本発明を完成した。
更に、本発明者らは検討したところ、室温付近に相転移温度を有する脂肪酸、蝋、油脂類、イオン液体、天然高分子、合成高分子、リン脂質等の有機化合物中にフタロシアニン錯体を混合することにより、フタロシアニン錯体等のサーモクロミック特性を制御できることを見出した。そして、これら有機化合物と、フタロシアニン錯体等の分子の会合状態の変化により光吸収が変化する顔料、有機色素又は赤外線吸収色素との混合物をカプセル化することにより、サーモクロミック特性を効率的に制御できる色材を提供できることを見出し、本発明を完成した。
更に、本発明者らは、カプセル化した色材に特定のカチオンを含有させることにより、水難溶性の色材が得られることを見出した。Therefore, the present inventors have conducted intensive studies and have found that pigments, organic dyes, or infrared rays whose light absorption changes due to changes in the association state of liquid crystal molecules or organic solvents having a phase transition temperature near room temperature and molecules such as phthalocyanine complexes. The inventors have found that a colorant capable of efficiently controlling thermochromic properties can be provided by encapsulating a mixture with an absorbing dye, thereby completing the present invention.
Furthermore, the present inventors have examined that a phthalocyanine complex is mixed in an organic compound such as fatty acid, wax, fats and oils, ionic liquid, natural polymer, synthetic polymer, phospholipid having a phase transition temperature around room temperature. Thus, it was found that thermochromic properties such as phthalocyanine complex can be controlled. The thermochromic characteristics can be controlled efficiently by encapsulating a mixture of these organic compounds and pigments, organic dyes or infrared absorbing dyes whose light absorption changes due to changes in the association state of molecules such as phthalocyanine complexes. The present inventors have found that a color material can be provided and completed the present invention.
Furthermore, the present inventors have found that a poorly water-soluble color material can be obtained by adding a specific cation to the encapsulated color material.
即ち、本発明は、
[1](i)少なくとも1種の室温付近に融点等の転移点を有する有機化合物、及び
(ii)少なくとも1種の顔料、有機色素又は赤外線吸収色素
を含み、前記有機化合物、及び前記顔料、有機色素又は赤外線吸収色素はカプセルにより内包されている色材。
[2]前記顔料、有機色素又は赤外線吸収色素は、分子の会合状態の変化により光の吸収スペクトルが変化する、[1]に記載の色材。
[3]前記有機化合物は、液晶性化合物、有機溶媒、脂肪酸、蝋、油脂類、イオン液体、天然高分子、合成高分子、リン脂質又はこれらの組合せから選択される、[1]又は[2]に記載の色材。
[4]前記カプセルは、ミセル又は脂質二重膜(リポソーム)からなる、[1]〜[3]のいずれか1項に記載の色材。
[5](i)少なくとも1種の室温付近に融点等の転移点を有する脂肪酸、及び
(ii)少なくとも1種の顔料、有機色素又は赤外線吸収色素
を含み、前記脂肪酸、及び前記顔料、有機色素又は赤外線吸収色素は、当該脂肪酸の金属塩により形成されたミセルにより内包されている色材。
[6][1]〜[5]のいずれか1項に記載の色材を含有する溶液。
[7][1]〜[5]のいずれか1項に記載の色材を含有する分散液。
[8](i)少なくとも1種の室温付近に融点等の転移点を有する有機化合物、及び
(ii)少なくとも1種の顔料、有機色素又は赤外線吸収色素
を含み、前記有機化合物、及び前記顔料、有機色素又は赤外線吸収色素はミセル又はリポソームからなるカプセルにより内包されており、前記ミセル又はリポソームの表面においてカチオンが結合又は付着している、色材。
[9]前記顔料、有機色素又は赤外線吸収色素は、分子の会合状態の変化により光の吸収スペクトルが変化する、[8]に記載の色材。
[10]前記有機化合物は、液晶性化合物、有機溶媒、脂肪酸、蝋、油脂類、イオン液体、天然高分子、合成高分子、リン脂質又はこれらの組合せから選択される、[8]又は[9]に記載の色材。
[11]前記液晶性化合物は、4−シアノ−4’−ヘプチルビフェニル、4−シアノ−4’−オクチロキシビフェニル、4−シアノ−4’−ペンチルビフェニル、4−シアノ−4’−ヘキシルビフェニル、4−シアノ−4’−n−オクチルビフェニル、4−(トランス−4−アミルシクロヘキシル)ベンゾニトリル、4−(トランス−4−エチルシクロヘキシル)ベンゾニトリル、(S)−4−シアノ−4’−(2―メチルブチル)ビフェニル、3、4,5−トリフルオロ−4’−(トランス−4−プロピルシクロヘキシル)ビフェニル、4’−エトキシベンジリデン−4−ブチルアニリン、TK−LQ 3858、TK−LQ 2040、リノール酸コレステロール、コレステロールオレイルカルボナート、リン脂質及びこれらの2以上の混合物からなる群から選択される、[10]に記載の色材。
[12]前記有機溶媒は、シクロヘキサノール、グリセロール、p−キシレン、ジフェニルメタン、1,3−ジメトキシベンゼン、ジフェニルエーテル、アセトフェノン、プロピオフェノン、安息香酸ベンジル、p−クロロトルエン、1,2,4−トリクロロベンゼン、及びこれら2以上の混合溶媒からなる群から選択される、[10]に記載の色材。
[13]前記脂肪酸は、オクタン酸、ノナン酸、デカン酸、ウンデカノン酸、ドデカン酸、トリデカノン酸、ヘキサデセ−9−エン酸、(9Z)−オクタデセ−9エン酸、(9E)−9−オクタデセン酸、(9E,11E,13Z)−9,11,13−オクタデカトリエン酸、(13Z)−13−ドコセン酸、(Z)−テトラコセ−15−エン酸及びこれらの2以上の混合物からなる群から選択される、[10]に記載の色材。
[14]前記蝋は、パラフィンワックス、ワセリン、ラノリン、木蝋、白蝋、蜜蝋、鯨蝋及びこれらの2以上の混合物からなる群から選択される、[10]に記載の色材。
[15]前記油脂類は、パーム油、ヤシ油、ラード、牛脂、カカオバター、パームバター、アーモンドバター、マカダミアバター、ヘンプシードバター、ホホバター、コーヒーバター、シアバター、大豆バター、パーム硬化油、牛脂硬化油、ラード硬化油、大豆硬化油、菜種硬化油及びこれらの2以上の混合物からなる群から選択される、[10]に記載の色材。
[16]前記顔料は、フタロシアニン系顔料、酸化チタン、カーボンブラック、酸化鉄、黄鉛又はウルトラマリンから選択される少なくとも1つである、[8]〜[15]のいずれか1項に記載の色材。
[17]前記有機色素は、アゾ系化合物、キノン系化合物、トリアリールメタン系化合物、シアニン系化合物、フタロシアニン系化合物又はインジゴ系化合物から選択される少なくとも1つである、[8]〜[16]のいずれか1項に記載の色材。
[18]前記赤外線吸収色素は、シアニン系化合物、フタロシアニン系化合物、ナフタロシアニン系化合物、アントラコシアニン系化合物、アゾ系化合物、キノン系化合物又はスクアリウム系化合物から選択される少なくとも1つである、[8]〜[17]のいずれか1項に記載の色材。
[19]前記ミセルは、スルホン基又はカルボキシル基を有する界面活性剤により形成されている、[8]〜[18]のいずれか1項に記載の色材。
[20]前記カチオンは、バリウムイオン、カルシウムイオン、マグネシウムイオン、亜鉛イオン、鉛イオン、銅イオン、水銀イオン、銀イオン又はストロンチウムイオンである、[8]〜[19]のいずれか1項に記載の色材。
[21](i)少なくとも1種の室温付近に融点等の転移点を有する脂肪酸、及び
(ii)少なくとも1種の顔料、有機色素又は赤外線吸収色素
を含み、前記脂肪酸、及び前記顔料、有機色素又は赤外線吸収色素は、当該脂肪酸の金属塩により形成されたミセルにより内包されており、前記ミセルの表面においてカチオンが結合又は付着している、色材。
[22]水に難溶性である[8]〜[21]のいずれか1項に記載の色材。
[23](1)室温付近に融点等の転移点を有する有機化合物、及び、少なくとも1種の分子の会合状態の変化により光吸収が変化する顔料、有機色素又は赤外線吸収色素を含む組成物を形成する工程、
(2)前記組成物、及び界面活性剤又はリン脂質を水に添加して水溶液を得る工程、及び
(3)前記水溶液に、カチオンを生成する化合物を添加する工程
を含む、色材を調製する方法。
[24](1)室温付近に融点等の転移点を有する有機化合物、少なくとも1種の分子の会合状態の変化により光吸収が変化する顔料、有機色素又は赤外線吸収色素、及び界面活性剤又はリン脂質を水に添加して水溶液を得る工程、及び
(2)前記水溶液に、カチオンを生成する化合物を添加する工程
を含む、色材を調製する方法。
[25][8]〜[22]のいずれか1項に記載の色材、及び、水、有機溶媒又はこれらの混合物を含む分散液。
[26][8]〜[22]のいずれか1項に記載の色材;水、有機溶媒又はこれらの混合物;及び樹脂を含む塗料組成物。
[27]反射材、及び当該反射材の上に設けられた[8]〜[22]のいずれか1項に記載の色材を含む層を備える遮熱材。
を、提供するものである。That is, the present invention
[1] (i) at least one organic compound having a transition point such as a melting point near room temperature, and (ii) at least one pigment, organic dye or infrared absorbing dye, the organic compound, and the pigment, An organic dye or an infrared absorbing dye is a coloring material encapsulated in a capsule.
[2] The color material according to [1], wherein the pigment, the organic dye, or the infrared-absorbing dye changes a light absorption spectrum due to a change in an association state of molecules.
[3] The organic compound is selected from liquid crystal compounds, organic solvents, fatty acids, waxes, fats and oils, ionic liquids, natural polymers, synthetic polymers, phospholipids, or combinations thereof [1] or [2 ] The coloring material as described in.
[4] The color material according to any one of [1] to [3], wherein the capsule is made of a micelle or a lipid bilayer (liposome).
[5] (i) at least one fatty acid having a transition point such as a melting point near room temperature, and (ii) at least one pigment, organic dye or infrared absorbing dye, the fatty acid, and the pigment or organic dye Alternatively, the infrared absorbing dye is a coloring material that is encapsulated in micelles formed from a metal salt of the fatty acid.
[6] A solution containing the color material according to any one of [1] to [5].
[7] A dispersion containing the color material according to any one of [1] to [5].
[8] (i) at least one organic compound having a transition point such as a melting point near room temperature, and (ii) at least one pigment, organic dye or infrared absorbing dye, the organic compound, and the pigment, A coloring material in which an organic dye or an infrared-absorbing dye is encapsulated in a capsule made of micelles or liposomes, and a cation is bonded or adhered to the surface of the micelles or liposomes.
[9] The colorant according to [8], wherein the pigment, the organic dye, or the infrared absorbing dye has a light absorption spectrum that changes due to a change in an association state of molecules.
[10] The organic compound is selected from liquid crystal compounds, organic solvents, fatty acids, waxes, fats and oils, ionic liquids, natural polymers, synthetic polymers, phospholipids, or combinations thereof [8] or [9 ] The coloring material as described in.
[11] The liquid crystalline compound includes 4-cyano-4′-heptylbiphenyl, 4-cyano-4′-octyloxybiphenyl, 4-cyano-4′-pentylbiphenyl, 4-cyano-4′-hexylbiphenyl, 4-cyano-4′-n-octylbiphenyl, 4- (trans-4-amylcyclohexyl) benzonitrile, 4- (trans-4-ethylcyclohexyl) benzonitrile, (S) -4-cyano-4 ′-( 2-methylbutyl) biphenyl, 3,4,5-trifluoro-4 ′-(trans-4-propylcyclohexyl) biphenyl, 4′-ethoxybenzylidene-4-butylaniline, TK-LQ 3858, TK-LQ 2040, linole Made of acid cholesterol, cholesterol oleyl carbonate, phospholipids and mixtures of two or more thereof The color material according to [10], which is selected from the group.
[12] The organic solvent is cyclohexanol, glycerol, p-xylene, diphenylmethane, 1,3-dimethoxybenzene, diphenyl ether, acetophenone, propiophenone, benzyl benzoate, p-chlorotoluene, 1,2,4-tri The color material according to [10], which is selected from the group consisting of chlorobenzene and a mixed solvent of two or more of these.
[13] The fatty acid is octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, hexadec-9-enoic acid, (9Z) -octadece-9-enoic acid, (9E) -9-octadecenoic acid , (9E, 11E, 13Z) -9,11,13-octadecatrienoic acid, (13Z) -13-docosenoic acid, (Z) -tetracoce-15-enoic acid and mixtures of two or more thereof The color material according to [10], which is selected.
[14] The color material according to [10], wherein the wax is selected from the group consisting of paraffin wax, petrolatum, lanolin, wood wax, white wax, beeswax, spermaceti and a mixture of two or more thereof.
[15] The fats and oils are palm oil, palm oil, lard, beef tallow, cacao butter, palm butter, almond butter, macadamia butter, hemp seed butter, jojoba butter, coffee butter, shea butter, soybean butter, palm hardened oil, beef tallow The coloring material according to [10], which is selected from the group consisting of hydrogenated oil, lard hardened oil, soybean hardened oil, rapeseed hardened oil, and a mixture of two or more thereof.
[16] The pigment according to any one of [8] to [15], wherein the pigment is at least one selected from phthalocyanine pigments, titanium oxide, carbon black, iron oxide, chrome lead, and ultramarine. Color material.
[17] The organic dye is at least one selected from an azo compound, a quinone compound, a triarylmethane compound, a cyanine compound, a phthalocyanine compound, or an indigo compound, [8] to [16] The color material according to any one of the above.
[18] The infrared absorbing dye is at least one selected from a cyanine compound, a phthalocyanine compound, a naphthalocyanine compound, an anthracocyanine compound, an azo compound, a quinone compound, or a squalium compound. The color material according to any one of [8] to [17].
[19] The color material according to any one of [8] to [18], wherein the micelle is formed of a surfactant having a sulfone group or a carboxyl group.
[20] The cation according to any one of [8] to [19], wherein the cation is barium ion, calcium ion, magnesium ion, zinc ion, lead ion, copper ion, mercury ion, silver ion, or strontium ion. Color material.
[21] (i) at least one fatty acid having a transition point such as a melting point near room temperature, and (ii) at least one pigment, organic dye or infrared absorbing dye, the fatty acid, and the pigment or organic dye Alternatively, the infrared absorbing dye is a colorant that is encapsulated in micelles formed of a metal salt of the fatty acid, and a cation is bonded or adhered to the surface of the micelle.
[22] The color material according to any one of [8] to [21], which is hardly soluble in water.
[23] (1) A composition comprising an organic compound having a transition point such as a melting point near room temperature, and a pigment, an organic dye or an infrared-absorbing dye whose light absorption changes due to a change in the association state of at least one molecule. Forming step,
(2) A coloring material is prepared, including the step of adding the composition and a surfactant or phospholipid to water to obtain an aqueous solution, and (3) adding a compound that generates a cation to the aqueous solution. Method.
[24] (1) An organic compound having a transition point such as a melting point near room temperature, a pigment whose organic light absorption changes due to a change in the association state of at least one molecule, an organic dye or an infrared absorbing dye, and a surfactant or phosphorus A method of preparing a coloring material, comprising: adding a lipid to water to obtain an aqueous solution; and (2) adding a compound that generates a cation to the aqueous solution.
[25] A dispersion containing the color material according to any one of [8] to [22] and water, an organic solvent, or a mixture thereof.
[26] A coating composition comprising the colorant according to any one of [8] to [22]; water, an organic solvent or a mixture thereof; and a resin.
[27] A heat shielding material comprising a reflective material and a layer containing the color material according to any one of [8] to [22] provided on the reflective material.
Is provided.
本発明により、化学反応に伴う分子構造が変化するタイプではなく、分子の会合による光吸収の変化を用いたサーモクロミック色材を提供することが可能である。本発明のサーモクロミック材料は、従来のカプセル内包型染料のような化学変化タイプのサーモクロミック材料に比べて、熱や光による退色を抑制することが可能である。 According to the present invention, it is possible to provide a thermochromic coloring material using a change in light absorption due to association of molecules, not a type in which a molecular structure accompanying a chemical reaction changes. The thermochromic material of the present invention can suppress discoloration due to heat or light as compared with a chemical change type thermochromic material such as a conventional encapsulated dye.
本発明の1つの実施態様は、(i)少なくとも1種の室温付近に融点等の転移点を有する有機化合物、及び(ii)少なくとも1種の顔料、有機色素又は赤外線吸収色素を含み、前記有機化合物、及び前記顔料又は有機色素はカプセルにより内包されている色材である(以下「実施態様1」とも言う)。
One embodiment of the present invention comprises (i) at least one organic compound having a transition point such as a melting point near room temperature, and (ii) at least one pigment, organic dye or infrared absorbing dye, The compound, and the pigment or organic coloring matter are color materials encapsulated in capsules (hereinafter also referred to as “
本発明に用いることができる顔料、有機色素又は赤外線吸収色素は、好ましくは、分子の会合状態の変化により光の吸収スペクトルが変化する顔料、有機色素又は赤外線吸収色素である。具体的には、顔料、有機色素又は赤外線吸収色素が固体状態にある場合と、溶液中にある場合とで光の吸収スペクトルが変化する顔料、有機色素又は赤外線吸収色素である。 The pigment, organic dye or infrared absorbing dye that can be used in the present invention is preferably a pigment, organic dye or infrared absorbing dye whose absorption spectrum of light changes due to a change in the association state of molecules. Specifically, it is a pigment, organic dye or infrared absorbing dye whose absorption spectrum of light changes depending on whether the pigment, organic dye or infrared absorbing dye is in a solid state or in a solution.
本発明に用いることができる顔料としては上記のような特性を示す顔料であればその種類は特に制限されないが、有機顔料としては、例えば、フタロシアニン系顔料等、無機顔料としては、酸化チタン、カーボンブラック、酸化鉄、黄鉛、ウルトラマリン等が挙げられる。フタロシアニン系顔料としては、中心に金属が入っているもの(フタロシアニン錯体)、入っていないものの何れも用いることができる。 The type of the pigment that can be used in the present invention is not particularly limited as long as it exhibits the above-mentioned characteristics. Examples of the organic pigment include phthalocyanine pigments, and examples of the inorganic pigment include titanium oxide and carbon. Black, iron oxide, yellow lead, ultramarine, etc. are mentioned. As the phthalocyanine pigment, any of those containing a metal in the center (phthalocyanine complex) and those containing no metal can be used.
フタロシアニン錯体としては、以下の構造を有するt−BuSiPc(OH)2(シリコン2,9,16,23−テトラ−tert−ブチル−29H,31H−フタロシアニンジヒドロキシド)が特に好ましい。
As the phthalocyanine complex, t-BuSiPc (OH) 2 (
また、本発明に用いることができる有機色素としては上記のような特性を示す有機色素であればその種類は特に制限されないが、例えば、アゾ系化合物、キノン系化合物、トリアリールメタン系化合物、シアニン系化合物、フタロシアニン系化合物、インジゴ系化合物等が挙げられる。 The organic dye that can be used in the present invention is not particularly limited as long as it is an organic dye exhibiting the above-mentioned characteristics. For example, azo compounds, quinone compounds, triarylmethane compounds, cyanine Compounds, phthalocyanine compounds, indigo compounds and the like.
本発明に用いることができる赤外線吸収色素としては、上記のような特性を示す赤外線吸収色素であればその種類は特に制限されないが、例えば、シアニン系化合物、フタロシアニン系化合物、ナフタロシアニン系化合物、アントラコシアニン系化合物、アゾ系化合物、キノン系化合物、スクアリウム系化合物等が挙げられる。
なお、本明細書においては、赤外線吸収色素には近赤外線吸収色素も含まれる。The infrared absorbing dye that can be used in the present invention is not particularly limited as long as it is an infrared absorbing dye exhibiting the above-mentioned characteristics. For example, cyanine compounds, phthalocyanine compounds, naphthalocyanine compounds, anthra Examples include cocyanine compounds, azo compounds, quinone compounds, squalium compounds, and the like.
In the present specification, the infrared absorbing dye includes a near infrared absorbing dye.
本発明の色材は、2種以上の顔料、有機色素又は赤外線吸収色素を含んでもよく、また、顔料、有機色素又は赤外線吸収色素から任意に選択される2以上の組み合わせを含んでもよい。 The coloring material of the present invention may contain two or more kinds of pigments, organic dyes or infrared absorbing dyes, and may contain a combination of two or more arbitrarily selected from pigments, organic dyes or infrared absorbing dyes.
室温付近に融点等の転移点を有する有機化合物は、室温付近に融点等の転移点を有する液晶性化合物、有機溶媒、脂肪酸、蝋、油脂類、イオン液体、天然高分子、合成高分子、リン脂質又はこれらの組合せから選択される。
ここで、転移点としては、融点が挙げられる。Organic compounds having a transition point such as a melting point near room temperature include liquid crystalline compounds having a transition point such as a melting point near room temperature, organic solvents, fatty acids, waxes, fats and oils, ionic liquids, natural polymers, synthetic polymers, phosphorus Selected from lipids or combinations thereof.
Here, the transition point includes the melting point.
本発明で使用できる液晶性化合物は、室温付近で相転移する液晶性化合物、具体的には、0℃〜50℃に融点等の転移点を有する液晶性化合物であれば特に制限なく用いることができるが、4−シアノ−4’−ヘプチルビフェニル(7CB)、4−シアノ−4’−オクチロキシビフェニル(8OCB)、4−シアノ−4’−ペンチルビフェニル、4−シアノ−4’−ヘキシルビフェニル、4−シアノ−4’−n−オクチルビフェニル、4−(トランス−4−アミルシクロヘキシル)ベンゾニトリル、4−(トランス−4−エチルシクロヘキシル)ベンゾニトリル、(S)−4−シアノ−4’−(2―メチルブチル)ビフェニル、3、4,5−トリフルオロ−4’−(トランス−4−プロピルシクロヘキシル)ビフェニル、4’−エトキシベンジリデン−4−ブチルアニリン、TK−LQ 3858、TK−LQ 2040、リノール酸コレステロール、コレステロールオレイルカルボナート、リン脂質等が挙げられる。
リン脂質としては、例えば、0℃〜50℃に融点等の転移点を有するホスファチジン酸(例えば、ジミリストイルホスファチジルコリン、ジパルミトイルホスファチジルコリン、ジステアリルホスファチジルコリン等)、ホスファチジルエタノールアミン、ホスファチジルコリン、ホスファチジルセリン、ホスファチジルグリセロール等が挙げられる。
液晶性化合物は、これらの2以上の混合物を用いることもできる。The liquid crystalline compound that can be used in the present invention is not particularly limited as long as it is a liquid crystalline compound that undergoes a phase transition near room temperature, specifically, a liquid crystalline compound having a transition point such as a melting point at 0 ° C. to 50 ° C. 4-cyano-4′-heptylbiphenyl (7CB), 4-cyano-4′-octyloxybiphenyl (8OCB), 4-cyano-4′-pentylbiphenyl, 4-cyano-4′-hexylbiphenyl, 4-cyano-4′-n-octylbiphenyl, 4- (trans-4-amylcyclohexyl) benzonitrile, 4- (trans-4-ethylcyclohexyl) benzonitrile, (S) -4-cyano-4 ′-( 2-Methylbutyl) biphenyl, 3,4,5-trifluoro-4 ′-(trans-4-propylcyclohexyl) biphenyl, 4′-ethoxybenzylidene- - butyl aniline, TK-LQ 3858, TK-LQ 2040, cholesterol linoleate, cholesterol oleyl carbonate, phospholipids and the like.
Examples of the phospholipid include phosphatidic acid having a transition point such as a melting point at 0 ° C. to 50 ° C. (eg, dimyristoyl phosphatidylcholine, dipalmitoylphosphatidylcholine, distearyl phosphatidylcholine, etc.), phosphatidylethanolamine, phosphatidylcholine, phosphatidylserine, phosphatidylglycerol. Etc.
As the liquid crystalline compound, a mixture of two or more of these may be used.
本発明で使用できる有機溶媒は、室温付近で相転移する有機溶媒、具体的には、0℃〜50℃に融点等の転移点を有する有機溶媒であれば特に制限なく用いることができるが、例えば、シクロヘキサノール、グリセロール、p−キシレン、ジフェニルメタン、1,3−ジメトキシベンゼン、ジフェニルエーテル、アセトフェノン、プロピオフェノン、安息香酸ベンジル、p−クロロトルエン、1,2,4−トリクロロベンゼン等が挙げられる。有機溶媒としては、これら2以上からなる混合溶媒も用いることができ、例えば、シクロヘキサノールとグリセロールの混合溶媒等を好適に用いることができる。 The organic solvent that can be used in the present invention can be used without particular limitation as long as it is an organic solvent that undergoes a phase transition near room temperature, specifically, an organic solvent having a transition point such as a melting point at 0 ° C. to 50 ° C. Examples include cyclohexanol, glycerol, p-xylene, diphenylmethane, 1,3-dimethoxybenzene, diphenyl ether, acetophenone, propiophenone, benzyl benzoate, p-chlorotoluene, 1,2,4-trichlorobenzene, and the like. As the organic solvent, a mixed solvent composed of two or more of these can also be used. For example, a mixed solvent of cyclohexanol and glycerol can be suitably used.
本発明で使用できる脂肪酸は、室温付近で相転移する脂肪酸、具体的には、0℃〜50℃に融点等の転移点を有する脂肪酸であれば特に制限なく用いることができるが、例えば、オクタン酸、ノナン酸、デカン酸、ウンデカノン酸、ドデカン酸、トリデカノン酸、ヘキサデセ-9-エン酸、(9Z)-オクタデセ-9エン酸、(9E)−9−オクタデセン酸、(9E,11E,13Z)−9,11,13−オクタデカトリエン酸、(13Z)−13−ドコセン酸、(Z)−テトラコセ−15−エン酸及びこれらの2以上の混合物を用いることができる。 The fatty acid that can be used in the present invention can be used without particular limitation as long as it is a fatty acid that undergoes a phase transition near room temperature, specifically, a fatty acid having a transition point such as a melting point at 0 ° C to 50 ° C. Acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, hexadec-9-enoic acid, (9Z) -octadedec-9-enoic acid, (9E) -9-octadecenoic acid, (9E, 11E, 13Z) -9,11,13-octadecatrienoic acid, (13Z) -13-docosenoic acid, (Z) -tetracoce-15-enoic acid and mixtures of two or more thereof can be used.
本発明で使用できる蝋は、室温付近で相転移する蝋、具体的には、0℃〜50℃に融点等の転移点を有する蝋であれば特に制限なく用いることができるが、例えば、パラフィンワックス、ワセリン、ラノリン、木蝋、白蝋、蜜蝋、鯨蝋及びこれらの2以上の混合物からなる群から選択することができる。 The wax that can be used in the present invention can be used without particular limitation as long as it undergoes a phase transition near room temperature, specifically, a wax having a transition point such as a melting point at 0 ° C to 50 ° C. It can be selected from the group consisting of wax, petrolatum, lanolin, wood wax, white wax, beeswax, spermaceti and mixtures of two or more thereof.
本発明で使用できる油脂類は、室温付近で相転移する油脂類、具体的には、0℃〜50℃に融点等の転移点を有する油脂類であれば特に制限なく用いることができるが、例えば、パーム油、ヤシ油、散水添馬油、ラード、牛脂、カカオバター、パームバター、アーモンドバター、マカダミアバター、ヘンプシードバター、ホホバター、コーヒーバター、シアバター、大豆バター、マカダミアナッツバター、アサイーバター、アボカドーバター、アルガンバター、オリーブバター、オレンジバター、カモミールバター、クランベリーバター、ザクロバター、タンジェリンバター、ツクシバター、パンプキンシードバター、ビスタチオバター、ブラジルナッツバター、ブルーベリーバター、モノイバター、ライムバター、ラベンダーバター、レモンバター、ココナッツバター、コクムバター、マンゴバター、サラソウジュバター、アロエバター、ムルムルバター、ツクマバター、クパスバター、パーム硬化油、牛脂硬化油、ラード硬化油、大豆硬化油、菜種硬化油、オーストリッチオイル等、及びこれらの2以上の混合物からなる群から選択される。上記の油脂類の中でも、パーム油、ヤシ油、ラード、牛脂、カカオバター、パームバター、アーモンドバター、マカダミアバター、ヘンプシードバター、ホホバター、コーヒーバター、シアバター、大豆バター、パーム硬化油、牛脂硬化油、ラード硬化油、大豆硬化油、菜種硬化油及びこれらの2以上の混合物が、入手がし易く好適に用いることができる。 The oils and fats that can be used in the present invention can be used without particular limitation as long as they are oils and fats that undergo phase transition near room temperature, specifically, oils and fats having a transition point such as a melting point at 0 ° C to 50 ° C. For example, palm oil, palm oil, sprinkled horse oil, lard, beef tallow, cacao butter, palm butter, almond butter, macadamia butter, hemp seed butter, hojo butter, coffee butter, shea butter, soy butter, macadamia nut butter, acai butter , Avocado butter, Argan butter, Olive butter, Orange butter, Chamomile butter, Cranberry butter, Pomegranate butter, Tangerine butter, Tsukushi butter, Pumpkin seed butter, Vista butter, Brazil nut butter, Blueberry butter, Monoi butter, Lime butter, Lavender butter , Remo Butter, coconut butter, coconut butter, mango butter, salamander butter, aloe butter, murumuru butter, tsukuma butter, cupas butter, palm hardened oil, beef fat hardened oil, lard hardened oil, hardened soybean oil, rapeseed hardened oil, ostrich oil etc., and Selected from the group consisting of a mixture of two or more of these. Among the above oils and fats, palm oil, palm oil, lard, beef tallow, cacao butter, palm butter, almond butter, macadamia butter, hemp seed butter, jojoba, coffee butter, shea butter, soy butter, palm hardened oil, beef fat cured Oil, lard hardened oil, soybean hardened oil, rapeseed hardened oil and a mixture of two or more thereof are easily available and can be suitably used.
本発明で使用できるイオン液体は、室温付近で相転移するイオン液体、具体的には、0℃〜50℃に融点等の転移点を有するイオン液体であれば特に制限なく用いることができるが、例えば、N,N,N−トリメチル−N−プロピルアンモニウム ビス(トリフルオロメタンスルホニル)イミド、N−メチル−N−プロピルピぺリジニウム ビス(トリフルオロメタンスルホニル)イミド、N−(2−メトキシエチル)−N−メチルピロリジウム テトラフルオロボラート、N,N−ジエチル−N−メチル−N−(2−メトキシエチル)アンモニウム テトラフルオロボラート、1−プロピル−3−メチルイミダゾリウムアイオダイド、1−アリル−3−エチルイミダゾリウムアイオダイド等を用いることができる。 The ionic liquid that can be used in the present invention can be used without particular limitation as long as it is an ionic liquid that undergoes a phase transition near room temperature, specifically, an ionic liquid having a transition point such as a melting point at 0 ° C. to 50 ° C. For example, N, N, N-trimethyl-N-propylammonium bis (trifluoromethanesulfonyl) imide, N-methyl-N-propylpiperidinium bis (trifluoromethanesulfonyl) imide, N- (2-methoxyethyl) -N- Methylpyrrolidinium tetrafluoroborate, N, N-diethyl-N-methyl-N- (2-methoxyethyl) ammonium tetrafluoroborate, 1-propyl-3-methylimidazolium iodide, 1-allyl-3- Ethyl imidazolium iodide etc. can be used.
本発明で使用できる天然高分子は、室温付近で相転移する天然高分子、具体的には、0℃〜50℃に融点等の転移点を有する天然高分子であれば特に制限なく用いることができるが、例えば、0℃〜50℃に融点等の転移点を有するポリアミン、天然ゴム、ポリペプチド等を用いることができる。 The natural polymer that can be used in the present invention is not particularly limited as long as it is a natural polymer that undergoes a phase transition near room temperature, specifically, a natural polymer having a transition point such as a melting point at 0 ° C to 50 ° C. For example, polyamine, natural rubber, polypeptide, etc. having a transition point such as a melting point at 0 ° C. to 50 ° C. can be used.
本発明で使用できる合成高分子は、室温付近で相転移する合成高分子、具体的には、0℃〜50℃に融点等の転移点を有する合成高分子であれば特に制限なく用いることができるが、例えば、0℃〜50℃に融点等の転移点を有する合成樹脂(プラスチック)(ポリ塩化ビニル、ポリエチレン、フェノール樹脂、ポリテトラメチレンオキシド、ポリエチレンアジペートなど)、シリコン樹脂(シリコンゴム、シリコンオイル)、合成繊維(ナイロン、ビニロン、ポリエステル、ポリエチレンテレフタラートなど)、合成ゴム(cis−1,4−ポリブタジエン、cis−1,4−ポリイソプレン)等を用いることができる。 The synthetic polymer that can be used in the present invention is not particularly limited as long as it is a synthetic polymer that undergoes a phase transition near room temperature, specifically, a synthetic polymer having a transition point such as a melting point at 0 ° C. to 50 ° C. For example, a synthetic resin (plastic) having a transition point such as a melting point at 0 ° C. to 50 ° C. (polyvinyl chloride, polyethylene, phenol resin, polytetramethylene oxide, polyethylene adipate, etc.), silicon resin (silicon rubber, silicon) Oil), synthetic fibers (nylon, vinylon, polyester, polyethylene terephthalate, etc.), synthetic rubber (cis-1,4-polybutadiene, cis-1,4-polyisoprene) and the like can be used.
本発明で使用できるリン脂質は、室温付近で相転移するリン脂質、具体的には、0℃〜50℃に融点等の転移点を有するリン脂質であれば特に制限なく用いることができるが、例えば、ジミリストイルホスファチジルコリン、ジパルミトイルホスファチジルコリン、ジステアリルホスファチジルコリン等を用いることができる。 The phospholipid that can be used in the present invention can be used without particular limitation as long as it is a phospholipid that undergoes a phase transition near room temperature, specifically, a phospholipid having a transition point such as a melting point at 0 ° C. to 50 ° C. For example, dimyristoyl phosphatidylcholine, dipalmitoyl phosphatidylcholine, distearyl phosphatidylcholine and the like can be used.
本発明のカプセル化された色材において、好ましくは、カプセルはミセル又は脂質二重膜(リポソーム)からなる。 In the encapsulated colorant of the present invention, the capsule is preferably composed of a micelle or a lipid bilayer (liposome).
ミセルは、好ましくは、界面活性剤により形成されている。界面活性剤としては、アニオン性界面活性剤が好ましく、特に、スルホン基、カルボキシル基を有する界面活性剤、具体的には、脂溶性部位とスルホ基、又は、脂溶性部位とカルボキシ基から構成される界面活性剤が好ましい。
本発明で使用できる界面活性剤としては、例えば、ラウリル硫酸ナトリウム、ラウリン酸ナトリウム等が挙げられる。The micelle is preferably formed of a surfactant. As the surfactant, an anionic surfactant is preferable, and in particular, a surfactant having a sulfone group or a carboxyl group, specifically, a fat-soluble portion and a sulfo group, or a fat-soluble portion and a carboxyl group. A surfactant is preferred.
Examples of the surfactant that can be used in the present invention include sodium lauryl sulfate and sodium laurate.
脂質二重膜(リポソーム)は、通常リン脂質から形成されている。リン脂質としては、例えば、ホスファチジルコリン、ホスファチジルエタノールアミン、ホスファチジルイノシトール、ホスファチジルセリン、ホスファチジルグリセロール、ジホスファチジルグリセロール、スフィンゴミエリン等が挙げられるが、これらに限定されない。 Lipid bilayers (liposomes) are usually formed from phospholipids. Examples of the phospholipid include, but are not limited to, phosphatidylcholine, phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, phosphatidylglycerol, diphosphatidylglycerol, and sphingomyelin.
本発明のカプセル化された色材の製造方法は、(1)室温付近に融点等の転移点を有する有機化合物、及び、少なくとも1種の分子の会合状態の変化により光の吸収スペクトルが変化する顔料、有機色素又は赤外線吸収色素を含む組成物を形成する工程、及び(2)前記組成物、及び界面活性剤又はリン脂質を水に添加して水溶液を得る工程、を含む。 In the method for producing an encapsulated color material of the present invention, (1) an absorption spectrum of light changes due to a change in an association state of an organic compound having a transition point such as a melting point near room temperature and at least one molecule. Forming a composition containing a pigment, an organic dye or an infrared absorbing dye, and (2) adding the composition and a surfactant or phospholipid to water to obtain an aqueous solution.
前記有機化合物、及び、前記顔料、有機色素又は赤外線吸収色素を含む組成物を調製するには、例えば、室温付近に融点等の転移点を有する液晶性化合物等の有機化合物、顔料、有機色素又は赤外線吸収色素を有機溶媒(例えば、クロロホルム等)に溶解し、得られた溶液を基板(ガラス板、プラスチックフィルム等)上に滴下して溶媒を真空で乾燥する等して蒸発させて有機化合物と顔料、有機色素又は赤外線吸収色素を含む組成物からなるキャストフィルムを得る。
ここで、有機溶媒に添加する液晶性化合物等の有機化合物、顔料、有機色素又は赤外線吸収色素の濃度としては、使用する有機化合物、顔料等の種類により適宜定めることができる。To prepare a composition containing the organic compound and the pigment, organic dye or infrared absorbing dye, for example, an organic compound such as a liquid crystalline compound having a transition point such as a melting point near room temperature, a pigment, an organic dye or Infrared absorbing dye is dissolved in an organic solvent (for example, chloroform), and the resulting solution is dropped on a substrate (glass plate, plastic film, etc.) and the solvent is evaporated by drying in a vacuum, etc. A cast film made of a composition containing a pigment, an organic dye or an infrared absorbing dye is obtained.
Here, the concentration of an organic compound such as a liquid crystal compound, a pigment, an organic dye, or an infrared absorbing dye added to the organic solvent can be determined as appropriate depending on the type of the organic compound, the pigment, and the like to be used.
次に、上記のキャストフィルムを基板から取り除き、これを界面活性剤又はリン脂質が溶解した水溶液に添加し、溶液を撹拌することにより、界面活性剤により形成されるミセル又はリン脂質により形成されるリポソームを形成させ、これらの内部に有機化合物、及び顔料、有機色素又は赤外線吸収色素を内包させることにより、カプセル化された色材を含む水溶液を得ることができる。撹拌は、超音波処理、機械的ホモジナイザー(コロイドミル)、高圧ホモジナイザー等で行うことができる。
界面活性剤又はリン脂質の濃度は、使用する界面活性剤等の種類により適宜定めることができるが、通常、0.1mM〜103mMである。
また、キャストフィルム(即ち、液晶性化合物等の有機化合物、顔料等の組成物)の添加量は適宜定めることができるが、通常、0.1〜1000g/Lである。Next, the cast film is removed from the substrate, added to an aqueous solution in which the surfactant or phospholipid is dissolved, and stirred to form the micelle or phospholipid formed by the surfactant. By forming liposomes and encapsulating an organic compound and a pigment, an organic dye or an infrared-absorbing dye therein, an aqueous solution containing an encapsulated coloring material can be obtained. Stirring can be performed by ultrasonic treatment, a mechanical homogenizer (colloid mill), a high-pressure homogenizer, or the like.
The concentration of the surfactant or phospholipid can be appropriately determined depending on the type of the surfactant used and the like, but is usually 0.1 mM to 10 3 mM.
Moreover, although the addition amount of a cast film (namely, organic compounds, such as a liquid crystalline compound, and compositions, such as a pigment) can be determined suitably, it is 0.1-1000 g / L normally.
本発明のカプセル化された色材は、室温付近に融点等の転移点を有する有機化合物、少なくとも1種の分子の会合状態の変化により光吸収が変化する顔料、有機色素又は赤外線吸収色素、及び界面活性剤を水に添加して水溶液を得る工程、を含む製造方法により調製することもできる。
溶液の撹拌方法、界面活性剤の濃度等は上記の製造方法と同様である。The encapsulated colorant of the present invention comprises an organic compound having a transition point such as a melting point near room temperature, a pigment whose light absorption changes due to a change in the association state of at least one molecule, an organic dye or an infrared absorbing dye, and It can also be prepared by a production method comprising a step of adding a surfactant to water to obtain an aqueous solution.
The method for stirring the solution, the concentration of the surfactant and the like are the same as in the above production method.
カプセル化された色材(即ち、ミセル)の粒径は、使用する有機化合物、顔料、有機色素又は赤外線吸収色素、界面活性剤の種類、添加量により変化するが、通常、1nm〜100μm、好ましくは10nm〜10μmである。 The particle size of the encapsulated colorant (that is, micelle) varies depending on the organic compound, pigment, organic dye or infrared absorbing dye used, the type of surfactant, and the amount added, but is usually 1 nm to 100 μm, preferably Is 10 nm to 10 μm.
本発明の色材の1つの側面は、上記した色材を含有する溶液である。
また、本発明の色材のもう1つの側面は、上記した色材を含有する分散液である。One aspect of the color material of the present invention is a solution containing the color material described above.
Another aspect of the color material of the present invention is a dispersion containing the color material described above.
実施態様1の色材の1つの側面は、(i)少なくとも1種の室温付近に融点等の転移点を有する脂肪酸、及び(ii)少なくとも1種の顔料、有機色素又は赤外線吸収色素を含み、前記脂肪酸、及び前記顔料、有機色素又は赤外線吸収色素はミセルにより内包されている色材である。
脂肪酸の種類によっては、その金属塩は界面活性剤として作用しミセルを形成する。即ち、ミセル内部においては、顔料、有機色素又は赤外線吸収色素は脂肪酸に溶解又は分散し、当該脂肪酸の金属塩(ナトリウム塩等)はミセルを形成している色材を提供することができる。
このような色材の好ましい例として、ラウリン酸、及び少なくとも1種の顔料、有機色素又は赤外線吸収色素を含み、ラウリン酸、及び前記顔料、有機色素又は赤外線吸収色素は、ラウリン酸ナトリウムにより形成されるミセルにより内包されている色材である。One aspect of the colorant of
Depending on the type of fatty acid, the metal salt acts as a surfactant and forms micelles. That is, inside the micelle, a pigment, an organic dye, or an infrared absorbing dye is dissolved or dispersed in a fatty acid, and a metal salt (such as a sodium salt) of the fatty acid can provide a coloring material that forms a micelle.
Preferred examples of such a coloring material include lauric acid and at least one pigment, organic dye or infrared absorbing dye, and the lauric acid and the pigment, organic dye or infrared absorbing dye are formed of sodium laurate. It is a color material included in the micelle.
実施態様1のカプセル化された色材は、基本的に水に溶解性であり、色材として実用的に使用するにはこれを水、有機溶媒に不溶化することが好ましい。本発明においては、上記のカプセル化された色材に特定のカチオンを含有させることにより、水に難溶性の色材を提供することができる。
The encapsulated color material of
即ち、本発明のもう1つの実施態様は、(i)室温付近に融点等の転移点を有する有機化合物、及び(ii)少なくとも1種の顔料、有機色素又は赤外線吸収色素を含み、前記有機化合物、及び前記顔料、有機色素又は赤外線吸収色素はミセル又はリポソームからなるカプセルにより内包されており、前記ミセル又はリポソームの表面においてカチオンが結合又は付着している、色材である(以下「実施態様2」とも言う)。
実施態様2の色材は、好ましくは水難溶性色材である。ここで、水難溶性色材とは、水に全く溶けない色材に加えて、水に僅かに溶ける色材(例えば、溶解度として、1mM未満)も包含する。
上記の液晶性化合物、有機溶媒、顔料、有機色素、赤外線吸収色素、ミセル、リポソームは、実施態様1で説明したものと同様である。That is, another embodiment of the present invention includes (i) an organic compound having a transition point such as a melting point near room temperature, and (ii) at least one pigment, organic dye or infrared absorbing dye, , And the pigment, organic dye, or infrared absorbing dye is a colorant that is encapsulated by capsules made of micelles or liposomes, and a cation is bound or attached to the surface of the micelles or liposomes (hereinafter referred to as “
The color material of
The liquid crystal compound, organic solvent, pigment, organic dye, infrared absorbing dye, micelle, and liposome are the same as those described in the first embodiment.
実施態様2で用いられるカチオンは、バリウムイオン、カルシウムイオン、マグネシウムイオン、亜鉛イオン、鉛イオン、銅イオン、水銀イオン、銀イオン又はストロンチウムイオンである。これらのカチオンを使用すると、ミセル表面上のアニオンと結合してカプセル化された色材が沈殿し、水難溶性の色材を提供することができる。
The cation used in
本発明の実施態様2の色材の製造方法は、(1)室温付近に融点等の転移点を有する有機化合物、及び、少なくとも1種の分子の会合状態の変化により光の吸収スペクトルが変化する顔料、有機色素又は赤外線吸収色素を含む組成物を形成する工程、(2)前記組成物、及び界面活性剤又はリン脂質を水に添加して水溶液を得る工程、(3)前記水溶液に、カチオンを生成する化合物を添加する工程を含む。
In the method for producing a coloring material according to
本発明の実施態様2の色材の製造方法の(1)と(2)の工程は、実施態様1のカプセル化された色材の製造方法で説明した通りである。
理論に拘束されることを意図するものではないが、(2)の工程において、室温付近に融点等の転移点を有する有機化合物、及び顔料、有機色素又は赤外線吸収色素を内包するミセル又はリポソームを含む水溶液が生成し、当該水溶液にカチオンを添加することにより、ミセル又はリポソームが凝集して、水難溶性色材が生成すると考えられる。The steps (1) and (2) of the method for producing a color material according to
Although not intended to be bound by theory, in the step (2), an organic compound having a transition point such as a melting point in the vicinity of room temperature, and a micelle or liposome containing a pigment, an organic dye or an infrared-absorbing dye It is considered that an aqueous solution containing water is generated and a cation is added to the aqueous solution, whereby micelles or liposomes aggregate to form a poorly water-soluble colorant.
カチオンとしては、バリウムイオン、カルシウムイオン、マグネシウムイオン、亜鉛イオン、鉛イオン、銅イオン、水銀イオン、銀イオン又はストロンチウムイオンが挙げられ、これらのカチオンを生成する化合物としては、例えば、塩化バリウム、塩化カルシウム、塩化マグネシウム、塩化亜鉛、塩化鉛、塩化銅、塩化水銀、塩化銀、塩化ストロンチウム等が挙げられる。 Examples of the cation include barium ion, calcium ion, magnesium ion, zinc ion, lead ion, copper ion, mercury ion, silver ion, and strontium ion. Examples of the compound that generates these cations include barium chloride, chloride, and the like. Examples include calcium, magnesium chloride, zinc chloride, lead chloride, copper chloride, mercury chloride, silver chloride, and strontium chloride.
また、実施態様2の色材は、(1)室温付近に融点等の転移点を有する有機化合物、少なくとも1種の分子の会合状態の変化により光吸収が変化する顔料、有機色素又は赤外線吸収色素、及び界面活性剤又はリン脂質を水に添加して水溶液を得る工程、及び(2)前記水溶液に、カチオンを生成する化合物を添加する工程を含む、製造方法により調製することもできる。
In addition, the color material of
実施態様2の色材の1つの側面は、(i)少なくとも1種の室温付近に融点等の転移点を有する脂肪酸、及び(ii)少なくとも1種の顔料、有機色素又は赤外線吸収色素を含み、前記脂肪酸、及び前記顔料、有機色素又は赤外線吸収色素はミセルにより内包されており、前記ミセルの表面においてカチオンが結合又は付着している色材である。
脂肪酸の種類によっては、その金属塩は界面活性剤として作用しミセルを形成する。即ち、ミセル内部においては、顔料、有機色素又は赤外線吸収色素は脂肪酸に溶解又は分散し、当該脂肪酸の金属塩(ナトリウム塩等)はミセルを形成している色材を提供することができる。
このような色材の好ましい例として、ドデカン酸、及び少なくとも1種の顔料、有機色素又は赤外線吸収色素を含み、ドデカン酸、及び前記顔料、有機色素又は赤外線吸収色素は、ドデカン酸ナトリウムにより形成されるミセルにより内包されており、前記ミセルの表面においてカチオンが結合又は付着している色材である。ここで、カチオンとしては、カルシウムイオンが好ましい。One aspect of the colorant of
Depending on the type of fatty acid, the metal salt acts as a surfactant and forms micelles. That is, inside the micelle, a pigment, an organic dye, or an infrared absorbing dye is dissolved or dispersed in a fatty acid, and a metal salt (such as a sodium salt) of the fatty acid can provide a coloring material that forms a micelle.
Preferred examples of such a coloring material include dodecanoic acid and at least one pigment, organic dye or infrared absorbing dye, and the dodecanoic acid and the pigment, organic dye or infrared absorbing dye are formed of sodium dodecanoate. The coloring material is encapsulated in the micelle and has a cation bonded or attached to the surface of the micelle. Here, as a cation, a calcium ion is preferable.
本発明の1つの態様は、実施態様2の色材、及び水、有機溶媒又はこれらの混合物を含む分散液である。
One aspect of the present invention is a dispersion comprising the colorant of
本発明のもう1つの態様は、実施態様2の色材、水、有機溶媒又はこれらの混合物、及び樹脂を含む塗料組成物である。
実施態様2の色材は、水、有機溶媒に難溶性であることから、当該色材を水、有機溶媒等に分散して塗料として好適に使用することができる。Another aspect of the present invention is a coating composition comprising the colorant of
Since the color material of
本発明の塗料組成物において、樹脂成分として使用できる樹脂や塗装時の硬化により樹脂成分から形成される樹脂としては、特に限定されるものではなく、塗料業界において通常使用されている樹脂を例示することができる。具体的には、アクリル樹脂、シリコーン樹脂、アクリルシリコーン樹脂、スチレンアクリル共重合樹脂、ポリエステル樹脂、ふっ素樹脂、ロジン樹脂、石油樹脂、クマロン樹脂、フェノール樹脂、ウレタン樹脂、メラミン樹脂、尿素樹脂、エポキシ樹脂、セルロース樹脂、キシレン樹脂、アルキッド樹脂、脂肪族炭化水素樹脂、ブチラール樹脂、マレイン酸樹脂、フマル酸樹脂、ビニル樹脂(ポリ塩化ビニリデン等)、アミン樹脂、ケチミン樹脂等が挙げられる。これらの樹脂を一種単独で用いても良く、二種以上組み合わせて用いてもよい。 In the coating composition of the present invention, the resin that can be used as the resin component and the resin that is formed from the resin component by curing at the time of coating are not particularly limited, and examples include resins that are usually used in the coating industry. be able to. Specifically, acrylic resin, silicone resin, acrylic silicone resin, styrene acrylic copolymer resin, polyester resin, fluorine resin, rosin resin, petroleum resin, coumarone resin, phenol resin, urethane resin, melamine resin, urea resin, epoxy resin Cellulose resin, xylene resin, alkyd resin, aliphatic hydrocarbon resin, butyral resin, maleic acid resin, fumaric acid resin, vinyl resin (polyvinylidene chloride, etc.), amine resin, ketimine resin and the like. These resins may be used alone or in combination of two or more.
本発明の塗料組成物において使用できる有機溶媒としては、特に限定されるものではなく、塗料において通常使用されている有機溶媒を例示することができる。例えば、アルコール(イソプロピルアルコール、エタノール、ブタノール等)、ケトン系溶媒(メチルエチルケトン、アセトン等)、エステル系(酢酸エチル、酢酸ブチル)、トルエン、キシレン、アミド系溶媒(ジメチルアセトアミド等)等を使用することができる。
有機溶媒は二種以上を混合して用いることができ、また、水と有機溶媒の混合物を使用することもできる。It does not specifically limit as an organic solvent which can be used in the coating composition of this invention, The organic solvent normally used in a coating material can be illustrated. For example, alcohol (isopropyl alcohol, ethanol, butanol, etc.), ketone solvents (methyl ethyl ketone, acetone, etc.), ester solvents (ethyl acetate, butyl acetate), toluene, xylene, amide solvents (dimethylacetamide, etc.), etc. Can do.
Two or more organic solvents can be mixed and used, and a mixture of water and an organic solvent can also be used.
本発明の塗料組成物においては、実施態様2の色材を2種以上併用してもよい。
また、本発明の塗料組成物は、実施態様2の色材以外の顔料を含有してもよい。このような顔料は、特に限定されるものではなく、塗料業界において通常使用されている顔料を使用できる。具体例としては、二酸化チタン、酸化鉄、カーボンブラック等の着色顔料、シリカ、タルク、マイカ、炭酸カルシウム、硫酸バリウム等の体質顔料、亜鉛、リン酸亜鉛、リン酸アルミニウム、モリブデン酸亜鉛、メタホウ酸バリウム、ハイドロカルマイト等の防錆顔料、アルミニウム、ニッケル、クロム、錫、銅、銀、白金、金、ステンレス、ガラスフレーク等の光輝顔料等が挙げられる。In the coating composition of the present invention, two or more colorants according to
Moreover, the coating composition of this invention may contain pigments other than the coloring material of
本発明の塗料組成物においては、顔料分散剤、増粘剤、表面調整剤、造膜助剤、紫外線吸収剤、酸化防止剤、難燃剤、帯電防止剤、防錆剤等、当業者によってよく知られている各種成分を含むことができる。 In the coating composition of the present invention, pigment dispersants, thickeners, surface conditioners, film-forming aids, UV absorbers, antioxidants, flame retardants, antistatic agents, rust inhibitors, etc. Various known ingredients can be included.
本発明の塗料組成物の塗装手段は、特に限定されず、既知の塗装手段、例えば、スプレー塗装、ローラー塗装、刷毛塗装、コテ塗装、ヘラ塗装等が利用できる。 The coating means of the coating composition of the present invention is not particularly limited, and known coating means such as spray coating, roller coating, brush coating, iron coating, spatula coating and the like can be used.
本発明の塗料組成物は、低温状態では太陽光を吸収し、温度が上昇すると太陽光を透過する特性を有することから機能性の塗料として使用することができる。非限定的な具体例として、冬場には太陽光を吸収し熱に変換し、夏場には太陽光を透過し温度上昇を防ぐという特性を有する建築用塗料として使用することが可能である。 The coating composition of the present invention can be used as a functional coating because it has the property of absorbing sunlight at low temperatures and transmitting sunlight when the temperature rises. As a non-limiting specific example, it can be used as a building paint having the characteristics of absorbing sunlight and converting it into heat in winter and transmitting sunlight in summer to prevent temperature rise.
本発明のもう1つの態様は、反射材、及び当該反射材の上に設けられた本発明の水難溶性色材を含む層を備える遮熱材である。 Another aspect of the present invention is a heat shielding material including a reflective material and a layer containing the poorly water-soluble color material of the present invention provided on the reflective material.
反射材としては、例えば、アルミを主成分とする遮熱材、酸化チタンに代表される高反射顔料を用いた遮熱塗料等を使用することができる。 As the reflecting material, for example, a heat shielding material mainly composed of aluminum, a heat shielding paint using a highly reflective pigment typified by titanium oxide, or the like can be used.
実施態様2の色材を含む層は、例えば、上記した本発明の塗料組成物を反射材の上に塗布することにより形成することができる。また、実施態様2の色材を樹脂に混合してフィルムを形成し、当該フィルムを反射材の上に積層することによっても層を形成することができる。
反射材と実施態様2の色材を含む層を反射材に設ける際に、反射材と当該層の間に接着層を設けてもよい。The layer containing the color material of
When the reflective material and the layer containing the color material of
本発明の遮熱材は、実施態様2の色材は冬場には太陽光を吸収し熱に変換し、夏場には太陽光を透過して反射材により太陽光を反射するため温度上昇を防ぐことができる。
In the heat shielding material of the present invention, the color material of
以下、本発明を実施例により説明するが、本発明はこれに限定されるものではない。 EXAMPLES Hereinafter, although an Example demonstrates this invention, this invention is not limited to this.
[参考例1]
SiPc(OH) 2 /(シクロヘキサノール+グリセロール)フィルムの調製
SiPc(OH)2をシクロヘキサノール0.2mLに溶解し、さらにグリセロール0.4mLを加えることで、濃度10−5Mの溶液を作製した。溶液を入れる容器には1cmディスポセルセルを用いた。[Reference Example 1]
Preparation of SiPc (OH) 2 / (cyclohexanol + glycerol) film SiPc (OH) 2 was dissolved in 0.2 mL of cyclohexanol, and 0.4 mL of glycerol was further added to prepare a solution having a concentration of 10 −5 M. . A 1 cm disposable cell was used as a container for storing the solution.
[実施例1]
SiPc(OH) 2 /8OCBフィルム調製、及びそのカプセル化と不溶化
SiPc(OH)2/8OCB混合薄膜(フィルム)の作製方法の模式図を図2に示す。
SiPc(OH)2(2.0×10−8mol)と8OCB(2.0×10−4mol、60mg)をトルエンに溶解し混合溶液を作製した。混合溶液を厚さ0.5mmの貼り合わせセルに滴下し、8OCBが液晶相となる60℃で真空乾燥することにより、溶媒トルエンを除去した。その後、上からガラス基板を貼り合わせることで厚さの均一なフィルムを得た。[Example 1]
FIG. 2 shows a schematic diagram of SiPc (OH) 2 / 8OCB film preparation, and encapsulation and insolubilized SiPc (OH) 2 / 8OCB mixed thin film (film) production method.
SiPc (OH) 2 (2.0 × 10 −8 mol) and 8OCB (2.0 × 10 −4 mol, 60 mg) were dissolved in toluene to prepare a mixed solution. The mixed solution was dropped into a 0.5 mm-thick bonding cell, and the solvent toluene was removed by vacuum drying at 60 ° C. in which 8OCB became a liquid crystal phase. Then, the glass substrate was bonded together from the top, and the film with uniform thickness was obtained.
上記の手法と同様に、サンプル瓶中でフィルムを作製し、その後界面活性剤として0.5mLの2%SDS(ドデシル硫酸ナトリウム)水溶液を加えた。サンプルに超音波処理を3時間行うことで、SiPc(OH)2/8OCB混合物を含有するSDSミセル水溶液を得た。Similarly to the above method, a film was prepared in a sample bottle, and then 0.5 mL of 2% SDS (sodium dodecyl sulfate) aqueous solution was added as a surfactant. The sample was sonicated for 3 hours to obtain an aqueous SDS micelle solution containing a SiPc (OH) 2 / 8OCB mixture.
作製したSDSミセル水溶液に0.2%塩化バリウム水溶液を0.5mL加えた。その後、真空乾燥により水を除去した。 0.5 mL of 0.2% barium chloride aqueous solution was added to the produced SDS micelle aqueous solution. Thereafter, water was removed by vacuum drying.
1.調製した試料の光学特性の測定
(1)SiPc(OH)2/(シクロヘキサノール+グリセロール)フィルムの電子吸収スペクトル
測定にはJASCO社製V−570型分光光度計を用いた。また、サンプルの温度調節には高低温サーキュレータ(Julabo、F25−ED)、スターラー付き恒温セルホルダ(JASCO、STR−458)を用いた。溶液を入れる容器には1cmディスポセルセルを用いた。また、測定はサーキュレータの水温が設定温度に達してから3分後に行った。測定結果を図3に示す。
図3に示されているように、サンプルの温度が10℃、50℃、80℃と上昇するに従い、電子吸収スペクトルに大きな変化が観察された。1. Measurement of optical properties of prepared sample (1) Electronic absorption spectrum of SiPc (OH) 2 / (cyclohexanol + glycerol) film A JASCO V-570 spectrophotometer was used for measurement. In addition, a high and low temperature circulator (Julabo, F25-ED) and a constant temperature cell holder with a stirrer (JASCO, STR-458) were used for temperature control of the sample. A 1 cm disposable cell was used as a container for storing the solution. The measurement was performed 3 minutes after the water temperature of the circulator reached the set temperature. The measurement results are shown in FIG.
As shown in FIG. 3, as the sample temperature increased to 10 ° C., 50 ° C., and 80 ° C., a large change was observed in the electron absorption spectrum.
(2)SiPc(OH)2/8OCBフィルムの電子吸収スペクトル
8OCBの相転移温度前後での電子吸収を調べるため、フィルム温度を制御し、各温度で電子吸収スペクトルを測定した。サンプルの温度調節には高低温サーキュレータ(Julabo、F25−ED)、スターラー付き恒温セルホルダ (JASCO、STR−458)を用いた。また、測定はサーキュレータの水温が設定温度に達してから3分後に行った。SiPc(OH)2/8OCBフィルムの測定結果を図4に示す。
SiPc(OH)2/8OCBフィルムは、サンプル温度が30℃では電子吸収スペクトルがブロードな吸収帯を示すのに対して、60℃、80℃では、シャープな吸収帯を示しており、電子吸収スペクトルが室温付近で大きく変化することが観察された。このことから、30℃付近ではSiPc(OH)2は会合状態であるのに対して、60℃、80℃と高温になるにつれて8OCBが液晶、液体状態となり、SiPc(OH)2は単量体として存在していると考えられる。(2) Electronic absorption spectrum of SiPc (OH) 2 / 8OCB film In order to examine the electronic absorption around the phase transition temperature of 8OCB, the film temperature was controlled, and the electronic absorption spectrum was measured at each temperature. A high and low temperature circulator (Julabo, F25-ED) and a constant temperature cell holder with a stirrer (JASCO, STR-458) were used for temperature control of the sample. The measurement was performed 3 minutes after the water temperature of the circulator reached the set temperature. The measurement results of the SiPc (OH) 2 / 8OCB film are shown in FIG.
The SiPc (OH) 2 / 8OCB film shows a broad absorption band at a sample temperature of 30 ° C., whereas it shows a sharp absorption band at 60 ° C. and 80 ° C., and the electron absorption spectrum Was observed to vary greatly around room temperature. From this, SiPc (OH) 2 is in an associated state near 30 ° C., whereas 8OCB becomes a liquid crystal and liquid state as the temperature increases to 60 ° C. and 80 ° C., and SiPc (OH) 2 is a monomer. It is thought that it exists as.
(3)不溶化したカプセルの拡散反射スペクトル
不溶化したカプセルを0.5mm貼り合わせセルに入れて測定に用いた。測定には、JASCO社製V−570型分光光度計と積分球を用いた。また、温調器を組み合わせることで、サンプルの温度制御を可能にした。測定結果を図5に示す。
サンプル温度が30℃では、拡散反射スペクトルがブロードな吸収帯を示すのに対して、約60℃ではシャープな吸収帯を示している。図5から、SiPc(OH)2/8OCBフィルムが有していた会合挙動は不溶化したカプセル中において保持されていることが確認された。(3) Diffuse reflection spectrum of insolubilized capsules The insolubilized capsules were placed in a 0.5 mm bonded cell and used for measurement. For measurement, a JASCO V-570 spectrophotometer and an integrating sphere were used. In addition, the temperature of the sample can be controlled by combining a temperature controller. The measurement results are shown in FIG.
When the sample temperature is 30 ° C., the diffuse reflection spectrum shows a broad absorption band, whereas at about 60 ° C., a sharp absorption band is shown. From FIG. 5, it was confirmed that the association behavior that the SiPc (OH) 2 / 8OCB film had was retained in the insolubilized capsule.
[実施例2]
遮熱効果の評価
カプセル化、不溶化の処理を行ったSiPc(OH)2/8OCB混合物、SiPc(OH)2/7CB混合物をポリ塩化ビニリデン(PVDC)のDMA溶液に分散させ、塗料とした。これらの塗料をアルミ箔に滴下し、真空乾燥によりDMAを除去することで塗膜を作製した。
アルミ箔上に塗布した塗膜に、キセノンランプ(浜松ホトニクス、C2577)を照射し、それぞれの塗膜の温度上昇を調べた。このとき、SiPc(OH)2の紫外線による退色を防ぐため、カットフィルター(>390nm、シグマ光機、SCF−39L)を用いた。
測定結果を図6に示す。図6の上段は、SiPc(OH)2/7CB混合物を含有する塗膜のキセノンランプ照射実験の結果を示し、図6の下段は、SiPc(OH)2/8OCB混合物を含有する塗膜のキセノンランプ照射実験の結果を示す。
キセノンランプ照射下で、SiPc(OH)2/8OCB混合物を含有する塗膜は34.4℃まで温度上昇したのに対し、SiPc(OH)2/7CB混合物を含有する塗膜は29.5℃までしか温度上昇しなかった。また照射後、SiPc(OH)2/7CB混合物を含有する塗膜では、肉眼で色が変化しているのが確認できた。したがって、7CBの相転移に伴いSiPc(OH)2の吸収スペクトルが変化したことで、塗膜内のSiPc(OH)2による光熱変換が抑えられたのではないかと考えられる。[Example 2]
Evaluation of heat shielding effect The SiPc (OH) 2 / 8OCB mixture and SiPc (OH) 2 / 7CB mixture that had been subjected to encapsulation and insolubilization treatment were dispersed in a DMA solution of polyvinylidene chloride (PVDC) to obtain a paint. These paints were dropped on an aluminum foil, and DMA was removed by vacuum drying to prepare a coating film.
The coating applied on the aluminum foil was irradiated with a xenon lamp (Hamamatsu Photonics, C2577), and the temperature rise of each coating was examined. At this time, a cut filter (> 390 nm, Sigma Koki, SCF-39L) was used in order to prevent fading of SiPc (OH) 2 due to ultraviolet rays.
The measurement results are shown in FIG. Upper part of FIG. 6 shows the results of the xenon lamp irradiation experiments coating containing
Under xenon lamp irradiation, the coating containing SiPc (OH) 2 / 8OCB mixture rose to 34.4 ° C., whereas the coating containing SiPc (OH) 2 / 7CB mixture was 29.5 ° C. The temperature rose only up to. In addition, it was confirmed that the color of the coating film containing the SiPc (OH) 2 / 7CB mixture was changed with the naked eye after irradiation. Therefore, it is considered that the photothermal conversion by SiPc (OH) 2 in the coating film was suppressed by the change in the absorption spectrum of SiPc (OH) 2 accompanying the phase transition of 7CB.
[実施例3]
メカノクロミックの評価
SiPc(OH)2/8OCBフィルムは、室温に放置してもすぐには結晶相へと相転移せず、過冷却状態をとる。そこで、貼り合わせセル上側のガラス基板を動かして、過冷却状態のフィルムに機械的刺激を与えたところ、即座に結晶相へと相転移した。また、機械的刺激を与える前後のフィルムを用いて、拡散反射スペクトルを測定した。測定にはJASCO社製V−570型分光光度計と積分球を用いた。
SiPc(OH)2/8OCB薄膜の拡散反射スペクトルの測定結果を図7に示す。図7の左の図は過冷却状態での測定結果で、右の図は結晶相での測定結果を示す。ここで、900nmでのOD値を0とした。
過冷却状態では電子吸収スペクトルがシャープな吸収帯を示すのに対して、機械的刺激を与え相転移させた後は、シャープな吸収帯を示すことがわかった。このことから、フィルムに機械的刺激を与えたことで8OCBの相転移が誘起され、それに伴って電子吸収スペクトルが変化することを確かめられた。図8は、SiPc(OH)2/8OCB薄膜のエネルギーダイアグラム概念図である。[Example 3]
Evaluation of Mechanochromic The SiPc (OH) 2 / 8OCB film does not immediately transition to the crystalline phase even when it is left at room temperature, and is supercooled. Therefore, when the glass substrate on the upper side of the bonding cell was moved to give mechanical stimulation to the supercooled film, it immediately changed to the crystalline phase. Moreover, the diffuse reflection spectrum was measured using the film before and behind giving a mechanical stimulus. A JASCO V-570 spectrophotometer and integrating sphere were used for the measurement.
SiPc a (OH) 2 / 8OCB thin film measurements of diffuse reflectance spectrum shown in FIG. The left figure of FIG. 7 shows the measurement result in the supercooled state, and the right figure shows the measurement result in the crystal phase. Here, the OD value at 900 nm was set to zero.
It was found that the electron absorption spectrum shows a sharp absorption band in the supercooled state, whereas it shows a sharp absorption band after applying a mechanical stimulus and undergoing phase transition. From this, it was confirmed that the 8OCB phase transition was induced by applying mechanical stimulation to the film, and the electronic absorption spectrum was changed accordingly. Figure 8 is an energy diagram conceptual view of
[実施例4]
(1)SiPc(OH)2/ドデカン酸混合薄膜(フィルム)の作製
SiPc(OH)2(1.2×10−8mol)とドデカン酸(2.5×10−4mol、50mg)をクロロホルムに溶解し混合溶液を作製した。
混合溶液を厚さ0.5mmの貼り合せセルに滴下し、40℃で真空乾燥することにより、溶媒のクロロホルムを除去した。その後、上からガラス基板を貼り合せることで厚さの均一なフィルムを得た。[Example 4]
(1) Preparation of SiPc (OH) 2 / dodecanoic acid mixed thin film (film) SiPc (OH) 2 (1.2 × 10 −8 mol) and dodecanoic acid (2.5 × 10 −4 mol, 50 mg) in chloroform To prepare a mixed solution.
The mixed solution was dropped into a bonding cell having a thickness of 0.5 mm and vacuum-dried at 40 ° C. to remove the solvent chloroform. Then, the glass substrate was bonded together from the top, and the film with uniform thickness was obtained.
(2)調製した試料の光学特性の測定
SiPc(OH)2/ドデカン酸混合フィルムの電子吸収スペクトル
ドデカン酸の相転移温度(融点)前後での電子吸収を調べるため、フィルム温度を制御し、各温度で電子吸収スペクトルを測定した。
測定にはJASCO社製V−570型分光光度計を用いた。また、サンプルの温度調節には高低温サーキュレータ(Julabo、F25−ED)、スターラー付き恒温セルホルダ(JASCO、STR−458)を用いた。また、測定はサーキュレータの水温が設定温度に達してから3分後に行った。
ドデカン酸の融点44℃前後で電子吸収スペクトルが大きく変化することが観察された(図9)。ここでは、900nmのOD値を0とした。(2) Measurement of optical properties of the prepared sample Electronic absorption spectrum of SiPc (OH) 2 / dodecanoic acid mixed film In order to examine the electronic absorption before and after the phase transition temperature (melting point) of dodecanoic acid, the film temperature was controlled, The electronic absorption spectrum was measured at temperature.
A JASCO V-570 spectrophotometer was used for the measurement. In addition, a high and low temperature circulator (Julabo, F25-ED) and a constant temperature cell holder with a stirrer (JASCO, STR-458) were used for temperature control of the sample. The measurement was performed 3 minutes after the water temperature of the circulator reached the set temperature.
It was observed that the electron absorption spectrum changed greatly around the melting point of dodecanoic acid of 44 ° C. (FIG. 9). Here, the OD value at 900 nm was set to zero.
[実施例5]
(1)SiPc(OH)2/(13Z)−13−ドコセン酸混合薄膜(フィルム)の作製
SiPc(OH)2(7.4×10−9mol)と(13Z)−13−ドコセン酸(1.5×10−4mol、50mg)をクロロホルムに溶解し混合溶液を作製した。
混合溶液を厚さ0.5mmの貼り合せセルに滴下し、27℃で真空乾燥することにより、溶媒のクロロホルムを除去した。その後、上からガラス基板を貼り合せることで厚さの均一なフィルムを得た。[Example 5]
(1) Preparation of SiPc (OH) 2 / (13Z) -13-docosenoic acid mixed thin film (film) SiPc (OH) 2 (7.4 × 10 −9 mol) and (13Z) -13-docosenoic acid (1 0.5 × 10 −4 mol, 50 mg) was dissolved in chloroform to prepare a mixed solution.
The mixed solution was dropped into a bonding cell having a thickness of 0.5 mm and vacuum-dried at 27 ° C. to remove the solvent chloroform. Then, the glass substrate was bonded together from the top, and the film with uniform thickness was obtained.
(2)調製した試料の光学特性の測定
SiPc(OH)2/(13Z)−13−ドコセン酸混合薄膜の電子吸収スペクトル
(13Z)−13−ドコセン酸の相転移温度(融点)前後での電子吸収を調べるため、フィルム温度を制御し、各温度で電子吸収スペクトルを測定した。
測定にはJASCO社製V−570型分光光度計を用いた。また、サンプルの温度調節には高低温サーキュレータ(Julabo、F25−ED)、スターラー付き恒温セルホルダ(JASCO、STR−458)を用いた。また、測定はサーキュレータの水温が設定温度に達してから3分後に行った。
(13Z)−13−ドコセン酸の融点34℃前後で電子吸収スペクトルが大きく変化することが観察された(図10)。ここでは、900nmのOD値を0とした。(2) Measurement of optical properties of prepared sample Electronic absorption spectrum of SiPc (OH) 2 / (13Z) -13-docosenoic acid mixed thin film (13Z) Electrons before and after phase transition temperature (melting point) of 13-docosenoic acid In order to investigate absorption, the film temperature was controlled, and the electronic absorption spectrum was measured at each temperature.
A JASCO V-570 spectrophotometer was used for the measurement. In addition, a high and low temperature circulator (Julabo, F25-ED) and a constant temperature cell holder with a stirrer (JASCO, STR-458) were used for temperature control of the sample. The measurement was performed 3 minutes after the water temperature of the circulator reached the set temperature.
It was observed that the electron absorption spectrum changed greatly around the melting point of (13Z) -13-docosenoic acid of 34 ° C. (FIG. 10). Here, the OD value at 900 nm was set to zero.
Claims (27)
(ii)少なくとも1種の顔料、有機色素又は赤外線吸収色素
を含み、前記有機化合物、及び前記顔料、有機色素又は赤外線吸収色素はカプセルにより内包されている色材。(I) at least one organic compound having a transition point such as a melting point near room temperature, and (ii) at least one pigment, organic dye or infrared absorbing dye, the organic compound, and the pigment, organic dye or Infrared absorbing dye is a color material that is encapsulated in capsules.
(ii)少なくとも1種の顔料、有機色素又は赤外線吸収色素
を含み、前記脂肪酸、及び前記顔料、有機色素又は赤外線吸収色素は、当該脂肪酸の金属塩により形成されたミセルにより内包されている色材。(I) at least one fatty acid having a transition point such as a melting point near room temperature, and (ii) at least one pigment, organic dye or infrared absorbing dye, the fatty acid, and the pigment, organic dye or infrared absorbing The coloring material is a coloring material encapsulated by micelles formed from the metal salt of the fatty acid.
(ii)少なくとも1種の顔料、有機色素又は赤外線吸収色素
を含み、前記有機化合物、及び前記顔料、有機色素又は赤外線吸収色素はミセル又はリポソームからなるカプセルにより内包されており、前記ミセル又はリポソームの表面においてカチオンが結合又は付着している、色材。(I) at least one organic compound having a transition point such as a melting point near room temperature, and (ii) at least one pigment, organic dye or infrared absorbing dye, the organic compound, and the pigment, organic dye or Infrared absorbing pigment is encapsulated by capsules made of micelles or liposomes, and a cation is bonded to or attached to the surface of the micelles or liposomes.
(ii)少なくとも1種の顔料、有機色素又は赤外線吸収色素
を含み、前記脂肪酸、及び前記顔料、有機色素又は赤外線吸収色素は、当該脂肪酸の金属塩により形成されたミセルにより内包されており、前記ミセルの表面においてカチオンが結合又は付着している、色材。(I) at least one fatty acid having a transition point such as a melting point near room temperature, and (ii) at least one pigment, organic dye or infrared absorbing dye, the fatty acid, and the pigment, organic dye or infrared absorbing The coloring material is encapsulated by micelles formed of a metal salt of the fatty acid, and a cation is bonded or adhered to the surface of the micelle.
(2)前記組成物、及び界面活性剤又はリン脂質を水に添加して水溶液を得る工程、及び
(3)前記水溶液に、カチオンを生成する化合物を添加する工程
を含む、色材を調製する方法。(1) A step of forming a composition comprising an organic compound having a transition point such as a melting point near room temperature, and a pigment, an organic dye or an infrared-absorbing dye whose light absorption changes due to a change in the association state of at least one molecule ,
(2) A coloring material is prepared, including the step of adding the composition and a surfactant or phospholipid to water to obtain an aqueous solution, and (3) adding a compound that generates a cation to the aqueous solution. Method.
(2)前記水溶液に、カチオンを生成する化合物を添加する工程
を含む、色材を調製する方法。(1) An organic compound having a transition point such as a melting point near room temperature, a pigment whose light absorption changes due to a change in the association state of at least one molecule, an organic dye or an infrared absorbing dye, and a surfactant or phospholipid. And (2) a method of preparing a coloring material, comprising adding a compound that generates a cation to the aqueous solution.
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