WO2017022471A1 - 感温変色性色彩記憶性組成物及びそれを内包した感温変色性色彩記憶性マイクロカプセル顔料 - Google Patents
感温変色性色彩記憶性組成物及びそれを内包した感温変色性色彩記憶性マイクロカプセル顔料 Download PDFInfo
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- WO2017022471A1 WO2017022471A1 PCT/JP2016/071148 JP2016071148W WO2017022471A1 WO 2017022471 A1 WO2017022471 A1 WO 2017022471A1 JP 2016071148 W JP2016071148 W JP 2016071148W WO 2017022471 A1 WO2017022471 A1 WO 2017022471A1
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- DSOWAKKSGYUMTF-GZOLSCHFSA-M sodium;(1e)-1-(6-methyl-2,4-dioxopyran-3-ylidene)ethanolate Chemical compound [Na+].C\C([O-])=C1/C(=O)OC(C)=CC1=O DSOWAKKSGYUMTF-GZOLSCHFSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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
- YEHGKFOTJWYCBN-UHFFFAOYSA-N undecyl benzoate Chemical compound CCCCCCCCCCCOC(=O)C1=CC=CC=C1 YEHGKFOTJWYCBN-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/50—Sympathetic, colour changing or similar inks
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B43—WRITING OR DRAWING IMPLEMENTS; BUREAU ACCESSORIES
- B43K—IMPLEMENTS FOR WRITING OR DRAWING
- B43K23/00—Holders or connectors for writing implements; Means for protecting the writing-points
- B43K23/08—Protecting means, e.g. caps
- B43K23/12—Protecting means, e.g. caps for pens
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B43—WRITING OR DRAWING IMPLEMENTS; BUREAU ACCESSORIES
- B43K—IMPLEMENTS FOR WRITING OR DRAWING
- B43K25/00—Attaching writing implements to wearing apparel or objects involving constructional changes of the implements
- B43K25/02—Clips
- B43K25/026—Clips combined with other objects
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B43—WRITING OR DRAWING IMPLEMENTS; BUREAU ACCESSORIES
- B43K—IMPLEMENTS FOR WRITING OR DRAWING
- B43K29/00—Combinations of writing implements with other articles
- B43K29/02—Combinations of writing implements with other articles with rubbers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B43—WRITING OR DRAWING IMPLEMENTS; BUREAU ACCESSORIES
- B43K—IMPLEMENTS FOR WRITING OR DRAWING
- B43K5/00—Pens with ink reservoirs in holders, e.g. fountain-pens
- B43K5/005—Pen barrels
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B43—WRITING OR DRAWING IMPLEMENTS; BUREAU ACCESSORIES
- B43K—IMPLEMENTS FOR WRITING OR DRAWING
- B43K5/00—Pens with ink reservoirs in holders, e.g. fountain-pens
- B43K5/02—Ink reservoirs
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B43—WRITING OR DRAWING IMPLEMENTS; BUREAU ACCESSORIES
- B43K—IMPLEMENTS FOR WRITING OR DRAWING
- B43K7/00—Ball-point pens
- B43K7/02—Ink reservoirs; Ink cartridges
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B43—WRITING OR DRAWING IMPLEMENTS; BUREAU ACCESSORIES
- B43K—IMPLEMENTS FOR WRITING OR DRAWING
- B43K8/00—Pens with writing-points other than nibs or balls
- B43K8/02—Pens with writing-points other than nibs or balls with writing-points comprising fibres, felt, or similar porous or capillary material
- B43K8/04—Arrangements for feeding ink to writing-points
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B43—WRITING OR DRAWING IMPLEMENTS; BUREAU ACCESSORIES
- B43L—ARTICLES FOR WRITING OR DRAWING UPON; WRITING OR DRAWING AIDS; ACCESSORIES FOR WRITING OR DRAWING
- B43L19/00—Erasers, rubbers, or erasing devices; Holders therefor
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/16—Writing inks
- C09D11/17—Writing inks characterised by colouring agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/26—Thermosensitive paints
-
- 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
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
Definitions
- the present invention relates to a thermochromic color memory composition and a thermochromic color memory microcapsule pigment containing the same. More specifically, it exhibits a reversible discoloration of color development and decoloration with a large hysteresis characteristic due to temperature change, and even after the application of heat or cold heat required for discoloration is removed, either the colored state or the decolored state.
- the present invention relates to a temperature-sensitive color-changing color memory composition that holds the color in a reversible and reversible manner, and a temperature-sensitive color-changing color memory microcapsule pigment containing the same.
- the temperature-sensitive color-change color memory material changes color before and after the color change temperature as in the case of the conventional reversible thermo-color change material, and only one specific state exists in the normal temperature range of both the states before and after the color change. However, the other state is maintained while the heat or cold heat necessary for the state to be developed is applied, and when the heat or cold heat is no longer applied, the color changes compared with the type that returns to the state exhibited at room temperature. Either the color on the low temperature side or the color on the high temperature side can be selectively held in the normal temperature range, and can be held interchangeably by applying heat or cold as needed, and temperature sensitive recording. It is applied to various fields such as materials, toys, decoration, and printing.
- This kind of color memory effect is manifested only in a system in which a specific compound is used as a constituent component among compounds selected from esters, ketones, ethers and the like that control the color reaction.
- the present invention pursues a compound serving as a reaction medium that exhibits a color memory effect, and increases the degree of freedom of selection of the reaction medium, and further increases the utilization of this type of thermochromic color memory material. It is what.
- the present inventor is a system in which a compound having a specific structure is applied as a reaction medium for a color reaction, exhibits a thermochromic characteristic with a large hysteresis width ( ⁇ H), and exhibits an effective color memory effect.
- the headline and the present invention were completed.
- the present invention provides a reaction medium that controls the color reaction of (a) an electron-donating color-forming organic compound, (b) an electron-accepting compound, and (c) the component (a) and the component (b).
- a thermochromic color memory composition comprising an ester compound represented by the following formula (1).
- R represents any of an alkyl group having 3 to 18 carbon atoms, a cycloalkylalkyl group having 6 to 11 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, and an alkenyl group having 3 to 18 carbon atoms
- X is independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, or a halogen atom
- Y is independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
- the present invention also relates to a thermosensitive color-changing color memory microcapsule pigment comprising the temperature-sensitive color-changing color memory composition.
- the present invention further relates to an ink composition comprising the above microcapsule pigment and a vehicle.
- thermochromic color memory composition causes reversible discoloration of color development and decoloration, and exhibits a wide hysteresis width ( ⁇ H) with respect to the color density-temperature curve during this reversible discoloration. is there. And, both the color on the lower temperature side and the color on the higher temperature side than the discoloration temperature can be stored and held interchangeably, and by heating or cooling as required, any color can be reversibly reproduced and stored and held. The characteristics can be effectively expressed.
- a temperature-sensitive color-changing color memory composition having applicability in various fields such as temperature display, decoration, toys, or learning elements, and a temperature-sensitive color-changing color memory micro that includes the same Capsule pigments are provided.
- thermochromic color memory composition of the present invention and the thermochromic color memory microcapsule pigment using the same (reversible thermochromic composition having color memory and color memory using the same)
- thermochromic color memory microcapsule pigment using the same
- the hysteresis characteristics of the reversible thermochromic microcapsule pigment will be described based on the graph showing the color density-temperature curve of FIG.
- the vertical axis represents color density and the horizontal axis represents temperature.
- the color density due to temperature change varies along the arrow.
- A is a point indicating a density at a temperature T 4 (hereinafter referred to as a complete color erasing temperature) reaching a complete color erasing state
- B is a temperature T 3 (hereinafter referred to as a color erasing start temperature) at which a complete color development state can be maintained
- C is a point indicating a density at a temperature T 2 (hereinafter referred to as a color development start temperature) at which a completely decolored state can be maintained
- D is a temperature T 1 at which a complete color developed state is reached. This is a point indicating the density at (hereinafter referred to as a complete color development temperature).
- Discoloration temperature region is a temperature region between T 1 and T 4, the temperature range is substantially discoloration temperature region between T 2 and T 3, i.e., a temperature range that can hold any state of the colored state or decolored state It is.
- the temperature-sensitive color-changing color memory composition in the decolored state can be cooled to a temperature not higher than the color development start temperature (T 2 ), so that the change to the color development state can be initiated.
- T 2 the color development start temperature
- T 1 the temperature of the temperature-sensitive color-changing color memory composition is raised to the decoloring start temperature (T 3 ), that state Can be maintained.
- thermochromic color memory composition in a colored state and heated to a temperature equal to or higher than the decoloring start temperature (T 3 ) to initiate a change to the decolored state.
- the complete decoloring temperature was (T 4) can be a complete decolored state by heating to a temperature above the temperature of the color development initiation temperature of the thermochromic coloring color-memory composition (T 2) As long as it is not lowered, it can be maintained.
- the length of the line segment EF is a scale indicating the discoloration contrast
- the length of the line segment HG is a temperature width indicating the degree of hysteresis (hereinafter referred to as hysteresis width, expressed as ⁇ H).
- hysteresis width a temperature width indicating the degree of hysteresis (hereinafter referred to as hysteresis width, expressed as ⁇ H).
- the ⁇ H value that can be maintained in each state before and after the color change is 8 ° C. or more, and specifically in the range of 8 ° C. to 80 ° C.
- ⁇ t which is the difference between T 4 and T 3 , or the difference between T 2 and T 1
- is a scale indicating the sensitivity of discoloration preferably in the range of 1 ° C. to 15 ° C., more preferably 1 ° C. to A
- the complete decoloring temperature (T 4 ) is preferably 40 ° C. or higher, more preferably 50 ° C. or higher, and still more preferably 60.
- the color development start temperature (T 2 ) is preferably 0 ° C. or lower, more preferably ⁇ 5 ° C. or lower, and further preferably ⁇ 10 ° C. or lower.
- the component (a) of the present invention that is, the electron donating color-forming organic compound is a component that determines the color and is a compound that develops color by donating electrons to the component (b) that is a developer.
- Examples of the component (a) in the present invention include phthalide compounds, fluoran compounds, styrinoquinoline compounds, diazarhodamine lactone compounds, pyridine compounds, quinazoline compounds, and bisquinazoline compounds. Of these, phthalide compounds and fluoran compounds are preferred.
- Examples of the phthalide compounds include diphenylmethane phthalide compounds, phenyl indolyl phthalide compounds, indolyl phthalide compounds, diphenyl methane azaphthalide compounds, phenyl indolyl azaphthalide compounds, and derivatives thereof. , Phenyl indolyl azaphthalide compounds, and derivatives thereof are preferred.
- Examples of the fluorane compound include aminofluorane compounds, alkoxyfluorane compounds, and derivatives thereof.
- the phenyl group forming the xanthene ring has a substituent and also in the phenyl group forming the lactone ring (for example, It may be a blue or black compound having an alkyl group such as a methyl group or a halogen atom such as a chloro group.
- the component (b) of the present invention that is, the electron-accepting compound, is a compound that receives electrons from the component (a) and functions as a developer of the component (a).
- electron-accepting compounds include compounds having active protons and derivatives thereof, pseudo-acidic compounds (a group of compounds that are not acids but act as acids in the composition to cause coloration of component (a)), electron vacancies There are compounds selected from a group of compounds having a proton, etc., and among these, compounds selected from a group of compounds having an active proton are preferred.
- Examples of compounds having active protons and derivatives thereof include compounds having phenolic hydroxyl groups and metal salts thereof, carboxylic acids and metal salts thereof, preferably aromatic carboxylic acids, aliphatic carboxylic acids having 2 to 5 carbon atoms and the like.
- Metal salts, acidic phosphoric acid esters and metal salts thereof, azole compounds and derivatives thereof, 1,2,3-triazoles and derivatives thereof, and among these, effective thermochromic properties should be expressed. Therefore, a compound having a phenolic hydroxyl group is preferable.
- Compounds having a phenolic hydroxyl group are widely included from monophenol compounds to polyphenol compounds, and also include bis-type or tris-type phenols and phenol-aldehyde condensation resins.
- the compounds having a phenolic hydroxyl group those having at least two benzene rings or those having a bishydroxyphenyl sulfide structure are preferred.
- These compounds may have a substituent, and examples of the substituent include an alkyl group, an aryl group, an acyl group, an alkoxycarbonyl group, a carboxy group and an ester or amide group thereof, and a halogen group.
- Examples of the compound having a phenolic hydroxyl group include monophenols to polyphenols, and further have an alkyl group, an aryl group, an acyl group, an alkoxycarbonyl group, a carboxy group and an ester or amide group thereof, a halogen group, and the like as substituents. And bis-type, tris-type phenols, phenol-aldehyde condensation resins and the like. Moreover, the metal salt of the compound which has a phenolic hydroxyl group may be sufficient.
- Examples of the metal contained in the metal salt of the compound having an active proton include sodium, potassium, calcium, zinc, zirconium, aluminum, magnesium, nickel, cobalt, tin, copper, iron, vanadium, titanium, lead and molybdenum. .
- the compound having a phenolic hydroxyl group include phenol, o-cresol, tertiary butylcatechol, nonylphenol, n-octylphenol, n-dodecylphenol, n-stearylphenol, p-chlorophenol, p-bromophenol, o -Phenylphenol, n-butyl p-hydroxybenzoate, n-octyl p-hydroxybenzoate, resorcin, dodecyl gallate, 4,4-dihydroxydiphenyl sulfone, bis (4-hydroxyphenyl) sulfide, 1,1-bis (4-hydroxyphenyl) ethane, 1,1-bis (4-hydroxyphenyl) propane, 1,1-bis (4-hydroxyphenyl) n-butane, 1,1-bis (4-hydroxyphenyl) n-pentane 1,1-bis (4- Droxyphenyl) n-hexane
- a temperature-sensitive color-changing color memory composition having a color change temperature can be obtained.
- the ester compound used in the present invention has the formula (1): It can be obtained by etherifying the phenolic hydroxyl group of p-hydroxybenzoic acid ester (parabens) with a phenoxyethyl group or the like.
- R in the formula is any one of an alkyl group having 3 to 18 carbon atoms, a cycloalkylalkyl group having 6 to 11 carbon atoms, a cycloalkyl group having 5 to 7 carbon atoms, and an alkenyl group having 3 to 18 carbon atoms.
- X in the formula is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, or a halogen atom, preferably a hydrogen atom, a methyl group, an ethyl group, a methoxy group, Or an ethoxy group, more preferably a hydrogen atom, a methyl group, or a methoxy group.
- Each X may be the same or different.
- Y in the formula is any one of a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a methoxy group, an ethoxy group, or a halogen atom, preferably any one of a hydrogen atom, a methyl group, an ethyl group, or a methoxy group. And more preferably a hydrogen atom, a methyl group, or a methoxy group.
- Each Y may be the same or different.
- ester compound represented by the formula (1) Specific examples of the ester compound represented by the formula (1) are shown below.
- the temperature-sensitive color-changing color memory composition according to the present invention includes a specific ester compound, so that a wide hysteresis width comparable to or greater than that of a composition using a conventional ester compound can be achieved. It has an excellent function of selectively retaining either a lower temperature color or a higher temperature color, and is excellent in applicability to various applications.
- the content thereof is preferably 1 to 30 parts by mass, more preferably 2 to 25 parts by mass with respect to the total mass of the component (c). More preferably, it is 3 to 20 parts by mass.
- the composition ratio of the components (a), (b), and (c) in the present invention depends on the concentration, the color change temperature, the color change form, and the type of each component.
- the component ratio at which desired characteristics are obtained is as follows.
- component 1 preferably (b) component 0.1-50, more preferably 0.5-20, still more preferably 2-20, preferably (c) component 1-800, more preferably Is in the range of 5 to 200, more preferably 10 to 200 (all of the above ratios are in parts by mass).
- the components (a), (b), and (c) in the present invention may be a mixture of two or more.
- the component (c) in the present invention may comprise two or more compounds satisfying the formula (1).
- component (c) is an electron transfer reaction by components (a) and (b), which are conventionally known, such as esters, alcohols, carboxylic acids, ketones and amides other than the formula (1), in a specific temperature range. It can also be used in combination with a reaction medium that occurs reversibly.
- the three components (a), (b), and (c) can be encapsulated in a microcapsule to form a thermosensitive color-changing color memory microcapsule pigment, which is protected by a capsule membrane wall. It is possible to improve the heat resistance stability as well as not to lower the function even if it comes into contact with chemically active substances such as acidic substances, basic substances, peroxides or other solvent components. it can.
- a secondary resin film may be provided on the surface of the microcapsule pigment according to the purpose to impart durability, or the surface characteristics may be modified for practical use.
- the microcapsule pigment preferably has an average particle size of 0.1 to 50 ⁇ m, more preferably 0.1 to 30 ⁇ m, and particularly preferably 0.5 to 20 ⁇ m. Practicality is improved when the average particle size of the microcapsule pigment is within this range.
- the particle size and particle size distribution were measured using a laser diffraction / scattering particle size distribution measuring apparatus (manufactured by Horiba, Ltd .; LA-300), and the average particle size (median diameter) was calculated based on the numerical values. It can be calculated on a volume basis.
- Microencapsulation methods include conventionally known isocyanate-based interfacial polymerization methods, in situ polymerization methods using melamine-formalin, etc., in-liquid curing coating methods, phase separation methods from aqueous solutions, and phases from organic solvents. There are a separation method, a melt dispersion cooling method, an air suspension coating method, a spray drying method, and the like, which are appropriately selected according to the application.
- the microcapsule pigment can be mixed with a general dye (non-thermochromic property) to exhibit a color change behavior from colored (1) to colored (2).
- Temperature-sensitive color-changing color memory microcapsule pigments are dispersed in a vehicle containing additives as necessary to form an ink composition.
- Screen printing, offset printing, process printing, gravure printing, coater, tampo Printing ink used for printing (ii) Brush coating, spray coating, electrostatic coating, electrodeposition coating, flow coating, roller coating, dip coating, etc., (iii) marking pen, ballpoint pen, fountain pen Temperature-sensitive color-changing color-memory liquid composition such as ink for writing instruments such as pen, brush pen, (iv) ink for cloth, (v) paint, (vi) cosmetics, or (vii) fiber coloring liquid Available for things.
- Additives include resins, crosslinking agents, curing agents, drying agents, plasticizers, viscosity modifiers, dispersants, ultraviolet absorbers, infrared absorbers, antioxidants, light stabilizers, dissolution aids, anti-settling agents, Examples include a smoothing agent, a gelling agent, an antifoaming agent, a matting agent, a penetrating agent, a pH adjusting agent, a foaming agent, a coupling agent, a moisturizing agent, a fungicide, an antiseptic, and a rust inhibitor.
- the vehicle contained in the ink composition is an oil-based vehicle containing an organic solvent, or water and necessary.
- organic solvent examples 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, - it can be exemplified methyl-2-pyrrolidone.
- the ink examples include a shear-thinning ink containing a shear-thinning agent in the vehicle, and a cohesive ink containing a water-soluble polymer flocculant in the vehicle and suspending the pigment in a gentle aggregation state.
- the ink contains a shear thinning agent, it is possible to suppress aggregation and sedimentation of the pigment, and it is possible to suppress bleeding of the handwriting, thereby forming a good handwriting.
- shear thinning agent examples include xanthan gum, welan gum, succinoglycan (average molecular weight of about 1 to 8 million) whose constituent monosaccharide is an organic acid-modified heteropolysaccharide of glucose and galactose, guar gum, locust bean gum and derivatives thereof , Hydroxyethyl cellulose, alginic acid alkyl esters, polymers having a molecular weight of 100,000 to 150,000, mainly composed of alkyl esters of methacrylic acid, and a thickening gel having gelling ability extracted from seaweeds such as glucomannan, agar and carrageenan Sugars, benzylidene sorbitol and benzylidene xylitol or their derivatives, crosslinkable acrylic acid polymer, inorganic fine particles, polyglycerin fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyethylene glycol fatty acid ester, polio Shi ethylene al
- water-soluble polymer flocculant examples include polyvinyl pyrrolidone, polyethylene oxide, and water-soluble polysaccharides.
- water-soluble polysaccharides examples include tragacanth gum, guar gum, pullulan, cyclodextrin, water-soluble cellulose derivatives, etc.
- water-soluble cellulose derivatives include methyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxyethyl methyl cellulose, hydroxypropyl methyl cellulose, etc. Is mentioned.
- the comb polymer dispersant having a carboxyl group in the side chain is not particularly limited as long as it is a comb polymer compound having a plurality of carboxyl groups in the side chain.
- An acrylic polymer compound having a suitable product is exemplified, and trade name: Solsperse 43000 manufactured by Nippon Lubrizol Corporation can be exemplified.
- Organic nitrogen sulfur compound further suppresses settling of microcapsule pigment due to vibration when ink is filled into a writing instrument and put to practical use. This further improves dispersibility in which loose aggregates of microcapsule pigments are dispersed by a comb-type polymer dispersant having a carboxyl group in the side chain.
- organic nitrogen sulfur compound a compound selected from thiazole compounds, isothiazole compounds, benzothiazole compounds, and benzoisothiazole compounds is used.
- organic nitrogen sulfur compound examples include 2- (4-thiazoyl) -benzimidazole (TBZ), 2- (thiocyanatomethylthio) -1,3-benzothiazole (TCMTB), 2-methyl-4-isothiazoline-3
- TZ 2- (4-thiazoyl) -benzimidazole
- TCMTB 2- (thiocyanatomethylthio) -1,3-benzothiazole
- 2-methyl-4-isothiazoline-3 One or more compounds selected from -one and 5-chloro-2-methyl-4-isothiazolin-3-one are used, preferably 2- (4-thiazoyl) -benzimidazole (TBZ), 2- One or more compounds selected from methyl-4-isothiazolin-3-one and 5-chloro-2-methyl-4-isothiazolin-3-one are used.
- the mass ratio of the comb polymer dispersant having a carboxyl group in the side chain and the organic nitrogen sulfur compound is preferably 1: 1 to 1:10, and preferably 1: 1 to 1: 5. More preferred.
- a water-soluble resin it is possible to impart to the ink pigment adhesion and viscosity to the paper surface of the handwriting.
- This water-soluble resin also has an effect of further improving the stability of the microcapsule pigment in the ink containing the comb polymer dispersant having a carboxyl group in the side chain and the organic nitrogen sulfur compound.
- water-soluble resin examples include alkyd resin, acrylic resin, styrene maleic acid copolymer, cellulose derivative, polyvinyl pyrrolidone, polyvinyl alcohol, dextrin, and preferably polyvinyl alcohol is used.
- a partially saponification type polyvinyl alcohol having a saponification degree of 70 to 89 mol% is more preferably used because it is highly soluble even in an acidic pH range.
- the addition amount of the water-soluble resin is 0.3 to 3.0% by mass, preferably 0.5 to 1.5% by mass in the ink.
- higher fatty acids such as oleic acid, nonionic surfactants having a long chain alkyl group, polyether-modified silicone oil, thiophosphorous acid tri (alkoxycarbonylmethyl ester) and thio Thiophosphorous acid triesters such as phosphorous acid tri (alkoxycarbonylethyl ester), phosphoric acid monoester of polyoxyethylene alkyl ether or polyoxyethylene alkyl aryl ether, polyoxyethylene alkyl ether or polyoxyethylene alkyl aryl ether phosphoric acid It is preferable to prevent wear of the ball seat by adding a lubricant such as a diester or a metal salt, an ammonium salt, an amine salt, or an alkanolamine salt thereof.
- a lubricant such as a diester or a metal salt, an ammonium salt, an amine salt, or an alkanolamine salt thereof.
- acrylic resin styrene-maleic acid copolymer, cellulose derivative, polyvinyl pyrrolidone, polyvinyl alcohol, dextrin and other resins that provide adhesion and viscosity to the paper surface,
- sodium carbonate PH adjusters such as inorganic salts such as sodium phosphate and sodium acetate, organic basic compounds such as water-soluble amine compounds,
- Rust (iv) phenol, sodium salt of 1,2-benzthiazolin-3-one, sodium benzoate, sodium dehydroacetate, potassium sorbate, propyl paraoxybenzoate, 2,3,5,6-tetrachloro-4 -(Methylsulf Nyl) pyridine and other preservatives or antifungal agents, (v) urea, nonionic surfactants, reduced or non-reduced starch hydrolysates, oligosaccharides such as trehalose, sucrose, cyclodextrin, glucose, dextrin, sorbit, Add humectants such as mannitol, sodium pyrophosphate, (vi) antifoaming agents, (vii) dispersants, (viii) fluorine-based surfactants and nonionic surfactants that improve ink permeability. Also good.
- thermosensitive color-changing color memory microcapsule pigment may be contained in an amount of preferably 5 to 40% by mass, more preferably 10 to 40% by mass, and still more preferably 10 to 30% by mass with respect to the total mass of the ink.
- content of the microcapsule pigment is within the above range, a desired color density can be achieved, and further, the ink outflow can be prevented from being lowered.
- the writing instrument includes a shaft cylinder containing ink and a pen body for deriving ink in the shaft cylinder.
- the pen body include a marking pen body, a ballpoint pen body, and a brush pen body.
- the marking pen body include marking tips such as fiber tips, felt tips, and plastic tips.
- An example of the ballpoint pen body is a ballpoint pen tip.
- a brush pen body a fiber bundling body in which fibers are bundled closely in the longitudinal direction, a plastic porous body having continuous pores, a heat-bonded or resin processed body of synthetic resin fibers, an extrusion molding process of a soft resin or an elastomer The body is mentioned.
- the structure and shape of the ballpoint pen itself are not particularly limited.
- the ink pendant has an ink containing tube filled with shear-thinning ink in a shaft tube, and the ink containing tube Can be exemplified by a ballpoint pen that communicates with a ballpoint pen tip having a ball attached to the tip, and a liquid stopper for backflow prevention is in intimate contact with the end face of the ink in the receiving tube.
- the ballpoint pen tip will be described in more detail.
- a chip formed by holding a ball in the formed ball holding part, a chip provided with a resin ball receiving seat inside a metal or plastic chip, or a ball held by the chip is urged forward by a spring body Applicable ones can be applied.
- the ball may be made of cemented carbide, stainless steel, ruby, ceramic, resin, rubber or the like.
- the ball diameter is preferably 0.3 to 2.0 mm, more preferably 0. .3 to 1.5 mm, more preferably 0.3 to 1.0 mm.
- the ink storage tube for storing ink for example, a molded body made of a thermoplastic resin such as polyethylene, polypropylene, polyethylene terephthalate, nylon, or a metal tubular body is used.
- a thermoplastic resin such as polyethylene, polypropylene, polyethylene terephthalate, nylon, or a metal tubular body is used.
- the ink storage tube and the chip may be connected via a connecting member.
- the ink storage tube may be a refill type in which the refill is accommodated in a shaft cylinder made of resin, metal, or the like.
- the cylinder may be filled directly with ink.
- the ballpoint pen may be provided with a cap that covers the ballpoint pen tip, or may be a retractable ballpoint pen that is not provided with a cap.
- the structure and shape of the retractable ballpoint pen are not particularly limited, and the writing tip provided on the ballpoint pen refill is exposed to the outside air in the shaft cylinder. Any structure can be used as long as it is housed and the writing tip protrudes from the opening of the shaft cylinder by the operation of the retracting mechanism.
- the haunting ballpoint pen can be classified into, for example, a knocking ballpoint pen, a rotating ballpoint pen, a sliding ballpoint pen, and the like.
- the knock-type ballpoint pen has a knock portion at the rear end portion of the shaft tube and the side surface of the shaft tube, and a configuration in which the ballpoint pen tip is projected and retracted from the front end opening portion of the shaft tube by pressing the knock portion, or a clip portion provided on the shaft tube.
- the structure which makes a ball-point pen tip protrude and invade from a shaft cylinder front-end opening part by pressing can be illustrated.
- the rotary ballpoint pen has a rotating part at the rear part of the shaft cylinder, and a configuration in which the ballpoint pen tip is projected and retracted from the opening part at the front end of the shaft cylinder by turning the rotating part can be exemplified.
- the slide-type ballpoint pen has a slide part on the side surface of the shaft cylinder, and by operating the slide, the configuration in which the ballpoint pen tip protrudes and appears from the front end opening of the shaft cylinder, or by sliding the clip part provided on the shaft cylinder, A configuration in which the ball-point pen tip is projected and retracted from the front end opening of the shaft cylinder can be exemplified.
- a retractable ballpoint pen is a compound type retractable ballpoint pen that contains a plurality of ballpoint pen refills in a shaft cylinder, and the writing tip of any ballpoint pen refill appears and disappears from the front end opening of the shaft cylinder by the operation of the retractable mechanism. Also good.
- an ink backflow prevention body is filled in the end face of the rear end of the ink stored in the ink storage tube.
- the ink backflow preventive composition is composed of a non-volatile liquid or a hardly volatile liquid.
- a non-volatile liquid or a hardly volatile liquid.
- petroleum jelly spindle oil, castor oil, olive oil, refined mineral oil, liquid paraffin, polybutene, ⁇ -olefin, ⁇ -olefin oligomer or co-oligomer, dimethyl silicone oil, methylphenyl silicone oil, amino-modified silicone oil, Examples thereof include polyether-modified silicone oil and fatty acid-modified silicone oil, and one or more can be used in combination.
- the non-volatile liquid and / or the hardly volatile liquid is preferably thickened to a suitable viscosity by adding a thickener.
- a thickener silica whose surface has been subjected to hydrophobic treatment, and fine particle silica whose surface has been methylated.
- liquid ink backflow prevention body and a solid ink backflow prevention body can be used in combination.
- the structure and shape of the marking pen itself are not particularly limited.
- an ink occlusion body composed of a fiber bundling body is incorporated in the shaft cylinder, and the capillary gap
- a marking pen tip made of a fiber processed body formed with an ink occlusion is attached to the shaft cylinder directly or via a relay member, and the ink occlusion body of the marking pen formed by connecting the ink occlusion body and the tip is impregnated with cohesive ink.
- Examples thereof include a marking pen, a marking pen in which a chip and an ink storage tube are arranged via a valve body opened by pressing of the chip, and ink is directly stored in the ink storage tube.
- the chip is a porous member having continuous air holes selected from the range of generally used porosity of 30 to 70%, such as a fiber resin processed body, a heat-fusible fiber bonded body, and a felt body. Is processed into a shape suitable for the purpose such as a bullet shape, rectangular shape, chisel shape, etc.
- the ink occlusion body is formed by converging crimped fibers in the longitudinal direction, and is configured to be contained in a covering body such as a plastic cylinder or a film so that the porosity is adjusted in a range of approximately 40 to 90%.
- valve body can be of a general-purpose pumping type from the past, but is preferably set to a spring pressure that can be pressed and released by writing pressure.
- the form of the ballpoint pen or the marking pen is not limited to the one described above, and it may be a double-headed writing instrument on which a tip having a different shape is attached or a pen tip for deriving different colors of ink is attached.
- the handwriting obtained by writing on a writing surface using the writing instrument which accommodated the ink by this invention can be discolored with a heating tool or a cooling tool.
- the heating tool examples include a heating color changing tool equipped with a resistance heating element, a heating color changing tool filled with warm water, and a hair dryer.
- a friction member is used as a means capable of changing color by a simple method. It is done.
- an elastic body that does not substantially wear during rubbing is preferable.
- an elastic body such as an elastomer or a plastic foam which is rich in elasticity and can generate frictional heat upon rubbing to generate frictional heat is preferable.
- silicone resin silicone resin, SEBS resin (styrene ethylene butadiene styrene block copolymer), polyester resin or the like is used.
- the friction member can be obtained by combining a writing instrument and a member of an arbitrary shape (friction body) separately to obtain a writing instrument set, but by providing the writing instrument with a friction member, it is excellent in portability.
- the location where the friction member is provided is not particularly limited.
- the cap itself is formed of a friction member
- the shaft tube itself is formed of a friction member, or a clip is provided.
- the clip itself can be formed of a friction member, or the friction member can be provided at the tip end (top) of the cap or the rear end of the shaft cylinder (the portion where the writing tip is not provided).
- the location where the friction member is provided is not particularly limited, but for example, the shaft cylinder itself is formed with a friction member, or when the clip is provided, the clip itself is formed with a friction member, A friction member can be provided in the vicinity of the shaft tube opening, the rear end portion of the shaft tube (the portion where the writing tip portion is not provided) or the knock portion.
- Cooling tools include cooling / changing tools using Peltier elements, cooling / changing tools filled with refrigerants such as cold water and ice pieces, refrigerators and freezers.
- the material of the support is not specified and is all effective, and is paper, synthetic paper, fiber, fabric, synthetic leather, leather, plastic, glass, A ceramic material, a metal, wood, a stone material, etc. can be illustrated, and not only a planar shape but uneven
- a laminate (printed material) is obtained by providing a reversible thermochromic layer containing a temperature-sensitive color-changing color memory composition on a support.
- the colored layer can be concealed by a reversible thermochromic layer due to a temperature change, and the aspect of the change can be changed. It can be further diversified.
- thermochromic color memory microcapsule pigment is melt-blended into a thermoplastic resin, thermosetting resin, wax, or the like, and the thermosensitive color-changing color memory molding resin composition in the form of pellets, powder, or paste. It can also be used as a product, and can be used as a general-purpose injection molding, extrusion molding, blow molding, cast molding, or any other form of three-dimensional modeled object, film, sheet, plate, filament, rod, pipe, etc. A molded body is obtained.
- a crayon can be obtained by melt blending with a thermoplastic resin or wax.
- a general dyeing pigment non-thermochromic property
- blended blended, and the color change behavior from colored (1) to colored (2) can also be exhibited.
- light stabilizers examples include ultraviolet absorbers, antioxidants, singlet oxygen quenchers, superoxide anion quenchers, and ozone quenchers.
- the transparent metallic luster pigment examples include natural mica, synthetic mica, glass pieces, alumina, and a pigment obtained by coating the surface of a transparent film piece with a metal oxide such as titanium oxide.
- Specific examples of the product using the temperature-sensitive color-changing color memory composition and the temperature-sensitive color-changing color memory microcapsule pigment and the ink containing the composition include the following.
- Toys for dolls or animal figure toys, hair for dolls or animal figure toys, accessories for dolls such as doll houses and furniture, clothing, hats, bags and shoes, accessory toys, plush toys, drawing toys, for toys
- Puzzle toys such as picture books, jigsaw puzzles, building toys, block toys, clay toys, fluid toys, tops, kites, musical instrument toys, cooking toys, gun toys, capture toys, background toys and vehicles, animals, plants, buildings, and food
- toys Clothing T-shirts, trainers, blouses, dresses, swimwear, raincoats, skiwear, and other clothing, footwear such as shoes and shoelaces, handkerchiefs, towels, cloth accessories such as furoshiki, gloves, ties, and hats etc, (3) Indoor decoration carpets, curtains, curtain strings, table racks, rugs, cushions, picture frames, artificial flowers, photo frames,
- Examples of the present invention are shown below, but the present invention is not limited thereto.
- the part in an Example represents a mass part.
- Example 1 Method for preparing temperature-sensitive color-change color memory composition
- component (1) 2- (2-chloroanilino) -6-di-n-butylaminofluorane,
- component (c) three components consisting of 50 parts of p-hydroxybenzoic acid nonyl phenoxyethyl ether (Compound 4) were mixed and heated to dissolve homogeneously.
- a thermochromic color memory composition was obtained.
- This temperature-sensitive color-changing color memory composition changed from black to colorless.
- the temperature-sensitive color-changing color memory composition was sealed in a transparent glass capillary tube having an inner diameter of 1 mm and a length of 78 mm to a height of about 10 mm from the bottom of the capillary tube to obtain a measurement sample.
- the temperature-sensitive color change color memory composition of the measurement sample is immersed in the transparent heat medium while the temperature-sensitive color change color memory composition of the measurement sample is encapsulated, and the temperature of the transparent heat medium is changed.
- the discoloration state was visually observed, and T 1 (complete color development temperature), T 2 (color development start temperature), T 3 (color erase start temperature), T 4 (complete color erase temperature) were measured, and T H [ T 1 and T 2 intermediate temperature (T 1 + T 2 ) / 2], T G [T 3 and T 4 intermediate temperature (T 3 + T 4 ) / 2], ⁇ H (hysteresis width T G ⁇ T H )
- Thermochromic coloring color-memory composition of Example 1 is T 1: 15 °C, T 2 : 19 °C, T 3: 42 °C, T 4: 52 °C, T H: 17 °C, T G: 47 °C, ⁇ H:
- the hysteresis characteristic at 30 ° C. was shown
- Examples 2-4 The temperature-sensitive color-changing color memories of Examples 2 to 4 were the same as Example 1 except that the components (a) and (c) of the temperature-sensitive color-changing color memory composition described in the following table were changed. The color change temperature was measured in the same manner as in Example 1.
- P of component (a) is 2- (2-chloroanilino) -6-di-n-butylaminofluorane
- Q is 1,2-benz-6- (N-ethyl-N-isoamylamino) ) Fluorane and R is 3- (2-ethoxy-4-diethylaminophenyl) -3- (1-ethyl-2-methylindol-3-yl) -4-azaphthalide.
- the unit of a compounding quantity is a mass part in a table
- the following table shows the color change, T 1 , T 2 , T 3 , T 4 , T H , T G , and ⁇ H values of the temperature-sensitive color-changing color memory compositions of Examples 1 to 4.
- thermosensitive color-changing color memory microcapsule pigment (a) 3- (2-Ethoxy-4-diethylaminophenyl) -3- (1-ethyl-2-methylindol-3-yl) -4- as component (a) 1 part of azaphthalide, 5 parts of 2,2-bis (4-hydroxyphenyl) hexafluoropropane as component (b), 50 parts of phenoxyethyl ether of p-hydroxybenzoate (compound 4) as component (c) and stearic acid
- a temperature-sensitive color-changing color memory composition comprising 3 parts of p-methylbenzyl was mixed and uniformly heated and dissolved, and further 20 parts of an aromatic polyvalent isocyanate prepolymer and 40 parts of ethyl acetate were mixed as a wall film material. The solution was put into 100 parts of a 15% gelatin aqueous solution and emulsified and dispersed so as to form fine droplets.
- the temperature-sensitive color-changing color memory microcapsule pigment was isolated from the microcapsule pigment suspension by centrifugation to obtain a temperature-sensitive color-changing color memory microcapsule pigment that changes from blue to colorless (average particle size 2). .2 ⁇ m).
- thermosensitive color-changing color memory microcapsule pigment 50 parts of ethylene-vinyl acetate resin emulsion, 1 part of leveling agent, 1 part of antifoaming agent, 0.5 part of viscosity modifier, 7.5 parts of water
- a temperature-sensitive color-change color memory ink was prepared by uniformly dispersing in a water-based ink vehicle consisting of parts. A solid pattern was screen-printed on high-quality paper with this ink to obtain a measurement sample.
- Temperature-sensitive color-changing color memory microcapsule pigments are T 1 : -19 ° C, T 2 : -9 ° C, T 3 : 40 ° C, T 4 : 54 ° C, T H : -14 ° C, T G : 47 ° C, ⁇ H: A hysteresis characteristic of 61 ° C. was exhibited.
- thermochromic color-memory composition to be encapsulated in the microcapsule was prepared from 50 parts of phenoxyethyl ether of p-hydroxybenzoic acid nonyl (compound 4) and 3 parts of p-methylbenzyl stearate to p-hydroxy.
- a thermochromic microcapsule pigment was prepared in the same manner as in Example 5 except that it was changed to 50 parts of undecyl benzoate phenoxyethyl ether (Compound 6). Capsule pigments were obtained (average particle size 1.8 ⁇ m).
- the temperature-sensitive color-changing color memory microcapsule pigment was T 1 : ⁇ 24 ° C., T 2 : ⁇ 6 ° C., T 3 : 48 ° C., T 4 : 58 ° C. , T H : ⁇ 15 ° C., T G : 53 ° C., ⁇ H: 68 ° C.
- thermosensitive color-changing color-memory microcapsule pigment prepared in Example 6 previously cooled to ⁇ 24 ° C. or less to develop a blue color
- succinoglycan saliva thinning agent
- sugar mixture [manufactured by Sanwa Starch Co., Ltd., trade name: Sandeck 70] 3.0 parts, phosphate ester surfactant 0.5 part, antifungal agent 0.1 part, triethanolamine 1.0 Part of water and 68.1 parts of water were uniformly dispersed in a vehicle to prepare a thermochromic color-memory liquid composition (ink for writing instruments).
- a viscoelastic ink backflow prevention body (liquid stopper) mainly composed of polybutene was filled from the rear end of the polypropylene pipe to obtain a ballpoint pen refill.
- a ballpoint pen refill was incorporated into the shaft tube to obtain a writing instrument (intrusion ballpoint pen).
- the writing instrument is housed in the shaft cylinder in a state where the tip provided on the ballpoint pen refill is exposed to the outside air, and the shaft cylinder is activated by the operation of a clip-shaped protrusion / distraction mechanism (slide mechanism) provided on the side surface of the shaft cylinder.
- the chip protrudes from the front end opening.
- a friction member made of SEBS resin is provided at the rear end of the shaft tube.
- the blue pen (handwriting) was formed by writing on the paper with the tip of the ballpoint pen tip protruding from the front end opening of the barrel by the operation of the protrusion mechanism.
- Application example 2 27 parts of temperature-sensitive color-changing color-memory microcapsule pigment prepared in Example 5 (previously cooled to -19 ° C. or lower and colored blue) 0.33 parts of xanthan gum (shear thinning agent), A water-based ink vehicle comprising 10.0 parts urea, 10 parts glycerin, 0.6 parts nonionic surfactant, 0.1 part modified silicone antifoaming agent, 0.2 part antifungal agent, and 51.77 parts water.
- a temperature-sensitive color-changing color-memory liquid composition was prepared by uniformly dispersing.
- a viscoelastic ink backflow prevention body (liquid stopper) mainly composed of polybutene is filled, and a tail plug is fitted to the rear part of the pipe.
- a deaeration process was performed by centrifugation to obtain a writing instrument (ballpoint pen).
- SEBS rubber is mounted as a friction body at the rear part of the rear shaft cylinder.
- a blue letter was formed by writing on the paper using a writing instrument.
- the handwriting showed a blue color at room temperature (25 ° C.), and when the letters were scraped with a friction body, the letters disappeared and became colorless, and this state could be maintained at room temperature.
- Application example 3 25 parts of temperature-sensitive color-changing color-memory microcapsule pigment prepared in Example 6 (previously cooled to -24 ° C. or less to develop blue color), 0.5 part of hydroxyethyl cellulose, comb-type polymer dispersant [ Nippon Lubrizol Co., Ltd., trade name: Solsperse 43000, 0.2 parts, organic nitrogen sulfur compound [Hokuside Chemical Co., Ltd., trade name: Hokuside R-150, 2-methyl-4-isothiazolin-3-one Mixture of 5-chloro-2-methyl-4-isothiazolin-3-one] 1.0 part, 0.5 part polyvinyl alcohol, 25.0 parts glycerin, 0.02 part antifoaming agent, 47.78 parts water The mixture was mixed to obtain a temperature-sensitive color-changing color memory liquid composition (ink for writing instruments).
- a blue letter was formed by writing on the paper using a writing instrument.
- the handwriting showed a blue color at room temperature (25 ° C.), and when the letters were scraped with a friction body, the letters disappeared and became colorless, and this state could be maintained at room temperature.
- thermochromic color memory microcapsule pigment prepared in Example 6 2.5 parts were added to 12.5 parts of a vinyl chloride-vinyl acetate copolymer resin and 38 parts of xylene.
- a temperature-sensitive color-changing color memory liquid composition was prepared by uniformly dispersing in an oil-based ink vehicle comprising 3 parts, 45 parts of butyl acetate and 0.2 part of a viscosity modifier.
- spray coating is applied to the plug part (white) of household electric cords to provide a reversible thermochromic layer, and a temperature-sensitive color-changing color memory plug Obtained.
- the plug had a purple color at room temperature (25 ° C), but became pink at a temperature of 58 ° C or higher by heating. When cooled from this discolored state, it turned purple again at a temperature of ⁇ 24 ° C. or lower.
- the temperature-sensitive color change color memory plug When the temperature-sensitive color change color memory plug becomes pink at a temperature of 58 ° C or higher, it can maintain a pink color change state unless it is cooled to a temperature of -24 ° C or lower.
- the temperature history when reaching a high temperature range of 58 ° C. or higher could be detected visually.
- Application example 5 30 parts of temperature-sensitive color-changing color-memory microcapsule pigment prepared in Example 5 (previously cooled to -19 ° C. or lower and colored blue) 60 parts of acrylic resin emulsion (solid content 45%), viscosity
- a temperature-sensitive color-changing color-memory liquid composition was prepared by uniformly dispersing in an aqueous ink vehicle comprising 1 part of an adjusting agent, 0.2 part of an antifoaming agent and 8.8 parts of water.
- a number of star patterns were screen-printed on a white T-shirt (cotton) using a 100-mesh screen version using ink to obtain a temperature-sensitive color-change color memory T-shirt.
- a part of the star pattern on the surface of the T-shirt is erased by heating with an iron or the like, and a pattern in which only an arbitrary star pattern is erased or a letter or pattern is formed with the star pattern. It was possible to change.
- the discolored state can be maintained at room temperature, and the whole is heated to 54 ° C or higher to completely erase the star pattern, and then cooled to -19 ° C or lower to recolor the star pattern. I was able to.
- thermosensitive color-changing color memory microcapsule pigment prepared in Example 6 1 part of dispersant, 0.1 part of non-thermochromic pink pigment, and 93.9 parts of polypropylene homopolymer were 180 ° C. using an extruder.
- the resin composition for molding (pellet) was obtained by melt-mixing.
- a plastic cup was molded with an injection molding machine at a cylinder temperature of 180 ° C.
- This cup turns purple when cooled to -24 ° C or below, and is purple even when left at room temperature (25 ° C), but when a beverage above 58 ° C is poured, the place where the beverage is put is pink Became. When the beverage was removed and cooled to ⁇ 24 ° C. or lower, the portion that turned pink turned purple again.
- Application example 7 20 parts of the temperature-sensitive color-changing color-memory microcapsule pigment prepared in Example 5 (previously cooled to -19 ° C. or less to develop a blue color) was added to an acrylic resin emulsion (solid content 40%) 78.0.
- a temperature-sensitive color-changing color memory liquid composition (printing ink) was prepared by uniformly dispersing in a water-based ink vehicle comprising 2.0 parts of an antifoaming agent.
- a counterfeit discrimination mark was printed by gravure printing on a gift certificate printed on high-quality paper using non-thermochromic ink using temperature-sensitive color-changing color memory ink.
- the counterfeit discrimination mark is blue at room temperature (25 ° C.) and does not change color at body temperature or ambient temperature, but becomes colorless when heated to 54 ° C. or higher, and turns blue again when cooled to ⁇ 19 ° C. or lower.
- the counterfeit identification mark on the gift certificate is blue and does not change color at room temperature, so it cannot be identified as a counterfeit identification mark. However, since it becomes colorless when heated to 54 ° C or higher, it has a forgery prevention function. It was.
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Abstract
Description
本発明は、(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、(c)前記(a)成分および前記(b)成分の呈色反応をコントロールする反応媒体として、下記式(1)で示されるエステル化合物と、を含んでなる感温変色性色彩記憶性組成物に関するものである。
さらに本発明は、前記のマイクロカプセル顔料と、ビヒクルとを含んでなるインキ組成物にも関するものである。
図1において、縦軸に色濃度、横軸に温度が表されている。温度変化による色濃度は矢印に沿って変化する。ここで、Aは完全消色状態に達する温度T4(以下、完全消色温度と称す)における濃度を示す点であり、Bは完全発色状態を保持できる温度T3(以下、消色開始温度と称す)における濃度を示す点であり、Cは完全消色状態を保持できる温度T2(以下、発色開始温度と称す)における濃度を示す点であり、Dは完全発色状態に達する温度T1(以下、完全発色温度と称す)における濃度を示す点である。
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。
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〕。
本発明に用いられるエステル化合物は、式(1):
又、本発明における(a)、(b)、および(c)成分は各々2種以上の混合であってもよい。本発明における(c)成分は、式(1)を満たす化合物を二種以上含んでなるものであってもよい。また、前記(c)成分は、式(1)以外のエステル、アルコール、カルボン酸、ケトン及びアミド等、従来より公知の、(a)成分及び(b)成分による電子授受反応を特定温度域において可逆的に生起させる反応媒体と組み合わせて用いることもできる。
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(1)玩具類
人形又は動物形象玩具、人形又は動物形象玩具用毛髪、人形の家や家具、衣類、帽子、鞄、および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、背景玩具および乗物、動物、植物、建築物、および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、および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、および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、照明器具および冷暖房器具等、
(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、およびスカーフ等時計、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、およ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、および教習具等。
各実施例における感温変色性色彩記憶性組成物及びそれを内包したマイクロカプセル顔料の製造方法と、感温変色性色彩記憶性組成物及びマイクロカプセル顔料の温度変化によるヒステリシス特性の測定方法について説明する。
なお、実施例中の部は質量部を表す。
感温変色性色彩記憶性組成物の調製方法
(a)成分として、2-(2-クロロアニリノ)-6-ジ-n-ブチルアミノフルオラン1部、(b)成分として、2,2-ビス(4-ヒドロキシフェニル)ヘキサフルオロプロパン2部、(c)成分として、p-ヒドロキシ安息香酸ノニルのフェノキシエチルエーテル(化合物4)50部からなる三成分を混合し、加温して均質に溶解して感温変色性色彩記憶性組成物を得た。
この感温変色性色彩記憶性組成物は黒色から無色に変色するものであった。
感温変色性色彩記憶性組成物を内径1mm、長さ78mmの透明ガラス製毛細管に、毛細管底部から約10mmの高さまで封入し、測定試料を得た。
測定試料の感温変色性色彩記憶性組成物を封入した部分全体を透明熱媒体の中に浸漬し、透明熱媒体の温度を変化させながら、感温変色性色彩記憶性組成物の変色状態を目視で観察して、T1(完全発色温度)、T2(発色開始温度)、T3(消色開始温度)、T4(完全消色温度)を測定し、TH〔T1とT2の中間の温度(T1+T2)/2〕、TG〔T3とT4の中間の温度(T3+T4)/2〕、ΔH(ヒステリシス幅TG-TH)を求めた。
実施例1の感温変色性色彩記憶性組成物はT1:15℃、T2:19℃、T3:42℃、T4:52℃、TH:17℃、TG:47℃、ΔH:30℃のヒステリシス特性を示した。
以下の表に記載した感温変色性色彩記憶性組成物の(a)成分、(c)成分を変更した以外は実施例1と同一方法で、実施例2~4の感温変色性色彩記憶性組成物を調製し、実施例1と同様にして変色温度を測定した。
感温変色性色彩記憶性マイクロカプセル顔料の調製方法
(a)成分として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1部、(b)成分として2,2-ビス(4-ヒドロキシフェニル)ヘキサフルオロプロパン5部、(c)成分としてp-ヒドロキシ安息香酸ノニルのフェノキシエチルエーテル(化合物4)50部及びステアリン酸p-メチルベンジル3部からなる感温変色性色彩記憶性組成物を混合し、均一に加温溶解し、さらに壁膜材料として芳香族多価イソシアネートプレポリマー20部、酢酸エチル40部を混合した溶液を15%ゼラチン水溶液100部中に投入し、微小滴になるように乳化分散した。
感温変色性色彩記憶性マイクロカプセル顔料40部を、エチレン-酢酸ビニル樹脂エマルジョン50部、レベリング剤1部、消泡剤1部、粘度調整剤0.5部、水7.5部からなる水性インキビヒクルに均一に分散させて感温変色性色彩記憶性インキを調製した。このインキで上質紙にベタ柄をスクリーン印刷して測定試料を得た。
測定試料を色差計(TC-3600型色差計、東京電色株式会社製)の測定部分にセットし、試料部分を10℃/分の速度で昇温、降温させ、各温度における色濃度として明度値を測定し、色濃度-温度曲線を作成した。色濃度-温度曲線よりT1、T2、T3、T4、TH〔T1とT2の中間の温度(T1+T2)/2〕、TG〔T3とT4の中間の温度(T3+T4)/2〕、ΔH(ヒステリシス幅TG-TH)を求めた。
マイクロカプセルに内包させる感温変色性色彩記憶性組成物の(c)成分をp-ヒドロキシ安息香酸ノニルのフェノキシエチルエーテル(化合物4)50部及びステアリン酸p-メチルベンジル3部から、p-ヒドロキシ安息香酸ウンデシルのフェノキシエチルエーテル(化合物6)50部に変更した以外は実施例5と同様にして感温変色性マイクロカプセル顔料を調製し、青色から無色に変色する感温変色性色彩記憶性マイクロカプセル顔料を得た(平均粒子径1.8μm)。
実施例6で調製した感温変色性色彩記憶性マイクロカプセル顔料27部(予め-24℃以下に冷却して青色に発色させたもの)を、サクシノグリカン(剪断減粘性付与剤)0.3部、糖混合物〔三和澱粉工業株式会社製、商品名:サンデック70〕3.0部、リン酸エステル系界面活性剤0.5部、防黴剤0.1部、トリエタノールアミン1.0部、水68.1部ビヒクルに均一に分散させて感温変色性色彩記憶性液状組成物(筆記具用インキ)を調製した。
インキをポリプロピレン製パイプからなるインキ収容管に吸引充填し、樹脂製ホルダーを介して0.5mmステンレス鋼ボールを先端に抱持したボールペンチップと連結させた。
実施例5で調製した感温変色性色彩記憶性マイクロカプセル顔料27部(予め-19℃以下に冷却して青色に発色させたもの)を、キサンタンガム(剪断減粘性付与剤)0.33部、尿素10.0部、グリセリン10部、ノニオン系界面活性剤0.6部、変性シリコーン系消泡剤0.1部、防黴剤0.2部、水51.77部からなる水性インキビヒクルに均一に分散させて感温変色性色彩記憶性液状組成物(筆記具用インキ)を調製した。
インキをポリプロピレン製パイプに吸引充填し、樹脂製ホルダーを介して0.5mmステンレス鋼ボールを先端に抱持したボールペンチップと連結させた。
実施例6で調製した感温変色性色彩記憶性マイクロカプセル顔料25部(予め-24℃以下に冷却して青色に発色させたもの)、ヒドロキシエチルセルロース0.5部、櫛型高分子分散剤〔日本ルーブリゾール株式会社製、商品名:ソルスパース43000〕0.2部、有機窒素硫黄化合物〔北興化学工業株式会社製、商品名:ホクサイドR-150、2-メチル-4-イソチアゾリン-3-オンと5-クロロ-2-メチル-4-イソチアゾリン-3-オンの混合物〕1.0部、ポリビニルアルコール0.5部、グリセリン25.0部、消泡剤0.02部、水47.78部を混合して感温変色性色彩記憶性液状組成物(筆記具用インキ)を得た。
ポリエステルスライバーを合成樹脂フィルムで被覆したインキ吸蔵体内にインキ組成物を含浸させ、ポリプロピレン樹脂からなる軸筒内に収容し、ホルダーを介して軸筒先端部にポリエステル繊維の樹脂加工ペン体(砲弾型)と接続状態に組み立て、キャップを装着して筆記具(マーキングペン)を得た。
軸筒後端部には摩擦部材としてSEBS樹脂を装着してなる。
実施例6で調製した感温変色性色彩記憶性マイクロカプセル顔料2.5部及び非熱変色性蛍光ピンク色顔料1.5部を、塩化ビニル-酢酸ビニル共重合樹脂12.5部、キシレン38.3部、酢酸ブチル45部、粘度調整剤0.2部からなる油性インキビヒクルに均一に分散させて感温変色性色彩記憶性液状組成物(塗料)を調製した。
実施例5で調製した感温変色性色彩記憶性マイクロカプセル顔料(予め-19℃以下に冷却して青色に発色させたもの)30部をアクリル系樹脂エマルジョン(固形分45%)60部、粘度調整剤1部、消泡剤0.2部、水8.8部からなる水性インキビヒクルに均一に分散させて感温変色性色彩記憶性液状組成物(印刷インキ)を調製した。
実施例6で調製した感温変色性色彩記憶性マイクロカプセル顔料5部、分散剤1部、非熱変色性ピンク色顔料0.1部、ポリプロピレンホモポリマー93.9部をエクストルーダーにて180℃で溶融混合して感温変色性色彩記憶性成形用樹脂組成物(ペレット)を得た。
実施例5で調製した感温変色性色彩記憶性マイクロカプセル顔料20部(予め-19℃以下に冷却して青色に発色させたもの)を、アクリル系樹脂エマルジョン(固形分40%)78.0部、消泡剤2.0部からなる水性インキビヒクルに均一に分散させて感温変色性色彩記憶性液状組成物(印刷インキ)を調製した。
T2 発色開始温度
T3 消色開始温度
T4 完全消色温度
ΔH ヒステリシス幅
Claims (10)
- (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、(c)前記(a)成分および(b)成分の呈色反応をコントロールする反応媒体として、下記式(1)で示されるエステル化合物と、を含んでなることを特徴とする感温変色性色彩記憶性組成物。
- 前記式(1)で表されるエステル化合物において、Rは炭素数6乃至16のアルキル基、炭素数6乃至8のシクロアルキルアルキル基、シクロヘキシル基、より好ましくは、炭素数6乃至14のアルキル基、シクロヘキシルメチル基のいずれかを示し、Xは水素原子、メチル基、エチル基、メトキシ基、またはエトキシ基のいずれかを示し、Yは水素原子、メチル基、エチル基、またはメトキシ基のいずれかである、請求項1に記載の組成物。
- 前記(a)成分が、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からなる群より選ばれる化合物である、請求項1にまたは2に記載の組成物。
- 前記成分(b)および前記成分(c)の構成比が、質量基準で、前記成分(a)1部に対して、それぞれ、0.1~50部、および1~800部である、請求項1~3のいずれか一項に記載の組成物。
- ヒステリシス幅ΔHが、8℃乃至80℃である、請求項1~4のいずれか一項に記載の組成物。
- 請求項1~5のいずれか1項に記載の感温変色性色彩記憶性組成物を内包してなることを特徴とする、感温変色性色彩記憶性マイクロカプセル顔料。
- 請求項6に記載のマイクロカプセル顔料と、ビヒクルと、を含んでなることを特徴とする、インキ組成物。
- 前記感温変色性色彩記憶性マイクロカプセル顔料の含有量が、前記インキ組成物の全質量に対し5~40質量%である、請求項7に記載のインキ組成物。
- 請求項7または8に記載のインキ組成物を収容した軸筒及び前記軸筒内の前記インキ組成物を導出するペン体を備えてなることを特徴とする、筆記具。
- 摩擦部材をさらに備えてなる、請求項9に記載の筆記具。
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CN201680045275.4A CN107922831B (zh) | 2015-08-03 | 2016-07-19 | 感温变色性色彩记忆性组合物及内包有该组合物的感温变色性色彩记忆性微胶囊颜料 |
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JP2019099628A (ja) * | 2017-11-30 | 2019-06-24 | パイロットインキ株式会社 | 可逆熱変色性組成物及びそれを内包した可逆熱変色性マイクロカプセル顔料 |
KR20210066226A (ko) * | 2019-11-28 | 2021-06-07 | 주식회사 인실리코 | 감온 변색성 조성물, 이를 포함하는 감온 변색성 마이크로캡슐 및 이를 이용한 시간-온도 지시계 |
US11814528B2 (en) | 2018-09-24 | 2023-11-14 | SOCIéTé BIC | Diester of bisphenol fluorene compounds and thermochromic pigment compositions comprising the same |
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GB2541910B (en) | 2015-09-03 | 2021-10-27 | Thermographic Measurements Ltd | Thermochromic composition |
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US10358570B2 (en) | 2019-07-23 |
CN107922831A (zh) | 2018-04-17 |
TWI714612B (zh) | 2021-01-01 |
JP6625643B2 (ja) | 2019-12-25 |
JPWO2017022471A1 (ja) | 2018-06-28 |
EP3333240B1 (en) | 2020-08-19 |
EP3333240A4 (en) | 2019-04-17 |
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