CN104395409A - Porphyrazine dye, and application therefor - Google Patents
Porphyrazine dye, and application therefor Download PDFInfo
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- CN104395409A CN104395409A CN201380031619.2A CN201380031619A CN104395409A CN 104395409 A CN104395409 A CN 104395409A CN 201380031619 A CN201380031619 A CN 201380031619A CN 104395409 A CN104395409 A CN 104395409A
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- pigment dispersion
- porphyrazine
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- BKYIMUSAVMSMGK-UHFFFAOYSA-N C1C=NN=CC1 Chemical compound C1C=NN=CC1 BKYIMUSAVMSMGK-UHFFFAOYSA-N 0.000 description 1
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
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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
- 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
- C09B67/006—Preparation of organic pigments
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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
- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/008—Preparations of disperse dyes or solvent dyes
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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
- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
A porphyrazine dye represented by formula (1), and a dye dispersing composition containing the same. In formula (1): M represents a metal atom, a metal oxide, a metal hydroxide, a metal halide, or a hydrogen atom; rings A, B, C and D each independently represent formulas (2)-(8) (except where A, B, and C are all (8)); X represents a lower alkyl group, a lower alkoxy group, an amino group, a nitro group, a halogen group, a hydroxy group, a carboxy group, a sulfonic acid group, or a sulfonamide group; Y represents a divalent crosslinking group; Z represents a sulfonic acid group, a carboxy group, a residue from which at least one hydrogen above a nitrogen atom on a primary-secondary amino group has been removed, or a residue from which at least one hydrogen above a nitrogen atom in a heterocyclic ring containing nitrogen has been removed; a and b are each average values; a and b are each 0-12; and the sum of a and b is 0-12.
Description
Technical field
The present invention relates to a kind of high, new-type porphyrazine pigment not damaging aesthetic property of transmitance and uses thereof demonstrating excellent absorption, visible region at specific near infrared region.
Background technology
In recent years, from the viewpoint of energy-conservation, global environmental problems etc., require the load alleviating conditioning unit.Such as in the field of house, automobile, there is the heat ray shielding glass be attached to from the heat ray shielding material of the invisible heat of sunlight by maskable on window glass, it rises to the temperature in indoor, car and has inhibition, as this heat ray shielding material, employ near infrared absorption pigment.
When being attached on the window glass of house or automobile by this heat ray shielding material, from the viewpoint of guaranteeing visibility, wish that visible light transmissivity is high; In addition from the viewpoint of energy-conservation, global environmental problems, wish that heat ray shielding ability is high, wish that there is the high-durability that can tolerate outdoor application.In addition, from the viewpoint of aesthetic property, water white transparency or painted shallow is as far as possible wished.
In patent documentation 1, as the heat ray shielding material that the transparency is excellent, disclose porphyrazine pigment.But the result studied from the present inventor, although the pigment visible light transmissivity recorded in patent documentation 1 is high, heat ray shielding is also excellent, yellow tone is strong, and grievous injury aesthetic property, is industrially difficult to use.
Prior art document
Patent documentation
Patent documentation 1: Japanese Unexamined Patent Publication 9-263717 publication
Summary of the invention
The problem that invention will solve
The present invention carries out in view of above-mentioned condition, the object of the present invention is to provide a kind of visible light transmissivity high and the porphyrazine pigment of heat ray shielding excellence.In addition, yellow tone does not damage aesthetic property in the field of house or automobile yet, industrial utility value is improved porphyrazine pigment and the heat ray shielding composition containing this pigment can be suppressed even if the object of the present invention is to provide.
For solving the scheme of problem
The present inventor conducts in-depth research for solving above-mentioned problem, found that, the porphyrazine pigment that specific following formula (1) represents or the pigment dispersion composition containing this porphyrazine pigment can solve above-mentioned problem, this completes the present invention.
That is, the present invention relates to following technical scheme:
(1) the porphyrazine pigment that represents of a kind of following formula (1).
[in formula (1), M represents atoms metal, metal oxide, metal hydroxides or metal halide or hydrogen atom, and ring A, B, C are following formula (2) ~ (8) independently of one another
But (A, B, C is above-mentioned formula (8) time different), * in above-mentioned formula (2) ~ (8) represents bonding position, X represents low alkyl group, lower alkoxy, amino, nitro, halogen, hydroxyl, carboxyl, sulfonic group, sulfoamido, Y represents divalence crosslinked group, Z represents sulfonic group, carboxyl, the residue that hydrogen removing at least 1 on the nitrogen-atoms of primary amino or secondary amino group is obtained, or the residue that the hydrogen comprised on the nitrogen-atoms of the heterocycle of nitrogen removing at least 1 is obtained, a and b is mean value, a, b is respectively less than more than 0 12, and a and b sum is less than more than 0 12].
(2) the porphyrazine pigment as described in (1), wherein, ring A, B, C in formula (1) are respectively formula (2), formula (4) or formula (8).
(3) the porphyrazine pigment as described in (1), wherein, ring A, B, C in formula (1) are respectively formula (4) or formula (8).
(4) the porphyrazine pigment as described in (3), wherein, the M in formula (1) is VO or Cu.
(5) the porphyrazine pigment as described in (4), wherein, in formula (1), Y to be carbonatoms be 1 ~ 3 alkylidene group, Z has or does not have substituent phthalimide-based or has or do not have substituent piperazinyl.
(6) the porphyrazine pigment that represents of a kind of following formula (9).
[ring A, B, C in formula (1) are respectively formula (4) or formula (8) (but being formula (8) when A, B, C are different)].
(7) a pigment dispersion composition, is characterized in that, its by the porphyrazine pigment dispersion according to any one of (1) ~ (6) in dispersion medium.
(8) the pigment dispersion composition as described in (7), is characterized in that, dispersion medium is acrylic acid series binding compositions.
(9) sheet, it is formed by the pigment dispersion composition be coated with described in (8).
(10) a pigment dispersion composition, is characterized in that, containing heat ray shielding metal particle in the pigment dispersion composition described in (8).
(11) a pigment dispersion composition, wherein, the heat ray shielding metal particle described in (10) is any one in stannic oxide, Indium sesquioxide or zinc oxide.
(12) sheet, it is formed by the pigment dispersion composition be coated with described in (11).
The effect of invention
By porphyrazine pigment of the present invention is used as heat ray shielding material, high visible light transmissivity and excellent heat ray shielding can be obtained, and can yellow tone be suppressed.Thus, do not damage aesthetic property, this porphyrazine pigment can be applied in the field of house or automobile.
Embodiment
Describe the present invention in detail.The present invention relates to the porphyrazine pigment of above-mentioned formula (1), its particularly in, make this pigment dispersion in various dispersion medium, make pigment dispersion composition.In addition, also can make in this pigment dispersion composition containing heat ray shielding metal particle.These compositions have the feature that can be applied in heat ray shielding adhesive sheet.
In above-mentioned formula (1), as the aromatic nucleus in the ring A ~ C represented by dotted line, such as with phenyl ring or naphthalene nucleus for representative, the nitrogenous fragrant heterocycle containing 1 or 2 nitrogen-atoms such as pyridine ring, pyrazine ring, pyridazine ring can be enumerated.Among these, the combination of preferred phenyl ring, pyridine ring, naphthalene nucleus, the more preferably combination of pyridine ring, naphthalene nucleus.In addition, pyridine ring most preferably is above-mentioned formula (4).
In above-mentioned formula (1), M represents hydrogen atom, atoms metal, metal oxide, metal hydroxides or metal halide.When M is beyond hydrogen atom, this M refers to that the porphyrin ring in formula (1) has so-called central metal.In addition, when M is hydrogen atom, refer to that this porphyrin ring does not have central metal.
As the concrete example of the atoms metal in above-mentioned M, such as Li, Na, K, Mg, Ti, Zr, V, Nb, Ta, Cr, Mo, W, Mn, Fe, Co, Ni, Ru, Rh, Pd, Os, Ir, Pt, Cu, Ag, Au, Zn, Cd, Hg, Al, Ga, In, Si, Ge, Sn, Pb, Sb, Bi etc. can be enumerated.
As metal oxide, VO, GeO etc. can be enumerated.As metal hydroxides, can enumerate such as Si (OH)
2, Cr (OH)
2, Sn (OH)
2, AlOH etc.As metal halide, such as SiCl can be enumerated
2, VCl, VCl
2, VOCl, FeCl, GaCl, ZrCl, AlCl etc.Among these, the atoms metals such as preferred Fe, Co, Cu, Ni, Zn, Al, V; The metal oxides such as VO; The metal hydroxidess etc. such as AlOH.More preferably Cu, VO can be enumerated, most preferably VO.
X in above-mentioned formula (1) represents low alkyl group, lower alkoxy, amino, nitro, halogen, hydroxyl, carboxyl, sulfonic group, sulfoamido." rudimentary " in the present invention represents that carbonatoms is 1 ~ 4.
Y is divalence crosslinked group, and can enumerate such as carbonatoms is the alkylidene group ,-CO of 1 ~ 3
2-,-SO
2-,-SO
2nH (CH
2) c-(herein, c represents 0 ~ 4), be preferably carbonatoms be 1 ~ 3 alkylidene group, c be 0-SO
2nH-, more preferably carbonatoms is the alkylidene group of 1 ~ 3.Z represents sulfonic group, carboxyl, the residue hydrogen removing at least 1 on the nitrogen-atoms of primary amino or secondary amino group obtained or the residue hydrogen comprised on the nitrogen-atoms of the heterocycle of nitrogen removing at least 1 obtained, carboxyl, sulfonic group such as can be shown, have or not there is substituent phthalimide-based, have or not there is substituent piperazinyl, have or not there is substituent piperidyl etc., preferred carboxyl, sulfonic group, have or not there is substituent phthalimide-based, preferably have or not there is substituent phthalimide-based.It should be noted that, as Z be have or not there is substituent phthalimide-based, have or not there is substituent piperazinyl, there is or not have substituent piperidyl time substituting group, hydrogen atom, low alkyl group, lower alkoxy, substituted-amino, nitro, halogen, sulfonic group can be shown, be preferably hydrogen atom, halogen.
In the present invention, substituted-amino is not particularly limited, comprises such as low alkyl group or lower alkoxy and replace and the amino that obtains." rudimentary " in the present invention represents that carbonatoms is 1 ~ 4, and halogen refers to Cl, Br, I.
A, b in above-mentioned formula (1) are respectively less than more than 0 12, and a and b sum is less than more than 0 12.It is less than more than 04 that preferred a, b are respectively less than more than 04, a and b sum.
Ring A ~ C in the porphyrazine pigment of the present invention above-mentioned formula (1) represented, the concrete example of X, Y and Z, the numerical value of a and b are shown in following table 1.
In order to illustrate pigment of the present invention, following example shows representational pigment, but the present invention is not limited to following example.In addition, when the nitrogenous fragrant heterocycle of ring A ~ C is above-mentioned formula (2), (3) and (5), there is the positional isomers of nitrogen-atoms, obtain with the form of the mixture of isomer when synthetic colour.The separation difficulty of these isomer, and be difficult to determine isomer by analyzing.Therefore, usually use with the state of mixture.Pigment of the present invention also comprises such mixture.In this specification sheets, not distinguishing these isomer etc., when representing with structural formula, recording 1 representational structural formula for convenience's sake.
[table 1]
The manufacture method of the porphyrazine pigment of the present invention that above-mentioned formula (1) represents is described.
The porphyrazine pigment that above-mentioned formula (1) represents such as can synthesize according to the known method disclosed in International Publication No. 2010/143619 brochure and International Publication No. 2010/013455 brochure.In addition, the porphyrazine pigment that formula (1) represents also can synthesize as follows: when utilizing known nitrile method or Wheeler method to synthesize, mixed ratio as the respective derivative in above-mentioned formula (2) ~ (7) of reaction raw materials use and naphthalene two acid derivative is changed, thus can synthesize.It should be noted that, as recorded in above-mentioned known document, the compound that the above-mentioned formula (1) obtained by aforesaid method is represented also becomes the mixture of the positional isomers relevant with the position of substitution of the nitrogen-atoms of the position of substitution of the nitrogenous fragrant heterocycle in ring A ~ C and nitrogenous fragrant heterocycle.
Compound N in table 1 o.3 or the compound that represents of No.18 such as can synthesize according to the known method disclosed in Japanese Patent No. 2507786 brochure, International Publication No. 2010/013455 brochure and Japanese Patent No. 3813750 brochure.
As the method be scattered in by the compound of above-mentioned formula (1) in dispersion medium, existing method can be used.Namely, the compound of above-mentioned formula (1) and dispersion medium can be mixed with specified proportion, add dispersion agent, tensio-active agent etc. as required, and utilize the diverting devices such as sand mill, masher, ball mill, homogenizer, coating drum, ball mill to disperse.Preferred ball mill among these.In addition, in the pulverizing of the pigment in ball mill, the pearl that preferably use diameter is little, the filling ratio etc. of increase pearl, thus process under the condition improving crush efficiency, and then preferably by filtration, centrifugation etc., pearl is removed after pulverization process.
The dispersion medium used in dispersion is not particularly limited, in the present invention, refers to water, organic solvent, binding compositions etc.In addition, these dispersion medium use as mixture after also can mixing.As organic solvent, such as hydrocarbon system solvent (toluene can be enumerated, dimethylbenzene, hexane, hexanaphthene, normal heptane etc.), alcohol series solvent (methyl alcohol, ethanol, Virahol, butanols, the trimethyl carbinol, phenylcarbinol etc.), ketone series solvent (acetone, methyl ethyl ketone, methyl iso-butyl ketone (MIBK), diisobutyl ketone, pimelinketone, methyl ethyl diketone etc.), ester series solvent (ethyl acetate, methyl acetate, butylacetate, cellosolve acetate, pentyl acetate etc.), ether series solvent (isopropyl ether, methylcyclohexane, ethylene glycol butyl ether, Isosorbide-5-Nitrae-dioxane etc.), glycol series solvent (ethylene glycol, Diethylene Glycol, triethylene glycol, propylene glycol etc.), glycol ethers series solvent (diethylene glycol monomethyl ether, propylene glycol monomethyl ether etc.), glycol ester series solvent (ethylene glycol monomethyl ether acetate, propylene glycol methyl ether acetate, diethylene glycol monoethyl ether acetic ester etc.), glyme series solvent (monoglyme, diglyme etc.), halogen series solvent (methylene dichloride, chloroform etc.), acid amides series solvent (DMF, N,N-dimethylacetamide, METHYLPYRROLIDONE), or pyridine, tetrahydrofuran (THF), tetramethylene sulfone, acetonitrile, dimethyl sulfoxide (DMSO).Be preferably water, ketone series solvent, alcohol series solvent, acid amides series solvent, hydrocarbon system solvent, be more preferably toluene, methyl ethyl ketone, methyl iso-butyl ketone (MIBK), methyl ethyl diketone.
In addition, when dispersion medium is acrylic acid series binding compositions, the acrylic acid copolymer system binder resin that preferred useful life longevity is high.Acrylic acid copolymer system binder resin can make usually in the copolymerization of the principal monomer low by second-order transition temperature when making polymkeric substance and the high comonomer of second-order transition temperature.
For the monomer of the raw material as acrylic acid copolymer system binder resin, can use that second-order transition temperature when making polymkeric substance is low, the carbonatoms of alkyl is the alkyl acrylate of 2 ~ 14 or the carbonatoms of alkyl be the alkyl methacrylate of 4 ~ 16 and make polymkeric substance time second-order transition temperature higher than above-mentioned monomer and can with their copolymerization monomer.
As the alkyl acrylate monomer that second-order transition temperature when making polymkeric substance is low, can exemplary propylene acetoacetic ester, n-propyl, vinylformic acid sec.-propyl, methoxyethyl acrylate, vinylformic acid normal-butyl, isobutyl acrylate, vinylformic acid sec-butyl, ethyl acrylate, n-octyl, Isooctyl acrylate monomer, vinylformic acid ester in the different ninth of the ten Heavenly Stems, the different stearyl ester of vinylformic acid etc.
In addition, as the low alkyl methacrylate monomer of second-order transition temperature when making polymkeric substance, methacrylic acid-2-ethylhexyl, n octyl methacrylate, the positive lauryl of methacrylic acid etc. can be illustrated.
In addition, as can the monomer of copolymerization, vinyl-acetic ester, vinyl cyanide, acrylamide, vinylbenzene, methyl methacrylate, methyl acrylate etc. can be illustrated.
Except above-mentioned monomer, in order to obtain required bond properties, as the monomer containing functional group, (methyl) vinylformic acid, methylene-succinic acid, (methyl) Hydroxyethyl acrylate, (methyl) Propylene glycol monoacrylate, (methyl) dimethylaminoethyl acrylate, acrylamide, n-methylolacrylamide, DMAA, glycidyl methacrylate, maleic anhydride etc. can also be used.
In addition, about molecular weight, the weight-average molecular weight of acrylic acid series binding compositions is preferably 100,000 ~ 1,200,000.Be more preferably 200,000 ~ 800,000.
The degree of crosslinking forming the macromolecular material of binding compositions is different according to the various condition such as kind, composition of macromolecular material, is not particularly limited, can adds softening agent if desired in macromolecular material.As this softening agent, the ester classes such as phthalic ester, trimellitate, pyromellitic ester, adipic acid ester, sebate, phosphotriester or glycol ester can be enumerated; Or process oil, liquid polyethers, liquid polyterpene, other liquid resin etc., can one kind or two or more used in combination by among these.Such softening agent is preferably the softening agent good with the consistency of binding compositions.In addition, except above-mentioned softening agent, various additive such as such as UV light absorber or antioxidant etc. can be added in binding compositions if desired.
About the compound of above-mentioned formula (1) when disperseing and the weight ratio of dispersion medium, the compound of above-mentioned formula (1) is set to 1, in contrast, preferably dispersion medium is 3 ~ 500, preferably dispersion medium is 15 ~ 100 further, and most preferably dispersion medium is 20 ~ 50.
As dispersion agent, low molecule negatively charged ion (anion) the property compound of representative is soap (soap), alpha-sulfo fatty acid ester salt (MES), alkylbenzene sulfonate (ABS), linear alkylbenzene sulfonate (LAS), alkyl-sulphate (AS), alkyl ether sulphate salts (AES), alkylsurfuric acid three ethanol ester and so on; The low molecule nonionic based compound of fatty acid ethanol amide, Voranol EP 2001 (AE), polyoxyethylene alkyl phenyl ether (Α Ρ Ε), Sorbitol Powder, sorbitol anhydride and so on; Low molecular weight cationic (cation) the property compound of alkyl trimethyl ammonium salt, dialkyl dimethyl ammonium chloride, alkylpyridinium chlorides and so on; The low molecule both sexes based compound of alkyl carboxyl trimethyl-glycine, sultaine, Yelkin TTS and so on; With the polymer water system dispersion agent that the copolymer salt, carboxymethyl cellulose, polyvinyl alcohol etc. of the formaldehyde condensation products of naphthalenesulfonate, poly styrene sulfonate, polyacrylate, vinyl compound and carboxylic serials monomer are representative; The non-water system dispersion agent of polymer of polyacrylic acid part alkyl ester, polyalkylene polyamine and so on; The macromolecule cation system dispersion agent of polymine, amino alkyl methacrylate multipolymer and so on, but as long as particle of the present invention can be applicable to well, just do not get rid of the dispersion agent of the structure beyond the material with illustrated form here.
As added dispersion agent, if enumerate concrete title, known following material.FlowlenDOPA-15B can be illustrated, Flowlen DOPA-17 (Kyoeisha Chemical Co., Ltd.'s manufacture), Solplus AX5, Solplus TX5, Solsperse 9000, Solsperse 12000, Solsperse 17000, Solsperse 20000, Solsperse 21000, Solsperse 24000, Solsperse 26000, Solsperse 27000, Solsperse 28000, Solsperse 32000, Solsperse 35100, Solsperse 54000, SOLTHIX 250, (Japanese Lu Borun Co., Ltd. manufactures), EFKA4008, EFKA4009, EFKA4010, EFKA4015, EFKA4046, EFKA4047, EFKA4060, EFKA4080, EFKA7462, EFKA4020, EFKA4050, EFKA4055, EFKA4400, EFKA4401, EFKA4402, EFKA4403, EFKA4300, EFKA4330, EFKA4340, EFKA6220, EFKA6225, EFKA6700, EFKA6780, EFKA6782, EFKA8503 (manufacture of EFKA Additives company), AJISPERPA111, AJISPER PB711, AJISPER PB821, AJISPER PB822, AJISPER PN411, FAMEXL-12 (manufacture of Ajinomoto Fine-Techno company), TEXAPHOR-UV21, TEXAPHOR-UV61 (manufacture of Cognis Japan company), DisperBYK101, DisperBYK102, DisperBYK106, DisperBYK108, DisperBYK111, DisperBYK116, DisperBYK130, DisperBYK140, DisperBYK142, DisperBYK145, DisperBYK161, DisperBYK162, DisperBYK163, DisperBYK164, DisperBYK166, DisperBYK167, DisperBYK168, DisperBYK170, DisperBYK171, DisperBYK174, DisperBYK180, DisperBYK182, DisperBYK192, DisperBYK193, DisperBYK2000, DisperBYK2001, DisperBYK2020, DisperBYK2025, DisperBYK2050, DisperBYK2070, DisperBYK2155, DisperBYK2164, BYK220S, BYK300, BYK306, BYK320, BYK322, BYK325, BYK330, BYK340, BYK350, BYK377, BYK378, BYK380N, BYK410, BYK425, BYK430 (manufacture of BYK-ChemieJapan company), DISPARLON 1751N, DISPARLON 1831, DISPARLON 1850, DISPARLON 1860, DISPARLON 1934, DISPARLON DA-400N, DISPARLONDA-703-50, DISPARLON DA-725, DISPARLON DA-705, DISPARLON DA-7301, DISPARLON DN-900, DISPARLON NS-5210, DISPARLON NVI-8514L, HIPLAADED-152, HIPLAAD ED-216, HIPLAAD ED-251, HIPLAAD ED-360 (nanmu originally changes into Co., Ltd.), FTX-207S, FTX-212P, FTX-220P, FTX-220S, FTX-228P, FTX-710LL, FTX-750LL, Ftergent 212P, Ftergent 220P, Ftergent 222F, Ftergent 228P, Ftergent 245F, Ftergent245P, Ftergent 250, Ftergent 251, Ftergent 710FM, Ftergent 730FM, Ftergent 730LL, Ftergent 730LS, Ftergent 750DM, Ftergent 750FM (manufacture of NEOS company), AS-1100, AS-1800, AS-2000 (Toagosei Co., Ltd's manufacture), KAOCER 2000, KAOCER 2100, KDH-154, MX-2045L, HOMOGENOL L-18, HOMOGENOL L-95, RHEODOL SP-010V, RHEODOL SP-030V, RHEODOL SP-L10, RHEODOL SP-P10 (Kao Corp's manufacture), EPAN U103, SHALLOL DC902B, NOIGEN EA-167, PLYSURF A219B, PLYSURFAL (Di-ichi Kogyo Seiyaku Co., Ltd.'s manufacture), MEGAFAC F-477, MEGAFAC 480SF, MEGAFACF-482 (Dainippon Ink Chemicals's manufacture), Silface SAG503A, Dynol 604 (Nishin Chemical Industry Co. Lt's manufacture), SN SPERSE 2180, SN SPERSE 2190, SN Leveller S-906 (manufacture of SAN NOPCO Co., Ltd.), S-386, the material of S-420 (manufacture of AGC SEIMI CHEMICAL Co., Ltd.) and so on.
When pigment dispersion composition of the present invention contains heat ray shielding metal particle, as used heat ray shielding metal particle, the absorption of visible ray material that is little, that near infrared portion to far infrared portion is had to good absorption characteristic is suitable.As this material, the conductive metal oxide near infrared region with plasma wavelength can be enumerated.Specifically, stannic oxide, Indium sesquioxide, zinc oxide, Tungsten oxide 99.999, chromic oxide, molybdenum oxide etc. can be illustrated.Wherein, preferably at stannic oxide, Indium sesquioxide, zinc oxide that the light absorption of visible region is little.
In addition, in order to improve the electroconductibility of these oxide compounds, particularly preferably adulterate the 3rd composition.As the hotchpotch for this object, Sb, V, Nb, Ta etc. are selected for stannic oxide, Zn, Al, Sn, Sb, Ga, Ge etc. are selected for Indium sesquioxide, Al, Ga, In, Sn, Sb, Nb etc. are selected for zinc oxide.
Be binding compositions and the method containing the pigment dispersion composition of heat ray shielding metal particle as obtaining dispersion medium, can using heat ray shielding metal particle, near infrared absorption pigment dispersion in the monomer of the main raw material as acrylic acid series binding compositions, then be polymerized, thus target heat ray shielding pigment dispersion composition can be obtained.In addition, also known method (Japanese Patent Application 2011-203869) can be utilized in advance to make the dispersion liquid of heat ray shielding metal particle, mix with monomer together with being dispersed with the composition of near infrared absorption pigment in organic solvent, make monomer polymerization afterwards, thus target pigment dispersive composition can be obtained.And then as easier method, can in the dispersion medium as acrylic acid series binding compositions the pigment of distributing (1), obtain composition, in obtained composition, directly mix the dispersion liquid of ready-made heat ray shielding metal particle, thus target pigment dispersive composition can be obtained.
The coating process of the pigment dispersion composition of organic solvent, binding compositions or these mixture or the pigment dispersion composition containing heat ray shielding metal particle in them is employed about dispersion medium, be not particularly limited, comma coating machine, bar coater, spin coater, spraying machine, roller coating machine, gravure coater, knife coater or other various apparatus for coating can be used.
Determine according to the coating thickness of bonding coat and shielding properties relative to the dispersion ratio of the heat ray shielding metal particle of acrylic acid series binding compositions and the compound of above-mentioned formula (1).As the optical property of film being coated with pigment dispersion composition, it is desirable to that visible light transmissivity is high, solar transmittance is low, but both has proportionlity usually, the performance by one party emphatically decides optical property.
Usually, consider and the tracing ability of joined face and bounding force and economy, the coating thickness of bonding coat adopts the thickness of 10 μm ~ 50 μm usually, as the amount of particulate of giving above-mentioned heat ray shielding in this range, be preferably (compound of heat ray shielding metal particle+above-mentioned formula (1)): the scope of resin solid content=3:97 ~ 1:1 (weight ratio).
Embodiment
Enumerate following embodiment and comparative example illustrates the present invention, but the invention is not restricted to these examples.As long as no special declaration, then the % in example and part are weight basis.
Embodiment 1 (above-claimed cpd example No.1)
In tetramethylene sulfone 120 parts, add Tetra hydro Phthalic anhydride 3.0 parts, naphthalene dicarboxylic anhydride 11.9 parts, urea 29 parts, ammonium molybdate 0.40 part and vanadyl chloride (V) 3.5 parts, obtained composition is warming up to 200 DEG C, react 11 hours at such a temperature.After reaction terminating, reaction solution is cooled to 65 DEG C, adds DMF (DMF) 100 parts, filtering separation separates out solid.Clean the solid obtained with DMF 50 parts, obtain wet cake 20.3 parts.Obtained wet cake is added in DMF 100 parts, obtained composition is warming up to 80 DEG C, and stir 2 hours at such a temperature.Filtering separation separates out solid, cleans, obtain wet cake 18.9 parts with 200 parts, water.Obtained wet cake is added in 150 parts, water, obtained composition is warming up to 90 DEG C, and stir 2 hours at such a temperature.Filtering separation separates out solid, cleans, obtain wet cake 16.1 parts with 200 parts, water.At the wet cake that 80 DEG C of dryings obtain, obtain 12.3 parts of above-claimed cpd example No.1.This compound maximum absorption wavelength is in concentrated sulfuric acid 943nm.
Embodiment 2 (above-claimed cpd example No.2)
Make the Tetra hydro Phthalic anhydride 3.0 parts in embodiment 1 become 5.9 parts, make naphthalene dicarboxylic anhydride 11.9 parts become 7.9 parts, obtain 12.1 parts of above-claimed cpd example No.2 in addition similarly to Example 1.This compound maximum absorption wavelength is in concentrated sulfuric acid 951nm, 882nm, 815nm.
Embodiment 3 (above-claimed cpd example No.9)
In tetramethylene sulfone 120 parts, add 3,4-pyridine dicarboxylic acid 3.3 parts, naphthalene dicarboxylic anhydride 7.9 parts, urea 29 parts, ammonium molybdate 0.40 part and vanadyl chloride (V) 3.5 parts, obtained composition is warming up to 200 DEG C, react 11 hours at such a temperature.After reaction terminating, reaction solution is cooled to 65 DEG C, adds DMF (DMF) 100 parts, filtering separation separates out solid.Clean the solid obtained with the DMF 200 parts of 80 DEG C, obtain wet cake 20.3 parts.Obtained wet cake is added in DMF 100 parts, obtained composition is warming up to 80 DEG C, and stir 2 hours at such a temperature.Filtering separation separates out solid, cleans, obtain wet cake 40.1 parts with 200 parts, water.Obtained wet cake is added in 150 parts, water, obtained composition is warming up to 90 DEG C, and stir 2 hours at such a temperature.Filtering separation separates out solid, cleans, obtain wet cake 35.2 parts with 7.9 parts, water.At the wet cake that 80 DEG C of dryings obtain, obtain 10.8 parts of above-claimed cpd example No.9.This compound maximum absorption wavelength is in concentrated sulfuric acid 933nm.
Embodiment 4 (above-claimed cpd example No.10)
Make 3, the 4-pyridine dicarboxylic acid 3.3 parts in embodiment 3 become 6.7 parts, make naphthalene dicarboxylic anhydride 11.9 parts become 7.9 parts, obtain 11.4 parts of above-claimed cpd example No.10 in addition similarly to Example 3.This compound maximum absorption wavelength is in concentrated sulfuric acid 939nm, 804nm, 711nm.
Embodiment 5 (above-claimed cpd example No.3)
In Tripyrophosphoric acid (116%) 40 part, add compound N o.13.4 part, phthalic imidine 4.9 parts, the paraformaldehyde 1.0 parts obtained in embodiment 1, obtained composition is warming up to 140 DEG C, and react 6 hours at such a temperature.After reaction terminating, reaction solution is cooled to 60 DEG C, adds 100 parts, water.Filtering separation is separated out solid and is washed, and obtains wet cake 34.0 parts.
Obtained wet cake is added in 10% potassium hydroxide aqueous solution 100 parts, make obtained composition 50 DEG C of reactions 2 hours.Filtering separation is separated out solid and is washed, and obtains wet cake 29 parts.
Obtained wet cake is added in DMF 100 parts, obtained composition is reacted at 25 DEG C.Filtering separation is separated out solid and is washed, and obtains wet cake 13.3 parts.At the wet cake that 80 DEG C of dryings obtain, obtain 6.5 parts of compound Ns o.3.This compound maximum absorption wavelength is in concentrated sulfuric acid 949nm.
Embodiment 6 (above-claimed cpd example No.11)
In embodiment 5, o.1 obtain 3.4 parts of compound Ns are replaced with 3.1 parts of compound Ns obtaining in embodiment 4 o.10, obtain 5.7 parts of compound Ns in addition similarly to Example 5 o.11 in embodiment 1.This compound maximum absorption wavelength is in concentrated sulfuric acid 940nm.
Embodiment 7 (pigment dispersion composition 1)
Compound 0.21g, the dispersion agent DisperBYK1400.21g of the above-mentioned formula (4) obtained is added in embodiment 1 in toluene 7ml, and then the zirconium oxide bead added as broken pearl, utilize batch-type pearl mill apparatus (T.K.FillMix 30-25 type, primix company manufacture) to carry out dispersion treatment.Use separating centrifuge (Hitachi Koki Co., Ltd himacCR18) to carry out centrifugal treating to obtained dispersion, thus obtain pigment dispersion composition 1.
Embodiment 8 ~ 10 (pigment dispersion composition 2,3,4)
Pigment in embodiment 7 is replaced with the compound obtained in embodiment 2,3 or 5, obtain pigment dispersion composition 2 ~ 4 similarly to Example 7 in addition.
Synthesis example 1 (acrylic acid series binding compositions)
N-butyl acrylate 291g and vinylformic acid 9g is dissolved in toluene 366g, adds Diisopropyl azodicarboxylate 0.15g, under nitrogen flowing in 70 DEG C of polymerizations 6 hours, obtain acrylic resin multipolymer (weight-average molecular weight: Mw=32 ten thousand).With this multipolymer of dilution with toluene, obtain the acrylic acid series binding compositions that solids component ratio is 29.36%, viscosity is 2700mPas.
Dispersion medium is the pigment dispersion composition of the mixture of organic solvent and acrylic acid series binding compositions and the making of said composition coated sheets
Embodiment 13
By the pigment dispersion composition 28.1 weight part mixed dissolution equably obtained in acrylic acid series binding compositions 100 weight part obtained in synthesis example 1 (butyl acrylate: vinylformic acid=97:3), embodiment 7, obtain pigment dispersion composition.In addition, comma coating machine is utilized to be applied to the polyester film (implementing organosilicon process in one side side) (3811 thickness that lintec company manufactures: 38 μm) of release sheet upper and by dried coating film, cover with the polyester film (implementing organosilicon process in one side side) (3801 thickness that lintec company manufactures: 38 μm) of release sheet, made pigment dispersion composition coated sheets (thickness: 15 μm) thus.
Embodiment 14 ~ 16
The pigment dispersion composition obtained in embodiment 7 is replaced with the pigment dispersion composition obtained in embodiment 8 ~ 10, obtain pigment dispersion composition coated sheets (thickness: 15 μm) 2 ~ 4 in addition similarly to Example 13.
Comparative example 1
Replace the pigment that obtains in embodiment 1 and use the compound that the formula (2) recorded in patent documentation 1 represents, make pigment dispersion composition similarly to Example 7 in addition, replace the pigment dispersion composition that obtains in embodiment 7 and use this pigment dispersion composition, having made pigment dispersion composition coated sheets (thickness: 15 μm) in addition similarly to Example 13.
Embodiment 17 (evaluation of pigment dispersion composition coated sheets)
The composition coated sheets made in embodiment 13 ~ 16, comparative example 1 is evaluated.The evaluation method of test method and result is as described below.
The calculating of the transmitance of (a) composition coated sheets
Utilize spectrophotometer (Shimadzu Seisakusho Ltd. manufactures UV-3150) to measure the transmitted spectrum of composition coated sheets obtained above, calculate transmitance.
B () adds up to the calculating at energy at sunshine (Tts)
Add up to energy at sunshine (Tts:Total Solar Transmittance, total solar energy transmission) be from the heat energy of the sun using the standard of which kind of degree through the material as object, utilize the calculating formula defined in ISO13837 to calculate.The numerical value calculated is less then represents that total energy at sunshine is less, represents that heat ray shielding is higher.
(C) calculating of the b* value of CIE1976 (L*a*b*) colorimeter system
The b* value of CIE1976 (L*a*b*) colorimeter system is the numerical value of the tone of the yellow representing measuring object, and the larger then yellow tone of numerical value is stronger, and the less then yellow tone of numerical value is more weak.This b* value calculates by the transmitted spectrum obtained in (a).
In this evaluation, compare b* value when making total energy at sunshine (Tts) value of expression heat ray shielding identical, and be summarized in table 2.
[table 2]
As shown in table 2, known: when using pigment of the present invention, compared with demonstrating the comparative example of identical heat ray shielding, b* value diminishes, and yellow tone significantly alleviates.For the composition coated sheets of embodiment 14, yellow tone cannot be confirmed by visual, but for the sheet of comparative example 1, confirming can with the strong yellow tone of the degree of visual confirmation.
Production Example 1 (heat ray shielding metal particle dispersion liquid)
Tin indium oxide 11.2 parts, methyl ethyl diketone 7.0 parts, dispersion agent DisperBYK1401.75 part is added in toluene 70 parts, and then the zirconium oxide bead added as broken pearl, utilize batch-type pearl mill apparatus (T.K.Fill Mix 30-25 type, primix company manufacture) to carry out dispersion treatment.In addition, separating centrifuge (Hitachi Koki Co., Ltd himacCR18) is used to carry out centrifugal treating to obtained dispersion (heat ray shielding metal particle dispersion liquid).
Employ the making of coated sheets as the pigment dispersion composition of dispersion medium or the pigment dispersion composition containing heat ray shielding metal particle in them of organic solvent, binding compositions or these mixture
Embodiment 18
By the colorant dispersing liquid 14.7 parts mixed dissolution equably obtained in the toluene dispersion liquid 144 parts of the stanniferous Indium sesquioxide (ITO) obtained in acrylic adhesive A 100 weight part obtained in synthesis example 1 (butyl acrylate: vinylformic acid=97:3), Production Example 1, embodiment 7, obtain heat ray shielding binding compositions.In addition, comma coating machine is utilized to be applied to the polyester film (implementing organosilicon process in one side side) (3811 thickness that lintec company manufactures: 38 μm) of release sheet upper and by dried coating film, cover with the polyester film (implementing organosilicon process in one side side) (3801 thickness that lintec company manufactures: 38 μm) of release sheet, made pigment dispersion composition coated sheets (thickness: 15 μm) thus.
Comparative example 2
Replace the colorant dispersing liquid that obtains in embodiment 7 and use the pigment dispersion composition made in comparative example 1, having made the pigment dispersion composition coated sheets (thickness: 15 μm) containing heat ray shielding metal particle in addition similarly to Example 18.
Embodiment 19
Similarly to Example 17 the sheet obtained in embodiment 18, comparative example 2 is evaluated.Its result is summarized in table 3.
[table 3]
As shown in table 3, known: even if when using the pigment dispersion composition to being obtained by mixture heat ray shield metal particle dispersion liquid in the composition of the porphyrazine pigment dispersion of (1) in dispersion medium, also same with the evaluation result shown in embodiment 19, compared with the pigment dispersion composition of the pigment using the formula (2) recorded in patent documentation 1 to represent, b* value diminishes, not by the impact with or without heat ray shielding metal particle, significantly alleviate yellow tone.
Industrial applicibility
The invention provides the near infrared absorption pigment as heat ray shielding material that a kind of heat ray shielding ability is excellent, yellow tone is few, aesthetic property is excellent.In addition, the near infrared absorption pigment obtained can be applied to the heat ray shielding material of the window glass towards house, automobile, extremely has value in practical.
Claims (12)
1. the porphyrazine pigment that represents of following formula (1),
In formula (1), M represents atoms metal, metal oxide, metal hydroxides or metal halide or hydrogen atom, and ring A, B and C are following formula (2) ~ (8) independently of one another,
But A, B, C is above-mentioned formula (8) time different, * in above-mentioned formula (2) ~ (8) represents bonding position, X represents low alkyl group, lower alkoxy, amino, nitro, halogen, hydroxyl, carboxyl, sulfonic group, sulfoamido, Y represents divalence crosslinked group, Z represents sulfonic group, carboxyl, the residue that hydrogen removing at least 1 on the nitrogen-atoms of primary amino or secondary amino group is obtained, or the residue that the hydrogen comprised on the nitrogen-atoms of the heterocycle of nitrogen removing at least 1 is obtained, a and b is mean value, a, b is respectively less than more than 0 12, and a and b sum is less than more than 0 12.
2. porphyrazine pigment as claimed in claim 1, wherein, ring A, B, C in formula (1) are respectively formula (2), formula (4) or formula (8).
3. porphyrazine pigment as claimed in claim 1, wherein, ring A, B, C in formula (1) are respectively formula (4) or formula (8).
4. porphyrazine pigment as claimed in claim 3, wherein, the M in formula (1) is VO or Cu.
5. porphyrazine pigment as claimed in claim 4, wherein, in formula (1), Y to be carbonatoms be 1 ~ 3 alkylidene group, Z has or does not have substituent phthalimide-based or has or do not have substituent piperazinyl.
6. the porphyrazine pigment that represents of following formula (9),
Ring A, B, C in formula (1) are respectively formula (4) or formula (8), but are formula (8) when A, B, C are different.
7. a pigment dispersion composition, is characterized in that, its by the porphyrazine pigment dispersion according to any one of claim 1 ~ 6 in dispersion medium.
8. pigment dispersion composition as claimed in claim 7, it is characterized in that, dispersion medium is acrylic acid series binding compositions.
9. a sheet, it is formed by coating pigment dispersion composition according to claim 8.
10. a pigment dispersion composition, is characterized in that, containing heat ray shielding metal particle in pigment dispersion composition according to claim 8.
11. 1 kinds of pigment dispersion compositions, wherein, heat ray shielding metal particle according to claim 10 is any one in stannic oxide, Indium sesquioxide or zinc oxide.
12. 1 kinds of sheets, it is formed by coating pigment dispersion composition according to claim 11.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610004096.8A CN105733293B (en) | 2012-06-18 | 2013-06-11 | Porphyrazine pigment and application thereof |
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| JP2012136550 | 2012-06-18 | ||
| JP2012-136550 | 2012-06-18 | ||
| PCT/JP2013/066031 WO2013191029A1 (en) | 2012-06-18 | 2013-06-11 | Porphyrazine dye, and application therefor |
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| CN201610004096.8A Division CN105733293B (en) | 2012-06-18 | 2013-06-11 | Porphyrazine pigment and application thereof |
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| CN104395409B CN104395409B (en) | 2016-08-24 |
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| CN201610004096.8A Expired - Fee Related CN105733293B (en) | 2012-06-18 | 2013-06-11 | Porphyrazine pigment and application thereof |
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| JP (1) | JP6181053B2 (en) |
| KR (1) | KR20150023250A (en) |
| CN (2) | CN104395409B (en) |
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| WO2022045236A1 (en) * | 2020-08-27 | 2022-03-03 | Dic株式会社 | Phthalocyanine production method |
| JP7205670B2 (en) * | 2020-08-27 | 2023-01-17 | Dic株式会社 | Phthalocyanine composition |
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| JP4659403B2 (en) * | 2004-07-15 | 2011-03-30 | 富士フイルム株式会社 | Phthalocyanine compound, ink, ink jet recording method, and image forming method |
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| JP2012025938A (en) * | 2010-06-21 | 2012-02-09 | Nippon Kayaku Co Ltd | Porphyrazine pigment, ink composition, recording method, and colored body |
| JP2013256548A (en) * | 2010-10-14 | 2013-12-26 | Nippon Kayaku Co Ltd | Porphyrazine dye, method for producing the same, ink composition, and colored body |
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- 2013-06-11 CN CN201380031619.2A patent/CN104395409B/en not_active Expired - Fee Related
- 2013-06-11 WO PCT/JP2013/066031 patent/WO2013191029A1/en active Application Filing
- 2013-06-11 CN CN201610004096.8A patent/CN105733293B/en not_active Expired - Fee Related
- 2013-06-11 KR KR20147031501A patent/KR20150023250A/en not_active Application Discontinuation
- 2013-06-11 JP JP2014521335A patent/JP6181053B2/en active Active
- 2013-06-17 TW TW102121427A patent/TWI601791B/en not_active IP Right Cessation
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Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2013191029A1 (en) | 2016-05-26 |
| WO2013191029A1 (en) | 2013-12-27 |
| KR20150023250A (en) | 2015-03-05 |
| TW201402709A (en) | 2014-01-16 |
| CN105733293B (en) | 2017-06-27 |
| TWI601791B (en) | 2017-10-11 |
| CN105733293A (en) | 2016-07-06 |
| CN104395409B (en) | 2016-08-24 |
| JP6181053B2 (en) | 2017-08-16 |
| HK1222407A1 (en) | 2017-06-30 |
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