CN105733293A - Porphyrazine dye, and application therefor - Google Patents
Porphyrazine dye, and application therefor Download PDFInfo
- Publication number
- CN105733293A CN105733293A CN201610004096.8A CN201610004096A CN105733293A CN 105733293 A CN105733293 A CN 105733293A CN 201610004096 A CN201610004096 A CN 201610004096A CN 105733293 A CN105733293 A CN 105733293A
- Authority
- CN
- China
- Prior art keywords
- group
- formula
- pigment dispersion
- pigment
- compositions
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 0 C1C=CC=*C1 Chemical compound C1C=CC=*C1 0.000 description 3
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
-
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Paints Or Removers (AREA)
- Dispersion Chemistry (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
The application is divisional application, and the application number of its original application is 201380031619.2, and the applying date is on June 11st, 2013, and denomination of invention is " porphyrazine pigment and application thereof ".
Technical field
The present invention relates to a kind of specific near infrared region demonstrate the absorption of excellence, visible region transmitance is high, the new-type porphyrazine pigment not damaging aesthetic property and application thereof.
Background technology
In recent years, from the viewpoint of energy-conservation, global environmental problems etc., it is desirable to alleviate the load of air-conditioning equipment.Such as house, automobile field in, there is the heat ray shielding glass being attached on glass pane from the heat ray shielding material of the heat ray of sunlight by maskable, temperature in indoor, car is risen and has inhibition by it, as this heat ray shielding material, employ near infrared absorption pigment.
When this heat ray shielding material is attached on the glass pane of house or automobile, from the viewpoint of guaranteeing observability, it is desirable to visible light transmissivity is high；Additionally from the viewpoint of energy-conservation, global environmental problems, it is desirable to heat ray shielding ability is high, it is desirable to have the high-durability that can tolerate outdoor application.Additionally, from the viewpoint of aesthetic property, it is desirable to water white transparency or painted shallow as far as possible.
In patent documentation 1, as the heat ray shielding material that the transparency is excellent, disclose porphyrazine pigment.But, although the result studied by the present inventor is it can be seen that the pigment visible light transmissivity recorded in patent documentation 1 is high, heat ray shielding is also excellent, but yellow tone is strong, seriously compromises aesthetic property, is industrially difficult with.
Prior art literature
Patent documentation
Patent documentation 1: Japanese Unexamined Patent Publication 9-263717 publication
Summary of the invention
The problem that invention to solve
The present invention carries out in view of above-mentioned condition, it is an object of the invention to provide the porphyrazine pigment that a kind of visible light transmissivity is high and heat ray shielding is excellent.Even if the porphyrazine pigment that yellow tone does not damage aesthetic property in the field of house or automobile yet, industrial value is improved and the heat ray shielding compositions containing this pigment can be suppressed it addition, it is an object of the invention to provide.
For solving the scheme of problem
The present inventor conducts in-depth research for solving above-mentioned problem, it was found that the porphyrazine pigment that specifically following formula (1) represents or the pigment dispersion compositions containing this porphyrazine pigment can solve above-mentioned problem, this completes the present invention.
That is, the present invention relates to techniques below scheme:
(1) the porphyrazine pigment that a kind of following formula (1) represents.
[in formula (1), M represents that metallic atom, metal-oxide, metal hydroxides or metal halide or hydrogen atom, ring A, B, C are each independently following formula (2)～(8)
But (A, B, it is above-mentioned formula (8) during C difference), * 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 bivalence crosslinked group, Z represents sulfonic group, carboxyl, residue hydrogen on the nitrogen-atoms of primary amino radical or secondary amino group being removed at least 1 and obtain, or the residue hydrogen on the nitrogen-atoms of the heterocycle comprising nitrogen being removed at least 1 and obtaining, a and b is meansigma methods, a, b 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 respectively formula (2) in formula (1), formula (4) or formula (8).
(3) the porphyrazine pigment as described in (1), wherein, ring A, B, C respectively formula (4) in formula (1) 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 is carbon number is the alkylidene of 1～3, and Z has or do not have the phthalimide-based of substituent group or has or do not have the piperazinyl of substituent group.
(6) the porphyrazine pigment that a kind of following formula (9) represents.
[ring A, B, C respectively formula (4) or formula (8) (but during A, B, C difference being formula (8))] in formula (1).
(7) a kind of pigment dispersion compositions, it is characterised in that its by the porphyrazine pigment dispersion according to any one of (1)～(6) in disperse medium.
(8) the pigment dispersion compositions as described in (7), it is characterised in that disperse medium is acrylic acid series binding compositions.
(9) a kind of sheet, it is formed by the pigment dispersion compositions described in coating (8).
(10) a kind of pigment dispersion compositions, it is characterised in that containing heat ray shielding metal particle in the pigment dispersion compositions described in (8).
(11) a kind of pigment dispersion compositions, wherein, the heat ray shielding metal particle described in (10) is any one in stannum oxide, Indium sesquioxide. or zinc oxide.
(12) a kind of sheet, it is formed by the pigment dispersion compositions described in coating (11).
The effect of invention
By the porphyrazine pigment of the present invention is used as heat ray shielding material, it is possible to obtain high visible light transmissivity and excellent heat ray shielding, and yellow tone can be suppressed.Thus, aesthetic property is not damaged, it is possible to be applied in the field of house or automobile by this porphyrazine pigment.
Detailed description of the invention
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 disperse medium, make pigment dispersion compositions.In addition it is also possible to make in this pigment dispersion compositions containing heat ray shielding metal particle.These compositionss have the feature can being applied in heat ray shielding bonding sheet.
In above-mentioned formula (1), as the aromatic rings in the ring A～C represented by dotted line, for instance with phenyl ring or naphthalene nucleus for representative, it is possible to enumerate the nitrogenous heteroaromatic containing 1 or 2 nitrogen-atoms such as pyridine ring, pyrazine ring, pyridazine ring.Among these, it is preferable that phenyl ring, pyridine ring, naphthalene nucleus combination, the more preferably combination of pyridine ring, naphthalene nucleus.It addition, pyridine ring most preferably is above-mentioned formula (4).
In above-mentioned formula (1), M represents hydrogen atom, metallic atom, metal-oxide, metal hydroxides or metal halide.When M is beyond hydrogen atom, the porphyrin ring that this M refers in formula (1) has so-called central metal.It addition, when M is hydrogen atom, refer to that this porphyrin ring does not have central metal.
Concrete example as the metallic atom in above-mentioned M, it is possible to enumerate 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..
As metal-oxide, it is possible to enumerate VO, GeO etc..As metal hydroxides, it is possible to enumerate such as Si (OH)2、Cr(OH)2、Sn(OH)2, AlOH etc..As metal halide, it is possible to enumerate such as SiCl2、VCl、VCl2, VOCl, FeCl, GaCl, ZrCl, AlCl etc..Among these, it is preferable that the metallic atoms such as 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, it is most preferred that 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 carbon number is 1～4.
Y is bivalence crosslinked group, it is possible to enumerate alkylidene ,-CO that such as carbon number is 1～32-、-SO2-、-SO2NH(CH2) c-(herein, c represents 0～4), it is preferred to-SO that alkylidene that carbon number is 1～3, c are 02NH-, more preferably carbon number is the alkylidene of 1～3.Z represents sulfonic group, carboxyl, the residue hydrogen removing at least 1 on the nitrogen-atoms of primary amino radical or secondary amino group obtained or the residue hydrogen on the nitrogen-atoms of the heterocycle comprising nitrogen being removed at least 1 and obtaining, carboxyl, sulfonic group such as can be shown, there is or do not have the phthalimide-based of substituent group, there is or do not have the piperazinyl of substituent group, there is or do not have the piperidyl etc. of substituent group, preferred carboxyl, sulfonic group, there is or not have the phthalimide-based of substituent group, it is preferable that there is or do not have the phthalimide-based of substituent group.It should be noted that, as Z be have or do not have substituent group phthalimide-based, there is or not have the piperazinyl of substituent group, there is or not have the piperidyl of substituent group time substituent group, hydrogen atom, low alkyl group, lower alkoxy, substituted-amino, nitro, halogen, sulfonic group can be shown, it is preferred to 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 carbon number is 1～4, and halogen refers to Cl, Br, I.
A, b in above-mentioned formula (1) respectively less than more than 0 12, and a and b sum is less than more than 0 12.Preferred a, b respectively less than more than 04, a and b sum is less than more than 04.
Ring A～the concrete example of C, X, Y and Z in the porphyrazine pigment of the present invention above-mentioned formula (1) represented, the numerical value of a and b are shown in table 1 below.
In order to illustrate the pigment of the present invention, following example illustrates representational pigment, but the present invention is not limited to following example.It addition, when the nitrogenous heteroaromatic of ring A～C is above-mentioned formula (2), (3) and (5), there is the position isomer of nitrogen-atoms, obtain with the form of the mixture of isomer when synthetic dyestuff.The separation difficulty of these isomers, and be difficult to by analysis, isomer is determined.Therefore, generally use with the state of mixture.The pigment of the present invention also comprises such mixture.In this specification, do not distinguish these isomers etc., when representing with structural formula, record 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 illustrated.
The porphyrazine pigment that above-mentioned formula (1) represents such as can synthesize by the known method according to No. 2010/143619 pamphlet of International Publication and No. 2010/013455 pamphlet of International Publication.Additionally, the porphyrazine pigment that formula (1) represents can also synthesize as follows: when utilizing known nitrile method or Wheeler method to synthesize, the mixed ratio making above-mentioned formula (2)～(7) the respective derivant as reaction raw materials use and naphthalene diacid derivative changes, such that it is able to synthesis.It should be noted that, recording in above-mentioned known document, the compound that the above-mentioned formula (1) obtained by said method is represented also becomes the mixture of the position isomer relevant with the position of substitution of the position of substitution of the nitrogenous heteroaromatic in ring A～C and the nitrogen-atoms of nitrogenous heteroaromatic.
Compound N in table 1 o.3 or the compound that represents of No.18 such as can the known method according to No. 2507786 pamphlets of Japanese Patent No., No. 2010/013455 pamphlet of International Publication and No. 3813750 pamphlets of Japanese Patent No. synthesize.
It is scattered in the method in disperse medium, it is possible to use existing method as by the compound of above-mentioned formula (1).Namely, the compound of above-mentioned formula (1) and disperse medium can be mixed with special ratios, it is added as needed on dispersant, surfactant etc., and utilizes the dispersal devices such as sand mill, grater, ball mill, homogenizer, edge runner, ball mill to disperse.Preferred ball mill among these.It addition, in the pulverizing of pigment in ball mill, it is preferred to use pearl that diameter is little, increase the filling rate etc. of pearl, thus processing when improving crush efficiency, so preferably in after pulverization process by filtrations, centrifugation etc. by pearl removing.
The disperse medium used in dispersion is not particularly limited, the present invention refers to water, organic solvent, binding compositions etc..It addition, these disperse medium use as mixture after can also mixing.nullAs organic solvent，Such as hydrocarbon system solvent (toluene can be enumerated、Dimethylbenzene、Hexane、Hexamethylene、Normal heptane etc.)、Alcohol series solvent (methanol、Ethanol、Isopropanol、Butanol、The tert-butyl alcohol、Benzyl alcohol etc.)、Ketone series solvent (acetone、Methyl ethyl ketone、Methyl iso-butyl ketone (MIBK)、Diisobutyl ketone、Ketohexamethylene、Acetylacetone,2,4-pentanedione etc.)、Ester series solvent (ethyl acetate、Methyl acetate、Butyl acetate、Cellosolve acetate、Pentyl acetate etc.)、Ether series solvent (diisopropyl ether、Methyl cellosolve、Butyl cellosolve、1,4-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 acetas etc.)、Glyme series solvent (monoglyme、Diethylene glycol dimethyl ether etc.)、Halogen series solvent (dichloromethane、Chloroform etc.)、Amide series solvent (N,Dinethylformamide、N,N-dimethyl acetylamide、METHYLPYRROLIDONE)、Or pyridine、Oxolane、Sulfolane、Acetonitrile、Dimethyl sulfoxide.It is preferably water, ketone series solvent, alcohol series solvent, amide series solvent, hydrocarbon system solvent, more preferably toluene, methyl ethyl ketone, methyl iso-butyl ketone (MIBK), acetylacetone,2,4-pentanedione.
It addition, when disperse medium is acrylic acid series binding compositions, it is preferred to use the acrylic acid copolymer system binder resin that durability is high.Acrylic acid copolymer system binder resin generally can be made by the copolymerization of the high comonomer of the low principal monomer of glass transition temperature when making polymer and glass transition temperature.
For the monomer of the raw material as acrylic acid copolymer system binder resin, can use that glass transition temperature when making polymer is low, the alkyl acrylate that carbon number is 2～14 of alkyl or the alkyl methacrylate that carbon number is 4～16 of alkyl and glass transition temperature when making polymer is higher than above-mentioned monomer and can with they copolymerization monomer.
As the alkyl acrylate monomer that glass transition temperature when making polymer is low, it is possible to exemplary propylene acetoacetic ester, n-propyl, acrylic acid isopropyl, methoxyethyl acrylate, acrylic acid normal-butyl, Isobutyl 2-propenoate, acrylic acid sec-butyl, acrylic acid-2-ethyl caproite, n-octyl, Isooctyl acrylate monomer, acrylic acid ester in the different ninth of the ten Heavenly Stems, the different stearyl ester of acrylic acid etc..
It addition, as the low alkyl methacrylate monomer of glass transition temperature when making polymer, it is possible to illustrate methacrylic acid-2-Octyl Nitrite, n octyl methacrylate, the positive lauryl of methacrylic acid etc..
It addition, as can the monomer of copolymerization, it is possible to illustrate vinyl acetate, acrylonitrile, acrylamide, styrene, methyl methacrylate, acrylic acid methyl ester. etc..
Except above-mentioned monomer, in order to obtain required bond properties, as the monomer containing functional group, it is also possible to use (methyl) acrylic acid, itaconic acid, (methyl) 2-(Acryloyloxy)ethanol, (methyl) Hydroxypropyl acrylate, (methyl) dimethylaminoethyl acrylate, acrylamide, n-methylolacrylamide, DMAA, glycidyl methacrylate, maleic anhydride etc..
It addition, about molecular weight, the weight average molecular weight of acrylic acid series binding compositions is preferably 100,000～1,200,000.It is more preferably 200,000～800,000.
The degree of cross linking of the macromolecular material constituting binding compositions is different according to the various condition such as the kind of macromolecular material, composition, it does not have be particularly limited to, it may be necessary to add plasticizer in macromolecular material.As this plasticizer, it is possible to enumerate the esters such as phthalic acid ester, trimellitate, pyromellitic ester, adipate ester, sebacate, phosphotriester or glycol ester；Or operation oil, liquid polyethers, liquid polyterpene, other liquid resin etc., it is possible to the one kind or two or more mixing among these is used.Such plasticizer is preferably the plasticizer good with the compatibility of binding compositions.It addition, except above-mentioned plasticizer, it may be necessary in binding compositions, add various additive such as such as UV absorbent or antioxidant etc..
Weight ratio about compound and the disperse medium of the above-mentioned formula (1) when disperseing, the compound of above-mentioned formula (1) is set to 1, in contrast, preferably disperse medium is 3～500, it is preferred that disperse medium is 15～100, it is most preferred that disperse medium is 20～50.
As dispersant, representative is low molecule anion (anion) the property compound of soap (soap), alpha-sulfo fatty acid ester salt (MES), alkylbenzenesulfonate (ABS), linear alkylbenzene sulfonate (LAS) (LAS), alkyl sulfate (AS), alkyl ether sulphate salts (AES), alkylsurfuric acid three ethanol ester etc；The low molecule nonionic based compound of fatty acid ethanol amide, polyoxyethylene alkyl ether (AE), polyoxyethylene alkyl phenyl ether (Α Ρ Ε), Sorbitol, sorbitol anhydride etc；Low molecular weight cationic (cation) the property compound of alkyl trimethyl ammonium salt, dialkyl dimethyl ammonium chloride, alkylpyridinium chlorides etc；The low molecule both sexes based compound of alkyl carboxyl glycine betaine, sulfobetaines, lecithin etc；The macromolecule water system dispersant being representative with the formaldehyde condensation products of naphthalene sulfonate, poly styrene sulfonate, polyacrylate, vinyl compound and the copolymer salt of carboxylic serials monomer, carboxymethyl cellulose, polyvinyl alcohol etc.；The non-water system dispersant of macromolecule of polyacrylic acid part Arrcostab, polyalkylene polyamine etc；The macromolecule cation system dispersant of polymine, amino alkyl methacrylate copolymer etc, but as long as the granule of the present invention can be highly suitable for, just it is not excluded for the dispersant with the structure beyond the material of form illustrated therein.
As the dispersant added, if enumerating concrete title, it is known that following material.nullFlowlenDOPA-15B can be illustrated、FlowlenDOPA-17 (Kyoeisha Chemical Co., Ltd.'s manufacture)、SolplusAX5、SolplusTX5、Solsperse9000、Solsperse12000、Solsperse17000、Solsperse20000、Solsperse21000、Solsperse24000、Solsperse26000、Solsperse27000、Solsperse28000、Solsperse32000、Solsperse35100、Solsperse54000、SOLTHIX250、(Lu Borun Co., Ltd. of Japan 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 EFKAAdditives company)、AJISPERPA111、AJISPERPB711、AJISPERPB821、AJISPERPB822、AJISPERPN411、FAMEXL-12 (manufacture of AjinomotoFine-Techno company)、TEXAPHOR-UV21、TEXAPHOR-UV61 (manufacture of CognisJapan 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)、DISPARLON1751N、DISPARLON1831、DISPARLON1850、DISPARLON1860、DISPARLON1934、DISPARLONDA-400N、DISPARLONDA-703-50、DISPARLONDA-725、DISPARLONDA-705、DISPARLONDA-7301、DISPARLONDN-900、DISPARLONNS-5210、DISPARLONNVI-8514L、HIPLAADED-152、HIPLAADED-216、HIPLAADED-251、HIPLAADED-360 (nanmu this chemical conversion Co., Ltd.)、FTX-207S、FTX-212P、FTX-220P、FTX-220S、FTX-228P、FTX-710LL、FTX-750LL、Ftergent212P、Ftergent220P、Ftergent222F、Ftergent228P、Ftergent245F、Ftergent245P、Ftergent250、Ftergent251、Ftergent710FM、Ftergent730FM、Ftergent730LL、Ftergent730LS、Ftergent750DM、Ftergent750FM (manufacture of NEOS company)、AS-1100、AS-1800、AS-2000 (Toagosei Co., Ltd's manufacture)、KAOCER2000、KAOCER2100、KDH-154、MX-2045L、HOMOGENOLL-18、HOMOGENOLL-95、RHEODOLSP-010V、RHEODOLSP-030V、RHEODOLSP-L10、RHEODOLSP-P10 (Kao Corp's manufacture)、EPANU103、SHALLOLDC902B、NOIGENEA-167、PLYSURFA219B、PLYSURFAL (Di-ichi Kogyo Seiyaku Co., Ltd.'s manufacture)、MEGAFACF-477、MEGAFAC480SF、MEGAFACF-482 (Dainippon Ink Chemicals's manufacture)、SilfaceSAG503A、Dynol604 (Nishin Chemical Industry Co. Lt's manufacture)、SNSPERSE2180、SNSPERSE2190、SNLevellerS-906 (manufacture of SANNOPCO Co., Ltd.)、S-386、The material of S-420 (manufacture of AGCSEIMICHEMICAL Co., Ltd.) etc.
When the pigment dispersion compositions of the present invention contains heat ray shielding metal particle, as the heat ray shielding metal particle used, it is seen that the material little, near-infrared portion to far infrared portion has good absorption characteristic that absorbs of light is suitable.As this material, it is possible to enumerate the conductive metal oxide near infrared region with plasma wavelength.Specifically, it is possible to illustrate stannum oxide, Indium sesquioxide., zinc oxide, tungsten oxide, chromium oxide, molybdenum oxide etc..Wherein, it is preferable that the little stannum oxide of light absorption in visible region, Indium sesquioxide., zinc oxide.
It addition, for the electric conductivity improving these oxides, it is particularly preferred to doping the 3rd composition.As alloy for the purpose, Sb, V, Nb, Ta etc. are selected for stannum 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.
It is binding compositions and the method for the pigment dispersion compositions containing heat ray shielding metal particle as obtaining disperse medium, can using heat ray shielding metal particle, near infrared absorption pigment dispersion in the monomer of the main material as acrylic acid series binding compositions, then target heat ray shielding pigment dispersion compositions it is polymerized, thus can be obtained.Additionally, known method (Japanese Patent Application 2011-203869) can also be advanced with and make the dispersion liquid of heat ray shielding metal particle, mix with monomer together with being dispersed with the compositions of near infrared absorption pigment in organic solvent, target pigment dispersive composition makes monomer polymerization afterwards, thus can be obtained.And then as easier method, can in the disperse medium as acrylic acid series binding compositions the pigment of distributing (1), obtain compositions, the dispersion liquid of ready-made heat ray shielding metal particle is directly mixed, thus target pigment dispersive composition can be obtained in obtained compositions.
Pigment dispersion compositions or the coating process of pigment dispersion compositions containing heat ray shielding metal particle in them of organic solvent, binding compositions or these mixture is employed about disperse medium, it is not particularly limited, it is possible to use comma coating machine, bar coater, spin coater, flush coater, roll coater, gravure coater, knife type coater or other various apparatus for coating.
Determine according to coating thickness and the shielding properties of adhesive layer with the dispersion ratio of the compound of above-mentioned formula (1) relative to the heat ray shielding metal particle of acrylic acid series binding compositions.Optical property as the film being coated with pigment dispersion compositions, it is generally desirable to visible light transmissivity is high, solar transmittance is low, but generally both has proportionate relationship, can determine optical property by the performance of one party emphatically.
Generally, consider the tracing ability with joined face and bonding force and economy, the coating thickness of adhesive layer generally adopts the thickness of 10 μm～50 μm, amount as the microgranule giving above-mentioned heat ray shielding in this range, it is preferred to (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 sulfolane 120 parts, add phthalic anhydride 3.0 parts, naphthalene dicarboxylic anhydride 11.9 parts, urea 29 parts, ammonium molybdate 0.40 part and divanadyl tetrachloride (V) 3.5 parts, obtained compositions is warming up to 200 DEG C, at such a temperature reaction 11 hours.After reaction terminating, reactant liquor being cooled to 65 DEG C, add DMF (DMF) 100 parts, isolated by filtration precipitates out solid.Clean obtained solid with DMF50 part, obtain wet cake 20.3 parts.Obtained wet cake is added in DMF100 part, obtained compositions is warming up to 80 DEG C, and stir 2 hours at such a temperature.Isolated by filtration precipitates out solid, is carried out with 200 parts of water, obtains wet cake 18.9 parts.Obtained wet cake is added in 150 parts of water, obtained compositions is warming up to 90 DEG C, and stir 2 hours at such a temperature.Isolated by filtration precipitates out solid, is carried out with 200 parts of water, obtains wet cake 16.1 parts.At 80 DEG C of dry obtained wet cakes, obtain 12.3 parts of above-claimed cpd example No.1.This compound maximum absorption wavelength in concentrated sulfuric acid is 943nm.
Embodiment 2 (above-claimed cpd example No.2)
Make the 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 in concentrated sulfuric acid is 951nm, 882nm, 815nm.
Embodiment 3 (above-claimed cpd example No.9)
In sulfolane 120 parts, add 3,4-dipicolinic acid 3.3 parts, naphthalene dicarboxylic anhydride 7.9 parts, urea 29 parts, ammonium molybdate 0.40 part and divanadyl tetrachloride (V) 3.5 parts, obtained compositions is warming up to 200 DEG C, at such a temperature reaction 11 hours.After reaction terminating, reactant liquor being cooled to 65 DEG C, add DMF (DMF) 100 parts, isolated by filtration precipitates out solid.Clean obtained solid with DMF200 parts of 80 DEG C, obtain wet cake 20.3 parts.Obtained wet cake is added in DMF100 part, obtained compositions is warming up to 80 DEG C, and stir 2 hours at such a temperature.Isolated by filtration precipitates out solid, is carried out with 200 parts of water, obtains wet cake 40.1 parts.Obtained wet cake is added in 150 parts of water, obtained compositions is warming up to 90 DEG C, and stir 2 hours at such a temperature.Isolated by filtration precipitates out solid, is carried out with 7.9 parts of water, obtains wet cake 35.2 parts.At 80 DEG C of dry obtained wet cakes, obtain 10.8 parts of above-claimed cpd example No.9.This compound maximum absorption wavelength in concentrated sulfuric acid is 933nm.
Embodiment 4 (above-claimed cpd example No.10)
Make 3, the 4-dipicolinic 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 in concentrated sulfuric acid is 939nm, 804nm, 711nm.
Embodiment 5 (above-claimed cpd example No.3)
Add in embodiment 1 in polyphosphoric acid (116%) 40 part obtain compound N o.13.4 part, phthalimide 4.9 parts, paraformaldehyde 1.0 parts, obtained compositions is warming up to 140 DEG C, and reaction 6 hours at such a temperature.After reaction terminating, reactant liquor is cooled to 60 DEG C, adds 100 parts of water.Isolated by filtration precipitates out solid and washes, and obtains wet cake 34.0 parts.
Obtained wet cake is added in 10% potassium hydroxide aqueous solution 100 parts, make obtained compositions react 2 hours at 50 DEG C.Isolated by filtration precipitates out solid and washes, and obtains wet cake 29 parts.
Obtained wet cake is added in DMF100 part, makes obtained compositions react at 25 DEG C.Isolated by filtration precipitates out solid and washes, and obtains wet cake 13.3 parts.At 80 DEG C of dry obtained wet cakes, obtain 6.5 parts of compound Ns o.3.This compound maximum absorption wavelength in concentrated sulfuric acid is 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 in concentrated sulfuric acid is 940nm.
Embodiment 7 (pigment dispersion compositions 1)
The compound 0.21g of above-mentioned formula (4), the dispersant DisperBYK1400.21g that obtain in embodiment 1 is added in toluene 7ml, and then add the zirconium oxide bead as broken pearl, utilize batch-type pearl mill apparatus (T.K.FillMix30-25 type, primix company manufacture) to carry out dispersion process.Centrifugal separator (Hitachi Koki Co., Ltd himacCR18) is used to be centrifuged obtained dispersion processing, thus obtaining pigment dispersion compositions 1.
Embodiment 8～10 (pigment dispersion compositions 2,3,4)
Pigment in embodiment 7 is replaced with the compound obtained in embodiment 2,3 or 5, obtains pigment dispersion compositions 2～4 in addition similarly to Example 7.
Synthesis example 1 (acrylic acid series binding compositions)
N-butyl acrylate 291g and acrylic acid 9g is dissolved in toluene 366g, adds azodiisobutyronitrile 0.15g, be polymerized 6 hours in 70 DEG C under nitrogen flowing, obtain acrylic resin copolymer (weight average molecular weight: Mw=32 ten thousand).With this copolymer of dilution with toluene, obtain solid constituent ratio be 29.36%, viscosity be the acrylic acid series binding compositions of 2700mPas.
Disperse medium is the making of the organic solvent pigment dispersion compositions with the mixture of acrylic acid series binding compositions and said composition coated sheets
Embodiment 13
The pigment dispersion compositions 28.1 weight portion mixed dissolution equably that will obtain in acrylic acid series binding compositions 100 weight portion (butyl acrylate: acrylic acid=97:3) obtained in synthesis example 1, embodiment 7, obtains pigment dispersion compositions.Additionally, comma coating machine is utilized to be applied on the polyester film (implementing organosilicon to process in one side side) (3811 thickness that lintec company manufactures: 38 μm) of release sheet and by dried coating film, cover with the polyester film (implementing organosilicon to process in one side side) (3801 thickness that lintec company manufactures: 38 μm) of release sheet, thus made pigment dispersion compositions coated sheets (thickness: 15 μm).
Embodiment 14～16
The pigment dispersion compositions obtained in embodiment 7 is replaced with the pigment dispersion compositions obtained in embodiment 8～10, obtains pigment dispersion compositions coated sheets (thickness: 15 μm) 2～4 in addition similarly to Example 13.
Comparative example 1
The pigment obtained in embodiment 1 is replaced to use the compound that in patent documentation 1, the formula (2) of record represents, make pigment dispersion compositions in addition similarly to Example 7, replace the pigment dispersion compositions obtained in embodiment 7 to use this pigment dispersion compositions, make pigment dispersion compositions coated sheets (thickness: 15 μm) in addition similarly to Example 13.
Embodiment 17 (evaluation of pigment dispersion compositions coated sheets)
The compositions coated sheets made in embodiment 13～16, comparative example 1 is evaluated.The evaluation methodology of test method and result is as described below.
The calculating of the transmitance of (a) compositions coated sheets
Utilize spectrophotometer (Shimadzu Seisakusho Ltd. manufactures UV-3150) to measure the transmitted spectrum of compositions coated sheets obtained above, calculate transmitance.
B () adds up to the calculating at energy at sunshine (Tts)
Add up to the heat energy originating from the sun energy at sunshine (Tts:TotalSolarTransmittance, total solar energy transmission) passes through the standard of the material as object using which kind of degree, utilize the calculating formula of definition in ISO13837 to calculate.The numerical value calculated is more little then represents that total energy at sunshine is more little, represents that heat ray shielding is more high.
(C) calculating of the b* value of CIE1976 (L*a*b*) colorimeter system
The b* value of CIE1976 (L*a*b*) colorimeter system indicates that the numerical value of the tone of the yellow of measuring object, and the more big then yellow tone of numerical value is more strong, and the more little then yellow tone of numerical value is more weak.The transmitted spectrum that this b* value can be passed through to obtain in (a) calculates.
In this evaluation, compare total energy at sunshine (Tts) value making expression heat ray shielding identical time b* value, and be summarized in table 2.
[table 2]
As shown in table 2, it is known that: when using the pigment of the present invention, compared with the comparative example demonstrating identical heat ray shielding, b* value diminishes, and yellow tone significantly alleviates.Compositions coated sheets for embodiment 14, it is impossible to by being visually confirmed to be yellow tone, but for the sheet of comparative example 1, confirming can the strong yellow tone of degree to be visually confirmed to be.
Manufacture example 1 (heat ray shielding metal particle dispersion liquid)
Tin indium oxide 11.2 parts, acetylacetone,2,4-pentanedione 7.0 parts, dispersant DisperBYK1401.75 part is added in toluene 70 parts, and then add the zirconium oxide bead as broken pearl, utilize batch-type pearl mill apparatus (T.K.FillMix30-25 type, primix company manufacture) to carry out dispersion process.It addition, use centrifugal separator (Hitachi Koki Co., Ltd himacCR18) that obtained dispersion (heat ray shielding metal particle dispersion liquid) has been carried out centrifugal treating.
Employ the making as the pigment dispersion compositions of disperse medium or the coated sheets of the pigment dispersion compositions containing heat ray shielding metal particle in them of organic solvent, binding compositions or these mixture
Embodiment 18
The colorant dispersing liquid 14.7 parts mixed dissolution equably that will obtain in the toluene dispersion liquid 144 parts of stanniferous Indium sesquioxide. (ITO) obtained in the acrylic adhesive A100 weight portion (butyl acrylate: acrylic acid=97:3) obtained in synthesis example 1, manufacture example 1, embodiment 7, obtains heat ray shielding binding compositions.Additionally, comma coating machine is utilized to be applied on the polyester film (implementing organosilicon to process in one side side) (3811 thickness that lintec company manufactures: 38 μm) of release sheet and by dried coating film, cover with the polyester film (implementing organosilicon to process in one side side) (3801 thickness that lintec company manufactures: 38 μm) of release sheet, thus made pigment dispersion compositions coated sheets (thickness: 15 μm).
Comparative example 2
Replace the colorant dispersing liquid obtained in embodiment 7 to use the pigment dispersion compositions of making in comparative example 1, make the pigment dispersion compositions 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 to the pigment dispersion compositions that heat of mixing alpha ray shield metal particle dispersion liquid in the porphyrazine pigment dispersion of (1) compositions in disperse medium is obtained, also same with the evaluation result shown in embodiment 19, compared with the pigment dispersion compositions 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 present 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.It addition, obtained near infrared absorption pigment can apply to the heat ray shielding material towards house, the glass pane of automobile, extremely there is value in practical.
Claims (10)
1. the porphyrazine pigment that following formula (1) represents,
In formula (1), M represents that metallic atom, metal-oxide, metal hydroxides or metal halide or hydrogen atom, ring A, B and C are following formula (4),
* in above-mentioned formula (4) represents bonding position, X represents lower alkoxy that low alkyl group that carbon number is 1～4, carbon number are 1～4, amino, nitro, halogen, hydroxyl, carboxyl, sulfonic group, sulfoamido, and Y represents the alkylidene ,-CO that select free carbon number to be 1～32-、-SO2-and-SO2NH(CH2) c-composition group in bivalence crosslinked group, wherein, c represents 0～4, Z represents sulfonic group, carboxyl or has or do not have the phthalimide-based of substituent group, has or do not have the piperazinyl of substituent group, has or do not have the piperidyl of substituent group, wherein, alkoxyl, substituted-amino, nitro, halogen or the sulfonic group that alkyl that described substituent group is hydrogen atom, carbon number is 1～4, carbon number are 1～4, a and b is meansigma methods, a, b 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, the M in formula (1) is VO or Cu.
3. porphyrazine pigment as claimed in claim 2, wherein, in formula (1), Y is carbon number is the alkylidene of 1～3, and Z has or do not have the phthalimide-based of substituent group or has or do not have the piperazinyl of substituent group.
4. porphyrazine pigment as claimed in claim 1, wherein, the M in formula (1) is VO.
5. a pigment dispersion compositions, it is characterised in that its by the porphyrazine pigment dispersion according to any one of Claims 1 to 4 in disperse medium.
6. pigment dispersion compositions as claimed in claim 5, it is characterised in that disperse medium is acrylic acid series binding compositions.
7. a sheet, it is formed by the pigment dispersion compositions described in coating claim 6.
8. pigment dispersion compositions as claimed in claim 6, it is characterised in that containing heat ray shielding metal particle.
9. pigment dispersion compositions as claimed in claim 8, wherein, described heat ray shielding metal particle is any one in stannum oxide, Indium sesquioxide. or zinc oxide.
10. a sheet, it is formed by the pigment dispersion compositions described in coating claim 9.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012136550 | 2012-06-18 | ||
| JPJP2012-136550 | 2012-06-18 | ||
| CN201380031619.2A CN104395409B (en) | 2012-06-18 | 2013-06-11 | Porphyrazine pigment and application thereof |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380031619.2A Division CN104395409B (en) | 2012-06-18 | 2013-06-11 | Porphyrazine pigment and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105733293A true CN105733293A (en) | 2016-07-06 |
| CN105733293B CN105733293B (en) | 2017-06-27 |
Family
ID=49768629
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610004096.8A Expired - Fee Related CN105733293B (en) | 2012-06-18 | 2013-06-11 | Porphyrazine pigment and application thereof |
| CN201380031619.2A Expired - Fee Related CN104395409B (en) | 2012-06-18 | 2013-06-11 | Porphyrazine pigment and application thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380031619.2A Expired - Fee Related CN104395409B (en) | 2012-06-18 | 2013-06-11 | Porphyrazine pigment and application thereof |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JP6181053B2 (en) |
| KR (1) | KR20150023250A (en) |
| CN (2) | CN105733293B (en) |
| HK (1) | HK1222407A1 (en) |
| TW (1) | TWI601791B (en) |
| WO (1) | WO2013191029A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2022045235A1 (en) * | 2020-08-27 | 2022-03-03 | Dic株式会社 | Phthalocyanine composition |
| JP7168126B2 (en) * | 2020-08-27 | 2022-11-09 | Dic株式会社 | Method for producing phthalocyanine |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4061654A (en) * | 1971-07-02 | 1977-12-06 | Polaroid Corporation | Novel tetrazaporphins |
| JPS63139789A (en) * | 1986-12-02 | 1988-06-11 | Mitsui Toatsu Chem Inc | Optical recording medium |
| CN1548422A (en) * | 2003-02-11 | 2004-11-24 | 杜锡光 | Super-phthalocyanine compound with six isoindole structure subunits in laver oxazine cycle and its synthesis and use |
| CN101548404A (en) * | 2006-05-25 | 2009-09-30 | 普林斯顿大学理事会 | Organic photosensitive devices using subphthalocyanine compounds |
| WO2012017873A1 (en) * | 2010-08-03 | 2012-02-09 | 富士フイルム株式会社 | Metal complex dye, photoelectric conversion element and photoelectrochemical cell |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH658771A5 (en) * | 1984-05-28 | 1986-12-15 | Ciba Geigy Ag | AZAPHTHALOCYANINE AND THEIR USE AS PHOTOACTIVATORS. |
| US6238931B1 (en) * | 1993-09-24 | 2001-05-29 | Biosite Diagnostics, Inc. | Fluorescence energy transfer in particles |
| JPH08281860A (en) * | 1995-04-11 | 1996-10-29 | Sumitomo Osaka Cement Co Ltd | Heat ray shielding film |
| JPH09263717A (en) * | 1996-01-25 | 1997-10-07 | Mitsui Toatsu Chem Inc | Water-base coating material containing near-infrared absorber dispersed therein and its use |
| JP3813750B2 (en) * | 1998-08-27 | 2006-08-23 | 大日精化工業株式会社 | Color filter manufacturing method and color filter |
| 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 |
| US7470315B2 (en) * | 2005-07-05 | 2008-12-30 | Silverbrook Research Pty Ltd | Red-shifted water dispersible napthalocyanine dyes |
| TW201011076A (en) * | 2008-08-01 | 2010-03-16 | Nippon Kayaku Kk | Hydrosoluble naphthalocyanine pigment and aqueous ink composition containing the same |
| 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 |
-
2013
- 2013-06-11 KR KR20147031501A patent/KR20150023250A/en not_active Application Discontinuation
- 2013-06-11 CN CN201610004096.8A patent/CN105733293B/en not_active Expired - Fee Related
- 2013-06-11 WO PCT/JP2013/066031 patent/WO2013191029A1/en active Application Filing
- 2013-06-11 CN CN201380031619.2A patent/CN104395409B/en not_active Expired - Fee Related
- 2013-06-11 JP JP2014521335A patent/JP6181053B2/en active Active
- 2013-06-17 TW TW102121427A patent/TWI601791B/en not_active IP Right Cessation
-
2016
- 2016-09-09 HK HK16110731.5A patent/HK1222407A1/en not_active IP Right Cessation
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4061654A (en) * | 1971-07-02 | 1977-12-06 | Polaroid Corporation | Novel tetrazaporphins |
| JPS63139789A (en) * | 1986-12-02 | 1988-06-11 | Mitsui Toatsu Chem Inc | Optical recording medium |
| CN1548422A (en) * | 2003-02-11 | 2004-11-24 | 杜锡光 | Super-phthalocyanine compound with six isoindole structure subunits in laver oxazine cycle and its synthesis and use |
| CN101548404A (en) * | 2006-05-25 | 2009-09-30 | 普林斯顿大学理事会 | Organic photosensitive devices using subphthalocyanine compounds |
| WO2012017873A1 (en) * | 2010-08-03 | 2012-02-09 | 富士フイルム株式会社 | Metal complex dye, photoelectric conversion element and photoelectrochemical cell |
Non-Patent Citations (2)
| Title |
|---|
| INDREK RENGE: "Influence of Temperature and Pressure on Shape and Shift of Impurity Optical Bands in Polymer Glasses", 《J. PHYS. CHEM. A》 * |
| 黄权真: "1,9,14,18,23,27,32,36-八丁氧基-2,3-萘酞菁Sn的合成及光谱特性的研究", 《中国优秀博硕士学位论文全文数据库（硕士）工程科技I辑》 * |
Also Published As
| Publication number | Publication date |
|---|---|
| TWI601791B (en) | 2017-10-11 |
| KR20150023250A (en) | 2015-03-05 |
| TW201402709A (en) | 2014-01-16 |
| WO2013191029A1 (en) | 2013-12-27 |
| CN105733293B (en) | 2017-06-27 |
| HK1222407A1 (en) | 2017-06-30 |
| CN104395409B (en) | 2016-08-24 |
| CN104395409A (en) | 2015-03-04 |
| JP6181053B2 (en) | 2017-08-16 |
| JPWO2013191029A1 (en) | 2016-05-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100731221B1 (en) | Methods For Conditioning Organic Pigments | |
| JP5800493B2 (en) | Rhodamine dye | |
| CN103781868B (en) | Heat ray shielding adhesion agent composition and the transparent adhesive sheet of heat ray shielding and its manufacture method | |
| CN102656245A (en) | Near-infrared absorptive coloring matter and near-infrared absorptive composition | |
| JP5610610B2 (en) | Azo dye | |
| CN105733293A (en) | Porphyrazine dye, and application therefor | |
| EP1956051B1 (en) | Phthalocyanine pigments with neutral metallic down flop | |
| JP2011190449A (en) | Method for conditioning organic pigments | |
| CA2776888C (en) | Easily dispersible pigment preparation based on c.i. pigment yellow 155 | |
| CN112639032A (en) | Pigment dispersant for paint | |
| TWI553071B (en) | Hotline Masking Adhesive Composition and Hot Wire Masking Adhesive Sheet | |
| CN103842463B (en) | Heat ray shielding adhesive composition and heat ray shielding bonding sheet | |
| JP2013227403A (en) | Heptamethine cyanine compound | |
| CN112638872A (en) | Pigment dispersants | |
| JP4628206B2 (en) | Method for producing organic pigment for color filter | |
| WO2024070862A1 (en) | Phthalocyanine pigment, phthalocyanine compound, coloring composition, method for producing phthalocyanine pigment, and method for producing coloring composition | |
| JP2012052030A (en) | Organic pigment composition | |
| JP2015168808A (en) | xanthene compound | |
| JPH11172134A (en) | Production of organic pigment having good property capable of readily dispersing, light resistance and heat resistance | |
| TW200902641A (en) | Pigment preparations based on diketopyrrolopyrroles | |
| JP2017160342A (en) | Azo compound | |
| JP2012092023A (en) | New naphtholactam compound | |
| JP2016050264A (en) | Xanthene compound |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| REG | Reference to a national code |
Ref country code: HK Ref legal event code: DE Ref document number: 1222407 Country of ref document: HK |
|
| REG | Reference to a national code |
Ref country code: HK Ref legal event code: GR Ref document number: 1222407 Country of ref document: HK |
|
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20170627 Termination date: 20190611 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |