CN105733293B - Porphyrazine pigment and application thereof - Google Patents
Porphyrazine pigment and application thereof Download PDFInfo
- Publication number
- CN105733293B CN105733293B CN201610004096.8A CN201610004096A CN105733293B CN 105733293 B CN105733293 B CN 105733293B CN 201610004096 A CN201610004096 A CN 201610004096A CN 105733293 B CN105733293 B CN 105733293B
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- Prior art keywords
- pigment
- formula
- pigment dispersion
- dispersion composition
- porphyrazine
- Prior art date
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- 239000000049 pigment Substances 0.000 title claims abstract description 97
- 239000000203 mixture Substances 0.000 claims abstract description 93
- 239000006185 dispersion Substances 0.000 claims abstract description 58
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000004429 atom Chemical group 0.000 claims abstract description 6
- 229910000000 metal hydroxide Inorganic materials 0.000 claims abstract description 6
- 150000004692 metal hydroxides Chemical class 0.000 claims abstract description 6
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 6
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 6
- 229910001507 metal halide Inorganic materials 0.000 claims abstract description 5
- 150000005309 metal halides Chemical class 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- -1 substituted-amino Chemical group 0.000 claims description 24
- 238000006467 substitution reaction Methods 0.000 claims description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 20
- 239000002923 metal particle Substances 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
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- 125000001118 alkylidene group Chemical group 0.000 claims description 6
- 229910003437 indium oxide Inorganic materials 0.000 claims description 6
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 claims description 6
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
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- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 8
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- 229910052757 nitrogen Inorganic materials 0.000 abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract description 3
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- 239000011248 coating agent Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
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- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 229910021549 Vanadium(II) chloride Inorganic materials 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229910007926 ZrCl Inorganic materials 0.000 description 1
- LWZFANDGMFTDAV-BURFUSLBSA-N [(2r)-2-[(2r,3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O LWZFANDGMFTDAV-BURFUSLBSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- GTYLEVMOSBBKCQ-UHFFFAOYSA-N acetic acid;2-(2-ethoxyethoxy)ethanol Chemical class CC(O)=O.CCOCCOCCO GTYLEVMOSBBKCQ-UHFFFAOYSA-N 0.000 description 1
- TUVYSBJZBYRDHP-UHFFFAOYSA-N acetic acid;methoxymethane Chemical compound COC.CC(O)=O TUVYSBJZBYRDHP-UHFFFAOYSA-N 0.000 description 1
- 239000003522 acrylic cement Substances 0.000 description 1
- 238000004378 air conditioning Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229920003144 amino alkyl methacrylate copolymer Polymers 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 229940084030 carboxymethylcellulose calcium Drugs 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- XOYLJNJLGBYDTH-UHFFFAOYSA-M chlorogallium Chemical compound [Ga]Cl XOYLJNJLGBYDTH-UHFFFAOYSA-M 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229940116364 hard fat Drugs 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- 150000003097 polyterpenes Chemical class 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910021509 tin(II) hydroxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- ITAKKORXEUJTBC-UHFFFAOYSA-L vanadium(ii) chloride Chemical compound Cl[V]Cl ITAKKORXEUJTBC-UHFFFAOYSA-L 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B47/00—Porphines; Azaporphines
Landscapes
- 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
The present invention relates to porphyrazine pigment and application thereof,It is following formula (1) [in formula (1),M represents metallic atom,Metal oxide,Metal hydroxides,Or metal halide,Or hydrogen atom,Ring A,B,C and D be each independently following formula (2)~(8) (but A,B,It is above-mentioned formula (8) when C is different),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,Hydrogen on the nitrogen-atoms of primary amino radical or secondary amino group is removed into residue obtained from least one,Or the hydrogen on the nitrogen-atoms of the heterocycle comprising nitrogen is removed into residue obtained from least one,A and b are average value,a,B is respectively less than more than 0 12,And a and b sums are less than more than 0 12] the porphyrazine pigment that represents and the pigment dispersion composition containing the porphyrazine pigment.
Description
The application is divisional application, and the Application No. 201380031619.2 of its original application, the applying date is June 11 in 2013
Day, entitled " porphyrazine pigment and application thereof ".
Technical field
The present invention relates to a kind of transmitance that excellent absorption, visible region are shown in specific near infrared region
New-type porphyrazine pigment high, not damage aesthetic property and application thereof.
Background technology
In recent years, from from the aspect of energy-conservation, global environmental problems etc., it is desirable to mitigate the load of air-conditioning equipment.For example living
In residence, the field of automobile, with the heat ray shielding material of the maskable heat ray from sunshine is attached on glass pane
Heat ray shielding glass, it rises to indoor, in-car temperature has inhibition, used as the heat ray shielding material
Material, has used near infrared absorption pigment.
When the heat ray shielding material is attached on the glass pane of house or automobile, examined in terms of observability is ensured
Consider, it is desirable to which visible light transmissivity is high；In addition from from the aspect of energy-conservation, global environmental problems, it is desirable to which heat ray shielding ability is high,
Wish that there is the high-durability of tolerable outdoor application.Additionally, from from the aspect of aesthetic property, it is desirable to as far as possible water white transparency,
Or colour shallow.
In patent document 1, as the heat ray shielding material that the transparency is excellent, porphyrazine pigment is disclosed.But,
The result studied from the present inventor, although pigment visible light transmissivity described in patent document 1 is high, heat ray shielding
Also it is excellent, but yellow tone is strong, seriously compromises aesthetic property, is industrially difficult with.
Prior art literature
Patent document
Patent document 1：Japanese Unexamined Patent Publication 9-263717 publications
The content of the invention
The invention problem to be solved
The present invention be in view of above-mentioned condition and carry out, it is an object of the invention to provide a kind of visible light transmissivity it is high,
And the excellent porphyrazine pigment of heat ray shielding.Even if in addition, it is an object of the invention to provide can suppress yellow tone,
Aesthetic property, the porphyrazine pigment that industrial value is improved are not damaged in the field of house or automobile and is contained yet
The heat ray shielding composition of the pigment.
Scheme for solving problem
The present inventor conducts in-depth research to solve above-mentioned problem, as a result finds, what specific following formula (1) represented
Porphyrazine pigment or the pigment dispersion composition containing the 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 a kind of following formula (1) represents.
[in formula (1), M represents that metallic atom, metal oxide, metal hydroxides or metal halide or hydrogen are former
Son, ring A, B, C are each independently following formula (2)~(8)
But (being above-mentioned formula (8) when A, B, C are different), the * in above-mentioned formula (2)~(8) represents bonding position, and X represents low
Level alkyl, lower alkoxy, amino, nitro, halogen, hydroxyl, carboxyl, sulfonic group, sulfoamido, Y represent divalence crosslinked group,
Z represents sulfonic group, carboxyl, the hydrogen on the nitrogen-atoms of primary amino radical or secondary amino group is removed residue obtained from least one or is incited somebody to action
Hydrogen on the nitrogen-atoms of the heterocycle comprising nitrogen removes residue obtained from least one, and a and b is average value, a, b be respectively 0 with
Upper less than 12, and a and b sums are 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 is the alkylidene that carbon number is 1~3, and Z is
With or without the phthalimide-based or the piperazinyl with or without substitution base of substitution base.
(6) the porphyrazine pigment that a kind of following formula (9) represents.
[ring A, B, C in formula (1) are respectively formula (4) or formula (8) (but being formula (8) when A, B, C difference)].
(7) a kind of pigment dispersion composition, it is characterised in that it is by the porphyrazine pigment any one of (1)~(6)
It is scattered in decentralized medium.
(8) the pigment dispersion composition as described in (7), it is characterised in that decentralized medium is acrylic acid series binding compositions.
(9) a kind of piece, it is formed by the pigment dispersion composition being coated with described in (8).
(10) a kind of pigment dispersion composition, it is characterised in that penetrated containing heat in the pigment dispersion composition described in (8)
Line shielding metal particle.
(11) a kind of pigment dispersion composition, wherein, the heat ray shielding metal particle described in (10) is tin oxide, oxygen
Change any one in indium or zinc oxide.
(12) a kind of piece, it is formed by the pigment dispersion composition being coated with described in (11).
The effect of invention
By by porphyrazine pigment of the invention be used as heat ray shielding material, can obtain high visible light transmissivity and
Excellent heat ray shielding, and yellow tone can be suppressed.Thus, aesthetic property is not damaged, can be by the porphyrazine pigment
It is applied in the field of house or automobile.
Specific embodiment
Describe the present invention in detail.The present invention relates to the porphyrazine pigment of above-mentioned formula (1), it is particularly in making the pigment point
Dissipate in various decentralized media, be made pigment dispersion composition.In addition it is also possible to make to be penetrated containing heat in the pigment dispersion composition
Line shielding metal particle.These compositions have the feature that can be 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, such as with phenyl ring or naphthalene nucleus as representative,
Pyridine ring, pyrazine ring, pyridazine ring etc. can be enumerated and contain the 1 or 2 nitrogenous heteroaromatic of nitrogen-atoms.Among these, preferred benzene
Ring, pyridine ring, the combination of naphthalene nucleus, the more preferably combination of pyridine ring, naphthalene nucleus.In addition, pyridine ring is most preferably above-mentioned formula (4).
In above-mentioned formula (1), M represents hydrogen atom, metallic atom, metal oxide, metal hydroxides or metal halide
Thing.M be hydrogen atom beyond in the case of, the M refers to that the porphyrin ring in formula (1) has so-called central metal.In addition, being in M
Refer to that the porphyrin ring does not have central metal in the case of hydrogen atom.
As the concrete example of the metallic atom in above-mentioned M, can 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, VO, GeO etc. can be enumerated.As metal hydroxides, such as Si (OH) can be enumerated2、
Cr(OH)2、Sn(OH)2, AlOH etc..As metal halide, such as SiCl can be enumerated2、VCl、VCl2、VOCl、FeCl、
GaCl, ZrCl, AlCl etc..Among these, the preferred metallic atom such as Fe, Co, Cu, Ni, Zn, Al, V；The metal oxides such as VO；
Metal hydroxides such as AlOH etc..Cu, VO, most preferably VO can more preferably be enumerated.
X in above-mentioned formula (1) represents low alkyl group, lower alkoxy, amino, nitro, halogen, hydroxyl, carboxyl, sulfonic acid
Base, sulfoamido." rudimentary " expression carbon number in the present invention is 1~4.
Y is divalence crosslinked group, can enumerate alkylidene ,-CO that such as carbon number is 1~32-、-SO2-、-SO2NH
(CH2) c- (and herein, c represent 0~4), preferably carbon number is 1~3 the alkylidene ,-SO that c is 02NH-, more preferably carbon are former
Subnumber is 1~3 alkylidene.Z represents sulfonic group, carboxyl, the hydrogen on the nitrogen-atoms of primary amino radical or secondary amino group is removed at least one
Obtained from residue or the hydrogen on the nitrogen-atoms of the heterocycle comprising nitrogen is removed into residue obtained from least one, can for example show
Go out carboxyl, sulfonic group, the phthalimide-based with or without substitution base, the piperazine with or without substitution base
Base, the piperidyl etc. with or without substitution base, preferably carboxyl, sulfonic group, the O-phthalic with or without substitution base
Imide, preferably with or without the phthalimide-based of substitution base.It should be noted that as Z be with or
Without substitution base phthalimide-based, with or without substitution base piperazinyl, with or without substitution base
Piperidyl when substitution base, hydrogen atom, low alkyl group, lower alkoxy, substituted-amino, nitro, halogen, sulfonic acid can be shown
Base, preferably hydrogen atom, halogen.
In the present invention, substituted-amino is not particularly limited, is obtained comprising such as low alkyl group or lower alkoxy substitution
The amino for arriving." rudimentary " expression carbon number in the present invention 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 sums are less than more than 0 12.It is preferred that a, b distinguish
It is less than more than 04, a is less than more than 04 with b sums.
The concrete example of the ring A~C, X, Y and Z in the porphyrazine pigment of the invention that above-mentioned formula (1) is represented, a and b
Numerical value is shown in table 1 below.
In order to illustrate pigment of the invention, following examples show representational pigment, but the present invention is not limited to
Following examples.In addition, in the case where the nitrogenous heteroaromatic of ring A~C is for above-mentioned formula (2), (3) and (5), there is the position of nitrogen-atoms
Isomers is put, is obtained in the form of the mixture of isomers in synthetic dyestuff.The separation of these isomers is difficult, Er Qienan
Isomers is determined with by analyzing.Therefore, generally used with the state of mixture.Pigment of the invention is also comprising so
Mixture.In this specification, these isomers etc. are not distinguished, in the case where being represented with structural formula, remember for convenience's sake
Carry 1 representational structural formula.
【Table 1】
The manufacture method of the porphyrazine pigment of the invention represented above-mentioned formula (1) is illustrated.
The porphyrazine pigment that above-mentioned formula (1) represents for example can according to No. 2010/143619 pamphlet of International Publication No. and
Known method disclosed in No. 2010/013455 pamphlet of International Publication No. is synthesized.In addition, the porphyrazine that formula (1) is represented
Pigment can also synthesize as follows：When being synthesized using known nitrile method or Wheeler method, make what is used as reaction raw materials
Above-mentioned formula (2)~(7) respective derivative changes with the mixed ratio of naphthalene diacid derivative, such that it is able to synthesize.Need
Illustrate, as described above described in known document as, the compound that the above-mentioned formula (1) obtained by the above method is represented is also
As the position relevant with the position of substitution of the nitrogen-atoms of the position of substitution and nitrogenous heteroaromatic of the nitrogenous heteroaromatic in ring A~C
Put the mixture of isomers.
Compound N in table 1 is o.3 or the compounds that represent of No.18 for example can be small according to Japanese Patent No. 2507786
Known method disclosed in book, No. 3813750 pamphlets of No. 2010/013455 pamphlet of International Publication and Japanese Patent No.
Synthesized.
Method as being scattered in the compound of above-mentioned formula (1) in decentralized medium, it is possible to use existing method.That is,
The compound of above-mentioned formula (1) and decentralized medium can be mixed with special ratios, be added as needed on dispersant, surfactant
Deng, and disperseed using dispersal devices such as sand mill, grater, ball mill, homogenizer, edge runner, ball mills.Among these
It is preferred that ball mill.In addition, in the crushing of pigment in ball mill, the small pearl of diameter, filling rate of increase pearl etc. are preferably used,
So as to be processed under conditions of crush efficiency is improved, and then will by filtering, centrifugation etc. preferably after pulverization process
Pearl removes.
Decentralized medium to being used in dispersion is not particularly limited, and refers to water, organic solvent, binding compositions in the present invention
Deng.In addition, these decentralized media are used after can also mixing as mixture.As organic solvent, such as hydrocarbon system can be enumerated
Solvent (toluene, dimethylbenzene, hexane, hexamethylene, normal heptane etc.), alcohol series solvent (methyl alcohol, ethanol, isopropanol, butanol, the tert-butyl alcohol,
Phenmethylol etc.), ketone series solvent (acetone, methyl ethyl ketone, methyl iso-butyl ketone (MIBK), DIBK, cyclohexanone, acetylacetone,2,4-pentanedione
Deng), ester series solvent (ethyl acetate, methyl acetate, butyl acetate, cellosolve acetate, pentyl acetate etc.), ether series solvent (isopropyl
Ether, methyl cellosolve, butyl cellosolve, 1,4- dioxane etc.), two alcohol series solvents (ethylene glycol, diethylene glycol, triethylene glycol,
Propane diols etc.), glycol ether series solvent (diethylene glycol monomethyl ether, propylene glycol monomethyl ether etc.), glycol ester series solvent (ethylene glycol list
Methyl ether acetate, propylene glycol methyl ether acetate, diethylene glycol monoethyl ether acetic acid esters etc.), glyme series solvent (Monoethylene Glycol (MEG)
Dimethyl ether, diethylene glycol dimethyl ether etc.), halogen-based solvent (dichloromethane, chloroform etc.), acid amides series solvent (N, N- dimethyl formyl
Amine, DMAC N,N' dimethyl acetamide, METHYLPYRROLIDONE) or pyridine, tetrahydrofuran, sulfolane, acetonitrile, dimethyl Asia
Sulfone.Preferably water, ketone series solvent, alcohol series solvent, acid amides series solvent, hydrocarbon system solvent, more preferably toluene, methyl ethyl ketone, first
Base isobutyl ketone, acetylacetone,2,4-pentanedione.
In addition, in the case where decentralized medium is acrylic acid series binding compositions, preferably using durability acrylic acid high
Copolymer system binder resin.Acrylic copolymer system binder resin generally can be by the glass transition temperature that is made during polymer
The copolymerization of low principal monomer and glass transition temperature comonomer high is spent to make.
For the monomer of the raw material as acrylic copolymer system binder resin, vitrifying when being made polymer can be used
The alkyl acrylate that transition temperature is low, alkyl carbon number is 2~14 or the methyl-prop that the carbon number of alkyl is 4~16
Olefin(e) acid Arrcostab and glass transition temperature when being made polymer are higher than above-mentioned monomer and can be with the list of their copolymerization
Body.
As the low alkyl acrylate monomer of glass transition temperature when being made polymer, can be with exemplary propylene acid second
Ester, n-propyl, acrylic acid isopropyl, methoxyethyl acrylate, acrylic acid normal-butyl, isobutyl acrylate, propylene
The different nonyl ester of sour sec-butyl, acrylic acid-2-ethyl caproite, n-octyl, Isooctyl acrylate monomer, acrylic acid, acrylic acid are different hard
Fat ester etc..
In addition, as the low alkyl methacrylate monomer of glass transition temperature when being made polymer, can be with
Illustrate methacrylic acid -2- Octyl Nitrites, n octyl methacrylate, the positive lauryl of methacrylic acid etc..
In addition, as the monomer for being capable of copolymerization, vinyl acetate, acrylonitrile, acrylamide, styrene, first can be illustrated
Base methyl acrylate, methyl acrylate etc..
In addition to above-mentioned monomer, in order to obtain required bond properties, as the monomer containing functional group, can also make
With (methyl) acrylic acid, itaconic acid, (methyl) hydroxy-ethyl acrylate, (methyl) hydroxypropyl acrylate, (methyl) acrylic acid diformazan
Amino ethyl ester, acrylamide, NMA, DMAA, GMA, maleic anhydride
Deng.
In addition, on molecular weight, the weight average molecular weight of acrylic acid series binding compositions is preferably 100,000~1,200,000.It is more excellent
Elect 200,000~800,000 as.
The degree of cross linking of macromolecular material of binding compositions is constituted according to various conditions such as species, the compositions of macromolecular material
And it is different, it is not particularly limited, it may be necessary to plasticizer is added in macromolecular material.As the plasticizer, neighbour can be enumerated
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 resins etc., can by these among one kind or two or more mixing
Use.Such plasticizer is preferably the plasticizer good with the compatibility of binding compositions.In addition, except above-mentioned plasticizer with
Outward, it may be necessary to adding the various additives such as such as ultra-violet absorber or antioxidant in binding compositions.
The compound of the above-mentioned formula (1) during on being disperseed and the weight ratio of decentralized medium, by the chemical combination of above-mentioned formula (1)
Thing is set to 1, in contrast, it is preferred that decentralized medium be 3~500, further preferred decentralized medium be 15~100, most preferably disperse
Medium is 20~50.
Used as dispersant, representative is soap (soap), alpha-sulfo fatty acid ester salt (MES), alkylbenzene
Sulfonate (ABS), linear alkylbenzene sulfonate (LAS) (LAS), alkyl sulfate (AS), alkyl ether sulphate salts (AES), alkylsurfuric acid
Low molecule anion (anion) property compound of three ethanol esters etc；Fatty acid ethanol amide, polyoxyethylene alkyl ether (AE),
The low molecule nonionic based compound of polyoxyethylene alkyl phenyl ether (Α Ρ Ε), D-sorbite, sorbitol anhydride etc；Alkyl three
Low molecular weight cationic (cation) property compound of methyl ammonium salt, dialkyl dimethyl ammonium chloride, alkylpyridinium chlorides etc；Alkane
The low molecule both sexes based compound of base carboxybetaine, sulfobetaines, lecithin etc；With the formaldehyde condensation of naphthalene sulfonate
The copolymer salt of thing, poly styrene sulfonate, polyacrylate, vinyl compound and carboxylic serials monomer, carboxymethylcellulose calcium,
Polyvinyl alcohol etc. is the macromolecule water system dispersant of representative；The high score of polyacrylic acid part Arrcostab, polyalkylene polyamine etc
The non-water system dispersant of son；The macromolecule cation system dispersion of polyethyleneimine, amino alkyl methacrylate copolymer etc
Agent, but as long as particle of the invention can be highly suitable for, be just not excluded for the material with form illustrated therein with
The dispersant of outer structure.
As the dispersant for being added, if enumerating specific name, it is known that following material.Flowlen DOPA- can be illustrated
15B, 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
32000th, Solsperse 35100, Solsperse 54000, SOLTHIX 250, (Japanese Lu Borun Co., Ltd. manufacture),
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 companies), AJISPERPA111, AJISPER PB711, AJISPER PB821,
AJISPER PB822, AJISPER PN411, FAMEX L-12 (manufacture of Ajinomoto Fine-Techno companies),
TEXAPHOR-UV21, TEXAPHOR-UV61 (manufacture of Cognis Japan companies), 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-Chemie Japan companies), DISPARLON
1751N、DISPARLON 1831、DISPARLON 1850、DISPARLON 1860、DISPARLON 1934、DISPARLON
DA-400N、DISPARLON DA-703-50、DISPARLON DA-725、DISPARLON DA-705、DISPARLON DA-
7301、DISPARLON DN-900、DISPARLON NS-5210、DISPARLON NVI-8514L、HIPLAAD ED-152、
HIPLAAD ED-216, HIPLAAD ED-251, HIPLAAD ED-360 (this chemical conversion of nanmu 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、Ftergent 245P、Ftergent 250、
Ftergent 251、Ftergent 710FM、Ftergent 730FM、Ftergent 730LL、Ftergent 730LS、
(East Asia synthesizes for Ftergent 750DM, Ftergent 750FM (manufacture of NEOS companies), AS-1100, AS-1800, AS-2000
Co., Ltd. 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,
PLYSURF AL (Di-ichi Kogyo Seiyaku Co., Ltd.'s manufacture), MEGAFAC F-477, MEGAFAC 480SF, MEGAFAC F-
482 (Dainippon Ink Chemicals's manufactures), 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, S-
The material of 420 (manufactures of AGC SEIMI CHEMICAL Co., Ltd.) etc.
In the case where pigment dispersion composition of the invention contains heat ray shielding metal particle, as what is used
Heat ray shielding metal particle, it is seen that absorbing for light is small, have good absorption characteristic to near-infrared portion to far infrared portion
Material is suitable.As this material, the conductive metal oxygen that there is plasma wavelength near infrared region can be enumerated
Compound.Specifically, tin oxide, indium oxide, zinc oxide, tungsten oxide, chromium oxide, molybdenum oxide etc. can be illustrated.Wherein, preferably exist
The light absorption of visible region small tin oxide, indium oxide, zinc oxide.
In addition, the electric conductivity in order to improve these oxides, particularly preferably the 3rd composition of doping.As for the purpose
Dopant, for tin oxide selection Sb, V, Nb, Ta etc., for indium oxide selection Zn, Al, Sn, Sb, Ga, Ge etc., for oxidation
Zinc selection Al, Ga, In, Sn, Sb, Nb etc..
Combined as pigment dispersion of the decentralized medium for binding compositions and containing heat ray shielding metal particle is obtained
The method of thing, can be using heat ray shielding metal particle, near infrared absorption pigment dispersion in as acrylic acid series bonded combination
In the monomer of the main material of thing, then it is polymerized, so as to can obtain target heat ray shielding pigment dispersion composition.Separately
Outward, it is also possible to advance with known method (Japanese Patent Application 2011-203869) and be made dividing for heat ray shielding metal particle
Dispersion liquid, mixes together with the composition of near infrared absorption pigment is in organic solvent dispersed with monomer, monomer is polymerized afterwards,
So as to can obtain target pigment dispersive composition.And then as easier method, can be as acrylic acid series bonded combination
The pigment of distributing (1), obtains composition in the decentralized medium of thing, ready-made to directly mixing in resulting composition
The dispersion liquid of heat ray shielding metal particle, so as to can obtain target pigment dispersive composition.
On decentralized medium used organic solvent, binding compositions or these mixture pigment dispersion composition or
The coating method of the pigment dispersion composition containing heat ray shielding metal particle, is not particularly limited in them, can make
With comma coating machine, bar coater, spin coater, flush coater, roll coater, gravure coater, knife type coater or other various coatings
Device.
Relative to the heat ray shielding metal particle of acrylic acid series binding compositions and dividing for the compound of above-mentioned formula (1)
The ratio of dissipating is determined according to the coating thickness and shielding properties of adhesive layer.As the optics of the film for being coated with pigment dispersion composition
Performance, it is generally desirable to which visible light transmissivity is high, solar transmittance is low, but generally both has proportionate relationship, can be by emphatically
The performance of one party determines optical property.
Generally, it is contemplated that tracing ability and bonding force and economy with joined face, the coating thickness of adhesive layer are usual
Using 10 μm~50 μm of thickness, used as the amount of the particulate for assigning above-mentioned heat ray shielding in this range, preferably (heat is penetrated
The compound of line shielding metal particle+above-mentioned formula (1))：Resin solid content=3:97~1:The scope of 1 (weight ratio).
Embodiment
Enumerate following embodiments 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)
To adding 3.0 parts of phthalic anhydride, 11.9 parts of naphthalene dicarboxylic anhydride, 29 parts of urea, ammonium molybdate 0.40 in 120 parts of sulfolane
3.5 parts of part and divanadyl tetrachloride (V), 200 DEG C are warming up to by resulting composition, are reacted 11 hours at such a temperature.Reaction is eventually
Reaction solution is cooled to 65 DEG C after only, 100 parts of DMF (DMF) is added, precipitation solid is separated by filtration.Use DMF
Solid obtained by 50 parts of cleanings, obtains 20.3 parts of wet cake.During resulting wet cake added into 100 parts of DMF, by gained
To composition be warming up to 80 DEG C, and stir 2 hours at such a temperature.Precipitation solid is separated by filtration, 200 parts are carried out clearly with water
Wash, obtain 18.9 parts of wet cake.By in resulting wet cake 150 parts of water of addition, resulting composition is warming up to 90 DEG C,
And stir 2 hours at such a temperature.Precipitation solid is separated by filtration, 200 parts are cleaned with water, obtains 16.1 parts of wet cake.
Wet cake obtained by 80 DEG C of dryings, obtains 12.3 parts of above-claimed cpd example No.1.The compound very big suction in concentrated sulfuric acid
Receipts wavelength is 943nm.
Embodiment 2 (above-claimed cpd example No.2)
3.0 parts of phthalic anhydride in embodiment 1 is changed into 5.9 parts, 11.9 parts of naphthalene dicarboxylic anhydride is changed into 7.9 parts, remove
12.1 parts of above-claimed cpd example No.2 are obtained beyond this similarly to Example 1.Compound maximum absorption in concentrated sulfuric acid
Wavelength is 951nm, 882nm, 815nm.
Embodiment 3 (above-claimed cpd example No.9)
To adding 3.3 parts of 3,4- pyridinedicarboxylic acids, 7.9 parts of naphthalene dicarboxylic anhydride, 29 parts of urea, ammonium molybdate in 120 parts of sulfolane
0.40 part and 3.5 parts of divanadyl tetrachloride (V), 200 DEG C are warming up to by resulting composition, are reacted 11 hours at such a temperature.Instead
Reaction solution is cooled to 65 DEG C after should terminating, 100 parts of DMF (DMF) is added, precipitation solid is separated by filtration.With
Solid obtained by 80 DEG C 200 parts of cleanings of DMF, obtains 20.3 parts of wet cake.Resulting wet cake is added into DMF 100
In part, resulting composition is warming up to 80 DEG C, and stir 2 hours at such a temperature.Precipitation solid is separated by filtration, water is used
200 parts are cleaned, and obtain 40.1 parts of wet cake.During resulting wet cake added into 150 parts of water, by resulting composition
90 DEG C are warming up to, and are stirred 2 hours at such a temperature.Precipitation solid is separated by filtration, 7.9 parts are cleaned with water, obtain wet filter
35.2 parts of cake.Wet cake obtained by 80 DEG C of dryings, obtains 10.8 parts of above-claimed cpd example No.9.The compound is in the concentrated sulfuric acid
In maximum absorption wavelength be 933nm.
Embodiment 4 (above-claimed cpd example No.10)
3.3 parts of 3,4- pyridinedicarboxylic acids in embodiment 3 is changed into 6.7 parts, 11.9 parts of naphthalene dicarboxylic anhydride is changed into 7.9 parts,
Obtain 11.4 parts of above-claimed cpd example No.10 similarly to Example 3 in addition.The compound very big suction in concentrated sulfuric acid
It is 939nm, 804nm, 711nm to receive wavelength.
Embodiment 5 (above-claimed cpd example No.3)
To the compound N that is obtained in embodiment 1 is added in (116%) 40 part of polyphosphoric acid, o.13.4 part, phthalyl are sub-
4.9 parts of amine, 1.0 parts of paraformaldehyde, are warming up to 140 DEG C, and react 6 hours at such a temperature by resulting composition.Reaction
After termination, reaction solution is cooled to 60 DEG C, adds 100 parts of water.It is separated by filtration precipitation solid water-filling of going forward side by side to wash, obtains wet cake
34.0 parts.
By in resulting wet cake 100 parts of 10% potassium hydroxide aqueous solution of addition, the composition obtained by making is at 50 DEG C
Reaction 2 hours.It is separated by filtration precipitation solid water-filling of going forward side by side to wash, obtains 29 parts of wet cake.
By in resulting 100 parts of DMF of wet cake addition, the composition obtained by making is reacted at 25 DEG C.Filtering point
Isolate solid water-filling of going forward side by side to wash, obtain 13.3 parts of wet cake.Wet cake obtained by 80 DEG C of dryings, obtains 6.5 parts of chemical combination
Thing No.3.Compound maximum absorption wavelength in concentrated sulfuric acid is 949nm.
Embodiment 6 (above-claimed cpd example No.11)
In embodiment 5, o.1 obtained in embodiment 1 3.4 parts of compound Ns are replaced with 3.1 parts obtained in embodiment 4
O.11 o.10, in addition compound N obtain 5.7 parts of compound Ns similarly to Example 5.The compound is in concentrated sulfuric acid
Maximum absorption wavelength is 940nm.
Embodiment 7 (pigment dispersion composition 1)
To compound 0.21g, dispersant that the above-mentioned formula (4) obtained in embodiment 1 is added in toluene 7ml
DisperBYK1400.21g, and then the zirconium oxide bead as broken pearl is added, using batch-type bead mill device (T.K.Fill
Mix 30-25 types, the manufacture of primix companies) carry out decentralized processing.Use centrifugal separator (Hitachi Koki Co., Ltd
HimacCR18 centrifugal treating) is carried out to resulting dispersion, so as to 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, in addition with embodiment 7
Similarly obtain pigment dispersion composition 2~4.
Synthesis example 1 (acrylic acid series binding compositions)
N-butyl acrylate 291g and acrylic acid 9g are dissolved in toluene 366g, azodiisobutyronitrile 0.15g is added,
It is polymerized 6 hours in 70 DEG C under nitrogen stream, obtains acrylic resin copolymer (weight average molecular weight：Mw=32 ten thousand).It is dilute with toluene
The copolymer is released, it is the acrylic acid series binding compositions that 29.36%, viscosity is 2700mPas to obtain solid constituent ratio.
Decentralized medium is the pigment dispersion composition and the group of organic solvent and the mixture of acrylic acid series binding compositions
The making of compound coated sheets
Embodiment 13
Weight portion (the butyl acrylate of acrylic acid series binding compositions 100 that will be obtained in synthesis example 1:Acrylic acid=97:
3) weight portion of pigment dispersion composition 28.1 for, being obtained in embodiment 7 equably mixed dissolution, obtains pigment dispersion composition.
In addition, being applied to polyester film (implementing organosilicon in single-face side to process) (lintec of release sheet using comma coating machine
3811 thickness of company's manufacture：38 μm) on and by dried coating film, (implement organosilicon in single-face side with the polyester film of release sheet
Treatment) (3801 thickness of lintec companies manufacture：38 μm) covered, thus make pigment dispersion composition coated sheets
(thickness：15μm).
Embodiment 14~16
The pigment dispersion composition that will be obtained in embodiment 7 replaces with the pigment dispersion combination obtained in embodiment 8~10
Thing, obtains pigment dispersion composition coated sheets (thickness similarly to Example 13 in addition：15 μm) 2~4.
Comparative example 1
The compound for using the formula (2) described in patent document 1 to represent instead of the pigment obtained in embodiment 1, except this
Pigment dispersion composition is made similarly to Example 7 in addition, has made instead of the pigment dispersion composition obtained in embodiment 7
With the pigment dispersion composition, pigment dispersion composition coated sheets (thickness has been made similarly to Example 13 in addition：15
μm)。
Embodiment 17 (evaluations of pigment dispersion composition coated sheets)
Composition coated sheets to being made in embodiment 13~16, comparative example 1 are evaluated.Test method and result are commented
Valency method is as described below.
The calculating of the transmitance of (a) composition coated sheets
The transmission of composition coated sheets obtained above is determined using spectrophotometer (Shimadzu Seisakusho Ltd. manufactures UV-3150)
Spectrum, calculates transmitance.
The calculating of (b) total sunshine energy (Tts)
Total sunshine energy (Tts：Total Solar Transmittance, total solar energy transmission) it is from the sun
Heat energy using which kind of degree through as object material standard, calculated using the calculating formula defined in ISO13837.Calculated
Smaller then expression of numerical value for going out adds up to sunshine energy smaller, represents that heat ray shielding is higher.
(C) calculating of the b* values of CIE1976 (L*a*b*) colorimeter system
The b* values of CIE1976 (L*a*b*) colorimeter system are the numerical value of the tone of the yellow for representing measuring object,
The more big then yellow tone of numerical value is stronger, and the smaller then yellow tone of numerical value is weaker.The b* values can be by the transmitted light that is obtained in (a)
Spectrum is calculated.
In this evaluation, compare make expression heat ray shielding total sunshine energy (Tts) value it is identical when b* values, and
It is summarized in table 2.
【Table 2】
As shown in table 2, it is known that：Using in the case of pigment of the invention, and identical heat ray shielding is shown
Comparative example is compared, and b* values diminish, and yellow tone significantly mitigates.For the composition coated sheets of embodiment 14, it is impossible to by visual observation
Yellow tone is confirmed, but for the piece of comparative example 1, confirming can be with the strong yellow tone of the visual degree for confirming.
Production Example 1 (heat ray shielding metal particle dispersion liquid)
To adding 11.2 parts of tin indium oxide, 7.0 parts of acetylacetone,2,4-pentanedione, dispersant DisperBYK1401.75 in 70 parts of toluene
Part, so add as crush pearl zirconium oxide bead, using batch-type bead mill device (T.K.Fill Mix 30-25 types,
Primix companies manufacture) carry out decentralized processing.In addition, right using centrifugal separator (Hitachi Koki Co., Ltd himacCR18)
Resulting dispersion (heat ray shielding metal particle dispersion liquid) has carried out centrifugal treating.
Used organic solvent, binding compositions or these mixture as the pigment dispersion composition of decentralized medium or
The making of the coated sheets of the pigment dispersion composition containing heat ray shielding metal particle in them
Embodiment 18
Weight portion (the butyl acrylates of acrylic adhesive A 100 that will be obtained in synthesis example 1:Acrylic acid=97:3)、
The colorant dispersing liquid 14.7 obtained in 144 parts of toluene dispersion liquid, the embodiment 7 of the stanniferous indium oxide (ITO) obtained in Production Example 1
Part equably mixed dissolution, obtains heat ray shielding binding compositions.In addition, being applied to the demoulding using comma coating machine
Polyester film (implementing organosilicon treatment in single-face side) (3811 thickness of lintec companies manufacture of piece：38 μm) on and by film
Dry, with polyester film (implementing organosilicon in single-face side to process) (3801 thickness that lintec companies manufacture of release sheet：38μ
M) covered, thus made pigment dispersion composition coated sheets (thickness：15μm).
Comparative example 2
The pigment dispersion composition made in comparative example 1 is used instead of the colorant dispersing liquid obtained in embodiment 7, except this
The pigment dispersion composition coated sheets containing heat ray shielding metal particle are made similarly to Example 18 in addition (thick
Degree：15μm).
Embodiment 19
The piece obtained in embodiment 18, comparative example 2 is evaluated similarly to Example 17.Its result is summarized in
In table 3.
【Table 3】
As shown in table 3, it is known that：Even if using to the group by the porphyrazine pigment dispersion of (1) in decentralized medium
In the case of mixing pigment dispersion composition obtained from heat ray shielding metal particle dispersion liquid in compound, also with embodiment
Evaluation result shown in 19 is same, the pigment dispersion composition phase with the pigment represented using the formula (2) described in patent document 1
Than b* values diminish, and are not influenceed by heat ray shielding metal particle is whether there is, and significantly alleviate yellow tone.
Industrial applicibility
The present invention provides that a kind of heat ray shielding ability is excellent, yellow tone is few, aesthetic property is excellent used as heat ray screen
The near infrared absorption pigment of covering property material.In addition, resulting near infrared absorption pigment can apply to towards house, automobile
The heat ray shielding material of glass pane, extremely has value in practical.
Claims (10)
1. the porphyrazine pigment that a kind of following formula (1) represents,
In formula (1), M represents 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, and X represents that the low alkyl group that carbon number is 1~4, carbon number are 1~4
Lower alkoxy, amino, nitro, halogen, hydroxyl, carboxyl, sulfonic group, sulfoamido, Y represent selected from by carbon number be 1
~3 alkylidene ,-CO2-、-SO2- and-SO2NH(CH2) c- composition group in divalence crosslinked group, wherein, c represents 0~4,
Z represent sulfonic group, carboxyl or with or without substitution base phthalimide-based, with or without substitution base
Piperazinyl, the piperidyl with or without substitution base, wherein, the substitution base is that hydrogen atom, carbon number are 1~4
Alkyl, carbon number are 1~4 alkoxy, substituted-amino, nitro, halogen or sulfonic group, wherein, in the substituted-amino
Substitution base is the alkyl that carbon number is 1~4, and a and b is average value, and a, b are respectively less than more than 0 12, and a and b sums are
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 the alkylidene that carbon number is 1~3, Z
It is the phthalimide-based or the piperazinyl with or without substitution base with or without substitution base.
4. porphyrazine pigment as claimed in claim 1, wherein, the M in formula (1) is VO.
5. a kind of pigment dispersion composition, it is characterised in that it is by the porphyrazine pigment any one of Claims 1 to 4
It is scattered in decentralized medium.
6. pigment dispersion composition as claimed in claim 5, it is characterised in that decentralized medium is acrylic acid series bonded combination
Thing.
7. a kind of piece, it is formed by the pigment dispersion composition being coated with described in claim 6.
8. pigment dispersion composition as claimed in claim 6, it is characterised in that contain heat ray shielding metal particle.
9. pigment dispersion composition as claimed in claim 8, wherein, described heat ray shielding metal particle is oxidation
Any one in tin, indium oxide or zinc oxide.
10. a kind of piece, it is formed by the pigment dispersion composition being coated with described in claim 9.
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| CN201380031619.2A CN104395409B (en) | 2012-06-18 | 2013-06-11 | Porphyrazine pigment and application thereof |
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| 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 |
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- 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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2016
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Also Published As
| Publication number | Publication date |
|---|---|
| CN104395409A (en) | 2015-03-04 |
| JPWO2013191029A1 (en) | 2016-05-26 |
| WO2013191029A1 (en) | 2013-12-27 |
| KR20150023250A (en) | 2015-03-05 |
| TW201402709A (en) | 2014-01-16 |
| 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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