CN104395409B - Porphyrazine pigment and application thereof - Google Patents
Porphyrazine pigment and application thereof Download PDFInfo
- Publication number
- CN104395409B CN104395409B CN201380031619.2A CN201380031619A CN104395409B CN 104395409 B CN104395409 B CN 104395409B CN 201380031619 A CN201380031619 A CN 201380031619A CN 104395409 B CN104395409 B CN 104395409B
- Authority
- CN
- China
- Prior art keywords
- formula
- pigment
- pigment dispersion
- group
- porphyrazine
- Prior art date
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- Expired - Fee Related
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- 239000000049 pigment Substances 0.000 title claims abstract description 95
- 239000000203 mixture Substances 0.000 claims abstract description 94
- 239000006185 dispersion Substances 0.000 claims abstract description 59
- 238000000034 method Methods 0.000 claims abstract description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 125000004429 atom Chemical group 0.000 claims abstract description 8
- 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
- 229910044991 metal oxide Inorganic materials 0.000 claims abstract description 7
- 150000004706 metal oxides Chemical class 0.000 claims abstract description 7
- 229910000000 metal hydroxide Inorganic materials 0.000 claims abstract description 5
- 150000004692 metal hydroxides Chemical class 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 229910001507 metal halide Inorganic materials 0.000 claims abstract description 4
- 150000005309 metal halides Chemical class 0.000 claims abstract description 4
- -1 substituted-amino Chemical group 0.000 claims description 25
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 20
- 239000002923 metal particle Substances 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
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- 238000000576 coating method Methods 0.000 claims description 13
- 239000011248 coating agent Substances 0.000 claims description 12
- 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 12
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
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- 125000001118 alkylidene group Chemical group 0.000 claims description 6
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
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- 239000011787 zinc oxide Substances 0.000 claims description 5
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- 239000002184 metal Substances 0.000 claims description 3
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- 239000001257 hydrogen Substances 0.000 abstract description 7
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- 125000000623 heterocyclic group Chemical group 0.000 abstract description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract description 2
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- 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
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 125000004193 piperazinyl group Chemical group 0.000 description 3
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- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-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
- 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
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000003522 acrylic cement Substances 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 238000004378 air conditioning Methods 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 125000005211 alkyl trimethyl ammonium group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical group CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- RNOOHTVUSNIPCJ-UHFFFAOYSA-N butan-2-yl prop-2-enoate Chemical group CCC(C)OC(=O)C=C RNOOHTVUSNIPCJ-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 238000005119 centrifugation Methods 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
- 239000003086 colorant Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical group O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 238000010130 dispersion processing Methods 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
- 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
- 238000011049 filling Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 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
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000004519 grease Substances 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-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000002466 imines Chemical class 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
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000011733 molybdenum Substances 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
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
- 229910052762 osmium Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920002866 paraformaldehyde Polymers 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
- 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
- 229920001155 polypropylene 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
- 238000001556 precipitation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 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
- 230000000630 rising effect Effects 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
- 238000009738 saturating Methods 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
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229910021509 tin(II) hydroxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 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
- 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
- 238000005406 washing Methods 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
nullThe present invention relates to 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) during C difference)，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 obtain，A and b is meansigma methods，a、B is respectively less than more than 0 12，And a Yu b sum is less than more than 0 12] the porphyrazine pigment that represents and the pigment dispersion compositions containing this porphyrazine pigment.
Description
Technical field
The present invention relates to a kind of specific near infrared region demonstrate excellence absorption, the transmitance of visible region
Height, the new-type porphyrazine pigment not damaging aesthetic property and application thereof.
Background technology
In recent years, from the standpoint of energy-conservation, global environmental problems etc., it is desirable to alleviate the load of air-conditioning equipment.Such as exist
House, automobile field in, have and maskable be attached to window from the heat ray shielding material of the heat ray of sunlight
Heat ray shielding glass on glass, it has inhibition to the temperature rising in indoor, car, penetrates as this heat
Line shielding material, employs near infrared absorption pigment.
When this heat ray shielding material is attached on the glass pane of house or automobile, from guarantee observability in terms of examine
Consider, it is desirable to visible light transmissivity is high；Additionally from the standpoint 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 standpoint of aesthetic property, it is desirable to the greatest extent
Possible water white transparency or colour shallow.
In patent documentation 1, as the heat ray shielding material that the transparency is excellent, disclose porphyrazine pigment.But
It is, the present inventor the result studied, although the pigment visible light transmissivity described in patent documentation 1 is high, hot
Alpha ray shield is the most 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 is to be solved
The present invention is carried out in view of above-mentioned condition, it is an object of the invention to provide a kind of visible light transmissivity high,
And the porphyrazine pigment that heat ray shielding is excellent.It addition, it is an object of the invention to provide can suppress yellow tone,
Even if the most not damaging aesthetic property in the field of house or automobile, porphyrazine color that industrial value is improved
Element and the heat ray shielding compositions containing this pigment.
For solving the scheme of problem
The present inventor conducts in-depth research for solving above-mentioned problem, it was found that specific following formula (1) represents
Porphyrazine pigment or above-mentioned problem can be solved containing the pigment dispersion compositions of this porphyrazine pigment, this completes this
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 represent metallic atom, metal-oxide, metal hydroxides or metal halide or
Hydrogen atom, ring A, B, C are each independently following formula (2)～(8)
But (being above-mentioned formula (8) during A, B, C difference), the * in above-mentioned formula (2)～(8) represents bonding position, X table
Show low alkyl group, lower alkoxy, amino, nitro, halogen, hydroxyl, carboxyl, sulfonic group, sulfoamido, Y
Representing bivalence crosslinked group, Z represents sulfonic group, carboxyl, is removed extremely by the hydrogen on the nitrogen-atoms of primary amino radical or secondary amino group
Few 1 and the residue that obtains or the hydrogen on the nitrogen-atoms of the heterocycle comprising nitrogen is removed at least 1 and obtain residual
Base, a and b is meansigma methods, and a, b are respectively less than more than 0 12, and a Yu b sum is less than more than 0 12].
(2) the porphyrazine pigment as described in (1), wherein, ring A, B, the C in formula (1) be respectively formula (2), formula (4) or
Formula (8).
(3) the porphyrazine pigment as described in (1), wherein, ring A, B, the C in formula (1) is 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 be carbon number be the alkylidene of 1～3,
Z is the phthalimide-based with or without substituent group or the piperazinyl with or without substituent group.
(6) the porphyrazine pigment that a kind of following formula (9) represents.
[ring A, B, the C in formula (1) is respectively formula (4) or formula (8) (but during A, B, C difference being formula (8))].
(7) a kind of pigment dispersion compositions, it is characterised in that it is by the porphyrazine pigment according to any one of (1)～(6)
It is scattered 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 penetrate containing heat in the pigment dispersion compositions described in (8)
Line shielding metal particle.
(11) a kind of pigment dispersion compositions, wherein, the heat ray shielding metal particle described in (10) be stannum oxide,
Any one in 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 by the porphyrazine pigment of the present 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, do not damage aesthetic property, can be by this Thallus Porphyrae
Piperazine pigment is applied in the field of house or automobile.
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
It is scattered in various disperse medium, makes 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 spy can being applied in heat ray shielding bonding sheet
Levy.
In above-mentioned formula (1), as the aromatic rings in ring A～C represented by dotted line, such as with phenyl ring or naphthalene nucleus as representative,
The nitrogenous heteroaromatic containing 1 or 2 nitrogen-atoms such as pyridine ring, pyrazine ring, pyridazine ring can be enumerated.Among these,
The preferably combination of phenyl ring, pyridine ring, naphthalene nucleus, the more preferably combination of pyridine ring, naphthalene nucleus.It addition, pyridine ring is most preferably
For above-mentioned formula (4).
In above-mentioned formula (1), M represents hydrogen atom, metallic atom, metal-oxide, metal hydroxides or gold
Belong to halogenide.M be beyond hydrogen atom in the case of, this M refer to the porphyrin ring in formula (1) have so-called center gold
Belong to.It addition, in the case of M is hydrogen atom, refer to that this porphyrin ring does not have central metal.
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, can enumerate such as
Si(OH)2、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, preferably Fe, Co, Cu, Ni, Zn,
The metallic atoms such as Al, V；The metal-oxides such as VO；The metal hydroxidess etc. such as AlOH.More preferably can enumerate
Cu, VO, most preferably VO.
X in above-mentioned formula (1) represent 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, can enumerate alkylidene ,-CO that such as carbon number is 1～32-、-SO2-、
-SO2NH(CH2) c-(herein, c represents 0～4), preferably carbon number be 1～3 alkylidene, c be 0
-SO2NH-, more preferably carbon number are the alkylidene of 1～3.Z represent sulfonic group, carboxyl, by primary amino radical or parahelium
Residue that hydrogen on the nitrogen-atoms of base removes at least 1 and obtains or by the hydrogen on the nitrogen-atoms of the heterocycle comprising nitrogen
The residue removing at least 1 and obtain, such as, can illustrate carboxyl, sulfonic group, adjacent benzene with or without substituent group
Dicarboximide base, the piperazinyl with or without substituent group, the piperidyl etc. with or without substituent group, excellent
Select carboxyl, sulfonic group, phthalimide-based with or without substituent group, preferably with or without replacement
The phthalimide-based of base.It should be noted that be the phthalyl with or without substituent group as Z
Substituent group when imido grpup, the piperazinyl with or without substituent group, the piperidyl with or without substituent group,
Hydrogen atom, low alkyl group, lower alkoxy, substituted-amino, nitro, halogen, sulfonic group, preferably hydrogen can be shown
Atom, halogen.
In the present invention, substituted-amino is not particularly limited, comprises such as low alkyl group or lower alkoxy and replace and obtain
The amino arrived." 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) is respectively less than more than 0 12, and a Yu b sum is less than more than 0 12.Excellent
Selecting a, b to be respectively less than more than 04, a Yu b sum is less than more than 04.
Ring A～C in the porphyrazine pigment of the present invention that above-mentioned formula (1) is represented, the concrete example of X, Y and Z, a
It is shown in table 1 below with the numerical value of b.
In order to illustrate the pigment of the present invention, following example shows representational pigment, but the present invention is not limited to
Following example.It addition, in the case of the nitrogenous heteroaromatic of ring A～C is above-mentioned formula (2), (3) and (5), there is nitrogen
The position isomer of atom, when synthetic dyestuff, the form with the mixture of isomer obtains.The separation of these isomers
Difficulty, and be difficult to by analysis, isomer is determined.Therefore, generally use with the state of mixture.This
The pigment of invention also comprises such mixture.In this specification, do not distinguish these isomers etc., using structural formula table
In the case of showing, 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 according to No. 2010/143619 pamphlet of International Publication and
Known method disclosed in No. 2010/013455 pamphlet of International Publication synthesizes.It addition, the purple that formula (1) represents
Dish piperazine pigment can also synthesize as follows: when utilizing known nitrile method or Wheeler method to synthesize, makes as reaction
Above-mentioned formula (2)～the mixed ratio of (7) respective derivant and naphthalene diacid derivative that raw material uses change, thus
Can synthesize.It should be noted that as described in document as known in above-mentioned, by said method obtain above-mentioned
The compound that formula (1) represents also becomes the position of substitution with the nitrogenous heteroaromatic in ring A～C and nitrogenous heteroaromatic
The mixture of the position isomer that the position of substitution of nitrogen-atoms is relevant.
Compound N in table 1 is o.3 or the compound that represents of No.18 such as can be according to Japanese Patent No. 2507786
Disclosed in number pamphlet, No. 2010/013455 pamphlet of International Publication and No. 3813750 pamphlets of Japanese Patent No.
Known method synthesizes.
As the method that the compound of above-mentioned formula (1) is scattered in disperse medium, it is possible to use existing method.That is,
The compound of above-mentioned formula (1) and disperse medium can be mixed with special ratios, be added as needed on dispersant, surface
Activating agent etc., and utilize the dispersal devices such as sand mill, grater, ball mill, homogenizer, edge runner, ball mill to enter
Row dispersion.Preferred ball mill among these.It addition, in the pulverizing of pigment in ball mill, diameter is preferably used little
Pearl, increase the filling rate etc. of pearl, thus process improving under conditions of crush efficiency, and then preferably pulverizing
By filtration, centrifugation etc., pearl is removed after process.
The disperse medium used in dispersion is not particularly limited, the present invention refers to water, organic solvent, bonded combination
Thing etc..It addition, these disperse medium can also use as mixture after mixing.As organic solvent, can enumerate
Such as hydrocarbon system solvent (toluene, dimethylbenzene, hexane, hexamethylene, normal heptane etc.), alcohol series solvent are (methanol, ethanol, different
Propanol, butanol, the tert-butyl alcohol, benzyl alcohol etc.), ketone series solvent (acetone, methyl ethyl ketone, methyl iso-butyl ketone (MIBK), two
Isobutyl ketone, Ketohexamethylene, acetylacetone,2,4-pentanedione etc.), ester series solvent (ethyl acetate, methyl acetate, butyl acetate, acetic acid
Cellosolve, pentyl acetate etc.), ether series solvent (diisopropyl ether, methyl cellosolve, butyl cellosolve, 1,4-dioxane
Deng), glycol series solvent (ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol etc.), glycol ethers series solvent (diethyl two
Alcohol monomethyl ether, propylene glycol monomethyl ether etc.), glycol ester series solvent (ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether
Acetas, 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,N-dimethylformamide, N, N-diformazan
Yl acetamide, 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, Methylethyl
Ketone, methyl iso-butyl ketone (MIBK), acetylacetone,2,4-pentanedione.
It addition, in the case of disperse medium is acrylic acid series binding compositions, acrylic acid that durability high is preferably used
Copolymerization system binder resin.Acrylic acid copolymer system binder resin generally can be turned by vitrification when making polymer
The copolymerization of principal monomer that temperature is low and the high comonomer of glass transition temperature makes.
For the monomer of the raw material as acrylic acid copolymer system binder resin, vitrification when making polymer can be used
Transition temperature is low, the carbon number of alkyl is the alkyl acrylate of 2～14 or the carbon number of alkyl is 4～16
Alkyl methacrylate and glass transition temperature when making polymer is higher than above-mentioned monomer and can be with it
Copolymerization monomer.
As the alkyl acrylate monomer that glass transition temperature when making polymer is low, can be with exemplary propylene acid second
Ester, n-propyl, acrylic acid isopropyl, methoxyethyl acrylate, acrylic acid normal-butyl, i-butyl
Ester, acrylic acid sec-butyl, acrylic acid-2-ethyl caproite, n-octyl, Isooctyl acrylate monomer, acrylic acid are different
Nonyl ester, the different stearyl ester of acrylic acid etc..
It addition, as the low alkyl methacrylate monomer of glass transition temperature when making polymer, permissible
Illustrate methacrylic acid-2-Octyl Nitrite, n octyl methacrylate, the positive lauryl of methacrylic acid etc..
It addition, as can the monomer of copolymerization, can illustrate vinyl acetate, acrylonitrile, acrylamide, styrene,
Methyl methacrylate, acrylic acid methyl ester. etc..
In addition to 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) propylene
Acid dimethylaminoethyl, acrylamide, n-methylolacrylamide, DMAA, Glycidyl methacrylate are sweet
Grease, 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.
More preferably 200,000～800,000.
Constitute the degree of cross linking of macromolecular material of binding compositions according to various conditions such as the kind of macromolecular material, compositions
And different, it is not particularly limited, it may be necessary in macromolecular material, add plasticizer.As this plasticizer, permissible
Enumerate phthalic acid ester, trimellitate, pyromellitic ester, adipate ester, sebacate, phosphotriester or second
The esters such as diol ester；Or operation oil, liquid polyethers, liquid polyterpene, other liquid resin etc., can be by these it
In one kind or two or more be used in mixed way.Such plasticizer is preferably the plasticising good with the compatibility of binding compositions
Agent.It addition, in addition to above-mentioned plasticizer, it may be necessary in binding compositions, add such as UV absorbent
Or the various additives such as antioxidant.
About compound and the weight ratio of disperse medium of the above-mentioned formula (1) when disperseing, by the chemical combination of above-mentioned formula (1)
Thing is set to 1, in contrast, preferably disperse medium is 3～500, further preferred disperse medium is 15～100,
Preferably disperse medium is 20～50.
As dispersant, representative is soap (soap), alpha-sulfo fatty acid ester salt (MES), alkyl
Benzene sulfonate (ABS), linear alkylbenzene sulfonate (LAS) (LAS), alkyl sulfate (AS), alkyl ether sulphate salts (AES),
Low molecule anion (anion) the property compound of alkylsurfuric acid three ethanol ester etc；Fatty acid ethanol amide, polyoxyethylene
The low molecule nonionic of alkyl ether (AE), polyoxyethylene alkyl phenyl ether (Α Ρ Ε), Sorbitol, sorbitol anhydride etc
Based compound；Alkyl trimethyl ammonium salt, dialkyl dimethyl ammonium chloride, alkylpyridinium chlorides etc low molecule sun from
Son (cation) property compound；The low molecule both sexes system chemical combination of alkyl carboxyl glycine betaine, sulfobetaines, lecithin etc
Thing；Formaldehyde condensation products, poly styrene sulfonate, polyacrylate, vinyl compound and carboxylic acid with naphthalene sulfonate
Be the copolymer salt of monomer, carboxymethyl cellulose, polyvinyl alcohol etc. be representative macromolecule water system dispersant；Polypropylene
The macromolecule non-water system dispersant of acid moieties Arrcostab, polyalkylene polyamine etc；Polymine, methacrylic acid
The macromolecule cation system dispersant of aminoalkyl ester copolymer etc, but as long as the present invention can be highly suitable for
Granule, be just not excluded for the dispersant with the structure beyond the material of form illustrated therein.
As the dispersant added, if enumerating specific name, it is known that following material.Flowlen can be illustrated
DOPA-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 32000、
Solsperse 35100, Solsperse 54000, SOLTHIX 250, (Japan 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 (EFKA Additives company manufacture), AJISPER
PA111、AJISPER PB711、AJISPER PB821、AJISPER PB822、AJISPER PN411、FAMEX
L-12 (Ajinomoto Fine-Techno company manufacture), TEXAPHOR-UV21,
TEXAPHOR-UV61 (Cognis Japan company manufacture), 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(BYK-Chemie
Japan company manufacture), 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 (nanmu this chemical conversion strain formula meeting
Society), 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, Ftergent 750DM, Ftergent 750FM (manufacture of NEOS company), AS-1100, AS-1800,
AS-2000 (Toagosei Co., Ltd's manufacture), KAOCER 2000, KAOCER 2100, KDH-154,
MX-2045L、HOMOGENOL L-18、HOMOGENOL L-95、RHEODOL SP-010V、
RHEODOL SP-030V, RHEODOL SP-L10, RHEODOL SP-P10 (Kao Corp's manufacture),
EPAN U103、SHALLOL DC902B、NOIGEN EA-167、PLYSURF A219B、PLYSURF
AL (Di-ichi Kogyo Seiyaku Co., Ltd.'s manufacture), MEGAFAC F-477, MEGAFAC 480SF, MEGAFAC
F-482 (Dainippon Ink Chemicals's manufacture), Silface SAG503A, Dynol 604 (Nishin Chemical Industry Co. Lt's manufacture),
SN SPERSE 2180, SN SPERSE 2190, SN Leveller S-906 (SAN NOPCO Co., Ltd. manufacture),
The material of S-386, S-420 (AGC SEIMI CHEMICAL Co., Ltd. manufacture) etc.
In the case of the pigment dispersion compositions of the present invention contains heat ray shielding metal particle, as used
Heat ray shielding metal particle, it is seen that absorbing of light is little, have good absorption to near-infrared portion to far infrared portion special
The material of property is suitable.As this material, the conduction near infrared region with plasma wavelength can be enumerated
Property metal-oxide.Specifically, stannum oxide, Indium sesquioxide., zinc oxide, tungsten oxide, chromium oxide, oxygen can be illustrated
Change molybdenum etc..Wherein, preferably at the little stannum oxide of the light absorption of visible region, Indium sesquioxide., zinc oxide.
It addition, for the electric conductivity improving these oxides, particularly preferably doping the 3rd composition.As for the purpose
Alloy, Sb, V, Nb, Ta etc. are selected for stannum oxide, for Indium sesquioxide. select Zn, Al, Sn, Sb,
Ga, Ge etc., select Al, Ga, In, Sn, Sb, Nb etc. for zinc oxide.
It is binding compositions and the combination of the pigment dispersion containing heat ray shielding metal particle as obtaining disperse medium
The method of thing, can be using heat ray shielding metal particle, near infrared absorption pigment dispersion in bonding as acrylic acid series
In the monomer of the main material of compositions, then it is polymerized, thus available target heat ray shielding pigment dispersion group
Compound.Alternatively, it is also possible to advance with known method (Japanese Patent Application 2011-203869) to make heat ray shielding
The dispersion liquid of metal particle, mixes with monomer together with being dispersed with the compositions of near infrared absorption pigment in organic solvent
Close, make monomer be polymerized afterwards, thus available target pigment dispersive composition.And then as easier method, can
Using the pigment of distributing (1) in the disperse medium as acrylic acid series binding compositions, obtain compositions, to gained
To compositions in directly mix the dispersion liquid of ready-made heat ray shielding metal particle, thus available target
Pigment dispersion compositions.
About disperse medium employ organic solvent, binding compositions or these mixture pigment dispersion compositions or
They contain the coating process of the pigment dispersion compositions of heat ray shielding metal particle, is not particularly limited, can
With use comma coating machine, bar coater, spin coater, flush coater, roll coater, gravure coater, knife type coater or
Other various apparatus for coating.
Relative to acrylic acid series binding compositions heat ray shielding metal particle and above-mentioned formula (1) compound point
The ratio of dissipating determines according to coating thickness and the shielding properties of adhesive layer.As the film being coated with pigment dispersion compositions
Optical property, it is generally desirable to visible light transmissivity is high, solar transmittance is low, but generally both has proportionate relationship,
Optical property can be determined by the performance of one party emphatically.
Generally, it is contemplated that with the tracing ability of joined face and bonding force and economy, the coating thickness of adhesive layer is usual
Use 10 μm～the thickness of 50 μm, as the amount of the microgranule giving above-mentioned heat ray shielding in this range, excellent
Elect (compound of heat ray shielding metal particle+above-mentioned formula (1)): resin solid content=3:97～1:1 (weight ratio) as
Scope.
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)
Phthalic anhydride 3.0 parts, naphthalene dicarboxylic anhydride 11.9 parts, urea 29 parts, molybdic acid is added in sulfolane 120 parts
Ammonium 0.40 part and divanadyl tetrachloride (V) 3.5 parts, be warming up to obtained compositions 200 DEG C, react 11 at such a temperature
Hour.After reaction terminating, reactant liquor is cooled to 65 DEG C, adds DMF (DMF) 100 parts, filter
Separate and separate out solid.Solid obtained by cleaning with DMF 50 parts, obtains wet cake 20.3 parts.By obtained
Wet cake adds in DMF 100 parts, and obtained compositions is warming up to 80 DEG C, and stirring 2 is little at such a temperature
Time.Filter to separate and separate out solid, be carried out with 200 parts of water, obtain wet cake 18.9 parts.By obtained wet
Filter cake adds in 150 parts of water, and obtained compositions is warming up to 90 DEG C, and stirring 2 hours at such a temperature.
Filter to separate and separate out solid, be carried out with 200 parts of water, obtain wet cake 16.1 parts.Obtained by being dried at 80 DEG C
Wet cake, obtain 12.3 parts of above-claimed cpd examples 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 examples No.2 the most similarly to Example 1.This compound is in concentrated sulfuric acid
Maximum absorption wavelength is 951nm, 882nm, 815nm.
Embodiment 3 (above-claimed cpd example No.9)
3,4-dipicolinic acid 3.3 parts, naphthalene dicarboxylic anhydride 7.9 parts, urea 29 parts, molybdic acid is added in sulfolane 120 parts
Ammonium 0.40 part and divanadyl tetrachloride (V) 3.5 parts, be warming up to obtained compositions 200 DEG C, react 11 at such a temperature
Hour.After reaction terminating, reactant liquor is cooled to 65 DEG C, adds DMF (DMF) 100 parts, filter
Separate and separate out solid.Solid obtained by cleaning with the DMF 200 parts of 80 DEG C, obtains wet cake 20.3 parts.By institute
The wet cake obtained adds in DMF 100 parts, obtained compositions is warming up to 80 DEG C, and stirs at such a temperature
Mix 2 hours.Filter to separate and separate out solid, be carried out with 200 parts of water, obtain wet cake 40.1 parts.By gained
To wet cake add in 150 parts of water, obtained compositions is warming up to 90 DEG C, and stirs 2 at such a temperature
Hour.Filter to separate and separate out solid, be carried out with 7.9 parts of water, obtain wet cake 35.2 parts.It is dried at 80 DEG C
Obtained wet cake, obtains 10.8 parts of above-claimed cpd examples No.9.This compound maximum absorption in concentrated sulfuric acid
Wavelength is 933nm.
Embodiment 4 (above-claimed cpd example No.10)
Make 3 in embodiment 3,4-dipicolinic acid 3.3 parts become 6.7 parts, make naphthalene dicarboxylic anhydride 11.9 parts become 7.9
Part, obtain 11.4 parts of above-claimed cpd examples No.10 the most similarly to Example 3.This compound is at concentrated sulphuric acid
In maximum absorption wavelength be 939nm, 804nm, 711nm.
Embodiment 5 (above-claimed cpd example No.3)
Compound N o.13.4 part, the phthalyl obtained in embodiment 1 is added in polyphosphoric acid (116%) 40 part
Imines 4.9 parts, paraformaldehyde 1.0 parts, be warming up to obtained compositions 140 DEG C, and react 6 at such a temperature
Hour.After reaction terminating, reactant liquor is cooled to 60 DEG C, adds 100 parts of water.Filter separation precipitation solid to go forward side by side
Row washing, obtains wet cake 34.0 parts.
Obtained wet cake is added in 10% potassium hydroxide aqueous solution 100 parts, make obtained compositions at 50 DEG C
React 2 hours.Filter to separate and separate out solid and wash, obtain wet cake 29 parts.
Obtained wet cake is added in DMF 100 parts, makes obtained compositions react at 25 DEG C.Cross
Filter separates and separates out solid and wash, and obtains wet cake 13.3 parts.Wet cake obtained by being dried at 80 DEG C,
To 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 embodiment 4 obtains in embodiment 1
O.11 o.10 3.1 parts of compound Ns, obtain 5.7 parts of compound Ns the most similarly to Example 5.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 obtained in embodiment 1 is added in toluene 7ml
DisperBYK1400.21g, and then add the zirconium oxide bead as broken pearl, utilize batch-type bead mill device (T.K.Fill
Mix 30-25 type, primix company manufacture) carry out dispersion process.Use centrifugal separator (Hitachi Koki Co., Ltd
HimacCR18) it is centrifuged obtained dispersion processing, thus obtains 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, in addition with reality
Execute example 7 and similarly obtain pigment dispersion compositions 2～4.
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,
It is polymerized 6 hours in 70 DEG C under nitrogen flowing, obtains 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 that the acrylic acid series of 2700mPas glues
Polymeric composition.
Disperse medium is pigment dispersion compositions and this group of the mixture of organic solvent and acrylic acid series binding compositions
The making of compound coated sheets
Embodiment 13
By acrylic acid series binding compositions 100 weight portion (butyl acrylate: acrylic acid=97:3) obtained in synthesis example 1,
The pigment dispersion compositions 28.1 weight portion mixed dissolution equably obtained in embodiment 7, obtains pigment dispersion combination
Thing.It addition, the polyester film utilizing comma coating machine to be applied to release sheet (implements at organosilicon in one side side
Reason) (3811 thickness that lintec company manufactures: 38 μm) upper and by dried coating film, with the polyester film of release sheet (at one side
Side implement organosilicon process) (lintec company manufacture 3801 thickness: 38 μm) cover, thus made color
Element dispersive composition coated sheets (thickness: 15 μm).
Embodiment 14～16
The pigment dispersion compositions obtained in embodiment 7 is replaced with the pigment dispersion combination obtained in embodiment 8～10
Thing, obtains pigment dispersion compositions coated sheets (thickness: 15 μm) 2～4 the most similarly to Example 13.
Comparative example 1
Replace the pigment obtained in embodiment 1 and the compound using the formula (2) described in patent documentation 1 to represent, remove
Make pigment dispersion compositions beyond this similarly to Example 7, replace the pigment dispersion group obtained in embodiment 7
Compound and use this pigment dispersion compositions, made pigment dispersion compositions the most similarly to Example 13
Coated sheets (thickness: 15 μm).
Embodiment 17 (evaluation of pigment dispersion compositions coated sheets)
The compositions coated sheets made in embodiment 13～16, comparative example 1 is evaluated.Test method and result
Evaluation methodology as described below.
The calculating of the transmitance of (a) compositions coated sheets
Spectrophotometer (Shimadzu Seisakusho Ltd. manufactures UV-3150) is utilized to measure the transmission of compositions coated sheets obtained above
Spectrum, calculates transmitance.
B () adds up to the calculating at energy at sunshine (Tts)
Adding up to energy at sunshine (Tts:Total Solar Transmittance, total solar energy transmission) is the heat from the sun
The calculating formula defined in ISO13837 can be utilized to calculate using which kind of degree through the standard of the material as object.Institute
The numerical value the least then expression total energy at sunshine calculated is the least, represents that heat ray shielding is the highest.
(C) calculating of the b* value of CIE1976 (L*a*b*) colorimeter system
The b* value of CIE1976 (L*a*b*) colorimeter system is the numerical value of the tone of the yellow representing measuring object,
The biggest then yellow tone of numerical value is the strongest, and the least then yellow tone of numerical value is the most weak.This b* value can be saturating by obtain in (a)
Penetrate spectrum to calculate.
In this evaluation, compare b* value when making total energy at sunshine (Tts) value of expression heat ray shielding identical, and
It is summarized in table 2.
[table 2]
As shown in table 2, it is known that: in the case of the pigment using the present invention, and demonstrate identical heat ray shielding
Comparative example compare, b* value diminishes, and yellow tone significantly alleviates.For the compositions coated sheets of embodiment 14, nothing
Method is by being visually confirmed to be yellow tone, but for the sheet of comparative example 1, confirming can be with the degree that is visually confirmed to be
Strong yellow tone.
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 is added in toluene 70 parts
Part, so add as crush pearl zirconium oxide bead, utilize batch-type bead mill device (T.K.Fill Mix 30-25 type,
Primix company manufactures) carry out dispersion process.It addition, use centrifugal separator (Hitachi Koki Co., Ltd himacCR18)
Obtained dispersion (heat ray shielding metal particle dispersion liquid) has been carried out centrifugal treating.
Employ organic solvent, binding compositions or these mixture as the pigment dispersion compositions of disperse medium or
They contain the making of the coated sheets of the pigment dispersion compositions of heat ray shielding metal particle
Embodiment 18
By acrylic adhesive A 100 weight portion (butyl acrylate: acrylic acid=97:3) obtained in synthesis example 1,
The pigment manufacture in example 1 the toluene dispersion liquid 144 parts of stanniferous Indium sesquioxide. (ITO) obtained, obtaining in embodiment 7 divides
Dissipate liquid 14.7 parts mixed dissolution equably, obtain heat ray shielding binding compositions.It addition, utilize comma to be coated with
Machine is applied to polyester film (implementing organosilicon to process in one side side) (the 3811 of lintec company manufacture of release sheet
Thickness: 38 μm) go up and by dried coating film, with polyester film (implementing organosilicon to process in one side the side) (lintec of release sheet
Company manufacture 3801 thickness: 38 μm) cover, thus made pigment dispersion compositions coated sheets (thickness:
15μm)。
Comparative example 2
Replace the colorant dispersing liquid obtained in embodiment 7 to use the pigment dispersion compositions of making in comparative example 1, remove
The pigment dispersion compositions coating containing heat ray shielding metal particle has been made similarly to Example 18 beyond this
Sheet (thickness: 15 μm).
Embodiment 19
Similarly to Example 17 the sheet obtained in embodiment 18, comparative example 2 is evaluated.Its result is returned
It is contained in table 3.
[table 3]
As shown in table 3, it is known that: though use to by the porphyrazine pigment dispersion of (1) in disperse medium
Heat of mixing alpha ray shield metal particle dispersion liquid in compositions and in the case of the pigment dispersion compositions that obtains, also with
Evaluation result shown in embodiment 19 is same, with the pigment of the pigment using the formula (2) described in patent documentation 1 to represent
Dispersive composition is compared, and b* value diminishes, and is not affected by with or without heat ray shielding metal particle, significantly alleviates
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 as heat ray screen
The near infrared absorption pigment of covering property material.It addition, obtained near infrared absorption pigment can apply to towards house,
The heat ray shielding material of the glass pane of automobile, the most extremely has value.
Claims (11)
1. the porphyrazine pigment that following formula (1) represents,
In formula (1), M represent metallic atom, metal-oxide, metal hydroxides or metal halide or
Hydrogen atom, ring A, B and C be each independently following formula (2), (3), (5)～(8),
But during A, B, C difference being above-mentioned formula (8), the * in above-mentioned formula (2), (3), (5)～(8) represents bonding part
Position, X represent alkoxyl that alkyl that carbon number is 1～4, carbon number are 1～4, amino, nitro, halogen,
Hydroxyl, carboxyl, sulfonic group, sulfoamido, Y represents the alkylidene ,-CO selecting free carbon number to be 1～32-、
-SO2-and-SO2NH(CH2) c-composition group in bivalence crosslinked group, wherein, c represents 0～4, and Z represents sulfonic acid
Base, carboxyl or the phthalimide-based with or without substituent group, the piperazine with or without substituent group
Piperazine base, piperidyl with or without substituent group, wherein, described substituent group be hydrogen atom, carbon number be 1～
The alkyl of 4, carbon number are alkoxyl, substituted-amino, nitro, halogen or the sulfonic group of 1～4, a and b is
Meansigma methods, a, b are respectively less than more than 0 12, and a Yu b sum is less than more than 0 12, and wherein, b is not
0。
2. porphyrazine pigment as claimed in claim 1, wherein, ring A, B, the C in formula (1) is respectively formula (2)
Or formula (8).
3. porphyrazine pigment as claimed in claim 1, wherein, the M in formula (1) is VO or Cu.
4. porphyrazine pigment as claimed in claim 3, wherein, in formula (1), Y be carbon number be 1～3
Alkylidene, Z is the phthalimide-based with or without substituent group or with or without substituent group
Piperazinyl.
5. porphyrazine pigment as claimed in claim 1, wherein, the M in formula (1) is VO.
6. a pigment dispersion compositions, it is characterised in that it is by the Thallus Porphyrae according to any one of Claims 1 to 5
Piperazine pigment dispersion is in disperse medium.
7. pigment dispersion compositions as claimed in claim 6, it is characterised in that disperse medium is that acrylic acid series glues
Polymeric composition.
8. a sheet, it is formed by the pigment dispersion compositions described in coating claim 7.
9. pigment dispersion compositions as claimed in claim 7, it is characterised in that containing heat ray shielding metal
Microgranule.
10. pigment dispersion compositions as claimed in claim 9, wherein, described heat ray shielding metal particle
For any one in stannum oxide, Indium sesquioxide. or zinc oxide.
11. 1 kinds of sheets, it is formed by the pigment dispersion compositions described in coating claim 10.
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| PCT/JP2013/066031 WO2013191029A1 (en) | 2012-06-18 | 2013-06-11 | Porphyrazine dye, and application therefor |
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| JP7205670B2 (en) * | 2020-08-27 | 2023-01-17 | Dic株式会社 | Phthalocyanine composition |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4061654A (en) * | 1971-07-02 | 1977-12-06 | Polaroid Corporation | Novel tetrazaporphins |
| CN101248142A (en) * | 2005-07-05 | 2008-08-20 | 西尔弗布鲁克研究有限公司 | Red-shifted water-dispersible naphthalocyanine dyes |
Family Cites Families (13)
| 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. |
| JPS63139789A (en) * | 1986-12-02 | 1988-06-11 | Mitsui Toatsu Chem Inc | Optical recording medium |
| 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 |
| CN100415715C (en) * | 2003-02-11 | 2008-09-03 | 杜锡光 | Super-phthalocyanine compound with six isoindole structure subunits in laver oxazine cycle and its synthesis and use |
| 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 |
| US20070272918A1 (en) * | 2006-05-25 | 2007-11-29 | Barry Rand | Organic photosensitive devices using subphthalocyanine compounds |
| 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 |
| 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 |
| 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 CN CN201380031619.2A patent/CN104395409B/en not_active Expired - Fee Related
- 2013-06-11 WO PCT/JP2013/066031 patent/WO2013191029A1/en active Application Filing
- 2013-06-11 CN CN201610004096.8A patent/CN105733293B/en not_active Expired - Fee Related
- 2013-06-11 KR KR20147031501A patent/KR20150023250A/en not_active Application Discontinuation
- 2013-06-11 JP JP2014521335A patent/JP6181053B2/en active Active
- 2013-06-17 TW TW102121427A patent/TWI601791B/en not_active IP Right Cessation
-
2016
- 2016-09-09 HK HK16110731.5A patent/HK1222407A1/en not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4061654A (en) * | 1971-07-02 | 1977-12-06 | Polaroid Corporation | Novel tetrazaporphins |
| CN101248142A (en) * | 2005-07-05 | 2008-08-20 | 西尔弗布鲁克研究有限公司 | Red-shifted water-dispersible naphthalocyanine dyes |
Non-Patent Citations (3)
| Title |
|---|
| "5,9,14,18,23,27,32,36-八丁氧基-2,3-萘酞菁Sn的合成及光谱特性的研究";黄权真;《中国优秀博硕士学位论文全文数据库(硕士)工程科技Ⅰ辑》;中国学术期刊（光盘版）电子杂志社;20041215;B014-571 * |
| "Phthalonaphthalocyanines:New Far-Red Dyes for Spectral Hole Burning";Indrek Renge et al.;《J.Phys.Chem.A》;19971231;第101卷(第35期);6202-6213 * |
| "近红外激光防护染料";杨小兵 等;《有机化学》;20021231;第22卷(第1期);33-41 * |
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 |
| CN105733293B (en) | 2017-06-27 |
| TWI601791B (en) | 2017-10-11 |
| CN105733293A (en) | 2016-07-06 |
| JP6181053B2 (en) | 2017-08-16 |
| HK1222407A1 (en) | 2017-06-30 |
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