DE102014216758A1 - Borsubphthalocyaninverbindungen und verfahren zu deren herstellung - Google Patents
Borsubphthalocyaninverbindungen und verfahren zu deren herstellung Download PDFInfo
- Publication number
- DE102014216758A1 DE102014216758A1 DE102014216758.2A DE102014216758A DE102014216758A1 DE 102014216758 A1 DE102014216758 A1 DE 102014216758A1 DE 102014216758 A DE102014216758 A DE 102014216758A DE 102014216758 A1 DE102014216758 A1 DE 102014216758A1
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- Germany
- Prior art keywords
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- substituted
- compound
- cyclic
- oxygen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 52
- 238000000034 method Methods 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract description 33
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 31
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 29
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 28
- 239000001301 oxygen Substances 0.000 claims abstract description 28
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229910052796 boron Inorganic materials 0.000 claims abstract description 24
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical group OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 claims abstract description 23
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 18
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 16
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims abstract description 11
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 claims abstract description 11
- 239000011593 sulfur Substances 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 125000000524 functional group Chemical group 0.000 claims abstract description 10
- 125000005647 linker group Chemical group 0.000 claims abstract description 10
- 230000003381 solubilizing effect Effects 0.000 claims abstract description 10
- 235000019445 benzyl alcohol Nutrition 0.000 claims abstract description 9
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 6
- 125000003277 amino group Chemical group 0.000 claims abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
- 125000000468 ketone group Chemical group 0.000 claims abstract description 5
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims abstract description 5
- 125000003158 alcohol group Chemical group 0.000 claims abstract description 4
- 230000002093 peripheral effect Effects 0.000 claims abstract description 4
- -1 diarylketone groups Chemical group 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- PMJMHCXAGMRGBZ-UHFFFAOYSA-N subphthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(=N3)N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C3=N1 PMJMHCXAGMRGBZ-UHFFFAOYSA-N 0.000 claims description 26
- 239000003086 colorant Substances 0.000 claims description 17
- 229920006391 phthalonitrile polymer Polymers 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 11
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 150000001923 cyclic compounds Chemical class 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical class N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 claims description 8
- 150000003938 benzyl alcohols Chemical class 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- YBENZHIOYHEHOD-UHFFFAOYSA-N C(CCCCCCCCCCCCCC)C=1C=C(O[B]OC2=C(C(=C(C=C2)CCCCCCCCCCCCCCC)CCCCCCCCCCCCCCC)CCCCCCCCCCCCCCC)C=CC=1 Chemical compound C(CCCCCCCCCCCCCC)C=1C=C(O[B]OC2=C(C(=C(C=C2)CCCCCCCCCCCCCCC)CCCCCCCCCCCCCCC)CCCCCCCCCCCCCCC)C=CC=1 YBENZHIOYHEHOD-UHFFFAOYSA-N 0.000 claims description 3
- KINAEAYQVYKPFK-UHFFFAOYSA-N Cl[B]OC1=C(C(=C(C=C1)CCCCCCCCCCCCCCC)CCCCCCCCCCCCCCC)CCCCCCCCCCCCCCC Chemical compound Cl[B]OC1=C(C(=C(C=C1)CCCCCCCCCCCCCCC)CCCCCCCCCCCCCCC)CCCCCCCCCCCCCCC KINAEAYQVYKPFK-UHFFFAOYSA-N 0.000 claims description 3
- ILTNWYRKXVWHJK-UHFFFAOYSA-N O(C1=CC=CC=C1)[B]OC1=C(C(=C(C=C1)CCCCCCCCCCCCCCC)CCCCCCCCCCCCCCC)CCCCCCCCCCCCCCC Chemical compound O(C1=CC=CC=C1)[B]OC1=C(C(=C(C=C1)CCCCCCCCCCCCCCC)CCCCCCCCCCCCCCC)CCCCCCCCCCCCCCC ILTNWYRKXVWHJK-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000000472 sulfonyl group Chemical class *S(*)(=O)=O 0.000 claims description 3
- 125000004104 aryloxy group Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000000976 ink Substances 0.000 description 32
- 239000000975 dye Substances 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 25
- 239000000543 intermediate Substances 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
- 238000007639 printing Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 8
- 230000008859 change Effects 0.000 description 7
- 239000012943 hotmelt Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- 150000003738 xylenes Chemical class 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 239000003381 stabilizer Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
- 239000004809 Teflon Substances 0.000 description 4
- 229920006362 Teflon® Polymers 0.000 description 4
- 241000364021 Tulsa Species 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 4
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical group ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HNURKXXMYARGAY-UHFFFAOYSA-N 2,6-Di-tert-butyl-4-hydroxymethylphenol Chemical compound CC(C)(C)C1=CC(CO)=CC(C(C)(C)C)=C1O HNURKXXMYARGAY-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- KBAYQFWFCOOCIC-GNVSMLMZSA-N [(1s,4ar,4bs,7s,8ar,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methanol Chemical compound OC[C@@]1(C)CCC[C@]2(C)[C@H]3CC[C@H](C(C)C)C[C@H]3CC[C@H]21 KBAYQFWFCOOCIC-GNVSMLMZSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000003760 magnetic stirring Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 2
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- JCJNNHDZTLRSGN-UHFFFAOYSA-N anthracen-9-ylmethanol Chemical compound C1=CC=C2C(CO)=C(C=CC=C3)C3=CC2=C1 JCJNNHDZTLRSGN-UHFFFAOYSA-N 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- HNLQCQVRTQXWDX-UHFFFAOYSA-N (1,5-dihydroxycyclohexa-2,4-dien-1-yl)-phenylmethanone Chemical group C1C(O)=CC=CC1(O)C(=O)C1=CC=CC=C1 HNLQCQVRTQXWDX-UHFFFAOYSA-N 0.000 description 1
- BUHVIAUBTBOHAG-FOYDDCNASA-N (2r,3r,4s,5r)-2-[6-[[2-(3,5-dimethoxyphenyl)-2-(2-methylphenyl)ethyl]amino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound COC1=CC(OC)=CC(C(CNC=2C=3N=CN(C=3N=CN=2)[C@H]2[C@@H]([C@H](O)[C@@H](CO)O2)O)C=2C(=CC=CC=2)C)=C1 BUHVIAUBTBOHAG-FOYDDCNASA-N 0.000 description 1
- DDMLBNHFGUXVJE-UHFFFAOYSA-N 1-octadecylsulfonyloctadecane Chemical group CCCCCCCCCCCCCCCCCCS(=O)(=O)CCCCCCCCCCCCCCCCCC DDMLBNHFGUXVJE-UHFFFAOYSA-N 0.000 description 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical class CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
- XBGNOMBPRQVJSR-UHFFFAOYSA-N 2-(4-nitrophenyl)butanoic acid Chemical compound CCC(C(O)=O)C1=CC=C([N+]([O-])=O)C=C1 XBGNOMBPRQVJSR-UHFFFAOYSA-N 0.000 description 1
- PTFIPECGHSYQNR-UHFFFAOYSA-N 3-Pentadecylphenol Chemical group CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 description 1
- FZOOWKMUZYQMLC-UHFFFAOYSA-N 4-(3-pentadecylphenoxy)benzene-1,2-dicarbonitrile Chemical group CCCCCCCCCCCCCCCC1=CC=CC(OC=2C=C(C(C#N)=CC=2)C#N)=C1 FZOOWKMUZYQMLC-UHFFFAOYSA-N 0.000 description 1
- VMRIVYANZGSGRV-UHFFFAOYSA-N 4-phenyl-2h-triazin-5-one Chemical group OC1=CN=NN=C1C1=CC=CC=C1 VMRIVYANZGSGRV-UHFFFAOYSA-N 0.000 description 1
- AMOKUAKXKXBFIW-WJDWOHSUSA-N 9-[(z)-non-3-enyl]-10-octylnonadecanedioic acid Chemical compound OC(=O)CCCCCCCCC(CCCCCCCC)C(CCCCCCCC(O)=O)CC\C=C/CCCCC AMOKUAKXKXBFIW-WJDWOHSUSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- VKIJLPGGTAKJMP-UHFFFAOYSA-N O(S(=O)(=O)O)[S] Chemical compound O(S(=O)(=O)O)[S] VKIJLPGGTAKJMP-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- HLJDOURGTRAFHE-UHFFFAOYSA-N isocyanic acid;3,5,5-trimethylcyclohex-2-en-1-one Chemical compound N=C=O.N=C=O.CC1=CC(=O)CC(C)(C)C1 HLJDOURGTRAFHE-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- DJWFNQUDPJTSAD-UHFFFAOYSA-N n-octadecyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCCNC(=O)CCCCCCCCCCCCCCCCC DJWFNQUDPJTSAD-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000001022 rhodamine dye Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000101 thioether group Chemical group 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
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/30—Metal-free phthalocyanines
-
- 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
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
- C09B47/0675—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having oxygen or sulfur linked directly to the skeleton
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/12—Printing inks based on waxes or bitumen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/34—Hot-melt inks
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14/012,222 US8981088B1 (en) | 2013-08-28 | 2013-08-28 | Boron subphthalocyanine compounds and method of making |
| US14/012,222 | 2013-08-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102014216758A1 true DE102014216758A1 (de) | 2015-03-05 |
Family
ID=52470699
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102014216758.2A Ceased DE102014216758A1 (de) | 2013-08-28 | 2014-08-22 | Borsubphthalocyaninverbindungen und verfahren zu deren herstellung |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8981088B1 (https=) |
| JP (1) | JP6351435B6 (https=) |
| KR (1) | KR102115625B1 (https=) |
| CA (1) | CA2860565C (https=) |
| DE (1) | DE102014216758A1 (https=) |
| IN (1) | IN2014DE02298A (https=) |
| RU (1) | RU2650918C2 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9394319B2 (en) * | 2013-08-28 | 2016-07-19 | Xerox Corporation | Boron subphthalocyanine compounds and method of making |
| US8920551B1 (en) * | 2013-08-28 | 2014-12-30 | Xerox Corporation | Phase change inks |
| WO2016099667A1 (en) | 2014-12-15 | 2016-06-23 | The Government Of The United States Of America, As Represented By The Secretary Of The Navy | Controlling crosslinking density and processing parameters of phthalonitriles |
| US9394404B2 (en) | 2014-12-16 | 2016-07-19 | The United States Of America, As Represented By The Secretary Of The Navy | Synthesis and polymerization of oligomeric aliphatic-aromatic based phthalonitriles |
| CN108690060B (zh) * | 2018-05-24 | 2020-07-07 | 烟台显华光电材料研究院有限公司 | 一类用作电致发光材料的多芳香环化合物及其发光装置 |
| CN108586508B (zh) * | 2018-06-26 | 2020-06-30 | 烟台显华光电材料研究院有限公司 | 一类用作电致发光材料的多芳香环化合物及其发光装置 |
| CN108912151B (zh) * | 2018-06-26 | 2020-07-07 | 烟台显华光电材料研究院有限公司 | 一类用作电致发光材料的多芳香环化合物及其发光装置 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4490731A (en) | 1982-11-22 | 1984-12-25 | Hewlett-Packard Company | Ink dispenser with "frozen" solid ink |
| US5782966A (en) | 1996-06-28 | 1998-07-21 | Tektronix, Inc. | Isocyanate-derived materials for use in phase change ink jet inks |
| US6174937B1 (en) | 1999-07-16 | 2001-01-16 | Xerox Corporation | Composition of matter, a phase change ink, and a method of reducing a coefficient of friction of a phase change ink formulation |
| US6309453B1 (en) | 1999-09-20 | 2001-10-30 | Xerox Corporation | Colorless compounds, solid inks, and printing methods |
| US6472523B1 (en) | 2002-02-08 | 2002-10-29 | Xerox Corporation | Phthalocyanine compositions |
| US6998493B2 (en) | 2003-06-26 | 2006-02-14 | Xerox Corporation | Colorant compounds |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9307749D0 (en) * | 1993-04-15 | 1993-06-02 | Zeneca Ltd | Chemical compounds |
| US6368395B1 (en) * | 1999-05-24 | 2002-04-09 | Kimberly-Clark Worldwide, Inc. | Subphthalocyanine colorants, ink compositions, and method of making the same |
| WO2002028660A2 (en) | 2000-10-02 | 2002-04-11 | Kimberly-Clark Worldwide, Inc. | Nanoparticle based inks and methods of making the same |
| TW569201B (en) * | 2001-03-30 | 2004-01-01 | Vivastar Mastering & Materials | Optical recording medium and method for manufacturing it |
| US6476219B1 (en) | 2002-02-08 | 2002-11-05 | Xerox Corporation | Methods for preparing phthalocyanine compositions |
| US7888398B2 (en) * | 2004-07-29 | 2011-02-15 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Pigment |
| JP2007063437A (ja) * | 2005-08-31 | 2007-03-15 | Tdk Corp | 色素、光記録材料、及び光記録媒体。 |
| US8057589B2 (en) | 2006-12-21 | 2011-11-15 | Xerox Corporation | Phase change inks |
| JP2008216589A (ja) * | 2007-03-02 | 2008-09-18 | Orient Chem Ind Ltd | μ−オキソ架橋−ホウ素サブフタロシアニン二量体を含有する光学膜 |
| MX2010005335A (es) * | 2007-11-26 | 2010-05-27 | Basf Se | Proceso de matizado mejorado. |
| JP5584848B2 (ja) * | 2009-08-06 | 2014-09-10 | 国立大学法人 名古屋工業大学 | サブフタロシアニン誘導体及びその製造方法 |
| US9394319B2 (en) * | 2013-08-28 | 2016-07-19 | Xerox Corporation | Boron subphthalocyanine compounds and method of making |
-
2013
- 2013-08-28 US US14/012,222 patent/US8981088B1/en active Active
-
2014
- 2014-08-12 IN IN2298DE2014 patent/IN2014DE02298A/en unknown
- 2014-08-12 JP JP2014164439A patent/JP6351435B6/ja not_active Expired - Fee Related
- 2014-08-18 RU RU2014133805A patent/RU2650918C2/ru active
- 2014-08-19 KR KR1020140107725A patent/KR102115625B1/ko not_active Expired - Fee Related
- 2014-08-22 DE DE102014216758.2A patent/DE102014216758A1/de not_active Ceased
- 2014-08-25 CA CA2860565A patent/CA2860565C/en not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4490731A (en) | 1982-11-22 | 1984-12-25 | Hewlett-Packard Company | Ink dispenser with "frozen" solid ink |
| US5782966A (en) | 1996-06-28 | 1998-07-21 | Tektronix, Inc. | Isocyanate-derived materials for use in phase change ink jet inks |
| US6174937B1 (en) | 1999-07-16 | 2001-01-16 | Xerox Corporation | Composition of matter, a phase change ink, and a method of reducing a coefficient of friction of a phase change ink formulation |
| US6309453B1 (en) | 1999-09-20 | 2001-10-30 | Xerox Corporation | Colorless compounds, solid inks, and printing methods |
| US6472523B1 (en) | 2002-02-08 | 2002-10-29 | Xerox Corporation | Phthalocyanine compositions |
| US6998493B2 (en) | 2003-06-26 | 2006-02-14 | Xerox Corporation | Colorant compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| JP6351435B6 (ja) | 2018-07-25 |
| JP6351435B2 (ja) | 2018-07-04 |
| KR20150026846A (ko) | 2015-03-11 |
| JP2015044989A (ja) | 2015-03-12 |
| RU2014133805A (ru) | 2016-03-10 |
| US20150065713A1 (en) | 2015-03-05 |
| IN2014DE02298A (https=) | 2015-06-19 |
| CA2860565C (en) | 2018-10-16 |
| US8981088B1 (en) | 2015-03-17 |
| KR102115625B1 (ko) | 2020-05-27 |
| CA2860565A1 (en) | 2015-02-28 |
| RU2650918C2 (ru) | 2018-04-18 |
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