CN1085232C - 卤化铜酞菁粗颜料向有用的颜料态的转化 - Google Patents
卤化铜酞菁粗颜料向有用的颜料态的转化 Download PDFInfo
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- CN1085232C CN1085232C CN98124676A CN98124676A CN1085232C CN 1085232 C CN1085232 C CN 1085232C CN 98124676 A CN98124676 A CN 98124676A CN 98124676 A CN98124676 A CN 98124676A CN 1085232 C CN1085232 C CN 1085232C
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- Prior art keywords
- alkyl
- copper phthalocyanine
- group
- hydrogen
- independently
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- 239000000049 pigment Substances 0.000 title claims abstract description 39
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical class [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 230000009466 transformation Effects 0.000 title 1
- -1 cyano-substituted copper Chemical class 0.000 claims abstract description 110
- 238000000034 method Methods 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052802 copper Inorganic materials 0.000 claims abstract description 14
- 239000010949 copper Substances 0.000 claims abstract description 14
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 4
- 239000000460 chlorine Substances 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 239000007788 liquid Substances 0.000 claims abstract description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical class ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000005210 alkyl ammonium group Chemical group 0.000 claims abstract description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical group OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 claims description 12
- 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 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000005605 benzo group Chemical group 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052728 basic metal Inorganic materials 0.000 claims description 6
- 150000003818 basic metals Chemical class 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 150000004782 1-naphthols Chemical class 0.000 claims description 3
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 claims description 3
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical class OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 238000005902 aminomethylation reaction Methods 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- RTZZCYNQPHTPPL-UHFFFAOYSA-N 3-nitrophenol Chemical class OC1=CC=CC([N+]([O-])=O)=C1 RTZZCYNQPHTPPL-UHFFFAOYSA-N 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 abstract description 12
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 3
- 150000001340 alkali metals Chemical class 0.000 abstract description 2
- 150000001879 copper Chemical class 0.000 abstract 3
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 229940100198 alkylating agent Drugs 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 abstract 1
- 150000003460 sulfonic acids Chemical class 0.000 abstract 1
- 230000001131 transforming effect Effects 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 description 11
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 239000002585 base Substances 0.000 description 7
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 230000026030 halogenation Effects 0.000 description 4
- 238000005658 halogenation reaction Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000001400 nonyl group Chemical group [H]C([*])([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])[H] 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 2
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical group [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 229910052757 nitrogen Chemical group 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 125000005936 piperidyl group Chemical group 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- WIHIUTUAHOZVLE-UHFFFAOYSA-N 1,3-diethoxypropan-2-ol Chemical compound CCOCC(O)COCC WIHIUTUAHOZVLE-UHFFFAOYSA-N 0.000 description 1
- CYGUXEZVBLMVRV-UHFFFAOYSA-N 1-bromonaphthalene-2-carbaldehyde Chemical compound C1=CC=C2C(Br)=C(C=O)C=CC2=C1 CYGUXEZVBLMVRV-UHFFFAOYSA-N 0.000 description 1
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- ICCYFVWQNFMENX-UHFFFAOYSA-N 2-chloro-6-nitrophenol Chemical class OC1=C(Cl)C=CC=C1[N+]([O-])=O ICCYFVWQNFMENX-UHFFFAOYSA-N 0.000 description 1
- MNOJRWOWILAHAV-YROCTSJKSA-N 3-bromophenol Chemical compound O[14C]1=[14CH][14CH]=[14CH][14C](Br)=[14CH]1 MNOJRWOWILAHAV-YROCTSJKSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- ZQVKTHRQIXSMGY-UHFFFAOYSA-M 4-ethylbenzoate Chemical compound CCC1=CC=C(C([O-])=O)C=C1 ZQVKTHRQIXSMGY-UHFFFAOYSA-M 0.000 description 1
- PIIZYNQECPTVEO-UHFFFAOYSA-N 4-nitro-m-cresol Chemical class CC1=CC(O)=CC=C1[N+]([O-])=O PIIZYNQECPTVEO-UHFFFAOYSA-N 0.000 description 1
- BOFRXDMCQRTGII-UHFFFAOYSA-N 619-08-9 Chemical class OC1=CC=C([N+]([O-])=O)C=C1Cl BOFRXDMCQRTGII-UHFFFAOYSA-N 0.000 description 1
- AWMHRVHGKOFCNI-UHFFFAOYSA-N C(CCCC)OC(C(C)(C)C)OOCCC(C)C Chemical compound C(CCCC)OC(C(C)(C)C)OOCCC(C)C AWMHRVHGKOFCNI-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical group OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- 125000006202 diisopropylaminoethyl group Chemical group [H]C([H])([H])C([H])(N(C([H])([H])C([H])([H])*)C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([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])C([H])([H])[H] 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
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- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0017—Influencing the physical properties by treatment with an acid, H2SO4
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
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Abstract
一种用于将氯含量为4-50.3重量%的卤化铜酞菁粗颜料转化成有用的颜料态的方法，它包括：在铜酞菁衍生物的存在下，如果需要在水的存在下，用液态酸性芳族有机介质于升高的温度下处理粗颜料，所述铜酞菁衍生物选自铜酞菁-磺酸和-羧酸及其碱金属、铵和烷基铵盐，氨基取代的和氨甲基化的铜酞菁及其与烷基化试剂、磺酸、磺酰氯和碳酰氯的反应产物，亚氨亚甲基-和酰氨亚甲基-取代的铜酞菁，烷基-、芳基-和氰基-取代的铜酞菁，以及羟基-和烷氧基-取代的铜酞菁。
Description
本发明涉及一种用于将氯含量为4-50.3重量％的卤化铜酞菁粗颜料转化成有用的颜料态的新方法。
通常，铜酞菁的卤化产生无定形至微结晶的产物，这种产物由于其显著的聚集倾向而在颜料应用中没有实用性。
已知有各种方法将粗颜料转化成有用的颜料态，例如机械粉碎、或用浓硫酸或在升高的温度下用有机溶剂进行处理。
用于处理多卤化铜酞菁的溶剂主要是，在水的存在或不存在下的二甲苯(DE-A-20 13 818)、三氯苯、氯萘或硝基苯(DE-A-24 49 231)、2-硝基苯酚(DE-A-12 42 180)、萘酚(GB-A-1 088 736)、苯甲酸和/或烷基苯甲酸(EP-A-58 888)或脂肪酮(DE-A-36 36 428)。JP-A336556/1994描述了一种方法，其中：在铜酞菁衍生物的存在下，于水和芳族溶剂的混合物中加热多卤化铜酞菁；没有使用酸性溶剂。
这些已知方法往往不仅产生不令人满意的结果，甚至局限于具有高卤化度(氯含量≥38.5重量％，即在CuPc结构上有至少10个氯原子)的铜酞菁。
本发明的一个目的是提供一种方法，这样不仅多卤化的，而且特别是初步卤化(例如，氯含量＜38.5重量％)的铜酞菁能够以一种技术上简单的实用方式转化成色彩上有价值的颜料态，这使得为特殊应用制备优化颜料成为可能。
我们发现，该目的可通过一种用于将氯含量为4-50.3重量％的卤化铜酞菁粗颜料转化成有用的颜料态的方法而实现，该方法包括：在铜酞菁衍生物的存在下，如果需要在水的存在下，用液态酸性芳族有机介质于升高的温度下处理粗颜料，所述铜酞菁衍生物选自铜酞菁-磺酸和-羧酸及其碱金属、铵和烷基铵盐，氨基取代的和氨甲基化的铜酞菁及其与烷基化试剂、磺酸、磺酰氯和碳酰氯的反应产物，亚氨亚甲基-和酰氨亚甲基-取代的铜酞菁，烷基-、芳基-和氰基-取代的铜酞菁，以及羟基-和烷氧基-取代的铜酞菁。
所用的有机介质优选地为一种具有通式I的化合物：
其中X为羟基或羧基，且苯环D可另外具有最多两个相同的或不同的取代基并可被苯并稠化，所述取代基选自硝基、C1-C4烷基(优选地为C1-C2烷基)、C2-C4链烯基(优选地为C2-C3链烯基)、氯和溴。
当X为羧基(基于苯甲酸的“溶剂”)时，苯环D优选地被其它的C1-C4烷基(尤其是C1-C2烷基)基团取代、或特别优选地不被取代。
当X为羟基(酚类“溶剂”)时，苯环D优选地另外具有前述取代基中的一个；如果苯环D被苯并稠化，它优选地不再具有取代基。
有机介质应该在室温下具有很小(如果有的话)的水溶解度，并应该在处理温度下为液态。因此，所述化合物I的熔点一般应该为≤200℃，优选地≤150℃。
合适的酸性芳族有机介质的例子为：苯甲酸、2-、3-和4-甲基苯甲酸、2-、3-和4-乙基苯甲酸、苯酚、2-、3-和4-硝基苯酚、2-、3-和4-甲基苯酚(-甲苯酚)、2-、3-和4-乙基苯酚、2-烯丙基苯酚、2-、3-和4-溴苯酚、2，4-二溴苯酚、2，4-二氯苯酚、2-氯-6-硝基苯酚、2-氯-4-硝基苯酚、2，4-二硝基苯酚、3-甲基-4-硝基苯酚、1-和2-萘酚、和1-溴-2-萘酚、及其混合物，其中：3-和4-硝基苯酚、以及1-和2-萘酚是优选的，而2-硝基苯酚是特别优选的。
每克铜酞菁粗颜料中所用有机介质的量一般在1-20克的范围内，优选地在1-6克的范围内。
本发明的颜料处理在存在或不存在水的情况下都可进行。即，卤化铜酞菁粗颜料能够以干燥形式，或有利地直接以卤化的水湿(水含量通常在50-90重量％的范围内)压缩滤饼形式使用。
本发明的颜料处理过程中的水量并不严格，但应该避免使用过分大量的水，这样就不会没有必要地降低空间-时间效率。
本发明的颜料处理，在一种上述的铜酞菁衍生物，当然包括这些衍生物的混合物的存在下进行。
铜酞菁衍生物既可用于在重结晶过程中控制晶体生长，又可改性所得颜料的面。它们的选择取决于粗颜料的氯化程度、重结晶颜料所需的性能分布、以及后来的应用介质。
具有通式II
的铜酞菁衍生物是优选的，其中：
A和B相互独立地为以下取代基：
-SO3M、-CO2M、-SO3H·HNR1R2、-CH2NR3R4、-NR3R4、-CH2NR3R4·HO3SR5、-NR3R4·HO3SR5、-NHCOR1、-CH2NHCOR1、-NHSO2R1、-CH2HSO2R1、-SO2NHR1、-CONHR1、C1-C6烷基、芳基、氰基或-OR6，其中
R1和R2相互独立地为氢、或可被-NR7R8取代的C2-C20链烯基或C1-C20烷基，其中R7和R6相互独立地为C1-C20烷基、可包含一个或多个杂原子的C5-C8环烷基、或氢，
R3和R4相互独立地为氢、C1-C20烷基、C2-C20链烯基或芳基，或与氮原子结合形成可选择性地包含其它杂原子或羰基或磺酰基基团并可被苯并稠化的5-或6-元环，
R5为对-(C10-C20烷基)苯基或C2-C20链烯基，
R6为氢或C1-C6烷基，且
M为氢或碱金属，
m为＞0至4.0的整数或小数，
n为0-4.0的整数或小数。
其中变量具有以下含义的结构式II的铜酞菁衍生物是特别优选的：
A和B相互独立地为以下取代基：
-SO3M、-SO3H·HNR1R2、-CH2NR3R4、-CH2NR3R4·HO3SR5或-SO2NHR1，其中
R1和R2相互独立地为C1-C20烷基或氢，
R3和R4相互独立地为C1-C6烷基或氢，或与氮原子结合形成含羰基或磺酰基的苯并稠化5-元环，
R5为对-(C10-C20烷基)苯基，且
M为氢或碱金属，
m为＞0至4的整数或小数，
n为0-4的整数或小数，前提是m+n的总和为0.1-4，尤其是1.0-3.5。
结构式II中的基团A和B，及其取代基的具体例子为：
直链或支链C1-C20烷基基团如甲基、乙基、丙基、异丙基、丁基、异丁基、叔丁基、戊基、异戊基、新戊基、叔戊基、己基、2-甲基戊基、庚基、1-乙基戊基、辛基、2-乙基己基、异辛基、壬基、异壬基、葵基、异葵基、十一烷基、十二烷基、十三烷基、异十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、十九烷基和二十烷基(异辛基、异壬基、异葵基和异十三烷基的命名为普通命名，它们衍生自通过氧化法得到的醇-cf.Ullmann’s Encyklopadie dertechnischen Chemie，第4版，第7卷，215-217页，以及第11卷，435-436页)；
直链或支链C2-C20链烯基基团如乙烯基、丙烯基、异丙烯基、丁烯基、异丁烯基、戊烯基、己烯基、庚烯基、辛烯基、壬烯基、葵烯基、十一链烯基、十二链烯基、十三链烯基、十四链烯基、十五链烯基、十六链烯基、十七链烯基、十八链烯基、十九链烯基和二十链烯基；
直链或支链C1-C6烷氧基基团如甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、异丁氧基、叔丁氧基、戊氧基、异戊氧基、新戊氧基、叔戊氧基和己氧基；
可包含杂原子如氧和/或氮以取代一个或多个碳原子，但不通过这些杂原子连接的C5-C8环烷基基团，如环戊基、环己基、环庚基、环辛基、四氢呋喃基、吡咯烷基、哌啶基、哌嗪基和吗啉基；
芳基基团如萘基，特别是苯基；
对-(C10-C20烷基)苯基基团如对-葵基-、对-十一烷基-，特别是对-十二烷基-，还有对-十三烷基-、对-十四烷基-、对-十五烷基-、对-十六烷基-、对-十七烷基-、对-十八烷基-、对-十九烷基-和对-二十烷基-苯基；
羧基，优选地为磺基和单(C10-C20烷基)磺酸铵基团如单葵基-、单十一烷基-、单十二烷基-、单十三烷基-、单十四烷基-、单十五烷基-，尤其是单十六烷基-，还有单十七烷基-、单十八烷基-、单十九烷基-和单二十烷基-磺酸铵基团；
单-和二(C1-C6烷基)氨基基团如单-和二甲氨基、单-和尤其是二乙氨基、单-和二丙氨基、单-和二异丙氨基、单-和二丁氨基、单-和二异丁氨基、单-和二戊氨基以及单-和二己氨基，另外尤其是，单-和优选地为二(C1-C6烷基)氨基甲基基团，其中所述氨基基团通过一个亚甲基基团连接到酞菁结构上；
单-和二(C1-C6烷基)氨基基团(优选地为相应的氨甲基基团)与C10-C20烷基苯磺酸如对-葵基-、对-十一烷基-，特别是对-十二烷基-，还有对-十三烷基-、对-十四烷基-、对-十五烷基-、对-十六烷基-、对-十七烷基-、对-十八烷基-、对-十九烷基-和对-二十烷基-苯磺酸的反应产物，其中烷基基团位于苯磺酸基团的邻位、间位或优选地为对位，如-CH2-N(C2H5)2·HO3S-Ph-4-C12H25和-CH2-NH(C2H5)·HO3S-Ph-4-C12H25；
包含胺氮原子并通过其连接的杂环烷基和杂芳基如4-吗啉基、吡咯烷基、哌啶基、哌嗪基、吡唑基、吡咯基、吡嗪基、咪唑基、尤其是N-苯二甲酰亚氨基和N-邻磺酰苯甲酰亚氨基，以及优选地为通过-CH2-连接到酞菁结构上的相应基团；
单(C1-C20烷基羰基)氨基基团如单甲基-、单乙基-、单丙基-、单异丙基-、单丁基-、单异丁基-、叔单丁基-、单戊基-、单异戊基-、单新戊基-、叔单戊基-、单己基-、2-单甲基戊基-、单庚基-、1-单乙基戊基-、单辛基-、2-单乙基己基-、单异辛基-、单壬基-、单异壬基-、单葵基-、单十一烷基-、单十二烷基-、单十三烷基-、单十四烷基-、单十五烷基-，尤其是单十六烷基-，还有单十七烷基-、单十八烷基-、单十九烷基-和单二十烷基-羰基氨基，以及通过-CH2-连接到酞菁结构上的相应氨基基团；
单(C1-C20烷基磺酰基)氨基基团如单甲基-、单乙基-、单丙基-、单异丙基-、单丁基-、单异丁基-、叔单丁基-、单戊基-、单异戊基-、单新戊基-、叔单戊基-、单己基-、2-单甲基戊基-、单庚基-、1-单乙基戊基-、单辛基-、2-单乙基己基-、单异辛基-、单壬基-、单异壬基-、单葵基-、单十一烷基-、单十二烷基-、单十三烷基-、单十四烷基-、单十五烷基-，尤其是单十六烷基-，还有单十七烷基-、单十八烷基-、单十九烷基-和单二十烷基-磺酰基氨基，以及通过-CH2-连接到酞菁结构上的相应氨基基团；
单(C1-C20烷氨基)磺酰基基团如单甲基-、单乙基-、单丙基-、单异丙基-、单丁基-、单异丁基-、叔单丁基-、单戊基-、单异戊基-、单新戊基-、叔单戊基-、单己基-、2-单甲基戊基-、单庚基-、1-单乙基戊基-、单辛基-、2-单乙基己基-、单异辛基-、单壬基-、单异壬基-、单葵基-、单十一烷基-、单十二烷基-、单十三烷基-、单十四烷基-、单十五烷基-，尤其是单十六烷基-，还有单十七烷基-、单十八烷基-、单十九烷基-和单二十烷基-氨基磺酰基，有可能烷基基团具有一个末端氨基、单-或二(C1-C6烷基)氨基基团；
单(C1-C20烷氨基)羰基基团如单甲基-、单乙基-、单丙基-、单异丙基-、单丁基-、单异丁基-、叔单丁基-、单戊基-、单异戊基-、单新戊基-、叔单戊基-、单己基-、2-单甲基戊基-、单庚基-、1-单乙基戊基-、单辛基-、2-单乙基己基-、单异辛基-、单壬基-、单异壬基-、单葵基-、单十一烷基-、单十二烷基-、单十三烷基-、单十四烷基-、单十五烷基-，尤其是单十六烷基-，还有单十七烷基-、单十八烷基-、单十九烷基-和单二十烷基-氨基羰基，有可能烷基基团具有一个末端氨基、单-或二(C1-C6烷基)氨基基团。
铜酞菁衍生物II本身是己知的，可按照已知方法(如EP-A-535 774、DE-A-25 16 054、EP-A-538 784和DE-A-29 05 114)来制备。
用于本发明方法中的铜酞菁衍生物II的量一般在0.1-20重量％，优选地在1-10重量％的范围内，其中每一百分比都是基于铜酞菁粗颜料的。
合适的反应温度一般在80-200℃，优选也在80-120℃的范围内，其中温度在每种情况下还应该与酸性芳族有机介质的熔点一致。
在水的存在下，本发明的颜料处理优选地在＞100℃的温度和自生压力下，于密闭反应器中进行。
颜料处理通常进行2-10小时，尤其是2-5小时。所选温度越高，重结晶越快。
本发明的方法按照以下方式进行较为有利：
将优选地以水湿滤饼形式存在的卤化铜酞菁粗颜料、铜酞菁衍生物和酸性芳族有机介质的混合物加热至所需温度，然后在该温度下搅拌2-10小时。为了分离颜料，在50-100℃下，加入一定数量的碱水(如，2-60重量％浓度的碱金属氢氧化物溶液)，该数量至少为转化有机介质成其水溶性碱金属盐时的所需当量。随后过滤该颜料，用水洗涤并干燥。
有机介质可通过使用无机酸酸化碱金属盐溶液并在室温下冷却而重新沉淀，然后重新用于颜料处理。
本发明的方法提供了一种得到鲜艳的、透明的且强卤化的(初步卤化和多卤化的)铜酞菁颜料的有利方式，该颜料具有优异的流变性能，适合用于常规的和水成的涂料体系。
实施例
将氯含量为X1重量％的50克(看作100％)卤化铜酞菁且颜料(以水含量为X2重量％的含水压缩饼的形式使用)、2.5克铜酞菁衍生物II’
和100克有机介质III的混合物加热至100℃，然后在该温度下搅拌5小时。
冷却至80℃之后，加入290克的31％浓度的氢氧化钠溶液。过滤该颜料，用水洗涤并在100℃干燥。
涉及这些实验及其结果的更详细内容总结于下表中：
表
| 实施例 | 粗颜料 | CuPc衍生物II | 有机介质III | 处理过的颜料 | ||
| X1重量％的氯 | X2重量％的水 | 产率[g] | 色彩性能 | |||
| 1 | 5.1 | 80.3 | A＝-CH2NH(C2H5)；m＝2 | 2-硝基苯酚 | 52.5 | 比C1更浓、更鲜艳、在质地上更柔软 |
| 2 | 5.1 | 80.3 | A＝-CH2NH(C2H5)·HO3S-Ph-4-C12H25；m＝2 | 2-硝基苯酚 | 52.0 | 比C1更浓、更鲜艳、在质地上更柔软 |
| C1 | 5.1 | 80.3 | - | 2-硝基苯酚 | 48.7 | |
| 3 | 15.6 | 68.0 | A＝-SO3H；m＝1.3 | 2-硝基苯酚 | 52.9 | 比C2更浓、更鲜艳、更透明 |
| 4 | 15.6 | 68.0 | A＝-CH2N-邻苯二甲酰基亚氨基；m＝3 | 2-硝基苯酚 | 51.2 | 比C2更浓、更鲜艳、更透明 |
| C2 | 15.6 | 68.0 | - | 2-硝基苯酚 | 49.2 | |
| 5 | 15.6 | 68.0 | A＝-SO3H；m＝1.3 | 1-萘酚 | 52.1 | 比C3更浓、更鲜艳、更透明 |
| C3 | 15.6 | 68.0 | - | 1-萘酚 | 49.7 | |
| 6 | 38.7 | 80.0 | A＝-SO3H；m＝1.3 | 2-硝基苯酚 | 48.5 | 比C4更浓、更鲜艳 |
| 7 | 38.7 | 80.0 | A＝-CH2NH(C2H5)·HO3S-Ph-4-C12H25；m＝2 | 2-硝基苯酚 | 50.5 | 比C4更浓、更鲜艳 |
| C4 | 38.7 | 80.0 | - | 2-硝基苯酚 | 46.5 | |
Claims (5)
1.一种用于将氯含量为4-50.3重量％的卤化铜酞菁粗颜料转化成有用的颜料态的方法，它包括：在铜酞菁衍生物的存在下，如果需要在水的存在下，用液态酸性芳族有机介质于80-200℃的温度处理粗颜料，所述铜酞菁衍生物选自铜酞菁-磺酸和-羧酸及其碱金属、铵和烷基铵盐，氨基取代的和氨甲基化的铜酞菁及其与烷基化试剂、磺酸、磺酰氯和碳酰氯的反应产物，亚氨亚甲基-和酰氨亚甲基-取代的铜酞菁，烷基-、芳基-和氰基-取代的铜酞菁，以及羟基-和烷氧基-取代的铜酞菁，其中所述的芳族有机介质是一种具有如下通式I的化合物
式中X为羟基或羧基，且苯环D可另外具有最多两个相同的或不同的取代基并可被苯并稠化，所述取代基选自硝基、C1-C4烷基、C2-C4链烯基、氯和溴。
2.根据权利要求1或2所要求的方法，其中有机介质为2-硝基苯酚、3-硝基苯酚、4-硝基苯酚、1-萘酚或2-萘酚。
3.根据权利要求1的方法，其中所用的铜酞菁衍生物具有通式II，
式中：
A和B相互独立地为以下取代基：
-SO3M、-CO2M、-SO3H·HNR1R2、-CH2NR3R4、-NR3R4、-CH2NR3R4·HO3SR5、-NR3R4·HO3SR5、-NHCOR1、-CH2NHCOR1、-NHSO2R1、-CH2NHSO2R1、-SO2NHR1、-CONHR1、C1-C6烷基、芳基、氰基或-OR6，其中
R1和R2相互独立地为氢、或可被-NR7R8取代的C2-C20链烯基或C1-C20烷基，其中R7和R8相互独立地为C1-C20烷基、可包含一个或多个杂原子的C5-C8环烷基、或氢，
R3和R4相互独立地为氢、C1-C20烷基、C2-C20链烯基或芳基，或与氮原子结合形成可选择性地包含其它杂原子或羰基或磺酰基基团并可被苯并稠化的5-或6-元环，
R5为对-(C10-C20烷基)苯基或C2-C20链烯基，
R6为氢或C1-C6烷基，且
M为氢或碱金属，
m为＞0至4.0的整数或小数，
n为0-4.0的整数或小数。
4.根据权利要求1的方法，其中所用的铜酞菁衍生物具有结构式II，该结构式中的变量具有以下含义：
A和B相互独立地为以下取代基：
-SO3M、-SO3H·HNR1R2、-CH2NR3R4、-CH2NR3R4·HO3SR5或-SO2NHR1，其中
R1和R3相互独立地为C1-C20烷基或氢，
R3和R4相互独立地为C1-C6烷基或氢，或与氮原子结合形成含羰基或磺酰基的苯并稠化5-元环，
R5为对-(C10-C20烷基)苯基，
M为氢或碱金属，
m为＞0至4的整数或小数，
n为0-4的整数或小数，前提是m+n的总和为0.1-4。
5.根据权利要求1的方法，其中使用了基于粗颜料的0.1-20重量％的具有结构式II的铜酞菁衍生物。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19745922.6 | 1997-10-17 | ||
| DE19745922A DE19745922A1 (de) | 1997-10-17 | 1997-10-17 | Verfahren zur Überführung von halogenierten Kupferphtalocyanin-Rohpigmenten in eine für die Anwendung geeignete Pigmentform |
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| Publication Number | Publication Date |
|---|---|
| CN1219558A CN1219558A (zh) | 1999-06-16 |
| CN1085232C true CN1085232C (zh) | 2002-05-22 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN98124676A Expired - Fee Related CN1085232C (zh) | 1997-10-17 | 1998-10-17 | 卤化铜酞菁粗颜料向有用的颜料态的转化 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5944887A (zh) |
| EP (1) | EP0909795B1 (zh) |
| JP (1) | JP4427112B2 (zh) |
| KR (1) | KR100544448B1 (zh) |
| CN (1) | CN1085232C (zh) |
| DE (2) | DE19745922A1 (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6132911A (en) * | 1998-07-27 | 2000-10-17 | Ricoh Company, Ltd. | Method for manufacturing pigment, electrophotographic photoconductor using the pigment and electrophotographic image forming method and apparatus using the photoconductor |
| DE10016993A1 (de) | 2000-04-07 | 2001-10-11 | Basf Ag | Anchlorierte Kupferphthalocyaninpigmente |
| DE10257498A1 (de) * | 2002-12-10 | 2004-07-01 | Clariant Gmbh | Verfahren zur Herstellung von Phthalocyaninpigmentzubereitungen |
| KR100694106B1 (ko) * | 2005-04-27 | 2007-03-12 | 삼성전자주식회사 | 착색제 유사 첨가제를 함유한 잉크 조성물, 이를 포함한잉크젯 프린터 카트리지 및 잉크 젯트 기록 장치 |
| JP6410081B2 (ja) * | 2014-07-18 | 2018-10-24 | Dic株式会社 | プラスチック着色用顔料組成物 |
| JP6662912B2 (ja) * | 2015-06-04 | 2020-03-11 | サン ケミカル コーポレイション | 塩素化銅フタロシアニン顔料 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4205995A (en) * | 1976-12-01 | 1980-06-03 | Ciba-Geigy Corporation | Pigment compositions |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2930796A (en) * | 1957-02-11 | 1960-03-29 | Gen Aniline & Film Corp | Conditioning of crude polychloro copper phthalocyanines |
| DE1242180B (de) * | 1964-07-18 | 1967-06-15 | Basf Ag | Verfahren zur Herstellung von farbstarken und kornweichen polyhalogenierten Kupferphthalocyaninen |
| DE1569639C3 (de) * | 1965-08-18 | 1974-08-29 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von farbstarken Polyhalogenkupferphthalocy aninen |
| DE2013818C3 (de) * | 1970-03-23 | 1978-12-14 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung und Isolierung von leicht dispergierbaren Polychlor- und Polybrompolychlorkupferphthalocyaninen |
| DE2449231A1 (de) * | 1974-10-16 | 1976-04-29 | Bayer Ag | Formierung von perhalogen-kupferphthalocyaninen |
| DE2519753C3 (de) * | 1975-05-02 | 1978-06-22 | Basf Ag, 6700 Ludwigshafen | Gegen Rekristallisation und Modifikationsumwandlung stabilisierte Pigmentzubereitungen und deren Verwendung |
| DE2516054C3 (de) * | 1975-04-12 | 1979-05-10 | Basf Ag, 6700 Ludwigshafen | Gegen Rekristallisation und Modifikationsumwandlung stabilisierte Phthalocyaninzubereitungen und deren Verwendung |
| DK140901C (da) * | 1975-04-12 | 1980-05-19 | Basf Ag | Phthalocyaninpigmentpraeparater stabiliseret mod rekrystallisation og modifikationsomdannelse |
| DE2905114C2 (de) * | 1979-02-10 | 1981-03-19 | Basf Ag, 6700 Ludwigshafen | Pigmentzubereitungen |
| EP0058888A3 (de) * | 1981-02-23 | 1982-10-06 | Mobay Chemical Corporation | Konditionierung von Phthalocyaninverbindungen |
| DE3442118A1 (de) * | 1984-11-17 | 1986-05-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von farbstarken polyhalogenkupferphthalocyaninen |
| GB8515600D0 (en) * | 1985-06-20 | 1985-07-24 | Ciba Geigy Ag | Pigmentary copper phthalocyanine |
| DE3636428A1 (de) * | 1986-10-25 | 1988-05-05 | Basf Ag | Verfahren zur herstellung von farbstarken polyhalogenkupferphthalocyaninpigmenten |
| JP3013900B2 (ja) * | 1990-10-22 | 2000-02-28 | 東洋インキ製造株式会社 | 印刷インキ用ポリハロゲン化フタロシアニン、その製造方法およびその用途 |
| JP2836320B2 (ja) * | 1991-10-04 | 1998-12-14 | 東洋インキ製造株式会社 | 塗料組成物 |
| EP0538784B2 (de) * | 1991-10-23 | 2000-12-27 | Clariant GmbH | Pigmentzubereitungen |
| JPH06336556A (ja) * | 1993-05-28 | 1994-12-06 | Toyo Ink Mfg Co Ltd | ポリハロゲン化銅フタロシアニン顔料の製造方法 |
| GB9517565D0 (en) * | 1995-08-26 | 1995-10-25 | Ciba Geigy Ag | Pigment compositions |
| JPH09291223A (ja) * | 1996-04-26 | 1997-11-11 | Toyo Ink Mfg Co Ltd | β型銅フタロシアニン顔料の製造方法 |
| US5759254A (en) * | 1996-07-18 | 1998-06-02 | Ciba Specialty Chemicals Corporation | Substituted phthalocyanines |
-
1997
- 1997-10-17 DE DE19745922A patent/DE19745922A1/de not_active Withdrawn
-
1998
- 1998-10-06 DE DE59801211T patent/DE59801211D1/de not_active Revoked
- 1998-10-06 EP EP98118849A patent/EP0909795B1/de not_active Revoked
- 1998-10-13 US US09/169,988 patent/US5944887A/en not_active Expired - Lifetime
- 1998-10-16 KR KR1019980043288A patent/KR100544448B1/ko not_active IP Right Cessation
- 1998-10-16 JP JP29530798A patent/JP4427112B2/ja not_active Expired - Fee Related
- 1998-10-17 CN CN98124676A patent/CN1085232C/zh not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4205995A (en) * | 1976-12-01 | 1980-06-03 | Ciba-Geigy Corporation | Pigment compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| DE19745922A1 (de) | 1999-04-22 |
| US5944887A (en) | 1999-08-31 |
| EP0909795A1 (de) | 1999-04-21 |
| JPH11189731A (ja) | 1999-07-13 |
| KR100544448B1 (ko) | 2006-03-28 |
| KR19990037151A (ko) | 1999-05-25 |
| CN1219558A (zh) | 1999-06-16 |
| EP0909795B1 (de) | 2001-08-16 |
| JP4427112B2 (ja) | 2010-03-03 |
| DE59801211D1 (de) | 2001-09-20 |
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