DE60207631T2 - Tintenstrahltinten - Google Patents
Tintenstrahltinten Download PDFInfo
- Publication number
- DE60207631T2 DE60207631T2 DE60207631T DE60207631T DE60207631T2 DE 60207631 T2 DE60207631 T2 DE 60207631T2 DE 60207631 T DE60207631 T DE 60207631T DE 60207631 T DE60207631 T DE 60207631T DE 60207631 T2 DE60207631 T2 DE 60207631T2
- Authority
- DE
- Germany
- Prior art keywords
- pigment
- ink
- phenyl
- alcohol
- salt
- 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.)
- Expired - Lifetime
Links
- 239000000976 ink Substances 0.000 title description 20
- 239000000049 pigment Substances 0.000 claims description 85
- -1 alkenyl phenol Chemical compound 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 19
- 125000000524 functional group Chemical group 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 238000006467 substitution reaction Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 11
- 239000011734 sodium Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 150000002433 hydrophilic molecules Chemical class 0.000 claims description 9
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 8
- 150000005215 alkyl ethers Chemical class 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000129 anionic group Chemical group 0.000 claims description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 6
- 239000003086 colorant Substances 0.000 claims description 6
- 238000006845 Michael addition reaction Methods 0.000 claims description 5
- 150000003869 acetamides Chemical class 0.000 claims description 5
- 150000003948 formamides Chemical class 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000002091 cationic group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 229920001451 polypropylene glycol Polymers 0.000 claims description 4
- 150000003457 sulfones Chemical class 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
- 239000000010 aprotic solvent Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000006184 cosolvent Substances 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- HOJIHIFXRHMKLL-UHFFFAOYSA-N 1-chloroethanamine Chemical compound CC(N)Cl HOJIHIFXRHMKLL-UHFFFAOYSA-N 0.000 claims description 2
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 claims description 2
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 2
- SOFRHZUTPGJWAM-UHFFFAOYSA-N 3-hydroxy-4-[(2-methoxy-5-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound COc1ccc(cc1N=Nc1c(O)c(cc2ccccc12)C(=O)Nc1cccc(c1)[N+]([O-])=O)[N+]([O-])=O SOFRHZUTPGJWAM-UHFFFAOYSA-N 0.000 claims description 2
- YUXBNNVWBUTOQZ-UHFFFAOYSA-N 4-phenyltriazine Chemical compound C1=CC=CC=C1C1=CC=NN=N1 YUXBNNVWBUTOQZ-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000003139 biocide Substances 0.000 claims description 2
- 239000006172 buffering agent Substances 0.000 claims description 2
- 150000002009 diols Chemical class 0.000 claims description 2
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 claims description 2
- UJTPZISIAWDGFF-UHFFFAOYSA-N ethenylsulfonylbenzene Chemical compound C=CS(=O)(=O)C1=CC=CC=C1 UJTPZISIAWDGFF-UHFFFAOYSA-N 0.000 claims description 2
- 230000000873 masking effect Effects 0.000 claims description 2
- KTDILAZSFSAPMD-UHFFFAOYSA-N n-(2-chloroethyl)aniline Chemical compound ClCCNC1=CC=CC=C1 KTDILAZSFSAPMD-UHFFFAOYSA-N 0.000 claims description 2
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 claims description 2
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 claims description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- PSBDWGZCVUAZQS-UHFFFAOYSA-N (dimethylsulfonio)acetate Polymers C[S+](C)CC([O-])=O PSBDWGZCVUAZQS-UHFFFAOYSA-N 0.000 claims 1
- DXTIXAMVHSAHEW-UHFFFAOYSA-N 2,2-dichloroethylsulfonylbenzene Chemical compound ClC(Cl)CS(=O)(=O)C1=CC=CC=C1 DXTIXAMVHSAHEW-UHFFFAOYSA-N 0.000 claims 1
- NUJGORANFDSMOL-UHFFFAOYSA-N 2-chloroethylsulfonylbenzene Chemical compound ClCCS(=O)(=O)C1=CC=CC=C1 NUJGORANFDSMOL-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- RETQWNSVAOCBQW-UHFFFAOYSA-N ClCC1(C(C=CC=C1)S(=O)(=O)C1C(C=CC=C1)(CCl)CCl)CCl Chemical compound ClCC1(C(C=CC=C1)S(=O)(=O)C1C(C=CC=C1)(CCl)CCl)CCl RETQWNSVAOCBQW-UHFFFAOYSA-N 0.000 claims 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Polymers C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- NXAIQSVCXQZNRY-UHFFFAOYSA-N chloromethylsulfonylbenzene Chemical compound ClCS(=O)(=O)C1=CC=CC=C1 NXAIQSVCXQZNRY-UHFFFAOYSA-N 0.000 claims 1
- 229920013750 conditioning polymer Polymers 0.000 claims 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Polymers C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims 1
- HQVFKSDWNYVAQD-UHFFFAOYSA-N n-hydroxyprop-2-enamide Chemical compound ONC(=O)C=C HQVFKSDWNYVAQD-UHFFFAOYSA-N 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 0 C*c(cc1)cc(OC)*1IC=I[C@@](*)(C(C)=O)C(Ic1ccccc1OC)=O Chemical compound C*c(cc1)cc(OC)*1IC=I[C@@](*)(C(C)=O)C(Ic1ccccc1OC)=O 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000003381 solubilizing effect Effects 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910005965 SO 2 Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 125000005395 methacrylic acid group Chemical class 0.000 description 3
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- VBQUDDWATQWCPP-UHFFFAOYSA-N ethylsulfonylbenzene Chemical compound CCS(=O)(=O)C1=CC=CC=C1 VBQUDDWATQWCPP-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 150000007857 hydrazones Chemical class 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 230000007928 solubilization Effects 0.000 description 2
- 238000005063 solubilization Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- PRAMZQXXPOLCIY-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethanesulfonic acid Chemical compound CC(=C)C(=O)OCCS(O)(=O)=O PRAMZQXXPOLCIY-UHFFFAOYSA-N 0.000 description 1
- IAFBRPFISOTXSO-UHFFFAOYSA-N 2-[[2-chloro-4-[3-chloro-4-[[1-(2,4-dimethylanilino)-1,3-dioxobutan-2-yl]diazenyl]phenyl]phenyl]diazenyl]-n-(2,4-dimethylphenyl)-3-oxobutanamide Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)C(C(=O)C)N=NC(C(=C1)Cl)=CC=C1C(C=C1Cl)=CC=C1N=NC(C(C)=O)C(=O)NC1=CC=C(C)C=C1C IAFBRPFISOTXSO-UHFFFAOYSA-N 0.000 description 1
- GDTSJMKGXGJFGQ-UHFFFAOYSA-N 3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound O1B([O-])OB2OB([O-])OB1O2 GDTSJMKGXGJFGQ-UHFFFAOYSA-N 0.000 description 1
- MFKRHJVUCZRDTF-UHFFFAOYSA-N 3-methoxy-3-methylbutan-1-ol Chemical compound COC(C)(C)CCO MFKRHJVUCZRDTF-UHFFFAOYSA-N 0.000 description 1
- OITNBJHJJGMFBN-UHFFFAOYSA-N 4-(chloromethyl)benzoic acid Chemical compound OC(=O)C1=CC=C(CCl)C=C1 OITNBJHJJGMFBN-UHFFFAOYSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- VMBAUQZYJZISFO-UHFFFAOYSA-N Cc(cc1)ccc1S(=O)=O Chemical compound Cc(cc1)ccc1S(=O)=O VMBAUQZYJZISFO-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- RVPJVVYHKBJTPJ-UHFFFAOYSA-N Nc(cc1)ccc1S(CC(Cl)Cl)(=O)=O Chemical compound Nc(cc1)ccc1S(CC(Cl)Cl)(=O)=O RVPJVVYHKBJTPJ-UHFFFAOYSA-N 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 206010034962 Photopsia Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003619 algicide Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-O dipropylazanium Chemical compound CCC[NH2+]CCC WEHWNAOGRSTTBQ-UHFFFAOYSA-O 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- BLCTWBJQROOONQ-UHFFFAOYSA-N ethenyl prop-2-enoate Chemical compound C=COC(=O)C=C BLCTWBJQROOONQ-UHFFFAOYSA-N 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000005597 hydrazone group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- UNBDDZDKBWPHAX-UHFFFAOYSA-N n,n-di(propan-2-yl)formamide Chemical compound CC(C)N(C=O)C(C)C UNBDDZDKBWPHAX-UHFFFAOYSA-N 0.000 description 1
- NZMAJUHVSZBJHL-UHFFFAOYSA-N n,n-dibutylformamide Chemical compound CCCCN(C=O)CCCC NZMAJUHVSZBJHL-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000006179 pH buffering agent Substances 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910000065 phosphene Inorganic materials 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004964 sulfoalkyl group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
- 239000001052 yellow pigment Substances 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
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/08—Treatment with low-molecular-weight non-polymer organic compounds
-
- 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
- C09D11/322—Pigment inks
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0004—Coated particulate pigments or dyes
- C09B67/0008—Coated particulate pigments or dyes with organic coatings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/851,659 US6602335B2 (en) | 2001-05-08 | 2001-05-08 | Pigment solubilization via treatment with strong base and substitution |
| US851659 | 2001-05-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60207631D1 DE60207631D1 (de) | 2006-01-05 |
| DE60207631T2 true DE60207631T2 (de) | 2006-07-20 |
Family
ID=25311326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60207631T Expired - Lifetime DE60207631T2 (de) | 2001-05-08 | 2002-05-07 | Tintenstrahltinten |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6602335B2 (https=) |
| EP (1) | EP1256608B1 (https=) |
| JP (1) | JP4593058B2 (https=) |
| KR (1) | KR100812904B1 (https=) |
| DE (1) | DE60207631T2 (https=) |
| TW (1) | TWI230184B (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006503114A (ja) * | 2002-01-07 | 2006-01-26 | キャボット コーポレイション | 改質ピグメント生成物およびそれを含むブラックマトリクス |
| US6786957B2 (en) * | 2002-01-22 | 2004-09-07 | Hewlett-Packard Development Company, L.P. | Aqueous ink-jet inks for printing on commercial offset coated media |
| US7173078B2 (en) | 2002-04-12 | 2007-02-06 | Cabot Corporation | Process for preparing modified pigments |
| CN100575426C (zh) * | 2003-01-17 | 2009-12-30 | 卡伯特公司 | 含水有色颜料分散体的制备方法、及喷墨组合物 |
| US6942724B2 (en) * | 2003-04-16 | 2005-09-13 | Cabot Corporation | Modified organic colorants and dispersions, and methods for their preparation |
| US6936097B2 (en) * | 2003-04-16 | 2005-08-30 | Cabot Corporation | Modified organic colorants and dispersions, and methods for their preparation |
| KR100540660B1 (ko) * | 2003-09-26 | 2006-01-10 | 삼성전자주식회사 | 루이스 산을 이용한 자가분산형 착색제의 제조 방법 및상기 착색제를 포함하는 잉크 조성물 |
| US7163577B2 (en) * | 2004-03-01 | 2007-01-16 | Hewlett-Packard Development Company, L.P. | Black pigmented ink-jet inks with improved frequency response |
| US20050256225A1 (en) * | 2004-05-11 | 2005-11-17 | Viola Michael S | Aqueous inkjet ink compositions comprising comb-branched copolymers |
| EP2099869B1 (en) | 2006-10-31 | 2013-05-01 | Sensient Colors Inc. | Modified pigments and methods for making and using the same |
| BRPI0807439A2 (pt) * | 2007-01-24 | 2014-07-01 | Cabot Corp | Processo de formar pigmentos modificados |
| EP2129731A2 (en) * | 2007-02-27 | 2009-12-09 | Cabot Corporation | Inkjet ink compositions comprising multiple modified pigments |
| US7553358B2 (en) * | 2007-05-01 | 2009-06-30 | Canon Kabushiki Kaisha | Ink jet ink, ink jet recording method, ink cartridge, recording unit and ink jet recording apparatus |
| EP2201072B1 (en) | 2007-08-23 | 2018-11-14 | Sensient Colors LLC | Self-dispersed pigments and methods for making and using the same |
| JP2012523479A (ja) | 2009-04-07 | 2012-10-04 | センシエント カラーズ エルエルシー | 自己分散性粒子並びにその製造方法及び使用方法 |
| JP2015067741A (ja) * | 2013-09-30 | 2015-04-13 | Dic株式会社 | 着色剤及びその製造方法 |
| JP2015113435A (ja) * | 2013-12-13 | 2015-06-22 | Dic株式会社 | 活性エネルギー線硬化型組成物及び活性エネルギー線硬化型インクジェットインク |
| JP2016079241A (ja) * | 2014-10-14 | 2016-05-16 | Dic株式会社 | インクジェットプリンタ用インク |
| KR102484706B1 (ko) * | 2016-05-30 | 2023-01-03 | 경희대학교 산학협력단 | 안료변형 시너지스트, 이를 포함하는 안료 분산액 및 잉크 조성물 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1356254A (en) * | 1970-07-16 | 1974-06-12 | Ciba Geigy Uk Ltd | Pigment compositions |
| US4468255A (en) * | 1983-08-10 | 1984-08-28 | Sun Chemical Corporation | Rheology modifiers for arylide yellow pigment dispersions and pigment dispersions containing same |
| JPS61255964A (ja) * | 1985-05-10 | 1986-11-13 | Toyo Soda Mfg Co Ltd | 有機顔料の製造法 |
| GB9007284D0 (en) * | 1990-03-31 | 1990-05-30 | Ciba Geigy Ag | Production of pigments |
| US5062894A (en) * | 1991-02-12 | 1991-11-05 | Sun Chemical Corporation | Poly (alkylene oxide)-modified diarylide pigment composition |
| GB9112155D0 (en) * | 1991-06-06 | 1991-07-24 | Ciba Geigy Ag | Production of pigments |
| NL9101286A (nl) * | 1991-07-23 | 1993-02-16 | Oce Nederland Bv | Werkwijze voor het verbuigen van woorden, alsmede een data-verwerkings-eenheid voor het uitvoeren van een dergelijke werkwijze. |
| US5246494A (en) * | 1991-07-23 | 1993-09-21 | Engelhard Corporation | Mixed coupled azo pigments |
| JP2879623B2 (ja) * | 1991-07-26 | 1999-04-05 | 富士写真フイルム株式会社 | カラー感光材料 |
| IL116376A (en) | 1994-12-15 | 2001-03-19 | Cabot Corp | Aqueous ink jet ink compositions containing modified carbon products |
| US5571311A (en) | 1994-12-15 | 1996-11-05 | Cabot Corporation | Ink jet ink formulations containing carbon black products |
| US5554739A (en) | 1994-12-15 | 1996-09-10 | Cabot Corporation | Process for preparing carbon materials with diazonium salts and resultant carbon products |
| IL116379A (en) | 1994-12-15 | 2003-12-10 | Cabot Corp | Aqueous inks and coatings containing modified carbon products |
| US5922118A (en) | 1996-06-14 | 1999-07-13 | Cabot Corporation | Modified colored pigments and ink jet inks, inks, and coatings containing modified colored pigments |
| US5837045A (en) * | 1996-06-17 | 1998-11-17 | Cabot Corporation | Colored pigment and aqueous compositions containing same |
| JP3271529B2 (ja) * | 1996-10-07 | 2002-04-02 | 東洋インキ製造株式会社 | 表面処理顔料およびその製造方法 |
| JPH10110114A (ja) * | 1996-10-09 | 1998-04-28 | Toyo Ink Mfg Co Ltd | 表面処理顔料およびその製造方法 |
| JP3271530B2 (ja) * | 1996-10-07 | 2002-04-02 | 東洋インキ製造株式会社 | 表面処理顔料およびその製造方法 |
| US5928419A (en) * | 1996-10-07 | 1999-07-27 | Toyo Ink Manufacturing Co., Ltd. | Surface-treated organic pigment and process for the production thereof |
| JP3141792B2 (ja) * | 1996-10-07 | 2001-03-05 | 東洋インキ製造株式会社 | インクジェット用記録液 |
| EP1066352B2 (en) * | 1998-04-03 | 2008-10-01 | Cabot Corporation | Modified pigments having improved dispersing properties |
| US6150433A (en) * | 1998-07-31 | 2000-11-21 | Hewlett-Packard Company | Ink-jet ink compositions containing modified macromolecular chromophores with covalently attached polymers |
| JP4841712B2 (ja) * | 1998-07-31 | 2011-12-21 | ヒューレット・パッカード・カンパニー | インクジェット印刷のための求核置換反応による巨大分子発色団へのポリマー類の共有結合形付着 |
| CA2246156C (en) * | 1998-08-31 | 2008-07-08 | Sun Chemical Corporation | Energy curable inks incorporating grafted pigments |
| WO2001062862A1 (en) * | 2000-02-23 | 2001-08-30 | Seiko Epson Corporation | Process for producing pigment dispersion, pigment dispersion obtained by the process, and ink-jet recording ink comprising the same |
| JP2002020673A (ja) * | 2000-04-10 | 2002-01-23 | Seiko Epson Corp | 顔料分散液の製造方法、その方法により得られた顔料分散液、その顔料分散液を用いたインクジェット記録用インク、並びに、そのインクを用いた記録方法および記録物 |
| JP2002327144A (ja) * | 2000-06-28 | 2002-11-15 | Seiko Epson Corp | 顔料分散液の製造方法と顔料分散液、及びこれを用いたインクジェット記録用インク |
| US6599356B2 (en) * | 2000-06-28 | 2003-07-29 | Seiko Epson Corporation | Method for manufacturing pigment dispersed liquid, and pigment dispersed liquid, and ink for ink-jet printer recording using said pigment dispersed liquid |
| JP2002275387A (ja) * | 2001-03-21 | 2002-09-25 | Ricoh Co Ltd | 有機顔料及びその製造方法、記録液、記録液カートリッジ、記録装置ならびに記録方法 |
-
2001
- 2001-05-08 US US09/851,659 patent/US6602335B2/en not_active Expired - Fee Related
- 2001-10-31 TW TW090127044A patent/TWI230184B/zh not_active IP Right Cessation
-
2002
- 2002-02-05 KR KR1020020006388A patent/KR100812904B1/ko not_active Expired - Fee Related
- 2002-05-07 EP EP02253169A patent/EP1256608B1/en not_active Expired - Lifetime
- 2002-05-07 DE DE60207631T patent/DE60207631T2/de not_active Expired - Lifetime
- 2002-05-08 JP JP2002133054A patent/JP4593058B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE60207631D1 (de) | 2006-01-05 |
| EP1256608B1 (en) | 2005-11-30 |
| JP2002338843A (ja) | 2002-11-27 |
| EP1256608A3 (en) | 2003-08-27 |
| EP1256608A2 (en) | 2002-11-13 |
| KR20020085783A (ko) | 2002-11-16 |
| TWI230184B (en) | 2005-04-01 |
| JP4593058B2 (ja) | 2010-12-08 |
| US6602335B2 (en) | 2003-08-05 |
| US20020195022A1 (en) | 2002-12-26 |
| KR100812904B1 (ko) | 2008-03-11 |
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| 8327 | Change in the person/name/address of the patent owner |
Owner name: HEWLETT-PACKARD DEVELOPMENT CO., L.P., HOUSTON, TE |
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| 8364 | No opposition during term of opposition |