DE69705259T2 - Schwarze Farbstoffzusammensetzung mit wenigen Störtönen - Google Patents
Schwarze Farbstoffzusammensetzung mit wenigen StörtönenInfo
- Publication number
- DE69705259T2 DE69705259T2 DE69705259T DE69705259T DE69705259T2 DE 69705259 T2 DE69705259 T2 DE 69705259T2 DE 69705259 T DE69705259 T DE 69705259T DE 69705259 T DE69705259 T DE 69705259T DE 69705259 T2 DE69705259 T2 DE 69705259T2
- Authority
- DE
- Germany
- Prior art keywords
- dye
- composition
- oxyalkene
- poly
- group
- 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
- 239000000203 mixture Substances 0.000 title claims description 88
- 239000000975 dye Substances 0.000 claims description 90
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 239000000987 azo dye Substances 0.000 claims description 16
- 239000001044 red dye Substances 0.000 claims description 16
- 239000001043 yellow dye Substances 0.000 claims description 16
- 239000001045 blue dye Substances 0.000 claims description 14
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 claims description 14
- 229920002635 polyurethane Polymers 0.000 claims description 14
- 239000004814 polyurethane Substances 0.000 claims description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 11
- 229910052721 tungsten Inorganic materials 0.000 claims description 11
- 239000010937 tungsten Substances 0.000 claims description 11
- 150000001336 alkenes Chemical class 0.000 claims description 9
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 9
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 claims description 9
- 238000002835 absorbance Methods 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 7
- 229920005862 polyol Polymers 0.000 claims description 7
- 150000003077 polyols Chemical class 0.000 claims description 7
- 238000010521 absorption reaction Methods 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229920001228 polyisocyanate Polymers 0.000 claims description 6
- 239000005056 polyisocyanate Substances 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 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 5
- 239000001007 phthalocyanine dye Substances 0.000 claims description 5
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 4
- 239000001000 anthraquinone dye Substances 0.000 claims description 4
- 150000004056 anthraquinones Chemical class 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims 2
- 229920005830 Polyurethane Foam Polymers 0.000 description 10
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 10
- 239000011496 polyurethane foam Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000000295 complement effect Effects 0.000 description 6
- 239000006260 foam Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000001429 visible spectrum Methods 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229920005749 polyurethane resin Polymers 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 230000005670 electromagnetic radiation Effects 0.000 description 3
- 239000001048 orange dye Substances 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002952 polymeric resin Substances 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- HUXDTFZDCPYTCF-UHFFFAOYSA-N 1-chloropropane-1,1-diol Chemical group CCC(O)(O)Cl HUXDTFZDCPYTCF-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 101000642823 Solanum tuberosum Granule-bound starch synthase 2, chloroplastic/amyloplastic Proteins 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 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
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- -1 e.g. Polymers 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 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
- 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
- C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/657,022 US5731398A (en) | 1996-05-31 | 1996-05-31 | Black colorant composition exhibiting low flairing |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69705259D1 DE69705259D1 (de) | 2001-07-26 |
| DE69705259T2 true DE69705259T2 (de) | 2002-03-07 |
Family
ID=24635536
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69705259T Expired - Lifetime DE69705259T2 (de) | 1996-05-31 | 1997-05-29 | Schwarze Farbstoffzusammensetzung mit wenigen Störtönen |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US5731398A (https=) |
| EP (1) | EP0810266B1 (https=) |
| JP (1) | JP4172833B2 (https=) |
| DE (1) | DE69705259T2 (https=) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6245135B1 (en) * | 1997-08-22 | 2001-06-12 | Xerox Corporation | Phase change ink composition |
| US5731398A (en) * | 1996-05-31 | 1998-03-24 | Milliken Research Corporation | Black colorant composition exhibiting low flairing |
| JP2000328039A (ja) * | 1999-05-19 | 2000-11-28 | Hayashibara Biochem Lab Inc | 光吸収剤 |
| KR100336617B1 (ko) * | 1999-06-16 | 2002-05-16 | 전진현 | 헤테로환을 갖는 흑색 분산염료 |
| EP1215250B1 (de) * | 2000-12-13 | 2005-02-23 | Tetenal Photowerk GmbH & Co | Ink-Jet-Tinte und deren Verwendung zum Bedrucken transparenter Druckträger |
| US6583308B2 (en) * | 2001-11-03 | 2003-06-24 | Milliken & Company | Short-chain polymeric yellow cyanoester-derivative colorants and articles comprising such colorants |
| US20040192799A1 (en) * | 2003-03-27 | 2004-09-30 | Jusong Xia | High strength black polyurethane foams with lower amounts of black coloring agents required therein |
| US7056958B2 (en) * | 2003-03-27 | 2006-06-06 | Milliken & Company | Methods of production of high-strength black polyurethane foams |
| US7199164B2 (en) * | 2003-03-27 | 2007-04-03 | Milliken & Company | High-strength black polyurethane foams |
| JP4874095B2 (ja) * | 2003-03-27 | 2012-02-08 | ミリケン・アンド・カンパニー | 高強度黒色ポリウレタンフォーム |
| EP1606332B1 (en) | 2003-03-27 | 2016-04-27 | Milliken & Company | High-strength black polyurethane foams |
| US20060054659A1 (en) * | 2004-09-16 | 2006-03-16 | Radford Philip T | Method and apparatus for blending a colorant |
| US20060063861A1 (en) * | 2004-09-17 | 2006-03-23 | Milliken & Company | Method for employing colorants as indicators in polymer blending |
| US7572325B2 (en) * | 2005-11-30 | 2009-08-11 | Xerox Corporation | Ink carriers, phase change inks including same and methods for making same |
| US7758268B2 (en) * | 2005-12-20 | 2010-07-20 | Xerox Corporation | Hand held photochromic marking implement |
| US20080113198A1 (en) * | 2006-11-10 | 2008-05-15 | Jusong Xia | Leather articles and methods for producing the same |
| US7872069B2 (en) * | 2006-03-31 | 2011-01-18 | Milliken & Company | Coated substrates and polymer dispersions suitable for use in making the same |
| US7662461B2 (en) | 2006-03-31 | 2010-02-16 | Milliken & Company | Synthetic leather articles and methods for producing the same |
| US8431648B2 (en) * | 2006-03-31 | 2013-04-30 | Milliken & Company | Coated substrates and polymer dispersions suitable for use in making the same |
| US8141667B2 (en) * | 2008-06-17 | 2012-03-27 | The Board Of Trustees Of The University Of Alabama For And On Behalf Of Its Component Institution, The University Of Alabama | Hybrid dinghy pusher |
| US8846014B2 (en) | 2011-03-31 | 2014-09-30 | Lvmh Recherche | Makeup composition comprising a black colour mixture of pigments |
| FR2973389B1 (fr) * | 2011-03-31 | 2013-04-19 | Lvmh Rech | Melange de couleur noire et compositions le contenant |
| WO2014031923A1 (en) * | 2012-08-23 | 2014-02-27 | Milliken & Company | Coated substrates and methods for producing the same |
| CN109535361B (zh) * | 2018-11-12 | 2021-09-03 | 中山大学 | 一种紫外光辐照力学响应水性聚氨酯及其制备方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4625288B1 (https=) * | 1966-08-03 | 1971-07-21 | ||
| US4284729A (en) * | 1980-03-31 | 1981-08-18 | Milliken Research Corporation | Process for coloring thermosetting resins |
| US4400320A (en) * | 1981-07-13 | 1983-08-23 | Milliken Research Corporation | Alkyleneoxy fugitive tints containing a 2-amino, 6-methoxy benzathiazole group and process for preparing such fugitive tints |
| US4507407A (en) * | 1984-06-25 | 1985-03-26 | Milliken Research Corporation | Process for in situ coloration of thermosetting resins |
| CA1243669A (en) * | 1984-06-25 | 1988-10-25 | Edward W. Kluger | Reactive colorants |
| DE3530339A1 (de) * | 1985-08-24 | 1987-02-26 | Hoechst Ag | Verfahren zum faerben von polyesterfasern feinen titers |
| US4758243A (en) * | 1986-05-27 | 1988-07-19 | Milliken Research Corporation | Process for coloring polyester shaped articles |
| US4761502A (en) * | 1986-09-08 | 1988-08-02 | Milliken Research Corporation | Polyalkyleneoxytrifluoromethylaniline compounds |
| US4751254A (en) * | 1987-01-20 | 1988-06-14 | Milliken Research Corporation | Process for in situ coloration of thermosetting resins |
| US4978362A (en) * | 1988-03-07 | 1990-12-18 | Milliken Research Corporation | Thermoplastic resin composition containing polyalkyleneoxy-substituted azo coloring agents having trifluoromethyl substituents |
| US4846846A (en) * | 1988-06-20 | 1989-07-11 | Milliken Research Corporation | Process for preparing polyurethane resins colored with anthraquinone colorants and products produced thereby |
| EP0359376B1 (en) * | 1988-07-26 | 1994-03-09 | Canon Kabushiki Kaisha | Recording liquid and ink-jet recording process using same |
| DE3844067A1 (de) * | 1988-12-28 | 1990-07-05 | Bayer Ag | Mischungen von dispersionsazofarbstoffen |
| US5290921A (en) * | 1990-01-08 | 1994-03-01 | Milliken Research Corporation | Intermediates and colorants having primary hydroxyl enriched poly (oxyalkylene) moieties and their preparation |
| ATE145232T1 (de) * | 1990-01-08 | 1996-11-15 | Milliken Res Corp | Zwischenprodukte und farbstoffe mit vermehrt primären hydroxylgruppen enthaltenden poly(oxyalkylen)-resten sowie deren herstellung |
| JPH0745636B2 (ja) * | 1991-06-18 | 1995-05-17 | 三菱化成ヘキスト株式会社 | 分散染料混合物 |
| US5731398A (en) * | 1996-05-31 | 1998-03-24 | Milliken Research Corporation | Black colorant composition exhibiting low flairing |
-
1996
- 1996-05-31 US US08/657,022 patent/US5731398A/en not_active Expired - Lifetime
-
1997
- 1997-05-29 EP EP97303629A patent/EP0810266B1/en not_active Expired - Lifetime
- 1997-05-29 DE DE69705259T patent/DE69705259T2/de not_active Expired - Lifetime
- 1997-06-02 JP JP14433697A patent/JP4172833B2/ja not_active Expired - Fee Related
- 1997-08-20 US US08/915,147 patent/US5925150A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP4172833B2 (ja) | 2008-10-29 |
| EP0810266A3 (en) | 1998-12-16 |
| DE69705259D1 (de) | 2001-07-26 |
| JPH1081834A (ja) | 1998-03-31 |
| EP0810266A2 (en) | 1997-12-03 |
| US5925150A (en) | 1999-07-20 |
| US5731398A (en) | 1998-03-24 |
| EP0810266B1 (en) | 2001-06-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |