GB797850A - Manufacture of lakes of monoazo dyes of the benzene-azo-naphthalene series and theiruse - Google Patents
Manufacture of lakes of monoazo dyes of the benzene-azo-naphthalene series and theiruseInfo
- Publication number
- GB797850A GB797850A GB3187/56A GB318756A GB797850A GB 797850 A GB797850 A GB 797850A GB 3187/56 A GB3187/56 A GB 3187/56A GB 318756 A GB318756 A GB 318756A GB 797850 A GB797850 A GB 797850A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- hydroxy
- lakes
- dyestuff
- prepared
- 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
Links
- 239000000975 dye Substances 0.000 title abstract 13
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title abstract 4
- SOYBJIUDKRLQTA-UHFFFAOYSA-N benzene;dinaphthalen-1-yldiazene Chemical class C1=CC=CC=C1.C1=CC=C2C(N=NC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 SOYBJIUDKRLQTA-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 abstract 7
- 239000002253 acid Substances 0.000 abstract 6
- 229910052788 barium Inorganic materials 0.000 abstract 5
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 abstract 5
- 239000000203 mixture Substances 0.000 abstract 5
- 125000002843 carboxylic acid group Chemical group 0.000 abstract 4
- 239000000839 emulsion Substances 0.000 abstract 4
- 229910052751 metal Inorganic materials 0.000 abstract 4
- 239000002184 metal Substances 0.000 abstract 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 3
- 229910052791 calcium Inorganic materials 0.000 abstract 3
- 239000011575 calcium Substances 0.000 abstract 3
- 230000008878 coupling Effects 0.000 abstract 3
- 238000010168 coupling process Methods 0.000 abstract 3
- 238000005859 coupling reaction Methods 0.000 abstract 3
- 239000003921 oil Substances 0.000 abstract 3
- 235000019198 oils Nutrition 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 239000000344 soap Substances 0.000 abstract 3
- MJNYPLCGWXFYPD-UHFFFAOYSA-N 2-amino-5-sulfobenzoic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1C(O)=O MJNYPLCGWXFYPD-UHFFFAOYSA-N 0.000 abstract 2
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 abstract 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 2
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 abstract 2
- 229910001626 barium chloride Inorganic materials 0.000 abstract 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 229920000915 polyvinyl chloride Polymers 0.000 abstract 2
- 239000004800 polyvinyl chloride Substances 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 235000015112 vegetable and seed oil Nutrition 0.000 abstract 2
- 239000008158 vegetable oil Substances 0.000 abstract 2
- GRGSHONWRKRWGP-UHFFFAOYSA-N 2-amino-4-sulfobenzoic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1C(O)=O GRGSHONWRKRWGP-UHFFFAOYSA-N 0.000 abstract 1
- JFGQHAHJWJBOPD-UHFFFAOYSA-N 3-hydroxy-n-phenylnaphthalene-2-carboxamide Chemical compound OC1=CC2=CC=CC=C2C=C1C(=O)NC1=CC=CC=C1 JFGQHAHJWJBOPD-UHFFFAOYSA-N 0.000 abstract 1
- JGSAMPZLJLDOKW-UHFFFAOYSA-N 5-amino-2-chloro-4-sulfobenzoic acid Chemical compound NC1=CC(C(O)=O)=C(Cl)C=C1S(O)(=O)=O JGSAMPZLJLDOKW-UHFFFAOYSA-N 0.000 abstract 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 abstract 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 abstract 1
- 229910021502 aluminium hydroxide Inorganic materials 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 abstract 1
- 239000001110 calcium chloride Substances 0.000 abstract 1
- 229910001628 calcium chloride Inorganic materials 0.000 abstract 1
- 238000004040 coloring Methods 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 239000003925 fat Substances 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 239000011888 foil Substances 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 239000004922 lacquer Substances 0.000 abstract 1
- 235000021388 linseed oil Nutrition 0.000 abstract 1
- 239000000944 linseed oil Substances 0.000 abstract 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 abstract 1
- 150000002736 metal compounds Chemical class 0.000 abstract 1
- 150000002739 metals Chemical class 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 229910052718 tin Inorganic materials 0.000 abstract 1
- 239000004408 titanium dioxide Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000001993 wax Substances 0.000 abstract 1
- 229910052726 zirconium Inorganic materials 0.000 abstract 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
- C09B63/00—Lakes
- C09B63/005—Metal lakes of dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
The invention comprises the polyvalent metal lakes of monoazo dyestuffs of formula <FORM:0797850/IV (b)/1> wherein A is a phenyl radical, B is a phenyl or naphthyl radical and X is a sulphonic or carboxylic acid group. The lakes are obtained by coupling a diazotized aminobenzene sulphonic acid containing a further sulphonic acid or carboxylic acid group with a 2-hydroxy-3-naphthoic acid phenyl- or naphthyl-amide and laking the monoazo dye so obtained with polyvalent metal compounds by known methods. The aminobenzene sulphonic acids may contain further substituents such as halogen atoms or alkyl or alkoxy groups and preferably have a sulphonic or carboxylic acid group ortho to the amino group. The 2-hydroxy-3-naphthoic acid arylamides may also contain substituents such as halogen atoms or alkyl or alkoxy group in the arylamide radical. The lakes are prepared by dissolving the isolated dyestuff in water or neutralizing the coupling mixture and adding a soluble salt of a polyvalent metal to the preferably warmed solution. A mixture of salts of two or more metals may be used. Specified salts are those of alkaline earth metals, aluminium, manganese, iron, zirconium and tin. The lakes may be prepared in the presence of dispersing agents or protective substances such as alkali metal soaps of higher fatty acids, colophony soaps and emulsions of fats, oils, waxes, &c., which give lakes of soft texture. The lakes may be precipitated in the presence of substrata such as aluminium hydroxide, barium sulphate or titanium dioxide. The lakes are red to brown-red in colour and are used for colouring lacquers and resins (see Group IV (a)). In examples: (1) diazotized aniline-2 : 5-disulphonic acid is coupled with 2-hydroxy-3-naphthoic acid-11-naphthylamide in the presence of turkey-red oil and sodium acetate, the coupling mixture is neutralized and a linseed oil emulsion and calcium chloride solution added to give a red lake; (2) the barium lake of the dyestuff aniline-2 : 5-disulphonic acid --> 2-hydroxy - 3 - naphthoic acid -21 : 41 - dimethoxy-51-chloroanilide is prepared as in (1) using barium chloride and colophony soap in the laking process; (3) the barium lake of the dyestuff aniline-2 : 5-disulphonic acid --> 2-hydroxy - 3 - naphthoic acid -21 - methyl - 41-chloroanilide, coupled in alkaline medium in the presence of turkey-red oil, is prepared as in (2); (4) the barium lake of the dyestuff aniline-2 : 4-disulphonic acid --> 2-hydroxy-3-naphthoic acid-11-naphthylamide is prepared as in (2); (5) a barium lake is prepared as in (1), the dyestuff 1 - methyl - 2 - aminobenzene - 4 : 6 - disulphonic acid --> 2-hydroxy-3-naphthoic acid-21 : 41 - dimethoxy - 5 - chloroanilide being treated with barium chloride and a vegetable oil emulsion; (6) the calcium lake of the dyestuff 2 - amino - 4 - sulphobenzoic acid --> 2 - hydroxy - 3 - naphthoic acid -21 : 41 - dimethoxy - 51 - chloroanilide is prepared as in (1); (7) the calcium lake of the dyestuff 2-amino-5 - sulphobenzoic acid --> 2 - hydroxy - 3 - naphthoic acid anilide is prepared as in (1); (8) the barium lake of the dyestuff 2-amino-5-sulphobenzoic acid --> 2 - hydroxy - 3 - naphthoic acid -11-naphthylamide is produced as in (1); (9) the dyestuff 2-chloro-5-amino-4-sulphobenzoic acid --> 2-hydroxy-3-naphthoic acid -21 - methyl - 41 - chloroanilide, coupled as in (3), is treated with a vegetable oil emulsion and calcium chloride.ALSO:Polyvalent metal lakes of monoazo dyes of formula <PICT:0797850/IV (a)/1> wherein A is a phenyl radical, B is a phenyl or naphthyl radical and X is a sulphonic or carboxylic acid group (see Group IV (c)) are used to colour polyvinyl chloride compositions. In an Example, a mixture of polyvinyl chloride, dioctyl phthalate, dibutyl tin laurate and the calcium lake of the dye aniline-2 : 5-disulphonic acid --> 2-hydroxy-3-naphthoic acid11-naphthylamide is worked up and drawn out into a red foil.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH797850X | 1955-02-02 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB797850A true GB797850A (en) | 1958-07-09 |
Family
ID=4537432
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3187/56A Expired GB797850A (en) | 1955-02-02 | 1956-02-01 | Manufacture of lakes of monoazo dyes of the benzene-azo-naphthalene series and theiruse |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB797850A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4767844A (en) * | 1985-05-20 | 1988-08-30 | Dainippon Ink And Chemicals, Inc. | Azo lake pigments |
US5047517A (en) * | 1988-09-30 | 1991-09-10 | Hoechst Aktiengesellschaft | Laked pyrazolone azo pigment, process for its preparation and its use |
-
1956
- 1956-02-01 GB GB3187/56A patent/GB797850A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4767844A (en) * | 1985-05-20 | 1988-08-30 | Dainippon Ink And Chemicals, Inc. | Azo lake pigments |
US5047517A (en) * | 1988-09-30 | 1991-09-10 | Hoechst Aktiengesellschaft | Laked pyrazolone azo pigment, process for its preparation and its use |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB797850A (en) | Manufacture of lakes of monoazo dyes of the benzene-azo-naphthalene series and theiruse | |
US2155493A (en) | Monoazo dyestuffs | |
US2257165A (en) | Azo dyestuffs containing chromium in complex union | |
US2117859A (en) | New azo dye and color lakes and their production | |
US1951298A (en) | Azo dyestuff and color lakes made therefrom | |
US2174501A (en) | Sodium salt of lithol red as a dry toner | |
US2811515A (en) | Lakes and the production thereof | |
US2205849A (en) | Azo dyestuffs soluble in water | |
US2028981A (en) | Production of azo dyestuffs | |
US2122127A (en) | Ortho-hydroxyazo dyes and process for manufacturing the same | |
US2915534A (en) | 2, 5-bis(rho-aminophenyl) furan derivatives | |
US2829142A (en) | Metallisable monoazo dyestuffs | |
US2273517A (en) | Azo dyestuffs soluble in water | |
US1962226A (en) | Azo dyes, and method for their preparation | |
US2225443A (en) | Azo dyestuffs | |
US2205481A (en) | Monoazo dyestuffs | |
US1784343A (en) | Lew azo dyestuffs | |
DE675556C (en) | Process for the preparation of monoazo dyes | |
US1474587A (en) | Azo dystuffs | |
US2107159A (en) | Improved coloring material | |
US1429781A (en) | Blue wool dyestuff | |
DE928903C (en) | Process for the preparation of monoazo dyes | |
US2133671A (en) | Azo dyestuffs | |
US914146A (en) | Azo dye and process of making same. | |
US2134038A (en) | Monoazo dyestuffs |