GB773152A - Improvements relating to bis-triazinylamino stilbene compounds and their use as optical brightening agents - Google Patents
Improvements relating to bis-triazinylamino stilbene compounds and their use as optical brightening agentsInfo
- Publication number
- GB773152A GB773152A GB34052/54A GB3405254A GB773152A GB 773152 A GB773152 A GB 773152A GB 34052/54 A GB34052/54 A GB 34052/54A GB 3405254 A GB3405254 A GB 3405254A GB 773152 A GB773152 A GB 773152A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- stilbene
- bis
- methyl
- triazinyl
- 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
- RWFZHFYWPYSEOZ-UHFFFAOYSA-N 1,2-diphenyl-N,N'-bis(triazin-4-yl)ethene-1,2-diamine Chemical class N1=NN=C(C=C1)NC(=C(C1=CC=CC=C1)NC1=NN=NC=C1)C1=CC=CC=C1 RWFZHFYWPYSEOZ-UHFFFAOYSA-N 0.000 title abstract 4
- 238000005282 brightening Methods 0.000 title abstract 3
- 230000003287 optical effect Effects 0.000 title abstract 3
- 239000002253 acid Substances 0.000 abstract 16
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 abstract 9
- 235000021286 stilbenes Nutrition 0.000 abstract 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 8
- 159000000000 sodium salts Chemical class 0.000 abstract 6
- -1 alkali metal salts Chemical group 0.000 abstract 5
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 abstract 4
- 239000003795 chemical substances by application Substances 0.000 abstract 4
- 238000000034 method Methods 0.000 abstract 4
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical class COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 abstract 4
- 238000005406 washing Methods 0.000 abstract 4
- ONADZNBSLRAJFW-UHFFFAOYSA-N 3-methoxy-4-methylaniline Chemical compound COC1=CC(N)=CC=C1C ONADZNBSLRAJFW-UHFFFAOYSA-N 0.000 abstract 3
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 abstract 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 239000000460 chlorine Substances 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical group CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 abstract 2
- ORJSRVJRTUEHFT-UHFFFAOYSA-N 2-ethoxyaniline hypochlorous acid Chemical class ClO.CCOC=1C(=CC=CC1)N ORJSRVJRTUEHFT-UHFFFAOYSA-N 0.000 abstract 2
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 abstract 2
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 abstract 2
- MUPRSFJEAZGKAZ-UHFFFAOYSA-N OCl.COC1=CC=C(N)C=C1 Chemical compound OCl.COC1=CC=C(N)C=C1 MUPRSFJEAZGKAZ-UHFFFAOYSA-N 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 125000004442 acylamino group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000001555 benzenes Chemical class 0.000 abstract 2
- 229920002678 cellulose Polymers 0.000 abstract 2
- 239000001913 cellulose Substances 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 abstract 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 abstract 2
- 150000003142 primary aromatic amines Chemical class 0.000 abstract 2
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 abstract 2
- 239000004753 textile Substances 0.000 abstract 2
- ULHFFAFDSSHFDA-UHFFFAOYSA-N 1-amino-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1N ULHFFAFDSSHFDA-UHFFFAOYSA-N 0.000 abstract 1
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 abstract 1
- WEZAHYDFZNTGKE-UHFFFAOYSA-N 3-ethoxyaniline Chemical compound CCOC1=CC=CC(N)=C1 WEZAHYDFZNTGKE-UHFFFAOYSA-N 0.000 abstract 1
- WOYZXEVUWXQVNV-UHFFFAOYSA-N 4-phenoxyaniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC=C1 WOYZXEVUWXQVNV-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 229920000742 Cotton Polymers 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000004945 acylaminoalkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- DAZLBCIMRZNCRV-UHFFFAOYSA-N aniline;sodium Chemical compound [Na].NC1=CC=CC=C1 DAZLBCIMRZNCRV-UHFFFAOYSA-N 0.000 abstract 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 238000004140 cleaning Methods 0.000 abstract 1
- 239000012459 cleaning agent Substances 0.000 abstract 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 235000010755 mineral Nutrition 0.000 abstract 1
- 239000010446 mirabilite Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000344 soap Substances 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 abstract 1
- 235000017557 sodium bicarbonate Nutrition 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 235000017550 sodium carbonate Nutrition 0.000 abstract 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
- D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
- D21H21/30—Luminescent or fluorescent substances, e.g. for optical bleaching
Abstract
The invention comprises bis-triazinyl-amino-stilbene compounds corresponding to the general formula <FORM:0773152/IV(b)/1> wherein R represents a methyl or ethyl group and A represents a phenyl radical which can be substituted by chlorine, acylamino, alkyl or alkoxy groups, and alkali metal salts thereof. Fluorescent symmetrical bis-triazinylamino-stilbene compounds and their alkali metal salts are produced by a process characterized by reacting 1 mol. of 4.41-bis-[4.6-dihalogen-1.3.5-triazinyl - (2) - amino] - stilbene - 2.21 - disulphonic acids or their salts, obtained from 4.41-diamino - stilbene - 2.21 - disulphonic acid and cyanuric halides, with 2 mols. of a primary aromatic amine of the benzene series which can contain chlorine, acylamino alkyl or alkoxy substituents in the ring and with 2 mol. of a secondary alkylethanolamine in which the alkyl group is methyl or ethyl, the reaction being performed in steps in any order desired in aqueous solution in the presence of an agent neutralizing the mineral acid formed in the reaction so that symmetrical compounds of the above general formula in which R and A have the meaning given above, result: primary aromatic amines of the benzene series mentioned include aminobenzene, 2- and 3-methyl-1 - aminobenzene, 3 - chloro - 1 - aminobenzene, 2-, 3- or 4-methoxy-1-aminobenzenes, 2-ethoxy-1 - aminobenzene, 4 - phenoxy - 1 - amino - benzene, 2.5 - dimethyl - 1 - aminobenzene, 3-methoxy-4-methyl-1-aminobenzene. Sodium carbonate, bicarbonate and acetate may be employed as acid binding agent in the first step and an excess of amine in the second. In examples: the sodium salt of 4.41-bis-[phenylamino - 6 - (b - hydroxyethylmethylamino) - 1.3.5-triazinyl - (2) - amino - stilbene - 2.21 - disul - phonic acid is obtained by reacting with aniline sodium salt of 4.4-bis-[4.6-dichloro-1.3.5-triazinyl - (2) - amino] - stilbene - 2.21 - disulphonic acid, obtained by reacting the sodium salt of 4.41 - diamino - stilbene - 2.21 - disulphonic acid with cyanuric chloride, and heating the product with N-methylethanolamine; similar products are obtained when the aniline in the above process is replaced by o- or m-toluidine, m-chloraniline, m- or o-anisidine or p-xylidine (1); in a similar process the disodium salt of 4.41-bis-[4-(p - methoxyphenylamino) - 6 - (N - ethyl - b - hydroxyethylamino - 1.3.5 - triazinyl - (2) - amino] - stilbene - 2.21 - disulphonic acid is obtained from 4.41-bis-[4.6-dichloro-1.3.5-triazinyl - (2) - amino] - stilbene - 2.21 - disulphonic acid, N-ethyl-monoethanolamine and p-methoxy aniline; similar products are obtained using aniline, m-anisidine or m-phenetidine instead of p-methoxy aniline (2); the disodium salt of 4.41 - bis - [3 - methoxy - 4 - methyl - phenyl - amino) - 6 - (N - methyl - b - hydroxyethyl - amino) - 1.3.5 - triazinyl - (2) - amino] - stilbene-2.21-disulphonic acid is similarly obtained using the disodium salt of 4.41-bis-[4.6 - dichloro - 1.3.5 - triazinyl - (2) - amino] - stilbene - 2.21-disulphonic acid, 3 - methoxy - 4 - methyl - aniline and N - methyl - monoethanolamine; similar products are obtained when the 3-methoxy-4-methyl aniline is replaced by 3-chloro-4-methyl- or -2-methyl-aniline (3); the sodium salt of 4.41-bis-[4-(p-methoxy-phenylamino) - 6 - (N - methyl - b - hydroxyethyl - amino) - 1.3.5 - triazinyl - (2) - amino] - stilbene-2.21-disulphonic acid is similarly obtained using p - anisidine chlorhydrate, 4.41 - bis - [4.6 - di - chloro - 1.3.5 - triazinyl - (2) - amino] - stilbene - 2.21 - disulphonic acid disodium salt and N-methyl-monoethanol; similar compounds are obtained when p-anisidine chlorohydrate is replaced by p-aminodiphenyl ether and o-phenetidine chlorohydrates (4); the sodium salt of 4.41 - bis - [2 - p - acetylaminophenylamino) - 4 - (b - hydroxyethylmethylamino) - triazinyl - (6) - amino] - stilbene - 2.21 - disulphonic acid is obtained in a process similar to (1) when aniline is replaced by p-aminoacetanilide (5). The products of the invention are employed as optical brightening agents, e.g. for cellulose, e.g. in form of fibres and textiles and in washing and cleaning agents (see Group IV (c)).ALSO:Bis-triazinylamino - stilbene compounds corresponding to the general formula <FORM:0773152/IV(b)/1> wherein R represents methyl or ethyl, A represents a phenyl radical which can be substituted by chlorine, acylamino, alkyl or alkoxy groups and alkali metal salts thereof (see Group IVb) are employed as optical brightening agents for cellulose in the form of fibres and textiles and in washing and cleaning compositions. In examples: white cotton poplin is treated in a bath containing the sodium salt of 4 - 41 - bis - [4 - phenylamino - 6 (b - hydroxyethyl - methylamino) - 1 : 3 : 5 - triazinyl - (2) - amino] - stilbene - 2, 21 - disulphonic acid and Glauber's salt (6); and pillow-cases &c. are boiled in a washing liquor containing a soap and perborate washing agent and the sodium salt of 4 : 41 - bis [4 - (p - methoxyphenylamino) - 6 - (b - hydroxyethyl - methylamino) - 1 : 3 : 5 - triazinyl - (2) - amino] - stilbene - 2 : 21 - disulphonic acid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH773152X | 1953-11-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB773152A true GB773152A (en) | 1957-04-24 |
Family
ID=4535578
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB34052/54A Expired GB773152A (en) | 1953-11-26 | 1954-11-24 | Improvements relating to bis-triazinylamino stilbene compounds and their use as optical brightening agents |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB773152A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4549980A (en) * | 1983-10-11 | 1985-10-29 | Mobay Chemical Corporation | White modification of a bis-triazinyl amino stilbene optical brightener and a process for making the same |
| WO2015133999A1 (en) * | 2014-03-04 | 2015-09-11 | Empire Technology Development Llc | Backlight units and methods of making the same |
| USRE46913E1 (en) | 2008-03-26 | 2018-06-26 | Archroma Ip Gmbh | Optical brightening compositions |
-
1954
- 1954-11-24 GB GB34052/54A patent/GB773152A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4549980A (en) * | 1983-10-11 | 1985-10-29 | Mobay Chemical Corporation | White modification of a bis-triazinyl amino stilbene optical brightener and a process for making the same |
| USRE46913E1 (en) | 2008-03-26 | 2018-06-26 | Archroma Ip Gmbh | Optical brightening compositions |
| WO2015133999A1 (en) * | 2014-03-04 | 2015-09-11 | Empire Technology Development Llc | Backlight units and methods of making the same |
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