GB973113A - Improvements relating to bis-triazinylaminostilbene compounds and their use for optically brightening organic materials - Google Patents
Improvements relating to bis-triazinylaminostilbene compounds and their use for optically brightening organic materialsInfo
- Publication number
- GB973113A GB973113A GB27226/61A GB2722661A GB973113A GB 973113 A GB973113 A GB 973113A GB 27226/61 A GB27226/61 A GB 27226/61A GB 2722661 A GB2722661 A GB 2722661A GB 973113 A GB973113 A GB 973113A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- bis
- stilbene
- ethoxy
- methoxy
- 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
- 238000005282 brightening Methods 0.000 title abstract 4
- 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 2
- 239000011368 organic material Substances 0.000 title 1
- -1 alkali metal salt Chemical class 0.000 abstract 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 5
- 150000003839 salts Chemical class 0.000 abstract 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 3
- 235000017550 sodium carbonate Nutrition 0.000 abstract 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 239000003599 detergent Substances 0.000 abstract 2
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 abstract 2
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 abstract 2
- 159000000000 sodium salts Chemical class 0.000 abstract 2
- 229910052938 sodium sulfate Inorganic materials 0.000 abstract 2
- 235000011152 sodium sulphate Nutrition 0.000 abstract 2
- 235000019832 sodium triphosphate Nutrition 0.000 abstract 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 235000019818 tetrasodium diphosphate Nutrition 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 abstract 1
- UASUIPULTWSLAD-UHFFFAOYSA-N 2-(2-phenylethenyl)aniline;2-(1,3,5-triazin-2-yl)-1,3,5-triazine Chemical class C1=NC=NC(C=2N=CN=CN=2)=N1.NC1=CC=CC=C1C=CC1=CC=CC=C1 UASUIPULTWSLAD-UHFFFAOYSA-N 0.000 abstract 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 abstract 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 abstract 1
- PWGVOCGNHYMDLS-UHFFFAOYSA-N 3-(2-methoxyethoxy)propan-1-amine Chemical compound COCCOCCCN PWGVOCGNHYMDLS-UHFFFAOYSA-N 0.000 abstract 1
- ZTGKHKPZSMMHNM-UHFFFAOYSA-N 3-(2-phenylethenyl)benzene-1,2-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(C=CC=2C=CC=CC=2)=C1S(O)(=O)=O ZTGKHKPZSMMHNM-UHFFFAOYSA-N 0.000 abstract 1
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 229910006074 SO2NH2 Inorganic materials 0.000 abstract 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 238000010936 aqueous wash Methods 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 239000000337 buffer salt Substances 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000010531 catalytic reduction reaction Methods 0.000 abstract 1
- 239000001913 cellulose Substances 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 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
- 239000002657 fibrous material Substances 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 150000003142 primary aromatic amines Chemical class 0.000 abstract 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 abstract 1
- 229940048086 sodium pyrophosphate Drugs 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 235000021286 stilbenes Nutrition 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/40—Dyes ; Pigments
- C11D3/42—Brightening agents ; Blueing agents
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Coloring (AREA)
Abstract
The invention comprises bis-triazinyl aminostilbene compounds of the general formula <FORM:0973113/C1/1> and water-soluble salts thereof, wherein A represents an aromatic radical, Y represents an alkyl or alkoxyalkyl radical in which each alkyl and alkoxy group contains not more than 3 carbon atoms and n is 2 or 3. They may be prepared by reacting 1 mol. of 4,41-bis(411,611-dihalo-111, 311, 511-triazinyl-211-amino) stilbene-2, 21-disulphonic acid or water-soluble salt thereof with, in any order, 2 moles of a primary aromatic amine A-NH2 and 2 moles of an amine NH2-(CH2)n-O-Y. The sulphonic acid is preferably used as an aqueous solution of a soluble salt thereof; the first step may be effected at 5 DEG -60 DEG C. and the second at 70 DEG -100 DEG C. The reactions may be effected in the presence of a buffer salt, e.g., an alkali metal salt of either a fatty acid having not more than 4 carbon atoms or carbonic acid. In typical examples, (1) an aqueous solution of the di-sodium salt of 4,41-diamino-stilbene-2, 21-disulphonic acid and Na2CO3 is added to cyanuric chloride in aqueous acetone yielding a suspension of the di-sodium salt of 4, 41-bis(411, 611-dichloro-111, 311, 511-triazinyl amino) stilbene-2, 21-di-sulphonic acid to which is first added an acetone solution of aniline and Na2CO3 to maintain alkalinity and then 3-methoxypropyl amine and the product is thereafter salted out; (3) 2-methoxy ethylamine and Na2CO3 are added to the di-sodium salt of the bis(dichlorotriazinyl amino) stilbene disulphonic acid of (1) in water followed by the addition of, for example, 1- or 2-amino-naphthalene and NaOH. Other compounds of the above general formula are prepared wherein A represents phenyl or phenyl substituted by methyl, methoxy, methyl sulphonyl, -COOH, -CONH2, methyl amido-, -SO2NH2, chlorine or bromine and Y-O-(CH2)nis methoxy methyl, methoxy ethyl, ethoxy ethyl, propoxy ethyl, methoxy propyl, ethoxy propyl, 3-(methoxy ethoxy)-propyl, 2-(methoxy ethoxy) ethyl or 2-(ethoxy ethoxy) ethyl. The aromatic group A may also be fluorine substituted. The products may be used as optical brightening agents for detergents (see Division C5) and organic fibres (see Division D1). Amines of the general formula Y-O(CH2)n-NH2 where Y and n are as defined above may be prepared by reacting strong acid (e.g. hydrochloric) esters of the corresponding hydroxy compounds with NH3 under pressure. 3-(methoxy ethoxy) propylamine is obtained by catalytic reduction of the corresponding nitrile.ALSO:Detergent compositions comprise, as a brightening agent, a bis-triazinyl amino stilbene derivative having the general formula <FORM:0973113/C4-C5/1> or a water-soluble salt thereof, where A is an aromatic radical which may bear substituents, Y is an alkyl or alkoxy alkyl radical, the alkyl and alkoxy groups both having not more than 3 carbon atoms, and n is 2 or 3. Example 7 describes a composition in powder form comprising lauryl sulphate, dodecyl benzene sulphonate, sodium tripolyphosphate, tetrasodium pyrophosphate, sodium sulphate and the sodium salt of 4,41 - bis[411 - (b - ethoxyethylamino) - 611 - (p - methylphenylamino) - 111,311,511 - triazinyl - (211) - amino] - stilbene - 2,21 - disulphonic acid. Other examples of the above-defined brightening agents are provided.ALSO:Organic fibrous material is optically brightened by treatment with a stilbene derivative having the general formula <FORM:0973113/D1-D2/1> or water-soluble salts thereof, wherein A represents an aromatic radical which may bear, for example, C1-4 alkyl, C1-4 alkoxy, COOH, amido, sulphonamido, alkyl sulphonyl, Cl, Br or F substituents, Y represents an alkyl or alkoxyalkyl group, each alkyl and alkoxy group thereof containing not more than 3 carbon atoms and n is 2 or 3. They may be used in neutral or alkaline wash liquors for the treatment of cellulose materials. Example 8 describes the washing of household linen using an aqueous wash comprising the sodium salt of 4,41-bis-[411-(b -ethoxy ethylamino)-611-(p-methyl phenylamino)-111, 311, 511-triazinyl amino]-stilbene-2,21-disulphonic acid, lauryl sulphate, dodecyl benzene sulphonate, sodium tripolyphosphate, sodium pyrophosphate and sodium sulphate. Numerous other stilbene derivatives of the above class are mentioned (see Division C2).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH863760A CH386436A (en) | 1960-07-28 | 1960-07-28 | Process for the preparation of bis-triazinylaminostilbene compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB973113A true GB973113A (en) | 1964-10-21 |
Family
ID=4342921
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27226/61A Expired GB973113A (en) | 1960-07-28 | 1961-07-27 | Improvements relating to bis-triazinylaminostilbene compounds and their use for optically brightening organic materials |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3272805A (en) |
| CH (1) | CH386436A (en) |
| DE (1) | DE1419333B1 (en) |
| ES (1) | ES269387A1 (en) |
| GB (1) | GB973113A (en) |
| GR (1) | GR29903B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3538009A (en) * | 1967-02-01 | 1970-11-03 | Cincinnati Milling Machine Co | Method for reducing skin irritation in detergent compositions |
| US3925260A (en) * | 1969-04-09 | 1975-12-09 | Ciba Geigy Corp | Crystalline forms of 4,4-bis-triazinylaminostilbene derivatives and processes for making same |
| BE793315A (en) * | 1971-12-27 | 1973-06-27 | Ciba Geigy | NEW DERIVATIVES OF STILBENE |
| DE10149313A1 (en) * | 2001-10-05 | 2003-04-17 | Bayer Ag | Use of aqueous brightener preparations to lighten natural and synthetic materials |
| US7270771B2 (en) * | 2002-07-05 | 2007-09-18 | Ciba Specialty Chemicals Corporation | Triazinylaminostilbene disulphonic acid mixtures |
| KR20090034290A (en) * | 2007-10-02 | 2009-04-07 | 박종원 | Power generating apparatus using fluid |
| EP2135997B1 (en) * | 2008-06-11 | 2011-01-05 | Kemira Germany GmbH | Composition and process for whitening paper |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2667458A (en) * | 1954-01-26 | Textile treating materials | ||
| US3177207A (en) * | 1965-04-06 | Nh-chs | ||
| DE942396C (en) * | 1953-11-26 | 1956-05-03 | Geigy Ag J R | Process for the preparation of fluorescent bistriazinylaminostilbene compounds |
| BE568156A (en) * | 1957-06-06 | |||
| NL247686A (en) * | 1959-01-24 |
-
1960
- 1960-07-28 CH CH863760A patent/CH386436A/en unknown
-
1961
- 1961-07-27 GB GB27226/61A patent/GB973113A/en not_active Expired
- 1961-07-27 DE DE19611419333 patent/DE1419333B1/en active Pending
- 1961-07-27 GR GR610129903A patent/GR29903B/en unknown
- 1961-07-27 ES ES0269387A patent/ES269387A1/en not_active Expired
-
1964
- 1964-07-02 US US380033A patent/US3272805A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US3272805A (en) | 1966-09-13 |
| GR29903B (en) | 1966-04-16 |
| CH386436A (en) | 1965-01-15 |
| ES269387A1 (en) | 1962-01-01 |
| DE1419333B1 (en) | 1970-05-21 |
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