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

Definitions

• the present invention concerns new 4,4'-bis-triazinylat1'ea ted q
• the Willa-Solubility 9 Products minostilbene compounds processes for the production havlng afllfllty f the fibers Ofifin too sllght at low thereof, their use for the optical brightening of organic 15 temperatures whlch also calls Spots to appear on the material, in particular of cellulose material, agents havtreated matenalsing a content of such compounds, as well as, as industrial It 110W P6611 u d that these disadvantages can product, the material brightened therewith be ellmlnated 1n householduse 1f 4,4 :blS-tI'haZHIYlEimIHO- It is Well known that white ,[eXtfle mawrial such as strlbene compounds according to the invention are used.
• gigg i gfizr gi is ig $12 3 833;; possibly in the presence of buffer salts, in steps and in any order esired with 2 mols of a rimar aromatic amine of textile cellulosic materials, in particular cotton m-atenals, the general formula p y are given increasing contents of textile finishes 1n the form of synthetic resins, for instance as anti-crease finish 2 n in dry state, and so-called non-resin finishes which yield to form a compound of the general formula
• A--NH NHA SOaH l CN I NC Ni ONH-C OH OHNHO N (IIZN s o H YO(CH2)DNH a NH(GHa)u-OY (II so-called cross-linked cellulose as anti-crease finish in wet
• A represents a radical of the benzene series, ifiiniltt
• a particularly valuable class of 4,4'-bis-triazinylaminodetergents as they are used, in particular in powder form stilbene compounds according to the invention are those in the operation of automatic washing machines, and of the formula A is preferably an unsubstituted phenyl radical.
• the 4,4-bis-(4",6"-dihalogen-1",3, 5"-triazinyl- (2" -amino) -sti1bene-2,2'-disulphonic acid is reacted preferably in the form of its water soluble salts in aqueous solution at 5-60 C. and, in the second step it is reacted at 70-100" C. by known methoxy with the amino compounds used according to the invention, possibly in the presence of alkali metal salts of low fatty acids or of carbonic acid such as, e.g., sodium acetate or sodium carbonate, as agents buffering the mineral acid.
• the amines of Formula I used according to the invention are obtained, for example, by reacting esters, obtained from corresponding hydroxy compounds with strong acids such as halogen hydracid, with ammonia under pressure.
• the new triazinylstilbene compounds according to the invention ares isolated from the reaction mixture preferably in the form of their alkali metal salts which, after drying, have good water solubility. In aqueous and in neutral or alkaline washing liquors they have good afiinity to cellulose material and good levelling power. Compared with the previously known 4,4-bis-(diaminotriazynamino]-stilbene-2,2'-disulphonic acid formed and the acid liberated is neutralised by the simultaneous addition of an aqueous solution of 27 parts of sodium carbonate. The yellowish suspension is then stirred at room temperature (-25) until the aminobenzene has completely disappeared.
• the new brightening agent In aqueous solution in daylight, the new brightening agent has a blue to blue-violet fluorescence depending on the degree of dilution and, in spite of its very good water solubility, it has excellent affinity to cellulose fibres. If the product is incorporated into a usual marketed washing agent, then cellulose materials washed therewith are very beautifully optically brightened even when the washing is performed under mild conditions If in this example, the 46.5 parts of aminobenzene are replaced by 53.5 parts of 3-methyl-l-aminobenzene or 61.5 parts of 3-methoxy-l-aminobenzene, then brightening agents with similar properties are obtained.
• the temperature is then raised to -95 and a solution of 8 parts of sodium hydroxide in 20 parts of water is poured in within 2 hours.
• the reaction mixture is stirred another hour at 90-l00 and then parts of sodium chloride are added.
• the reaction 93 parts of cyanuric chloride are dissolved in 450 by volume of acetone.
• the solution is poured, while stirring, into 2250 parts of ice/Water.
• a solution of 103.5 parts of the sodium salt of 4,4-diaminostilbene- 2,2'-disulphonic acid and 27 parts of sodium carbonate in 1200 parts of water is poured, within 1 hour while stirring well at 0-5 into the cyanuric chloride suspension so obtained.
• the Z-(B-ethoxyethoxy)-ethylamine is obtained from 2-(fi-ethoxyethoxy)-ethyl chloride (produced from diethylene glycol monoethyl ether and SOCl by heating in an autoclave with ammonia at 120.
• the disodium salt of 4,4-bis-[4"-(,B-methoxyethylamino)-6"- (m chlorophenylamino) 1",3",5 triazinyl (2")- amino]-2,2-disulphonic acid so obtained is a yellowish powder which dissolves easily in water; it is excellently suited for the optical brightening of white cotton fabrics in washing liquors.
• Equally-active products are obtained if in this example, the Z-methoxyethylamine is replaced by 22 parts of 3- methoxypropylamine or if the 3-chloro-l-aminobenzene is replaced by the same amount of 4-chloro-1-aminobenzene. In the latter case, a somewhat more diflicultly soluble product is obtained.
• optical brightening agents which are suitable for combination with washing agents for the brightening of cellulose fibres are obtained if 1 mol of the sodium salt of 4,4'-bis-[4",6"-dichl0ro-1",3",5"-triazinyl-(2")- amino]-stilbene-2,2'-disulphonic acid is successively re- If, in this example, the 22 parts of 2-ethoxyethylamine 75 acted in the manner described above with 2 mols of each of the following arylamines and alkoxyalkylamines:
• EXAMPLE 6 A heavy-duty non-soap detergent mixture consisting of 8 parts of lauryl sulfate, 11 parts of dodecylbenzene sulfonate, 11 parts of sodium tripolyphosphate, 17 parts of tetrasodium pyrophosphate and 37 parts of sodium sulfate is worked up into a paste with a solution of 0.1 part of the sodium salt of 4,4'-bis-[4"-(/3-ethoxyethylamino) 6" (p methylphenylamino) 1",3",5-triazinyl-(2")-amino] -stilbene-2,2'-disulfonic acid described in Example 2 in 170 parts of water. This paste is then dried at 60 and then milled. In daylight, the washing powder obtained has a considerably whiter appearance than the same washing composition produced without the addition of the optical brightening agent.
• EXAMPLE 7 1 part of household linen is washed for 20 minutes at 60 with 10 parts of a washing liquor which contains 8 g. per liter of the washing agent produced according to Example 6. The goods are then rinsed and dried. In spite of the relatively low washing temperature, a dazzling white wash is obtained.
• EXAMPLE 8 A heavy duty detergent mixture consisting of 7.8 parts by weight of lauryl sulfate,
• optical brightener is intimately mixed with normal aqueous sodium hydroxide solution (10 ml. per g. of brightener) and when the brightener is thoroughly dispersed, about 200 to 300 ml. of water (per gram of brightener) are added.
• the other ingredients of the detergent mixture are mixed with each other separately and intimately using a sufficient amount of water to obtain a creamy paste, the latter is dried at 60 and granulated.
• the detergent granules are then added to the slurry of brightener and the mixture is repeatedly and thoroughly stirred until a smooth, creamy mix is obtained.
• the resulting slurry is then spread into a uniform layer on a flat surface and dried in an oven at for 16 hours.
• the resulting cake is allowed to cool to room temperature, left standing for at least 30 minutes and then crushed and placed in a desiccator.
• the dried chunks of detergent mixture are then forced through a 20 mesh screen and, if desired, the resulting powder is transferred to 60 mesh screen to remove the fine portion.
• EXAMPIJE 9 In a similar manner as described in Example 8 there is produced a synthetic, non-soap, heavy-duty detergent of Disodium 4,4-bis[-4-(B-ethoxy ethylamino)-6" phenylamino 1",3",5",-triazinyl-(2") amino]- stilbene-2,2'-disulfon ate EXAMPLE 10 A heat-liquifia-ble soap for use in washing machines is produced as follows:
• a beautiful white, free-flowing washing powder is obtained which brightens anti-crease finished cotton increasingly with successive washings, and without greenish shade in spite of accumulation of the brightening agent on the fiber.
• EXAMPLE 11 A non-ionogenic washing agent was prepared by intimately mixing with each other the following ingredients Parts by weight terials imparting to the same a pure white appearance Nonylphenol polyglyc-olether with 15 ethylenoxy which does not develop a greenish hue even after 20 groups l1 washings.
• the 4,4'-bis-triazinylaminostilbene compound of the formula 6 The 4,4'-bis-triazinylaminostilbene compound of the formula SlOQH SOzH I NH-CHz-CHz-CHg-OCH;

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• Chemical & Material Sciences (AREA)
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• 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)
• Coloring (AREA)
• Nitrogen Condensed Heterocyclic Rings (AREA)

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Cited By (6)

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Citations (4)

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• 1960
  • 1960-07-28 CH CH863760A patent/CH386436A/de unknown
• 1961
  • 1961-07-27 DE DE19611419333 patent/DE1419333B1/de active Pending
  • 1961-07-27 GR GR610129903A patent/GR29903B/el unknown
  • 1961-07-27 GB GB27226/61A patent/GB973113A/en not_active Expired
  • 1961-07-27 SE SE771661A patent/SE219199C1/sv unknown
  • 1961-07-27 ES ES0269387A patent/ES269387A1/es not_active Expired
• 1964
  • 1964-07-02 US US380033A patent/US3272805A/en not_active Expired - Lifetime

Patent Citations (4)

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