Classifications

• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
  • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
  • D06L4/60—Optical bleaching or brightening
  • D06L4/65—Optical bleaching or brightening with mixtures of optical brighteners

Definitions

• optical brighteners Venkataraman, The Chemistry of Synthetic Dyes, Vol. V, Chapter VIII.
• French Patent No. 1,415,977 it is also known from French Patent No. 1,415,977 to use mixtures of optical brighteners consisting of 1,4-bis (cyano-2-styryl) benzene, 1,4-bis (cyano-4-styryl) benzene and 4- (cyano-2-styryl) -1- (cyano-4-styryl) benzene.
• a mixture which consists of one of these isomeric bis (cyanostyryl) benzenes, namely 1,4-bis (cyano-2-styryl) benzene and a brightener from the series of naphthalimide derivatives (Chemical Abstracts Vol. 83 , No. 61504 c). It has now been found that the effect of these known mixtures can be exceeded if the mixture known from the French patent mentioned is mixed with other brighteners of the formulas 4 to 8 listed below.
• alkyl and alkoxy groups and other groups derived therefrom contain 1 to 4 carbon atoms.
• the term “non-chromophoric substituents” is to be understood as meaning alkyl, alkoxy, aryl, aralkyl, trifluoromethyl, cycloalkyl, halogen, alkylsulfonyl, carboxy, sulfonic acid, cyano, carbonamide, sulfonamide, carboxylic acid alkyl ester, sulfonic acid alkyl ester.
• component B consisting of one or more compounds of the formulas 2b-6b where R 1 in the 5-position is a hydrogen or chlorine atom, a methyl or phenyl group and R 2 is a hydrogen atom or R 1 and R 2 are both a methyl group in the 5,6- or 5,7-position, n 0 or 1 and B.
• R 14 is (C 1 -C 6 ) alkyl, (C 1 -C 6 ) chloroalkyl, (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) alkyl, hydroxy (C 1 -C 4 ) alkyl or a group of the formula - (CH 2 CH 2 O) n ⁇ R, n 2 or 3 and R hydrogen or (C 1 -C 4 ) alkyl, R, 5 phenyl, halophenyl, (C 1 -C 4 ) -alkylphenyl or (C 1 -C 4 ) -alkoxiphenyl, R 22 is (C 1 -C 4 ) -alkyl and R 23 is cyano or carbo- (C 1 -C 4 ) -alkoxy, where R 3 is hydrogen or (C 1 -C 6 ) alkyl, (C 1 -C 6 ) chloroalkyl, (C 1 -C 4 ) alk
• component B consisting of one or more compounds of the following formulas: wherein R 1 and R 2 in the 5,6-position methyl and B carbomethoxy, R hydrogen, R 1 hydrogen or methyl in the 5-position and B carbomethoxy, cyano or a group of the formulas wherein R 14 and R 22 are (C 1 -C 3 ) alkyl and R 15 is phenyl, 4-methylphenyl or 4-methoxyphenyl, or R 1 is hydrogen, methyl or t-butyl in the 5-position, R 2 is hydrogen or methyl in 7-position and B is phenyl, where R 3 is hydrogen or methoxy, or or where R 2 is hydrogen or methyl.
• component A Mixtures of the following composition are particularly preferred as component A: the proportion of compounds 1 and 3 should be approximately the same.
• the proportion of the individual compounds 1 to 3 in component A can fluctuate within the limits specified, preference being given to mixtures which contain the compounds 1 and 3 in approximately equal parts. From the limits given above for the weight ratios of compounds 1 to 3, it follows that the proportion of compounds 1 and 3 can be 0% and the proportion of compound 2 can be 100%. In this case there is pure connection 2. It is understood that the composition of component A is chosen within the various limits given above so that the sum of all individual compounds is 100%.
• the ratio of compounds 10 and 11 determines the composition of the mixture. If the proportion of 10 is higher, the proportion of compound 1 increases at the expense of compound 3, if the proportion of compound 11 is higher, the proportion of compound 3 in mixtures will be higher than 1.
• one of the symbols X or Q represents an aldehyde group and the other symbol a group of the formulas where R represents an optionally substituted alkyl radical having preferably 1-6 C atoms, an aryl radical preferably phenyl, a cycloalkyl radical or an aralkyl radical, preferably benzyl.
• the process is preferably carried out in solvents in the presence of a proton acceptor.
• solvents which may be mentioned are hydrocarbons such as toluene, xylene, alcohols such as methanol, ethanol, isopropanol, butanol, glycols, hexanols, cyclohexanols, and furthermore ethers such as diisopropyl ether, tetrahydrofuran, dioxane and dimethyl sulfoxide.
• Polar organic solvents such as formamide, dimethylformamide and N-methylpyrrolidone are particularly suitable, with dimethylformamide being particularly emphasized.
• Suitable proton acceptors are primarily basic compounds, such as alkali or alkaline earth metal hydroxides, alcoholates or amides, strongly basic amines and anion exchange resins in the hydroxyl form.
• alkali hydrodes in particular potassium hydroxide, is preferred.
• the reaction temperature depends on the type of components to be reacted, in particular on the type of organic compound containing carbonyl groups and the proton acceptor; it is between - 10 ° C and + 100 ° C, advantageously between 0 ° -50 ° C.
• a preferred embodiment is to bring the reactants together at lower temperatures and to complete the reaction at a higher temperature.
• the claimed process can be carried out, for example, by introducing the proton acceptor in the solvent and adding a solution of the reaction components 9-11 in the solvent, but it is also possible to introduce the compounds 9-11 and adding them to the proteone acceptors.
• a further embodiment consists in presenting the compounds 9-11, in which X or Q represents a group of the formula 12a-d, then first adding the proton acceptor and then the aldehyde component. The reaction generally takes place with intense heat so that cooling may be necessary.
• the reactor mixture is worked up in a known manner, e.g. by adding methanol or ethanol and separating the precipitated products.
• the product mixtures obtained in this way can be analyzed and characterized by HPLC (high pressure liquid chromatography).
• the starting compounds of the formulas 9-11 are known or can be prepared by known processes.
• R, " and R 2" are hydrogen or alkyl and B "is a group of the formulas ⁇ CN or ⁇ COOalkyl and R, 4 .
• Alkyl or methoxyethyl means.
• the following compounds under formula 4 are of particular importance: and
• the mixing ratio for the individual components is between 0.05 and 0.95 parts by weight for component A and correspondingly 0.95 to 0.05 parts by weight for the other compounds of the formulas 4 to 8.
• These compounds of the formulas 4 to 8 can be used individually or in any mixture with one another, the mixing ratio of these compounds with one another being completely uncritical and being able to be varied as desired.
• a mixing ratio of 5 to 50% by weight for component A and 95 to 50% by weight of one or more brighteners of the formulas 4 to 8 (component B) is preferred.
• the optimal mixing ratio of all compounds depends in individual cases on the structure of the respective compounds and can be easily determined by simple preliminary tests.
• the individual components are dispersed in a liquid medium e.g. Water brought into the commercial form.
• the individual components can be dispersed individually and the dispersions can then be added together.
• the individual components can also be mixed together in bulk and then dispersed together. This dispersion process takes place in the usual way in ball mills, colloid mills, bead mills or dispersion kneaders.
• the mixtures according to the invention are particularly suitable for lightening textile material made from linear polyesters, polyamides and acetyl cellulose. However, these mixtures can also be used with good results in mixed fabrics which consist of linear polyesters and other synthetic or natural fiber materials, in particular fibers containing hydroxyl groups, in particular cotton.
• optical brighteners are applied under the conditions customary for the use of optical brighteners, for example using the exhaust process at 90 ° C. to 130 ° C. with or without the addition of accelerators (carriers) or using the thermosol process.
• the water-insoluble brighteners and the mixtures according to the invention can also be used in organic solvents, e.g. Perchlorethylene, fluorinated hydrocarbons can be used in solution.
• the textile material can be treated in the exhaust process with the solvent liquor which contains the optical brightener, or one can impregnate, splash, spray the textile material with the brightener-containing solvent liquor and then dry at temperatures of 120-220 ° C, the optical brightener being used is completely fixed in the fiber.
• the material is squeezed between rollers with a padder so that a moisture absorption of approx. 80% results. This corresponds to an absorption of optical brighteners on the goods of 0.064%.
• the material which had been blocked in this way was then thermosolated on a stenter for 30 seconds at 170 ° (Table I) or 210 ° (Table 11).
• the specified degrees of whiteness according to Ganz were obtained. The degrees of whiteness were measured using a DMC-25 reflectance spectrophotometer. (Carl Zeiss company, Oberkochen).

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• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Detergent Compositions (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Coloring (AREA)
• Prostheses (AREA)
• Dental Preparations (AREA)
• Medicinal Preparation (AREA)
• Paper (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Preparation Of Compounds By Using Micro-Organisms (AREA)

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• 1979
  • 1979-07-21 DE DE19792929687 patent/DE2929687A1/de not_active Withdrawn
• 1980
  • 1980-07-15 ES ES493376A patent/ES493376A0/es active Granted
  • 1980-07-16 AT AT80104163T patent/ATE2017T1/de not_active IP Right Cessation
  • 1980-07-16 US US06/169,296 patent/US4330427A/en not_active Expired - Lifetime
  • 1980-07-16 DE DE8080104163T patent/DE3061345D1/de not_active Expired
  • 1980-07-16 EP EP80104163A patent/EP0023028B1/de not_active Expired
  • 1980-07-18 BR BR8004478A patent/BR8004478A/pt not_active IP Right Cessation
  • 1980-07-18 AU AU60636/80A patent/AU533417B2/en not_active Ceased
  • 1980-07-18 CA CA000356458A patent/CA1151806A/en not_active Expired
  • 1980-07-18 ZA ZA00804365A patent/ZA804365B/xx unknown
  • 1980-07-18 JP JP9769380A patent/JPS5618655A/ja active Granted

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