EP0023028A1 - Mélanges d'agents de blanchiment optiques et leur utilisation - Google Patents
Mélanges d'agents de blanchiment optiques et leur utilisation Download PDFInfo
- Publication number
- EP0023028A1 EP0023028A1 EP80104163A EP80104163A EP0023028A1 EP 0023028 A1 EP0023028 A1 EP 0023028A1 EP 80104163 A EP80104163 A EP 80104163A EP 80104163 A EP80104163 A EP 80104163A EP 0023028 A1 EP0023028 A1 EP 0023028A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- group
- phenyl
- alkoxy
- hydrogen
- 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.)
- Granted
Links
- 0 *C1=CCCC=C1 Chemical compound *C1=CCCC=C1 0.000 description 8
- ZNAXSWNWECQJDZ-DAXSKMNVSA-N C/C(/C(C)=[IH])=N/N Chemical compound C/C(/C(C)=[IH])=N/N ZNAXSWNWECQJDZ-DAXSKMNVSA-N 0.000 description 1
- OZTKINGBFVDAQR-UHFFFAOYSA-N C=CC1=CCCC=C1 Chemical compound C=CC1=CCCC=C1 OZTKINGBFVDAQR-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N C=Cc1ccccc1 Chemical compound C=Cc1ccccc1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- IJVRBLGKBMCRBQ-UHFFFAOYSA-N CC1C(CC(C)(C)C(O)=O)CC=C(C)C1 Chemical compound CC1C(CC(C)(C)C(O)=O)CC=C(C)C1 IJVRBLGKBMCRBQ-UHFFFAOYSA-N 0.000 description 1
- DANMWBNOPFBJSZ-UHFFFAOYSA-N Cc1c(C)c(I)ccc1 Chemical compound Cc1c(C)c(I)ccc1 DANMWBNOPFBJSZ-UHFFFAOYSA-N 0.000 description 1
- RWDDYYBZTWYPLT-NXVVXOECSA-N N#CC1C(/C=C\C2=CCC(CCc(cc3)ccc3C#N)C=C2)=CC=CC1 Chemical compound N#CC1C(/C=C\C2=CCC(CCc(cc3)ccc3C#N)C=C2)=CC=CC1 RWDDYYBZTWYPLT-NXVVXOECSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-O [OH2+]c1ccccc1 Chemical compound [OH2+]c1ccccc1 ISWSIDIOOBJBQZ-UHFFFAOYSA-O 0.000 description 1
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
- 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 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 is a Cyano or carbo (C 1 -C 4 ) alkoxy group or a group of the formulas means, wherein 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 0) n -R, n 2 or 3 and R hydrogen or (C 1 -C 4 ) alkyl, R 15 phenyl,
- 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 where R 2 is hydrogen or methyl.
- component A is prepared 1 mole equivalent of a compound of the formula 2 mole equivalent of a mixture of the
- 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 carbon atoms, an aryl radical, preferably phenyl, a cycloalkyl radical or an aralkyl radical, preferably benzyl.
- the process is preferably carried out in solvents by in the presence of a proton acceptor.
- solvents are hydrocarbons such as toluene.
- Xylene alcohols such as methanol, ethanol, isopropanol butanol, glycols, hexanols, cyclohexanols, also called 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 aceptors 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 metal hydroxides 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 placing 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 add 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, for example by adding methanol or ethanol and separating off 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 14 is alkyl, chloroalkyl, alkoxyalkyl, hydroxyalkyl or a group of the formula - (CH 2 CH 2 O) n -R, where n is 2 or 3 and R is hydrogen or alkyl
- R 15 is phenyl, which can be substituted by one or two chlorine atoms, one or two alkyl, alkoxyalkyl groups, a phenyl, cyano, carboxylic acid, carboalkoxy, carboxamide, S u l - fonic acid, sulfonic acid amide, or sulfonic acid alkyl ester group may
- R 23 is cyano or carboalkoxy and R 22 is alkyl.
- R 3 is hydrogen or alkoxy
- R 4 alkoxy and R 5 is alkyl, alkoxyalkyl or dialkylaminoalkyl.
- R 6 phenyl or the group of the formula and R 7 , the groups of the formulas means.
- R 1 " and R 2" are hydrogen or alkyl and B "is a group of the formulas -CN or -COOalkyl and R 14 " denotes alkyl or methoxyethyl.
- R 14 denotes alkyl or methoxyethyl.
- 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 up to 8 can be used individually but also 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 on the structure of the respective compounds in individual cases and can easily be determined by simple preliminary tests.
- the individual Components are brought into the Hancels form by dispersion in a liquid medium, for example water.
- the individual components can be dispersed individually and then the dispersions can 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 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 solution in organic solvents, for example perchlorethylene, fluorinated hydrocarbons.
- 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, whereby the optical brightener is completely fixed in the fiber.
- the material is squeezed between rollers with a padder so that there is a moisture absorption of approx. 80%. This corresponds to an absorption of optical brighteners on the goods of 0.064%.
- the material which has been blocked in this way was then thermosolated on a stenter frame for 30 seconds at 170 ° (Table I) or 210 ° (Table II).
- the specified degrees of whiteness according to Ganz were obtained.
- the degrees of whiteness were measured using a DMC-25 reflectance spectrophotometer. ( C arl Zeiss company, Oberkochen.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
- Medicinal Preparation (AREA)
- Prostheses (AREA)
- Dental Preparations (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Paper (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT80104163T ATE2017T1 (de) | 1979-07-21 | 1980-07-16 | Mischungen von optischen aufhellern und deren verwendung. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2929687 | 1979-07-21 | ||
DE19792929687 DE2929687A1 (de) | 1979-07-21 | 1979-07-21 | Mischungen von optischen aufhellern |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0023028A1 true EP0023028A1 (fr) | 1981-01-28 |
EP0023028B1 EP0023028B1 (fr) | 1982-12-15 |
Family
ID=6076455
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP80104163A Expired EP0023028B1 (fr) | 1979-07-21 | 1980-07-16 | Mélanges d'agents de blanchiment optiques et leur utilisation |
Country Status (10)
Country | Link |
---|---|
US (1) | US4330427A (fr) |
EP (1) | EP0023028B1 (fr) |
JP (1) | JPS5618655A (fr) |
AT (1) | ATE2017T1 (fr) |
AU (1) | AU533417B2 (fr) |
BR (1) | BR8004478A (fr) |
CA (1) | CA1151806A (fr) |
DE (2) | DE2929687A1 (fr) |
ES (1) | ES493376A0 (fr) |
ZA (1) | ZA804365B (fr) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3070041D1 (en) * | 1979-12-13 | 1985-03-07 | Ciba Geigy Ag | Optical brighteners from bistyryl benzene, process for their preparation and their use |
CH650792A5 (en) * | 1979-12-13 | 1985-08-15 | Ciba Geigy Ag | Optical brighteners from bisstyrylbenzene compounds and preparation thereof |
DE3001065A1 (de) * | 1980-01-12 | 1981-07-16 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von optischen aufhellern |
DE3027479A1 (de) * | 1980-07-19 | 1982-03-04 | Hoechst Ag, 6000 Frankfurt | Mischungen von optischen aufhellern und deren verwendung |
DE3104992A1 (de) * | 1981-02-12 | 1982-08-26 | Hoechst Ag, 6000 Frankfurt | "mischungen von optischen aufhellern" |
DE3313332A1 (de) * | 1983-04-13 | 1984-10-18 | Hoechst Ag, 6230 Frankfurt | Mischungen von optischen aufhellern zum aufhellen von polyvinylchlorid |
DE3339383A1 (de) * | 1983-10-29 | 1985-05-09 | Bayer Ag, 5090 Leverkusen | Distyrylverbindungen |
JPS60217999A (ja) * | 1984-03-31 | 1985-10-31 | 株式会社新潟鐵工所 | 流体荷役装置 |
US4778622A (en) * | 1986-03-21 | 1988-10-18 | Ciba-Geigy Corporation | Mixtures of fluorescent whitening agents |
DE3764040D1 (de) * | 1986-07-01 | 1990-09-06 | Ciba Geigy Ag | 1,4-distryrylbenzolverbindungen und deren mischungen mit anderen 1,4-distryrylbenzolverbindungen. |
CH671956A5 (fr) * | 1987-01-29 | 1989-10-13 | Ciba Geigy Ag | |
US4830763A (en) * | 1987-02-26 | 1989-05-16 | Ciba-Geigy Corporation | Process for increasing the degree of whiteness of polyester-containing textile material |
ES2053807T3 (es) * | 1987-11-27 | 1994-08-01 | Ciba Geigy Ag | Dispersion blanqueadora acuosa y procedimiento para su preparacion. |
EP0321393B1 (fr) * | 1987-11-27 | 1993-02-17 | Ciba-Geigy Ag | Dispersion d'agent de blanchiment optique |
US6492032B1 (en) | 2000-10-12 | 2002-12-10 | Eastman Chemical Company | Multi-component optically brightened polyolefin blend |
DE10219993A1 (de) * | 2002-05-03 | 2003-11-20 | Basf Ag | Verfahren zum Aufhellen von textilen Materialien |
ES2316862T3 (es) * | 2002-12-10 | 2009-04-16 | Ciba Holding Inc. | Mezclas de agentes de blanqueo fluorescentes. |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB913735A (en) * | 1959-06-24 | 1962-12-28 | Basf Ag | Optically brightened macromolecular organic substances |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH533670A (de) * | 1968-12-05 | 1973-02-15 | Ciba Geigy Ag | Optische Aufhellmittel enthaltende anorganische Weisspigmente |
DE2037854C2 (de) * | 1970-07-30 | 1983-07-07 | Bayer Ag, 5090 Leverkusen | 3-(4-Chlor-1-pyrazolyl)-7-v-triazol-2-yl-cumarin-Verbindungen und deren Verwendung zum optischen Aufhellen |
JPS51100522A (ja) * | 1975-03-01 | 1976-09-04 | Kubota Ltd | Sagyokiratsukaboshisochi |
JPS544973A (en) * | 1977-06-13 | 1979-01-16 | Daiken Trade & Industry | Waterproof treatment for board |
-
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 DE DE8080104163T patent/DE3061345D1/de not_active Expired
- 1980-07-16 AT AT80104163T patent/ATE2017T1/de not_active IP Right Cessation
- 1980-07-16 EP EP80104163A patent/EP0023028B1/fr not_active Expired
- 1980-07-16 US US06/169,296 patent/US4330427A/en not_active Expired - Lifetime
- 1980-07-18 AU AU60636/80A patent/AU533417B2/en not_active Ceased
- 1980-07-18 BR BR8004478A patent/BR8004478A/pt not_active IP Right Cessation
- 1980-07-18 ZA ZA00804365A patent/ZA804365B/xx unknown
- 1980-07-18 CA CA000356458A patent/CA1151806A/fr not_active Expired
- 1980-07-18 JP JP9769380A patent/JPS5618655A/ja active Granted
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB913735A (en) * | 1959-06-24 | 1962-12-28 | Basf Ag | Optically brightened macromolecular organic substances |
Non-Patent Citations (1)
Title |
---|
CHEMICAL ABSTRACTS, Band 83, Nr. 8, 25. August 1975, Zusammenfassung Nr. 61504c, Seite 165, Columbus, Ohio, US; & JP-A-50 025 877 (NIPPON KAYAKU CO. LTD.) (18-03-1975) * |
Also Published As
Publication number | Publication date |
---|---|
EP0023028B1 (fr) | 1982-12-15 |
ATE2017T1 (de) | 1982-12-15 |
ES8105055A1 (es) | 1981-05-16 |
AU533417B2 (en) | 1983-11-24 |
DE2929687A1 (de) | 1981-02-12 |
JPS5618655A (en) | 1981-02-21 |
US4330427A (en) | 1982-05-18 |
ES493376A0 (es) | 1981-05-16 |
AU6063680A (en) | 1981-01-22 |
ZA804365B (en) | 1981-07-29 |
DE3061345D1 (en) | 1983-01-20 |
BR8004478A (pt) | 1981-01-27 |
CA1151806A (fr) | 1983-08-16 |
JPH0116867B2 (fr) | 1989-03-28 |
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