EP0023027A1 - Mélanges d'agents de blanchiment optique, leur préparation et leur utilisation - Google Patents
Mélanges d'agents de blanchiment optique, leur préparation et leur utilisation Download PDFInfo
- Publication number
- EP0023027A1 EP0023027A1 EP80104162A EP80104162A EP0023027A1 EP 0023027 A1 EP0023027 A1 EP 0023027A1 EP 80104162 A EP80104162 A EP 80104162A EP 80104162 A EP80104162 A EP 80104162A EP 0023027 A1 EP0023027 A1 EP 0023027A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- compound
- weight
- compounds
- formula
- oder
- 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.)
- Withdrawn
Links
- SLENVLASKTZHDW-UHFFFAOYSA-N C=Cc1ccccc1C#N Chemical compound C=Cc1ccccc1C#N SLENVLASKTZHDW-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N c1ccccc1 Chemical compound c1ccccc1 UHOVQNZJYSORNB-UHFFFAOYSA-N 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
- the proportion of the individual compounds 1 to 3 in the mixture can fluctuate within the limits specified, preference being given to mixtures which contain the compounds 1 and 3 in approximately equal proportions. 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 compound 2, which is also the subject of the present invention.
- composition of the mixtures is chosen within the various limits given above so that the sum of all individual compounds is 100%.
- the invention further relates to a process for the preparation of such mixtures, characterized in that that you have 1 mole equivalent of a compound of formula with a total of 2 mole equivalent of a mixture of the compounds and implements.
- the ratio of compounds 5 and 6 determines the composition of the mixture according to the invention. If the proportion of 5 is higher, the proportion of compound 1 increases at the expense of compound 3, if the proportion of compound 6 is higher, the proportion of compound 3 in mixtures will be higher than 1.
- R represents an optionally substituted alkyl radical with 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 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 also 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.
- Primary basic compounds such as alkali or alkaline earth metal hydroxides, alcoholates or amides, strongly basic amines and anion exchange resins in the hydroxyl form are suitable as proton acceptors.
- 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 ° and + 100 ° C, advantageously between 0 ° - 50 ° C.
- a preferred embodiment consists of bringing the reactants together at lower temperatures and completing 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 4-6 in the solvent, but it is also possible to add the compounds 4-6 and adding the proton acceptor.
- a further embodiment consists in presenting the compounds 4 or 5 and 6, in which X or Q represents a group of the formulas 7 ad, 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 reaction mixture is worked up in a known manner, for example by adding methanol or ethanol and removing 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 4-6 are known or can be prepared by known processes.
- the compounds 1, 2 and 3 in pure form and then to mix them.
- the compounds of the formulas 1 and 3 are already known; the compound of the formula 2 can be obtained, for example, in the following way by processes which are known per se:
- the mixture of the compound 1-3 according to the invention can be used, for example, without any restriction to be expressed by the following overview, for the brightening of the following groups of organic materials, insofar as optical brightening is possible.
- the organic materials to be optically brightened can belong to the most varied of processing states (raw materials, semi-finished or finished products).
- they can be in the form of a wide variety of shaped structures, i.e.
- shaped structures i.e.
- three-dimensionally extended bodies such as plates, profiles, injection moldings, various types of workpieces, chips, granules or foams
- two-dimensionally designed bodies such as films, foils, lacquers, coatings, impregnations and coatings or as predominantly one-dimensionally designed bodies such as threads, fibers Flakes, wires.
- said materials can also be in unshaped states in a wide variety of homogeneous or inhomogeneous forms of distribution, such as e.g. as powders, solutions, emulsions, dispersions, latices, pastes or waxes.
- Fiber materials can be, for example, as endless threads (drawn or undrawn), staple fibers, flakes, extrudates, textile threads, yarns, threads, non-woven fabrics, felts, wadding, flocking structures or as textile fabrics or textile composites, knitted fabrics, and as papers, cardboards or paper pulps are available.
- the compounds to be used according to the invention are of importance, inter alia, for the treatment of textile organic materials, in particular textile fabrics, such as powders, solutions, emulsions, dispersions, latices, pastes or waxes.
- Fiber materials can be, for example, as endless threads (drawn or undrawn), staple fibers, flakes, extrudates, textile threads, yarns, threads, non-woven fabrics, felts, wadding, flocking structures or as textile fabrics or textile composites, knitted fabrics, and as papers, cardboards or paper pulps are available.
- the compounds to be used according to the invention include Significance for the treatment of textile organic materials, especially textile fabrics. If fibers which can be in the form of staple fibers or continuous filaments, in the form of strands, fabrics, knitted fabrics, nonwovens, flocked substrates or composites, are to be optically brightened according to the invention, this is advantageously done in an aqueous medium in which the compounds in question are in finely divided form (suspensions, so-called microdispersions, optionally solutions) are present. If necessary, dispersants, stabilizers, wetting agents and other auxiliaries can be added during the treatment.
- the new optical brighteners according to the present invention can furthermore be added to or incorporated into the materials before or during their shaping.
- they can be added to the molding compound or injection molding compound during the production of films, foils (e.g. rolling in polyvinyl chloride in the heat) or moldings.
- the combined treatment can in many cases advantageously be carried out with the aid of corresponding stable preparations which contain the optically brightening compounds in such a concentration that the desired lightening effect is achieved.
- the brighteners are brought to full effect by post-treatment.
- This can be a chemical (e.g. acid treatment), a thermal (e.g. heat) or a combined chemical / thermal treatment.
- This is how, for example, the optical brightening of a number of fiber substrates, e.g. polyester fibers, with the brighteners according to the invention expediently in such a way that these fibers with the aqueous dispersions (optionally also solutions) of the brighteners at temperatures below 75 ° C, e.g. at room temperature, impregnated and subjected to a dry heat treatment at temperatures above 100 ° C, where it is generally advisable to previously the fiber material at a moderately elevated temperature, e.g.
- the heat treatment in the dry state is then advantageously carried out by heating in a drying chamber, by ironing in the specified temperature interval or by treatment with dry, superheated steam.
- the drying and dry heat treatment can also be carried out immediately one after the other or combined in a single operation.
- the amount of the new optical brightener to be used according to the invention can vary within wide limits. Even with very small quantities, in certain cases e.g. of 0.001 percent by weight, a clear and durable effect can be achieved. However, amounts of up to about 0.8 percent by weight and optionally up to about 2 percent by weight can also be used. For most practical purposes, amounts between 0.005 and 2, preferably 0.1 to 0.5 percent by weight are preferred.
- the brighteners as such, i.e. to be used purely, but mixed with a wide variety of auxiliaries and coupling agents, e.g. anhydrous sodium sulfate, sodium sulfate decahydrate, sodium chloride, sodium carbonate, alkali metal phosphates, such as sodium or potassium orthophosphate, sodium or potassium pyrophosphate and sodium or potassium tripolyphosphates or alkali metal silicates.
- auxiliaries and coupling agents e.g. anhydrous sodium sulfate, sodium sulfate decahydrate, sodium chloride, sodium carbonate, alkali metal phosphates, such as sodium or potassium orthophosphate, sodium or potassium pyrophosphate and sodium or potassium tripolyphosphates or alkali metal silicates.
- the new optical brighteners have the particular advantage that they can also be used in the presence of active chlorine dispensers, e.g. Hypochloride, are effective and without significant loss of effects in washing baths with nonionic detergents, such as Alkylphenol polyglycol ethers can be used.
- active chlorine dispensers e.g. Hypochloride
- nonionic detergents such as Alkylphenol polyglycol ethers
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2929599 | 1979-07-21 | ||
DE19792929599 DE2929599A1 (de) | 1979-07-21 | 1979-07-21 | Mischungen von optischen aufhellern, deren herstellung und verwendung |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0023027A1 true EP0023027A1 (fr) | 1981-01-28 |
Family
ID=6076380
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP80104162A Withdrawn EP0023027A1 (fr) | 1979-07-21 | 1980-07-16 | Mélanges d'agents de blanchiment optique, leur préparation et leur utilisation |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP0023027A1 (fr) |
JP (1) | JPS5618654A (fr) |
AU (1) | AU6063780A (fr) |
BR (1) | BR8004481A (fr) |
DE (1) | DE2929599A1 (fr) |
ES (1) | ES493374A0 (fr) |
ZA (1) | ZA804366B (fr) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0032254A1 (fr) * | 1980-01-12 | 1981-07-22 | BASF Aktiengesellschaft | Procédé de préparation des bis-styrylbenzenes |
EP0238446A1 (fr) * | 1986-03-21 | 1987-09-23 | Ciba-Geigy Ag | Mélanges d'agents de blanchiment optique |
DE3802204A1 (de) * | 1987-01-29 | 1988-08-11 | Ciba Geigy Ag | Mischungen von optischen aufhellern |
US4778623A (en) * | 1979-12-13 | 1988-10-18 | Ciba-Geigy Corporation | Fluorescent brighteners consisting of bis-styrylbenzene compounds, a process for their preparation and their use |
WO1995008017A1 (fr) * | 1993-09-13 | 1995-03-23 | Basf Aktiengesellschaft | Melanges de blanchiment optique a base de composes bistyryle |
FR2732015A1 (fr) * | 1995-03-24 | 1996-09-27 | Basf Ag | Melanges d'agents de blanchiment optique a base de composes bisstyryliques |
CN1058976C (zh) * | 1996-12-31 | 2000-11-29 | 中国科学院感光化学研究所 | 一种荧光染料的合成方法 |
WO2001018301A1 (fr) * | 1999-09-06 | 2001-03-15 | Ciba Specialty Chemicals Holding Inc. | Melanges d'agents blanchissants fluorescents |
WO2001031111A1 (fr) * | 1999-10-25 | 2001-05-03 | Ciba Specialty Chemicals Holding Inc. | Melanges d'agents de blanchiment fluorescents |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS62130219A (ja) * | 1985-11-29 | 1987-06-12 | Nippon Steel Corp | 電磁鋼スラブの加熱方法 |
DE3764040D1 (de) * | 1986-07-01 | 1990-09-06 | Ciba Geigy Ag | 1,4-distryrylbenzolverbindungen und deren mischungen mit anderen 1,4-distryrylbenzolverbindungen. |
DE4219772A1 (de) * | 1992-06-17 | 1993-12-23 | Hoechst Ag | Mischungen aus 1,4-Bis-(cyanostyryl)-benzolen |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB913735A (en) * | 1959-06-24 | 1962-12-28 | Basf Ag | Optically brightened macromolecular organic substances |
CH389585A (de) * | 1959-08-12 | 1965-03-31 | Basf Ag | Verfahren zur Herstellung von Derivaten des 1,4-Bis-(styryl)-benzols |
FR1415977A (fr) * | 1963-10-31 | 1965-10-29 | Basf Ag | Procédé pour l'azurage optique de matériaux en polyesters et en polyamides synthétiques |
JPS5213522A (en) * | 1975-07-24 | 1977-02-01 | Nippon Kayaku Co Ltd | Preparation of styryls |
-
1979
- 1979-07-21 DE DE19792929599 patent/DE2929599A1/de not_active Withdrawn
-
1980
- 1980-07-15 ES ES493374A patent/ES493374A0/es active Granted
- 1980-07-16 EP EP80104162A patent/EP0023027A1/fr not_active Withdrawn
- 1980-07-17 JP JP9695280A patent/JPS5618654A/ja active Pending
- 1980-07-18 AU AU60637/80A patent/AU6063780A/en not_active Abandoned
- 1980-07-18 ZA ZA00804366A patent/ZA804366B/xx unknown
- 1980-07-18 BR BR8004481A patent/BR8004481A/pt unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB913735A (en) * | 1959-06-24 | 1962-12-28 | Basf Ag | Optically brightened macromolecular organic substances |
CH389585A (de) * | 1959-08-12 | 1965-03-31 | Basf Ag | Verfahren zur Herstellung von Derivaten des 1,4-Bis-(styryl)-benzols |
FR1415977A (fr) * | 1963-10-31 | 1965-10-29 | Basf Ag | Procédé pour l'azurage optique de matériaux en polyesters et en polyamides synthétiques |
JPS5213522A (en) * | 1975-07-24 | 1977-02-01 | Nippon Kayaku Co Ltd | Preparation of styryls |
Non-Patent Citations (1)
Title |
---|
CHEMICAL ABSTRACTS, Band 87, 1977, Seite 605, Nr. 22792h, Columbus, Ohio, (USA) & JP-A-52 013 522 (NIPPON KAYAKU CO. LTD) (01-02-1977) * |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5001253A (en) * | 1979-12-13 | 1991-03-19 | Ciba-Geigy Corporation | Fluorescent brighteners consisting of bis-styrylbenzene compounds, a process for their preparation and their use |
US4778623A (en) * | 1979-12-13 | 1988-10-18 | Ciba-Geigy Corporation | Fluorescent brighteners consisting of bis-styrylbenzene compounds, a process for their preparation and their use |
US4785128A (en) * | 1979-12-13 | 1988-11-15 | Ciba-Geigy Corporation | Process for the preparation of bis-styrylbenzenes |
EP0032254A1 (fr) * | 1980-01-12 | 1981-07-22 | BASF Aktiengesellschaft | Procédé de préparation des bis-styrylbenzenes |
EP0064303A1 (fr) * | 1980-01-12 | 1982-11-10 | BASF Aktiengesellschaft | Mélanges de biscyanostyrylbenzènes |
US4464284A (en) * | 1980-01-12 | 1984-08-07 | Basf Aktiengesellschaft | Mixtures of optical brighteners |
EP0238446A1 (fr) * | 1986-03-21 | 1987-09-23 | Ciba-Geigy Ag | Mélanges d'agents de blanchiment optique |
US4891153A (en) * | 1986-03-21 | 1990-01-02 | Ciba-Geigy Corporation | Mixtures of fluorescent whitening agents |
BE1000410A3 (fr) * | 1987-01-29 | 1988-11-22 | Ciba Geigy | Melanges d'azurants optiques, procede pour leur preparation, utilisation de ces melanges et produits les contenant. |
US4867906A (en) * | 1987-01-29 | 1989-09-19 | Ciba-Geigy Corporation | Mixtures of fluorescent whitening agents |
FR2611761A1 (fr) * | 1987-01-29 | 1988-09-09 | Ciba Geigy Ag | Melanges d'azurants optiques, procede pour leur preparation, utilisation de ces melanges et produits les contenant |
DE3802204A1 (de) * | 1987-01-29 | 1988-08-11 | Ciba Geigy Ag | Mischungen von optischen aufhellern |
WO1995008017A1 (fr) * | 1993-09-13 | 1995-03-23 | Basf Aktiengesellschaft | Melanges de blanchiment optique a base de composes bistyryle |
FR2732015A1 (fr) * | 1995-03-24 | 1996-09-27 | Basf Ag | Melanges d'agents de blanchiment optique a base de composes bisstyryliques |
CN1058976C (zh) * | 1996-12-31 | 2000-11-29 | 中国科学院感光化学研究所 | 一种荧光染料的合成方法 |
WO2001018301A1 (fr) * | 1999-09-06 | 2001-03-15 | Ciba Specialty Chemicals Holding Inc. | Melanges d'agents blanchissants fluorescents |
US6719922B1 (en) | 1999-09-06 | 2004-04-13 | Ciba Specialty Chemicals Corporation | Mixtures of fluorescent whitening agents |
WO2001031111A1 (fr) * | 1999-10-25 | 2001-05-03 | Ciba Specialty Chemicals Holding Inc. | Melanges d'agents de blanchiment fluorescents |
US6783698B1 (en) | 1999-10-25 | 2004-08-31 | Ciba Specialty Chemicals Corporation | Mixtures of fluorescent whitening agents |
Also Published As
Publication number | Publication date |
---|---|
ES8105053A1 (es) | 1981-05-16 |
DE2929599A1 (de) | 1981-02-05 |
AU6063780A (en) | 1981-01-22 |
ES493374A0 (es) | 1981-05-16 |
JPS5618654A (en) | 1981-02-21 |
BR8004481A (pt) | 1981-01-27 |
ZA804366B (en) | 1981-07-29 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
AK | Designated contracting states |
Designated state(s): AT BE CH DE FR GB IT NL SE |
|
17P | Request for examination filed |
Effective date: 19810423 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN |
|
18W | Application withdrawn |
Withdrawal date: 19820218 |
|
RIN1 | Information on inventor provided before grant (corrected) |
Inventor name: FRUEHBEIS, HORST, DR. Inventor name: ROESCH, GUENTER Inventor name: ERCKEL, RUEDIGER, DR. Inventor name: MARTINI, THOMAS, DR. |