EP0035694B1 - Mélanges d'agents de blanchiment optique - Google Patents
Mélanges d'agents de blanchiment optique Download PDFInfo
- Publication number
- EP0035694B1 EP0035694B1 EP81101345A EP81101345A EP0035694B1 EP 0035694 B1 EP0035694 B1 EP 0035694B1 EP 81101345 A EP81101345 A EP 81101345A EP 81101345 A EP81101345 A EP 81101345A EP 0035694 B1 EP0035694 B1 EP 0035694B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- formula
- group
- phenyl
- 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.)
- Expired
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 20
- 230000003287 optical effect Effects 0.000 title claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 229910052717 sulfur Chemical group 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000011593 sulfur Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- -1 C1-C9 alkyl Chemical group 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 13
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 150000003254 radicals Chemical class 0.000 claims description 11
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 7
- 125000005605 benzo group Chemical group 0.000 claims description 7
- 125000004442 acylamino group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical group OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- 125000003106 haloaryl group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000005392 carboxamide group Chemical class NC(=O)* 0.000 claims 5
- 229940124530 sulfonamide Drugs 0.000 claims 4
- 150000003456 sulfonamides Chemical class 0.000 claims 4
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 1
- 125000005432 dialkylcarboxamide group Chemical group 0.000 claims 1
- 125000005208 trialkylammonium group Chemical group 0.000 claims 1
- 0 Cc1n[o]c(*)n1 Chemical compound Cc1n[o]c(*)n1 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000835 fiber Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000003857 carboxamides Chemical class 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical group FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000005227 alkyl sulfonate group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- HJMZMZRCABDKKV-UHFFFAOYSA-N carbonocyanidic acid Chemical compound OC(=O)C#N HJMZMZRCABDKKV-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- R 1 'and R 2 ' have the meaning given above for R 1 and R 2 .
- R 3 'and R 4 ' together are a fused phenyl ring or in the 5- and 7-position hydrogen or chlorine, alkyl, phenyl, X oxygen or sulfur and B 'a group of the formulas means, where R 6 'is alkyl, chloroalkyl, alkoxyalkyl, hydroxyalkyl or a group of the formula - (CH 2 CH 2 O) n -R, where n is 1, 2 or 3 and R is hydrogen or alkyl, R 11 ' 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, sulfonic acid, sulf
- R 3 "and R 4 " are hydrogen or alkyl
- n 1 or 0 and B " is a group of the formulas -CN or -COOalkyl and R s "means alkyl or methoxyethyl.
- R s is a group of the formulas -CN or -COOalkyl
- R s means alkyl or methoxyethyl.
- alkyl and alkoxy groups as well as other, derived groups of 1 to 4 carbon atoms.
- the compounds of formula 1 are from DE-PS 1 594 834 and the compounds of formula 2 known from DE-OS 2 709 924 and from the published Japanese patent applications Sho 51/40090 and Sho 70/4568.
- the mixing ratio for the individual components is between 1 and 99% by weight for the compound of the formula 1 and correspondingly 99 to 1% by weight for the other compound of the formula 2.
- These compounds of the formulas 1 and 2 can also be used individually can be used 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 50 to 99% by weight for the compound of the formula 1 and 50 to 1% by weight of the compound of the formula 2 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 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, whereby the optical brightener is completely fixed in the fiber. This gives an excellently brightened product with excellent light resistance and resistance to oxidizing and reducing agents, the degree of whiteness of the mixture being significantly higher than the degree of whiteness which can be achieved with the same amount of only one compound of formula 1 or 2.
- Fabric sections made of polyester staple fibers are washed, dried and impregnated on a foulard with aqueous dispersions which either contain only one brightener of formula 1 or 2 for comparison or a mixture of both brighteners in a weight ratio of 8 to 2 based on the active substance.
- the brighteners of formula 1 are taken from a commercially available dispersion (20% setting).
- the brighteners of formula 2 are used in a 10% dispersion in polyvinyl alcohol.
- the total amount of brightener is 1.66 g / l.
- the material is squeezed between rollers with a foulard so that there is a moisture absorption of approx. 80%.
- the material that has been sealed in this way is then dried at 110 ° C. and thermosolated on a tenter at the temperatures given in the table.
- the respective degrees of whiteness according to Ganz were obtained.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Detergent Compositions (AREA)
- Photoreceptors In Electrophotography (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Optical Fibers, Optical Fiber Cores, And Optical Fiber Bundles (AREA)
- Coloring (AREA)
Claims (5)
1. Mélanges d'azureurs optiques, mélanges caractérisés en ce qu'ils sont constitués:
a) de 1 à 99% en poids d'un ou plusieurs composés de formule 1:
dans laquelle
R1 et R2, qui peuvent être identiques ou différents, représentent chacun l'hydrogène ou un alkyle, et
b) de 99 à 1% en poids d'un ou plusieurs composés répondant à la formule 2:
dans laquelle
n est égal à 0 ou à 1,
X représente un atome d'oxygène ou de soufre,
R3 et R4 qui peuvent être identiques ou différents, représentent chacun un atome d'hydrogène, de fluor ou de chlore, un radical phényle, trifluorméthyle, alkyle an C1-C9, alcoxy, dialkylamino, acylamino, cyano, carboxy, alcoxycarbonyle, carbamoyle, sulfo, sulfamoyle ou alcoxysulfonyle, deux radicaux R3 et R4 voisins pouvent également former un noyau benzo ou représenter un radical alkylène inférieur ou un radical dioxa-1,3 propylène,
B représente un radical cyano, un radical -COORs ou un radical -CONR5R5 dans lesquels R5 représente l'hydrogène, un alkyle en C1-C18, un cycloalkyle, un aryle, un alkylaryle, un halogéno- aryle, un aralkyle, un alcoxyalkyle, un halogéno- alkyle, un hydroxyalkyle, un alkylamino-alkyle, un carboxyalkyle ou un alcoxycarbonylalkyle, deux radicaux alkyles ou alkylènes R5 portés par l'atome d'azote pouvant également former avec celui- ci un noyau de morpholine, de pipéridine ou de pipérazine, ou
B représente un radical répondant à l'une des formules suivantes:
dans lesquelles
Rs représente un radical alkyle, linéaire ou ramifié, contenant de 1 à 18 atomes de carbone, de préférence de 1 à 6, radical qui peut porter des groupes hydroxy, des atomes d'halogènes ou des radicaux alcoxy, dialkylamino, alkylthio, chlor- alkyloxy, aryloxy, arylthio ou aryles, les deux radicaux alkyles d'un radical dialkylaminoalkyle pouvant également former ensemble un noyau de morpholine, de pipéridine ou de pipérazine, ou R6 représente un radical -(CH2CH20)n-R dans lequel n est égal à 1 à 2 ou 3 et R représente l'hydrogène ou un radical alkyle, dialkylamino-alcoxyalkyle ou alkylthioalcoxyalkyle, les deux radicaux alkyles d'un radical dialkylamino-alcoxyalkyle pouvant également former ensemble un noyau de pipéridine, de pyrrolidine, de perhydro-azépine, de morpholine ou de pipérazine, ou R6 représente un radical répondant à la formule:
dans laquelle
Rg et R10 représentent chacun, indépendamment l'un de l'autre, l'hydrogène, un atome de fluor, un atome de chlore ou un radical phényle, alkyle, alcoxy, acylamino, cyano, carboxy, alcoxycarbonyle, carbamoyle, sulfo, sulfamoyle ou alcoxysulfonyle, deux radicaux Rg et R10 voisins pouvant également former ensemble un radical alkylène, un noyau benzo condensé ou un radical dioxa-1,3 propylène, R7 représente un atome d'hydrogène, un radical triphénylméthyle ou un radical alkyle inférieur éventuellement porteur d'un radical alkoxycarbonyle inférieur ou d'un radical carbamoyle, monoalkylcarbamoyle, dialkylcarb- amoyle, carboxy ou benzoyle, et
R8 représente un radical cyano ou un radical répondant à l'une des formules suivantes:
dans lesquelles
R', R" et R'" représentent chacun un atome d'hydrogène, un alkyle inférieur ou un phényle, les radicaux alkyles inférieurs pouvant porter des groupes hydroxy ou des radicaux alcoxy inférieurs, dialkylamino inférieurs ou trialkylammo- niums inférieurs et le radical phényle pouvant porter des atomes d'halogène ou des radicaux alkyles inférieurs ou alcoxy inférieurs, et
R" et R'" peuvent également former ensemble un radical bivalent saturé, Y représente O, S ou N-R, le symbole R désignant H ou un alkyle en C1-C4, ou
B représente un radical répondant à la formule:
dans laquelle
X représente un atome d'oxygène ou de soufre et R11 représente un noyau phényle éventuellement porteur d'un ou deux atomes de chlore, d'un ou deux radicaux alkyles ou alcoxyalkyles ou d'un radical phényle, cyano, carboxy, alcoxycarbonyle, carbamoyle, sulfo, sulfamoyle ou alcoxysulfonyle.
2. Mélanges d'azureurs optiques selon la revendication 1, caractérisés en ce qu'ils contiennent, comme composé de formule 1, un composé répondant à la formule:
dans laquell
R3' et R2' ont les significations qui ont été données pour R1 et R2 à la revendication 1.
3. Mélanges d'azureurs optiques selon la revendication 1, caractérisés en ce qu'ils contiennent, comme composé de formule 2, un composé répondant à la formule:
dans laquelle
R3' et R4' forment ensemble un noyau benzo condensé, ou, occupant les positions 5 et 7, représentent chacun l'hydrogène, le chlore, un alkyle ou un phényle, X représente l'oxygène ou le soufre et
B' représente un radical répondant à l'une des formules suivantes:
dans lesquelles
R6' représente un radical alkyle, chloralkyle, alcoxyalkyle ou hydroxyalkyle ou un radical -(CH2CH2O)n-R dans lequel, n est un nombre égal à 1, à 2 ou à 3 et R représente l'hydrogène ou un alkyle, R11' représente un radical phényle éventuellement porteur d'un ou deux atomes de chlore, d'un ou deux radicaux alkyles ou alcoxy alkyles, ou d'un radical phényle, cyano, carboxy, alcoxycarbonyle, carbamoyle, sulfo, sulfamoyle ou alcoxy sulfonyle, Ra' représente un radical cyano ou alcoxy carbonyle et R7' représente un radical alkyle.
4. Mélanges d'azureurs optiques selon la revendication 1, caractérisés en ce qu'ils contiennent, comme composé de formule 2, un composé répondant à la formule
dans laquelle
R3" et R4" représentent chacun l'hydrogène ou un radical alkyle, n est un nombre égal à 0 ou à 1 et B" représente un radical répondant à l'une des formules:
-CN et -COOAlkyle où R6" représente un radical alkyle ou méthoxyéthyle.
5. Mélanges d'azureurs optiques selon l'une quelconque des revendications 1 à 4, caractérisés en ce qu'ils contiennent de 50 à 99% en poids d'un composé de formule 1 et de 50 à 1 % en poids d'un composé de formule 2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT81101345T ATE4554T1 (de) | 1980-03-07 | 1981-02-25 | Mischungen von optischen aufhellern. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3008812 | 1980-03-07 | ||
| DE19803008812 DE3008812A1 (de) | 1980-03-07 | 1980-03-07 | Mischungen von optischen aufhellern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0035694A1 EP0035694A1 (fr) | 1981-09-16 |
| EP0035694B1 true EP0035694B1 (fr) | 1983-08-31 |
Family
ID=6096567
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP81101345A Expired EP0035694B1 (fr) | 1980-03-07 | 1981-02-25 | Mélanges d'agents de blanchiment optique |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4400294A (fr) |
| EP (1) | EP0035694B1 (fr) |
| JP (1) | JPS56141360A (fr) |
| AT (1) | ATE4554T1 (fr) |
| AU (1) | AU540524B2 (fr) |
| BR (1) | BR8101322A (fr) |
| CA (1) | CA1154910A (fr) |
| DE (2) | DE3008812A1 (fr) |
| PH (1) | PH19044A (fr) |
| ZA (1) | ZA811513B (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3027479A1 (de) * | 1980-07-19 | 1982-03-04 | Hoechst Ag, 6000 Frankfurt | Mischungen von optischen aufhellern und deren verwendung |
| 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. |
| DK64690D0 (da) * | 1990-03-12 | 1990-03-12 | Ntp Elektronik A S | Omkoblingssystem |
| ES2145743T3 (es) * | 1990-12-28 | 2000-07-16 | Teijin Ltd | Compuesto de anillo condensado benzoxa, su produccion y composicion farmaceutica que lo contiene. |
| DE19732109A1 (de) * | 1997-07-25 | 1999-01-28 | Clariant Gmbh | Mischungen von optischen Aufhellern |
| US20180320098A1 (en) | 2015-11-30 | 2018-11-08 | Sabic Global Technologies B.V. | Process for enhancing gasoline octane boosters, gasoline boosters, and gasolines |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2390537A1 (fr) * | 1977-05-11 | 1978-12-08 | Hoechst Ag | Melanges d'azureurs optiques derivant du stilbene |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1955310A1 (de) * | 1969-11-04 | 1971-05-13 | Hoechst Ag | Verwendung von waessrigen Dispersionen von Mischungen aus Benzoxazol- und Phenyloxazolderivaten zum optischen Aufhellen |
| US4105399A (en) * | 1973-09-05 | 1978-08-08 | Ciba-Geigy Corporation | Optically brightening with a synergistic mixture |
| CH598309A5 (fr) * | 1974-08-14 | 1978-04-28 | Ciba Geigy Ag | |
| JPS5140090A (ja) * | 1974-09-30 | 1976-04-03 | Toyoda Chuo Kenkyusho Kk | Choonpahatsuseisochi |
| ES456483A0 (es) * | 1976-03-09 | 1978-02-16 | Hoechst Ag | Procedimiento para la preparacion de compuestos de estilbeno. |
| CH623705GA3 (en) * | 1976-03-09 | 1981-06-30 | Process for the preparation of stilbene compounds and their use as optical brighteners | |
| LU78483A1 (de) * | 1977-11-10 | 1979-06-13 | Ciba Geigy Ag | Verfahren zur herstellung von benzoxazolyl-phenylstilbenen |
-
1980
- 1980-03-07 DE DE19803008812 patent/DE3008812A1/de not_active Withdrawn
-
1981
- 1981-02-25 EP EP81101345A patent/EP0035694B1/fr not_active Expired
- 1981-02-25 DE DE8181101345T patent/DE3160803D1/de not_active Expired
- 1981-02-25 AT AT81101345T patent/ATE4554T1/de not_active IP Right Cessation
- 1981-03-05 PH PH25321A patent/PH19044A/en unknown
- 1981-03-06 ZA ZA00811513A patent/ZA811513B/xx unknown
- 1981-03-06 CA CA000372440A patent/CA1154910A/fr not_active Expired
- 1981-03-06 JP JP3140181A patent/JPS56141360A/ja active Granted
- 1981-03-06 BR BR8101322A patent/BR8101322A/pt unknown
- 1981-03-06 AU AU68142/81A patent/AU540524B2/en not_active Expired - Fee Related
-
1982
- 1982-11-08 US US06/439,946 patent/US4400294A/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2390537A1 (fr) * | 1977-05-11 | 1978-12-08 | Hoechst Ag | Melanges d'azureurs optiques derivant du stilbene |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3160803D1 (en) | 1983-10-06 |
| JPS56141360A (en) | 1981-11-05 |
| JPH0153303B2 (fr) | 1989-11-13 |
| BR8101322A (pt) | 1981-09-08 |
| ZA811513B (en) | 1982-03-31 |
| AU540524B2 (en) | 1984-11-22 |
| CA1154910A (fr) | 1983-10-11 |
| PH19044A (en) | 1985-12-11 |
| EP0035694A1 (fr) | 1981-09-16 |
| DE3008812A1 (de) | 1981-09-24 |
| ATE4554T1 (de) | 1983-09-15 |
| AU6814281A (en) | 1981-09-10 |
| US4400294A (en) | 1983-08-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0023028B1 (fr) | Mélanges d'agents de blanchiment optiques et leur utilisation | |
| DE2721084A1 (de) | Mischungen von optischen aufhellern | |
| EP0023026B1 (fr) | Mélanges d'agents de blanchiment optiques et leur utilisation | |
| EP0035694B1 (fr) | Mélanges d'agents de blanchiment optique | |
| DE2163003A1 (de) | Textilbehandlungslösung | |
| EP0044996B1 (fr) | Mélanges d'azureurs optiques | |
| DE2629703C3 (de) | Aufhellermischungen und deren Verwendung | |
| DE2743127A1 (de) | Verfahren zum flammfestmachen von synthetischem fasermaterial | |
| DE4128638B4 (de) | Wäßrige Dispersionen von flammhemmenden Verbindungen | |
| EP0058880B1 (fr) | Mélanges d'azurants optiques | |
| DE19732109A1 (de) | Mischungen von optischen Aufhellern | |
| CH628677A5 (de) | Verfahren zur herstellung von stabilen waessrigen aufhellerdispersionen. | |
| DE1419003A1 (de) | Optisch aufhellende Mischungen | |
| EP0240461A1 (fr) | Mélanges d'agents de blanchiment optique | |
| DE2759217A1 (de) | Mischungen von optischen aufhellern | |
| DE1802642A1 (de) | Fluoreszierende 1-(Pyrazolinylphenylsulfonyl)-piperazine | |
| DE2712408A1 (de) | Neue 3-phenyl-7-(v-triazol-2-yl)-cumarine | |
| DE3102401C2 (fr) | ||
| DE1029792B (de) | Optische Aufhellungsmittel | |
| EP0242335B1 (fr) | Mélanges d'agents de blanchiment optique | |
| DE1007726B (de) | Appreturmasse fuer Textilien | |
| DE1719005C3 (de) | 2-(4'-Carboxystyryl)-benzoxazolderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als optische Aufheller | |
| DE929144C (de) | Waschmittel | |
| DE1670722B2 (de) | l-[4'-(ß- AcylaminoäthylsulfonyO-phenyl] -3-aryl-A2 -pyrazoline, Verfahren zu ihrer Herstellung und Verwendung als optische Aufhellungsmittel | |
| EP0033018A2 (fr) | Mélanges d'agents de blanchiment optique |
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: 19811009 |
|
| ITF | It: translation for a ep patent filed | ||
| GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
| AK | Designated contracting states |
Designated state(s): AT BE CH DE FR GB IT LI NL SE |
|
| REF | Corresponds to: |
Ref document number: 4554 Country of ref document: AT Date of ref document: 19830915 Kind code of ref document: T |
|
| REF | Corresponds to: |
Ref document number: 3160803 Country of ref document: DE Date of ref document: 19831006 |
|
| ET | Fr: translation filed | ||
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: FR Payment date: 19840116 Year of fee payment: 4 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: AT Payment date: 19840118 Year of fee payment: 4 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: SE Payment date: 19840331 Year of fee payment: 4 Ref country code: BE Payment date: 19840331 Year of fee payment: 4 |
|
| PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |
|
| 26N | No opposition filed | ||
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: NL Payment date: 19850114 Year of fee payment: 5 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: AT Effective date: 19850225 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SE Effective date: 19850226 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: NL Effective date: 19860901 |
|
| NLV4 | Nl: lapsed or anulled due to non-payment of the annual fee | ||
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: GB Effective date: 19890225 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: BE Effective date: 19890228 |
|
| BERE | Be: lapsed |
Owner name: HOECHST A.G. Effective date: 19890228 |
|
| GBPC | Gb: european patent ceased through non-payment of renewal fee | ||
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: FR Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 19891027 |
|
| REG | Reference to a national code |
Ref country code: FR Ref legal event code: ST |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: DE Payment date: 19910417 Year of fee payment: 11 |
|
| PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: CH Payment date: 19910418 Year of fee payment: 11 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: LI Effective date: 19920229 Ref country code: CH Effective date: 19920229 |
|
| REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DE Effective date: 19921103 |
|
| EUG | Se: european patent has lapsed |
Ref document number: 81101345.7 Effective date: 19860129 |