EP0033018A2 - Mixtures of optical brighteners - Google Patents
Mixtures of optical brighteners Download PDFInfo
- Publication number
- EP0033018A2 EP0033018A2 EP80108264A EP80108264A EP0033018A2 EP 0033018 A2 EP0033018 A2 EP 0033018A2 EP 80108264 A EP80108264 A EP 80108264A EP 80108264 A EP80108264 A EP 80108264A EP 0033018 A2 EP0033018 A2 EP 0033018A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkoxy
- alkyl
- oder
- optionally substituted
- aralkyl
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 15
- 230000003287 optical effect Effects 0.000 title claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000460 chlorine Substances 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 125000005415 substituted alkoxy group Chemical group 0.000 claims abstract description 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 5
- 125000003435 aroyl group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 5
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims abstract description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 239000011737 fluorine Substances 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 6
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract description 3
- 150000002431 hydrogen Chemical class 0.000 abstract description 3
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 abstract 1
- -1 carbonyl ester Chemical class 0.000 abstract 1
- 238000002156 mixing Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 0 Cc1ccc(*)cc1 Chemical compound Cc1ccc(*)cc1 0.000 description 2
- 238000005282 brightening Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- GASGCPPLOGRXKN-UHFFFAOYSA-N C=CC(C=CCC1)=C1N Chemical compound C=CC(C=CCC1)=C1N GASGCPPLOGRXKN-UHFFFAOYSA-N 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
- 238000010521 absorption reaction Methods 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002195 synergetic effect Effects 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
- Residues Y and Z are in addition to hydrogen z.
- B OCH 3 , OC 2 H 5 , OC 3 H 7 , OC 4 H 9 , OC 2 H 4 OCH 3 , OC 2 H 4 OC 2 H 5 , OC 2 H 4 OC 3 H 7 , OC 2 H 4 OC 4 H 9 , OC 2 H 4 or OC 2 H 4 OC 2 H 4 OCH 3 .
- R The same alkoxy radicals and the following groups are to be mentioned for R: CH 3 , C 2 H 5 , C 3 H 7 , C 4 H 9 , C 5 H 11 , C 6 H 13 , C 8 H 17 , C 10 H 21 , , C 2 H 4 CN, CH 2 -CHO, CH 2 CN, C 2 H 4 COOCH 3 , CH 2 -COOC 2 H 5 , CH 2 -COOC 4 H 9 , C 2 H 4 Cl, C 2 H 4 OCH 3 , C 2 H 4 OC 2 H 4 OCH 3 , (CH 2 -CH 2 -O) 2 C 2 H 5 , (C 2 H 4 -O) 3 C 4 H 9 , C 2 H 4 SO 2 CH 3 , CH 2 COCH 3 , CH 2 C 6 H 5 or C 2 H 4 C 6 H 5 .
- the mixtures according to the invention are obtained either by jointly dispersing compounds of the formulas I and II in the stated mixing ratio or else by separate dispersing of the components and mechanical mixing.
- Preferred mixing ratios are in the range from 10 to 90% of compounds of the formula I.
- the optimum mixing ratio depends in each case on the type of the respective compounds of the brighteners mentioned under the formulas I and II. It can easily be determined by simple preliminary tests.
- the mixtures according to the invention are particularly suitable for optically brightening textile materials made of linear polyesters, polyamides and acetyl cellulose.
- the mixtures according to the invention can be applied to the textile material by known methods, for example by the exhaust process at 90-140 ° C. with or without addition of dyeing accelerators (carriers) or by the thermosol process at temperatures of 160-210 ° C.
- the mixtures according to the invention are distinguished by very favorable dyeing behavior.
- the advantage of the mixtures compared to the individual components can be seen in the fact that this gives an unexpected synergistic effect with regard to the degree of whiteness, i.e. mixtures according to the invention result in a higher degree of whiteness than would be expected when considering the proportions of the individual components. The same applies to the brilliance of the brightening.
- Preferred blending ratios are in the range of about 70-90: 30-10 (I: II) when high degrees of whiteness are desired and in the range of 30-60: 70-40 (I: II) when high lightfastness is required arrives.
- Polyester staple fiber fabric is washed as usual, dried and impregnated on a padder with an aqueous dispersion which contains 1 g / 1 of a mixture of the optical brighteners of the formula I. contains 90 parts I and 10 parts II in a mixing ratio.
- the material is then squeezed out so that there is a moisture absorption of 60%.
- the material thus sealed is then dried on a stenter frame at 100 ° C. for 2 minutes and then thermosolated at 190 ° C. for 30 seconds.
- the whiteness of the lightened textile material determined according to Berger is 134.
- Polyester fiber fabric is treated as described in Example 1 with an aqueous dispersion containing 1 g / 1 of a mixture of the optical brighteners of the formula I. and contains.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Detergent Compositions (AREA)
- Coloring (AREA)
Abstract
Die Erfindung betrifft Mischungen zweier oder mehrerer optischer Aufheller, enthaltend 5 bis 95 % von Verbindungen der allgemeinen Formel I
- n die Zahlen 1, 2 oder 3,
- Y Wasserstoff oder gegebenenfalls substituiertes Alkoxy,
- Z gegebenenfalls substituiertes Alkoxy,
- R gegebenenfalls substituiertes C1- bis C10 -Alkyl oder Alkoxy und die Reste
- X unabhängig voneinander Fluor, Chlor, Brom, Wasserstoff, C1- bis C10-Alkyl, Aralkyl, Aryl, Carbonester, gegebenenfalls substituiertes Carbamoyl oder Sulfamoyl, Alkyl-, Alkenyl-, Aralkyl- oder Aryl- sulfonyl, Alkanoyl, Aroyl oder Cyan bedeuten, mit der Maßgabe, daß für X = CN und n = 1 der Substituent X in meta-oder para-Stellung steht.
- n the numbers 1, 2 or 3,
- Y is hydrogen or optionally substituted alkoxy,
- Z optionally substituted alkoxy,
- R optionally substituted C 1 to C 10 alkyl or alkoxy and the radicals
- X independently of one another fluorine, chlorine, bromine, hydrogen, C 1 - to C 10 -alkyl, aralkyl, aryl, carbonyl ester, optionally substituted carbamoyl or sulfamoyl, alkyl, alkenyl, aralkyl or arylsulfonyl, alkanoyl, aroyl or cyan mean, with the proviso that for X = CN and n = 1 the substituent X is in the meta or para position.
Description
Die Erfindung betrifft Mischungen zweier oder mehrerer optischer Aufheller, enthaltend 5 bis 95 % von Verbindungen der allgemeinen Formel I
- n die Zahlen 1, 2 oder 3,
- Y Wasserstoff oder gegebenenfalls substituiertes Alkoxy,
- Z gegebenenfalls substituiertes Alkoxy,
- R gegebenenfalls substituiertes C1- bis C10-Alkyl oder Alkoxy und die Reste
- X unabhängig voneinander Fluor, Chlor, Brom,Wasserstoff, C1- bis C10-Alkyl, Aralkyl, Aryl, Carbonester, gegebenenfalls substituiertes Carbamoyl oder Sulfamoyl, Alkyl-, Alkenyl-, Aralkyl- oder Arylsulfonyl, Alkanoyl, Aroyl oder Cyan bedeuten, mit der Maßgabe, daß für X = CN und n = 1 der Substituent X in meta- oder para-Stellung steht.
- n the numbers 1, 2 or 3,
- Y is hydrogen or optionally substituted alkoxy,
- Z optionally substituted alkoxy,
- R optionally substituted C 1 to C 10 alkyl or alkoxy and the radicals
- X independently of one another are fluorine, chlorine, bromine, hydrogen, C 1 - to C 10 -alkyl, aralkyl, aryl, carboxylic esters, optionally substituted carbamoyl or sulfamoyl, alkyl, alkenyl, aralkyl or arylsulfonyl, alkanoyl, aroyl or cyano, with the proviso that for X = CN and n = 1 the substituent X is in the meta or para position.
Reste Y und Z sind neben Wasserstoff z. B. OCH3, OC2H5, OC3H7, OC4H9, OC2H4OCH3, OC2H4OC2H5, OC2H4OC3H7, OC2H4OC4H9, OC2H4 oder OC2H4OC2H4OCH3.Residues Y and Z are in addition to hydrogen z. B. OCH 3 , OC 2 H 5 , OC 3 H 7 , OC 4 H 9 , OC 2 H 4 OCH 3 , OC 2 H 4 OC 2 H 5 , OC 2 H 4 OC 3 H 7 , OC 2 H 4 OC 4 H 9 , OC 2 H 4 or OC 2 H 4 OC 2 H 4 OCH 3 .
Für R sind die gleichen Alkoxyreste sowie folgende Gruppen zu nennen: CH3, C2H5, C3H7, C4H9, C5H11, C6H13, C8H17, C10H21,
Reste X sind neben den bereits einzeln genannten beispielsweise: COOCH3, COOC2H5, COOC3H7, COOC4H9, COOC6H13, COOC8H17, COOC2H4OCH3,
Die erfindungsgemäßen Mischungen erhält man entweder durch gemeinsames Dispergieren von Verbindungen der Formeln I und II im angegebenen Mischungsverhältnis oder aber durch getrenntes Dispergieren der Komponenten und mechanisches Mischen. Bevorzugte Mischungsverhältnisse liegen im Bereich von 10 bis 90 % von Verbindungen der Formel I. Das optimale Mischungsverhältnis hängt im Einzelfall von der Art der jeweiligen Verbindungen der unter den Formeln I und II genannten Aufheller ab. Es läßt sich unschwer durch einfache Vorversuche ermitteln.The mixtures according to the invention are obtained either by jointly dispersing compounds of the formulas I and II in the stated mixing ratio or else by separate dispersing of the components and mechanical mixing. Preferred mixing ratios are in the range from 10 to 90% of compounds of the formula I. The optimum mixing ratio depends in each case on the type of the respective compounds of the brighteners mentioned under the formulas I and II. It can easily be determined by simple preliminary tests.
Die erfindungsgemäßen Mischungen eignen sich besonders zum optischen Aufhellen von Textilmaterialien aus linearen Polyestern, Polyamiden und von Acetylcellulose. Die erfindungsgemäßen Mischungen können nach bekannten Methoden auf das Textilgut appliziert werden, so beispielsweise nach dem Ausziehverfahren bei 90 - 140°C mit oder ohne Zusatz von Färbebeschleunigern (Carriern) oder nach dem Thermosolverfahren bei Temperaturen von 160 - 210°C.The mixtures according to the invention are particularly suitable for optically brightening textile materials made of linear polyesters, polyamides and acetyl cellulose. The mixtures according to the invention can be applied to the textile material by known methods, for example by the exhaust process at 90-140 ° C. with or without addition of dyeing accelerators (carriers) or by the thermosol process at temperatures of 160-210 ° C.
Die erfindungsgemäßen Mischungen zeichnen sich durch sehr günstiges färberisches Verhalten aus. Der Vorteil der Mischungen im Vergleich zu den Einzelkomponenten ist darin zu sehen, daß man damit einen unerwarteten synergistischen Effekt in Bezug auf den Weißgrad erhält, d.h., erfindungsgemäße Mischungen ergeben einen höheren Weißgrad als unter Berücksichtigung der Anteile der Einzelkomponenten zu erwarten wäre. Das gleiche gilt für die Brillanz der Aufhellungen.The mixtures according to the invention are distinguished by very favorable dyeing behavior. The advantage of the mixtures compared to the individual components can be seen in the fact that this gives an unexpected synergistic effect with regard to the degree of whiteness, i.e. mixtures according to the invention result in a higher degree of whiteness than would be expected when considering the proportions of the individual components. The same applies to the brilliance of the brightening.
Von besonderer Bedeutung sind Mischungen von Verbindungen der Formel I und II, bei denen
- X Cyan, Chlor, Carbonester oder Alkyl,
- R C1- bis C8-Alkyl oder Formyl-C1- bis C3-alkyl,
- Y Wasserstoff, C1- bis C4-Alkoxy oder C1- bis C4-Alkoxy-C1- bis C4-alkoxy und
- Z C1- bis C4-Alkoxy oder C1- bis C4-Alkoxy-C1- bis C4- alkoxy sind.
- X cyan, chlorine, carboxylic ester or alkyl,
- RC 1 to C 8 alkyl or formyl C 1 to C 3 alkyl,
- Y is hydrogen, C 1 to C 4 alkoxy or C 1 to C 4 alkoxy-C 1 to C 4 alkoxy and
- ZC 1 to C 4 alkoxy or C 1 to C 4 alkoxy-C 1 to C 4 alkoxy.
Bevorzugte Mischungsverhältnisse liegen im Bereich von ungefähr 70 - 90 : 30 - 10 (I : II), wenn hohe Weißgrade .erwünscht sind, und im Bereich von 30 - 60 : 70 - 40 (I : II), wenn es auf eine hohe Lichtechtheit ankommt.Preferred blending ratios are in the range of about 70-90: 30-10 (I: II) when high degrees of whiteness are desired and in the range of 30-60: 70-40 (I: II) when high lightfastness is required arrives.
In den folgenden Beispielen beziehen sich Angaben über Teile und Prozente, sofern nicht anders vermerkt, auf das Gewicht.In the following examples, parts and percentages are by weight unless otherwise noted.
Die Weißgrade wurden nach Berger (Die Farbe, 8 (1959), S 187 ff) gemessen.The degrees of whiteness were measured according to Berger (Die Farbe, 8 (1959), S 187 ff).
Polyesterstapelfasergewebe wird wie üblich gewaschen, getrocknet und auf einem Foulard mit einer wäßrigen Dispersion imprägniert, die 1 g/1 einer Mischung der optischen Aufheller der Formel I
Das Material wird dann so abgequetscht, daß sich eine Feuchtigkeitsaufnahme von 60 % ergibt. Das so geklotzte Material wird anschließend auf einem Spannrahmen 2 Minuten bei 100°C getrocknet und dann 30 sec bei 190°C thermosoliert. Der nach Berger ermittelte Weißgrad des so aufgehellten Textilmaterials beträgt 134.The material is then squeezed out so that there is a moisture absorption of 60%. The material thus sealed is then dried on a stenter frame at 100 ° C. for 2 minutes and then thermosolated at 190 ° C. for 30 seconds. The whiteness of the lightened textile material determined according to Berger is 134.
Wenn man Verbindungen der Formel I
Polyesterfasergewebe wird wie in Beispiel 1 beschrieben mit einer wäßrigen Dispersion behandelt, die 1 g/1 einer Mischung der optischen Aufheller der Formel I
Man erhält so eine brillante Weißaufhellung.This gives a brilliant white lightening.
Claims (3)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803001066 DE3001066A1 (en) | 1980-01-12 | 1980-01-12 | MIXTURES OF OPTICAL BRIGHTENERS |
| DE3001066 | 1980-01-12 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0033018A2 true EP0033018A2 (en) | 1981-08-05 |
| EP0033018A3 EP0033018A3 (en) | 1981-08-12 |
| EP0033018B1 EP0033018B1 (en) | 1985-04-10 |
Family
ID=6091980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP80108264A Expired EP0033018B1 (en) | 1980-01-12 | 1980-12-31 | Mixtures of optical brighteners |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0033018B1 (en) |
| JP (1) | JPS56104981A (en) |
| DE (2) | DE3001066A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0252009A1 (en) * | 1986-07-01 | 1988-01-07 | Ciba-Geigy Ag | 1,4-Distyryl benzene compounds and their mixtures with other 1,4-distyryl benzene compounds |
| WO1999005356A1 (en) * | 1997-07-25 | 1999-02-04 | Clariant Gmbh | Mixtures of optical brighteners |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2929591A1 (en) * | 1979-07-21 | 1981-02-05 | Hoechst Ag | MIXTURES OF OPTICAL BRIGHTENERS |
-
1980
- 1980-01-12 DE DE19803001066 patent/DE3001066A1/en not_active Withdrawn
- 1980-12-31 DE DE8080108264T patent/DE3070492D1/en not_active Expired
- 1980-12-31 EP EP80108264A patent/EP0033018B1/en not_active Expired
-
1981
- 1981-01-09 JP JP131081A patent/JPS56104981A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0252009A1 (en) * | 1986-07-01 | 1988-01-07 | Ciba-Geigy Ag | 1,4-Distyryl benzene compounds and their mixtures with other 1,4-distyryl benzene compounds |
| WO1999005356A1 (en) * | 1997-07-25 | 1999-02-04 | Clariant Gmbh | Mixtures of optical brighteners |
| US6120704A (en) * | 1997-07-25 | 2000-09-19 | Clariant Gmbh | Mixtures of optical brighteners |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0033018A3 (en) | 1981-08-12 |
| EP0033018B1 (en) | 1985-04-10 |
| JPS56104981A (en) | 1981-08-21 |
| DE3001066A1 (en) | 1981-07-16 |
| DE3070492D1 (en) | 1985-05-15 |
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