EP0060439A2 - Masse de filage pour la fabrication de fibres en cellulose régénérée et contenant un azurant optique - Google Patents

Masse de filage pour la fabrication de fibres en cellulose régénérée et contenant un azurant optique Download PDF

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Publication number
EP0060439A2
EP0060439A2 EP82101612A EP82101612A EP0060439A2 EP 0060439 A2 EP0060439 A2 EP 0060439A2 EP 82101612 A EP82101612 A EP 82101612A EP 82101612 A EP82101612 A EP 82101612A EP 0060439 A2 EP0060439 A2 EP 0060439A2
Authority
EP
European Patent Office
Prior art keywords
formula
water
brightener
hydroxy
spinning
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
Application number
EP82101612A
Other languages
German (de)
English (en)
Other versions
EP0060439B1 (fr
EP0060439A3 (en
Inventor
Udo Dr. Eckstein
Reinhold Dr. Hörnle
Jochen Koll
Hans-Heinz Dr. Mölls
Günter Schäfer
Hans Dr. Theidel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=6127233&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0060439(A2) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Bayer AG filed Critical Bayer AG
Priority to AT82101612T priority Critical patent/ATE11434T1/de
Publication of EP0060439A2 publication Critical patent/EP0060439A2/fr
Publication of EP0060439A3 publication Critical patent/EP0060439A3/de
Application granted granted Critical
Publication of EP0060439B1 publication Critical patent/EP0060439B1/fr
Expired legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
    • D01F2/06—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from viscose
    • D01F2/08—Composition of the spinning solution or the bath
    • D01F2/16—Addition of dyes to the spinning solution
    • 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

Definitions

  • the dyes used are subject to a wide variety of chemical stresses, which are not found in any other dyeing process in this unusual combination.
  • the dyes have to be highly acid and alkali resistant in order to survive the treatment in the various spinning baths undamaged.
  • Suitable heterocycles which can be formed by 2 of the radicals R 2 -R 3 are saturated 5- or 6-membered types, such as morpholine, piperidine, pyrrolidine and others
  • Suitable heterocycles which can be formed by 3 of these radicals are saturated types, in particular pyridine.
  • Suitable alkyl radicals are in particular those with 1-20 C atoms which can be substituted by CN, OH, halogen, C 1 -C 4 alkoxy or C 1 -C 4 alkylcarbonylamino.
  • Suitable alkenyl radicals are in particular those with 2 to 10 carbon atoms.
  • Suitable aralkyl radicals are phenyl-C 1 -C 3 -alkyl radicals.
  • Suitable aryl radicals are phenyl radicals which g by halo en, C may be substituted 1 -C 4 alkyl or C 1 -C 4 alkoxy.
  • Suitable cycloalkyl radicals are especially cyclohexyl radicals.
  • Halogen is preferably understood to mean Cl and Br.
  • Suitable cellulose whiteners from which the radical A is derived, are bistriazolylstilbene, bistilbene and especially bistriazinylaminostilbene disulfonic acids.
  • optical brighteners according to the formulas II-IV as sulfonic acids or their water-soluble salts, in particular their alkali salts, with low molecular weight basic nitrogen compounds of the formula V where Y is a colorless, non-fluorescent anion or OH (-) .
  • the reaction takes place in water and / or organic solvents, such as methanol, ethanol, propanol, isopropanol, butanol, glycol, glycol methyl ether, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, sulfolane, hexamethylphosphoric triamide at temperatures from 20 ° C. to the reflux temperature of the corresponding solvent.
  • organic solvents such as methanol, ethanol, propanol, isopropanol, butanol, glycol, glycol methyl ether, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, sulfolane, hexamethylphosphoric triamide
  • the poorly soluble brightener salts obtained in this way can be used as brightening agents directly or after prior fine grinding or liquid formation.
  • the dispersions according to the invention can be prepared as follows:
  • the press cakes and / or powders are homogenized with vigorous stirring after the addition of a surface-active substance and optionally water.
  • the amount of the surface-active substance can then be increased, if necessary to the total amount required for the stability of the dispersion.
  • the suspension obtained is then comminuted and wet-ground.
  • Pre-shredding can be carried out using stone or tooth colloid mills.
  • the subsequent wet comminution can be carried out in colloidal vibratory, cone and vibromills as well as in dissolvers or in sub-micron dispersers.
  • continuous agitator mills with grinding media preferably those made of SiO 2 with a diameter of 0.2-5 mm, are preferably used.
  • surface-active substances or hydrotropic substances such as e.g. Ethylene glycol or glycerin, preservatives, wetting agents, defoamers and / or water are added, unless this has been done at an earlier point in time e.g. before grinding.
  • the complete reaction of the brightener salts II-IV with the basic nitrogen compounds V takes place in the grinder, preferably in a continuous agitator mill with Sio 2 grinding media.
  • Suitable surface-active substances are all customary, cationic and nonionic surface-active substances, as are described, for example, in DE-OS 2 334 769, pages 8-10 (corresponds to GB-PS 1 417 071).
  • Nonionic surfactants are preferably used.
  • the compounds of formula (I) show a more or less pronounced fluorescence in the dissolved or finely divided state. They are suitable for whitening natural and synthetic spinning masses, especially regenerated cellulose fibers such as rayon and rayon, which can be processed into woven and non-woven materials (nonwovens). They are also suitable for lightening plastics such as polyvinyl chloride, polyethylene and polycarbonate, as well as paper coating slips.
  • the amount of the compounds I used depends on the desired lightening effect. In general, 0.01-0.5% by weight of pure active substance (based on the fiber material to be lightened) is sufficient.
  • the brightener of the formula (1) is reacted with 7.5 g of benzyldimethylphenylammonium chloride in the same way as described in Example 1. This gives 12.2 g of light yellow crystals with a melting point of 259-260 ° C., which can be recrystallized from ethylene glycol.
  • the substance is practically insoluble in water and shows excellent white effects when incorporated into viscose.
  • Brightener of the formula are refluxed with 10 g of benzyl-dodecyl-dimethylammonium chloride in 120 ml of dimethylformamide for 2 hours and, after cooling to 10 ° C., are filtered off. 8.7 g of light yellow crystals of mp: 182-184 ° C. are obtained, which can be recrystallized from ethylene glycol.
  • Brighteners of formula 1 from Example 1 are homogenized with 12.8 g of benzyldimethylphenylammonium chloride, 16 g of emulsifier W and 55.2 g of water with stirring and pre-comminuted with a toothed colloid mill.
  • the suspension is wet crushed at room temperature and 4 passes in a bead mill.
  • the resulting stable dispersion is easy to incorporate into the spinning mass and shows excellent white effects on the spun fiber.
  • 16 g of the optical brightener of the formula I from Example 1 are homogenized with 16 g of benzyl-dodecyl-dimethyl-ammonium chloride, 16 g of emulsifier W and 52 g of water with stirring and pre-comminuted with a toothed colloid mill.
  • the suspension is wet comminuted in a bead mill at room temperature with 4 passes.
  • Example 8 In the same manner as in Examples 10 - 11 and described, also the starting materials (8) described in Example 8 blank - (20) reacting to and form stable dispersions.
  • a comparison of the brightening with equivalent amounts of the starting compound (1) shows that higher whiteness levels are obtained with the quaternary ammonium salt precipitated.
  • the corresponding amount of the pure active ingredient from Example 1 can also be used and spun in the same way.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Detergent Compositions (AREA)
  • Artificial Filaments (AREA)
  • Coloring (AREA)
EP82101612A 1981-03-14 1982-03-03 Masse de filage pour la fabrication de fibres en cellulose régénérée et contenant un azurant optique Expired EP0060439B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT82101612T ATE11434T1 (de) 1981-03-14 1982-03-03 Weisstoenerhaltige spinnmassen zur herstellung von celluloseregeneratfasern.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19813109828 DE3109828A1 (de) 1981-03-14 1981-03-14 Weisstoenerhaltige spinnmassen zur herstellung von celluloseregeneratfasern
DE3109828 1981-03-14

Publications (3)

Publication Number Publication Date
EP0060439A2 true EP0060439A2 (fr) 1982-09-22
EP0060439A3 EP0060439A3 (en) 1983-06-29
EP0060439B1 EP0060439B1 (fr) 1985-01-23

Family

ID=6127233

Family Applications (1)

Application Number Title Priority Date Filing Date
EP82101612A Expired EP0060439B1 (fr) 1981-03-14 1982-03-03 Masse de filage pour la fabrication de fibres en cellulose régénérée et contenant un azurant optique

Country Status (4)

Country Link
EP (1) EP0060439B1 (fr)
AT (1) ATE11434T1 (fr)
BR (1) BR8201336A (fr)
DE (2) DE3109828A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11130975A (ja) * 1997-10-29 1999-05-18 Hakkooru Chemical Kk 隠ぺい性の優れた蛍光性有機白色顔料組成物
US7270771B2 (en) * 2002-07-05 2007-09-18 Ciba Specialty Chemicals Corporation Triazinylaminostilbene disulphonic acid mixtures

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1096321B (de) * 1954-08-07 1961-01-05 Bayer Ag Aufhellungsmittel
DE1245032B (de) * 1963-05-11 1967-07-20 Hoechst Ag Verfahren zur Herstellung gefaerbter Gebilde
CH449843A (de) * 1964-09-15 1968-01-15 Ciba Geigy Verfahren zur Herstellung optisch aufgehellter Formkörper aus regenerierter Cellulose
DE1594846A1 (de) * 1966-07-28 1971-05-27 Hoechst Ag Lagerbestaendige Aufhellerloesung

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1096321B (de) * 1954-08-07 1961-01-05 Bayer Ag Aufhellungsmittel
DE1245032B (de) * 1963-05-11 1967-07-20 Hoechst Ag Verfahren zur Herstellung gefaerbter Gebilde
CH449843A (de) * 1964-09-15 1968-01-15 Ciba Geigy Verfahren zur Herstellung optisch aufgehellter Formkörper aus regenerierter Cellulose
DE1594846A1 (de) * 1966-07-28 1971-05-27 Hoechst Ag Lagerbestaendige Aufhellerloesung

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11130975A (ja) * 1997-10-29 1999-05-18 Hakkooru Chemical Kk 隠ぺい性の優れた蛍光性有機白色顔料組成物
US6488867B1 (en) * 1997-10-29 2002-12-03 Hakkol Chemical Co., Ltd. Organic fluorescent whitening pigment composition having an excellent hiding power
US7270771B2 (en) * 2002-07-05 2007-09-18 Ciba Specialty Chemicals Corporation Triazinylaminostilbene disulphonic acid mixtures

Also Published As

Publication number Publication date
BR8201336A (pt) 1983-01-25
EP0060439B1 (fr) 1985-01-23
DE3261994D1 (en) 1985-03-07
DE3109828A1 (de) 1982-09-23
ATE11434T1 (de) 1985-02-15
EP0060439A3 (en) 1983-06-29

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