DE1418756C3 - Use of certain compounds as light stabilizers for cellulose and cellulose diacetate. Eliminated from: 1116393 - Google Patents

Use of certain compounds as light stabilizers for cellulose and cellulose diacetate. Eliminated from: 1116393

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Publication number
DE1418756C3
DE1418756C3 DE19591418756 DE1418756A DE1418756C3 DE 1418756 C3 DE1418756 C3 DE 1418756C3 DE 19591418756 DE19591418756 DE 19591418756 DE 1418756 A DE1418756 A DE 1418756A DE 1418756 C3 DE1418756 C3 DE 1418756C3
Authority
DE
Germany
Prior art keywords
cellulose
light
substances
cyanuric chloride
cyanuric
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
Application number
DE19591418756
Other languages
German (de)
Other versions
DE1418756A1 (en
DE1418756B2 (en
Inventor
Guenther Dipl.-Chem.Dr. 7821 Kappel Cordes
Arnulf Dr. 7800 Freiburg Sippel
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.)
Deutsche Rhodiaceta AG
Original Assignee
Deutsche Rhodiaceta 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
Application filed by Deutsche Rhodiaceta AG filed Critical Deutsche Rhodiaceta AG
Publication of DE1418756A1 publication Critical patent/DE1418756A1/en
Publication of DE1418756B2 publication Critical patent/DE1418756B2/en
Application granted granted Critical
Publication of DE1418756C3 publication Critical patent/DE1418756C3/en
Expired legal-status Critical Current

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Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/35Heterocyclic compounds
    • D06M13/355Heterocyclic compounds having six-membered heterocyclic rings
    • D06M13/358Triazines
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08BPOLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B15/00Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
    • C08B15/05Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur
    • C08B15/06Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur containing nitrogen, e.g. carbamates
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08BPOLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B3/00Preparation of cellulose esters of organic acids
    • C08B3/22Post-esterification treatments, including purification

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biochemistry (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Coloring (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Cosmetics (AREA)

Description

Unter reaktionsfähigen, UV-Licht absorbierenden 90 g Cellulosediacetat werden in 800 ml Aceton georganischen Verbindungen sind hierbei Verbindungen löst. Hierzu wird eine Lösung von 1,52 g 2,4-Dichlorwie Polyoxybenzophenone, Azomalonester, Salicyl- 6-(3-oxy-4-benzoyl-phenoxy)-triazin und 0,77 g Pyrisäureester oder substituierte Aminodiphenyle zu ver- din in 100 ml Aceton gegeben, 3 Stunden unter stehen (vergleiche u. a. USA.-Patentschrift 2 716 071, 40 Rühren zum Rückfluß erhitzt und das Reaktionsschweizerische Patentschrift 350 763, Ind. Eng. Chem. produkt langsam unter mäßigem Rühren in 3 1 Wasser 43 [1951] S. 1585). von etwa 700C ausgefällt. Das so erhaltene ProduktUnder reactive, UV-absorbing 90 g of cellulose diacetate, organic compounds are dissolved in 800 ml of acetone. For this purpose, a solution of 1.52 g of 2,4-dichloro such as polyoxybenzophenones, azomalone esters, salicyl 6- (3-oxy-4-benzoyl-phenoxy) -triazine and 0.77 g of pyric acid esters or substituted aminodiphenyls are converted into 100% ml of acetone given, stand for 3 hours (see, inter alia, USA.-Patent 2 716 071, 40 stirring heated to reflux and the reaction Swiss patent 350 763, Ind. Eng. Chem. product slowly with moderate stirring in 3 l of water 43 [1951] P. 1585). of about 70 0 C precipitated. The product thus obtained

Bei der Herstellung der erfindungsgemäß zu ver- wird 15 Stunden unter fließendem Wasser ausgewendenden Verbindungen verliert die Lichtschutz- waschen und nach Trocknen versponnen. Der Gehalt 1J* wirkung des organischen Substituenten des Cyanur- 45 an lichtschutzwirksamer Substanz wird kolorimetrisch :hlorids nicht an Wirksamkeit. Bei der Verwendung in Aceton mit Eisen(III)-chlorid bestimmt und beselbst reagiert das substituierte Cyanurchlorid mit trägt 0,8 %, berechnet auf 2,4-Dioxy-benzophenon als meinem beweglichen Chloratom mit einem aktiven wirksame Substanz.In the production of the compounds to be used in accordance with the invention for 15 hours under running water, the light protection wash is lost and spun after drying. The content of 1 J * effect of the organic substituents of the cyanuric 45 in light-protective substance is colorimetrically: chloride is not effective. When used in acetone with iron (III) chloride, the substituted cyanuric chloride reacts with 0.8%, calculated on 2,4-dioxy-benzophenone as my mobile chlorine atom, with an active substance.

Wasserstoffatom der Cellulose unter Halogenwasser- Unter den gleichen Bedingungen wird Cellulose-Hydrogen atom of cellulose under halogenated water- Under the same conditions, cellulose-

;toff-Abspaltung, und es erfolgt eine chemische Bin- 50 diacetat mit 2,4-Dioxybenzophenon behandelt. Die Jung des Lichtschutzmittels im Grundmolekül der Analyse des in gleicher Weise ausgewaschenen Pro-Cellulose oder des Cellulosediacetats. duktes ergibt lediglich einen Gehalt von 0,4% 2,4-Di-; toff cleavage, and a chemical bond takes place 50 diacetate treated with 2,4-dioxybenzophenone. the Jung of the sunscreen agent in the basic molecule of the analysis of the pro-cellulose washed out in the same way or cellulose diacetate. product results in a content of only 0.4% 2,4-di-

Es ist an sich bekannt, daß ein Teil der sogenannten oxybenzophenon.It is known per se that part of the so-called oxybenzophenone.

Claims (1)

1 2 1 2 Reaktivfarbstoffe dadurch hergestellt wird, daß an denReactive dyes is produced in that the Patentanspruch: Farbstoff durch Umsetzung mit Cyanurchlorid einClaim: dye by reaction with cyanuric chloride Triazin-Ring mit mindestens einem noch aktivenTriazine ring with at least one still active Verwendung von Verbindungen, die durch Um- Halogenatom gekoppelt wird. Weiterhin sind Verbinsetzung von reaktionsfähigen, UV-Licht absor- 5 düngen von Cellulose mit Substanzen, die die Gruppe bierenden organischen Verbindungen mit Cyanur- N — C-Halogen besitzen, wie z. B. Cyanurchlorid, chlorid hergestellt worden sind, als Lichtschutz- Cyanurbromid, Dichlorchinazolin, Dichlorphthalazin, mittel für Cellulose und für Cellulosediacetat. bekannt. Es war jedoch nicht vorauszusehen, daß eineUse of compounds that are coupled by Um halogen atom. There are also connections of reactive, UV light absor- 5 fertilize cellulose with substances that make up the group Bieren organic compounds with cyanuric N - C halogen, such. B. cyanuric chloride, chloride, as light protection cyanuric bromide, dichloroquinazoline, dichlorophthalazine, agent for cellulose and for cellulose diacetate. known. It was not foreseeable, however, that one Verknüpfung von als Lichtschutzmittel in Frage ίο kommenden organischen Verbindungen mit Cyanur-Linking of organic compounds suitable as light stabilizers with cyanuric chlorid fast keine Einwirkung auf die Absorptionskurve eines das ultraviolette Licht absorbierenden Stoffes hat, selbst dann nicht, wenn man das Produkt unter Halogenwasserstoff-Abspaltung an Cellulose-Seit längerer Zeit ist eine große Anzahl organischer 15 diacetat bindet.chloride has almost no effect on the absorption curve of an ultraviolet light absorbent Substance, even if the product is split off from the cellulose side by splitting off hydrogen halide longer time is a large number of organic 15 diacetate binds. Substanzen bekannt, die als Zusatz zu Cellulose und Untersuchungen mit einem Spektralphotometer er-Known substances that are used as additives to cellulose and investigations with a spectrophotometer Cellulosederivaten deren Lichtbeständigkeit verbessern gaben nahezu gleichbleibende Absorptionskurven für sollen. In den meisten Fällen handelt es sich bei diesen z. B. mit 2,4-Dioxybenzophenon behandeltes sekun-Lichtschutzstoffen um Verbindungen, die ultraviolette däres Celluloseacetat und für sekundäres Cellulose-Strahlen absorbieren; es sind jedoch auch Substanzen so acetat, das mit der entsprechenden Menge 2,4-DichIorbekannt, die Schutzwirkung besitzen, ohne ultra- 6-(3-oxy-4-benzoyl-phenoxy)-triazin umgesetzt wurde, violette Strahlen zu absorbieren. so daß beide Proben die gleichen Mengen wirksamer -Cellulose derivatives whose light resistance improve gave almost constant absorption curves for should. In most cases, these are z. B. treated with 2,4-dioxybenzophenone secun light protection substances to compounds containing ultraviolet däres cellulose acetate and for secondary cellulose rays absorb; However, there are also substances such as acetate that is known with the corresponding amount of 2,4-dichloro, have the protective effect without using ultra- 6- (3-oxy-4-benzoyl-phenoxy) -triazine, absorb violet rays. so that both samples use the same amounts more effectively - Die meisten der als Lichtschutzmittel bekannten Substanz, berechnet als 2,4-Dioxybenzophenon, ent- ** Stoffe zeigen den Nachteil, daß sie zunächst wirksam hielten.Most of the substance known as a light stabilizer, calculated as 2,4-dioxybenzophenone, Substances have the disadvantage that they were initially effective. sind, jedoch, wenn die betreffenden Cellulosen oder 35 Beispielare, however, if the celluloses in question or 35 example Cellulosederivate beispielsweise in Textilfasern um- „ .Cellulose derivatives, for example, in textile fibers. gewandelt sind, schon durch wenige Waschen so weit a) Herstellung des zu verwendenden Lichtschutz-have changed, just a few washes so far a ) Production of the light protection to be used herausgewaschen werden, daß keine Lichtschutz- mittelsbe washed out that no sunscreen agents wirkung mehr feststellbar ist. Äquivalente Mengen 2,4-Dioxybenzophenon undeffect is more noticeable. Equivalent amounts of 2,4-dioxybenzophenone and Gegenstand der Erfindung ist die Verwendung von 30 Cyanurchlorid werden in Eiswasser in Gegenwart einer Verbindungen, die durch Umsetzung von reaktions- äquivalenten Menge Natriumhydroxyd zur Reaktion fähigen, UV-Licht absorbierenden organischen Ver- gebracht; das 2,4-Dichlor-6-(3-oxy-4-benzoyl-phenbindungen mit Cyanurchlorid hergestellt worden sind, oxy)-triazin fällt als farblose Substanz aus.The invention relates to the use of 30 cyanuric chloride in ice water in the presence of a Compounds obtained by converting an equivalent amount of sodium hydroxide into a reaction Capable of UV light absorbing organic spent; the 2,4-dichloro-6- (3-oxy-4-benzoyl-phen bonds have been prepared with cyanuric chloride, oxy) -triazine precipitates as a colorless substance. als Lichtschutzmittel für Cellulose und für Cellulose- .... , , T., ti . ^ , as light stabilizers for cellulose and for cellulose ....,, T. , ti . ^, ... . t b) Verwendung des Lichtschutzmittels... t b) Use of the light stabilizer
DE19591418756 1959-11-14 1959-11-14 Use of certain compounds as light stabilizers for cellulose and cellulose diacetate. Eliminated from: 1116393 Expired DE1418756C3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DED0034875 1959-11-14

Publications (3)

Publication Number Publication Date
DE1418756A1 DE1418756A1 (en) 1969-02-13
DE1418756B2 DE1418756B2 (en) 1974-01-17
DE1418756C3 true DE1418756C3 (en) 1974-08-15

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Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0717140B1 (en) * 1994-12-13 2006-08-09 Ciba SC Holding AG Method for the treatment of textile fibres

Also Published As

Publication number Publication date
DE1418756A1 (en) 1969-02-13
DE1418756B2 (en) 1974-01-17

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Legal Events

Date Code Title Description
SH Request for examination between 03.10.1968 and 22.04.1971
C3 Grant after two publication steps (3rd publication)