US3082114A - Optically brightened textile materials - Google Patents

Optically brightened textile materials Download PDF

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Publication number
US3082114A
US3082114A US1850160A US3082114A US 3082114 A US3082114 A US 3082114A US 1850160 A US1850160 A US 1850160A US 3082114 A US3082114 A US 3082114A
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US
United States
Prior art keywords
textile materials
azamonomethine
cyanine
parts
materials
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 - Lifetime
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English (en)
Inventor
Balli Heinz
Leuchs Dieter
Schmidt Oswald
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BASF SE
Original Assignee
BASF SE
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Publication date
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Publication of US3082114A publication Critical patent/US3082114A/en
Anticipated expiration legal-status Critical
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Classifications

    • DTEXTILES; PAPER
    • D01NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01FCHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/44Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds
    • D01F6/54Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds as major constituent with other polymers or low-molecular-weight compounds of polymers of unsaturated nitriles
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62Benzothiazoles
    • C07D277/68Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D277/82Nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/36Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/45Heterocyclic compounds having sulfur in the ring
    • C08K5/46Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen in the ring
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/16Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms
    • C09B23/162Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms only nitrogen atoms
    • C09B23/164Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms only nitrogen atoms containing one nitrogen atom
    • DTEXTILES; PAPER
    • D01NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01FCHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F1/00General methods for the manufacture of artificial filaments or the like
    • D01F1/02Addition of substances to the spinning solution or to the melt
    • D01F1/06Dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06LDRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/60Optical bleaching or brightening
    • D06L4/657Optical bleaching or brightening combined with other treatments, e.g. finishing, bleaching, softening, dyeing or pigment printing
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2582Coating or impregnation contains an optical bleach or brightener or functions as an optical bleach or brightener [e.g., it masks fabric yellowing, etc.]

Definitions

  • textile materials of polymers of acrylonitrile and cellulose acetate can be brightened by the application of optical brightening agents to these materials.
  • textile materials is meant to include fibers, flocks, yarns, threads, woven and nonwoven fabrics and films.
  • cellulose acetate is intended to include both cellulose Z /t-acetate and cellulose triacetate and also cellulose acetates, the acetyl content of which lies between 2 /2 and 3 groups per glucose moiety.
  • polymers of acrylonitrile is meant to include polyacrylonitrile itself and copolymers of acrylonitrile with other polymerizable compounds as, for example, vinyl chloride and vinyl acetate, the acrylonitrile component determining the tinctorial properties of the said copolymers.
  • Such copolymers preferably contain more than 50% of their weight of acrylonitrile.
  • the textile materials to be brightened may contain any of the usual additives as, for example, dyestuffs and textile auxiliaries.
  • optical brightening agents are conventionally ap plied to the said materials in an aqueous suspension.
  • aqueous suspensions of optical brightening agents however, has some disadvantages; thus, for example, the suspensions may flocculate and thus cause an unlevelled brightening eifect.
  • optical brightening agents it is therefore desirable to apply optical brightening agents to the said materials in aqueous solutions. Unfortunately, however, most of the prior optical brightening agents do not go on to said materials from aqueous solutions.
  • the object of the invention is achieved by treating textile materials of polymers of acrylonitrile or cellulose acetate with salt-like azamonomethine cyanine compounds of the general formula in which Y and Y are identical or different and represent hydrogen atoms, methyl groups or methoxy groups and X is the equivalent of an anion.
  • the nature of the anion has no significance for the brightening action of the said azamonomethine cyanines. It may be an inorganic anion, as for example a chloride, bromide, iodide, perchlorate or sulfate anion, or an orcorporating the azamonomethine cyanines to be brightened before or during the shaping of the same. More advantageously, however, the azamonomethine cyanines can be applied to the shaped textile materials themselves from an aqueous solution by the usual dyeing processes.
  • sufiicient for the production of a strong brightening effect small amounts are usually sufiicient, as for example 0.01 to 5%,
  • azarnonomethine cyanine preferably 0.05 to 0.5%, of azarnonomethine cyanine with reference to the Weight of the material to be brightened.
  • the White effects achieved by the process according to this invention are outstandingly fast 5 to the action of sunlight and to the usual wet treatments, such as washing.
  • Example 1 parts of previously washed polyacrylonitrile fabric are treated for 30 minutes at 98 C. in a bath which contains 3,000 parts of Water, 003 to 0.3 part of the azamonomethine cyanine:
  • the treated fabric After rinsing and drying, the treated fabric has a pure white appearance.
  • the brightening effect is eminently fast to light and washing.
  • Example 2 100 parts of a polyacrylonitrile skein yarn are kept moving for 30 minutes at 98 to 100 C. in a bath of 3,000 parts of water, 0.03 to 0.3 part of the azamonomethine cyanine:
  • the treated yarn appears pure white.
  • the compounds are water- By using the compound of the formula:
  • Example 3 A washed fabric of polyacrylonitrile staple fiber is treated for 60 minutes at a liquor ratio of 1:30 in a bath containing, in 1,000 parts of Water, 2 parts of sodium chlorite, 0.3 part of the sodium salt of oleic acid methyl tauride, 0.5 part of tetrasodium pyrophosphate, 0.3 part of sodium acetate and 0.01 to 0.1 part of the azamonomethine cyanine used in Example 1.
  • the pH value of the bath is adjusted to 3.5 to 4 with formic acid prior to the introduction of the fabric. After rinsing and drying, the treated fabric has a brilliant white appearance.
  • Example 4 100 parts of a washed cellulose acetate fabric are treated I CH CH in which Y and Y each represent a member selected from the group consisting of hydrogen, methyl and methoxy, and X is an anion.
  • a textile material as claimed in claim 1 containing about 0.01 to 5.0% by weight thereof of said azamonomethine cyanine.
  • a textile material as claimed in claim 1 containing about 0.1 to 0.5% by Weight thereof of said azamonomethine cyanine.
  • a textile material as claimed in claim 2 wherein the azamonomethine cyanine has the formula CH CH3 5.
  • a textile material as claimed in claim 2 wherein the azamonomethine cyanine has the formula s s IHEGO- 00m CH3 CH with an aqueous bath containing a bleaching agent and an azamonomethine cyanine of the formula in which Y and Y each represent a member selected from the group consisting of hydrogen, methyl and methoxy, and X is an anion.
  • bleaching agent is an alkali metal chlorite.
  • a process as claimed in claim 8 wherein said b1eaching agent is sodium chlorite.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Textile Engineering (AREA)
  • General Chemical & Material Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Artificial Filaments (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Coloring (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
US1850160 1959-04-01 1960-03-30 Optically brightened textile materials Expired - Lifetime US3082114A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB52683A DE1089721B (de) 1959-04-01 1959-04-01 Aufhellungsmittel

Publications (1)

Publication Number Publication Date
US3082114A true US3082114A (en) 1963-03-19

Family

ID=6969984

Family Applications (1)

Application Number Title Priority Date Filing Date
US1850160 Expired - Lifetime US3082114A (en) 1959-04-01 1960-03-30 Optically brightened textile materials

Country Status (6)

Country Link
US (1) US3082114A (de)
BE (1) BE589006A (de)
CH (2) CH365829A (de)
DE (1) DE1089721B (de)
FR (1) FR1253025A (de)
GB (1) GB895084A (de)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3779937A (en) * 1971-12-31 1973-12-18 Ciba Geigy Ag Optical filter layer
US20040096775A1 (en) * 2001-03-21 2004-05-20 Urs Lehmann Optical recording materials having high storage density
US20070191246A1 (en) * 2006-01-23 2007-08-16 Sivik Mark R Laundry care compositions with thiazolium dye
JP2008528594A (ja) * 2005-01-25 2008-07-31 ザ プロクター アンド ギャンブル カンパニー ケラチン繊維を着色するためのカチオン性アザシアニン染料の使用
US20090286709A1 (en) * 2007-01-19 2009-11-19 Eugene Steven Sadlowski Novel whitening agents for cellulosic substrates
US7642282B2 (en) 2007-01-19 2010-01-05 Milliken & Company Whitening agents for cellulosic substrates
JP4759001B2 (ja) * 2005-01-25 2011-08-31 ザ プロクター アンド ギャンブル カンパニー カチオン性アザシアニン染料を含む着色剤
US9163146B2 (en) 2011-06-03 2015-10-20 Milliken & Company Thiophene azo carboxylate dyes and laundry care compositions containing the same
US9796952B2 (en) 2012-09-25 2017-10-24 The Procter & Gamble Company Laundry care compositions with thiazolium dye
US9856439B2 (en) 2010-11-12 2018-01-02 The Procter & Gamble Company Thiophene azo dyes and laundry care compositions containing the same

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE620258A (de) * 1961-07-14

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2080049A (en) * 1934-08-03 1937-05-11 Ilford Ltd Production of dyes of the cyanine type
US2307049A (en) * 1935-08-16 1943-01-05 Ilford Ltd Process of producing aza-methine dyes
US2809123A (en) * 1955-03-04 1957-10-08 Geigy Ag J R Fibrous synthetic material of improved whiteness

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2080049A (en) * 1934-08-03 1937-05-11 Ilford Ltd Production of dyes of the cyanine type
US2307049A (en) * 1935-08-16 1943-01-05 Ilford Ltd Process of producing aza-methine dyes
US2809123A (en) * 1955-03-04 1957-10-08 Geigy Ag J R Fibrous synthetic material of improved whiteness

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3779937A (en) * 1971-12-31 1973-12-18 Ciba Geigy Ag Optical filter layer
US20040096775A1 (en) * 2001-03-21 2004-05-20 Urs Lehmann Optical recording materials having high storage density
JP4772803B2 (ja) * 2005-01-25 2011-09-14 ザ プロクター アンド ギャンブル カンパニー ケラチン繊維を着色するためのカチオン性アザシアニン染料を含む剤及びカチオン性アザシアニン染料を用いた毛髪の着色方法
JP4759001B2 (ja) * 2005-01-25 2011-08-31 ザ プロクター アンド ギャンブル カンパニー カチオン性アザシアニン染料を含む着色剤
JP2008528594A (ja) * 2005-01-25 2008-07-31 ザ プロクター アンド ギャンブル カンパニー ケラチン繊維を着色するためのカチオン性アザシアニン染料の使用
US8299010B2 (en) 2006-01-23 2012-10-30 The Procter & Gamble Company Laundry care compositions with thiazolium dye
US8461095B2 (en) 2006-01-23 2013-06-11 Milliken & Company Laundry care compositions with thiazolium dye
US20070203053A1 (en) * 2006-01-23 2007-08-30 Eduardo Torres Laundry care compositions with thiazolium dye
US7674757B2 (en) 2006-01-23 2010-03-09 Milliken & Company Laundry care compositions with thiazolium dye
US20100325814A1 (en) * 2006-01-23 2010-12-30 Mark Robert Sivik Laundry care compositions with thiazolium dye
US7977300B2 (en) 2006-01-23 2011-07-12 Milliken & Co. Laundry care compositions with thiazolium dye
US20110196137A1 (en) * 2006-01-23 2011-08-11 Eduardo Torres Laundry Care Compositions With Thiazolium Dye
US20070191246A1 (en) * 2006-01-23 2007-08-16 Sivik Mark R Laundry care compositions with thiazolium dye
US8022100B2 (en) 2007-01-19 2011-09-20 Milliken & Co. Whitening agents for cellulosic substrates
US20100025633A1 (en) * 2007-01-19 2010-02-04 Valenti Michael A Novel Whitening Agents For Cellulosic Substrates
US8138222B2 (en) 2007-01-19 2012-03-20 Milliken & Company Whitening agents for cellulosic substrates
US8247364B2 (en) 2007-01-19 2012-08-21 The Procter & Gamble Company Whitening agents for cellulosic substrates
US7642282B2 (en) 2007-01-19 2010-01-05 Milliken & Company Whitening agents for cellulosic substrates
US8367598B2 (en) 2007-01-19 2013-02-05 The Procter & Gamble Company Whitening agents for cellulosic subtrates
US20090286709A1 (en) * 2007-01-19 2009-11-19 Eugene Steven Sadlowski Novel whitening agents for cellulosic substrates
US8536218B2 (en) 2007-01-19 2013-09-17 The Procter & Gamble Company Whitening agents for cellulosic substrates
US8703688B2 (en) 2007-01-19 2014-04-22 The Procter & Gamble Company Whitening agents for cellulosic substrates
US11946025B2 (en) 2007-01-19 2024-04-02 The Procter & Gamble Company Whitening agents for cellulosic substrates
US11198838B2 (en) 2007-01-19 2021-12-14 The Procter & Gamble Company Whitening agents for cellulosic substrates
US10526566B2 (en) 2007-01-19 2020-01-07 The Procter & Gamble Company Whitening agents for cellulosic substrates
US10435651B2 (en) 2010-11-12 2019-10-08 The Procter & Gamble Company Thiophene azo dyes and laundry care compositions containing the same
US9856439B2 (en) 2010-11-12 2018-01-02 The Procter & Gamble Company Thiophene azo dyes and laundry care compositions containing the same
US10655091B2 (en) 2010-11-12 2020-05-19 The Procter & Gamble Company Thiophene azo dyes and laundry care compositions containing the same
US9567465B2 (en) 2011-06-03 2017-02-14 Milliken & Company Thiophene azo carboxylate dyes and laundry care compositions containing the same
US9163146B2 (en) 2011-06-03 2015-10-20 Milliken & Company Thiophene azo carboxylate dyes and laundry care compositions containing the same
US9796952B2 (en) 2012-09-25 2017-10-24 The Procter & Gamble Company Laundry care compositions with thiazolium dye

Also Published As

Publication number Publication date
DE1089721B (de) 1960-09-29
CH365693A (de) 1963-01-15
CH265160A4 (de) 1962-08-15
GB895084A (en) 1962-05-02
FR1253025A (fr) 1961-02-03
CH365829A (de) 1962-11-30
BE589006A (fr) 1960-07-18

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