US3082114A - Optically brightened textile materials - Google Patents
Optically brightened textile materials Download PDFInfo
- 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
- Authority
- 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
Links
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
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/44—Monocomponent 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
- D01F6/54—Monocomponent 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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
- C07D277/82—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/45—Heterocyclic compounds having sulfur in the ring
- C08K5/46—Heterocyclic compounds having sulfur in the ring with oxygen or nitrogen in the ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/16—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms
- C09B23/162—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms only nitrogen atoms
- C09B23/164—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing hetero atoms only nitrogen atoms containing one nitrogen atom
-
- 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
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/06—Dyes
-
- 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
- D06L4/657—Optical bleaching or brightening combined with other treatments, e.g. finishing, bleaching, softening, dyeing or pigment printing
-
- Y—GENERAL 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated 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
- Y10T442/2582—Coating 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)
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)
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE620258A (de) * | 1961-07-14 |
Citations (3)
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 |
-
1959
- 1959-04-01 DE DEB52683A patent/DE1089721B/de active Pending
-
1960
- 1960-03-09 CH CH55262A patent/CH365829A/de unknown
- 1960-03-09 CH CH265160A patent/CH365693A/de unknown
- 1960-03-24 BE BE589006A patent/BE589006A/fr unknown
- 1960-03-30 US US1850160 patent/US3082114A/en not_active Expired - Lifetime
- 1960-03-31 FR FR822979A patent/FR1253025A/fr not_active Expired
- 1960-03-31 GB GB1134960A patent/GB895084A/en not_active Expired
Patent Citations (3)
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)
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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