US3294570A - Optical brightening of materials of synthetic polyesters and polyamides - Google Patents

Optical brightening of materials of synthetic polyesters and polyamides Download PDF

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Publication number
US3294570A
US3294570A US406545A US40654564A US3294570A US 3294570 A US3294570 A US 3294570A US 406545 A US406545 A US 406545A US 40654564 A US40654564 A US 40654564A US 3294570 A US3294570 A US 3294570A
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US
United States
Prior art keywords
bis
benzene
polyamides
optical brightening
liquor
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
Application number
US406545A
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English (en)
Inventor
Pommer Horst
Stilz Walter
Hantge Hartmut
Rosenkranz Magnus
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BASF SE
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BASF SE
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Publication date
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Publication of US3294570A publication Critical patent/US3294570A/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/52—Radicals substituted by halogen atoms or nitro radicals
    • 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
    • D06L4/614—Optical bleaching or brightening in aqueous solvents
    • D06L4/636—Optical bleaching or brightening in aqueous solvents with disperse brighteners
    • 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
    • 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
    • D06L4/671—Optical brightening assistants, e.g. enhancers or boosters
    • 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
    • D06L4/679—Fixing treatments in optical brightening, e.g. heating, steaming or acid shock

Definitions

  • the compounds remain sparingly soluble in water, for example hydroxyl, hydroxyalkyl, amino, alkylamino, carbamoyl and sulfonamido groups may also be substituents.
  • Suitable substrates are shaped articles of alltypes, for example films, sheeting, filaments, threads and staple fibres and above all plane textile materials of linear synthetic polyamides and'polyesters.
  • Polycaprolactam, polycapryllactam and polyadipic hexamethylene diamide may be emphasized among the polyamides and polyethylene glycol terephthalate among the polyesters.
  • the said compounds may be applied to the substrates, for example textile material, by various methods. They are particularly well suited to the thermosol method, the high-temperature exhaustion method and the exhaustion method at 100 C.
  • the said compounds are advantageously brought before use into a state of fine division, for example by grinding with dispersing agents, such as soaps, sulfite cellulose waste liquor, polyglycol ethers of fatty alcohols or fatty amines or condensation products of naphthalenesulfonic acids substituted naphthalenesulfonic acids and formaldehyde.
  • the treatment liquor may be alkaline, neutral or, preferably, acid.
  • the amount of optical brightener with reference to the amount of liquor, may vary within wide limits. Even with very small amounts, in certain cases for example amounts as low as 0.01 -g./l., a marked and durable effect can be achieved. Although amounts of more than 10 g./l. have not proved in general to be disadvantageous, they usually do not oifer any advantage over the normal amounts.
  • the material to be treated is padded, preferably on a padding machine, with an aqueous dispersion of the optical brightener, which may contain thickeners such as are conventionally used in printing.
  • the material is then dried and subjected to a hot air treatment.
  • the temperature of fixation depends on the com position .of the material. In the case of polyesters it may be 120 to 220 C. and in the case of polyamides 120 to 200 C. Following this treatment, the material is rinsed and soaped as usual.
  • Another embodiment consists in effecting fixation with superheated steam at temperatures between about 100 C. and 140 C. instead of with hot air. This method also gives materials showing an outstanding optical brightening effect.
  • the high-temperature exhaustion method is treatment of the material to be brightened for a long period and from a long liquor.
  • a high-temperature dyeing machine is used for this purpose at temperatures above 100 C., for example at 105 to 140 C.
  • the liquor ratio may be 5:1 to 50:1 and the residence time 30 to 60 minutes.
  • the material is treated at the boiling temperature of the liquor or in the neighborhood thereof (about 90 C.).
  • the procedure may be that the materials are introduced at 60 to 70 C. into the treatment liquor containing the optical brightener in finely divided form and the temperature is raised to 95 to'100 C.
  • the residence time may be about thirty to sixty minutes.
  • the material is then rinsed and dried. An outstanding optical brightening eifect is achieved in this way.
  • Suitable carriers are dichlorobenzene, trichlorobenzene, o-phenylphenol, p-phenylphenol, benzoic acid, the p-chlorophenyl monoether of glycol and esters of benzoic acid.
  • liquors dispersing agents such as soaps, polyglycol ethers and the like so that the brightener remains finely dispersed in the iquor.
  • Another embodiment of the process according to this invention consists in applying the optical brightener, if desired with a disperse dye, to the material to be brightened in the form of a print paste by means of the usual printing methods. Fixation is then effected in exactly the same Way as described above.
  • the said methods which in general cover the conventional methods of dyeing polyesters and polyamides with disperse dyes, may without difficulty be transferred to the treatment of filaments, threads, staple fibers, films, sheeting and other shaped articles.
  • optical brighteners to be used according to this invention are stable to solutions of bleaching agents, such :as sodium chlorite. Optical bleaching and chemical bleaching may therefore be carried out in one operation.
  • Example 1 100 parts of polyester cloth is treated for sixty minutes at 98 C. in a liquor which contains 3000 parts of water, 0.15 part of optical brightener 17 in the foregoing table which is in a state of fine division and 2.4 parts of sodium chloride and 0.6 part of the sodium salt of oleic acid tauride, 1 part of tetrasodium pyrophosphate and 0.6 part of sodium acetate.
  • the pH value of the liquor is adjusted with formic acid to 3 to 4 prior to introduction I of the cloth.
  • the cloth is rinsed and dried.
  • the treated cloth has a brilliant white appearance.
  • Example 3 100 parts of polyester yarn is treated for sixty minutes at 98 C. in a liquor containing 3000 parts of water, 12
  • Example 4 100 parts of a washed polyester cloth is treated for thirty minutes at 130 C. in a liquor containing 3000 parts of Water and 0.2 part of brightener 13 in the above table in a state of fine division. The product is rinsed and dried and polyester cloth showing an outstanding optical brightening effect and very good light and wash fastness is obtained.
  • Example 5 A polyester cloth is padded at room temperature with M a solution containing, in 1000 parts of water, 3 parts of Exqmple 6
  • a polyamide cloth is padded at room temperature with a solution containing 2.5 parts of the optical brightener 6 in. the fibQYQ table in a. state of fine division in 1000 parts of Water.
  • the liquor retention is 40%.
  • the cloth is dried at 60 to 70 C. and then subjected to a hot air treatment at 180 C. for three minutes.
  • the cloth is then soaped with 2 g./l. of soap at a liquor ratio of 50:1 for thirty minutes at 70 to 80 C. and then rinsed and dried.
  • a polyamide cloth showing an excellent optical brightening effect and good fastness to light is obtained.
  • Example 7 A polyester cloth is padded at room temperature with a solution containing, in 1000 parts of water, 2 parts of a finely divided brightener mixture of about 50% of 1-(2- cyanostyryl)-4-(4-cyanostyryl)-benzene, 25% of 1,4-bis- (2-cyanostyryl)-benzene and 25% of l,4-bis-(4-cyanostyry1)-benzene. Liquor retention is about 60%. The cloth is then dried and subjected to a hot :air treatment at 190 C. for three minutes. It is then soaped and dried. A polyester cloth showing an outstanding optical brightening effect and very good wash fastness is obtained.
  • a process for the optical brightening of a material selected from the group consisting of synthetic linear polyesters and synthetic linear polyamides which comprises treating said material by applying thereto an aqueous dispersion in which is dispersed an optical brightener which is sparingly soluble in water and consisting essentially of a member selected from the group consisting of p-bis-styryl-benezne,

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US406545A 1963-10-31 1964-10-26 Optical brightening of materials of synthetic polyesters and polyamides Expired - Lifetime US3294570A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB0074080 1963-10-31

Publications (1)

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US3294570A true US3294570A (en) 1966-12-27

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US406545A Expired - Lifetime US3294570A (en) 1963-10-31 1964-10-26 Optical brightening of materials of synthetic polyesters and polyamides

Country Status (5)

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US (1) US3294570A (enrdf_load_stackoverflow)
BE (1) BE655114A (enrdf_load_stackoverflow)
CH (1) CH465548A (enrdf_load_stackoverflow)
DE (1) DE1444003A1 (enrdf_load_stackoverflow)
GB (1) GB1045443A (enrdf_load_stackoverflow)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4380514A (en) * 1980-01-12 1983-04-19 Basf Aktiengesellschaft Preparation of optical brighteners
US4447651A (en) * 1981-05-09 1984-05-08 Bayer Aktiengesellschaft 1,4-Bis-(4-chloro-2-methoxystyryl)-benzene
US4785128A (en) * 1979-12-13 1988-11-15 Ciba-Geigy Corporation Process for the preparation of bis-styrylbenzenes
US4867906A (en) * 1987-01-29 1989-09-19 Ciba-Geigy Corporation Mixtures of fluorescent whitening agents
US4891153A (en) * 1986-03-21 1990-01-02 Ciba-Geigy Corporation Mixtures of fluorescent whitening agents

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3764040D1 (de) * 1986-07-01 1990-09-06 Ciba Geigy Ag 1,4-distryrylbenzolverbindungen und deren mischungen mit anderen 1,4-distryrylbenzolverbindungen.

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2282230A (en) * 1938-01-25 1942-05-05 Johns Manville Mineral wool product and the method of making it
US2438366A (en) * 1943-04-01 1948-03-23 Dunlop Rubber Co Drying of textile materials
US3075996A (en) * 1959-01-16 1963-01-29 Bayer Ag Brightening agents
US3076020A (en) * 1959-05-15 1963-01-29 Basf Ag New derivatives of 1, 4-bis-styrylbenzene and optical brightening therewith

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2282230A (en) * 1938-01-25 1942-05-05 Johns Manville Mineral wool product and the method of making it
US2438366A (en) * 1943-04-01 1948-03-23 Dunlop Rubber Co Drying of textile materials
US3075996A (en) * 1959-01-16 1963-01-29 Bayer Ag Brightening agents
US3076020A (en) * 1959-05-15 1963-01-29 Basf Ag New derivatives of 1, 4-bis-styrylbenzene and optical brightening therewith

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4785128A (en) * 1979-12-13 1988-11-15 Ciba-Geigy Corporation Process for the preparation of bis-styrylbenzenes
US4380514A (en) * 1980-01-12 1983-04-19 Basf Aktiengesellschaft Preparation of optical brighteners
US4447651A (en) * 1981-05-09 1984-05-08 Bayer Aktiengesellschaft 1,4-Bis-(4-chloro-2-methoxystyryl)-benzene
US4891153A (en) * 1986-03-21 1990-01-02 Ciba-Geigy Corporation Mixtures of fluorescent whitening agents
US4867906A (en) * 1987-01-29 1989-09-19 Ciba-Geigy Corporation Mixtures of fluorescent whitening agents

Also Published As

Publication number Publication date
DE1444003A1 (enrdf_load_stackoverflow) 1970-03-12
CH465548A (de) 1968-08-15
GB1045443A (en) 1966-10-12
BE655114A (enrdf_load_stackoverflow) 1965-04-30

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