US2776909A - Dry-cleaning and brightening of textiles - Google Patents

Dry-cleaning and brightening of textiles Download PDF

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Publication number
US2776909A
US2776909A US321289A US32128952A US2776909A US 2776909 A US2776909 A US 2776909A US 321289 A US321289 A US 321289A US 32128952 A US32128952 A US 32128952A US 2776909 A US2776909 A US 2776909A
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dry
cleaning
brightening
formula
compound
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US321289A
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Fleck Fritz
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Sandoz AG
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Sandoz AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
    • 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
    • D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
    • D06L1/02—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents
    • D06L1/04—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using organic solvents combined with specific additives
    • 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

Definitions

  • the present invention relates to dry-cleaning compo: sitions and to materials treated therewith.
  • the new dry-cleaning compositions of the present application consist essentially of solutions containing a small quantity of a compound which corresponds to the formula wherein each of X1, X2, Y1 and Y2 stands for hydrogen or lower alkyl (e. g. methyl, ethyl, propyl,-butyl, etc.).
  • Compounds which correspond to this formula are, for example, 7-monomethylamino4-methylcoumarin, 7-dimethylamino 4 methylcoumarin, 7 monoethylamino- 4 methylcoumarin, 7 diethylamino 3,4 dimethylcoumarin, 7-diethylamino-4-methyl-coumarin, etc.
  • salts thereof which are soluble in organic solvents, with acids, as for example the organic acids such as formic acid, lauric acid, stearic acid, benzoic acid, etc.
  • Solvents employed for preparing the dry-cleaning compositions of the present invention are those volatile waterimmiscible organic solvents which are conventionally used in dry-cleaning.
  • the solvent is a volatile chlorinated hydrocarbon such as for example trichlorethylene, tetrachlorethylene and carbon tetrachloride or Stoddard solvent.
  • the solution contains from 0.03 to 0.3% by weight of compound I.
  • the solution may also contain oil-soluble soaps or compounds having a similar action, in addition to the aforesaid ingredient I.
  • An advantage of the present invention compared with the hitherto known processes of optical brightening is that by treatment with a dry-cleaning composition according to the invention, a combined dry-cleaning and optical brightening is achieved.
  • the material which is simultaneously to be dry-cleaned and brightened is immersed in a solution, as aforedescribed, of the compound I or a salt thereof which is soluble in organic solvents, and the impregnated material is then centrifuged or wrung out or dried. The material is then subjected to an after-steaming treatment, whereby the brightening effect is greatly enhanced.
  • ExampleZ A mixed fabric of wool with nylon effect threads is treated in a bath of 1:10 of benzine which contains, per liter, 1 grain of 7-dimethylamino-4-methylcoumarin, the latter compound being introduced in the form of a 10% by weight solution in trichloroethylene.
  • the fabric is manipulated in the bath for a short time, the excess of solvent is removed by centrifuging and the material, after recovery of the solvent, steamed. Both the wool and nylon effect threads are markedly brightened.
  • Example3 A silk fabric, which is printed in colors on a White background, is subjected to dry cleaning in a bath (1:10) containing 1 gram of 7-mcnoethylamino-4-methylcoumarin per liter of tetrachlorethane. After recovery of the solvent and steaming of the fabric, the white background is beautifully brightened and the colored printed portions are imparted a purity of shade and brilliance. The amount of the brightening compound applied may vary according to the desired effect in large extent.
  • the method of dry-cleaning and optically brightening textile material which comprises subjecting the said material to the dry-cleaning action of a composition consisting essentially of a volatile chlorinated hydrocarbon water-immiscible organic solvent, and 0.03 to 0.3% by weight of a member selected from the group consisting of compounds of the formula Yr I wherein each of X1, X2, Y1 and Y2 stands for a member selected from the group consisting of hydrogen and lower alkyl, and salts thereof with organic monocarboxylic acids, dissolved therein, and then subjecting the thustreated material to an after-steaming operation.

Description

DRY-CLEANING AND BRIGHTENING OF TEXTILES Fritz Fleck, Basel, Switzerland, assignor to Sandoz A. G., Basel, Switzerland, a Swiss firm No Drawing. Application November 18, 1952, Serial No. 321,289
Claims priority, application Switzerland October 5, 1949 6 Claims. (Cl. 117-335) The present invention relates to dry-cleaning compo: sitions and to materials treated therewith.
The new dry-cleaning compositions of the present application consist essentially of solutions containing a small quantity of a compound which corresponds to the formula wherein each of X1, X2, Y1 and Y2 stands for hydrogen or lower alkyl (e. g. methyl, ethyl, propyl,-butyl, etc.). Compounds which correspond to this formula are, for example, 7-monomethylamino4-methylcoumarin, 7-dimethylamino 4 methylcoumarin, 7 monoethylamino- 4 methylcoumarin, 7 diethylamino 3,4 dimethylcoumarin, 7-diethylamino-4-methyl-coumarin, etc. In addition to the free coumarins, use may also be made of salts thereof which are soluble in organic solvents, with acids, as for example the organic acids such as formic acid, lauric acid, stearic acid, benzoic acid, etc.
Solvents employed for preparing the dry-cleaning compositions of the present invention are those volatile waterimmiscible organic solvents which are conventionally used in dry-cleaning. Preferably the solvent is a volatile chlorinated hydrocarbon such as for example trichlorethylene, tetrachlorethylene and carbon tetrachloride or Stoddard solvent. Most advantageously, the solution contains from 0.03 to 0.3% by weight of compound I. The solution may also contain oil-soluble soaps or compounds having a similar action, in addition to the aforesaid ingredient I.
It has already been proposed to enhance the whiteness of fibers by the application thereto of small amounts of a substantive blue-fluorescing substance.
An advantage of the present invention compared with the hitherto known processes of optical brightening is that by treatment with a dry-cleaning composition according to the invention, a combined dry-cleaning and optical brightening is achieved.
In a representative mode of procedure according to the invention, the material which is simultaneously to be dry-cleaned and brightened is immersed in a solution, as aforedescribed, of the compound I or a salt thereof which is soluble in organic solvents, and the impregnated material is then centrifuged or wrung out or dried. The material is then subjected to an after-steaming treatment, whereby the brightening effect is greatly enhanced.
Presently-preferred illustrative embodiments of the invention are set forth in the examples which follow.
ratio of 1:10 with a solution containing 0.3 gram of 7- diethylamino-4-methylcournarin per liter of trichlorethylene. The impregnated product is then squeezed out until 2,776,909 atented Jan. 8, 1957 it contains about by weight of solvent whereupon, after recovery of the solvent, it is steamed from 5 to 10 minutes with dry steam. In this Way there is obtained a very beautiful white fabric which contains 0.03% by weight of the aforementioned coumarin.
By replacing, in this example, the 7-diethylamino-4- methylcournarin by 7-monomethylamino-4methyl-coumarin or by the formate, laurate, stearate or benzoate of these two compounds using a silk-nylon mixed fabric in place of acetate silk, a greatly brightened product is obtained.
ExampleZ A mixed fabric of wool with nylon effect threads is treated in a bath of 1:10 of benzine which contains, per liter, 1 grain of 7-dimethylamino-4-methylcoumarin, the latter compound being introduced in the form of a 10% by weight solution in trichloroethylene. The fabric is manipulated in the bath for a short time, the excess of solvent is removed by centrifuging and the material, after recovery of the solvent, steamed. Both the wool and nylon effect threads are markedly brightened.
A similar result is obtained by replacing in this example the trichlorethylene by monochlorobenzene and the wool-nylon fabric by viscose-acetate silk fabric.
Example3 Example 4 A silk fabric, which is printed in colors on a White background, is subjected to dry cleaning in a bath (1:10) containing 1 gram of 7-mcnoethylamino-4-methylcoumarin per liter of tetrachlorethane. After recovery of the solvent and steaming of the fabric, the white background is beautifully brightened and the colored printed portions are imparted a purity of shade and brilliance. The amount of the brightening compound applied may vary according to the desired effect in large extent.
This application is in part a continuation of copending application, Ser. No. 188,065, filed October 2, 1950, and now abandoned.
Having thus disclosed the invention, what is claimed is:
1. The method of dry-cleaning and optically brightening textile material, which comprises subjecting the said material to the dry-cleaning action of a composition consisting essentially of a volatile chlorinated hydrocarbon water-immiscible organic solvent, and 0.03 to 0.3% by weight of a member selected from the group consisting of compounds of the formula Yr I wherein each of X1, X2, Y1 and Y2 stands for a member selected from the group consisting of hydrogen and lower alkyl, and salts thereof with organic monocarboxylic acids, dissolved therein, and then subjecting the thustreated material to an after-steaming operation.
2. The method of dry-cleaning and optically brightening textile material according to claim 1, wherein'the compound of the said formula is 7-diethy1amino-4-methy1- coumarin.
3. The method of dry-eleaning and optically brightening textile material according to claim 1, whereinthe compound of the said formula is 7-monomethylamino-4- methylcoumarin.
4. The method of dry-cleaning and optically brightening textile material according to.claim 1, wherein.the compound of the said formula is 7-dimethylamino-4- methylcournarin.
5. The method of dry-cleaning and optically brightening textile material according toclaim 1, wherein the 4 compound of thesaid formula is 7-monoethylamino-4- methylcoumarin.
6. The method of dry-cleaning and optically brightening textile material according to claim 1, wherein the compound of the said formula is 7-diethylamino-3,4-dimethylcoumarin.
References Cited in the file of this patent 'UNITED STATES PATENTS 10 2,180,508 De Fraine Nov. 21, 1939 2,247,259 Snell June 24, 1941 2,333,329 Miglarese Nov. 2, 1943 2,341,009 Axelrad Feb. 8, 1944 2,610,152 Ackermann Sept. 9, 1952

Claims (1)

1. THE METHOD OF DRY-CLEANING AND OPTICALLY BRIGHTENING TEXTILE MATERIAL, WHICH COMPRISES SUBJECTING THE SAID MATERIAL TO THE DRY-CLEANING ACTION OF A COMPOSITION CONSISTING ESSENTIALLY OF A VOLATILE CHLORINATED HYDROCARBON WATER-IMMISCIBLE ORGANIC SOLVENT, AND 0.03 TO 0.3% BY WEIGHT OF A MEMBER SELECTED FROM THE GROUP CONSISTING OF COMPOUNDS OF THE FORMULA
US321289A 1949-10-05 1952-11-18 Dry-cleaning and brightening of textiles Expired - Lifetime US2776909A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH689708X 1949-10-05

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US2776909A true US2776909A (en) 1957-01-08

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US (1) US2776909A (en)
BE (1) BE498447A (en)
CH (1) CH277956A (en)
DE (1) DE904646C (en)
FR (1) FR1025467A (en)
GB (1) GB689708A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2878138A (en) * 1955-09-28 1959-03-17 Bayer Ag Method of brightening material
US2998326A (en) * 1956-04-04 1961-08-29 Nat Starch Products Inc Cleaning and sizing of fabrics
US4028550A (en) * 1975-12-22 1977-06-07 E. I. Du Pont De Nemours And Company X-ray screens
EP0091261A2 (en) * 1982-04-02 1983-10-12 Hollygrange Limited Dry cleaning process
WO2002050365A1 (en) * 2000-12-20 2002-06-27 Unilever N.V. Fabric cleaning system
WO2002050364A1 (en) * 2000-12-20 2002-06-27 Unilever N.V. Fabric cleaning system

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1275983B (en) * 1956-08-30 1968-08-29 Basf Ag Optical brighteners
DE1205941B (en) * 1959-01-16 1965-12-02 Bayer Ag Optical brighteners
CH648789A5 (en) * 1980-10-03 1985-04-15 Schweizerische Seidengaze METHOD FOR SHORTERING THE EXPOSURE TIME IN PHOTOCHEMICAL PATTERN TRANSFER ON LIGHT SENSITIVE LAYERS.

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2180508A (en) * 1934-06-20 1939-11-21 Fraine De Method and material for marking laundered articles
US2247259A (en) * 1939-03-28 1941-06-24 Foster D Snell Inc Method and composition for marking articles
US2333329A (en) * 1941-04-07 1943-11-02 Nat Marking Mach Co Ink and method of marking dry cleaned articles therewith
US2341009A (en) * 1936-03-19 1944-02-08 Richards Chemical Works Method of improving brightness of fibrous materials
US2610152A (en) * 1946-06-14 1952-09-09 Ciba Ltd Detergent compositions containing amino-coumarins

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2180508A (en) * 1934-06-20 1939-11-21 Fraine De Method and material for marking laundered articles
US2341009A (en) * 1936-03-19 1944-02-08 Richards Chemical Works Method of improving brightness of fibrous materials
US2247259A (en) * 1939-03-28 1941-06-24 Foster D Snell Inc Method and composition for marking articles
US2333329A (en) * 1941-04-07 1943-11-02 Nat Marking Mach Co Ink and method of marking dry cleaned articles therewith
US2610152A (en) * 1946-06-14 1952-09-09 Ciba Ltd Detergent compositions containing amino-coumarins

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2878138A (en) * 1955-09-28 1959-03-17 Bayer Ag Method of brightening material
US2998326A (en) * 1956-04-04 1961-08-29 Nat Starch Products Inc Cleaning and sizing of fabrics
US4028550A (en) * 1975-12-22 1977-06-07 E. I. Du Pont De Nemours And Company X-ray screens
EP0091261A2 (en) * 1982-04-02 1983-10-12 Hollygrange Limited Dry cleaning process
EP0091261A3 (en) * 1982-04-02 1984-04-18 Hollygrange Limited Dry cleaning process
WO2002050365A1 (en) * 2000-12-20 2002-06-27 Unilever N.V. Fabric cleaning system
WO2002050364A1 (en) * 2000-12-20 2002-06-27 Unilever N.V. Fabric cleaning system

Also Published As

Publication number Publication date
BE498447A (en)
GB689708A (en) 1953-04-01
FR1025467A (en) 1953-04-15
CH277956A (en) 1951-09-30
DE904646C (en) 1954-02-22

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