US2690954A - After-treatment of acid-dyed cellulose acetate with salicylic acid - Google Patents
After-treatment of acid-dyed cellulose acetate with salicylic acid Download PDFInfo
- Publication number
- US2690954A US2690954A US274510A US27451052A US2690954A US 2690954 A US2690954 A US 2690954A US 274510 A US274510 A US 274510A US 27451052 A US27451052 A US 27451052A US 2690954 A US2690954 A US 2690954A
- Authority
- US
- United States
- Prior art keywords
- cellulose acetate
- acid
- salicylic acid
- treatment
- light
- 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
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 title claims description 24
- 229920002301 cellulose acetate Polymers 0.000 title claims description 23
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 title claims description 12
- 229960004889 salicylic acid Drugs 0.000 title claims description 12
- 239000000243 solution Substances 0.000 claims description 16
- 239000000980 acid dye Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 9
- -1 DI-METHYL AMINO ETHYL Chemical class 0.000 claims description 8
- 238000004043 dyeing Methods 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 229940081735 acetylcellulose Drugs 0.000 description 21
- 239000000975 dye Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 239000004753 textile Substances 0.000 description 5
- 238000005562 fading Methods 0.000 description 4
- 239000000835 fiber Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
- WZXYIWMZCIFNRB-UHFFFAOYSA-N 2-methylprop-2-enoate;tris(2-hydroxyethyl)azanium Chemical compound CC(=C)C(O)=O.OCCN(CCO)CCO WZXYIWMZCIFNRB-UHFFFAOYSA-N 0.000 description 1
- ZAMLGGRVTAXBHI-UHFFFAOYSA-N 3-(4-bromophenyl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(CC(O)=O)C1=CC=C(Br)C=C1 ZAMLGGRVTAXBHI-UHFFFAOYSA-N 0.000 description 1
- 241001136792 Alle Species 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920006218 cellulose propionate Polymers 0.000 description 1
- 230000000332 continued effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 125000005853 β-dimethylaminoethyl group Chemical group 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/40—Cellulose acetate
- D06P3/401—Cellulose acetate using acid dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/02—After-treatment
- D06P5/04—After-treatment with organic compounds
-
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/921—Cellulose ester or ether
Definitions
- cellulose acetate has been one of the major problems of the trade. This is commonly attributed to the fact that the cellulose acetate molecule has few available reactive groups. Yarns and fabrics produced from mixed fibers and filaments and containing cellulose acetate are particularly difiicult to process due to this dyeing problem. It is known in the art that cellulose acetate can be modified to increase its susceptibility toward various types of dyes. For instance, addition of 2 to of one or more non-cellulosic, non-proteinous, polymeric compounds containing amino nitrogen to the acetone solution from which the cellulose acetate is spun will render it suitable for acid dye application.
- suitable amino additives may be mentioned beta dimethylaminoethyl alpha methacrylate, beta diethylaminoethyl alpha methacrylate, triethanolamine monomethacrylate, 4- (beta methacrylyoxyethyl) morpholine and the like.
- the preparation of such acid-dye receptive cellulose acetate is described in detail in British Patent 480,297.
- modified cellulose acetate is commonly known as, and is referred to herein as, basic cellulose acetate.
- dyes are relatively inexpensive, are simple to apply, and have sufiicient afiinity for basic cellulose acetate, it has been found that they possess poor light-fastness when applied to this material.
- an aftertreatment has been developed whichimproves the light-fastness of acid-dyed, basic cellulose acetate.
- Another object is to provide an acid-dyed basic cellulose acetate of improved light-fast characteristics.
- the aftertreatment of the present invention comprises contacting the dyed cellulose acetate products with a solution of salicylic acid.
- a basic cellulose acetate in any form, such as a fiber, filament, yarn, fabric, pellicle or the like, is dyed with an acid dye and then subjected to a solution of salicylic acid.
- the nature of the solvent is not critical. However, to avoid spotting of the textile, it is preferred that the salicylic acid be completely in solution. Water is the most convenient solvent. Alcoholic or aqueous alcoholic solutions or other organic solvents which do not affect the textile or the dye may likewise be employed. In general, it is recommended that the treating solutions contain from 2.5 to 25 grams of salicylic acid per liter of solution employed.
- the method of applying the salicylic acid solution is not critical although care should be taken to obtain thorough and even distribution. Immersion, as by the use of a jig or beck is suitable.
- the treatment period in each case, is related to the ease with which the structural configuration of the textile material to be treated permits proper coverage. Furthermore, the period of contact is related to the strength of the treating solution. For immersion in aqueous solutions, contact periods of from about 15 to 30 minutes are satisfactory in the higher concentrations of the range indicated above, to about to minutes in the lower concentrations. These values will Vary considerably, depending upon the physical characteristics of the material treated. It is not necessary to the stability of either the dye or the basic cellulose acetate that excess treating liquid be washed out.
- the ratio of textile weight to dyebath is not critical. It is convenient to use from 5 to times more liquid by weight than textile.
- the stabilizing solution can be applied to the dyed basic cellulose acetate after it has been dried, or while it is still moist from the dyeing step.
- the nature of the acid dye is not critical. Many such dyes are known to the industry (Colour Index, edited by F. M. Rowe, published by the Society of Dyers and Colourists, Bradford, England) Among such materials may be mentioned the sodium bisulphite salt of para-sulphobenzene-azo-beta-naphthol (C. I. 152), the toluenepara-sulphonyl esters (CI. 430), the sodium salt of the toluene-para-sulphonyl-ether of 4-pa1'ahydroxybenzene azo l para chloro orthosulpho phenyl 3 methyl hydroxypyrazol (C. I.
- EXAMPLE I A tubing knitted from a 150/48 cellulose acetate yarn which contains 5% of di-methyl amino ethyl methacrylate is dyed at 212 F. to a redviolet color in 40 times its volume of a neutral aqueous bath containing 0.5% on weight of fiber of sulfonated 2-an'1lino quinizarin acid dye. At the end of 30 minutes, a 28% aqueous acetic acid solution, which corresponds to 1% acetic acid based on fabric, is added. The dyeing is con-- tinued for another 30 minutes at 212 F. The fabric is then rinsed and dried. A 3 x 4 inch swatch is removed as a control and tested for light-fastness. Fading is observed in 4.5 hours. This corresponds to a fastness to light rating of L2.
- the remaining unexposed fabric is then immersed for 5 minutes at 212 F. in 40 times its volume of an aqueous solution containing grams per liter of salicylic acid. Upon drying, a swatch is subjected to the light test described above. Fading occurred in 21 hours, corresponding to a fastness to light rating of L5.
- Example I Following the general procedure outlined in Example I, a series of dyeings is made on similar yarn employing various dyes as indicated in Table I.
- a process for the treatment of cellulose acetate which has been rendered acid dye sensitive by incorporating in it polymeric di-methyl amino ethyl methacrylate which comprises dyeing the said cellulose acetate with an acid dye and thereafter contacting it at 212 F. for about at least 5 minutes with an aqueous solution containing about 15 grams of salicylic acid per liter of solution to render it light-fast.
Description
Patented Oct. 5, 1954 siren STATES PATENT OFFICE AFTER-TREATMENT OF ACID-DYED CELLU- LOSE ACETATE WITH SALICYLIC ACID Barbara Jane Weir, Wilmington, DeL, assignor to E. 1. du Pont de Nemours and Company, Wihnington, Del, a corporation of Delaware No Drawing. Application March 1, 1952, Serial No. 274,510
3 Claims.
pellicle and the like, for the great majority of I.
commonly employed dyes has been one of the major problems of the trade. This is commonly attributed to the fact that the cellulose acetate molecule has few available reactive groups. Yarns and fabrics produced from mixed fibers and filaments and containing cellulose acetate are particularly difiicult to process due to this dyeing problem. It is known in the art that cellulose acetate can be modified to increase its susceptibility toward various types of dyes. For instance, addition of 2 to of one or more non-cellulosic, non-proteinous, polymeric compounds containing amino nitrogen to the acetone solution from which the cellulose acetate is spun will render it suitable for acid dye application. Among suitable amino additives may be mentioned beta dimethylaminoethyl alpha methacrylate, beta diethylaminoethyl alpha methacrylate, triethanolamine monomethacrylate, 4- (beta methacrylyoxyethyl) morpholine and the like. The preparation of such acid-dye receptive cellulose acetate is described in detail in British Patent 480,297. Such modified cellulose acetate is commonly known as, and is referred to herein as, basic cellulose acetate. dyes are relatively inexpensive, are simple to apply, and have sufiicient afiinity for basic cellulose acetate, it has been found that they possess poor light-fastness when applied to this material.
In accordance with the present invention, an aftertreatment has been developed whichimproves the light-fastness of acid-dyed, basic cellulose acetate.
It is an object of the present invention to provide a process for the preparation of light-fast, acid-dyed, basic cellulose acetate.
Another object is to provide an acid-dyed basic cellulose acetate of improved light-fast characteristics.
These and other objects will become apparent in the course of the following specification and claims.
The aftertreatment of the present invention comprises contacting the dyed cellulose acetate products with a solution of salicylic acid.
While acid In accordance with the present invention, a basic cellulose acetate, in any form, such as a fiber, filament, yarn, fabric, pellicle or the like, is dyed with an acid dye and then subjected to a solution of salicylic acid. The nature of the solvent is not critical. However, to avoid spotting of the textile, it is preferred that the salicylic acid be completely in solution. Water is the most convenient solvent. Alcoholic or aqueous alcoholic solutions or other organic solvents which do not affect the textile or the dye may likewise be employed. In general, it is recommended that the treating solutions contain from 2.5 to 25 grams of salicylic acid per liter of solution employed. Where water is used as a solvent, it is necessary to heat the solution to with in a range of from about 160-2l2 F. to provide the proper solubility. Lower temperatures may be employed if a low salicylic acid concentration is used. Naturally, longer contact periods are necessary under these conditions. Higher temperatures, i. e., above the boiling point of the solution, may be employed provided suitable pressure is used to maintain the solution in the liquid state.
The method of applying the salicylic acid solution is not critical although care should be taken to obtain thorough and even distribution. Immersion, as by the use of a jig or beck is suitable. The treatment period, in each case, is related to the ease with which the structural configuration of the textile material to be treated permits proper coverage. Furthermore, the period of contact is related to the strength of the treating solution. For immersion in aqueous solutions, contact periods of from about 15 to 30 minutes are satisfactory in the higher concentrations of the range indicated above, to about to minutes in the lower concentrations. These values will Vary considerably, depending upon the physical characteristics of the material treated. It is not necessary to the stability of either the dye or the basic cellulose acetate that excess treating liquid be washed out. The ratio of textile weight to dyebath is not critical. It is convenient to use from 5 to times more liquid by weight than textile. The stabilizing solution can be applied to the dyed basic cellulose acetate after it has been dried, or while it is still moist from the dyeing step.
The nature of the acid dye is not critical. Many such dyes are known to the industry (Colour Index, edited by F. M. Rowe, published by the Society of Dyers and Colourists, Bradford, Yorkshire) Among such materials may be mentioned the sodium bisulphite salt of para-sulphobenzene-azo-beta-naphthol (C. I. 152), the toluenepara-sulphonyl esters (CI. 430), the sodium salt of the toluene-para-sulphonyl-ether of 4-pa1'ahydroxybenzene azo l para chloro orthosulpho phenyl 3 methyl hydroxypyrazol (C. I. 642), the sulphonic acids of dialkylaminophenylamino phenyl naphthophenazonium chloride (C. I. 833) and the sodium salt of 1:4 di ortho sulpho para tolylaminoanthraquinone (C. I. 1078).
The following examples are cited illustratively and not by way of limitation. The color fastness to light tests were made in accordance with tentative test method #16-45, described in the Technical Manual and Year Book of the AATCC, volume 26, pages 98, 99 (Howes Publishing Company, Inc., New York city, 1950). An FDA-P. Fade-Ometer, a carbon are fading lamp, manufactured by the Atlas Electric Devices Company, Chicago, Illinois, was employed as a source of artificial light. The specimens were exposed, one-half of the exposed area being covered with an opaque material, until the fabric being tested had faded slightly. After exposure, specimens were allowed to lie in a dark room at temperature for two hours. The samples were then classified relative to their fastness to light, as indicated in the test method.
EXAMPLE I A tubing knitted from a 150/48 cellulose acetate yarn which contains 5% of di-methyl amino ethyl methacrylate is dyed at 212 F. to a redviolet color in 40 times its volume of a neutral aqueous bath containing 0.5% on weight of fiber of sulfonated 2-an'1lino quinizarin acid dye. At the end of 30 minutes, a 28% aqueous acetic acid solution, which corresponds to 1% acetic acid based on fabric, is added. The dyeing is con-- tinued for another 30 minutes at 212 F. The fabric is then rinsed and dried. A 3 x 4 inch swatch is removed as a control and tested for light-fastness. Fading is observed in 4.5 hours. This corresponds to a fastness to light rating of L2.
The remaining unexposed fabric is then immersed for 5 minutes at 212 F. in 40 times its volume of an aqueous solution containing grams per liter of salicylic acid. Upon drying, a swatch is subjected to the light test described above. Fading occurred in 21 hours, corresponding to a fastness to light rating of L5.
Following the general procedure outlined in Example I, a series of dyeings is made on similar yarn employing various dyes as indicated in Table I.
4 Table I Example Dye Color Yellow.
Violet.
Yellow.
'lliiodlphenyl-pp-dls-azo-bis salicylic acid 1:5-dl-ortho-sulpho-para-tolylaminoanthmquinone (C. I. 1,080).
Sodium salt of the toluene-para-sulphonyl ether of 4-para-hydro:q'benzcnc-azrrlpara-chloro-ortho-sulpho-phenyl-S-methyl- 5-l1ydroxy-pyrazol (C. I. 642). I
Table H Time to Fading Festness to Light (Hours) Rating Examples Aftcr- After- Control Treated Contiol Treated 3. 5 19 L2 L4 4.0 18 L2 L4 4. 5 19 L2 L4 While the process has been described with particular reference to basic cellulose acetate, it is applicable as well to other cellulose esters which have been modified to improve receptivity of acid dyes such as, for instance, cellulose propionate, butyrate, the mixed esters, the chloroform soluble tri-esters and the like where similar light-fastness problems are encountered.
Many equivalent modifications will be apparent to those skilled in the art without a departure from the inventive concept.
What is claimed is:
l. A process for the treatment of cellulose acetate which has been rendered acid dye sensitive by incorporating in it polymeric di-methyl amino ethyl methacrylate, which comprises dyeing the said cellulose acetate with an acid dye and thereafter contacting it at 212 F. for about at least 5 minutes with an aqueous solution containing about 15 grams of salicylic acid per liter of solution to render it light-fast.
2. The process of claim 1 wherein the cellulose acetate is in the form of a yarn.
3. The process of claim 2 wherein the acid dye is sulphonated 2-anilino quinizarin acid dye.
References Cited in the file of this patent UNITED STATES PATENTS Number Name Date 2,168,337 Heckert Aug. 8, 1939 2,376,891 Alles May 29, 1945
Claims (1)
1. A PROCESS FOR THE TREATMENT OF CELLULOSE ACETATE WHICH HAS BEEN RENDERED ACID DYE SENSITIVE BY INCORPORATING IN IT POLYMERIC DI-METHYL AMINO ETHYL METHACRYLATE, WHICH COMPRISES DYEING THE SAID CELLULOSE ACETATE WITH AN ACID DYE AND THEREAFTER CONTACTING IT AT 212* F. FOR ABOYT AT LEAST 5 MINUTES WITH AN AQUEOUS SOLUTION CONTAINING ABOUT 15 GRAMS OF SALICYLIC ACID PER LITER OF SOLUTION TO RENDER IT LIGHT-FAST.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US274510A US2690954A (en) | 1952-03-01 | 1952-03-01 | After-treatment of acid-dyed cellulose acetate with salicylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US274510A US2690954A (en) | 1952-03-01 | 1952-03-01 | After-treatment of acid-dyed cellulose acetate with salicylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2690954A true US2690954A (en) | 1954-10-05 |
Family
ID=23048492
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US274510A Expired - Lifetime US2690954A (en) | 1952-03-01 | 1952-03-01 | After-treatment of acid-dyed cellulose acetate with salicylic acid |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2690954A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2168337A (en) * | 1935-06-18 | 1939-08-08 | Du Pont | Cellulosic structure and method for preparing same |
| US2376891A (en) * | 1942-07-01 | 1945-05-29 | Du Pont | Cellulose ester manufacture |
-
1952
- 1952-03-01 US US274510A patent/US2690954A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2168337A (en) * | 1935-06-18 | 1939-08-08 | Du Pont | Cellulosic structure and method for preparing same |
| US2376891A (en) * | 1942-07-01 | 1945-05-29 | Du Pont | Cellulose ester manufacture |
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