US1900168A - Camille dreyfus - Google Patents
Camille dreyfus Download PDFInfo
- Publication number
- US1900168A US1900168A US1900168DA US1900168A US 1900168 A US1900168 A US 1900168A US 1900168D A US1900168D A US 1900168DA US 1900168 A US1900168 A US 1900168A
- Authority
- US
- United States
- Prior art keywords
- per litre
- cellulose
- fabric
- dyeing
- grams per
- 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 56
- 239000000463 material Substances 0.000 description 50
- 239000004744 fabric Substances 0.000 description 42
- 229920002678 cellulose Polymers 0.000 description 34
- 238000004043 dyeing Methods 0.000 description 28
- 238000000034 method Methods 0.000 description 28
- 229910000029 sodium carbonate Inorganic materials 0.000 description 28
- 235000017550 sodium carbonate Nutrition 0.000 description 28
- 229920002301 Cellulose acetate Polymers 0.000 description 26
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 24
- 239000001913 cellulose Substances 0.000 description 20
- JBUKJLNBQDQXLI-UHFFFAOYSA-N Sodium perborate Chemical compound [Na+].[Na+].O[B-]1(O)OO[B-](O)(O)OO1 JBUKJLNBQDQXLI-UHFFFAOYSA-N 0.000 description 18
- 229960001922 sodium perborate Drugs 0.000 description 18
- 239000000975 dye Substances 0.000 description 14
- 239000004753 textile Substances 0.000 description 14
- 239000000984 vat dye Substances 0.000 description 14
- 239000003513 alkali Substances 0.000 description 10
- 239000010977 jade Substances 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- 239000003518 caustics Substances 0.000 description 6
- 239000003086 colorant Substances 0.000 description 6
- 150000002895 organic esters Chemical class 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 238000007127 saponification reaction Methods 0.000 description 6
- 210000002268 Wool Anatomy 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 229920003086 cellulose ether Polymers 0.000 description 4
- 230000004059 degradation Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000001590 oxidative Effects 0.000 description 4
- PNIJRIIGBGFYHF-UHFFFAOYSA-N perborate(2-) Chemical compound O[B-]1(O)OO[B-](O)(O)OO1 PNIJRIIGBGFYHF-UHFFFAOYSA-N 0.000 description 4
- 240000000800 Allium ursinum Species 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- UHOKSCJSTAHBSO-UHFFFAOYSA-N Indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 description 2
- 101710022641 SLC26A6 Proteins 0.000 description 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L Sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 2
- DQEFEBPAPFSJLV-WLTGXWPBSA-N [(2R,3R,4S,5R,6S)-4,5,6-tri(propanoyloxy)-3-[(2S,3R,4S,5R,6R)-3,4,5-tri(propanoyloxy)-6-(propanoyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl propanoate Chemical compound CCC(=O)OC[C@H]1O[C@@H](OC(=O)CC)[C@H](OC(=O)CC)[C@@H](OC(=O)CC)[C@@H]1O[C@H]1[C@H](OC(=O)CC)[C@@H](OC(=O)CC)[C@H](OC(=O)CC)[C@@H](COC(=O)CC)O1 DQEFEBPAPFSJLV-WLTGXWPBSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 230000002939 deleterious Effects 0.000 description 2
- -1 for example Polymers 0.000 description 2
- 235000019239 indanthrene blue RS Nutrition 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000006011 modification reaction Methods 0.000 description 2
- 235000012736 patent blue V Nutrition 0.000 description 2
- 230000000750 progressive Effects 0.000 description 2
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
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/22—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using vat dyestuffs including indigo
-
- 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
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/22—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using vat dyestuffs including indigo
- D06P1/221—Reducing systems; Reducing catalysts
-
- 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
- This invention relates to a process of dyetextile materials made of or containing derivatives of cellulose, particularly vat colors to obing organic cellulose acetate, utilizing tain good fast dyeings.
- caustic-alkali which has a deleterious effect upon fibres made of or containing organic esters of cellulose and also upon animal fibres such as wool and silk. effects a degradation of the animal fibres with a consequent loss in strength and contraction of the fibres and with the cellulose acetate or other cellulose esters not only results in a progressive loss in weight and some loss in lustre and strength but also affects the dyeing properties of the cellulose esters- According to the present invention the vat dyes are employed but their application is effected in such a manner that the use of caustic alkali is entirely or almost entirely dispensed with.
- vat dyes are applied to material containing cellulose derivatives in the manner in which they are-customarily applied with the exception that little or no caustic alkali is added to the dyeing bath and the amount of hydrosul- The caustic alkali Serial No. 375,571.
- phite usually employed is increased.
- the absence of alkali or its presence in very small quantities permits the dyeing of cellulose esters, for example, cellulose acetate, to be effected without the usual objectionable saponification.
- the cellulosic material thus retains all of its desirable qualities such as lustre, strength and hand.
- the process consists essentially in treating material containing cellulose acetate in a bath containing, in addition to the vat color, hydrosulphite and soda ash invarying amounts, depending upon the depth of color desired and the particular dyestuif employed. Excellent dyeings are obtained by this method if the dyeing operation is carried out at approximately 75 C. for about one-half to one hour or until the desired shade is ob- ,tained.
- the material is then rinsed and subsequently oxidized by exposure to the atmosphere or preferably by treating the same for about 15 minuts at 60 C. in a bath containing 2 grams per litre of sodium perborate. The oxidation with perborate results in brighterdyeings.
- the material can then advantageously be subjected to a light soaping treatment.
- Emamp Ze I and very fast to light was obtained.
- Example I l A cellulose acetate fabric was treated as outlined in Example I except that no soda ash was added to the bath. The fabric was dyed in fullshade and its fastness properties wereo'fully as good as under Example I.
- Example [H A fabric containing methyl cellulose was treated with 5% Anthrene blue green B C. I. 1102 in a 40 1. bath containing 10 grams hydrosulphite per litre and 2 grams soda ash per litre. The fabric was dyed for one hour at 75 C. and was then oxidized as outlined under Example I. A full level blue green was obtained on the fabric, the coloring possessing very good fastness to light and washlng. 1
- Example V i A cellulose acetate fabric was treated with 5% Ponsol violet RRD C. I. 1104 in a 40:1 bath containing 5 to 10 grams hydrosulphite per litre and 0.5 rams soda ash per litre for one hour at 75 The fabric was then removed from the bath, rinsed and treated for about 15 minutes at 60 .C. in a bath containing 2 grams per litre sodium perborate. The fabric was dyed a full violet, level and was fast to light and washing.
- Ewample VI A cellulose propionate fabric was scoured in the usual manner and then dyed with 5% Anthrene Jade green in a 40 1 bath containing 5 to 10 grams of hydrosulphite per litre and 0.5 grams soda ash per litre. The fabric was dyed for one hour at 75 C. andwas then oxidized in a 2 grams per litre sodium perborate solution at 60 C. for about 15 minutes. A full level dyeing, washable and very fast to light was obtained.
- E xample VII Ewample VIII A cellulose acetate fabric was scoured in the'normal manner and then dyed with 5% Ciba yellow Gina 40:1 bath containing 5 to 10 grams of hydrosulphite per litre and 0.5 grams soda ash per litre. The fabric was dyed for one hour ,at C. and was then oxidized in a 2 grams per litre sodium perborate solution at 60 C. for about 15 minutes. The fabric was dyed a full level medium pure yellow which was fast to light and washing.
- Example X A fabric containing cellulose acetate was dyed with 1% Anthrene blue green B, 0.2% Ponsol violet RED in a 40: 1 bath containing 10 grams per litre of sodium hydrosulphite and 0.5 grams per litre soda ash for A,, to 1 hour at 75 C. The fabric was thenrinsed and oxidized in a 2 grams per litre sodium perborate solution for 15 minutes at 60 C. The fabric was dyed sky blue and was fast to Washing and light.
- the process is not limited to fabrics made wholly of organic derivatives of cellulose but is applicable to fabrics containing cellulose esters in conjunction with wool, and/or silk, and/or cotton and/or taming organic sired.
- the process is also applicable to ma terials made of or containing cellulose esters which have been iron-proofed or partially saponified.
- Process of dyeing textile materials conderivatives of cellulose which comprises treating said material in a. dye bath containing a vat dye, comparatively large amounts of hydrosulphite and small amounts of soda ash.
- Process of dyeing textile materials containing cellulose acetate which comprises treating said material in a dye bath containing a vat dye, comparatively large amounts ofhhydrosulphite and small amounts of soda as 4.
- Process of dyeing textile materials containing organic esters of cellulose which comprises treating said material in adye bath containing 5% Anthrene Jade green, 5 to 10 grams per litre of hydrosulphite and 0.5 grams per litre of soda ash for one half to one hour at C., rinsing the thus treated material and then subjecting the same to an oxidizing action.
- Process of dyeing textile materials containing cellulose acetate which comprises treating said material in a dye bath containing 5% Anthrene Jade green, 10 grams per litre of hydrosulphite and 0.5 grams per litre of soda ash for one half to one hour at 75 (1.,
- Process of dyeing textile materials containing cellulose acetate which comprises treating said material in a dye bath containing 5% Anthrene Jade green, 10 grams per litre of hydrosulphite and 0.5 grams per litre of soda ash for one half to one'hour at 75 0., rinsing the thus treated material and then subjecting the same to the action of a two gram per litre sodium perborate solution at 6 C. .for about 15 minutes. 7
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
Description
1 tionable proportions.
Patented Mar. 7, 1933 v UNITED STATES PATENT OFFICE GAMILLE DREYFUS,
or NEW YORK, N. Y.,
AND HERBERT PLATT, OF CUMBERLAND,
MARYLAND, ASSIGNORS TO CELANESE CORPORATION OF AMERICA, A CORPORATION OF DELAWARE DYEING- OF TEXTILE MATERIAL WITH VAT DYES No Drawing. Application filed July 2,
This invention relates to a process of dyetextile materials made of or containing derivatives of cellulose, particularly vat colors to obing organic cellulose acetate, utilizing tain good fast dyeings.
An object of our invention is to utilize vat dyestuffs for the dyeing of cellulose esters and cellulose ethers, specifically cellulose acetate. Another object of this invention is to devise a process for the dyeing of organic derivatives of cellulose with vat dyes Without materials has been difiicult when it has not been altogether impossible. This difiiculty was due to the presence of large amounts of.
caustic-alkali which has a deleterious effect upon fibres made of or containing organic esters of cellulose and also upon animal fibres such as wool and silk. effects a degradation of the animal fibres with a consequent loss in strength and contraction of the fibres and with the cellulose acetate or other cellulose esters not only results in a progressive loss in weight and some loss in lustre and strength but also affects the dyeing properties of the cellulose esters- According to the present invention the vat dyes are employed but their application is effected in such a manner that the use of caustic alkali is entirely or almost entirely dispensed with. This modification precludes the usual degradation or saponification or at least reduces the same to unobjec- This variation of the process of applying vat colors to organicderivatives of'cellulose gives colorings which are bright and permanent in nature, being fast to light and washing. I
In accordance with our invention the vat dyes are applied to material containing cellulose derivatives in the manner in which they are-customarily applied with the exception that little or no caustic alkali is added to the dyeing bath and the amount of hydrosul- The caustic alkali Serial No. 375,571.
phite usually employed is increased. The absence of alkali or its presence in very small quantities permits the dyeing of cellulose esters, for example, cellulose acetate, to be effected without the usual objectionable saponification. The cellulosic material thus retains all of its desirable qualities such as lustre, strength and hand.
The process consists essentially in treating material containing cellulose acetate in a bath containing, in addition to the vat color, hydrosulphite and soda ash invarying amounts, depending upon the depth of color desired and the particular dyestuif employed. Excellent dyeings are obtained by this method if the dyeing operation is carried out at approximately 75 C. for about one-half to one hour or until the desired shade is ob- ,tained. The material is then rinsed and subsequently oxidized by exposure to the atmosphere or preferably by treating the same for about 15 minuts at 60 C. in a bath containing 2 grams per litre of sodium perborate. The oxidation with perborate results in brighterdyeings. The material can then advantageously be subjected to a light soaping treatment.
In order to illustrate our invention but with no intention of limiting ourselves thereto, the following speclfic examples are given. I
Emamp Ze I and very fast to light, was obtained.
Example I l A cellulose acetate fabric was treated as outlined in Example I except that no soda ash was added to the bath. The fabric was dyed in fullshade and its fastness properties wero'fully as good as under Example I.
Example [H A fabric containing methyl cellulose was treated with 5% Anthrene blue green B C. I. 1102 in a 40 1. bath containing 10 grams hydrosulphite per litre and 2 grams soda ash per litre. The fabric was dyed for one hour at 75 C. and was then oxidized as outlined under Example I. A full level blue green was obtained on the fabric, the coloring possessing very good fastness to light and washlng. 1
Ea-ample [V A fabric containing cellulose acetate'was treated. with 5% Anthrene blue green B in a 10:1 bath containing 5 to 10 grams of hydrosulphite per litre, and 0.5 grams per litre soda ash. The fabric was dyed for one hour at 75 C. and was then oxidized in a 2 grams per litre sodium perborate solution at 60 C. for about 15 minutes. The fabric was dyed a medium greenish blue fast to light and washing.
Example V i A cellulose acetate fabric was treated with 5% Ponsol violet RRD C. I. 1104 in a 40:1 bath containing 5 to 10 grams hydrosulphite per litre and 0.5 rams soda ash per litre for one hour at 75 The fabric was then removed from the bath, rinsed and treated for about 15 minutes at 60 .C. in a bath containing 2 grams per litre sodium perborate. The fabric was dyed a full violet, level and was fast to light and washing.
Ewample VI A cellulose propionate fabric was scoured in the usual manner and then dyed with 5% Anthrene Jade green in a 40 1 bath containing 5 to 10 grams of hydrosulphite per litre and 0.5 grams soda ash per litre. The fabric was dyed for one hour at 75 C. andwas then oxidized in a 2 grams per litre sodium perborate solution at 60 C. for about 15 minutes. A full level dyeing, washable and very fast to light was obtained.
E xample VII Ewample VIII A cellulose acetate fabric was scoured in the'normal manner and then dyed with 5% Ciba yellow Gina 40:1 bath containing 5 to 10 grams of hydrosulphite per litre and 0.5 grams soda ash per litre. The fabric was dyed for one hour ,at C. and was then oxidized in a 2 grams per litre sodium perborate solution at 60 C. for about 15 minutes. The fabric was dyed a full level medium pure yellow which was fast to light and washing.
E wample [X Example X A fabric containing cellulose acetate was dyed with 1% Anthrene blue green B, 0.2% Ponsol violet RED in a 40: 1 bath containing 10 grams per litre of sodium hydrosulphite and 0.5 grams per litre soda ash for A,, to 1 hour at 75 C. The fabric was thenrinsed and oxidized in a 2 grams per litre sodium perborate solution for 15 minutes at 60 C. The fabric was dyed sky blue and was fast to Washing and light.
In none of the above examples was there any appreciable saponification of the cellulose esters. The dyeings obtained by the processes outlined in the above examples were extremely fast to light and in most instances were unaffected after exposure in a fadeometer for 75 hours plus. The oxidation with sodium perborate may be omitted where de sired and the oxidation efiected by exposure to the atmosphere but where bright shades are desired the perborate treatment is recom-:
mended.
,Where it is desired to employ a shading agent with the vat colors enumerated Newport Indanthrene Direct Black RB Paste may be employed.
The above examples are merely given by way of illustration and the invention is not to be considered as limited to the particular dyestufl's enumerated. Any of the so-called vat dyes which have an affinity. for cellulose esters or ethers may be employed. In addition to the dyes named in the examples, the following are given as further typical examples of suitable dyestufi's: Ciba blue G C. I. 1185, Algol yellow B C. I. 1132, Anthrene brown BB 0. 1.1120, Ponsol green BN C. I. 1102. i
In like manner the process is not limited to fabrics made wholly of organic derivatives of cellulose but is applicable to fabrics containing cellulose esters in conjunction with wool, and/or silk, and/or cotton and/or taming organic sired. The process is also applicable to ma terials made of or containing cellulose esters which have been iron-proofed or partially saponified.
Having claim and desire to secure entis:
described our invention what we by Letters Pat- 1. Process of dyeing textile materials a 5 which comprises treating 'said material in a dye bath containing a vat dye, comparatively large amounts of hydrosulphite and small amounts of soda ash.
'2. Process of dyeing textile materials conderivatives of cellulose which comprises treating said material in a. dye bath containing a vat dye, comparatively large amounts of hydrosulphite and small amounts of soda ash.
3. Process of dyeing textile materials containing cellulose acetate which comprises treating said material in a dye bath containing a vat dye, comparatively large amounts ofhhydrosulphite and small amounts of soda as 4. Process of dyeing textile materials containing organic esters of cellulose which comprises treating said material in adye bath containing 5% Anthrene Jade green, 5 to 10 grams per litre of hydrosulphite and 0.5 grams per litre of soda ash for one half to one hour at C., rinsing the thus treated material and then subjecting the same to an oxidizing action.
5. Process of dyeing. textile materials containing organic esters of cellulose which comprises treating said material in a dye bath containing 5% Anthrene Jade green, 5 to 10 grams per litre of hydrosulphite and 0.5 grams per litre of soda ash for one half to one hour at 75 C., rinsing the thus treated material and then subjecting the same to the action of a two gram per litre sodium perborate solution at 60 C. for about 15 minutes.
6. Process of dyeing textile materials containing cellulose acetate which comprises treating said material in a dye bath containing 5% Anthrene Jade green, 10 grams per litre of hydrosulphite and 0.5 grams per litre of soda ash for one half to one hour at 75 (1.,
rinsing the thus treated material and then.
subjecting the same to an oxidizing action.
7. Process of dyeing textile materials containing cellulose acetate which comprises treating said material in a dye bath containing 5% Anthrene Jade green, 10 grams per litre of hydrosulphite and 0.5 grams per litre of soda ash for one half to one'hour at 75 0., rinsing the thus treated material and then subjecting the same to the action of a two gram per litre sodium perborate solution at 6 C. .for about 15 minutes. 7
In testimony whereof, we have hereunto subscribed our names.
CAMILLE DREYFUS. HERBERT PLATT.
so. I
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1900168A true US1900168A (en) | 1933-03-07 |
Family
ID=3425009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US1900168D Expired - Lifetime US1900168A (en) | Camille dreyfus |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1900168A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2524093A (en) * | 1948-04-20 | 1950-10-03 | Celanese Corp | Union dyeing of mixed fabrics of cellulose ester and animal fibers with alkaline reduced vat dye solutions containing swelling agents |
| US2528614A (en) * | 1946-10-02 | 1950-11-07 | Celanese Corp | Vat dyeing process for cellulose acetate textile material |
| US2774647A (en) * | 1952-05-17 | 1956-12-18 | American Cyanamid Co | Dyeing of polyesters with vat dyes |
| US2774649A (en) * | 1952-05-17 | 1956-12-18 | American Cyanamid Co | Dyeing of cellulose carboxylic acid esters with vat dyes |
-
0
- US US1900168D patent/US1900168A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2528614A (en) * | 1946-10-02 | 1950-11-07 | Celanese Corp | Vat dyeing process for cellulose acetate textile material |
| US2524093A (en) * | 1948-04-20 | 1950-10-03 | Celanese Corp | Union dyeing of mixed fabrics of cellulose ester and animal fibers with alkaline reduced vat dye solutions containing swelling agents |
| US2774647A (en) * | 1952-05-17 | 1956-12-18 | American Cyanamid Co | Dyeing of polyesters with vat dyes |
| US2774649A (en) * | 1952-05-17 | 1956-12-18 | American Cyanamid Co | Dyeing of cellulose carboxylic acid esters with vat dyes |
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