US1041587A - Process of producing dyed cellulose ester. - Google Patents
Process of producing dyed cellulose ester. Download PDFInfo
- Publication number
- US1041587A US1041587A US70298912A US1912702989A US1041587A US 1041587 A US1041587 A US 1041587A US 70298912 A US70298912 A US 70298912A US 1912702989 A US1912702989 A US 1912702989A US 1041587 A US1041587 A US 1041587A
- Authority
- US
- United States
- Prior art keywords
- dyed
- cellulose
- cellulose ester
- dyed cellulose
- producing
- 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
- 238000000034 method Methods 0.000 title description 16
- 229920002678 cellulose Polymers 0.000 title description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000000975 dye Substances 0.000 description 13
- 239000001913 cellulose Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229940081735 acetylcellulose Drugs 0.000 description 3
- 229920002301 cellulose acetate Polymers 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PPKPKFIWDXDAGC-IHWYPQMZSA-N (z)-1,2-dichloroprop-1-ene Chemical compound C\C(Cl)=C\Cl PPKPKFIWDXDAGC-IHWYPQMZSA-N 0.000 description 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- WLKAMFOFXYCYDK-UHFFFAOYSA-N [5-amino-4-[[3-[(2-amino-4-azaniumyl-5-methylphenyl)diazenyl]-4-methylphenyl]diazenyl]-2-methylphenyl]azanium;dichloride Chemical compound [Cl-].[Cl-].CC1=CC=C(N=NC=2C(=CC([NH3+])=C(C)C=2)N)C=C1N=NC1=CC(C)=C([NH3+])C=C1N WLKAMFOFXYCYDK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- SUXCALIDMIIJCK-UHFFFAOYSA-L disodium;4-amino-3-[[4-[4-[(1-amino-4-sulfonatonaphthalen-2-yl)diazenyl]-3-methylphenyl]-2-methylphenyl]diazenyl]naphthalene-1-sulfonate Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(N=NC3=CC=C(C=C3C)C=3C=C(C(=CC=3)N=NC=3C(=C4C=CC=CC4=C(C=3)S([O-])(=O)=O)N)C)=CC(S([O-])(=O)=O)=C21 SUXCALIDMIIJCK-UHFFFAOYSA-L 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B3/00—Preparation of cellulose esters of organic acids
- C08B3/22—Post-esterification treatments, including purification
Definitions
- cellulose has first. been dyed and then etherized or prepared acetyl cellulose has been dyed by using swelling means or organic solvents whichareintended to produce receptivenes's of the cellulose esters which are otherwise indifferent to dyes.
- the present process dyed cellulose esters which are exceedingly fast against light and washing are produced in a single process the dye being dissolved for example directly in the acidylizing mixture or in a portion of the acetic acid and thereafter the cellulose, hydroor oxy-cellulose (hereinafter-referred to as a cellulosic material) isbrought into this coloring solution by heating.
- a cellulosic material hydroor oxy-cellulose
- the dyed celluloseproducts pass clearly into the solution and can be further treated without alteration of the tint.
- acetic acid which contains 2% of concentrated sulfuric acid
- a solution of a dye such for example as Bismarck brown in 100 parts of acetic acid is added and the whole mass is heated in the water bath until a clear brown solution is produced.
- a process of producing dyed cellulose esters comprising the simultaneous treatment of a cellulosic material with a suitable dye and an acidylizing agent.
- a process of producing dyed cellulose acetate comprising the simultaneous treatment of a cellulosic material with a suitable dye and an acetylizing agent.
- Aprocess of producing dyed cellulose esters comprising the simultaneous treatment of cellulose with a suitable dye and an acidylizing agent.
- a process of producing dyed cellulose esters comprising the simultaneous treatment of a cellulosic material with a suitable dye and a mixture of acetic acid, acetic anhydrid and sulfuric acid.
- a process of producing dyed cellulose esters-said process comprising the simulta- I neous treatment of a cellulosicmaterial with an acid-soluble dye and an acidylizing agent.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
BEN-NO IBORZYKOWSKI, F CHARLOZITENBUBG, GERMANY.
rnocns s or rnonuctne DYED CELLULOSE ESTER.
1,041,587; No Drawing.
To all whom it m ay concern:
Be it known that I, BENNO BoRzYKow- SKI. a subject of the Emperor of Russia, and
resident of Charlottenburg, Germany, have invented a certain new and useful Improvement in Processes of Producing Dyed Cellulose Ester, of which the following is a specification.
Several processes are already known for dyeing acetyl cellulose or for producing it in a dyed condition. For example cellulose has first. been dyed and then etherized or prepared acetyl cellulose has been dyed by using swelling means or organic solvents whichareintended to produce receptivenes's of the cellulose esters which are otherwise indifferent to dyes.
In accordanceflwith .the present process dyed cellulose esters which are exceedingly fast against light and washing are produced in a single process the dye being dissolved for example directly in the acidylizing mixture or in a portion of the acetic acid and thereafter the cellulose, hydroor oxy-cellulose (hereinafter-referred to as a cellulosic material) isbrought into this coloring solution by heating. As there are now a large number of fastdyes which resist acids. by
the use of such suitable dyes. products brightly dyed and of exceedingly fast properties are produced by this very simple process without special precautionary measures.
introducing such 'a dyed-solution of formyla a'cetylor .propionyl-cellulose, etc., into one of the usual precipitating media such as water, benzol, alcohol and so on abrightand clearly dyed product in the desired form such as yarn, film, etc., which do not bleedin the precipitating bath, do not 7 give up the dye on further treatment, and
possess the same strength as in the uncolored condition. On treatment with the usual solvents such for example as chloroform,-
acetone, dichlor'ethylene, etc., the dyed celluloseproducts pass clearly into the solution and can be further treated without alteration of the tint.
I Example: 100 parts of cleaned and dried cotton is introduced and stirred into a mixture of 450 parts of acetic acid anhydrid and Specification of Letters Patent. Application filed l l'une 11, 1912. Serial No. 702,989.
Patented Oct. 15,1912.
400 parts of acetic acid which contains 2% of concentrated sulfuric acid; at the same time a solution of a dye such for example as Bismarck brown in 100 parts of acetic acid is added and the whole mass is heated in the water bath until a clear brown solution is produced.
Instead of dissolying the dye separately itcan be added directly to the acetylizing mixture and can be stirred in. The same results are obtained when the dye is added before heating or to the-prepared acetylizing mass.
The same process is carried out with other dyes. as, for example, metanile yellow, chrysophenin G, fastscarlet colors, substantive blacks, etc. l
The solutions of' dyed acidylized cellulose thus obtained can be further treated directly. T
1. A process of producing dyed cellulose esters, said process comprising the simultaneous treatment of a cellulosic material with a suitable dye and an acidylizing agent.
2. A process of producing dyed cellulose acetate, said process comprising the simultaneous treatment of a cellulosic material with a suitable dye and an acetylizing agent.
Aprocess of producing dyed cellulose esters. said process comprising the simultaneous treatment of cellulose with a suitable dye and an acidylizing agent.
4. A process of producing dyed cellulose esters, said process comprising the simultaneous treatment of a cellulosic material with a suitable dye and a mixture of acetic acid, acetic anhydrid and sulfuric acid.
5. A process of producing dyed cellulose esters-said process comprising the simulta- I neous treatment of a cellulosicmaterial with an acid-soluble dye and an acidylizing agent.
In testimony whereof I have signed my name to this specification in the prewng of two subscribing witnesses.
, BENNO BORZYKOWSKI.
\ Witnesses: v
' CLARENCE CoRRIoAN,
Martins Hammer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70298912A US1041587A (en) | 1912-06-11 | 1912-06-11 | Process of producing dyed cellulose ester. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70298912A US1041587A (en) | 1912-06-11 | 1912-06-11 | Process of producing dyed cellulose ester. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1041587A true US1041587A (en) | 1912-10-15 |
Family
ID=3109862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US70298912A Expired - Lifetime US1041587A (en) | 1912-06-11 | 1912-06-11 | Process of producing dyed cellulose ester. |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1041587A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2673202A (en) * | 1951-11-14 | 1954-03-23 | Eastman Kodak Co | Method for the manufacture of high acetyl cellulose acetate |
-
1912
- 1912-06-11 US US70298912A patent/US1041587A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2673202A (en) * | 1951-11-14 | 1954-03-23 | Eastman Kodak Co | Method for the manufacture of high acetyl cellulose acetate |
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