US1908993A - Process for dyeing cellulose acetate silk - Google Patents
Process for dyeing cellulose acetate silk Download PDFInfo
- Publication number
- US1908993A US1908993A US42046A US4204625A US1908993A US 1908993 A US1908993 A US 1908993A US 42046 A US42046 A US 42046A US 4204625 A US4204625 A US 4204625A US 1908993 A US1908993 A US 1908993A
- Authority
- US
- United States
- Prior art keywords
- cellulose acetate
- acetate silk
- cellulose
- dyeing
- dyeing cellulose
- 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
- 229920002301 cellulose acetate Polymers 0.000 title description 11
- 238000004043 dyeing Methods 0.000 title description 9
- 238000000034 method Methods 0.000 title description 6
- 229940081735 acetylcellulose Drugs 0.000 description 10
- 239000002699 waste material Substances 0.000 description 9
- 229920002678 cellulose Polymers 0.000 description 7
- 239000001913 cellulose Substances 0.000 description 7
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 6
- 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 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- FGLPIWSCAOGYBA-UHFFFAOYSA-N 8-nitronaphthalen-2-amine Chemical compound C1=CC=C([N+]([O-])=O)C2=CC(N)=CC=C21 FGLPIWSCAOGYBA-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- ZXPXRBDYCANCCU-UHFFFAOYSA-N 3-aminobenzo[b]phenalen-7-one Chemical compound C12=CC=CC=C2C(=O)C2=CC=CC3=C2C1=CC=C3N ZXPXRBDYCANCCU-UHFFFAOYSA-N 0.000 description 1
- WTZQJWITZKKMAB-UHFFFAOYSA-N 9h-carbazole-1-sulfonic acid Chemical class C12=CC=CC=C2NC2=C1C=CC=C2S(=O)(=O)O WTZQJWITZKKMAB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- WBIPGYLOZIJNQV-UHFFFAOYSA-N formaldehyde sulfuric acid Chemical compound C=O.C=O.OS(O)(=O)=O WBIPGYLOZIJNQV-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- -1 hydrocarbons sulfonic acids Chemical class 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- CKIGNOCMDJFFES-UHFFFAOYSA-N n-naphthalen-2-yl-1-phenylmethanimine Chemical compound C=1C=C2C=CC=CC2=CC=1N=CC1=CC=CC=C1 CKIGNOCMDJFFES-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 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
- D06P3/42—Cellulose acetate using dispersed dyestuffs
-
- 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
- D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
- D06P1/46—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing natural macromolecular substances or derivatives thereof
- D06P1/48—Derivatives of carbohydrates
- D06P1/50—Derivatives of cellulose
-
- 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
- Y10S8/908—Anionic emulsifiers for dyeing
- Y10S8/909—Sulfonated or sulfated alphatic hydrocarbons
-
- 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
- the present invention has for its object to provide for an improved process for dyeing cellulose acetate silk.
- the compounds dyed with the aid of the aforesaid sulfite cellulose waste liquor may be coloring matters or colored or anic compounds in general, insoluble or di cultly soluble in water, as well as components of dyestufi's, such for example as amino compounds which afterwards are diazotized on the fibre and. coupled with suitable components, or naphthols or similar components which afterwards are to be developed with diazo compounds. s
- the compounds to be brought on the fibre may be first made into a concentrated solution or paste, generally of a colloidal nature, or otherwise finely dispersed in a concentrated form by an addition of sulfite cellulose waste liquor either alone or in association with one or more of the so-called synthetic tans, such as substances of the nature of phenol- (or cresol-) formaldehyde-sulfuric acid condensation products, or phenolsulfonic acid-sulfur condensation products, carbazol sulfonic acids, crude anthracene or other high tar hydrocarbons sulfonic acids,
- synthetic tans such as substances of the nature of phenol- (or cresol-) formaldehyde-sulfuric acid condensation products, or phenolsulfonic acid-sulfur condensation products, carbazol sulfonic acids, crude anthracene or other high tar hydrocarbons sulfonic acids,
- a dye-bath prepared by diluting such concentrated preparation,or the dyebath may be directly prepared with the compounds to be brought on the fibre while adding sulfite cellulose waste liquor either alone or with the of ordinary temperature. 100 parts of acetate silk are dyed in the bath for one hour at the said temperature, rinsed and dried, handsome golden yellow shades being obtained.
- coloring matters dilficultly soluble in water which may be employed for dyeingcellulose acetate silk in the manner hereinbefore described may be mentioned, for instance the condensation product of 3-chlor- (i-nitro-l-amino-benzene and formaldehyde (sec U. S.
- Patent 932,266, dated August 22, 1909 1.4-diamino-anthraquinone, 1.4.5.8- tetra-amino-anthraquinone, 3-aminobenzanthrone, .Bz l-aminobenzanthrone correspond ing to the formula alpha naphthylamine (diaz) +meta-phenylene-diamine, beta amino-alpha-naphthraqum one, 8-nitro-2-amino-naphthalene, -nitro-1.4- diaminoanthraquinone, methyl violet base, alpha naphthylamine (diaz) para-hydroxybcnzoic acid.
- Example 2 parts of 8-nitro-2-amino naphthalene are Well mixed with parts of concentrated sul fite cellulose waste liquor of between and and passed into 2000 parts of water a colloidal preparation from an inter'mixture of aminoanthraquinones having an aifinity for acetyl cellulose with waste sulfite liquor.
- the process of producing dyeings on cellulose acetate silk which comprises employing a substance suitable for dyeing acetate silk difficulty soluble in water, the -said substance containing in its molecule at least one aromatic nucleus and at least one nitrogen atom 'which is fixed to an aromatic nucleus and otherwise connected with atoms of elements selected from the roup consisting of carbon, nitrogen and ydrogen, in conjunction with sulphite cellulose waste liquor.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Coloring (AREA)
Description
Patented May 16, 1933 UNITED. STAT WARE ES PATENT OFFICE RICHARD METZGEB, OF HEIDELBERG, GERMANY, ASSIGNOB, BY MESNE ASSIGNMENTS; TO GENEBA}; ANILINE WORKS, INC., OF NEW YORK, N. Y., A CORPORATION OF DELA- rnocnss FOR DYEING GELLULOSE ACETATE Sm:
No Drawing. Application filed July 7, 1925, Serial No. 42,046,41141 in Germany July 11, 192;.
The present invention has for its object to provide for an improved process for dyeing cellulose acetate silk.
I have found that cellulose acetate silkcan be dyed in a very excellent and improved manner with a great number of insoluble or difiicultly soluble compounds when dyeing is carried out in the presence of su'lfite cellulose waste liquor.
The compounds dyed with the aid of the aforesaid sulfite cellulose waste liquor may be coloring matters or colored or anic compounds in general, insoluble or di cultly soluble in water, as well as components of dyestufi's, such for example as amino compounds which afterwards are diazotized on the fibre and. coupled with suitable components, or naphthols or similar components which afterwards are to be developed with diazo compounds. s
For dyeing, the compounds to be brought on the fibre may be first made into a concentrated solution or paste, generally of a colloidal nature, or otherwise finely dispersed in a concentrated form by an addition of sulfite cellulose waste liquor either alone or in association with one or more of the so-called synthetic tans, such as substances of the nature of phenol- (or cresol-) formaldehyde-sulfuric acid condensation products, or phenolsulfonic acid-sulfur condensation products, carbazol sulfonic acids, crude anthracene or other high tar hydrocarbons sulfonic acids,
or sulfonated mineral oils and the like, and
a dye-bath prepared by diluting such concentrated preparation,or the dyebath may be directly prepared with the compounds to be brought on the fibre while adding sulfite cellulose waste liquor either alone or with the of ordinary temperature. 100 parts of acetate silk are dyed in the bath for one hour at the said temperature, rinsed and dried, handsome golden yellow shades being obtained.
As examples of coloring matters dilficultly soluble in water which may be employed for dyeingcellulose acetate silk in the manner hereinbefore described may be mentioned, for instance the condensation product of 3-chlor- (i-nitro-l-amino-benzene and formaldehyde (sec U. S. Patent 932,266, dated August 22, 1909), 1.4-diamino-anthraquinone, 1.4.5.8- tetra-amino-anthraquinone, 3-aminobenzanthrone, .Bz l-aminobenzanthrone correspond ing to the formula alpha naphthylamine (diaz) +meta-phenylene-diamine, beta amino-alpha-naphthraqum one, 8-nitro-2-amino-naphthalene, -nitro-1.4- diaminoanthraquinone, methyl violet base, alpha naphthylamine (diaz) para-hydroxybcnzoic acid.
WVhat I claim is:
1. The herein described process for the production of tints on acetyl cellulose, which comprises treating the acetyl cellulose with a colloidal preparation from an intermixture of insoluble amino-azo-dyestufi's having an affinity for acetyl cellulose with waste sulfite li uor. J
2. The herein described process for the production of tints on acetyl cellulose, which addition of a sulfonic a d the comprises treating the acetyl cellulose with character.
The following example will serve to further illustrate my present invention which however is not restricted thereto. The parts are by weight.
Example 2 parts of 8-nitro-2-amino naphthalene are Well mixed with parts of concentrated sul fite cellulose waste liquor of between and and passed into 2000 parts of water a colloidal preparation from an inter'mixture of aminoanthraquinones having an aifinity for acetyl cellulose with waste sulfite liquor.
3. The process of producing dyeings on cellulose acetate silk which comprises employing a substance suitable for dyeing acetate silk difficulty soluble in water, the -said substance containing in its molecule at least one aromatic nucleus and at least one nitrogen atom 'which is fixed to an aromatic nucleus and otherwise connected with atoms of elements selected from the roup consisting of carbon, nitrogen and ydrogen, in conjunction with sulphite cellulose waste liquor.
' 4. The process of producing'dyeings on' cellulose acetate silk which comprises n1ploying a substance suitable for dyeing acetate 4 silk, difliculty soluble in watcrselected from the group consisting of ainino-azo-ilyestufi's and ainino-anthraquinones in conjunction with sulpliite cellulose waste liquor.
In testimony whereof I have hereunto set my hand. 1
RICHARD METZGER.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1908993X | 1924-07-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1908993A true US1908993A (en) | 1933-05-16 |
Family
ID=7748804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US42046A Expired - Lifetime US1908993A (en) | 1924-07-11 | 1925-07-07 | Process for dyeing cellulose acetate silk |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1908993A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2574597A (en) * | 1949-03-03 | 1951-11-13 | Celanese Corp | Spray-dried dyestuff powders comprising lignin sulfonate |
| US2734793A (en) * | 1956-02-14 | Method of preparing water-dispersible |
-
1925
- 1925-07-07 US US42046A patent/US1908993A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2734793A (en) * | 1956-02-14 | Method of preparing water-dispersible | ||
| US2574597A (en) * | 1949-03-03 | 1951-11-13 | Celanese Corp | Spray-dried dyestuff powders comprising lignin sulfonate |
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