DE1011869B - Verfahren zur Veredelung von Cellulose oder Cellulosederivaten - Google Patents
Verfahren zur Veredelung von Cellulose oder CellulosederivatenInfo
- Publication number
- DE1011869B DE1011869B DEF17948A DEF0017948A DE1011869B DE 1011869 B DE1011869 B DE 1011869B DE F17948 A DEF17948 A DE F17948A DE F0017948 A DEF0017948 A DE F0017948A DE 1011869 B DE1011869 B DE 1011869B
- Authority
- DE
- Germany
- Prior art keywords
- cellulose
- hours
- copper
- solution
- carbodiimide
- 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.)
- Pending
Links
- 229920002678 cellulose Polymers 0.000 title claims description 22
- 239000001913 cellulose Substances 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 8
- 150000001718 carbodiimides Chemical class 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 6
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical group [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 6
- 150000001879 copper Chemical class 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 239000000975 dye Substances 0.000 description 18
- 230000002378 acidificating effect Effects 0.000 description 16
- 235000010980 cellulose Nutrition 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000010949 copper Substances 0.000 description 9
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 8
- 229920002301 cellulose acetate Polymers 0.000 description 8
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229920000297 Rayon Polymers 0.000 description 7
- DBNPDRYVYQWGFW-UHFFFAOYSA-N N.[Cu]=O Chemical compound N.[Cu]=O DBNPDRYVYQWGFW-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000002964 rayon Substances 0.000 description 6
- 210000002268 wool Anatomy 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- -1 Isourea ethers Chemical class 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- LPMDNOPQLGRDMA-UHFFFAOYSA-N n'-butylmethanediimine Chemical compound CCCCN=C=N LPMDNOPQLGRDMA-UHFFFAOYSA-N 0.000 description 3
- 239000004627 regenerated cellulose Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229920002955 Art silk Polymers 0.000 description 2
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229920003086 cellulose ether Polymers 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- XSYIZNZEZNDTPC-UHFFFAOYSA-N n-butyl-n'-cyclohexylmethanediimine Chemical compound CCCCN=C=NC1CCCCC1 XSYIZNZEZNDTPC-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- YBVPWLHQQWQJAR-UHFFFAOYSA-N [Cl+].[Cu+] Chemical compound [Cl+].[Cu+] YBVPWLHQQWQJAR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920006184 cellulose methylcellulose Polymers 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- PBGGNZZGJIKBMJ-UHFFFAOYSA-N di(propan-2-yl)azanide Chemical compound CC(C)[N-]C(C)C PBGGNZZGJIKBMJ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- MDBAAYRCFODAFZ-UHFFFAOYSA-N n'-phenylmethanediimine Chemical compound N=C=NC1=CC=CC=C1 MDBAAYRCFODAFZ-UHFFFAOYSA-N 0.000 description 1
- CMESPBFFDMPSIY-UHFFFAOYSA-N n,n'-diphenylmethanediimine Chemical compound C1=CC=CC=C1N=C=NC1=CC=CC=C1 CMESPBFFDMPSIY-UHFFFAOYSA-N 0.000 description 1
- XZPRZECOHCTTRV-UHFFFAOYSA-N n-cyclohexyl-n'-phenylmethanediimine Chemical compound C1CCCCC1N=C=NC1=CC=CC=C1 XZPRZECOHCTTRV-UHFFFAOYSA-N 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/395—Isocyanates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B15/00—Preparation of other cellulose derivatives or modified cellulose, e.g. complexes
- C08B15/05—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur
- C08B15/06—Derivatives containing elements other than carbon, hydrogen, oxygen, halogens or sulfur containing nitrogen, e.g. carbamates
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
- D01F2/06—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from viscose
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
- D01F2/24—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from cellulose derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Textile Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Artificial Filaments (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Coloring (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE541048D BE541048A (enrdf_load_stackoverflow) | 1954-09-09 | ||
| DEF17948A DE1011869B (de) | 1954-09-09 | 1954-09-09 | Verfahren zur Veredelung von Cellulose oder Cellulosederivaten |
| GB2345755A GB772343A (en) | 1954-09-09 | 1955-08-15 | Process for modifying cellulose or cellulose derivatives |
| FR1130846D FR1130846A (fr) | 1954-09-09 | 1955-09-07 | Procédé d'ennoblissement de la cellulose ou des dérivés de la cellulose |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF17948A DE1011869B (de) | 1954-09-09 | 1954-09-09 | Verfahren zur Veredelung von Cellulose oder Cellulosederivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1011869B true DE1011869B (de) | 1957-07-11 |
Family
ID=7088760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF17948A Pending DE1011869B (de) | 1954-09-09 | 1954-09-09 | Verfahren zur Veredelung von Cellulose oder Cellulosederivaten |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE541048A (enrdf_load_stackoverflow) |
| DE (1) | DE1011869B (enrdf_load_stackoverflow) |
| FR (1) | FR1130846A (enrdf_load_stackoverflow) |
| GB (1) | GB772343A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2187988A1 (enrdf_load_stackoverflow) * | 1972-06-07 | 1974-01-18 | Stanford Research Inst | |
| WO2001087984A1 (de) * | 2000-05-13 | 2001-11-22 | Clariant Gmbh | Modifizierte celluloseether, erhältlich durch umsetzung von celluloseethern mit freien hydroxygruppen mit di- und/oder polycarbonsäuren unter zusatz von katalysatoren sowie verfahren zu deren herstellung |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI793150A7 (fi) * | 1978-10-12 | 1981-01-01 | Battelle Memorial Institute | Menetelmä karboksimetyliselluloosan ja saatujen tuotteiden ristikytkemiseksi. |
| WO2003060227A2 (en) * | 2002-01-10 | 2003-07-24 | Glycozyme, Inc | Enzymatic degradation of cotton fibres: effect of protein cross-linking and the use of degradation to characterize fibers of plants of different genetic backgrounds |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB511536A (en) * | 1937-02-19 | 1939-08-21 | Deutshce Hydrierwerke Ag | Improvements in or relating to the treatment of textile fibres |
| US2415043A (en) * | 1944-03-23 | 1947-01-28 | Montclair Res Corp | Carbodimide-cellulose products and the process of making same |
-
0
- BE BE541048D patent/BE541048A/xx unknown
-
1954
- 1954-09-09 DE DEF17948A patent/DE1011869B/de active Pending
-
1955
- 1955-08-15 GB GB2345755A patent/GB772343A/en not_active Expired
- 1955-09-07 FR FR1130846D patent/FR1130846A/fr not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB511536A (en) * | 1937-02-19 | 1939-08-21 | Deutshce Hydrierwerke Ag | Improvements in or relating to the treatment of textile fibres |
| US2415043A (en) * | 1944-03-23 | 1947-01-28 | Montclair Res Corp | Carbodimide-cellulose products and the process of making same |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2187988A1 (enrdf_load_stackoverflow) * | 1972-06-07 | 1974-01-18 | Stanford Research Inst | |
| WO2001087984A1 (de) * | 2000-05-13 | 2001-11-22 | Clariant Gmbh | Modifizierte celluloseether, erhältlich durch umsetzung von celluloseethern mit freien hydroxygruppen mit di- und/oder polycarbonsäuren unter zusatz von katalysatoren sowie verfahren zu deren herstellung |
Also Published As
| Publication number | Publication date |
|---|---|
| GB772343A (en) | 1957-04-10 |
| BE541048A (enrdf_load_stackoverflow) | |
| FR1130846A (fr) | 1957-02-12 |
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