US3305377A - Manufacture of regenerated cellulose fibres - Google Patents
Manufacture of regenerated cellulose fibres Download PDFInfo
- Publication number
- US3305377A US3305377A US312852A US31285263A US3305377A US 3305377 A US3305377 A US 3305377A US 312852 A US312852 A US 312852A US 31285263 A US31285263 A US 31285263A US 3305377 A US3305377 A US 3305377A
- Authority
- US
- United States
- Prior art keywords
- cellulose
- percent
- aminoethyl
- fibres
- viscose
- 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
- 239000004627 regenerated cellulose Substances 0.000 title claims description 18
- 229920003043 Cellulose fiber Polymers 0.000 title description 13
- 238000004519 manufacturing process Methods 0.000 title description 4
- 229920002678 cellulose Polymers 0.000 claims description 46
- 239000001913 cellulose Substances 0.000 claims description 46
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- 229920000297 Rayon Polymers 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 11
- 239000000835 fiber Substances 0.000 claims description 11
- MELCWEWUZODSIS-UHFFFAOYSA-N 2-[2-(diethylamino)ethoxy]-n,n-diethylethanamine Chemical compound CCN(CC)CCOCCN(CC)CC MELCWEWUZODSIS-UHFFFAOYSA-N 0.000 claims description 7
- GXVUZYLYWKWJIM-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanamine Chemical compound NCCOCCN GXVUZYLYWKWJIM-UHFFFAOYSA-N 0.000 claims description 5
- -1 AMINOETHYL Chemical class 0.000 claims description 5
- RZFBEFUNINJXRQ-UHFFFAOYSA-M sodium ethyl xanthate Chemical compound [Na+].CCOC([S-])=S RZFBEFUNINJXRQ-UHFFFAOYSA-M 0.000 claims description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 12
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 8
- 238000004043 dyeing Methods 0.000 description 8
- JVIPLYCGEZUBIO-UHFFFAOYSA-N 2-(4-fluorophenyl)-1,3-dioxoisoindole-5-carboxylic acid Chemical compound O=C1C2=CC(C(=O)O)=CC=C2C(=O)N1C1=CC=C(F)C=C1 JVIPLYCGEZUBIO-UHFFFAOYSA-N 0.000 description 6
- 229920001425 Diethylaminoethyl cellulose Polymers 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000975 dye Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000000980 acid dye Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 238000009987 spinning Methods 0.000 description 4
- 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 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical class NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000012991 xanthate Substances 0.000 description 2
- 240000008213 Brosimum alicastrum Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- WSYUEVRAMDSJKL-UHFFFAOYSA-N ethanolamine-o-sulfate Chemical compound NCCOS(O)(=O)=O WSYUEVRAMDSJKL-UHFFFAOYSA-N 0.000 description 1
- 238000005213 imbibition Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000005828 ramon Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- D01F2/08—Composition of the spinning solution or the bath
- D01F2/10—Addition to the spinning solution or spinning bath of substances which exert their effect equally well in either
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
- C08L1/08—Cellulose derivatives
- C08L1/22—Cellulose xanthate
- C08L1/24—Viscose
Definitions
- This invention relates to themanufacture of regenerated cellulose fibres and is particularly concerned with improving the acid dyeing characteristics of such fibres made from viscose.
- the cellulose molecule contains no basic groups and, because of this, regenerated cellulose fibres are not dyeable with acid dyes.
- the acid dyes are a large class developed for wool-dyeing and comprise a Wide range of clear colours which are not as expensive as some of the direct dyes normally used in dyeing cellulose. It would be advantageous to modify cellulose so that regenerated cellulose fibre could be dyed substantially with acid dyes and, indeed, the viscose industry has long sought to do this.
- Some of the properties sought after in a dyeing process and in the dyed fibre are, good levelling properties of the dye between the dye sites on the fibre, good wash fastness, good light fastness, a fast rate of exhaustion of the dyebath and a high extent of exhaustion of the dyebath.
- the dye sites in a modified cellulose should be chemically bonded to the cellulose molecule.
- the invention comprises a regenerated cellulose fibre containing the aminoethyl and diethylaminoethyl ethers of cellulose.
- a regenerated cellulose fibre containing aminoethyl cellulose as the sole amino compound and dyed with acid dye has good fastness to light, but, in general, the fibre does not give a good rate, or extent, of exhaustion of an acid dyebath.
- a regenerated cellulose fibre containing diethylaminoethyl cellulose as the sole amino compound results in the fibre giving a good rate and extent of exhaustion of an acid dyebath but the resulting dyed fibre generally tends to have a poorer fastness to light than one containing aminoethyl cellulose.
- a fibre having good exhaustion of the dyebath and good fastness to light can be obtained.
- aminoethyl ethers of cellulose may be incorporated, or formed in situ, in the cellulose at any suitable stage in the production of the fibre up to the finishing of the fibre.
- aminoethyl cellulose and diethylaminoethyl cellulose may be made beforehand and can then be either xanthated and introduced into ordinary viscose, or mixed with the cellulose or alkali cellulose before xanthation.
- reagents which react with cellulose to form the ether in situ may be added at suitable stages in production. Examples of such reagents are 2-aminoethyl sulphuric acid, 2-chloroethanolamine and the corresponding diethyl compounds.
- alkali cellulose is dispersed in an inert polar organic liquid, for example acetone, before the carbon disulphide is added, whereas in the second method no such dispersing liquid is used.
- an inert polar organic liquid for example acetone
- the regenerated cellulose fibre therefore, preferably contains up to 0.065 percent of nitrogen embodied in amino-ethyl groups.
- the total nitrogen content of the regenerated fibres derived solely from the amino ethers is preferably at least 0.165.
- the fastness to light of dyed regenerated cellulose yarns may be further improved by treating the yarns, before dyeing, with a cross-linking agent.
- the product had an imbibition of percent, high resilience, wholly handle, a pronounced wool dyeing affinity for acid-levelling, acid-aggregated and prematallised wool dyes and good light fastness properties when dyed with representative members of these classes of dyestutf.
- the high Wool dyeing afiinity was not significantly reduced by prolonged hot Wet treatment in acid media.
- Regenerated cellulose fibres containing, uniformly physically dispersed therein, an aminoethyl and a diethylaminoethyl ether of cellulose in proportions such as to give a total nitrogen content of between about 0.165 and about 0.215 percent by weight of the fibre.
- Regenerated cellulose fibres as claimed in claim 1 containing at least 0.165 percent by weight of nitrogen derived from the amino ethers.
- Regenerated cellulose fibres as claimed in claim 1 containing up to 0.065 percent by weight of nitrogen derived from the aminoethyl ether of cellulose component.
- Regenerated cellulose fibres as claimed in claim 1 containing between 0.10 and 0.15 percent by weight of nitrogen derived from the diethylaminoethyl component.
- a viscose process for making acid dyeable fibres of regenerated cellulose comprising incorporating a sodium xanthate solution of an aminoethyl ether of cellulose and of a diethylaminoethyl ether of cellulose in a viscose in proportions such as to give a total nitrogen content of between about 0.165 and about 0.215 percent by weight of cellulose.
- a viscose process for making acid dyeable fibres of regenerated cellulose comprising forming a mixture of aminoethyl and diethylaminoethyl ethers of cellulose with cellulose capable of being xanthated or alkali cellulose in proportions such as to give a total nitrogen content of between about 0.165 and about 0.215 percent by weigh of cellulose, and xanthating the mixture.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3811562 | 1962-10-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3305377A true US3305377A (en) | 1967-02-21 |
Family
ID=10401285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US312852A Expired - Lifetime US3305377A (en) | 1962-10-09 | 1963-10-01 | Manufacture of regenerated cellulose fibres |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3305377A (es) |
| AT (1) | AT245159B (es) |
| BE (1) | BE638428A (es) |
| CH (1) | CH437621A (es) |
| DE (1) | DE1469062A1 (es) |
| ES (1) | ES292332A1 (es) |
| GB (1) | GB1052621A (es) |
| NL (1) | NL298982A (es) |
| SE (1) | SE302818B (es) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4113674A (en) * | 1976-12-27 | 1978-09-12 | The Dow Chemical Company | Poly-2-alkyl-2-oxazoline modified regenerated cellulosics |
| US5529585A (en) * | 1994-06-30 | 1996-06-25 | Hoechst Ag | Rayon modified with polymeric amine compounds |
| US5542955A (en) * | 1994-10-04 | 1996-08-06 | Hoechst Aktiengesellschaft | Dyeing modified viscose fibers with acid or direct dyes |
| US5565007A (en) * | 1994-05-17 | 1996-10-15 | Hoechst Aktiengesellschaft | Amination of rayon |
| US5684141A (en) * | 1994-01-29 | 1997-11-04 | Hoechst Aktiengesellschaft | Aminated cellulosic synthetic fibers |
| US9723841B2 (en) | 2009-03-11 | 2017-08-08 | Akzo Nobel N.V. | Herbicidal formulations comprising glyphosate and alkoxylated glycerides |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4154676A (en) * | 1971-07-23 | 1979-05-15 | Viscose Development Co., Ltd. | Ion exchange process using activated regenerated cellulose |
| DE4417211A1 (de) * | 1994-05-17 | 1995-11-23 | Hoechst Ag | Aminierung von Regeneratcellulose |
| DE4422865A1 (de) | 1994-06-30 | 1996-01-04 | Hoechst Ag | Verfahren zur Herstellung von aminierten Fasern aus Regeneratcellulose |
| DE4433951A1 (de) | 1994-09-23 | 1996-03-28 | Hoechst Ag | Verfahren zur Herstellung von aminierter Regeneratcellulose |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2656241A (en) * | 1951-05-11 | 1953-10-20 | Jr George L Drake | Further aminized aminoalkylated celluloses by reacting with ethylenimine |
-
0
- BE BE638428D patent/BE638428A/xx unknown
- NL NL298982D patent/NL298982A/xx unknown
- GB GB1052621D patent/GB1052621A/en active Active
-
1963
- 1963-10-01 US US312852A patent/US3305377A/en not_active Expired - Lifetime
- 1963-10-09 SE SE11058/63A patent/SE302818B/xx unknown
- 1963-10-09 ES ES292332A patent/ES292332A1/es not_active Expired
- 1963-10-09 CH CH1242063A patent/CH437621A/de unknown
- 1963-10-09 AT AT808763A patent/AT245159B/de active
- 1963-10-09 DE DE19631469062 patent/DE1469062A1/de active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2656241A (en) * | 1951-05-11 | 1953-10-20 | Jr George L Drake | Further aminized aminoalkylated celluloses by reacting with ethylenimine |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4113674A (en) * | 1976-12-27 | 1978-09-12 | The Dow Chemical Company | Poly-2-alkyl-2-oxazoline modified regenerated cellulosics |
| US5684141A (en) * | 1994-01-29 | 1997-11-04 | Hoechst Aktiengesellschaft | Aminated cellulosic synthetic fibers |
| US5865858A (en) * | 1994-01-29 | 1999-02-02 | Hoechst Aktiengesellschaft | Aminated cellulosic synthetic fibers |
| US5565007A (en) * | 1994-05-17 | 1996-10-15 | Hoechst Aktiengesellschaft | Amination of rayon |
| US5529585A (en) * | 1994-06-30 | 1996-06-25 | Hoechst Ag | Rayon modified with polymeric amine compounds |
| US5542955A (en) * | 1994-10-04 | 1996-08-06 | Hoechst Aktiengesellschaft | Dyeing modified viscose fibers with acid or direct dyes |
| US9723841B2 (en) | 2009-03-11 | 2017-08-08 | Akzo Nobel N.V. | Herbicidal formulations comprising glyphosate and alkoxylated glycerides |
Also Published As
| Publication number | Publication date |
|---|---|
| BE638428A (es) | |
| DE1469062A1 (de) | 1969-03-13 |
| SE302818B (es) | 1968-08-05 |
| AT245159B (de) | 1966-02-10 |
| CH437621A (de) | 1967-06-15 |
| GB1052621A (es) | |
| NL298982A (es) | |
| ES292332A1 (es) | 1964-02-16 |
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