GB664795A - Process for the chemical modification of cellulosic materials - Google Patents
Process for the chemical modification of cellulosic materialsInfo
- Publication number
- GB664795A GB664795A GB13527/49A GB1352749A GB664795A GB 664795 A GB664795 A GB 664795A GB 13527/49 A GB13527/49 A GB 13527/49A GB 1352749 A GB1352749 A GB 1352749A GB 664795 A GB664795 A GB 664795A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cellulose
- sulphone
- fabrics
- treated
- catalyst
- 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
Links
- 239000000463 material Substances 0.000 title abstract 6
- 238000007385 chemical modification Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 22
- 229920002678 cellulose Polymers 0.000 abstract 13
- 239000001913 cellulose Substances 0.000 abstract 13
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 abstract 13
- 239000004744 fabric Substances 0.000 abstract 13
- 239000000243 solution Substances 0.000 abstract 13
- 239000003054 catalyst Substances 0.000 abstract 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 6
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 6
- PMZURENOXWZQFD-UHFFFAOYSA-L sodium sulphate Substances [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract 6
- 229920000297 Rayon Polymers 0.000 abstract 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 4
- 229920000742 Cotton Polymers 0.000 abstract 4
- 229910019142 PO4 Inorganic materials 0.000 abstract 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 4
- 239000003513 alkali Substances 0.000 abstract 4
- 239000000908 ammonium hydroxide Substances 0.000 abstract 4
- 239000007864 aqueous solution Substances 0.000 abstract 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 4
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract 4
- 235000011152 sodium sulphate Nutrition 0.000 abstract 4
- 125000001174 sulfone group Chemical group 0.000 abstract 4
- 239000004627 regenerated cellulose Substances 0.000 abstract 3
- 238000004513 sizing Methods 0.000 abstract 3
- 235000002639 sodium chloride Nutrition 0.000 abstract 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 2
- 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 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract 2
- 150000007514 bases Chemical class 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 239000010452 phosphate Substances 0.000 abstract 2
- 235000021317 phosphate Nutrition 0.000 abstract 2
- 239000002964 rayon Substances 0.000 abstract 2
- 230000035484 reaction time Effects 0.000 abstract 2
- 239000001632 sodium acetate Substances 0.000 abstract 2
- 235000017281 sodium acetate Nutrition 0.000 abstract 2
- 239000011780 sodium chloride Substances 0.000 abstract 2
- 239000001488 sodium phosphate Substances 0.000 abstract 2
- 229910052938 sodium sulfate Inorganic materials 0.000 abstract 2
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- 239000000080 wetting agent Substances 0.000 abstract 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 abstract 1
- 239000004375 Dextrin Substances 0.000 abstract 1
- 229920001353 Dextrin Polymers 0.000 abstract 1
- 229920000084 Gum arabic Polymers 0.000 abstract 1
- 239000004372 Polyvinyl alcohol Substances 0.000 abstract 1
- 241000978776 Senegalia senegal Species 0.000 abstract 1
- 229920002472 Starch Polymers 0.000 abstract 1
- 229920001938 Vegetable gum Polymers 0.000 abstract 1
- 239000000205 acacia gum Substances 0.000 abstract 1
- 235000010489 acacia gum Nutrition 0.000 abstract 1
- 239000012670 alkaline solution Substances 0.000 abstract 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 abstract 1
- 239000001768 carboxy methyl cellulose Substances 0.000 abstract 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 abstract 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 abstract 1
- 229940105329 carboxymethylcellulose Drugs 0.000 abstract 1
- 229920002301 cellulose acetate Polymers 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 235000019425 dextrin Nutrition 0.000 abstract 1
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 abstract 1
- -1 linen Polymers 0.000 abstract 1
- 229920000609 methyl cellulose Polymers 0.000 abstract 1
- 239000001923 methylcellulose Substances 0.000 abstract 1
- 235000010981 methylcellulose Nutrition 0.000 abstract 1
- 229920002451 polyvinyl alcohol Polymers 0.000 abstract 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000008107 starch Substances 0.000 abstract 1
- 235000019698 starch Nutrition 0.000 abstract 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical group [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 abstract 1
- 239000002023 wood Substances 0.000 abstract 1
- 239000012991 xanthate Substances 0.000 abstract 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
- D06M13/244—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 sulfur or phosphorus
- D06M13/248—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 sulfur or phosphorus with compounds containing sulfur
- D06M13/272—Unsaturated compounds containing sulfur atoms
- D06M13/278—Vinylsulfonium compounds; Vinylsulfone or vinylsulfoxide compounds
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
Abstract
Cellulose derivatives are obtained by causing cellulose or a cellulose derivative containing free cellulose hydroxyl groups to react with vinyl sulphone, (CH2=CH)2SO2, in presence of a catalyst consisting of an unreactive basic compound. The cellulose or cellulose derivative may be in the form of fibres, yarns, or fabrics. It may be cotton, linen, wood, viscose rayon, cuprammonium rayon, saponified cellulose acetate, or a salt of cellulose xanthate. Fabric or yarn may be moistened with an aqueous solution of vinyl sulphone with or without a wetting agent and then treated with an aqueous solution of the alkaline catalyst. The treatment may be carried out at 0-100 DEG C., the reaction time being 2 hours to a few seconds. The fabric or yarn may then be washed until free from catalyst and unreacted sulphone, and may then be dried. The treated cellulose or regenerated cellulose is insoluble in cuprammonium or quaternary ammonium hydroxide solutions, e.g. tetraethyl or benzyl trimethyl ammonium hydroxide. The treated fibres swell less than untreated fibres when immersed in water or alkali solutions. If desired, the reaction can be carried out under anhydrous conditions or in the presence of organic solvents such as dioxane, benzene, or chloroform. The fabric may be treated first with the alkali and then with the vinyl sulphone, or the alkali and sulphone may be applied together. The catalyst may be sodium or potassium hydroxide, carbonate, or phosphate; an alkaline-earth metal hydroxide; or a quaternary ammonium hydroxide. The vinyl sulphone may be used in solution in a concentrated solution of sodium chloride, sulphate, acetate, or phosphate. With cotton fabrics caustic soda solutions of 0.1-30 per cent strength may be used, but for regenerated cellulose fabrics the caustic soda is preferably not greater than 8 per cent. The caustic soda solutions may contain sodium sulphate. The vinyl sulphone applied may be from 0.1 per cent to 100 per cent by weight of the cellulose.ALSO:Fibres, yarns, or fabrics of cellulose or cellulose derivatives containing free hydroxyl groups are subjected to the action of vinyl sulphone (CH2=CH)2SO2, in presence of a basic compound which acts as a catalyst. Cotton, linen, viscose rayon, cuprammonium rayon, or saponified cellulose acetate rayon, may be treated. Yarns and fabrics are rendered resistant to shrinking, creasing, and loss of mechanically-imparted shape or form. The treatment sets the twist in yarns and the pleats in pleated fabrics. Fabric or yarn may be moistened with an aqueous solution of vinyl sulphone, with or without a wetting agent, and then treated with an aqueous solution of the alkaline catalyst. The treatment may be carried out at 0-100 DEG C., the reaction time being 2 hours to a few seconds. The material is subsequently washed until free from catalyst and unreacted sulphone, and is then dried. The treated material is insoluble in cuprammonium or quaternary ammonium hydroxide solutions. Treated fibres swell less than untreated fibres when immersed in water or alkali solutions. The reaction may be carried out under anhydrous conditions or in the presence of organic solvents such as dioxane, benzene, or chloroform. The catalyst may be sodium or potassium hydroxide, carbonate, or phosphate, or an alkaline-earth metal hydroxide, or a quaternary ammonium hydroxide. The vinyl sulphone may be used in solution in sodium chloride, sulphate, acetate, or phosphate solution. With cotton fabrics, caustic soda solutions of 0.1-30 per cent may be used, but for regenerated cellulose fabrics the caustic soda is preferably not greater than 8 per cent. The caustic soda solutions may contain sodium sulphate. The vinyl sulphone applied may be 0.1-100 per cent by weight of the cellulose. Sizing material may be incorporated with the vinyl sulphone solution or the alkaline solution, or the fabrics may be sized before treating with the vinyl sulphone. The sizing material may be starch, dextrin, methyl cellulose, carboxy methyl cellulose, polyvinyl alcohol, gum arabic, or other vegetable gum. Part of the sulphone reacts with the cellulose and part with the sizing material so that a water-insoluble, cross-linked compound is formed.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US664795XA | 1948-07-07 | 1948-07-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB664795A true GB664795A (en) | 1952-01-09 |
Family
ID=22069749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB13527/49A Expired GB664795A (en) | 1948-07-07 | 1949-05-20 | Process for the chemical modification of cellulosic materials |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB664795A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2270314A (en) * | 1992-08-20 | 1994-03-09 | Leipziger Arzneimittelwerk Gmb | Preparation of cellulose ethers |
-
1949
- 1949-05-20 GB GB13527/49A patent/GB664795A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2270314A (en) * | 1992-08-20 | 1994-03-09 | Leipziger Arzneimittelwerk Gmb | Preparation of cellulose ethers |
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