GB570433A - Improvements in or relating to the manufacture of softened non-fibrous cellulosic pellicles - Google Patents

Improvements in or relating to the manufacture of softened non-fibrous cellulosic pellicles

Info

Publication number
GB570433A
GB570433A GB11628/43A GB1162843A GB570433A GB 570433 A GB570433 A GB 570433A GB 11628/43 A GB11628/43 A GB 11628/43A GB 1162843 A GB1162843 A GB 1162843A GB 570433 A GB570433 A GB 570433A
Authority
GB
United Kingdom
Prior art keywords
dioxide
sulphoxide
dihydrothiophene
ethyl
sulphone
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
Application number
GB11628/43A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
British Cellophane Ltd
Original Assignee
British Cellophane Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by British Cellophane Ltd filed Critical British Cellophane Ltd
Publication of GB570433A publication Critical patent/GB570433A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/36Sulfur-, selenium-, or tellurium-containing compounds
    • C08K5/41Compounds containing sulfur bound to oxygen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

Pellicles such as films, sheets, bands, straws, caps and tubes of regenerated cellulose or lowly etherified cellulose ethers are softened by impregnating them with a water-soluble organic sulphoxidate of the formula X = S = On, in which n is either 1 or 2, and X represents one or two organic radicals in which there is a carbon atom directly attached to the sulphur atom. The softening agent may be a sulphoxide or a sulphone. It is regarded as water-soluble if it dissolves to the extent of at least 2 per cent by weight in water at a temperature not higher than 60 DEG C. Preferably, each organic radical, attached to the sulphoxy group, is a hydrocarbon residue containing at least one water-solubilising substituent or linkage, e.g. the groups -OH, -O-alkyl, -NH2, -COOH, -SO3H, -NH-, -CO- and -CO-NH-. The sulphoxide or sulphone may be a straight or branched chain compound, or a heterocyclic compound with the sulphur atom forming part of the ring. The sulphoxide or sulphone may be used in conjunction with other softening agents for regenerated cellulose materials, e.g. glycerine, ethylene glycol, formamide, glycol polyformal, N-(2 : 3-dihydroxypropyl)-hydroxyacetamide. A mixture of sulphoxides or sulphones may be used, e.g. 2 : 5-dihydrothiophene-1 : 1-dioxide and diethyl sulphone, or 3-methoxytetrahydrothiophene-1 : 1-dioxide and methyl butyl sulphoxide. Preferably, the regenerated cellulose materials are impregnated with an aqueous solution of the softening agent while they are still in the gel state following coagulation and regeneration, but already dried materials may be re-wetted and then impregnated with the solution of the softening agent. Impregnation may be effected by immersion or by spraying. Dyestuffs may be incorporated in the softening bath. In an example, viscose is extruded to form a continuous film which passes through coagulating and regenerating solutions, purifying and washing baths, and then through an aqueous solution of glycerine and the methanol adduct of 2 : 5-dihydrothiophene-1 : 1-dioxide, and then over drying rolls. The softened film may be used for wrapping cotton goods such as bed sheets and p pillow-cases. Instead of the methanol adduct, there may be used the ethanol, isopropanol, ethylene glycol, or glycerine adduct of 2 : 5-dihydrothiophene-1 : 1-dioxide. In other examples, a regenerated cellulose film is impregnated with an aqueous solution of beta-ethylsulphinyl tetra-methylene cyclic sulphone, 3 : 4-dimethoxy - tetrahydrothiophene - 1 : 1 - dioxide, diethyl sulphone, 2 : 5-dihydrothiophene-1 : 1-dioxide, or the addition product of water with 2 : 5-dihydrothiophene-1 : 1-dioxide. In another example, a regenerated cellulose tube is made by joining several viscose streams to form an annular stream which is then passed into a coagulating liquid. The purified tube is impregnated with a solution of the methanol adduct of 2 : 5-dihydrothiophene-1 : 1-dioxide. The tube is cut into short lengths which are used as secondary closures or seals for bottles. In other examples, regenerated cellulose film is impregnated with di - b - hydroxy - ethyl sul - phoxide, 2 : 21 - (methylene disulphinyl-) di - ethanol, ethyl - a - hydroxypropyl sulphoxide, ethyl-2 : 3-dihydroxy-propyl sulphoxide, methyl butyl sulphoxide, or di-ethyl sulphoxide. The methanol adduct of 2 : 5-dihydrothiophene-1 : 1-dioxide is made by causing methanol to react upon 3,4-dehydrocyclotetramethylene sulphone, preferably in an alkaline medium. The ethanol, isopropanol, ethylene glycol and glycerine adducts are made similarly. Beta-ethyl-sulphinyl tetramethylene cyclic sulphone is made by causing ethanethiol to react with 2 : 5-dihydro-thiophene-1 : 1-dioxide, preferably in alkaline medium, followed by oxidation of the resultant product with a solution of hydrogen peroxide. The compound 3 : 4-dimethoxytetrahydrothiophene-1 : 1-dioxide is made by reacting 2 : 5 - dihydrothiophene - 1 : 1 - dioxide with a chlorinating agent consisting of chlorine and absolute methanol at 0 DEG C. and subjecting the intermediate compound, 3 - chloro - 4 - methoxy - tetrahydrothiophene-1 : 1 - dioxide to the action of methyl alcoholic potassium hydroxide. Diethyl sulphone is obtained by refluxing diethyl sulphide with an excess of hydrogen peroxide solution. The compound 2 : 5-dihydrothiophene-1 : 1-dioxide is obtained by reacting sulphur dioxide with butadiene hydrocarbons in the presence of an antipolymerization catalyst, e.g. pyrogallol or other polyhydric phenol. Liquid sulphur dioxide may be used and the hydrocarbons may be dissolved in benzene. Di - b - hydroxy - ethyl sulphoxide is prepared by oxidising di-(b -hydroxy-ethyl) sulphide with hydrogen peroxide at 70 DEG C. The compound 2 : 21-(methylene disulphinyl-)di-ethanol is made by reacting 2 mols. of thioethylene glycol with 1 mol. of formaldehyde in presence of an acidic catalyst, and oxidising the product by means of hydrogen peroxide. Ethyl-a -hydroxypropyl sulphoxide is made by reacting ethanethiol with allyl alcohol in presence of mercuric acetate and oxidising the product with hydrogen peroxide. Ethyl-2 : 3-dihydroxypropyl sulphoxide is prepared by reacting ethanethiol with glycerine chlorhydrin in presence of alkali and oxidising the product with peroxide. Methyl butyl sulphoxide is obtained by the action of methyl chloride on butanethiol under alkaline conditions, and oxidising the product with peroxide. Specifications 211,446, [Class 2 (ii)], and 552,498 are referred to. The Specification as open to inspection under Sect. 91 comprises also the treatment of artificial filaments and sponge-material. This subject-matter does not appear in the Specification as accepted.
GB11628/43A 1942-08-22 1943-07-16 Improvements in or relating to the manufacture of softened non-fibrous cellulosic pellicles Expired GB570433A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US570433XA 1942-08-22 1942-08-22

Publications (1)

Publication Number Publication Date
GB570433A true GB570433A (en) 1945-07-06

Family

ID=22008156

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11628/43A Expired GB570433A (en) 1942-08-22 1943-07-16 Improvements in or relating to the manufacture of softened non-fibrous cellulosic pellicles

Country Status (1)

Country Link
GB (1) GB570433A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2273458A (en) * 1992-12-18 1994-06-22 China Int Ass Science & Tech Vegetable cellulose films

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2273458A (en) * 1992-12-18 1994-06-22 China Int Ass Science & Tech Vegetable cellulose films
GB2273458B (en) * 1992-12-18 1997-06-04 China Int Ass Science & Tech Vegetable cellulose films

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