US3106439A - Process of dry creaseproofing cellulosic fabrics with divinyl shlphone - Google Patents

Process of dry creaseproofing cellulosic fabrics with divinyl shlphone Download PDF

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Publication number
US3106439A
US3106439A US2107A US210760A US3106439A US 3106439 A US3106439 A US 3106439A US 2107 A US2107 A US 2107A US 210760 A US210760 A US 210760A US 3106439 A US3106439 A US 3106439A
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United States
Prior art keywords
dry
fabric
divinyl
cellulose
divinyl sulphone
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Expired - Lifetime
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US2107A
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English (en)
Inventor
Valentine Leslie Mackenzie
Sagar Brian Frederick
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Tootal Broadhurst Lee Co Ltd
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Tootal Broadhurst Lee Co Ltd
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244Treating 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
    • D06M13/248Treating 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
    • D06M13/272Unsaturated compounds containing sulfur atoms
    • D06M13/278Vinylsulfonium compounds; Vinylsulfone or vinylsulfoxide compounds
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/02Vinyl sulfones and precursors thereof

Definitions

  • the primary object of this suggested process was to reduce the shrinkage of cotton and regenerated cellulose textile materials and fabrics which are subject to washing, but as a result of the treatment cotton was found to retain creases and mechanical effects, such as pleating, made before treatment and subsequently to retain these creases when washed, and treated fabrics have also been found to resist creasing when in the wet state. Furthermore, treated cotton has been found not to retain chlorine, so that it was not damaged or made yellow by washing in presence of chlorine-containing bleaching agents. Also the effects of the treatment were not removed by severe laundering.
  • Cotton and regenerated cellulose fabrics treated by this suggested process have little or no ability to resist creasing when dry (dry crease-resistance or dry C.R.) which we prefer to measure by means of the dry recovery machine referred to on page 388 of An Introduction to Textile Finishing? by J. T. Marsh, published by Chapman & Hall in 1948.
  • dry C.R. dry recovery machine
  • the ability to dry smooth after laundering and the resistance to creasing when wet can be good as shown by the smooth drying index (S.D.I.) which we prefer to measure by use of an apparatus consisting of (l a crease maker, (2) a drying cabinet, and (3) a crease gauge.
  • a lack of dry cr e-resistance can be a severe disadvantage and we have now discovered a process by which an improved balance between dry crease-resistance and 3,106,439 Patented Oct. 8, 1963 smooth drying index can be obtained using an alkali catalysed divinyl sulphone system.
  • a process for the chemical modification of cellulosic material comprises treating cellulose or a cellulose derivative containing cellulose hydroxyl groups with divinyl sulphone and an alkaline or potential alkaline catalyst which is unreactive to divinyl sulphone and drying the treated material by heating without previous removal of the catalyst.
  • Fabrics, especially cotton and rayon fabrics, treated by the process of the present invention have improved dry crease-resistance as compared with the material before treatment. Improvement in the dry crease-resistance of the material is obtained if the material, after being treated with the divinyl sulphone in the presence of a suitable alkaline catalyst is dried by heating under mild conditions that is at a temperature below 100 C. and preferably below C. The dry crease-resistance can be enhanced if the dried sample is then baked. We prefer therefore in order to obtain the best and most uniform results to dry the impregnated and mangled cloth on a stenter at as low a temperature as possible and then bake it at l00l70 C. for l-S minutes. The dry crease-resistance increases as the temperature of baking is increased.
  • Cellulosic materials treated according to this invention also have the property of retaining even when washed creases and mechanical effects such as pleated, glazed and embossed effects made before or during treatment. It is also possible by the process of this invention to improve the fixation of starch and starch products.
  • an alkaline catalyst in order to bring about the reaction between the divinyl sulphone and the cellulosic material.
  • Any catalyst giving a bath pH greater than, or equal to, 8.5 and which does not react with divinyl sulphone can be used such as, for example, sodium hydroxide, sodium carbonate or sodium metasilicate. If the bath pH is greater than 12.0, however, we find that the bath 'life is too short for convenient operation of a one-bath process, and we find that a two-bath process is necessary.
  • divinyl sulphone in the presence of aqueous alkali is converted, at a rate proportional to the concentration and basic strength of the alkali, into products that do not react with cellulose.
  • the catalyst must be such as to give a bath pH within the range 85-120 and preferably a catalyst concentration not greater than 0.2 molar.
  • a further advantage of operating within this range of pH is that reaction between the divinyl sulphone and the cellulose in the swollen state is less than it is at higher pH values.
  • sodium bicarbonate which gives a low bath pH but is converted into a stronger alkali, sodium carbonate, when heated.
  • sodium bicarbonate therefore, one obtains a long bath life'and yet it breaks down to form an alkali which gives a high degree of fixation on curing.
  • the use of this catalyst minimises the reaction of divinyl sulphone with the cellulose whilst the latter is in the wet or swollen state.
  • the cellulosic material which may be treated according to this invention may include cotton, rayonor linen fabrics or fabrics of cellulose derivatives containing cellulosic hydroxyl groups such as secondary cellulose acetate. In the case of fabrics these can be either woven or non-woven fabrics. Mixtures of cellulosic with nonoellulosic fibres, for example wool or nylon, may be treated but we prefer to treat mixtures containing at least 50% of cellulosic fibres.
  • Example 1 A sample of cotton fabric was impregnated with 100 mls. of a solution containing mls. of divinyl sulphone and 5 mls. of a 2 molar solution of sodium metasilicate. The sample was squeezed by passing it between the bowls of a mangle adjusted so that the sample retained about 80% by weight of liquor and dried at 55 C. for 25 minutes. It was then immediately baked at 120 C. for 2 minutes. After washing in a boiling solution containing 0.25% soap and 0.25% soda ash for 5 minutes it had the following properties:
  • Example 2 A sample of cotton poplin shirting was impregnated with a 5% v./v. solution of divinyl sulphone that was tenth normal with respect to sodium hydroxide. After mangling and drying the sample was baked for 2 minutes at 160 C. It was given a similar wash-off to the sample in Example 1 and had the following properties:
  • Example 3 Two similar samples of cotton fabric were impregnated with a solution, 1000 mls. of which contained 0.4 gm. mole of divinyl sulphone and 0.1 gm. mole of sodium carbonate. The samples were mangled so that they retained about of the liquor and then placed in a convector drying cabinet with an air temperature of 55 C. for 25 minutes. The samples were then dry to the touch. One of the samples was then baked for 2 minutes at 130 C. after which they were washed off together in a boiling solution containing 0.25% soap and 0.25% soda ash for 5 minutes. They then had the following properties:
  • Example 4 A pair of samples of the same material as in Example 3 was treated in an exactly analogous manner using an impregnating solution that was 0.4 molar with respect to divinyl sulphone and 0.5 molar in sodium hydroxide. This bath had to be used within a minute or two of adding the alkali; precipitation occurred after 9 minutes.
  • the samples had the following properties:
  • Example 5 A sample of rayon material was impregnated with an aqueous solution mls. of which contained 5.5 mls. of divinyl sulphone and 0.4 g. of sodium hydroxide. The sample was mangled to about liquor retention and dried before being baked at 110 for 2 minutes. After being washed in a boiling solution containing 0.25% soap and 0.25% soda ash for 5 minutes, the sample had the following properties:
  • Example 6 Dried Dried and baked only, ()4 min. percent at C-.),
  • Example 7 Here the treatment was as in Example 6 but the bicarbonate was increased to 0.25 molar and one of the samples was baked for 8 minutes at 100 C. The following results were produced:
  • Process for the chemical modification of fabric containing at least 50 percent of fibres selected from the group consisting of fibres of cellulose and fibres of cellulose derivatives having free hydroxyl groups comprising applying to the fabric aqueous solutions of divinyl sulphone and a member which is unreactive to divinyl sulphone and which is selected from the group consisting of alkaline catalysts and catalysts which are alkaline when heated so as to effect the application of said solution at a pH of at least 8.5, and drying the fabric by heating at a temperature below approximately 100 C. without pre vious removal of the selected catalyst until improved dry crease-resistance of said fabric is obtained.
  • alkaline catalysts are selected from the group consisting of sodium hydroxide, sodium carbonate and sodium metasilicate.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US2107A 1959-01-17 1960-01-13 Process of dry creaseproofing cellulosic fabrics with divinyl shlphone Expired - Lifetime US3106439A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1802/59A GB915571A (en) 1959-01-17 1959-01-17 Improvements in the treatment of cellulosic fabrics

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US3106439A true US3106439A (en) 1963-10-08

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US (1) US3106439A (US07345094-20080318-C00003.png)
BE (1) BE586604A (US07345094-20080318-C00003.png)
CH (1) CH377308A (US07345094-20080318-C00003.png)
DE (1) DE1179536B (US07345094-20080318-C00003.png)
FR (1) FR1245882A (US07345094-20080318-C00003.png)
GB (1) GB915571A (US07345094-20080318-C00003.png)
NL (1) NL247423A (US07345094-20080318-C00003.png)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3281204A (en) * 1962-06-21 1966-10-25 Clark M Welch Polymeric adducts of divinyl sulfone with water as crosslinking agents for cellulose
US3359061A (en) * 1961-12-19 1967-12-19 Clark M Welch Process for making alkoxyethylsulfonylethyl ethers of cellulose
US3414367A (en) * 1963-11-06 1968-12-03 Agriculture Usa Process for making n-substituted aminoethylsulfonylethyl ethers of cellulose
US3501260A (en) * 1964-03-18 1970-03-17 Stevens & Co Inc J P Polyvinyl alcohol and starch bound to cellulosic textile substrate through reaction with beta-oxyethyl sulfones
US3512916A (en) * 1961-10-06 1970-05-19 Gaf Corp Two step reaction of textile fibers with 2-vinylsulfonylethanol
US3619277A (en) * 1969-11-26 1971-11-09 Christina L Allen Method of improving the crease resistance of a cellulosic fabric
US6521223B1 (en) 2000-02-14 2003-02-18 Genzyme Corporation Single phase gels for the prevention of adhesions

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3024500A1 (de) * 1980-06-28 1982-01-28 Gewerkschaft Eisenhütte Westfalia, 4670 Lünen Strebrandausbau

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2343920A (en) * 1940-08-30 1944-03-14 Du Pont Textile treatment process
US2482756A (en) * 1944-06-10 1949-09-27 Bancroft & Sons Co J Flameproofing of fibrous materials
US2524399A (en) * 1948-07-07 1950-10-03 Us Rubber Co Cellulose treated with di-vinyl sulfone to shrinkproof
US2774691A (en) * 1954-09-21 1956-12-18 Shell Dev Treatment of textile materials and product
US2785949A (en) * 1954-01-08 1957-03-19 Quaker Chemical Products Corp Process for the dimensional control of cellulose textile materials by applying polymeric acetals and products resulting therefrom

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2343920A (en) * 1940-08-30 1944-03-14 Du Pont Textile treatment process
US2482756A (en) * 1944-06-10 1949-09-27 Bancroft & Sons Co J Flameproofing of fibrous materials
US2524399A (en) * 1948-07-07 1950-10-03 Us Rubber Co Cellulose treated with di-vinyl sulfone to shrinkproof
US2785949A (en) * 1954-01-08 1957-03-19 Quaker Chemical Products Corp Process for the dimensional control of cellulose textile materials by applying polymeric acetals and products resulting therefrom
US2774691A (en) * 1954-09-21 1956-12-18 Shell Dev Treatment of textile materials and product

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3512916A (en) * 1961-10-06 1970-05-19 Gaf Corp Two step reaction of textile fibers with 2-vinylsulfonylethanol
US3359061A (en) * 1961-12-19 1967-12-19 Clark M Welch Process for making alkoxyethylsulfonylethyl ethers of cellulose
US3281204A (en) * 1962-06-21 1966-10-25 Clark M Welch Polymeric adducts of divinyl sulfone with water as crosslinking agents for cellulose
US3414367A (en) * 1963-11-06 1968-12-03 Agriculture Usa Process for making n-substituted aminoethylsulfonylethyl ethers of cellulose
US3501260A (en) * 1964-03-18 1970-03-17 Stevens & Co Inc J P Polyvinyl alcohol and starch bound to cellulosic textile substrate through reaction with beta-oxyethyl sulfones
US3619277A (en) * 1969-11-26 1971-11-09 Christina L Allen Method of improving the crease resistance of a cellulosic fabric
US6521223B1 (en) 2000-02-14 2003-02-18 Genzyme Corporation Single phase gels for the prevention of adhesions

Also Published As

Publication number Publication date
DE1179536B (de) 1964-10-15
CH377308A (de) 1964-06-30
GB915571A (en) 1963-01-16
CH40660A4 (US07345094-20080318-C00003.png) 1964-01-31
NL247423A (US07345094-20080318-C00003.png)
FR1245882A (fr) 1960-11-10
BE586604A (US07345094-20080318-C00003.png)

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