US3106439A - Process of dry creaseproofing cellulosic fabrics with divinyl shlphone - Google Patents
Process of dry creaseproofing cellulosic fabrics with divinyl shlphone Download PDFInfo
- 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
- Authority
- US
- United States
- Prior art keywords
- dry
- fabric
- divinyl
- cellulose
- divinyl 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 24
- 230000008569 process Effects 0.000 title claims description 24
- 239000004744 fabric Substances 0.000 title description 27
- 238000004855 creaseproofing Methods 0.000 title description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title 2
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims description 26
- 239000003054 catalyst Substances 0.000 claims description 22
- 229920002678 cellulose Polymers 0.000 claims description 16
- 239000001913 cellulose Substances 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 238000007385 chemical modification Methods 0.000 claims description 4
- 239000000835 fiber Substances 0.000 claims description 2
- -1 HYDROXYL GROUPS Chemical group 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000463 material Substances 0.000 description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- 229920000742 Cotton Polymers 0.000 description 9
- 239000003513 alkali Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- 235000017550 sodium carbonate Nutrition 0.000 description 8
- 230000004584 weight gain Effects 0.000 description 6
- 235000019786 weight gain Nutrition 0.000 description 6
- 238000005406 washing Methods 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000004115 Sodium Silicate Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 235000019795 sodium metasilicate Nutrition 0.000 description 3
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 3
- 229910052911 sodium silicate Inorganic materials 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000005815 base catalysis Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000004900 laundering Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000004745 nonwoven fabric Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- 239000004627 regenerated cellulose Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 239000002759 woven fabric Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 238000009988 textile finishing Methods 0.000 description 1
- 210000002268 wool Anatomy 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
- D06M13/244—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
-
- Y—GENERAL 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/02—Vinyl 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.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
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 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3106439A true US3106439A (en) | 1963-10-08 |
Family
ID=9728260
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US2107A Expired - Lifetime US3106439A (en) | 1959-01-17 | 1960-01-13 | Process of dry creaseproofing cellulosic fabrics with divinyl shlphone |
Country Status (7)
Country | Link |
---|---|
US (1) | US3106439A (d) |
BE (1) | BE586604A (d) |
CH (1) | CH377308A (d) |
DE (1) | DE1179536B (d) |
FR (1) | FR1245882A (d) |
GB (1) | GB915571A (d) |
NL (1) | NL247423A (d) |
Cited By (7)
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3024500A1 (de) * | 1980-06-28 | 1982-01-28 | Gewerkschaft Eisenhütte Westfalia, 4670 Lünen | Strebrandausbau |
Citations (5)
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 |
-
0
- NL NL247423D patent/NL247423A/xx unknown
- BE BE586604D patent/BE586604A/xx unknown
-
1959
- 1959-01-17 GB GB1802/59A patent/GB915571A/en not_active Expired
-
1960
- 1960-01-13 US US2107A patent/US3106439A/en not_active Expired - Lifetime
- 1960-01-15 CH CH40660A patent/CH377308A/de unknown
- 1960-01-15 FR FR815816A patent/FR1245882A/fr not_active Expired
- 1960-01-16 DE DEV17895A patent/DE1179536B/de active Pending
Patent Citations (5)
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)
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 |
---|---|
NL247423A (d) | |
DE1179536B (de) | 1964-10-15 |
FR1245882A (fr) | 1960-11-10 |
CH377308A (de) | 1964-06-30 |
CH40660A4 (d) | 1964-01-31 |
GB915571A (en) | 1963-01-16 |
BE586604A (d) |
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