US3222119A - Process for treating cellulosic textile materials with bis(beta-methoxyethyl) sulfone - Google Patents
Process for treating cellulosic textile materials with bis(beta-methoxyethyl) sulfone Download PDFInfo
- Publication number
- US3222119A US3222119A US798339A US79833959A US3222119A US 3222119 A US3222119 A US 3222119A US 798339 A US798339 A US 798339A US 79833959 A US79833959 A US 79833959A US 3222119 A US3222119 A US 3222119A
- Authority
- US
- United States
- Prior art keywords
- sulfone
- bis
- beta
- weight
- textile materials
- 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
- 239000000463 material Substances 0.000 title description 24
- 239000004753 textile Substances 0.000 title description 21
- 238000000034 method Methods 0.000 title description 12
- BXRHGJXTOFSMNX-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethylsulfonyl)ethane Chemical compound COCCS(=O)(=O)CCOC BXRHGJXTOFSMNX-UHFFFAOYSA-N 0.000 title description 4
- 239000004744 fabric Substances 0.000 description 36
- 238000011084 recovery Methods 0.000 description 14
- 230000037303 wrinkles Effects 0.000 description 14
- 150000003457 sulfones Chemical class 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 238000010998 test method Methods 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- -1 beta-hydroxyethyl Chemical group 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 230000000717 retained effect Effects 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- 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 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 2
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 2
- QQLILYBIARWEIF-UHFFFAOYSA-N 2-(2-hydroxyethylsulfonyl)ethanol Chemical compound OCCS(=O)(=O)CCO QQLILYBIARWEIF-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 235000019645 odor Nutrition 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- This invention relates to modified cellulosic textile materials. More particularly, the invention relates to a method of treating cellulosic textile materials to improve their properties of dimensional stability, wash-and-wear, and wrinkle recovery without imparting a tendency toward chlorine retention after bleaching.
- treating agents have been found useful for improving the dimensional stability and wrinkle recovery of cellulosic textile materials.
- the treating agents which are known to be effective in this application usually have oneor more of the "following undesirable features: toxicity, expense, or relative inefficiency of the treating agent, instability to hydrolysis and heat, tendency toward chlorine retention when the treated material is bleached, development of objectionable odors in the treated material, yellowing with aging, yellowing on exposure to heat of an iron, or yellowing on treatment with hypochlorite bleach.
- One object of this invention is to provide means for improving the dimensional stability and wrinkle recovery of cellulosic textile materials.
- Another object is to provide such means by the use of treating agents which lack the aforementioned undesirable features of the treating agents previously known to be effective in improving the dimensional stability and wrinkle recovery of cellulosic textile materials.
- Example I An aqueous solution of 10% by weight of bis(betahydroxyethyl)sulfone and 3% by weight of sodium carbonate (both percentages based on the total weight of the solution) is padded on a cotton print cloth having a count of 80 x 80 to deposit in the cloth 10% by Weight of the sulfone, based on the weight of the untreated cloth. The cloth is then dried at 220 F. for 3 minutes and cured at 310 F. for 4 minutes.
- the treated cloth has a wrinkle recovery of 259 (warp plus filling), as determined by ASTM test method D1295 531", compared to a wrinkle recovery of 100 (warp plus filling) determined on the untreated cloth.
- the treated cloth is washed in accordance with AATCC Standard Test Method 14-1953 with the following exceptions: (1) the process is run continuously for 120 minutes instead of 60, with a 100 minute wash cycle, (2) sufiicient sodium carbonate is added to obtain a pH of 10, (3) steam is injected continuously through the wash cycle to maintain the temperature at 212 F., and (4) the temperature of the first rinse is 160 F. After having been washed according to this procedure and dried, the treated fabric has a wrinkle recovery of 241 (warp plus filling). There is no further loss in Wrinkle recovery of the treated fabric after four subsequent washings according to the same procedure. The treated fabric shows less shrinkage after washing than the untreated fabric.
- the treated fabric is subjected to AATCC Tentative Test Method 69-1958.
- the test shows essentially no damage to the fabric by retained chlorine.
- Example 11 An aqueous solution of 6% by weight of bis(-beta methoxyethyDsulfone and 3% by weight of sodium carbonate (both percentages based on the totalweight of the solution) is padded on a cotton print cloth having a count of x 80 to deposit in the cloth 5% by weight of the sulfone, based on the weight of the untreated cloth. The cloth is then dried at 200 F. for 3 minutes and cured at 320 F. for 3 minutes.
- the treated fabric is washed for 10 minutes at F. with an aqueous solution of 0.01% by weight of an alkyl aryl sulfonate detergent and 0.01% by weight of tetrasodium pyrophosphate (both percentages based on the total weight of the solution), rinsed at 100 'F. for 10 minutes, and then rinsed again at 100 F. for 10 minutes.
- the treated fabric shows less shrinkage after washing than the untreated fabric and has a wrinkle recovery of 184 (warp plus filling), as determined by ASTM test method D1295-53T, compared to a wrinkle recovery of 100 (warp plus filling) determined on the untreated cloth.
- the treated fabric is subjected to AATCC Tentative Test Method 69-1958.
- the test shows essentially no damage to the fabric by retained chlorine.
- Example III An aqueous solution of 8% by weight of bis(betamethoxyethyl)sulfone and 1% by weight of sodium hydroxide (both percentages based on the total weight of the solution) is padded on a cotton print cloth having a count of 80 x 80 to deposit in the cloth about 7% by Weight of the sulfone, based on the weight of the untreated cloth. The cloth is then dried at 200 F. for 3 minutes and cured at 320 F. for 3 minutes.
- the treated cloth is washed for 10 minutes at 100 F. with an aqueous solution of 0.01% by weight of an alkyl aryl sulfonate detergent and 0.01% by weight of tetrasodium pyrophosphate (both percentages based on the total weight of the solution), rinsed at 100 'F. for 10 minutes, and then rinsed again at 100 F. for 10 minutes.
- the treated fabric shows less shrinkage atfer washing than the untreated fabric and has a wrinkle recovery of 200 (warp plus filling), as determined by ASTM test method D1295-53T, compared to a wrinkle recovery of 100 (warp plus filling) determined on the untreated cloth.
- the treated fabric is subjected to AATCC Tentative Test Method 694958.
- the test shows essentially no damage to the fabric by retained chlorine.
- the textile materials which are treated by the process of this invention are materials containing cellulosic hydroxyl groups, e.g., cotton, rayon, and linen. They may be treated as fabrics or as yarns from which the fabrics are woven.
- the water-soluble compounds with which the oellulosic textile materials are treated to improve their properties of dimensional stability and wrinkle recovery are com compounds corresponding to the general formula:
- the amount of water-soluble sulfone treating agent incorporated into the textile material may vary from about 120% by Weight, based on the weight of the untreated textile material.
- the amount of water in the treating bath may be varied for ease of operation in incorporating this amount of the treating agent into the textile material.
- Suitable catalysts are the strongly basic catalysts such as the hydroxides, carbonates, and phosphates of alkali metals, i.e., Li, Na, K, Rb, and Cs; especially preferable are sodium or potassium carbonate and sodium or potassium hydroxide.
- the aqueous treating bath should contain about 0.55% preferably 13%, by weight of alkaline catalyst, based on the total weight of the bath.
- the process of the invention comprises impregnating a cellulosic textile material with an aqueous solution of the water-soluble sulfone treating agent and an alkaline catalyst, drying the impregnated material, and curing to react the treating agent with the textile material.
- Impregnation of the textile material with the treating bath can be effected by any of the impregnation techniques commonly used in the textile industry, eflicaciously by padding.
- the impregnated material may be dried at room temerature or at elevated temperatures below curing temperature. Curing is accomplished by heating the dried fabric at temperatures in the range of 250-400 F. for about 4 0.5-20 minutes, preferably by heating at 300-350 F. for 1-3 minutes, to react the treating agent with the textile material.
- the treated textiles obtained by the process of the invention have improved properties of dimensional stablility and wrinkle recovery, do not show a tendency toward chlorine retention after bleaching, and do not lose their improved properties when subjected to acid or alkaline hydrolysis.
- a process which comprises impregnating a cellulosic textile material containing cellulosic hydroxyl groups with an aqueous solution of an alkaline catalyst and bis(betamethoxyethyDsulfone.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DENDAT1414494 DE1414494A1 (OSRAM) | 1959-03-10 | ||
| US798339A US3222119A (en) | 1959-03-10 | 1959-03-10 | Process for treating cellulosic textile materials with bis(beta-methoxyethyl) sulfone |
| ES0255967A ES255967A1 (es) | 1959-03-10 | 1960-02-23 | Procedimiento de mejora de materiales textiles celulësicos |
| DE19601419494 DE1419494A1 (de) | 1959-03-10 | 1960-03-10 | Verfahren zum Behandeln von Cellulosetextilmaterial |
| GB8453/60A GB936479A (en) | 1959-03-10 | 1960-03-10 | Treatment of cellulosic textile materials |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US798339A US3222119A (en) | 1959-03-10 | 1959-03-10 | Process for treating cellulosic textile materials with bis(beta-methoxyethyl) sulfone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3222119A true US3222119A (en) | 1965-12-07 |
Family
ID=25173152
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US798339A Expired - Lifetime US3222119A (en) | 1959-03-10 | 1959-03-10 | Process for treating cellulosic textile materials with bis(beta-methoxyethyl) sulfone |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3222119A (OSRAM) |
| DE (2) | DE1419494A1 (OSRAM) |
| ES (1) | ES255967A1 (OSRAM) |
| GB (1) | GB936479A (OSRAM) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3338661A (en) * | 1964-10-28 | 1967-08-29 | Dow Corning | Cellulosic fabrics rendered crease resistant and water repellant through treatment with compositions comprising catalyst-water repellant silicones and sulfone crosslinking agents |
| US3477802A (en) * | 1963-03-19 | 1969-11-11 | Stevens & Co Inc J P | Modification of cellulose,polyvinyl alcohol and starch with compounds characterized by ethylene radicals having an electron attracting group which stabilizes carbanions on one carbon atom thereof and an alkoxy or hydroxy group on the other |
| US3492080A (en) * | 1962-06-12 | 1970-01-27 | Stevens & Co Inc J P | Reaction of polymeric materials containing reactive hydrogen with monofunctional beta-oxyethyl sulfones |
| US3498736A (en) * | 1961-03-20 | 1970-03-03 | Gaf Corp | Inhibiting cellulose fiber yellowing in alkaline processing at elevated temperatures through utilization of boron salts |
| 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 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3359061A (en) * | 1961-12-19 | 1967-12-19 | Clark M Welch | Process for making alkoxyethylsulfonylethyl ethers of cellulose |
| US3230031A (en) * | 1962-02-06 | 1966-01-18 | Clark M Welch | Process for making aryloxyethylsul-fonylethyl ethers of cellulose |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2524399A (en) * | 1948-07-07 | 1950-10-03 | Us Rubber Co | Cellulose treated with di-vinyl sulfone to shrinkproof |
| US2539704A (en) * | 1948-07-07 | 1951-01-30 | Us Rubber Co | Treatment of hydroxylated polymers |
| US2670265A (en) * | 1954-02-23 | Process | ||
| GB779781A (en) * | 1952-06-09 | 1957-07-24 | Hoechst Ag | Water insoluble dyestuffs and a process for producing fast dyeings and prints therewith |
| US2933367A (en) * | 1957-10-29 | 1960-04-19 | Wilson A Reeves | Flame-resistant cellulosic textiles and process of reacting cellulose ether textiles with aziridinyl phosphine oxide or sulfide |
-
0
- DE DENDAT1414494 patent/DE1414494A1/de active Pending
-
1959
- 1959-03-10 US US798339A patent/US3222119A/en not_active Expired - Lifetime
-
1960
- 1960-02-23 ES ES0255967A patent/ES255967A1/es not_active Expired
- 1960-03-10 DE DE19601419494 patent/DE1419494A1/de active Pending
- 1960-03-10 GB GB8453/60A patent/GB936479A/en not_active Expired
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2670265A (en) * | 1954-02-23 | Process | ||
| US2524399A (en) * | 1948-07-07 | 1950-10-03 | Us Rubber Co | Cellulose treated with di-vinyl sulfone to shrinkproof |
| US2539704A (en) * | 1948-07-07 | 1951-01-30 | Us Rubber Co | Treatment of hydroxylated polymers |
| GB779781A (en) * | 1952-06-09 | 1957-07-24 | Hoechst Ag | Water insoluble dyestuffs and a process for producing fast dyeings and prints therewith |
| US2933367A (en) * | 1957-10-29 | 1960-04-19 | Wilson A Reeves | Flame-resistant cellulosic textiles and process of reacting cellulose ether textiles with aziridinyl phosphine oxide or sulfide |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3498736A (en) * | 1961-03-20 | 1970-03-03 | Gaf Corp | Inhibiting cellulose fiber yellowing in alkaline processing at elevated temperatures through utilization of boron salts |
| US3492080A (en) * | 1962-06-12 | 1970-01-27 | Stevens & Co Inc J P | Reaction of polymeric materials containing reactive hydrogen with monofunctional beta-oxyethyl sulfones |
| US3477802A (en) * | 1963-03-19 | 1969-11-11 | Stevens & Co Inc J P | Modification of cellulose,polyvinyl alcohol and starch with compounds characterized by ethylene radicals having an electron attracting group which stabilizes carbanions on one carbon atom thereof and an alkoxy or hydroxy group on the other |
| 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 |
| US3338661A (en) * | 1964-10-28 | 1967-08-29 | Dow Corning | Cellulosic fabrics rendered crease resistant and water repellant through treatment with compositions comprising catalyst-water repellant silicones and sulfone crosslinking agents |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1419494A1 (de) | 1968-10-10 |
| ES255967A1 (es) | 1960-04-16 |
| GB936479A (en) | 1963-09-11 |
| DE1414494A1 (OSRAM) |
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