US2791484A - Method of stabilizing regenerated cellulose textiles with aldoketene dimers and textile hand-modifying agents and products resulting therefrom - Google Patents
Method of stabilizing regenerated cellulose textiles with aldoketene dimers and textile hand-modifying agents and products resulting therefrom Download PDFInfo
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- US2791484A US2791484A US391370A US39137053A US2791484A US 2791484 A US2791484 A US 2791484A US 391370 A US391370 A US 391370A US 39137053 A US39137053 A US 39137053A US 2791484 A US2791484 A US 2791484A
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- United States
- Prior art keywords
- fabric
- textile
- emulsion
- regenerated cellulose
- aldoketene
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- 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.)
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- 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
- D06M13/10—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 oxygen
- D06M13/12—Aldehydes; Ketones
- D06M13/13—Unsaturated aldehydes, e.g. acrolein; Unsaturated ketones; Ketenes ; Diketenes
Definitions
- the present invention relates to stabilized regenerated cellulose textile materials and to methods of producing them.
- textile material is intended to include continuous filaments and staple fibers or yarns formed thereof, whether in the finished stage or at an intermediate stage in their production, as well as fabrics made from such yarns, whether knitted, woven, or felted, garments, so-called non-woven fabrics, and other fibrous articles.
- novel features of the invention are of special importance as applied to fabrics made of yarns formed from or comprising fibers or filaments of regenerated cellulose, including those predominantly of spun viscose rayon, and the invention will be discussed more in detail in connection with such application.
- stabilization is meant the rendering of the textile material, such as a woven fabric, resistant to progressive dimensional shrinkage on laundering or washing.
- While the primary object of the. present invention is to stabilize textile materials of regenerated cellulose, ancillary objects are to provide along with such stabilization an improved resistance to rupturing by tearing or flexing actions. It is also an ancillary object to provide a stabilization treatment which is adapted to imp-art softmess to the fabric or various degrees of stiffness or firmness. Other objects and advantages will be apparent from the description thereof hereinafter.
- Such dimers are at present generally considered to have the following formula:
- R is an alkyl or alkylene group having 8 to 18 carbon atoms.
- R may be octyl, capryl, lauryl, myristyl, hexadecyl, oleyl or octadecyl.
- reaction product of the cellulose is not positively known but it is believed to be either an ester having a formula as follows:
- R is the same as above and n may be any fractional, integral, or mixed number or the resulting product may possibly be an acetal having the formula in which R is the same as above, n is the same as above and m may be an integral number from 1 to 2, and Cell represents the residue of a cellulose molecule.
- the latter acetal structure includes the possibility of producing crosslinked molecules.
- reaction prod- 2,791,484 Fatented May 7, 1957 ucts or others are formed, it has been found that the products obtained in accordance with the process hereinafter outlined are rendered stable against dimensional shrinkage on laundering and they are unusually resistant to the removal of the dimer residues by hydrolytic action, particularly in alkaline medium. Hence, the products can be scoured under severe alkaline conditions without suffering loss of their stabilized character.
- the dimer is emulsified in an aqueous medium by means of a suitable emulsifier and an acidic catalyst is introduced to provide a pH in the emulsion between 1.0 and 2.0, preferably 1.2 to 1.4.
- the textile material is impregnated with such emulsion, such as by passing the material through a bath of the emulsion or by spraying the emulsion upon the material or by transferring the emulsion by means of rollers, wicks or the like to a travelling length of the textile material.
- any acid-stable emulsifier may be used.
- non-ionic emulsifiers such as ethylene oxide derivatives of partial esters of polyhydric alcohols, such as glycerine, sorbitol, mannitol, or inner ethers thereof with. higher fatty acids may be used.
- sorbitan monopalmitate, polyoxyethylene derivatives of sorbitan monopalmitate, polyoxyethylene derivatives or rosin, or of hydroabietyl alcohol or of glycerine may be used.
- the proportion of dimer in the emulsion may be from 2 to 10% by weight, preferably about 4 to 6%. Approximately one part by weight of the emulsifier is used for each five parts by weight of dimer.
- any acid or acid salt may be used which is capable of bringing the pH of the emulsion Within the range of 2.0 to 1.0.
- Acids such as sulfuric acid, hydrochloric acid, oxalic, maleic, and sulfamic acids may be used.
- acid salts such as sodium bisulfate may be used.
- strong acids such as sulfuric, hydrochloric or other mineral acid are used or acid salts thereof, such as sodium bisulfate are used, it is perferable to include within the medium, a buffer to prevent tendering or degr'adation of the regenerated cellulose.
- Buffers such as sodium sulfate, trisodium phosphate, disodium phosphate or monosodium phosphate, sodium citrate and so forth may be use.
- the proportion of acid may be from less than 1% up to 2% or more depending upon its strength, the amount being selected to give the desired pH within the range stated hereinabove.
- the amount of buffer may vary from less than 1%, such as from /2 to 2%, again in dependence upon the pH desired.
- a hand-modifying agent may be included within the emulsion.
- This agent may consist of a watersoluble cellulose ether, such as methyl cellulose, hydroxyethyl cellulose, carboxymethyl cellulose, or the like, polyvinyl alcohol, starch, or it may comprise a polymeric material of resinous character which can be dispersed Within the acid emulsion, such as acid-stable thermoplastic emulsions, especially those of polyvinyl acetate.
- the proportion may be from 1 to 4% by weight within theemulsion, the higher the proportion thereof, the firmer the hand obtained.
- the textile material may have the emulsion applied to it at room temperature after which excess is removed and the material is dried, such as at 240 to 250 P. Then the dried material is baked at a temperature to 300 to 350 for a period of time of one to seven minutes, the time being inversely proportional to the temperature selected for the operation.
- the material happens to be a fabric, particularly a woven fabric, it is preferred to support the fabric in a somewhat tensioned condition during the application of the emulsion and during the drying.
- the tension during application of the emulsion may be such as to distend the fabric to increase it from 1 to 6% in either or both the warp and filling directions.
- the tension may be such as to impart from 1 to 2% greater width (filling direction) and from 1 to 6% greater length (warp direction).
- the textile material is scoured to remove residual salts or acids and this may be accomplished in any aqueous detergent solution, such as a soap solution, a solution of soda ash, or synthetic detergents such as sodium N-methyl-N-oleoyl taurate, or mixtures thereof.
- the scouring may be performed at temperatures of 120 to 212 F. for a period of two to ten minutes, a preferred operation being carried out at 120 F. for about ten minutes.
- the textile material is dried under relaxed conditions. Then it may be steamed and finally dried in a condition such that the warp is relaxed and the width is about 1 to 2% greater than that after the immediately preceding drying under relaxed conditions. This steaming operation serves to remove any wrinkles that may be introduced by the drying under relaxed conditions.
- the wash test referred to is that of the Federal Specification CCC-T-191A Cotton Wash Test which involves boiling one hour in soap solution of a concentration of about /2 to 1% on the weight of the goods.
- the soap used herein was essentially sodium oleate.
- Example I An emulsion was produced containing per 1200 cc. of the emulsion, 50 grams of hexadecyl ketene dimer, 10 grams of the ethylene oxide ether of a sorbitan monooleate containing 5 ethylene oxide units per mole, 24 grams of sodium bisulfate and 6 grams of sodium sulfate by mixing the dimer and the emulsifier thoroughly while heating on a steam bath and then stirring in thoroughly 150 cc. of hot water to form an emulsion which emulsion was then added to 300 cc. of water and then diluted to 800 cc. of water. The sodium bisulfate was then dissolved in 150 cc.
- a woven textile fabric of challis construction whose filling and warp yarns consisted of spun viscose regenerated cellulose was passed through the emulsion in a pad and an auxiliary box associated therewith. After removal of excess by means of squeeze rolls, it was dried at 240 F. for three minutes under slight tension. It was then cured at 300 F. for five minutes under slight tension. It was scoured for ten minutes at 120 F.
- Example II An emulsion was prepared as in Example I except that the ketene dimer was replaced with a corresponding amount of the dimer of dodecyl ketene.
- the resulting fabric showed the following results on washing.
- Example 111 The procedure was the same as in Example I except that there was incorporated into the emulsion a watersoluble hydroxyethyl cellulose ether in an amount of 60 grams per 1200 cc. of the emulsion.
- the wash tests on the fabric produced the following results:
- Example IV The procedure was as in Example HI except the proportions of dimer and emulsifier were doubled, the proportions of the other ingredients of the emulsion remaining the same. As in Example III, the pH was also 1.3. The results of the wash tests on the fabric were as follows:
- Example V The procedure of Example III was followed except the proportions of dimer and emulsifier were reduced to 20 grams and 4 grams respectively per 1200 cc. of the emulsion.
- the pH was 1.3 as before and results of the wash tests were as follows:
- Example VI An emulsion was prepared containing 4 pounds of hexadecyl ketene dimer, 0.8 pound of the ethylene oxide ether of a sorbitan mono-oleate containing 5 oxyethylene units per mole, 2 pounds of sodium bisulfate and 0.5 pound sodium sulfate in water to make a total of 12 gallons having a pH of 1.3.
- the fabric initially of 36-inch width, was dried in a clip-tenter toa width of thirty-seven and a half inches. It was cured by passing through a pin tenter without overfeed at a temperature of 306 F. for four minutes. Its width was then thirtyseven and a half inches.
- the fabric was washed in rope form in an aqueous solution containing 1% soda ash and one-fourth percent of sodium N-methyl-N-oleoyl taurate. This scouring was efiected at F. for 15 minutes and was followed by a rinse and a squeeze. The fabric was then dried on a pin tenter with a number 4 overfeed to ,a 36-inch width. It was steamed'and dried on aclip-tenter' to a width of 37 inches. The changes in the measurements or dimensions from that of the initial fabric are summarized as follows:
- the emulsion contains between 4% and 6%, by Weight, of said dimer and from 1% to 4%, by weight, of a textile hand-modifying agent composed of a water-soluble hydroxyethyl cellulose.
- the dimer is that of hexadecyl ketene and the emulsion also contains, as a textile hand-modifying agent, from 1% to 4%, by weight, of a water-soluble hydroxyethyl cellulose dissolved in the aqueous phase of said emulsion.
- the method of stabilizing fabrics comprising yarns composed of regenerated cellulose fibers against progressive dimensional shrinkage under repeated washings which comprises impregnating said fabric with an aqueous emulsion having a pH of between 1.0 and 2.0 and containing between 2% and 10%, by weight, of a dimer of an aldoketene corresponding to the formula wherein R is selected from the group consisting of alkyl and alkylene radicals having from 8 to 18 carbon atoms, from about 0.4% to about 2% of an acid stable emulsifier and from about 1% to about 4% of a textile handmodifying agent, drying said impregnated fabric while under tension at a temperature between 240 and 250 F., baking said dried fabric while under tension at a temperature between 300 and 350 F. for a period of from 1 to 7 minutes, scouring said baked fabric and drying said scoured fabric in a relaxed condition.
- a regenerated cellulose textile fabric being resistant to progressive dimen sional shrinkage under repeated washings
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US391370A US2791484A (en) | 1953-11-10 | 1953-11-10 | Method of stabilizing regenerated cellulose textiles with aldoketene dimers and textile hand-modifying agents and products resulting therefrom |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US391370A US2791484A (en) | 1953-11-10 | 1953-11-10 | Method of stabilizing regenerated cellulose textiles with aldoketene dimers and textile hand-modifying agents and products resulting therefrom |
Publications (1)
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US2791484A true US2791484A (en) | 1957-05-07 |
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US391370A Expired - Lifetime US2791484A (en) | 1953-11-10 | 1953-11-10 | Method of stabilizing regenerated cellulose textiles with aldoketene dimers and textile hand-modifying agents and products resulting therefrom |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2221928A (en) * | 1988-08-17 | 1990-02-21 | Stephenson Group | Waterproofing treatment of textile materials |
WO2001063036A1 (en) * | 2000-02-25 | 2001-08-30 | Basf Aktiengesellschaft | Crease resistant finishing of cellulose-containing textiles, and laundry post-treatment agents |
WO2021261726A1 (en) * | 2020-06-25 | 2021-12-30 | 주식회사 엘지생활건강 | Composition for treating hair or fibers, comprising alkyl ketene compound |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB522204A (en) * | 1937-12-04 | 1940-06-12 | Deutsche Hydrierwerke Ag | Process for rendering textiles, paper, leather, furs and the like water repellent |
US2284896A (en) * | 1939-05-24 | 1942-06-02 | Du Pont | Process for making polymeric products and for modifying polymeric products |
US2436076A (en) * | 1946-09-27 | 1948-02-17 | Cluett Peabody & Co Inc | Method of stabilizing against shrinkage textile materials of regenerated cellulose |
US2627477A (en) * | 1949-10-06 | 1953-02-03 | Hercules Powder Co Ltd | Higher alkyl ketene dimer emulsion |
-
1953
- 1953-11-10 US US391370A patent/US2791484A/en not_active Expired - Lifetime
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB522204A (en) * | 1937-12-04 | 1940-06-12 | Deutsche Hydrierwerke Ag | Process for rendering textiles, paper, leather, furs and the like water repellent |
US2411860A (en) * | 1937-12-04 | 1946-12-03 | Heberlein Patent Corp | Process for rendering textiles, fibers, and the like water-repellent |
US2284896A (en) * | 1939-05-24 | 1942-06-02 | Du Pont | Process for making polymeric products and for modifying polymeric products |
US2436076A (en) * | 1946-09-27 | 1948-02-17 | Cluett Peabody & Co Inc | Method of stabilizing against shrinkage textile materials of regenerated cellulose |
US2627477A (en) * | 1949-10-06 | 1953-02-03 | Hercules Powder Co Ltd | Higher alkyl ketene dimer emulsion |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2221928A (en) * | 1988-08-17 | 1990-02-21 | Stephenson Group | Waterproofing treatment of textile materials |
GB2221928B (en) * | 1988-08-17 | 1992-07-15 | Stephenson Group | Treatment of textile materials |
WO2001063036A1 (en) * | 2000-02-25 | 2001-08-30 | Basf Aktiengesellschaft | Crease resistant finishing of cellulose-containing textiles, and laundry post-treatment agents |
US20030092804A1 (en) * | 2000-02-25 | 2003-05-15 | Jurgen Detering | Crease resistant finishing of cellulose-containing textiles, and laundry post-treatment agents |
WO2021261726A1 (en) * | 2020-06-25 | 2021-12-30 | 주식회사 엘지생활건강 | Composition for treating hair or fibers, comprising alkyl ketene compound |
KR20220000344A (en) * | 2020-06-25 | 2022-01-03 | 주식회사 엘지생활건강 | Composition for treating hair or fiber comprising alkyl ketene compound |
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