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United States Patent Office Patented Feb 2,780,511 United States Patent Office Patented Feb. 5, 1957 2 advantageous when applied to the viscose staple rayon 2,780,511 having a permanent structural crimp. This crimp, in con trast to the mechanically applied crimp of the thermo oD of MAKING CELLULOSE ACETATE plastic fibers, originates in the fine inner structure of the XTILE FIBERS BY ACETYLIZATION OF fibers and is permanent through spinning, weaving, Wash GENERATED CELLULOSE FIBERs ing, ironing and other similar fabric treatments, which Takagi, Tokyo, Japan, assignor to Toho Rayon makes such viscose fiber particularly valuable. The per Co., Ltd., Tokyo, Japan, a corporation of Japan manent structural crimp of such viscose staple rayon is No Drawing. Application May 14, 1953, retained throughout the acetylation process of the present ... " . Serial No. 355,150 10 invention. - The invention may be applied to continuous cellulosic 3 Claims. (CI. 8-121) fibers which may be lightly twisted together to form a yarn or rope prior to acetylation, or it may be applied to a This invention relates to the preparation of cellulose mass of loose staple fibers which may be conveyed through acetate fiber having an acetic acid content of at least 40% 5 the several steps of the process on a suitable belt or wire by vapor phase acetylation of cellulosic fibers while re mesh conveyor, or the like. If desired, the cellulosic taining the fiber structure. fibers, either continuous or staple, may be loosely woven It has previously been proposed to acetylate cellulosic or knitted to form a fabric which may then be subjected fibers while retaining their fiber structure by carrying out to the acetylation process of the present invention. the acetylation both in liquid and vapor phase. However, 20 The invention is characterized in that the cellulosic it has hitherto been impossible to produce a cellulose fiber is impregnated with an acetylation catalyst from an acetate fiber having an acetic acid content from 40-62% aqueous solution thereof, dried to remove at least a por by weight (which corresponds approximately to cellulose tion of the water content of the impregnated fiber, treated with acetic acid vapor to replace and remove the residual diacetate or triacetate) free from discoloration and brittle 25 water content, then acetylated with acetic acid anhydride ness and having at the same time a high tensile strength in vapor form. The entire process is preferably carried and low elongation. Direct acetaylation of cellulose has out with the cellulosic fiber advancing continuously hithertoduce only generally cellulose beenmonoacetate employed fiber, commercially while fibers to having pro- through each successive step, particularly the steps involv a higher acetic acid content have been made commer ing treatment with acetic acid and with acetic anhydride. cially by complete acetylation followed by a dry spinning 30 Among the acetylation catalysts which are suitable for procedure involving partial hydrolysis to reduce the acetic use in the present invention are salts, of which there are acid content. In the first case, the acetate fiber is a mere , particularly preferred the acetates such as potassium, modification of ordinary cellulose fiber possessing essen sodium, or lithium acetates; the phosphates, such as Sec.- tially the same chemical properties and dry affinity as or sodium phosphate, tert-sodium phosphate, the ammonium dinary cellulose. Dry spun cellulose acetate fiber on the 35 phosphates, etc.; the chlorides, such as zinc chloride, other hand, even when the acetic acid content has been cupric chloride, aluminum chloride, stannous chloride, reduced to approximately that of cellulose diacetate, pos- : stannic chloride, etc.; the sulfates, such as copper sulfate, sesses undesirably low tensile strength and high elongation. ... aluminum sulfate, zinc sulfate, alum, etc.; and the oxa One object of the present invention is to provide a lates, such as ammonium oxalate, ammonium acid oxa cellulose acetate fiber having an acetic acid content corre 40 late, etc.; and mixtures of any two or more of such salts. sponding approximately to cellulose diacetate and cellu The catalysts are preferably applied to the cellulosic lose triacetate and having a high tensile strength together ... fiber from aqueous solution which may suitably contain with low elongation and essentially the same dyeing from about 10-20% by weight of the desired salt. The characteristics as dry-spun acetate fiber. fiber may be passed through a container filled with the Another object is to provide a cellulose acetate fiber 45 aqueous salt solution or the solution may be sprayed onto having a permanent structural crimp and having an acetic the fibers, the impregnation preferably being carried out acid content from 40-62% by weight, preferably from . at room temperature (although elevated temperatures 40-55% by weight. - may be employed if desired) at which temperature a contact time of from about 10 to about 60 minutes is em Still a further object is to provide a process for con 50 ployed to insure satisfactory impregnation of the fiber. tinuous vapor phase acetylation of cellulosic fibers while The impregnated fiber, which contains about 5-15% by retaining the fibrous structure of the cellulosic material. weight of the catalyst, is then passed between squeeze A further object is to provide a method for the vapor , ; rolls to remove excess water, or it may be centrifuged if phase acetylation of celluosic fibers, particularly fibers of desired, and further dried in hot air. The dried fiber regenerated cellulose, while retaining the fiber structure, 55 ordinarily has a water content at this point of from without discoloration of the fibers. 40–75% by weight, usually from 55-65% by weight. Other and further objects will be apparent from the In order to minimize the quantity of acetic anhydride description which follows. ... that is required for the acetylation reaction, it is preferred The present invention may be employed for the produc to replace and remove the residual water content of the tion of cellulose acetate fibers from a wide variety of 60 impregnated fibers following the aforementioned drying cellulose fibers, including cotton, regenerated cellulose operation by passing the fibers continuously through a and wood-pulp. However, the invention is particularly closed chamber filled with acetic acid vapor and main 2,780,511 3 4. tained at a temperature of 100 to 130 C., preferably densed and separated by fractional distillation, the acetic at a temperature of 105 to 115° C. Removal and re anhydride recovered being returned to the act ylation placement of residual water ordinarily is completed in chamber where it is revaporized. from 10 to 45 minutes, the best results having been ob After the desired degree of acetylation has been tained in a period of about 25 to 35 minutes. achieved the fiber, carried by the conveyor belt, is with Immediately following the exposure to acetic acid drawn through a slit in the chamber wall and is then vapor the fiber is advanced into a separate chamber filled washed with water, oiled and dried in air at 50-70' C. with acetic anhydride vapor and maintained at about 100 The resulting cellulose acetate fiber retains the péirmanent to 140 C., preferably at about 110 to 130 C. In order structural crimp of the original viscose rayon fiber and to achieve the desired degree of acetylation the fiber must 0. has an acetic acid content of 52% by weight. be maintained in contact with acetic anhydride vapor for Example II a period of at least 3 hours, preferably from 4 to 7 hours, during which time the supply of acetic anhydride vapor to Spun-dyed viscose staple fiber having a permanent the reaction chamber is constantly renewed. The acetic structural crimp is treated as described in Example I, ex acid present in the fiber as it is introduced into the acet 5 cept that an aqueous solution of potassium acetate is used ylation chamber together with the acetic acid formed in place of the sodium acetate solution, the amount of during acetylation reaction is constantly withdrawn along catalyst contained in the fiber being about 8% by weight with the excess acetic anhydride vapor. The mixture is of the fiber. The chamber containing acetic anhydride is condensed and then distilled in a conventional stainless maintained at a temperature of 120° C. and the tif steel plate column to separate the anhydride from the exposure of the fiber to the acetic anhydride vapors i acid. The anhydride is then recirculated to the acetyla hours. The resulting product has an acetic acid con tion chamber. of 53%, the acetylated fiber having the same permane The acetylated fiber is continuously withdrawn from structural crimp as the original viscose staple fibers. The the acetylation chamber through a restricted opening, color of the original dyed viscose staple may be black, washed with water, oiled and dried. blue, brown, orange, yellow, navy blue, pink, purple, red, The cellulose acetate fiber of the present invention has or any other color and the shade of these colors is not unexpectedly excellent physical properties as compared changed by the acetylation procedure. with the convential dry-spun acetate fibers, having a dry Example III tensile strength of at least 1.70 gram/denier, a wet ten sile strength of at least 1.30 gram/denier, a loop tensile Yarn made from viscose rayon staple fibers having a strength of at least 1.25 gram/denier, while having an permanent structural crimp is treated as described in Ex ultimate elongation no greater than about 25% (dry) and ample I, except that zinc sulfate is used as the catalyst about 22% (wet). The physical properties of the pre and the acetylation is carried out for five hours at 130 ferred fibers of the present invention having an acetic acid C.
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