US2333770A - Conditioning cellulose acetate yarn - Google Patents
Conditioning cellulose acetate yarn Download PDFInfo
- Publication number
- US2333770A US2333770A US246201A US24620138A US2333770A US 2333770 A US2333770 A US 2333770A US 246201 A US246201 A US 246201A US 24620138 A US24620138 A US 24620138A US 2333770 A US2333770 A US 2333770A
- Authority
- US
- United States
- Prior art keywords
- yarn
- conditioning
- cellulose acetate
- cellulose
- yarns
- 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
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- 230000003750 conditioning effect Effects 0.000 title description 23
- 229920002301 cellulose acetate Polymers 0.000 title description 17
- 239000003795 chemical substances by application Substances 0.000 description 21
- 229940081735 acetylcellulose Drugs 0.000 description 16
- 238000009940 knitting Methods 0.000 description 14
- 229920002678 cellulose Polymers 0.000 description 13
- 239000001913 cellulose Substances 0.000 description 12
- 238000009987 spinning Methods 0.000 description 11
- 239000004753 textile Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000009941 weaving Methods 0.000 description 8
- -1 Triethanolamine diacetate monopropionate Chemical compound 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000835 fiber Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000010775 animal oil Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 230000001050 lubricating effect Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000008158 vegetable oil Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 3
- 239000004902 Softening Agent Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 238000004804 winding Methods 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- DJYQGDNOPVHONN-UHFFFAOYSA-N 2-[bis(2-acetyloxyethyl)amino]ethyl acetate Chemical compound CC(=O)OCCN(CCOC(C)=O)CCOC(C)=O DJYQGDNOPVHONN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920008347 Cellulose acetate propionate Polymers 0.000 description 2
- DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000012237 artificial material Substances 0.000 description 2
- 229920006218 cellulose propionate Polymers 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- BFIAIMMAHAIVFT-UHFFFAOYSA-N 1-[bis(2-hydroxybutyl)amino]butan-2-ol Chemical compound CCC(O)CN(CC(O)CC)CC(O)CC BFIAIMMAHAIVFT-UHFFFAOYSA-N 0.000 description 1
- CSPLCTYUMAHGLL-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol propanoic acid Chemical compound CCC(O)=O.CCC(O)=O.CCC(O)=O.OCCN(CCO)CCO CSPLCTYUMAHGLL-UHFFFAOYSA-N 0.000 description 1
- ZAMLGGRVTAXBHI-UHFFFAOYSA-N 3-(4-bromophenyl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(CC(O)=O)C1=CC=C(Br)C=C1 ZAMLGGRVTAXBHI-UHFFFAOYSA-N 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- TXFNJUJUNSLXBA-UHFFFAOYSA-N acetic acid 2-[bis(2-hydroxyethyl)amino]ethanol Chemical compound C(C)(=O)O.C(C)(=O)O.N(CCO)(CCO)CCO TXFNJUJUNSLXBA-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229920001727 cellulose butyrate Polymers 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- OJMXDPYZLDLHCF-UHFFFAOYSA-N oxolan-2-ylmethyl formate Chemical compound O=COCC1CCCO1 OJMXDPYZLDLHCF-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002759 woven fabric Substances 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
- D06M13/322—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 nitrogen
- D06M13/372—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 nitrogen containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
-
- 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
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/188—Monocarboxylic acids; Anhydrides, halides or salts thereof
-
- 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
- D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
-
- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2964—Artificial fiber or filament
- Y10T428/2965—Cellulosic
Definitions
- This invention relates to the conditioning of textile yarns and more particularly to the conditioning of filaments and yarns composed of organic derivatives of cellulose such as cellulose acetate, cellulose propionate, cellulose acetate propionate, and cellulose acetate butyrate, to render them more amenable to textile operations such as knitting and the like.
- a still further object is to provide an improved method for the conditioning of yarns, particularly those composed of or containing organic derivatives of Cellulose such as cellulose acetate, whereby the yarn is rendered soft and pliable and capable of employment in a variety of textile operations where complicated designs or stitches are employed.
- Another object is to provide an improved type of yarn which is especially amenable to textile operations including circular important that the yarn be soft and pliable in order that it may conform readily to the contour of the needles and thus produce a closely knit fabric free from such defects as "stitch distortion,” pin holes,” laddering,” and the like.
- softening agents such as polyhydric alcohols and similar agents as ingredients of yarn conditioning or lubricating formulas, generally in connection with mineral, animal or vegetable oils. It has been found, however, that most of the known softening agents and the various formulas containing them have certain drawbacks, one of the most serious of which is high vapor pressure, and in some cases too drastic a solvent action on the yarn. Many of such agents possess slight or insufllcient solvent power for the lubricants with which they are used, and it is accordingly necessary to employ blending agents or emulsifying agents in order to obtain operable yarn treating formulas. In addition, many of the known softening andlubricating agents are insufliciently soluble in water to permit satisfactory removal by aqueous scour baths.
- This invention has as its principal object to provide an entirely new class of yarn conditioning agents which are particularly adapted for the treatment of yarns composed of or containing organic derivatives of cellulose and capable of lubrlcating, softening and rendering such yarns knitting, weaving, spinning and the like. Other objects will appearhereinafter.
- R, R R and R? are the same or different substituted or unsubstituted alkyl, cycloalkyl, aryl or heterocyclic groups and n is 1, 2, 3, etc,
- these compounds when employed as described in the detailed examples set forth below have slight solvent and/or softening action on cellulose organic derivative yarns which ren-.
- These compounds may be prepared by reacting a tertiary amine containing one or more hydroxyl groups with suitable, organic acids, acid anhydrides, chlorides, etc., to prepare the corresponding ester.
- suitable, organic acids, anhydrides, and chlorides are acetic acid and acetic anhydride,;aropionic acid and propionic anhydride, propionyl chloride and the like.
- Triethanolamine triacetate is applied to textile Preparation of triethanolamine trz'acetate materials (silk, wool, cellulose acetate, cotton,
- the amount of conditioning q d 'o t applied may vary fromt 4-25% by weight of the yarn, and if the yarn is intended for weaving, A mixture of 150 parts triethanolamine, '75 the amount of liquid applied may vary between parts propionic acid, 125 parts acetic acid, 5 15% by weight of the yarn.
- Cellulose acetate parts concentrated sulphuric acid, and parts filaments or fibers treated as described are quite benzene is distilled so that the benzene is auto- 50 soft and pliable and give improved results in varimatically separated from the water and returned ous operations such as weaving, knitting, etc.
- these compounds have exceptional solvent pow- Parts ers which enable them to dissolve mineral oils Triethanolamine tripmpionate 80 nd blown and unblown, drying and semi-drying, 5 Blown olive oil 20 vegetable and animal oils and accordingly they may be, and preferably'are, employed as ingre- EXAMPLE 4 washers of yarn conditioning or lubricating for- Parts mulas in conjunction agents which fllIiC- Tripropanolamine dipropionate monoacetate 20 tion wholly or partially as lubricants.
- Light mineral 11 30 In the following examples and description we have set forth several of the preferred embodi- EXAMPLE 5 ments of our invention, but they are included Parts merely for purposes of illustration and not as a Tributanol amine monovalerate 70 limitation thereof. Blown sperm nil 3o Ethyl di-y-hydroxy propylamino p-methoxy combination used in making up the spinning solution, and the degree of softness or pliability desired in the yarn, etc.
- conditioning agent is to be applied to the yarn after spinning, this may be done by bringing the yarn in contact with a wick, roll,
- liquid may be applied by immersion, spray, or otherwise.
- 'It may, for example, be applied to the yarn inside or outside the spinning cabinet, between the guide and godet roll, between the godet or other roll or guide and the point of winding and/or twisting.
- the liquid may even be applied to the yarn after winding onto cones, spools, bobbins, or the like or by'the so-called bobbin to bobbin method.
- the liquid may be applied to the yarn prior to, or after, cutting into staple lengths.
- Triethanolamine monobutyratedipropionate Any of the above compositions may be applied to the yarn intended for use in circular knitting by means of a bath, wick, spray, roller, pad or any suitable means.
- the amount of conditioning liquid applied may vary between 525% by weight of the yarn. Usually, however, the amount of conditioning liquid applied is about 10-15% by weight of the yarn.
- Yarn composed of cellulose acetate conditioned as described above gives excellent results when used in the circular knitting process.
- a cellulose organic acid ester yarn such as a yarn composed of cellulose acetate
- about 4 to 25% or more by weight based on the weight of the dry yarn, may be satisfactory, while if the yarn is intended for weaving, the amount may vary between about 1 and 5%.
- the conditioning agents of our invention may be applied by a wide variety-of methods.
- the agent as an ingredient of the Spinning dope from which the filaments are formed, the amount of the agent so employed depending upon a number of factors, such as the particular cellulos derivative used in making the yarn, the solvent or solvent is desired to control the solvent or softening action of the conditioning agent, the amount of the agent may be adjusted as, for example, by reducing the amount of the agent and correspondingly increasing the amount of oil or other ingredient.
- the conditioning agents and formulas described herein ar applicable to the conditioning of many other types of cellulose derivative yarns such as those composed of or containing cellulose propionate, cellulose butyrate, cellulose acetate propionate, cellulose acetate butyrate, ethyl cellulose, methyl cellulose, benzyl cellulose and others, as well as to the conditioning of silk, wool, cotton, viscose and other natural or artificial materials.
- yam as used herein and in the claims is to be understood as including a single filament, a plurality of filaments associated into the form of thread, either of high or low twist single or multiple threads associated or twisted together, composite threads composed of a mixture of natural and artificial filaments or a compositethread formed by twisting together individual strands of natural or artificial materials, as well as cut staple fibers produced from natural and/or artificial filament or threads and spun yarn produced from such stable fibers.
- the yarn conditionin agents of our invention are exceptionally good solvents for a wide variety of mineral, blown and unblown, drying and semi-drying animal and vegetable oils such as cottonseed, olive, castor, neat'sfoot, sperm and other oils. This enables them to be used with any of such oils in making up a variety of yarn treating formulas of varying composition.
- the yarn conditioning method and compositions of our invention possess many outstanding advantages.
- the fundamental and outstanding characteristic of the agents employed in accordance with the invention is their ability to soften yarns, especially those composed of or containing organic derivatives of cellulose such as cellulose acetate and render them soft and pliable and amenable to various textile operations, especially operations such as those involved in weaving and knitting where complicated designs or stitches are employed, without too drastic an action on the eating assistants in conjunction with these oils when applied to such yarns.
- due to their solubility in water they may be readily removed from yarns and fabrics by means of the usual aqueous scour baths.
- the process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, and the like which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component triethanolamine monoacetate dipropionate.
- Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning, and the like, impregnated with a lubricant comprising triethanolamine mono-acetate dipropionate,
Description
Patented Nov. 9, 1943 CONDITIONING CELLULOSE ACETATE YARN Joseph B. Dickey and James B. Normington, Rochester, N. Y., assignors to Eastman Kodak Company, Rochester; N
New Jersey Y., a corporation of No Drawing. Application December 16, 1938, Serial No. 246,201
,2 Claims. (01. 8-1425 This invention relates to the conditioning of textile yarns and more particularly to the conditioning of filaments and yarns composed of organic derivatives of cellulose such as cellulose acetate, cellulose propionate, cellulose acetate propionate, and cellulose acetate butyrate, to render them more amenable to textile operations such as knitting and the like.
As is well known in the manufacture of yarns, particularly those composed of or containing cellulose organic derivatives, it is necessary to treat the yarn in order to reduce the tendency toward breakage of the individual filaments or fibers when they are subjected to various mechanical strains and to lubricate the yarn in order to facilitate handling in such operations as spinning, twisting, winding and reeling. It is also necessary to treat yarn to adapt it for use as warp or filling or for the manufacture of various types of knitted fabrics. In knitting, it is particularly moved from the yarns by the usual scour baths.
A still further object is to provide an improved method for the conditioning of yarns, particularly those composed of or containing organic derivatives of Cellulose such as cellulose acetate, whereby the yarn is rendered soft and pliable and capable of employment in a variety of textile operations where complicated designs or stitches are employed. Another object is to provide an improved type of yarn which is especially amenable to textile operations including circular important that the yarn be soft and pliable in order that it may conform readily to the contour of the needles and thus produce a closely knit fabric free from such defects as "stitch distortion," pin holes," laddering," and the like.
Heretofore it has been proposed to employ softening agents such as polyhydric alcohols and similar agents as ingredients of yarn conditioning or lubricating formulas, generally in connection with mineral, animal or vegetable oils. It has been found, however, that most of the known softening agents and the various formulas containing them have certain drawbacks, one of the most serious of which is high vapor pressure, and in some cases too drastic a solvent action on the yarn. Many of such agents possess slight or insufllcient solvent power for the lubricants with which they are used, and it is accordingly necessary to employ blending agents or emulsifying agents in order to obtain operable yarn treating formulas. In addition, many of the known softening andlubricating agents are insufliciently soluble in water to permit satisfactory removal by aqueous scour baths.
This invention has as its principal object to provide an entirely new class of yarn conditioning agents which are particularly adapted for the treatment of yarns composed of or containing organic derivatives of cellulose and capable of lubrlcating, softening and rendering such yarns knitting, weaving, spinning and the like. Other objects will appearhereinafter.
These objects are accomplished by the following invention which, in its broader aspects, comprises the discovery that compounds having the formula:
where R, R R and R? are the same or different substituted or unsubstituted alkyl, cycloalkyl, aryl or heterocyclic groups and n is 1, 2, 3, etc,, maybe used as yarnconditioning agents and particularly as softening agents, with or without the addition of animal, mineral, or vegetable oils, in the treatment of yarns composed of or containing organic derivatives of cellulose. We have found that these compounds when employed as described in the detailed examples set forth below have slight solvent and/or softening action on cellulose organic derivative yarns which ren-.
der such yarns soft and pliable without at the same time having too drastic an action thereon.
These compounds may be prepared by reacting a tertiary amine containing one or more hydroxyl groups with suitable, organic acids, acid anhydrides, chlorides, etc., to prepare the corresponding ester. Typical examples of organic acids, anhydrides, and chlorides, are acetic acid and acetic anhydride,;aropionic acid and propionic anhydride, propionyl chloride and the like.
pounds of this type are as follows:
Typical examples of compounds which, in ac- Our invention will be more readily undercordance with our invention, we have found to stood by reference to the following examples in be valuable plasticizers, are given in the followwhich typical applications of the invention are ing table. set forth.
DERIVATIVES or Txm'rrmNoLAmrm Compound Formula Boiling range Triethanolamine triacetate N(CaH40C0 CH5); 197-201L7 C./l6 mm,
(CQHAOCOCHS)! Triethanolamine diacetate monopropionate. ]N\ 215223 0.125 mm.
cnnoooclu.
/C2H4OCOCHI Triethanolamine dipropionate monoacetate N 184-187" 0.15 mm.
(OaH 0COC2Hi): Triethanolamine tripropionate N(C-:H4OCOCH5)3....- 2l8-223 C./2l mm, 'lrietbanolamine trihexoato N(C3H0COC5H1])L 210-220 0.]2-3 mm.
Examples of the preparation of the typical com- EXAMPLE 1 Triethanolamine triacetate is applied to textile Preparation of triethanolamine trz'acetate materials (silk, wool, cellulose acetate, cotton,
' viscose, etc.) by means of a Wick, roller, spray 150 parts of triethanolamine are treated with b th, pad, t t fa ilitate their knitting weav 320 parts acetic anhydride. Heat is given off m spinning and the like. If t yam is and the solution is refluxed for two hours. 400 tended primarily for knitting the amount of parts of the triacetate are obtained by distilladitioning liquid applied may vary from 425% tion, having a boiling point b of by weight of the yarn, and if the yarn is intend- 200 C. ed for weaving, the amount of liquid applied may vary between 1-5% by weight of the yarn. Preparatzon of triethanolamine tripromonate EXAMPLE 2 Seven equivalents of propionyl chloride are added slowly to two parts triethanolamine and A Conditioning liquid is made p as fOIIOWSI the whole heated on the water bath until no more Parts hydrogen chloride is given off. The excess acid Triothanolaminemono dipropionateu 0 halide is neutralized with alkali and the tri- Ol ve oil 20 ethanolamine tripropionate obtained 'by distilla- 40 tion in ood ields, havin a boilin oint 218- g y g g p wool, cellulose acetate, viscose, etc., as described 220 C./21 mm.
- in Example 1. If the yarn is intended primarily Preparation of triethanolamine diacetate monoknitting, the amount of conditioning q d 'o t applied may vary fromt 4-25% by weight of the yarn, and if the yarn is intended for weaving, A mixture of 150 parts triethanolamine, '75 the amount of liquid applied may vary between parts propionic acid, 125 parts acetic acid, 5 15% by weight of the yarn. Cellulose acetate parts concentrated sulphuric acid, and parts filaments or fibers treated as described are quite benzene is distilled so that the benzene is auto- 50 soft and pliable and give improved results in varimatically separated from the water and returned ous operations such as weaving, knitting, etc.
and'applied to textile materials such as silk,
to the reaction. Fifty-four parts of water are Other examples of yarn conditioning compocollected. The solution is then washed with disitions which may be applied to various types lute sodium carbonate solution and distilled. of yarn, particularly those composed of or con- Two hundred and eighty parts of the diacetyl, taining cellulose acetate, cellulose acetate promonopropionyl derivative of triethanolamine are pionate, cellulose acetate butyrate, and similar obtained, having a boiling point at 25 mm. of cellulose organic acid esters in accordance with 215-223 C. our invention and which render such yarns soft In accordance with the invention these com and pliable and especially well adapted for varipounds may be applied directly to the yarn durous textile operations, particularly knitting, are as ing or after spinning, or may be added to the follows:
spinning solution itself. We have found that i, 3
these compounds have exceptional solvent pow- Parts ers which enable them to dissolve mineral oils Triethanolamine tripmpionate 80 nd blown and unblown, drying and semi-drying, 5 Blown olive oil 20 vegetable and animal oils and accordingly they may be, and preferably'are, employed as ingre- EXAMPLE 4 dients of yarn conditioning or lubricating for- Parts mulas in conjunction agents which fllIiC- Tripropanolamine dipropionate monoacetate 20 tion wholly or partially as lubricants. Light mineral 11 30 In the following examples and description we have set forth several of the preferred embodi- EXAMPLE 5 ments of our invention, but they are included Parts merely for purposes of illustration and not as a Tributanol amine monovalerate 70 limitation thereof. Blown sperm nil 3o Ethyl di-y-hydroxy propylamino p-methoxy combination used in making up the spinning solution, and the degree of softness or pliability desired in the yarn, etc.
If the conditioning agent is to be applied to the yarn after spinning, this may be done by bringing the yarn in contact with a wick, roll,
or felt wet therewith, or the liquid may be applied by immersion, spray, or otherwise. The
particular point at which the liqui i applied may vary. 'It may, for example, be applied to the yarn inside or outside the spinning cabinet, between the guide and godet roll, between the godet or other roll or guide and the point of winding and/or twisting. In some cases, the liquid may even be applied to the yarn after winding onto cones, spools, bobbins, or the like or by'the so-called bobbin to bobbin method. In the case of staple fiber manufacture, the liquid may be applied to the yarn prior to, or after, cutting into staple lengths.
The amount of the agent so employed will 'vary widely depending upon the results desired,
the specific nature of the material to which the agent is applied, the use to which the yarn is acetate 20 Tetrahydrofurfuryl formate e 20 Blown soya bean oil 60 EXAMPLE 10 A 20% solution of cellulose acetate in acetone, in which is incorporated 1-25% by weight of the cellulose acetate of triethanolamine caproate, is extruded through fine orifices into an evaporative atmosphere. The filaments thus produced are wound or twisted and wound. Yarns thus produced are pliable and suitable for knitting.
, Triethanolamine monobutyratedipropionate Any of the above compositions may be applied to the yarn intended for use in circular knitting by means of a bath, wick, spray, roller, pad or any suitable means. The amount of conditioning liquid applied may vary between 525% by weight of the yarn. Usually, however, the amount of conditioning liquid applied is about 10-15% by weight of the yarn. Yarn composed of cellulose acetate conditioned as described above gives excellent results when used in the circular knitting process.
As will be apparent from the' above examples eventually to be put and other factors. For example, in a given case where a cellulose organic acid ester yarn such as a yarn composed of cellulose acetate, is intended for knitting, about 4 to 25% or more by weight, based on the weight of the dry yarn, may be satisfactory, while if the yarn is intended for weaving, the amount may vary between about 1 and 5%.
Although in the above examples we have referred primarily to yarn treating compositions containing only the conditioning agent and an oil, other ingredients such as solvents, non-solvents, emulsifying agents, blending and the like, may be added within the scope of our invention. Likewise, various dyes or other coloring matter may be included in case it is desired to permanently or fugitively tint or dye the material undergoing treatment.
Although we have found it convenient to illustrate our invention by reference to compositions containing specific percentages of the various inredients, these percentages may vary widely depending upon the particular purpose for which the composition is intended. For example, if it and description, the conditioning agents of our invention may be applied by a wide variety-of methods. For example, we may employ the agent as an ingredient of the Spinning dope from which the filaments are formed, the amount of the agent so employed depending upon a number of factors, such as the particular cellulos derivative used in making the yarn, the solvent or solvent is desired to control the solvent or softening action of the conditioning agent, the amount of the agent may be adjusted as, for example, by reducing the amount of the agent and correspondingly increasing the amount of oil or other ingredient.
While we have described our invention with particular reference to the treatment of yarns composed of organic derivatives of cellulose such as celluloseacetate, the conditioning agents and formulas described herein ar applicable to the conditioning of many other types of cellulose derivative yarns such as those composed of or containing cellulose propionate, cellulose butyrate, cellulose acetate propionate, cellulose acetate butyrate, ethyl cellulose, methyl cellulose, benzyl cellulose and others, as well as to the conditioning of silk, wool, cotton, viscose and other natural or artificial materials.
The term yam as used herein and in the claims is to be understood as including a single filament, a plurality of filaments associated into the form of thread, either of high or low twist single or multiple threads associated or twisted together, composite threads composed of a mixture of natural and artificial filaments or a compositethread formed by twisting together individual strands of natural or artificial materials, as well as cut staple fibers produced from natural and/or artificial filament or threads and spun yarn produced from such stable fibers.
As indicated above, the yarn conditionin agents of our invention are exceptionally good solvents for a wide variety of mineral, blown and unblown, drying and semi-drying animal and vegetable oils such as cottonseed, olive, castor, neat'sfoot, sperm and other oils. This enables them to be used with any of such oils in making up a variety of yarn treating formulas of varying composition. v
The yarn conditioning method and compositions of our invention possess many outstanding advantages. The fundamental and outstanding characteristic of the agents employed in accordance with the invention is their ability to soften yarns, especially those composed of or containing organic derivatives of cellulose such as cellulose acetate and render them soft and pliable and amenable to various textile operations, especially operations such as those involved in weaving and knitting where complicated designs or stitches are employed, without too drastic an action on the eating assistants in conjunction with these oils when applied to such yarns. In addition, due to their solubility in water, they may be readily removed from yarns and fabrics by means of the usual aqueous scour baths. By employing the yarn conditioning agents and method of our invention as herein described, one is enabled to obtain highly satisfactory results in the manufacture of yarns and woven fabrics and especially the production from these yarns of closely knit fabrics free from defects such as pin holes, stitch distortion, laddering and the like.
What we claim and desire to secure by Letters Patent of the United States is:
1. The process of conditioning yarn composed of or containing cellulose acetate to render it more amenable to textile operations including knitting, weaving, spinning, and the like which comprises applying thereto a lubricating and softening composition containing as its essential lubricating and softening component triethanolamine monoacetate dipropionate.
2. Textile yarns composed of or containing cellulose acetate amenable to textile operations including knitting, weaving, spinning, and the like, impregnated with a lubricant comprising triethanolamine mono-acetate dipropionate,
JOSEPH B. DICKEY. JAMES B. NORMINGTON.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US246201A US2333770A (en) | 1938-12-16 | 1938-12-16 | Conditioning cellulose acetate yarn |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US246201A US2333770A (en) | 1938-12-16 | 1938-12-16 | Conditioning cellulose acetate yarn |
Publications (1)
Publication Number | Publication Date |
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US2333770A true US2333770A (en) | 1943-11-09 |
Family
ID=22929691
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US246201A Expired - Lifetime US2333770A (en) | 1938-12-16 | 1938-12-16 | Conditioning cellulose acetate yarn |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2496631A (en) * | 1946-07-08 | 1950-02-07 | Nopco Chem Co | Wool treatment |
US2805992A (en) * | 1954-03-30 | 1957-09-10 | Celanese Corp | Textile conditioning agent |
US2925639A (en) * | 1953-11-30 | 1960-02-23 | Deering Milliken Res Corp | Method of fulling and scouring wool |
US3028402A (en) * | 1952-12-12 | 1962-04-03 | Ciba Ltd | High molecular nitrogen condensation products |
US3329517A (en) * | 1965-02-05 | 1967-07-04 | Grace W R & Co | Cement additives composed of ethanolamine salts |
US4368127A (en) * | 1979-07-02 | 1983-01-11 | Akzona Incorporated | Fabric softening compounds and method |
-
1938
- 1938-12-16 US US246201A patent/US2333770A/en not_active Expired - Lifetime
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2496631A (en) * | 1946-07-08 | 1950-02-07 | Nopco Chem Co | Wool treatment |
US3028402A (en) * | 1952-12-12 | 1962-04-03 | Ciba Ltd | High molecular nitrogen condensation products |
US2925639A (en) * | 1953-11-30 | 1960-02-23 | Deering Milliken Res Corp | Method of fulling and scouring wool |
US2805992A (en) * | 1954-03-30 | 1957-09-10 | Celanese Corp | Textile conditioning agent |
US3329517A (en) * | 1965-02-05 | 1967-07-04 | Grace W R & Co | Cement additives composed of ethanolamine salts |
US4368127A (en) * | 1979-07-02 | 1983-01-11 | Akzona Incorporated | Fabric softening compounds and method |
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