US2041692A - Textile process and product - Google Patents
Textile process and product Download PDFInfo
- Publication number
- US2041692A US2041692A US63173832A US2041692A US 2041692 A US2041692 A US 2041692A US 63173832 A US63173832 A US 63173832A US 2041692 A US2041692 A US 2041692A
- Authority
- US
- United States
- Prior art keywords
- yarn
- conditioning
- cellulose
- diether
- cellulose acetate
- 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
- 239000004753 textile Substances 0.000 title description 32
- 238000000034 method Methods 0.000 title description 22
- 230000003750 conditioning effect Effects 0.000 description 63
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- 239000000463 material Substances 0.000 description 32
- 229940081735 acetylcellulose Drugs 0.000 description 31
- 229920002301 cellulose acetate Polymers 0.000 description 31
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 29
- 229920002678 cellulose Polymers 0.000 description 27
- 239000001913 cellulose Substances 0.000 description 27
- 235000010980 cellulose Nutrition 0.000 description 27
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 23
- 239000003795 chemical substances by application Substances 0.000 description 23
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 21
- 239000003921 oil Substances 0.000 description 20
- 235000019198 oils Nutrition 0.000 description 20
- 150000002170 ethers Chemical class 0.000 description 19
- 239000004744 fabric Substances 0.000 description 14
- 239000007788 liquid Substances 0.000 description 14
- 238000009940 knitting Methods 0.000 description 13
- 239000004006 olive oil Substances 0.000 description 13
- 235000008390 olive oil Nutrition 0.000 description 13
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- 239000012530 fluid Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 229940093476 ethylene glycol Drugs 0.000 description 9
- 238000009833 condensation Methods 0.000 description 7
- 230000005494 condensation Effects 0.000 description 7
- 150000005846 sugar alcohols Polymers 0.000 description 7
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229930040373 Paraformaldehyde Natural products 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229920002866 paraformaldehyde Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- -1 aliphatic hydroxy compound Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 235000004879 dioscorea Nutrition 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000009941 weaving Methods 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000001143 conditioned effect Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000578 dry spinning Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 238000010409 ironing Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000009991 scouring Methods 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 239000002759 woven fabric Substances 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
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- KMZHZAAOEWVPSE-UHFFFAOYSA-N 2,3-dihydroxypropyl acetate Chemical compound CC(=O)OCC(O)CO KMZHZAAOEWVPSE-UHFFFAOYSA-N 0.000 description 1
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-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
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229920013683 Celanese Polymers 0.000 description 1
- 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 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
- 244000292411 Excoecaria agallocha Species 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 239000004348 Glyceryl diacetate Substances 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000009286 beneficial effect Effects 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 229920006218 cellulose propionate Polymers 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- PVRATXCXJDHJJN-UHFFFAOYSA-N dimethyl 2,3-dihydroxybutanedioate Chemical compound COC(=O)C(O)C(O)C(=O)OC PVRATXCXJDHJJN-UHFFFAOYSA-N 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 239000001761 ethyl methyl cellulose Substances 0.000 description 1
- 235000010944 ethyl methyl cellulose Nutrition 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 235000019443 glyceryl diacetate Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 230000037303 wrinkles Effects 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
- D06M13/10—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
- D06M13/137—Acetals, e.g. formals, or ketals
-
- 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
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2861—Coated or impregnated synthetic organic fiber fabric
- Y10T442/2869—Coated or impregnated regenerated cellulose fiber fabric
Definitions
- invention relates to the treatment of yarn and other textile materials and relates more particularly to the conditioning of yarn made of orsuch as knitting, where they are subjected to' benzaldehyde with an aliphatic hydroxy compound, for example, a polyhydric alcohol, a partial ether of a polyhydric alcohoLlor an aliphatic hydroxy carboxylic acid.
- an aliphatic hydroxy compound for example, a polyhydric alcohol, a partial ether of a polyhydric alcohoLlor an aliphatic hydroxy carboxylic acid.
- This type of ether is referred to hereinafter in the claims as a 1.3- diether.
- the resulting yarn 55 has highly increased flexibility, and knit fabrics yarn pliable to a certain degree, after a storage of close construction may be formed therefrom, which fabrics are substantially free from defects occurring in fabrics made from insufliciently conditioned yarn. Moreover upon storage of such treated yarn, the knitting and other properties of the same are not deleteriously affected, and in many cases are even improved after a period' of time. Other advantageousproperties are also imparted to the yarn as will appear below.
- incorl0 porate in textile materials comprising filaments of cellulose acetate or other organic derivatives of cellulose, a conditioning agent containing an ether of the type hereinbefore' defined that is a solvent or at least has a latent solvent action on the cellulose acetate or other organic derivative of cellulose.
- the yarns or other textile material made or treated in accordance with this invention may have finely divided pigment-like material, such as titanium dioxide, antimony trioxide, stannic oxide, starch, highly melting insoluble organic compounds and the like, incorporated -therein, whereby they have a subdued luster.
- the yarn to be treated need 'not consist wholly of yarns of cellulose acetate but may, also con- 40 tain fibres of other materials such as natural si lk, artificial, fibres of reconstituted cellulose, wool, cotton, etc.
- the yarns of cellulose acetate may be formed tram continuous filaments or the same may be spun from short staples or short lengths of such filaments; J
- the ethers of the present invention maybe made by the condensation of formaldehyde,
- the following is a method of preparing one of the ethers of the present invention.
- the following method of preparing the diether or the e-hydroxy-iso -butyric acid is illustrative of the method of preparing the diethers of hydro-2y earboxylic acids.
- the major portion of the distillate comes over at about C. and separates into two layers.
- the lower layer is dried and redistilled, the distillate being a product boiling at 148 to 149 C. and having the probable formula
- those ethers of the type hereinbeiore defined that are relatively non volatile having a boiling point above say C. and that are soluble in or miscible with water.
- relatively non-volatile diethers are preferred is that upon storage of the conditioned yarn such diethers do not tend to evaporate readily and therefore the treated yarns retain their pliability for a long period of time.
- the ethers of the type hereinbefore defined may be employed in conjunction with other relatively high boiling solvents or latent solvents for cellulose acetate, such as ethyl oxy butyrate, benzyl alcohol, diacetone alcohol, monacetin, diacetin, acetcl (acetyl carhinol) cyclohexanonacyclopentanone, dimethyl tartrate, etc.
- solvents or latent solvents for cellulose acetate such as ethyl oxy butyrate, benzyl alcohol, diacetone alcohol, monacetin, diacetin, acetcl (acetyl carhinol) cyclohexanonacyclopentanone, dimethyl tartrate, etc.
- the organic derivative of cellulose yam have thereon an oily lubricant to facilitate winding, twisting, knitting, weaving or other textile operations, it will be found advantageous to incorporate such oils in the conditioning liquid containing the ethers of the type hereinbeiore defined, unless the oily lubricant has already previously been applied to the textile material that is to be treated with the conditioning liquid.
- oily lubricant may be admixed with the ether of the present invention when applied to the textile material.
- the specific oils employed are not miscible with the specific ether or" the present invention used, they may generally be rendered miscible with each other and with any polyhydric' alcohol and/or water present, by the addition of a free fatty acid such as oleic acid or stearic acid.
- the oxidized oil may be preparedin any suitable manner, e. g. by injecting a fine stream of oxygen into a body of olive oil or more preferably by injecting olive oil in a fine.
- a hygroscopic relatively non volatile substance which may be incorporated in the conditioning liquid containing the ethers of the present invention or if such ethers of the present invention have previously been applied to the yarn, this hygroscopic substance may be applied subsequently either with or without the ethers of the present invention.
- hygroscopic substances are relatively non-volatile liquids having an aflinity for water such as diethylene glycol, glycerin, ethylene-glycol, propylene glycol or other polyhydric alcohols, the mono ethyl ether of ethylene-glycol and others ethers of glycols or other polyhydric alcohols.
- water such as diethylene glycol, glycerin, ethylene-glycol, propylene glycol or other polyhydric alcohols, the mono ethyl ether of ethylene-glycol and others ethers of glycols or other polyhydric alcohols.
- the amount of water present preferably being nation that forms a solution which upon exposure to air does not change appreciably in concentra-
- the amount of waterj may be from 20 to 50% of the hygroscopic liquid present.
- the ethers of the type hereinbefore defined may be incorporated in the textile material in anysuitable manner.
- they may be added to the spinning solution containing thecellulose acetate dissolved in a volatile solvent in amounts from 0.5 to 15% of the weight of the cellulose to be subjected to a knitting or analogous textile operation, the amount of conditioning liquid applied maybe from 3 to 15% of the weight of the yarn, the larger percentage being applied in 60 those cases wherethe conditioning fluid contains smaller percentages of the ether of the present invention. If the conditioning fluid is to be applied to the yarn which is to be woven, the amount of conditioning fluid applied may be only o5 ⁇ lto3%.
- the conditioning fluid may be applied to the yarn in any suitable manner. Thus it may be applied by the immersing of hanks of yarn ,to be treated in a bath containing the conditioning 79. fluid. If desired, the conditioning fluid may be applied to the yarn while it is in transit from package to package. This may be done by passing the yarn over pads or wicks that are impregnated with the conditioning fluid or by passing 7 over rollers or discs, the bottoms of which are immersed in the conditioning fluid. The conditioning fluid may be dripped onto the yarns while they are in transit, and also the yams may be caused to dip into a bath containing the conditioning fluid while they are in transit, prior to 5 being wound onto a suitable package. In another form, the conditioning fluid may.
- Cellulose acetate yarns treated in accordance 35 with this invention have many important advantages. As stated they are very pliable and flexible, and even after storage for a prolonged period of time, not only is this pliability or flexibility retainedbut in many instances is actually no improved. Therefore irrespective of the age of the treated yarns, they can be readily'rewound from their original package or subjected to any textile operation.
- Cellulose acetate yarn when treated by this invention may be knitted on certain circular knitting machines which are not capable of knitting untreated cellulose acetate yarn or cellulose acetate yarn finished by previous methods, to form a commercially satisfactory fabric and likewise may be netted successfully on lace-making machines to form highly satisfactory lace.
- yarn treated by this invention is exposed for ca several days to normal atmospheric conditions without any precautions whatever, the yarn still retains its good knitting properties.
- yarn treated by this invention maybe knitted atv a higher rate than yarn treated by previous methods. The yarn maybe processed regardless of humidity conditions and this renders the use of expensive humidifying apparatus unnecessary.
- a conditioning liquid is made as follows:
- This conditioning liquid may be applied by means of wicks, rollers, discs or other suitable furnishing devices to the cellulose acetate filaments immediately after leaving the dry spinning machine and prior to their being wound or twisted and wound, or it may be applied to the yarns during any subsequent textile operation. If the yarn is intended primarily for knitting purposes the-amount of conditioning liquid applied will be from 4 to 6% of the weight of the yarn. If the yarn is intended primarily for weaving the amount of conditioning liquid applied may be only 1 to 2% of the weight of the yarn and the conditioning liquid will contain a smaller proportion of the diether.
- Example II A conditioning liquid is made up as follows:
- Method of conditioning textile materials containing organic derivatives of cellulose comprising incorporating a conditioning agent com prising a 1.3 diether therein.
- Method of conditioning yarn containing organic derivatives of cellulose comprising applying thereto a conditioning agent comprising a relatively non-volatile 1.3 diether that has a softening action on the organic derivative of cellulose.
- Method of conditioning yarn containing cellulose acetate comprising applying thereto a conditioning agent comprising a relatively non-volatile 1.3 diether that has a. softening action on the cellulose acetate.
- Method of conditioning yarn containing organic derivatives of cellulose comprising applying thereto a conditioning agent comprising a relatively non volatile 1.3 diether of a. compound selected from the group consisting of polyhydric alcohols and their partial ethers.
- Method of conditioning yarn containing cel lulose acetate comprising applying thereto a conditioning agent comprising a relatively non-volatile 1.3 diether of a compound selected from the group consisting of polyhydric alcohols and their partial ethers.
- Method of conditioning yarn containing cellulose acetate comprising applying thereto a conditioning agent comprising the 1.3 diether of the formula (CHaOCHzCI-IzO) 2CH2.
- Method of conditioning yarn containing organic derivatives of cellulose comprising applying thereto a conditioning agent comprising a 1.3 diether and an oil.
- Method of conditioning yarn containing cellulose acetate comprising applying thereto a conditioning agent comprising a relatively non volatile 1.3 diether and an oxidized non drying oil.
- Method of conditioning yarn containing cellulose acetate comprising applying thereto a conditioning agent comprising 50 to 80 parts by weight of a relatively non volatile 1.3 diether and 50 to 20 parts by weight of an oil.
- Method of conditioning yarn containing cellulose acetate comprising applying thereto a conditioning agent comprising a relatively non 'vol-. atile 1.3 diether, an oil and a hygroscopic substance.
- Method of conditioning yarn containing cellulose acetate comprising applying thereto a conditioning agent comprising the 1.3-diether of the formula (CH3OCH2CH2O) 2CH2, oxidized olive oil, diethylene glycol and water.
- Textile materials comprising organic derivatives of cellulose having therein a conditioning agent comprising a 1.3 diether.
- Textile materials comprising cellulose aceiate having therein a conditioning agent comprising a relatively non volatile 1.3 diether.
- Yarn comprising organic derivatives of cellulose having applied thereto a conditioning agent comprising a relatively non volatile 1.3 diether and an oil.
- Method of conditioning yarn containing organic derivatives of cellulose which comprises I applying thereto a conditioning agent comprising a cyclic 1.3 diether and an oil.
- Textile material comprising organic deriva-- tives of cellulose having therein an ether formed by the condensation of formaldehyde with the mono methyl ether of ethylene glycol.
- Textile material comprising cellulose ace- 20 tate having therein an ether formed by the condensation of formaldehyde with the mono methyl ether of ethylene glycol.
- Textile material comprising cellulose acetate having therein an ether formed by the condensation of formaldehyde with the mono methyl ether of ethylene glycol, and an oxidized olive oil.
- Textile material comprising organic derivatives of cellulose having a 1.3-diether and oxidized olive oil therein.
- Textile material comprising cellulose acetate having a 1.3-diether and oxidized olive oil therein.
- Textile materials comprising ,organic derivatives of cellulose having a 1.3-diether and oxidized non-drying oils therein.
- Textile materials comprising cellulose acetate having a 1.3-diether and oxidized non-dryi oils therein.
Description
Patented May 26, 1936 I 2,041,692 v 'raxmn raocass am) rnonuc'r George R. Blake and Geor W. Seymour, Cumberland, Md., asslgnors to Celanese Corporation of America, a corporation of Delaware No Drawing. Application September 3, 1932,"
Serial N0. 631,738
29 Claims.
invention relates to the treatment of yarn and other textile materials and relates more particularly to the conditioning of yarn made of orsuch as knitting, where they are subjected to' benzaldehyde with an aliphatic hydroxy compound, for example, a polyhydric alcohol, a partial ether of a polyhydric alcohoLlor an aliphatic hydroxy carboxylic acid. This type of ether is referred to hereinafter in the claims as a 1.3- diether. Other objects of this invention will appear from the following detailed description.
The knitting of yarns made of organic derivatives of cellulose presents serious difiieulties, since if attempts are made to form a closely knit fabric from such yarns, on certain machines, such. as a Wildman circular knitting machine forming a straight stitch, serious defects or faults develop because of thela'ck of pliability of such yarns. In order to condition such yarns, animal orvegetable 011 such as olive oil, or mineral oils have been applied thereto. While olive oil renders such containing a formal that is a solvent or at least a latent solvent for the cellulose acetate or other organic derivative of cellulose, the resulting yarn 55 has highly increased flexibility, and knit fabrics yarn pliable to a certain degree, after a storage of close construction may be formed therefrom, which fabrics are substantially free from defects occurring in fabrics made from insufliciently conditioned yarn. Moreover upon storage of such treated yarn, the knitting and other properties of the same are not deleteriously affected, and in many cases are even improved after a period' of time. Other advantageousproperties are also imparted to the yarn as will appear below.
In accordance with our invention we incorl0 porate in textile materials comprising filaments of cellulose acetate or other organic derivatives of cellulose, a conditioning agent containing an ether of the type hereinbefore' defined that is a solvent or at least has a latent solvent action on the cellulose acetate or other organic derivative of cellulose.
The textile materials to be made or treated in accordance with our invention may be in the form of yarns containing a plurality of filaments made of cellulose acetate or other organic, derivatives of cellulose. Onthe other hand the textile materials may be in the form of films, artificial bristles or straw containing such cellulose acetate so as to make it possible to knot, bend or braid them more' easily. While we prefer to-treat textile materials containing cellulose acetate, suchtextile materials may contain other organic derivatives of cellulose such as cellulose formate, cellulose propionate, cellulose. butyr'ate, ethyl cellulose, methyl cellulose and benzyl. cellulose. If desired, the yarns or other textile material made or treated in accordance with this invention may have finely divided pigment-like material, such as titanium dioxide, antimony trioxide, stannic oxide, starch, highly melting insoluble organic compounds and the like, incorporated -therein, whereby they have a subdued luster. V I The yarn to be treated need 'not consist wholly of yarns of cellulose acetate but may, also con- 40 tain fibres of other materials such as natural si lk, artificial, fibres of reconstituted cellulose, wool, cotton, etc. The yarns of cellulose acetate may be formed tram continuous filaments or the same may be spun from short staples or short lengths of such filaments; J
r The ethers of the present invention maybe made by the condensation of formaldehyde,
formalin, trihydroxy-methylene or para formaldehyde in the presence or absence of an acidic catalyst with simple polyhydric alcohols, such as glycerol, ethylene glycol or propylene glycol, or substituted polyhydric alcohols such as glycerol mono chlorhydrln or diethylene glycol. Examples 55 5 glycol and the mono methyl or ethyl ether of,
propylene glycol'or of diethylene glycol. Examples of hydroxy carboxylic acids that may be used for preparing the others of the type above defined are a-hydroxy-iso-butyric acid, a-hy- 0 droxy normal butyric acid, glycollic acid, lactic acid, etc. Examples of acid catalysts that may be employed for promoting the condensation are ferric chloride or other acid salts, hydrochloric acid, sulfuric acid, phosphoric acid or other strong or weak mineral acids.
Representative examples of methods of maizing some of these ethers will be given merely by way of illustration, it being understood that this invention is of general application and is in no way limited to the specific mode of preparing the ethers employed therein.
The following is a method of preparing one of the ethers of the present invention.
Two molecular proportions of the monomethyl ether of ethylene glycol, CHaOCHzCHzOl-I, one (1) molecular proportion of para-formaldehyde and hydrated ferric chloride (in amount equal to 4% of the weight of the reactants) are subjected to slow distillation. The distillate is collected in three fractions, namely at temperatures from 92 to 110 C., from 110 to 180 C. and from 180 to 200- C. Calcium chloride is added to the first two fractions and the upper layers thereof are added to the third fraction and the mixture is '35 then redistilled. The fraction boiling" at 197 to 205 C. is collected, and this is an ether which is probably represented by the formula (CH3OCH2CH20) 20% Another ether of the present invention, the methylene ether of diethylene glycol, having the probable structural formula oi O CH:
may be formed by refluxing for 18 hours, 106
grams of diethylene glycol with 30 grams of paraformaldehyde in the presence of 5 cc. of concentrated HCl. The resulting material is fractionally distilledand the fraction boiling between 1% to 240 C. is separated.
Another ether ofthe type hereinbeiore defined which has the structural formulae of may be prepared, for instance, by refluxing equimolecular proportions of glycerol or polyglyceroi with formalin, tri-hydroxymethylene or para formaldehyde in the presence of hydrochloric acid (I-iCl) or other suitable catalyst.
The following method of preparing the diether or the e-hydroxy-iso -butyric acid is illustrative of the method of preparing the diethers of hydro-2y earboxylic acids.
Cine (1) molecular proportion of e-hydroiryiso-butyric acid is mixed with one (1) molecular proportion of paraformaldehyde and a very small amount of sulfuric acid as catalyst is added there- 5 to. The mixture is subjected w en distillation.
The major portion of the distillate comes over at about C. and separates into two layers. The lower layer is dried and redistilled, the distillate being a product boiling at 148 to 149 C. and having the probable formula Generally we prefer to employ those ethers of the type hereinbeiore defined that are relatively non volatile having a boiling point above say C. and that are soluble in or miscible with water. The reason that relatively non-volatile diethers are preferred is that upon storage of the conditioned yarn such diethers do not tend to evaporate readily and therefore the treated yarns retain their pliability for a long period of time. Since it is desirable that the diethers which are solvents or latent solvents be removed from the fabric after it is formed from the treated yarn, if they are water soluble they can be readily removed in the ordinary scouring and/or dyeing operations, and even exert a beneficial efiect in such operations.
If desired the ethers of the type hereinbefore defined may be employed in conjunction with other relatively high boiling solvents or latent solvents for cellulose acetate, such as ethyl oxy butyrate, benzyl alcohol, diacetone alcohol, monacetin, diacetin, acetcl (acetyl carhinol) cyclohexanonacyclopentanone, dimethyl tartrate, etc.
While one or more ethers of the type hereinbefore defined alone may be incorporated in or applied to the textile materials, generally it is preferable to apply the same in admixture with one or more other conditioning agents such as oily lubricants and relatively non-volatile materials having an aiilnity for water.
Since it is desirable that the organic derivative of cellulose yam have thereon an oily lubricant to facilitate winding, twisting, knitting, weaving or other textile operations, it will be found advantageous to incorporate such oils in the conditioning liquid containing the ethers of the type hereinbeiore defined, unless the oily lubricant has already previously been applied to the textile material that is to be treated with the conditioning liquid. Thus olive oil, castor. oil, soya bean oil, peanut oil, palm oil, cotton seed or other nondrying oils or other vegetable, animal or mineral .oils may be admixed with the ether of the present invention when applied to the textile material. If the specific oils employed are not miscible with the specific ether or" the present invention used, they may generally be rendered miscible with each other and with any polyhydric' alcohol and/or water present, by the addition of a free fatty acid such as oleic acid or stearic acid.
While olive oil, when applied to yarn, tends to oridize or harden with time, thus rendering diiii-v cult the rewinding, knitting or other manipulation of aged yarn, the presence of the ether of the present invention overcomes this cliificulty largely or entirely since the ether of the present inven- 'tion forms a solution with such oxidized products.
We have further found that if pro-oxidized vegetable oils such. as olive oil, castor oil or other so called non-drying oils are employed as lubricants, the difficulty of ageing of the ordinaryoiis is iargely overcome and moreover such oxidized oils have greater miscibility with the ether of the present invention, or a mixture of ether of the present inventioma polyhydrlc alcohol and water 40 tion.
than do the normal oils. The oxidized oil may be preparedin any suitable manner, e. g. by injecting a fine stream of oxygen into a body of olive oil or more preferably by injecting olive oil in a fine.
spray into a stream of oxygen until the required degree of oxidation has occurred.
As to the relative proportions .of ethersmf the present invention to olive or other oil employed,
ployed, while if the yarn is to be employed forweaving or similar purposes, the lower proportions of ethers of the present invention will be used.
If the yarn is to be knitted orsubjected to similar severe textile operations, we prefer to apply thereto a hygroscopic relatively non volatile substance, which may be incorporated in the conditioning liquid containing the ethers of the present invention or if such ethers of the present invention have previously been applied to the yarn, this hygroscopic substance may be applied subsequently either with or without the ethers of the present invention. Examples of such hygroscopic substances are relatively non-volatile liquids having an aflinity for water such as diethylene glycol, glycerin, ethylene-glycol, propylene glycol or other polyhydric alcohols, the mono ethyl ether of ethylene-glycol and others ethers of glycols or other polyhydric alcohols. Generally these will be applied in association with water, the amount of water present preferably being nation that forms a solution which upon exposure to air does not change appreciably in concentra- The amount of waterjmay be from 20 to 50% of the hygroscopic liquid present.
The ethers of the type hereinbefore defined may be incorporated in the textile material in anysuitable manner. Thus they may be added to the spinning solution containing thecellulose acetate dissolved in a volatile solvent in amounts from 0.5 to 15% of the weight of the cellulose to be subjected to a knitting or analogous textile operation, the amount of conditioning liquid applied maybe from 3 to 15% of the weight of the yarn, the larger percentage being applied in 60 those cases wherethe conditioning fluid contains smaller percentages of the ether of the present invention. If the conditioning fluid is to be applied to the yarn which is to be woven, the amount of conditioning fluid applied may be only o5\lto3%.
The conditioning fluid may be applied to the yarn in any suitable manner. Thus it may be applied by the immersing of hanks of yarn ,to be treated in a bath containing the conditioning 79. fluid. If desired, the conditioning fluid may be applied to the yarn while it is in transit from package to package. This may be done by passing the yarn over pads or wicks that are impregnated with the conditioning fluid or by passing 7 over rollers or discs, the bottoms of which are immersed in the conditioning fluid. The conditioning fluid may be dripped onto the yarns while they are in transit, and also the yams may be caused to dip into a bath containing the conditioning fluid while they are in transit, prior to 5 being wound onto a suitable package. In another form, the conditioning fluid may. be applied as a spray onto cones, bobbins, pirns or other packages while the same are being wound, so that the spray is being continuously applied 10 during the formation of the package.' If desired, the yarn may be treated at the spinning cabinet with the conditioning agent while it is being transmitted from the spinning cabinet in which it is spun from solutions of organic deriva- 15 tives of cellulose and prior to being wound and/or wound and twisted into yam.
The yarn treated in accordance with this invention is very pliable and flexible, and may be knitted, woven or subjected to any other suitable 2o textile operations, to form knitted or woven fabric, hosiery, or other articles.
After the fabric is formed, it is highly desirable that the ethers of the present invention be completely removed from the fabric by scouring or- 25 during dyeing or any other finishing operation. We have found that the ethers of the present invention which are solvents or latent solvents tend to lower the melting point or safe ironing point of the material when they are present, but so after they are removed by any suitable means, the resulting textile material has as high a melting point and safe ironing point as the untreated textile material.
Cellulose acetate yarns treated in accordance 35 with this invention have many important advantages. As stated they are very pliable and flexible, and even after storage for a prolonged period of time, not only is this pliability or flexibility retainedbut in many instances is actually no improved. Therefore irrespective of the age of the treated yarns, they can be readily'rewound from their original package or subjected to any textile operation.
This yarn'may be knitted on circular knitting 45 machines or on warp knitting machines to produce fabrics of many wales and courses per unit length, which fabrics are substantially free of pin holes, distortions, tension lines, rowiness, etc.,
and have a much better appearance than fabric made from untreated yarns. Cellulose acetate yarn when treated by this invention may be knitted on certain circular knitting machines which are not capable of knitting untreated cellulose acetate yarn or cellulose acetate yarn finished by previous methods, to form a commercially satisfactory fabric and likewise may be netted successfully on lace-making machines to form highly satisfactory lace. Moreover when yarn treated by this invention is exposed for ca several days to normal atmospheric conditions without any precautions whatever, the yarn still retains its good knitting properties. Furthermore, yarn treated by this invention maybe knitted atv a higher rate than yarn treated by previous methods. The yarn maybe processed regardless of humidity conditions and this renders the use of expensive humidifying apparatus unnecessary.
Yarns, treated by this invention or fabrics made therefrom dye more readily since the ether present permits the rapid wetting out andpenetra- 'tion of the fibres due to'their softened nature.
Moreover fabrics made of such yarn do not tend to develop wrinkles or creases when dyed, de-
lustered, scoured or subjected to other finishing treatments, a factor which is of great importance in the case of hosiery or other knitted wares and in the case of dyeing or delustering of woven fabrics on a winch or similar apparatus where the material is treated in folded form. Yarns or fabrics treated with or containing the ethers of .the present invention deluster more readily and evenly when subjected to hot aqueous media such Example I A conditioning liquid is made as follows:
Parts by weight The ether formed by the condensation of formaldehyde with the mono methyl ether of ethylene glycol 60 to 70 Oxidized olive oil 40 to 30 A mixture of 70% diethylene glycol and 30% of water 6 to 12 This conditioning liquid may be applied by means of wicks, rollers, discs or other suitable furnishing devices to the cellulose acetate filaments immediately after leaving the dry spinning machine and prior to their being wound or twisted and wound, or it may be applied to the yarns during any subsequent textile operation. If the yarn is intended primarily for knitting purposes the-amount of conditioning liquid applied will be from 4 to 6% of the weight of the yarn. If the yarn is intended primarily for weaving the amount of conditioning liquid applied may be only 1 to 2% of the weight of the yarn and the conditioning liquid will contain a smaller proportion of the diether.
Example II A conditioning liquid is made up as follows:
Parts by weight The ether formed by the condensation of formaldehyde with the mono methyl ether of ethylene glycol '70 I Ordinaryolive oil 30 This conditioning liquid may be applied to the cellulose acetate filaments immediately after their leaving the dry spinning cell in which they are formed and prior to their being twisted and Wound. If the yarn is to be used for weaving the amount of conditioning liquid applied may be 1 to 2% of the weight of the yarn.
It is to be understood that the foregoing detailed description is given merely by way of illustration and that many variations may be made therein without departing from the spirit of our invention.
Having described our invention what we claim and desire to secure by Letters Patent is:
1. Method of conditioning textile materials containing organic derivatives of cellulose comprising incorporating a conditioning agent com prising a 1.3 diether therein.
aoageea 2. Method of conditioning textile materials containing cellulose acetate comprising incorporating a conditioning agent comprising a. 1.3 diether therein.
3. Method of conditioning yarn containing organic derivatives of cellulose comprising applying thereto a conditioning agent comprising a relatively non-volatile 1.3 diether that has a softening action on the organic derivative of cellulose.
4. Method of conditioning yarn containing cellulose acetate comprising applying thereto a conditioning agent comprising a relatively non-volatile 1.3 diether that has a. softening action on the cellulose acetate.
5. Method of conditioning yarn containing organic derivatives of cellulose comprising applying thereto a conditioning agent comprising a relatively non volatile 1.3 diether of a. compound selected from the group consisting of polyhydric alcohols and their partial ethers.
6. Method of conditioning yarn containing cel lulose acetate comprising applying thereto a conditioning agent comprising a relatively non-volatile 1.3 diether of a compound selected from the group consisting of polyhydric alcohols and their partial ethers.
7. Method of conditioning yarn containing cellulose acetate comprising applying thereto a conditioning agent comprising the 1.3 diether of the formula (CHaOCHzCI-IzO) 2CH2.
8. Method of conditioning yarn containing organic derivatives of cellulose comprising applying thereto a conditioning agent comprising a 1.3 diether and an oil.
9. Method of conditioning yarn containing cellulose acetate comprising applying thereto a conditioning agent comprising a relatively non volatile 1.3 diether and an oxidized non drying oil.
10. Method of conditioning yarn containing cellulose acetate'comprising applying thereto a conditioning agent comprising a relatively non volatile 1.3 diether and oxidized olive oil.
11. Method of conditioning yarn containing cellulose acetate comprising applying thereto a conditioning agent comprising 50 to 80 parts by weight of a relatively non volatile 1.3 diether and 50 to 20 parts by weight of an oil. I
12. Method of conditioning yarn containing cellulose acetate comprising applying thereto a conditioning agent comprising a relatively non 'vol-. atile 1.3 diether, an oil and a hygroscopic substance.
13. Method of conditioning yarn containing cellulose acetate comprising applying thereto a conditioning agent comprising the 1.3-diether of the formula (CH3OCH2CH2O) 2CH2, oxidized olive oil, diethylene glycol and water.
14. Textile materials comprising organic derivatives of cellulose having therein a conditioning agent comprising a 1.3 diether.
15. Textile materials comprising cellulose aceiate having therein a conditioning agent comprising a relatively non volatile 1.3 diether.
16. Yarn comprising organic derivatives of cellulose having applied thereto a conditioning agent comprising a relatively non volatile 1.3 diether and an oil. a
17. Yarn comprising cellulose acetate having applied thereto a conditioning agent comprising 19. Method of conditioning ya rn containing cellulose acetate which comprises incorporating therein av conditioning agent comprising a cyclic 1.3 diether.
20. Method of conditioning yarn containing organic derivatives of cellulose which comprises I applying thereto a conditioning agent comprising a cyclic 1.3 diether and an oil.
21. Textile materials containing organic derivatives of cellulose having therein a conditioning agent comprising a cyclic 1.3 diether.
22. Textile materials containing cellulose acetate having therein a conditioning agentcomprising a cyclic 1.3 diether.
23. Textile material comprising organic deriva-- tives of cellulose having therein an ether formed by the condensation of formaldehyde with the mono methyl ether of ethylene glycol.
24. Textile material comprising cellulose ace- 20 tate having therein an ether formed by the condensation of formaldehyde with the mono methyl ether of ethylene glycol.
25. Textile material comprising cellulose acetate having therein an ether formed by the condensation of formaldehyde with the mono methyl ether of ethylene glycol, and an oxidized olive oil.
26. Textile material comprising organic derivatives of cellulose having a 1.3-diether and oxidized olive oil therein. v
27. Textile material comprising cellulose acetate having a 1.3-diether and oxidized olive oil therein.
28. Textile materials comprising ,organic derivatives of cellulose having a 1.3-diether and oxidized non-drying oils therein.
29. Textile materials comprising cellulose acetate having a 1.3-diether and oxidized non-dryi oils therein.
GEORGE R. ,BLAKE. GEORGE W. SEYMOUR.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US63173832 US2041692A (en) | 1932-09-03 | 1932-09-03 | Textile process and product |
GB2453333A GB425044A (en) | 1932-09-03 | 1933-09-04 | Improvements in the manufacture of artificial textile materials |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US63173832 US2041692A (en) | 1932-09-03 | 1932-09-03 | Textile process and product |
Publications (1)
Publication Number | Publication Date |
---|---|
US2041692A true US2041692A (en) | 1936-05-26 |
Family
ID=24532531
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US63173832 Expired - Lifetime US2041692A (en) | 1932-09-03 | 1932-09-03 | Textile process and product |
Country Status (2)
Country | Link |
---|---|
US (1) | US2041692A (en) |
GB (1) | GB425044A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2987409A (en) * | 1959-04-29 | 1961-06-06 | Eastman Kodak Co | Film forming compositions |
-
1932
- 1932-09-03 US US63173832 patent/US2041692A/en not_active Expired - Lifetime
-
1933
- 1933-09-04 GB GB2453333A patent/GB425044A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2987409A (en) * | 1959-04-29 | 1961-06-06 | Eastman Kodak Co | Film forming compositions |
Also Published As
Publication number | Publication date |
---|---|
GB425044A (en) | 1935-03-04 |
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