US2279501A - Yarn conditioning process and compositions therefor - Google Patents
Yarn conditioning process and compositions therefor Download PDFInfo
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- US2279501A US2279501A US360450A US36045040A US2279501A US 2279501 A US2279501 A US 2279501A US 360450 A US360450 A US 360450A US 36045040 A US36045040 A US 36045040A US 2279501 A US2279501 A US 2279501A
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- Prior art keywords
- alpha
- hydroxy
- yarn
- cellulose
- yarns
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- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title description 28
- 230000003750 conditioning effect Effects 0.000 title description 16
- 238000000034 method Methods 0.000 title description 16
- 229920002678 cellulose Polymers 0.000 description 28
- 239000001913 cellulose Substances 0.000 description 27
- 239000000835 fiber Substances 0.000 description 24
- 229910052739 hydrogen Inorganic materials 0.000 description 23
- 239000001257 hydrogen Substances 0.000 description 23
- 230000003068 static effect Effects 0.000 description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 22
- 125000001424 substituent group Chemical group 0.000 description 22
- 230000005611 electricity Effects 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 17
- 125000003118 aryl group Chemical group 0.000 description 17
- 125000000753 cycloalkyl group Chemical group 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- -1 phenyl hexane-al Chemical compound 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- 229920002301 cellulose acetate Polymers 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
- 239000004753 textile Substances 0.000 description 9
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 8
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- 238000009987 spinning Methods 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 238000009940 knitting Methods 0.000 description 6
- 230000035508 accumulation Effects 0.000 description 5
- 238000009825 accumulation Methods 0.000 description 5
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 210000002268 wool Anatomy 0.000 description 5
- 239000000975 dye Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 238000009941 weaving Methods 0.000 description 4
- 238000004804 winding Methods 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 235000008390 olive oil Nutrition 0.000 description 3
- 239000004006 olive oil Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- QSPIDNGNCPIYGZ-UHFFFAOYSA-N (1-hydroxy-1-phenylpentyl)phosphonic acid Chemical compound C1(=CC=CC=C1)C(CCCC)(P(O)(=O)O)O QSPIDNGNCPIYGZ-UHFFFAOYSA-N 0.000 description 2
- 229920008347 Cellulose acetate propionate Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 240000007817 Olea europaea Species 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 239000010775 animal oil Substances 0.000 description 2
- 239000012237 artificial material Substances 0.000 description 2
- 239000010495 camellia oil Substances 0.000 description 2
- 238000009960 carding Methods 0.000 description 2
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 235000004879 dioscorea Nutrition 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 230000001050 lubricating effect Effects 0.000 description 2
- 239000010697 neat foot oil Substances 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil 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
- QMMJWQMCMRUYTG-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl QMMJWQMCMRUYTG-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- QJSFUOBKBXVTMN-UHFFFAOYSA-N C=C.P(O)(O)=O Chemical group C=C.P(O)(O)=O QJSFUOBKBXVTMN-UHFFFAOYSA-N 0.000 description 1
- JPIGCDFPBFXYHR-UHFFFAOYSA-N CC(=O)C.C(C)(=O)O.OCC(O)CO Chemical compound CC(=O)C.C(C)(=O)O.OCC(O)CO JPIGCDFPBFXYHR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 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
- NDJKXXJCMXVBJW-UHFFFAOYSA-N Heptadecane Natural products CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000000987 azo dye Substances 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
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229920001727 cellulose butyrate Polymers 0.000 description 1
- 229920006218 cellulose propionate Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000001804 emulsifying effect Effects 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
- GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- NIOYUNMRJMEDGI-UHFFFAOYSA-N hexadecanal Chemical compound CCCCCCCCCCCCCCCC=O NIOYUNMRJMEDGI-UHFFFAOYSA-N 0.000 description 1
- GQZXNSPRSGFJLY-UHFFFAOYSA-N hydroxyphosphanone Chemical compound OP=O GQZXNSPRSGFJLY-UHFFFAOYSA-N 0.000 description 1
- 229940046817 hypophosphorus acid Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-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
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- CIXSDMKDSYXUMJ-UHFFFAOYSA-N n,n-diethylcyclohexanamine Chemical compound CCN(CC)C1CCCCC1 CIXSDMKDSYXUMJ-UHFFFAOYSA-N 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Substances C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent 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
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
- D06M13/285—Phosphines; Phosphine oxides; Phosphine sulfides; Phosphinic or phosphinous acids or derivatives thereof
-
- 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
-
- 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 treatment of cellulose organic derivative filaments, fibers, threads and the like and more particularly to a method of eliminr ing the tendency of such materials to accumulate charges of static electricity in twisting, winding and spinning.
- the invention also relates particularly to the treatment of cellulose organic derivative cut staple fibers to adapt them for the manufacture of spun yarns.
- cellulose organic derivative materials particularly in filament, yarn, or sheet form. are particularly subject to the accumulation on their surfaces of charges of static electricity from frictional and other influences.
- the problem of static often assumes serious proportions.
- numerous steps in which the yarn is subjected to frictional influences may be necessary, as for example, twisting, winding, warping, carding, combing,
- This invention has as its principal object to provide an improved method for the treatment of cellulose organic derivative yarns to reduce or eliminate the tendency of such yarns to accumulate charges of electricity under frictional and other influences.
- a further object is to provide a method of facilitating the handling and employment of cellulose organic derivative cut staple fibers in the various operations involved in the manufacture of spun yams.
- a still further object is to provide a method of treating cellulose organic derivative yarns in either filament or cut staple form, wherein the material is simultaneously softened and lubricated and the accumulation of static charges thereon is prevented.
- Another object is to provide an improved type of cellulose organic derivative cut staple having little or no tendency toward accumulation of static electrical charges.
- R Ra ns s p cg... .0 OZ OH OH wherein R is an aromatic group; R and R are substituents selected from the group consisting of hydrogen, alkyl, aryl and heterocyclic groups including cycloalkyl, wherein R is a substituent selected from the group consisting of hydrogen, alkyl, cycloalkyl; Z is a substituent selected from the group consisting of hydrogen and salt-forming radicals, and wherein R and R may be part of a cyclic system of carbon atoms.
- the alkyl group may be methyl, ethyl, butyl, amyl, cetyl, alkoxyalkyl, allyl, methallyl and cycloalkyl, etc.
- the aromatic may be phenyl, naphthyl, tetrahydronaphthyl, furyl, zenyl and. the like.
- salts we may prepare are the sodium, potassium, calcium, magnesium, ammonium, mono-, di-, and trlethanolamine, diethyl-cyclohexylamine, cyclohexylamine, furiurylamine, diiuri'urylamine', ditetrahydroiurrurylamine, amylamine, dibutylamine, di-betamethoxyethylamine, trimethylbenzyl ammonium hydroxide etc.
- Example 2 134 g. phenyl ethyl ketone are heated at 60-150" with I 66 g. hypophosphorus acid for 1 day or more and then with 200 g. hexadecanealdehyde for an additional 12 hours.
- the reaction product has the formula:
- the nitro group may be reduced, diazotized and coupled to give water-soluble azo dyes.
- Example 3 0 H-triethanolamine salt (Bis-phenyioleyl hydroxy methanleigihosphonlc acid trietbanolamine is applied to textile materials (silk, wool, viscose, cellulose acetate, wool) by means of a wick, bath, roller, spray, etc., to facilitate their knitting, weaving, spinning and the like. Yarns lubricating with the above types of lubricants are of special value in the preparation of cut staple fibers. These fibers may be oiled before or after. cutting.
- Conditioning liquids particularly useful for the treatment of various types of yarns in accordance with our invention particularly those composed of or containing cellulose acetate, cellulose acetate propionate, cellulose acetate butyrate, and similar organic acid esters, and especially adapted for the deelectriflcation or anti-static treatment of cellulose organic derivative cut staple yarns are as follows:
- Example 7 1-10 parts H(IJ(I'
- Example 14 38-20 parts teaseed oil -70 parts glycerol acetone acetate 14 parts CH: v I: Qt)l-fi-OH-diethylcyclohexylamine salt I COOH ll!
- 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 amounts of conditioning liquid applied may vary between 5-25% by weight of the yarn. Usually, however, the amount of conditioning liquid applied is about 1015% by weight of the yarn.
- Yarn composed of cellulose acetate conditioned as described above gives excellent results when used in the circular knitting process.
- conditioning agents of our invention may be applied by a wide variety of methods.
- 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 ielt wet therewith, or the liquid may be applied by immersion, spray, or otherwise.
- the particular point at which the liquid is 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.
- the liquid may even be applied to the yarn after winding onto cones, spools, bobbins, or-the like or by the socalled "bobbin to bobbin" method.
- 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 eventually to be put and other factors.
- 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 it the yarn is intended for weaving, the amount may vary between about 1 and 5%.
- compositions containing specific percentages of the various ingredients may vary widely depending upon the particular purpose for which the composition is intended. For example, if it is desired to control the deelectrifying 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 are 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 a thread, either of high or low twist, single or multiple threads associated or twisted together, composite threads composed of a mix ture of natural and artificial filaments or a composite thread formed by twisting together individual strands of natural or artificial materials. as well as cut staple fibers produced from natural and/or artificial filaments or threads and spun yarn produced from such staple fibers.
- the yarn conditioning 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, neats-foot, 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 agents of our invention also have exceptional value as surface active compounds and as such may be employed as wetting agents, emulsifying and dispersing agents, textile assistants, dye dispersing agents and the like.
- 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 abilityto deelectrify yarns, especially those composed of or containing organic derivatives of cellulose such as cellulose acetate and render them amenable to various textile operations, especially operations such as those involved in the manufacture of cut staple fibers, as well as in weaving and knitting.
- Another outstanding characteristic of these compounds is their exceptional solvent power for a wide variety of mineral, animal, and vegetable oils and their ability to act as lubricating 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.
- R is an aromatic group
- R and R are substituents selected fr m the group consisting of hydrogen, alkyl, cycloalkyl, aryl and heterocyclic groups, wherein R, is a substituent selected from the group consisting of hydrogen, alkyl, cycloalkyl
- Z is a substituent selected from the group consisting of hydrogen and salt-forming radica s.
- R is an aromatic group
- R and R. are substituents selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl and heterocyclic groups, wherein R is a substitute selected from the group consisting of hydrogen, alkyl,
- the method of eliminating the tendency of yarns, filaments or fibers composed of or containing organic derivatives of cellulose to accumulate charges of static electricity comprises applying thereto a composition containing as its essential anti-static component bisalpha-phenyl-alpha-hydroxy-decane phosphonic acid dimethyl cyclohexylamine salt.
- the method yarns, filaments taining organic mulate charges of eliminating the tendency of or fibers composed of or conderivatives of cellulose to accuof static electricity, which comprises applying thereto a composition containing as its essential anti-static component bis-alphaphenyl-alpha-hydroxy phenyl heptane phosphonic acid.
- An anti-static composition adapted, when applied to textile yarns, filaments or fibers to eliminate the tendency of such materials to accumulate charges of static electricity, said composition containing as its essential anti-static component a hydroxy] alkyl aryl phosphonate having the general formula:
- R is an aromatic group
- R and R are substituents selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl and heterocyclic groups, wherein 1'1.
- Z is a substituent selected from the group consisting of hydrogen and salt-forming radicals.
- An anti-static composition adapted, when applied to cellulose organic derivative yarns, filaments or fibers, to eliminate the tendency of such materials to accumulate charges of static electricity, said composition containing as its essential anti-static component a ,hydroxy alkyl aryl phosphonate having the general formula:
- composition containing as its'essential antistatic component a hydroxy alkyl aryl phosphonate having the general formula:
- R is an aromatic group
- R and R are substituents selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl and heterocyclic groups, wherein R is a substituent selected from the group consisting of hydrogen, alkyl, cycloalkyl;
- Z is a substituent selected from the group consisting of hydrogen and salt-forming radicals.
- An anti-static composition adapted, when applied to cellulose organic derivative yarns, filaments or fibers to eliminate the tendency of such materials to accumulate charges of static electricity, said composition containing as its essential anti-static component bis-alpha-(metasulfo) phenyl-alpha-hydroxy pentane-alphaphosphonic acid.
- An anti-static composition adapted, when applied to cellulose organic derivative yarns, filaments or fibers, to eliminate the tendency of such materials to accumulate charges of static electricity, said composition containing as its essential anti-static component bis-alpha-phenylalpha-hydroxy-decane-phosphonic acid dimethyl cyclohexylamine salt.
- An anti-static composition adapted, when applied to cellulose organic derivative yarns, filaments or fibers, to eliminate the tendency of such materials to accumulate charges of static electricity, said composition containing as its essential anti-static component bis-alpha-phenylal-pha-hydroxy phenyl heptane phosphonic acid.
- R is an aromatic group
- R and R are substituents selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl and heterocyclic groups, wherein R is a substituent selected from the group consisting of hydrogen, alkyl, cycloalkyl
- Z is a substituent selected from the group consisting of hydrogen and salt-forming radicals.
- Textile yarns composed of or containing organic derivatives of cellulose having a lessened tendency to accumulate charges of static electricity, said yarns containing a hydroxy alkyl aryl phosphonate having the general formula:
- R is an aromatic group
- R and R are substituents selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl and heterocyclic groups, wherein R is a substituent selected from the group consisting of hydrogen, alkyl, cycloalkyl
- Z is a substituent selected from the group consisting of hydrogen and salt-forming radicals.
- R is an aromatic group
- R and R are substituents selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl and heterocyclic groups, wherein R is a substituent selected from the group consisting of hydrogen, alkyl, cycloalkyl
- Z is a substituent selected from the group consisting of hydrogen and salt-forming radicals.
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Description
Patented Apr. 14, 1942 YARN CONDITI NING PROCESS AND COMPOSIT ONS THEREFOR Joseph B. Dickey and James G. McNally, Rochester, N. Y., assignors to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey No Drawing. Application October 9, 1940,
Serial No. 360,450
18 Claims.
This invention relates to the treatment of cellulose organic derivative filaments, fibers, threads and the like and more particularly to a method of eliminr ing the tendency of such materials to accumulate charges of static electricity in twisting, winding and spinning. The invention also relates particularly to the treatment of cellulose organic derivative cut staple fibers to adapt them for the manufacture of spun yarns.
As is well known, cellulose organic derivative materials, particularly in filament, yarn, or sheet form. are particularly subject to the accumulation on their surfaces of charges of static electricity from frictional and other influences. In the case of filaments and yarns in which the surface area of the material (per unit of weight) is enormously greater as compared to sheets or films, the problem of static often assumes serious proportions. In the manufacture ofiyarns of various types from artificial filaments, numerous steps in which the yarn is subjected to frictional influences may be necessary, as for example, twisting, winding, warping, carding, combing,
drawing, spinning and the like, all of which operations tend to produce large accumulations of static on the filaments. This is particularly aggravated in the utilization of cut staple, as for example, in the making of spun yarn, since in carding and combing considerable friction is de- Cellulose derivative yarn, particularly in the a form of cut staple, is extremely diiiicult to handle in the various operations involved in making spun yarn, not only because such material is composed of filaments having smooth, glass-like surfaces without natural kink 0r irregularity, but also because it has relatively negligible moisture content at normal humidities, as compared to natural fibers such as cotton and wool, making it inherently far more susceptible to the accumu lation of static. The charges accumulating on cellulose derivative cut staple fibers are, under some circumstances, even sufiicient to separate the individual fibers a distance of inches, notwi.hstanding their relatively minute size.
This invention has as its principal object to provide an improved method for the treatment of cellulose organic derivative yarns to reduce or eliminate the tendency of such yarns to accumulate charges of electricity under frictional and other influences.
A further object is to provide a method of facilitating the handling and employment of cellulose organic derivative cut staple fibers in the various operations involved in the manufacture of spun yams. A still further object is to provide a method of treating cellulose organic derivative yarns in either filament or cut staple form, wherein the material is simultaneously softened and lubricated and the accumulation of static charges thereon is prevented. Another object is to provide an improved type of cellulose organic derivative cut staple having little or no tendency toward accumulation of static electrical charges. Other objects will appear hereinafter.
These objects are accomplished by the following invention which in its broader aspects comprises applying to cellulose organic derivative yarns either in the form of filaments, threads or staple fibers, an antistatic composition containing as its essential anti-static component a hydroxy alkyl aryl phosphonate having the general formula:
R Ra ns s p cg... .0 OZ OH OH wherein R is an aromatic group; R and R are substituents selected from the group consisting of hydrogen, alkyl, aryl and heterocyclic groups including cycloalkyl, wherein R is a substituent selected from the group consisting of hydrogen, alkyl, cycloalkyl; Z is a substituent selected from the group consisting of hydrogen and salt-forming radicals, and wherein R and R may be part of a cyclic system of carbon atoms. Of the above group the alkyl group may be methyl, ethyl, butyl, amyl, cetyl, alkoxyalkyl, allyl, methallyl and cycloalkyl, etc., and the aromatic may be phenyl, naphthyl, tetrahydronaphthyl, furyl, zenyl and. the like.
These compounds may be prepared as described in Compt. rend., 134, 847; Ann. chim. phys., 8 3, 347; Compt. rend. 133, 219; Compt. rend., 136, 234.
PREPARATION or COMPOUNDS Example 1 0 OH CH:
(Bis-alpha-hydroxy-alpha-phegyl ethane-beta-phosphonic aci 2 There is also formed in) P n on 0 c=crr which is easily oxidized with air to give H EH (Bis-liydroxy phenyl-iuryl-mcthans pbosphonic acid) The salts are prepared by neutralizing the acid with the desired base. Some of the salts we may prepare are the sodium, potassium, calcium, magnesium, ammonium, mono-, di-, and trlethanolamine, diethyl-cyclohexylamine, cyclohexylamine, furiurylamine, diiuri'urylamine', ditetrahydroiurrurylamine, amylamine, dibutylamine, di-betamethoxyethylamine, trimethylbenzyl ammonium hydroxide etc.
Example 2 134 g. phenyl ethyl ketone are heated at 60-150" with I 66 g. hypophosphorus acid for 1 day or more and then with 200 g. hexadecanealdehyde for an additional 12 hours. The reaction product has the formula:
slim-m1 lli-hdr ess" papaaca ss Y Salts of the type mentioned in Example 1 are prepared.
Using the methods illustrated above we have prepared:
(Alpba-(l-naphthyl-5 sulfonic acid)-alpha-hydroxy butane-alpha hydroxy-alpba-methyl octadecam-beta-phosphonic acid) our CuHn sHu OH SOaH (Bis-alpha-hydroxy-alpha-(paracetyl-meta;siilfo)phenyl hexane-al pha-phosphomc acid) on I CtHn H 5 fi\ N 5H 0 0H CH:
(Meta-nitro-phenyl hydroxy methane lgeta-bydroxy-heptane-betaphospbonic acid) The nitro group may be reduced, diazotized and coupled to give water-soluble azo dyes.
(Al ha-hydrox'y-alpha-phenyl decane-alpha-hydroxy, cycle-hexanep alpha-phospbonic acid) OH O -V 5 all lls; OII
(Bis(para-sulio)pbenyl-liydroxy octadecylmcthane phosphouic acid) (Bis-alpha-hydroxy-alpha-naphthggyl ethanc-alpha-pliospbonic aci Any of the above compounds may be reacted with acid anhydrides to give ester of the -OH groups I In accordance with our invention the abovementioned phosphonate salts may be applied to the yarn in any convenient manner, for example, by roll, wick, immersion, spraying or the like. Inasmuch as these compounds'are soluble in oil they may be dissolved or dispersed in oils such 1 limitation thereof.
Example 3 0 H-triethanolamine salt (Bis-phenyioleyl hydroxy methanleigihosphonlc acid trietbanolamine is applied to textile materials (silk, wool, viscose, cellulose acetate, wool) by means of a wick, bath, roller, spray, etc., to facilitate their knitting, weaving, spinning and the like. Yarns lubricating with the above types of lubricants are of special value in the preparation of cut staple fibers. These fibers may be oiled before or after. cutting.
' Example 4 A conditioning liquid is made up as follows: -95 parts butyl naphthenate O=PO H-dicthylcycloliexylaniiue salt (bis-hydroxy phenyl cyclohexyl methane phosphonic acid diethylcyclohexylamine salt) and applied to textile materials such as silk, wool, cotton, viscose, cellulose acetate, etc., as described in Example 3. It the yarn is intended primarily for knitting, the amount of conditioning liquid applied may vary from 2-25% by weight or the yarn and it for weaving between 1-5% by weight. Conditioning liquids particularly useful for the treatment of various types of yarns in accordance with our invention particularly those composed of or containing cellulose acetate, cellulose acetate propionate, cellulose acetate butyrate, and similar organic acid esters, and especially adapted for the deelectriflcation or anti-static treatment of cellulose organic derivative cut staple yarns are as follows:
(Alpha-5,8-dihydroxy naphthyl-alpha-hydroxy hexadecyl-alphpstearyl-aipba-hydroxy-alpha-luryl methane phosphomc 801d. tributylamine salt) 99-80 parts blown olive 011 Example 8 10 parts butyl stearate 89-80 parts mineral oil 1-10 parts 55 O C O OH: (H) Curb-Qt? PO H-oleylamine' :11 elm-O naphthenylamine 2 Bisara-cetyl meta aulfophenyl alpha-acetoxy-gammaphgifiyl pfgpane phosphonic acid oleylamlne naphthenylam e sa 1 Example 9 1-10 parts (Alpha-o-hexylphenyletheralpha-hydroxy cyclohexane phosphonic acid morpholine salt) 99-90 parts neats-foot oil Example 10 .1-10 parts Ha OH-trlethylamine salt (Alpha-2-amino-Irhydroxy-al ha-hydroxy ethane-beta-hydroxy heptane phospho acid triethylamine salt) 99-90 parts blown neats-i'oot oil Example 11 55 parts sperm oil parts butyl naphthenate 20 parts mineral oil 5 parts OH H I CH: t P c ()H 0 CuHfl OH-di-beta-methoxyethylamine salt (Para-nitro henyl hydroxy methane-heta-hydroxy heptadecane p osphomc add di-beta-methoxy ethylamine salt) Example 12 68 parts blown sperm oil 10 parts l 0H-tetraethylammonium hydroxide salt (Bis-alpha-phenyl-aipha-oleyioxy ethane phosphonic acid tetralammoninm hydroxide salt) 2 parts water a I 20 parts di-beta-methoxyethyl succinate Example 13 1-10 parts cm on g. ]'P-0H-ethylenediamine salt 31g:
Example 7 1-10 parts H(IJ(I'|3H (|)H [H\ /C-C ]fi-OH-amylamine salt h 1 (Bis alpha furyl alphg hggl gg e fime phosphomc ac d 99-90 parts mineral oil so (Bis-alpha-(beta-tetralin) phosphonic acid ethylene diamine salt) 99-90 parts teaseed oil Example 14 38-20 parts teaseed oil -70 parts glycerol acetone acetate 14 parts CH: v I: Qt)l-fi-OH-diethylcyclohexylamine salt I COOH ll! 0 (l3is-alpha-meta-carboxcyy 3283x331 me sa igosphonic acid diethrl- 1-5 parts CHr- C|lHll ONa 0= ONa (Beta-methyl heptane-beta-phosphonic acid disodium salt) Example 15 1-10 parts on Ole-cm.
lH-dimetbylcyclohexylamlne salt Bis-a1 ha-phenyl-alpba-hydroxy decane phoephonic acid dimethyl p cyclohexylamine salt) 30-40 parts blown olive oil 69-50 parts blown neats-foot oil Example 16 55-50 parts olive oil 70 parts water 15 parts water soluble cellulose ester parts OR JJe0H-cyclohexylaminc salt I o eyl $01K (Bis-potassium suiio phenyl oleyl hygroxy methane cyclohcxylamine so parts sulfonated olive oil Example 18 One pound of 1-methylamino-4-ethylamino an; thraquinone is ground with V pound isopropyl SOxNa (2 isopropylalpha-solgllllgg mlditgi (11121-425131 hydroxy ethane phos and 3 pounds sugar. The resulting finely divided mixture is then added to 100 gallons water heated to 60-85 and the aqueous suspension is used to dye about 100 pounds of cellulose acetate blue.
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 amounts of conditioning liquid applied may vary between 5-25% by weight of the yarn. Usually, however, the amount of conditioning liquid applied is about 1015% 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 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 cellulose derivaished yarn, etc. .1
tive used in making the yarn, the solvent or solvent combination used in making up the spinning solution, and properties desired in the fin- It 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 ielt wet therewith, or the liquid may be applied by immersion, spray, or otherwise. The particular point at which the liquid is 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 socalled "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 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 it 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, nonsolvents, emulsifying agents, blending agents 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 ingredients, these percentages may vary widely depending upon the particular purpose for which the composition is intended. For example, if it is desired to control the deelectrifying 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 01' cellulose such as cellulose acetate, the conditioning agents and formulas described herein are 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 a thread, either of high or low twist, single or multiple threads associated or twisted together, composite threads composed of a mix ture of natural and artificial filaments or a composite thread formed by twisting together individual strands of natural or artificial materials. as well as cut staple fibers produced from natural and/or artificial filaments or threads and spun yarn produced from such staple fibers.
As indicated above, the yarn conditioning 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, neats-foot, 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 agents of our invention also have exceptional value as surface active compounds and as such may be employed as wetting agents, emulsifying and dispersing agents, textile assistants, dye dispersing agents and the like.
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 abilityto deelectrify yarns, especially those composed of or containing organic derivatives of cellulose such as cellulose acetate and render them amenable to various textile operations, especially operations such as those involved in the manufacture of cut staple fibers, as well as in weaving and knitting. Another outstanding characteristic of these compounds is their exceptional solvent power for a wide variety of mineral, animal, and vegetable oils and their ability to act as lubricating 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.
Of the above compositions we have found that bis-alpha-(meta sulfol phenyl-alpha-hydroxy pentane-alpha-phosphonic acid, bis-alpha-phenyl-alpha-hydroxy-decane phosphonic acid dimethyl cyclohexylamine salt, and bis-alphaphenyl-alpha-hydroxy phenyl heptane phosphonic acid are outstanding in their ability to reduce or eliminate the tendency of yarns composed of or containing organic derivatives of prises applying thereto a composition containing as its essential anti-static component a hydroxy alkyla aryl phosphonate having the general formula:
radicals.
3. The method of eliminating the tendency of yarns, filaments or fibers composed of or containing cellulose acetate to accumulate charges of static electricity, which comprises applying thereto a composition containing as its essential anti-static component a hydroxy alkyl aryl phosphonate having the general formula:
wherein R is an aromatic group; R and R are substituents selected fr m the group consisting of hydrogen, alkyl, cycloalkyl, aryl and heterocyclic groups, wherein R, is a substituent selected from the group consisting of hydrogen, alkyl, cycloalkyl; Z is a substituent selected from the group consisting of hydrogen and salt-forming radica s.
4. The method of eliminating the tendency of yarns, filaments or fibers composed of or containing organic derivatives of cellulose to accumulate charges of static electricity, which comprises applying thereto a composition containing as its essential anti-static component bis-alpha- (meta-sulfo) phenyl-alpha-hydroxy pentanealpha-phosphonic acid.
cellulose to accumulate charges of static electricity.
What we claim and desire to secure by Letters Patent of the United States is:
1. The method of eliminating the tendency of yarns, filaments or fibers to accumulate charges of static electricity, which comprises applying thereto a composition containing as its essential anti-static component a hydroxy alkyl aryl phosphonate having the general formula:
B RI
0 oz OH wherein R is an aromatic group; R and R. are substituents selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl and heterocyclic groups, wherein R is a substitute selected from the group consisting of hydrogen, alkyl,
5. The method of eliminating the tendency of yarns, filaments or fibers composed of or containing organic derivatives of cellulose to accumulate charges of static electricity, which comprises applying thereto a composition containing as its essential anti-static component bisalpha-phenyl-alpha-hydroxy-decane phosphonic acid dimethyl cyclohexylamine salt.
6. The method yarns, filaments taining organic mulate charges of eliminating the tendency of or fibers composed of or conderivatives of cellulose to accuof static electricity, which comprises applying thereto a composition containing as its essential anti-static component bis-alphaphenyl-alpha-hydroxy phenyl heptane phosphonic acid.
7. An anti-static composition adapted, when applied to textile yarns, filaments or fibers to eliminate the tendency of such materials to accumulate charges of static electricity, said composition containing as its essential anti-static component a hydroxy] alkyl aryl phosphonate having the general formula:
wherein R is an aromatic group, R and R are substituents selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl and heterocyclic groups, wherein 1'1. is a substituent selected from the group consisting of hydrogen, alkyl, cycloalkyl; Z is a substituent selected from the group consisting of hydrogen and salt-forming radicals.
8. An anti-static composition adapted, when applied to cellulose organic derivative yarns, filaments or fibers, to eliminate the tendency of such materials to accumulate charges of static electricity, said composition containing as its essential anti-static component a ,hydroxy alkyl aryl phosphonate having the general formula:
' fibers, to eliminate the tendency of such materials to accumulate charges of static electricity, said composition containing as its'essential antistatic component a hydroxy alkyl aryl phosphonate having the general formula:
wherein R is an aromatic group, R and R are substituents selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl and heterocyclic groups, wherein R is a substituent selected from the group consisting of hydrogen, alkyl, cycloalkyl; Z is a substituent selected from the group consisting of hydrogen and salt-forming radicals.
10. An anti-static composition adapted, when applied to cellulose organic derivative yarns, filaments or fibers to eliminate the tendency of such materials to accumulate charges of static electricity, said composition containing as its essential anti-static component bis-alpha-(metasulfo) phenyl-alpha-hydroxy pentane-alphaphosphonic acid.
11. An anti-static composition adapted, when applied to cellulose organic derivative yarns, filaments or fibers, to eliminate the tendency of such materials to accumulate charges of static electricity, said composition containing as its essential anti-static component bis-alpha-phenylalpha-hydroxy-decane-phosphonic acid dimethyl cyclohexylamine salt.
12. An anti-static composition adapted, when applied to cellulose organic derivative yarns, filaments or fibers, to eliminate the tendency of such materials to accumulate charges of static electricity, said composition containing as its essential anti-static component bis-alpha-phenylal-pha-hydroxy phenyl heptane phosphonic acid.
13. Textile yarns having a lessened tendency to accumulate charges of static electricity, said yarns containing a hydroxy alkyl aryl phosphonate having the general formula:
wherein R is an aromatic group; R and R are substituents selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl and heterocyclic groups, wherein R is a substituent selected from the group consisting of hydrogen, alkyl, cycloalkyl; Z is a substituent selected from the group consisting of hydrogen and salt-forming radicals.
14. Textile yarns composed of or containing organic derivatives of cellulose having a lessened tendency to accumulate charges of static electricity, said yarns containing a hydroxy alkyl aryl phosphonate having the general formula:
wherein R is an aromatic group; R and R are substituents selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl and heterocyclic groups, wherein R is a substituent selected from the group consisting of hydrogen, alkyl, cycloalkyl; Z is a substituent selected from the group consisting of hydrogen and salt-forming radicals.
l5. Textile yarns composed of or containing cellulose acetate having a lessened tendency to accumulate charges of static electricity, said yarns containing a hydroxy alkyl aryl phosphonate having the general formula:
wherein R is an aromatic group; R and R are substituents selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl and heterocyclic groups, wherein R is a substituent selected from the group consisting of hydrogen, alkyl, cycloalkyl; Z is a substituent selected from the group consisting of hydrogen and salt-forming radicals.
l6. Textile yarns composed of or containing organic derivatives of cellulose having a lessened tendency to accumulate charges of static elec-- JOSEPH B. DICKEY. JAllES G. MONALLY.
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Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2460043A (en) * | 1945-08-29 | 1949-01-25 | Allied Chem & Dye Corp | Phosphonic acid esters |
US2471472A (en) * | 1945-04-28 | 1949-05-31 | Victor Chemical Works | Method of forming phosphonic and thiophosphonic acid chlorides |
US2486657A (en) * | 1945-04-28 | 1949-11-01 | Monsanto Chemicals | Diolefin phosphonic acids and polymers thereof |
US2574955A (en) * | 1948-07-14 | 1951-11-13 | Tide Water Associated Oil Comp | Esterified alkylolamine salts of acid esters of phosphorus acids |
US2653113A (en) * | 1951-09-13 | 1953-09-22 | Du Pont | Sizing of ethylene polymer structures |
US2676120A (en) * | 1951-09-13 | 1954-04-20 | Du Pont | Sizing of ethylene polymer structures |
US2678285A (en) * | 1950-12-22 | 1954-05-11 | Ici Ltd | Articles comprising synthetic thermoplastic materials and method for coating same |
US4486357A (en) * | 1981-06-27 | 1984-12-04 | Hoechst Aktiengesellschaft | Process for making vinylphosphonic acid or vinylpyrophosphonic acid |
US4507249A (en) * | 1982-03-22 | 1985-03-26 | Hoechst Aktiengesellschaft | Process for making derivatives of vinylphosphonic acid or vinylpyrophosphonic acid |
US20070210288A1 (en) * | 2006-03-07 | 2007-09-13 | Clariant International Ltd | Mixtures composed of monocarboxy-functionalized dialkylphosphinic esters and of further components |
US20070213436A1 (en) * | 2006-03-07 | 2007-09-13 | Clariant International Ltd | Mixtures composed or monocarboxy-functionalized dialkylphosphinic acids, their use and a process for their preparation |
US20070213563A1 (en) * | 2006-03-07 | 2007-09-13 | Clariant International Ltd | Mixtures composed of monocarboxy-functionalized dialkylphosphinic acid salts, their use und a process for their preparation |
-
1940
- 1940-10-09 US US360450A patent/US2279501A/en not_active Expired - Lifetime
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2471472A (en) * | 1945-04-28 | 1949-05-31 | Victor Chemical Works | Method of forming phosphonic and thiophosphonic acid chlorides |
US2486657A (en) * | 1945-04-28 | 1949-11-01 | Monsanto Chemicals | Diolefin phosphonic acids and polymers thereof |
US2460043A (en) * | 1945-08-29 | 1949-01-25 | Allied Chem & Dye Corp | Phosphonic acid esters |
US2574955A (en) * | 1948-07-14 | 1951-11-13 | Tide Water Associated Oil Comp | Esterified alkylolamine salts of acid esters of phosphorus acids |
US2678285A (en) * | 1950-12-22 | 1954-05-11 | Ici Ltd | Articles comprising synthetic thermoplastic materials and method for coating same |
US2676120A (en) * | 1951-09-13 | 1954-04-20 | Du Pont | Sizing of ethylene polymer structures |
US2653113A (en) * | 1951-09-13 | 1953-09-22 | Du Pont | Sizing of ethylene polymer structures |
US4486357A (en) * | 1981-06-27 | 1984-12-04 | Hoechst Aktiengesellschaft | Process for making vinylphosphonic acid or vinylpyrophosphonic acid |
US4507249A (en) * | 1982-03-22 | 1985-03-26 | Hoechst Aktiengesellschaft | Process for making derivatives of vinylphosphonic acid or vinylpyrophosphonic acid |
US20070210288A1 (en) * | 2006-03-07 | 2007-09-13 | Clariant International Ltd | Mixtures composed of monocarboxy-functionalized dialkylphosphinic esters and of further components |
US20070213436A1 (en) * | 2006-03-07 | 2007-09-13 | Clariant International Ltd | Mixtures composed or monocarboxy-functionalized dialkylphosphinic acids, their use and a process for their preparation |
US20070213563A1 (en) * | 2006-03-07 | 2007-09-13 | Clariant International Ltd | Mixtures composed of monocarboxy-functionalized dialkylphosphinic acid salts, their use und a process for their preparation |
US7485745B2 (en) * | 2006-03-07 | 2009-02-03 | Clariant International Ltd. | Mixtures composed of monocarboxy-functionalized dialkylphosphinic esters and of further components |
US8097753B2 (en) * | 2006-03-07 | 2012-01-17 | Clariant Finance (Bvi) Limited | Mixtures composed or monocarboxy-functionalized dialkylphosphinic acids, their use and a process for their preparation |
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