US3493504A - Fiber lubricant - Google Patents
Fiber lubricant Download PDFInfo
- Publication number
- US3493504A US3493504A US560862A US3493504DA US3493504A US 3493504 A US3493504 A US 3493504A US 560862 A US560862 A US 560862A US 3493504D A US3493504D A US 3493504DA US 3493504 A US3493504 A US 3493504A
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- US
- United States
- Prior art keywords
- fiber
- lubricant
- yarn
- weight
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000000835 fiber Substances 0.000 title description 61
- 239000000314 lubricant Substances 0.000 title description 55
- -1 aliphatic dicarboxylic acid salt Chemical class 0.000 description 24
- 239000000203 mixture Substances 0.000 description 22
- 239000002253 acid Substances 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 239000007859 condensation product Substances 0.000 description 12
- 150000002191 fatty alcohols Chemical class 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- 150000004665 fatty acids Chemical class 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 125000002091 cationic group Chemical group 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 7
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- 235000021355 Stearic acid Nutrition 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 229940067597 azelate Drugs 0.000 description 5
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 239000008117 stearic acid Substances 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- RTMGQVSGXYZVTE-UHFFFAOYSA-L dipotassium;nonanedioate Chemical group [K+].[K+].[O-]C(=O)CCCCCCCC([O-])=O RTMGQVSGXYZVTE-UHFFFAOYSA-L 0.000 description 4
- 238000002845 discoloration Methods 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000009960 carding Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- KGBQOPAEFCWHDI-UHFFFAOYSA-N 2-aminoethanol octadecanoic acid Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)O.C(O)CN.C(O)CN KGBQOPAEFCWHDI-UHFFFAOYSA-N 0.000 description 1
- QNDLRZNYJFUSPE-UHFFFAOYSA-N 4,5-dioctadecyl-4,5-dihydro-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCCC1NC=NC1CCCCCCCCCCCCCCCCCC QNDLRZNYJFUSPE-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N N-butylamine Natural products CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 229940087594 dipotassium adipate Drugs 0.000 description 1
- QFYNUCAKHMSPCY-UHFFFAOYSA-L disodium;nonanedioate Chemical compound [Na+].[Na+].[O-]C(=O)CCCCCCCC([O-])=O QFYNUCAKHMSPCY-UHFFFAOYSA-L 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical class CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 229910001651 emery Inorganic materials 0.000 description 1
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 229940043348 myristyl alcohol Drugs 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- GCHCGDFZHOEXMP-UHFFFAOYSA-L potassium adipate Chemical compound [K+].[K+].[O-]C(=O)CCCCC([O-])=O GCHCGDFZHOEXMP-UHFFFAOYSA-L 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000010458 rotten stone Substances 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- KITSBOHZGUHIOU-UHFFFAOYSA-M sodium;9-hydroxy-9-oxononanoate Chemical compound [Na+].OC(=O)CCCCCCCC([O-])=O KITSBOHZGUHIOU-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005303 weighing Methods 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
- D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions
Definitions
- This invention relates to a fiber lubricant and more particularly to fiber lubricant compositions comprising as a lubricant base the condensation product of alkanolamines and fatty acids, as an emulsifying agent, a polyoxyalkylated fatty alcohol, and as a rust inhibitor, an aliphatic di-carboxylic acid salt.
- This invention pertains to the textile art and more particularly to the fiber lubricant art.
- the fiber to metal lubricity is needed in order to prevent 6XC6SSl ⁇ 8 breakage of the fiber during its processing into yarn in the carding and spinning operations.
- the fiber to fiber lubricity must be properly controlled in order to impart to the fibers cohesiveness properties which will prevent them from slipping and sliding during the carding and spinning operations.
- the fiber lubricant also impart to the fibers which are processed into carpet, low soiling characteristics.
- the materials which have been found most satisfactory as fiber lubricants have been cationic materials such as fatty irnidazoline salts.
- the cationic materials impart good anti-friction and low soiling properties to the fiber, they are very corrosive in nature and their use frequently results in the deposition of corrosion bodies on the yarns. The corrosion or rust comes from the non-stainless steel machinery which has been exposed to the conventional cationic lubricant.
- Some improvement in the cationic lubricants has been obtained by the addition of rust inhibitors to the cationic emulsions used; however, even with rust inhibitors, the cationic lubricants have not been able to provide entirely satisfactory results.
- the fiber lubricants of the present invention have overcome the above-noted problems of the past connected with cationic fiber lubricants by providing in a basic formulation, a material which in addition to being non-corrosive imparts to the fibers excellent lubricity and low soiling characteristics.
- the fiber lubricant compositions of the present invention comprise (1) the condensation product of an alltanolamine and a fatty acid, (2) a polyoxyalkylated fatty alcohol, and (3) an aliphatic dicarboxylic acid salt.
- the condensation product is prepared from an alkanolamine having the general structure wherein R and R are selected from the group consisting of hydrogen and lower hydroxy alkyl radicals and wherein at least one of R and R is a lower hydroxy alkyl radical, and a C C fatty acid.
- the fatty acid may be either saturated or unsaturated, although saturated acids are preferred.
- alkanolamines which may be used 3,493,5M Patented Feb. 3, 1970 are ethanolamine, diethanolamine, propanolamine, dipropanolamine, isopropanolamine, di-isopropanolamine, hydroxy butyl amine, and the like.
- fatty acids which may be used are stearic, palmitic, myristic, and oleic acids.
- the composition of the condensation product is dependent upon the amount of amine and acid used in its preparation but generally consists of a combination of mono-esters, di-esters, amides and ester-amides, predominantly the latter.
- the ratio of amine to fatty acid varies depending upon the functionality of the amine, but preferably about two equivalents of acid are used for every one equivalent of amine.
- the polyoxyalkylated fatty alcohols which are employed as emulsifying agents in the compositions of the present invention should conform to the structure wherein R is a lower divalent alkyl radical having from 2 to 3 carbon atoms, R is a higher hydrocarbon radical having from 6 to 18 carbon atoms, and n is an integer from 1 to 40, preferably from 20 to 25.
- the polyoxyalkylated fatty alcohols may be made by reacting such alkylene oxides as ethylene oxide or propylene oxide with lauryl alcohol, cetyl alcohol, 'myristyl alcohol or the like.
- lauryl as used herein is intended to include the fatty hydrocarbon chains of fatty alcohols derived from coconut fatty acids. Thus lauryl alcohol would include a mixture of alcohols having chain lengths of from 6 to 18 carbon atoms but predominantly 10 to 14 carbon atoms in length.
- the third essential ingredient of the present fiber lubricant compositions is an aliphatic dibasic acid salt which is used as a rust inhibitor.
- the aliphatic dibasic acid salts may be prepared from aliphatic dibasic acids having from about 6 to 12 carbon atoms including adipic, azelaic, sebacic, and dodecanoic acids.
- the metal component of the salt should be an alkali metal, preferably potassium or sodium and may be either mono or di-substituted although the former is preferred.
- dibasic salts which may be used are di-potasium azelate, mono-potassium azelate, disodium azelate, mono-sodium azelate, dipotassium adipate, di-potassiurn sebacate, and mono-potassium sebacate.
- the condensation product of an alkanolamine and a higher fatty acid should constitute from 50 to of the lubricant.
- the polyoxyalkylated fatty alcohol emulsifying agent should constitute from 9 to 40% and the aliphatic dibasic acid salt should constitute from 1 to 10% of the lubricant composition.
- the fiber lubricants of this invention may be prepared by melting the alkanolamine-higher fatty acid condensation product and the polyoxyalkylated fatty alcohol, which are usually solids, and blending the two materials together. Thereafter, the aliphatic carboxylic dibasic acid such as azelaic acid, is intermixed with the blend and after it has melted into the blend, an alkali solution of either potassium hydroxide or sodium hydroxide is added to saponify the acid and produce the aliphatic carboxylic dibasic acid salt.
- the fiber lubricants are ordinarily used in the form of an aqueous emulsion and thus water is usually added to the melted blend in an amount which gives the dilution desired, and stirring is continued until. a completely emulsified and homogenized blend is obtained, after which the resulting emulsion is cooled.
- the fiber lubricant is prepared by blending together 20 weight percent of the condensation product of di-ethanolamine and stearic acid which is prepared by reacting the stearic acid with the amine at a ratio of about two moles of acid to one of amine, the product being principally Z-(N-hydroxy ethyl) stearamido ethyl. 4.5 weight percent of ethoxylated lauryl alcohol, 0.5 weight percent monopotassium azelate and 75% by weight water.
- the relative amounts of the three active ingredients of the composition which can be used is rather restricted.
- the di-ethanolamine-stearic acid reaction product must constitute from 70 to 90% by weight of the three component lubricant mixture, the ethoxylated lauryl alcohol must constitute from 10 to 30%, and the mono-potassium azelate must constitute from 1.0 to 5% by weight of the basic lubricant composition.
- the fiber lubricant of the present invention may be applied to the fibers either before or after they have been dyed by spraying the lubricant composition, usually in water-diluted form, onto the fiber prior to the processing of the fiber, or the lubricant may be incorporated in the aqueous rinse which is used upon the fiber after the fiber has been dyed.
- the fiber absorbs the lubricant from the rinse water in the latter instance.
- a lubricant base was prepared in the following manner: A reaction vessel was charged with 105 parts of di-ethanolamine and 540 parts of stearic acid of the conventional triple press grade. These two reactants were heated at 225 C. until two mole equivalents of water had been removed and the acid value was reduced to 3.8. The reaction product was then cooled under vacuum.
- a fiber lubricant was prepared by melting and then blending together 200 grams of the reaction product of Example I and 45 grams of a polyoxyalkylated fatty alcohol, polyoxyethylene (23) lauryl ether. To the blend was added 3 grams of azelaic acid which was melted into the blend and then 2 ml. of a 50% solution of potassium hydroxide (50 weight percent KOH) was added to the blend as it was being stirred. While the melted blend was still hot, 750 ml. of water were added and the blend was stirred until a completely emulsified and homogenized product was obtained, and then the resulting material was cooled.
- azelaic acid which was melted into the blend and then 2 ml. of a 50% solution of potassium hydroxide (50 weight percent KOH) was added to the blend as it was being stirred. While the melted blend was still hot, 750 ml. of water were added and the blend was stirred until a completely emulsified and homogenized product was obtained, and
- EXAMPLE III The corrosion resistance of the fiber lubricant prepared in Example II was determined in the following manner: A metal non-stainless steel pad thoroughly cleaned with acetone was placed in a jar after which it was covered with the lubricant of Example II. The jar was then closed and stored for one week at room temperature.
- Fiber lubricant used Corrosive activity after one week Fiber lubricant of EX- ample II No emulsion discoloration or 10% solution of lubripad rusting.
- Example II No emulsion discoloration or 10% solution of catpad rusting.
- the lubricity of a fiber treated with the fiber lubricant of the present invention was determined by impregnating a fiber sample with an emulsion of the fiber lubricant of Example II which was diluted at a :5 water to lubricant ratio giving an aqueous emulsion having 1% active lubricant ingredients.
- the impregnation was performed by passing the yarn sample through a bath of the dilute emulsion and then squeezing the yarn with a hand wringer and drying on a non-absorbent surface. About wet pick-up of the solution was accomplished following this procedure.
- the fiber to metal lubricity was measured by attaching the lubricated yarn to a gram scale, then passing it under but in contact with a steel wheel and finally threading it over a free pulley to which is attached at the other end of the yarn a weight, i.e., SO-gram weight.
- the steel wheel was rotated against the fiber to determine the frictional force, which was read from the gram scale.
- the yarn treated as described above and tested for friction with this apparatus showed a fiber to metal friction of 68 grams.
- An untreated yarn was tested for friction and showed a fiber to metal friction of 72 grams.
- EXAMPLE V The soil resistance of the fiber lubricant of Example II was determined in the following manner: Yarn samples of polypropylene, acrylic, nylon, wool, and polyester each weighing 2.5 grams were thoroughly scoured with a commercial nonionic detergent, ethoxylated nonyl phenol and soda ash, then rinsed in distilled water and rerinsed in both ethyl ether and isopropanol. The emulsion of Example II was dissolved in a 90:10 ethyl ester-isopropanol solution and then applied to the various yarn samples in an amount of 0.5% active lubricant ingredients (based on the weight of the yarn) and was worked into the yarn.
- the yarn samples were cut into 1 /2- to 2-inch strips and were tightly placed parallel to each other on a glass plate covered with gray cardboard.
- a second plate covered with black cardboard except for an opening through which readings could be taken was placed over the yarn samples.
- the plates were securely clamped together with rubber bands and the resulting sandwich was then placed over an opening on a Gardner Reflectometer and readings were taken on the green filter only (66.2 standard).
- a standard or blank sample of each of the yarns was also prepared in which the straight ethyl ether-isopropanol solution was applied to the yarns.
- the individual strips were then placed in pint jars containing (1) ten stainless steel balls A inch in diameter and (2) two grams of artificial soil consisting of 0.1% carbon black, 1.7% rottenstone, and 98.2% sodium sulfate as a carrier.
- the jars containing the yarn and artificial soil were then securely clamped in a Launder- Ometer and tumbled for fifteen minutes at 42 r.p.m. per minute.
- the yarn strips were then transferred to dusting cans which were 4 /2 inches in diameter and 4% inches high and have 4; -inch holes /2 inch apart at the top and bottom, 1 inch apart horizontally and /2 inch apart vertically on the sides.
- the yarn soiling is determined in terms of a soiling index or percent increase or decrease in the soiling of the treated as compared with the untreated yarn.
- the soiling index is obtained by use of the following formula:
- A change in reflectance of treated yarn.
- A change in reflectance of untreated yarn.
- the soil resistance properties of propylene, nylon, and wool are enhanced by the use of the fiber lubricant of the present invention.
- the results obtained with acrylic and polyester fibers may superficially appear to be objectionable, however, fiber lubricants are essential in the processing of these fibers and the percentage increase in soiling propensities as shown in the above results is actually far less than is normally experienced.
- Acrylic and polyester fibers generally tend to soil less when used in the untreated form.
- a fiber lubricant consisting essentially of (a) from 50 to 90% by weight of a condensation prodduct of (i) an alkanolarnine having the structure R1I lH wherein R and R are selected from the group consisting of hydrogen and lower hydroxy alkyl radicals and wherein at least one of R and R is a lower hydroxy alkyl radical, and (ii) a straight chain higher fatty acid containing from about 9 to 24 carbon atoms;
- R is selected from the group consisting of ethylene and propylene radicals, and n is an integer from to 25.
- dibasic acid salt is selected from the group consisting of aliphatic hydrocarbon dibasic acid salts of sodium and potassium.
- condensation product is prepared from the reaction of di-ethanolamine and stearic acid, said polyo-xyalkylated fatty alcohol is polyoxyalkylated lauryl alcohol, and said dibasic acid salt is potassium azelate.
- the lubricant of claim 5 which comprises from by weight of said condensation product, from 10 30% by weight of said ethoxylated lauryl ether, and from 1.05.0% by weight of said potassium azelate.
- a method for lubricating a textile fiber which comprises applying to said fiber a fiber lubricant consisting essentially of (a) from 50 to 90% by weight of a condensation product of (i) an alkanolamine having the structure 1'12 Fir-NH wherein R and R are selected from the group consisting of hydrogen and lower hydroxy alkyl radicals and wherein at least one of R and R is a lower hydroxy alkyl radical, and (ii) a straight chain higher fatty acid containing from about 9 to 24 carbon atoms;
- condensation product is prepared from the reaction of di-ethanolamine and stearic acid, said polyoxyalkylated fatty alcohol is ethoxylated lauryl alcohol, and said dibasic acid salt is potassium azelate.
- said lubricant comprises from 70-90% by weight of said condensation product, from 1030% of said ethoxylated lauryl ether, and from 1.05.0% by weight of said potassium azelate.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
3,493,504 FIBER LUBRICANT Herman T. Buckley, Cincinnati, Ohio, assignor to Emery industries, Inn, Cincinnati, Ohio, a corporation of Ohio No sawing. Filed June 27, 1966, Ser. No. 560,862 inf. Cl. B06211 15/44, 13/34 U5. Cl. 252-8.8 Claims ABTRACT OF THE DISCLOSURE This invention relates to a fiber lubricant and more particularly to fiber lubricant compositions comprising as a lubricant base the condensation product of alkanolamines and fatty acids, as an emulsifying agent, a polyoxyalkylated fatty alcohol, and as a rust inhibitor, an aliphatic di-carboxylic acid salt.
BACKGROUND OF THE INVENTION This invention pertains to the textile art and more particularly to the fiber lubricant art. In the textile field, it is necessary to prepare the fibers prior to their processing so that they have the proper balance of What is called fiber to metal and fiber to fiber lubricity. The fiber to metal lubricity is needed in order to prevent 6XC6SSl\8 breakage of the fiber during its processing into yarn in the carding and spinning operations. The fiber to fiber lubricity must be properly controlled in order to impart to the fibers cohesiveness properties which will prevent them from slipping and sliding during the carding and spinning operations. Also, in the fiber art, particularly in the carpet field, it is essential that the fiber lubricant also impart to the fibers which are processed into carpet, low soiling characteristics. In the past, the materials which have been found most satisfactory as fiber lubricants have been cationic materials such as fatty irnidazoline salts. Although the cationic materials impart good anti-friction and low soiling properties to the fiber, they are very corrosive in nature and their use frequently results in the deposition of corrosion bodies on the yarns. The corrosion or rust comes from the non-stainless steel machinery which has been exposed to the conventional cationic lubricant. Some improvement in the cationic lubricants has been obtained by the addition of rust inhibitors to the cationic emulsions used; however, even with rust inhibitors, the cationic lubricants have not been able to provide entirely satisfactory results.
The fiber lubricants of the present invention have overcome the above-noted problems of the past connected with cationic fiber lubricants by providing in a basic formulation, a material which in addition to being non-corrosive imparts to the fibers excellent lubricity and low soiling characteristics.
DESCRIPTION OF THE INVENTION The fiber lubricant compositions of the present invention comprise (1) the condensation product of an alltanolamine and a fatty acid, (2) a polyoxyalkylated fatty alcohol, and (3) an aliphatic dicarboxylic acid salt.
The condensation product is prepared from an alkanolamine having the general structure wherein R and R are selected from the group consisting of hydrogen and lower hydroxy alkyl radicals and wherein at least one of R and R is a lower hydroxy alkyl radical, and a C C fatty acid. The fatty acid may be either saturated or unsaturated, although saturated acids are preferred. Examples of alkanolamines which may be used 3,493,5M Patented Feb. 3, 1970 are ethanolamine, diethanolamine, propanolamine, dipropanolamine, isopropanolamine, di-isopropanolamine, hydroxy butyl amine, and the like. Among the fatty acids which may be used are stearic, palmitic, myristic, and oleic acids. The composition of the condensation product is dependent upon the amount of amine and acid used in its preparation but generally consists of a combination of mono-esters, di-esters, amides and ester-amides, predominantly the latter. The ratio of amine to fatty acid varies depending upon the functionality of the amine, but preferably about two equivalents of acid are used for every one equivalent of amine.
The polyoxyalkylated fatty alcohols which are employed as emulsifying agents in the compositions of the present invention should conform to the structure wherein R is a lower divalent alkyl radical having from 2 to 3 carbon atoms, R is a higher hydrocarbon radical having from 6 to 18 carbon atoms, and n is an integer from 1 to 40, preferably from 20 to 25. The polyoxyalkylated fatty alcohols may be made by reacting such alkylene oxides as ethylene oxide or propylene oxide with lauryl alcohol, cetyl alcohol, 'myristyl alcohol or the like. The term lauryl as used herein is intended to include the fatty hydrocarbon chains of fatty alcohols derived from coconut fatty acids. Thus lauryl alcohol would include a mixture of alcohols having chain lengths of from 6 to 18 carbon atoms but predominantly 10 to 14 carbon atoms in length.
The third essential ingredient of the present fiber lubricant compositions is an aliphatic dibasic acid salt which is used as a rust inhibitor. The aliphatic dibasic acid salts may be prepared from aliphatic dibasic acids having from about 6 to 12 carbon atoms including adipic, azelaic, sebacic, and dodecanoic acids. The metal component of the salt should be an alkali metal, preferably potassium or sodium and may be either mono or di-substituted although the former is preferred. Examples of suitable dibasic salts which may be used are di-potasium azelate, mono-potassium azelate, disodium azelate, mono-sodium azelate, dipotassium adipate, di-potassiurn sebacate, and mono-potassium sebacate.
In the formulation of the fiber lubricants of the present invention, the condensation product of an alkanolamine and a higher fatty acid should constitute from 50 to of the lubricant. The polyoxyalkylated fatty alcohol emulsifying agent should constitute from 9 to 40% and the aliphatic dibasic acid salt should constitute from 1 to 10% of the lubricant composition.
The fiber lubricants of this invention may be prepared by melting the alkanolamine-higher fatty acid condensation product and the polyoxyalkylated fatty alcohol, which are usually solids, and blending the two materials together. Thereafter, the aliphatic carboxylic dibasic acid such as azelaic acid, is intermixed with the blend and after it has melted into the blend, an alkali solution of either potassium hydroxide or sodium hydroxide is added to saponify the acid and produce the aliphatic carboxylic dibasic acid salt. The fiber lubricants are ordinarily used in the form of an aqueous emulsion and thus water is usually added to the melted blend in an amount which gives the dilution desired, and stirring is continued until. a completely emulsified and homogenized blend is obtained, after which the resulting emulsion is cooled.
In one preferred embodiment of the present invention the fiber lubricant is prepared by blending together 20 weight percent of the condensation product of di-ethanolamine and stearic acid which is prepared by reacting the stearic acid with the amine at a ratio of about two moles of acid to one of amine, the product being principally Z-(N-hydroxy ethyl) stearamido ethyl. 4.5 weight percent of ethoxylated lauryl alcohol, 0.5 weight percent monopotassium azelate and 75% by weight water. In this particular embodiment of the present invention, the relative amounts of the three active ingredients of the composition which can be used is rather restricted. The di-ethanolamine-stearic acid reaction product must constitute from 70 to 90% by weight of the three component lubricant mixture, the ethoxylated lauryl alcohol must constitute from 10 to 30%, and the mono-potassium azelate must constitute from 1.0 to 5% by weight of the basic lubricant composition.
The fiber lubricant of the present invention may be applied to the fibers either before or after they have been dyed by spraying the lubricant composition, usually in water-diluted form, onto the fiber prior to the processing of the fiber, or the lubricant may be incorporated in the aqueous rinse which is used upon the fiber after the fiber has been dyed. The fiber absorbs the lubricant from the rinse water in the latter instance.
The following examples are provided to further illustrate the invention but are not to be construed as limitative of the scope thereof:
EXAMPLE I A lubricant base was prepared in the following manner: A reaction vessel was charged with 105 parts of di-ethanolamine and 540 parts of stearic acid of the conventional triple press grade. These two reactants were heated at 225 C. until two mole equivalents of water had been removed and the acid value was reduced to 3.8. The reaction product was then cooled under vacuum.
EXAMPLE II A fiber lubricant was prepared by melting and then blending together 200 grams of the reaction product of Example I and 45 grams of a polyoxyalkylated fatty alcohol, polyoxyethylene (23) lauryl ether. To the blend was added 3 grams of azelaic acid which was melted into the blend and then 2 ml. of a 50% solution of potassium hydroxide (50 weight percent KOH) was added to the blend as it was being stirred. While the melted blend was still hot, 750 ml. of water were added and the blend was stirred until a completely emulsified and homogenized product was obtained, and then the resulting material was cooled.
EXAMPLE III The corrosion resistance of the fiber lubricant prepared in Example II was determined in the following manner: A metal non-stainless steel pad thoroughly cleaned with acetone was placed in a jar after which it was covered with the lubricant of Example II. The jar was then closed and stored for one week at room temperature. Three additional tests were conducted in this same manner except that in one a solution of the material of Example 11 prepared by diluting the lubricant of Example II at a 90:10 ratio of water to lubricant was used, in the second a conventional ionic type fiber lubricant containing as the active cationic agent, distearyl imidazoline, in an aqueous solution in which the active material was approximately the same strength as the 90: 10 diluted fiber lubricant described above was used, and the third was a blank test in which water alone was used.
Fiber lubricant used: Corrosive activity after one week Fiber lubricant of EX- ample II No emulsion discoloration or 10% solution of lubripad rusting.
cant of Example II No emulsion discoloration or 10% solution of catpad rusting.
ionic lubricant Severe emulsion discoloration and pad rusting. Water Severe pad rusting and water discoloration.
4 EXAMPLE IV The lubricity of a fiber treated with the fiber lubricant of the present invention was determined by impregnating a fiber sample with an emulsion of the fiber lubricant of Example II which was diluted at a :5 water to lubricant ratio giving an aqueous emulsion having 1% active lubricant ingredients. The impregnation was performed by passing the yarn sample through a bath of the dilute emulsion and then squeezing the yarn with a hand wringer and drying on a non-absorbent surface. About wet pick-up of the solution was accomplished following this procedure. The fiber to metal lubricity was measured by attaching the lubricated yarn to a gram scale, then passing it under but in contact with a steel wheel and finally threading it over a free pulley to which is attached at the other end of the yarn a weight, i.e., SO-gram weight. The steel wheel was rotated against the fiber to determine the frictional force, which was read from the gram scale. The yarn treated as described above and tested for friction with this apparatus showed a fiber to metal friction of 68 grams. An untreated yarn was tested for friction and showed a fiber to metal friction of 72 grams.
EXAMPLE V The soil resistance of the fiber lubricant of Example II was determined in the following manner: Yarn samples of polypropylene, acrylic, nylon, wool, and polyester each weighing 2.5 grams were thoroughly scoured with a commercial nonionic detergent, ethoxylated nonyl phenol and soda ash, then rinsed in distilled water and rerinsed in both ethyl ether and isopropanol. The emulsion of Example II was dissolved in a 90:10 ethyl ester-isopropanol solution and then applied to the various yarn samples in an amount of 0.5% active lubricant ingredients (based on the weight of the yarn) and was worked into the yarn. The yarn samples were cut into 1 /2- to 2-inch strips and were tightly placed parallel to each other on a glass plate covered with gray cardboard. A second plate covered with black cardboard except for an opening through which readings could be taken was placed over the yarn samples. The plates were securely clamped together with rubber bands and the resulting sandwich was then placed over an opening on a Gardner Reflectometer and readings were taken on the green filter only (66.2 standard). A standard or blank sample of each of the yarns was also prepared in which the straight ethyl ether-isopropanol solution was applied to the yarns. After their reflectance was measured, the individual strips were then placed in pint jars containing (1) ten stainless steel balls A inch in diameter and (2) two grams of artificial soil consisting of 0.1% carbon black, 1.7% rottenstone, and 98.2% sodium sulfate as a carrier. The jars containing the yarn and artificial soil were then securely clamped in a Launder- Ometer and tumbled for fifteen minutes at 42 r.p.m. per minute. The yarn strips were then transferred to dusting cans which were 4 /2 inches in diameter and 4% inches high and have 4; -inch holes /2 inch apart at the top and bottom, 1 inch apart horizontally and /2 inch apart vertically on the sides. Ten clean steel balls /2 inch in diameter were added to the cans and the cans were tumbled in the Launder-Ometer for thirty minutes after which their reflectance was again measured with a Gardner Reflectometer. The yarn soiling is determined in terms of a soiling index or percent increase or decrease in the soiling of the treated as compared with the untreated yarn. The soiling index is obtained by use of the following formula:
A =change in reflectance of treated yarn. A =change in reflectance of untreated yarn.
The results obtained with the various fibers are shown in the table below:
Percent increase or Fiber: decrease in soiling Polypropylene l0.2 Acrylic +287 Nylon -l.4 Wool l.0 Polyester +4.0
As may be seen from the above results, the soil resistance properties of propylene, nylon, and wool are enhanced by the use of the fiber lubricant of the present invention. The results obtained with acrylic and polyester fibers may superficially appear to be objectionable, however, fiber lubricants are essential in the processing of these fibers and the percentage increase in soiling propensities as shown in the above results is actually far less than is normally experienced. Acrylic and polyester fibers generally tend to soil less when used in the untreated form.
What I claim is:
1. A fiber lubricant consisting essentially of (a) from 50 to 90% by weight of a condensation prodduct of (i) an alkanolarnine having the structure R1I lH wherein R and R are selected from the group consisting of hydrogen and lower hydroxy alkyl radicals and wherein at least one of R and R is a lower hydroxy alkyl radical, and (ii) a straight chain higher fatty acid containing from about 9 to 24 carbon atoms;
(b) from about 9 to 40% by weight of a polyoxyalkylated fatty alcohol having the structure wherein R is a lower alkylene radical having from 2 to 3 carbon atoms and R is a hydrocarbon radical having from 6 to 12 carbon atoms, and n is an integer from 1 to 40; and
(c) from about 1 to 10% by weight of an aliphatic hydrocarbon dicarboxylic acid salt containing from about 6 to 12 carbon atoms.
2. The lubricant of claim 1 wherein R is selected from the group consisting of ethylene and propylene radicals, and n is an integer from to 25.
3. The lubricant of claim 2 wherein said dibasic acid salt is selected from the group consisting of aliphatic hydrocarbon dibasic acid salts of sodium and potassium.
4. The lubricant of claim 3 wherein said condensation product is prepared from the reaction of di-ethanolamine and stearic acid, said polyo-xyalkylated fatty alcohol is polyoxyalkylated lauryl alcohol, and said dibasic acid salt is potassium azelate.
5. The lubricant of claim 4 wherein said dibasic acid salt is mono-potassium azelate.
6. The lubricant of claim 5 which comprises from by weight of said condensation product, from 10 30% by weight of said ethoxylated lauryl ether, and from 1.05.0% by weight of said potassium azelate.
7. An aqueous solution of the lubricant of claim 3.
8. A method for lubricating a textile fiber which comprises applying to said fiber a fiber lubricant consisting essentially of (a) from 50 to 90% by weight of a condensation product of (i) an alkanolamine having the structure 1'12 Fir-NH wherein R and R are selected from the group consisting of hydrogen and lower hydroxy alkyl radicals and wherein at least one of R and R is a lower hydroxy alkyl radical, and (ii) a straight chain higher fatty acid containing from about 9 to 24 carbon atoms;
(b) from about 9 to 40% by weight of a polyoxyalkylated fatty alcohol having the structure wherein R is a lower alkylene radical having from 2 to 3 carbon atoms and R is a hydrocarbon radical having from 6 to 18 carbon atoms, and n is an integer from 1 to 40;
(c) from about 1 to 10% by weight of an aliphatic hydrocarbon dicarboxylic acid salt containing from about 6 to 12 carbon atoms.
9. The method of claim 8 wherein said condensation product is prepared from the reaction of di-ethanolamine and stearic acid, said polyoxyalkylated fatty alcohol is ethoxylated lauryl alcohol, and said dibasic acid salt is potassium azelate.
10. The method of claim 9 wherein said lubricant comprises from 70-90% by weight of said condensation product, from 1030% of said ethoxylated lauryl ether, and from 1.05.0% by weight of said potassium azelate.
References Cited UNITED STATES PATENTS 2,426,968 8/1947 Farley 252-396 X 2,540,678 2/1951 Kelley 2528.8 X 2,628,937 2/1953 Paul 252-8.8 2,730,498 1/1956 Fortress et al 252-88 2,857,330 10/1958 Hall 2528.8 3,029,204 4/1962 Matuszak et al. 252-396 X LEON D. ROSDOL, Primary Examiner I. GLUCK, Assistant Examiner U.S. Cl. X.R.
ll7l39.5; 2528.9, 8.75, 396
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56086266A | 1966-06-27 | 1966-06-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3493504A true US3493504A (en) | 1970-02-03 |
Family
ID=24239671
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US560862A Expired - Lifetime US3493504A (en) | 1966-06-27 | 1966-06-27 | Fiber lubricant |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3493504A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3634117A (en) * | 1968-02-17 | 1972-01-11 | Glanzstoff Ag | A textile material coated with an ammonium dialkyl phosphate antistatic agent |
| FR2286800A1 (en) * | 1974-10-03 | 1976-04-30 | Owens Corning Fiberglass Corp | SIZING FOR FIBERGLASS REINFORCEMENT OF PLASTIC OBJECTS |
| US4066558A (en) * | 1974-02-11 | 1978-01-03 | Ici Americas Inc. | Low viscosity spin finish systems for neat finish application |
| US5190676A (en) * | 1989-11-30 | 1993-03-02 | Kao Corporation | High-speed spinning oil composition containing an organophosphoric ester salt and an oxyalkylene polymer |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2426968A (en) * | 1944-11-06 | 1947-09-02 | Seagram & Sons Inc | Method of esterifying polyhydric organic compounds |
| US2540678A (en) * | 1946-12-06 | 1951-02-06 | Nopco Chem Co | Fatty acid alkylolamine condensation and products |
| US2628937A (en) * | 1949-01-18 | 1953-02-17 | Courtaulds Ltd | Antistatic textile treating composition of triethanolamine-aliphatic carboxylic acidsalts |
| US2730498A (en) * | 1952-01-09 | 1956-01-10 | Celanese Corp | Textile lubricants |
| US2857330A (en) * | 1955-12-06 | 1958-10-21 | American Viscose Corp | Anhydrous textile finishes |
| US3029204A (en) * | 1959-05-12 | 1962-04-10 | Exxon Research Engineering Co | Acidic partial esters as lubricating oil additives |
-
1966
- 1966-06-27 US US560862A patent/US3493504A/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2426968A (en) * | 1944-11-06 | 1947-09-02 | Seagram & Sons Inc | Method of esterifying polyhydric organic compounds |
| US2540678A (en) * | 1946-12-06 | 1951-02-06 | Nopco Chem Co | Fatty acid alkylolamine condensation and products |
| US2628937A (en) * | 1949-01-18 | 1953-02-17 | Courtaulds Ltd | Antistatic textile treating composition of triethanolamine-aliphatic carboxylic acidsalts |
| US2730498A (en) * | 1952-01-09 | 1956-01-10 | Celanese Corp | Textile lubricants |
| US2857330A (en) * | 1955-12-06 | 1958-10-21 | American Viscose Corp | Anhydrous textile finishes |
| US3029204A (en) * | 1959-05-12 | 1962-04-10 | Exxon Research Engineering Co | Acidic partial esters as lubricating oil additives |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3634117A (en) * | 1968-02-17 | 1972-01-11 | Glanzstoff Ag | A textile material coated with an ammonium dialkyl phosphate antistatic agent |
| US4066558A (en) * | 1974-02-11 | 1978-01-03 | Ici Americas Inc. | Low viscosity spin finish systems for neat finish application |
| FR2286800A1 (en) * | 1974-10-03 | 1976-04-30 | Owens Corning Fiberglass Corp | SIZING FOR FIBERGLASS REINFORCEMENT OF PLASTIC OBJECTS |
| US5190676A (en) * | 1989-11-30 | 1993-03-02 | Kao Corporation | High-speed spinning oil composition containing an organophosphoric ester salt and an oxyalkylene polymer |
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