US3423235A - Organosiloxane-containing finishes for organic fibers - Google Patents
Organosiloxane-containing finishes for organic fibers Download PDFInfo
- Publication number
- US3423235A US3423235A US413304A US3423235DA US3423235A US 3423235 A US3423235 A US 3423235A US 413304 A US413304 A US 413304A US 3423235D A US3423235D A US 3423235DA US 3423235 A US3423235 A US 3423235A
- Authority
- US
- United States
- Prior art keywords
- organic
- fiber
- finishes
- fibers
- yarn
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000835 fiber Substances 0.000 title description 32
- 125000005375 organosiloxane group Chemical group 0.000 title description 3
- 239000000203 mixture Substances 0.000 description 17
- 229920001296 polysiloxane Polymers 0.000 description 15
- 239000003921 oil Substances 0.000 description 13
- -1 Dimethylsiloxane Chemical class 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 239000012530 fluid Substances 0.000 description 9
- 229920000742 Cotton Polymers 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- 239000001993 wax Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000012188 paraffin wax Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 239000000919 ceramic Substances 0.000 description 3
- 239000004205 dimethyl polysiloxane Substances 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000001050 lubricating effect Effects 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
- WJECKFZULSWXPN-UHFFFAOYSA-N 1,2-didodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1CCCCCCCCCCCC WJECKFZULSWXPN-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 1
- 229920004934 Dacron® Polymers 0.000 description 1
- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 125000001204 arachidyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229940100539 dibutyl adipate Drugs 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229960004132 diethyl ether Drugs 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- OJXOOFXUHZAXLO-UHFFFAOYSA-M magnesium;1-bromo-3-methanidylbenzene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C1=CC=CC(Br)=C1 OJXOOFXUHZAXLO-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- JZALLXAUNPOCEU-UHFFFAOYSA-N tetradecylbenzene Chemical compound CCCCCCCCCCCCCCC1=CC=CC=C1 JZALLXAUNPOCEU-UHFFFAOYSA-N 0.000 description 1
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000004711 α-olefin 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M7/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made of other substances with subsequent freeing of the treated goods from the treating medium, e.g. swelling, e.g. polyolefins
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/40—Reduced friction resistance, lubricant properties; Sizing compositions
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2962—Silane, silicone or siloxane in coating
Definitions
- This application relates to organosiloxane-containing finishes for organic fibers.
- Dimethylpolysiloxane is a known finish for organic fibers such as thread and yarn. It imparts superior and long lasting lubricity to the fibers, even when high temperatures and loads that would destroy organic finishes are generated on the fiber surface through friction.
- dimethylpolysiloxane-finished threads and yarns are often used in high speed sewing and weaving machines where high friction can cause frequent fiber breakage is nonsilicone fiber finishes are used.
- Waxy fiber finishes can be used to hold fibers together in a thread or yarn.
- This application discloses new silicone compositions that possess the excellent fiber lubricating properties of dimethylpolysiloxane, yet which are compatible with almost all organic oils and waxes.
- improved organic fiber finishes are obtained at low cost, showing superiority over nonsilicone fiber finishes.
- the silicone compositions of this invention include waxy materials as well as fluids, and are superior to organic fiber finishes whether used alone or in com-bination with other materials.
- This invention relates to the process of applying to an 3,423,235 Patented Jan. 21, 1969 organic fiber a composition
- a composition comprising a polymeric siloxane consisting essentially of r (-Si 0-) units and (b) at least one unit per molecule, where R is an alkyl radical with an average of at least 14 carbon atoms and n has a value of 1 to 2, there being an average of from 1 to 12 (b) units for every 20 (a) units present, and there being an average of 4 to (a) units per polymer molecule, whereby a lubricated fiber is formed.
- R can be any alkyl radical of at least 14 carbon atoms such as the tetradecyl, octadecyl, eicosyl, and myricyl radicals. Compositions containing mixtures of R groups are acceptable for use in this invention.
- the silicone of this invention can be diluted with an organic diluent in any proportion, though it is preferred to have at least one weight percent of the sillcone of this invention present based on the weight of the diluted composition.
- the organic diluent can be a material suitable for use as a fiber lubricant, e.g. any nondrying organic oil such as naphthenic base, paraifinic base, or mixed base petroleum lubricating oils, other hydrocarbon lubricants, such as lubricating oils derived from coal products and synthetic oils, e.g. alkylene polymers (such as polymers of propylene, butylene, etc., and mixtures thereof).
- a fiber lubricant e.g. any nondrying organic oil such as naphthenic base, paraifinic base, or mixed base petroleum lubricating oils, other hydrocarbon lubricants, such as lubricating oils derived from coal products and synthetic oils, e.g. alkylene polymers (such as polymers of propylene, butylene, etc., and mixtures thereof).
- alkylene oxide-type polymers dicarboxylic acid esters, liquid esters of acids of phosphorus, alkyl aromatic hydrocarbons, and synthetic oils of the alkylene oxide-type polymers may be used, eg propylene oxide polymers produced by polymerizing propylene oxide in the presence of water or alcohols such as ethyl alcohol.
- Esters of ethylene oxide-type polymers such as acetylated propylene oxide polymers prepared by acetylating propylene oxide polymers containing hydroxyl groups, polyethers prepared from alkylene glycols such as ethylene glycol, fatty acid esters, and other organic oils are all suitable.
- the polymeric products prepared from the various alkylene oxides and alkylene glycols may be polyoxyalkylene diols or polyalkylene glycol derivatives; that is, the terminal hydroxy group can remain as such, or one or both of the terminal hydroxy groups can be removed during the polymerization reaction by esterification or etherification.
- Synthetic oils of the dicarboxyli acid ester type include those which are prepared by esterification such dicarboxylic acids as adipic acid, azelaic acid, suberic acid, sebacic acid, alkenyl succinic acid, fumaric acid, maleic acid, etc., with alcohols such as :butyl alcohol, hexyl alcohol, 2-ethylhexyl alcohol, dodecyl alcohol, etc.
- Examples of dibasic (dicarboxylic) acid ester syntheti oils include dibutyl adipate, dihexyl adipate, di-Z-ethylhexyl sebacate, di-n-hexylfumaric polymer.
- Synthetic oils of the alkyl aromatic type include those which are prepared by alkylating benzene (e.g., dodecylbenzene, tetradecylbenzene, didodecylbenzene, etc.).
- Polyhydric alcohol esters such as esters of trimethylol propane and pentaerythritol are also usable.
- Organic waxes such as paraffin, beeswax, r carnauba wax can also be used as the diluent.
- volatile solvents are isopropanol, benzene, heptane, cyclo hexane, acetone, diethylether, naphtha, trifluorotrichloroethane, dichlorobenzene and carbon tetrachloride.
- organic diluent if present at all, to be present in the amount of 50 to 99 weight percent, based on the total weight of the composition, and for essentially all of the rest of the composition to be the silicone of this invention.
- the silicones of this invention will tend to be waxy, which is preferred. If R has an average of less than 20 carbon atoms, the silicones of this invention will tend to be fluids, which may be desirable in many circumstances.
- the silicones of this invention can be made by equilibrating octamethylcyclotetrasiloxane and (CH3)3SlO SiO units for every 20 units presnt, and the degree of polymerization should not exceed 100 units per molecule, preferably there being no more than 40 of such units per molecule.
- the degree of polymerization can be controlled by the amount of endblocking units that are present, e.g. [(CH SiO].
- the above copolymeric product is then reacted with one or more types of alpha olefin having an average of at least 14 carbon atoms per molecule, the reaction being in the presence of a platinum catalyst with heating to about 100 to 150 C.
- the product will be a copoly-mer of i t SltiO and Eli O 0 H3 C 113 where R is defined above. This is the silicone of this invention.
- Another method of making the silicones of this invention is to equilibrate octamethylcyclotetrasiloxane with CH3 CH3 RSlOSiR I13 CH3 in the presence of a catalyst such as NaOH.
- the above disiloxane can be made by reacting tetramethyldisiloxane with the appropriate alpha olefine in the presence of platinum.
- the products made by this partaicular process possess higher alkyl groups only on the terminal silicon atoms of each molecule.
- the fluid compositions of this invention can be applied to fibers by means of spraying, running the fibers over a pad soaked with the composition, or any other known Way of applying fluids to fibers.
- the waxy compositions of this invention can be applied by melteing the composition to the fluid form and then applying it, or by running the fibers across the waxy substance, etc.
- Any organic fiber can be used in this invention.
- any yarn or thread made of wool, cotton, rayon, hemp, silk, polypropylene, polyesters such as Dacron, polyamides such as nylon, polyethylene, or cellulose acetate is operative.
- the geratest improvements in lubricity tend to occur when cellulosic fibers such as cotton, or acrylic (polyacrylonitrile) fibers are used.
- Example 2 When a dispersion of 10 grams of E (CzaHuSlO (S10) CH3 2 (EH3 40 grams of paraffin, and grams of hexane is placed on a cotton thread and allowed to dry, the lubricity of the thread is greatly enhanced, and the heat stability of the lubricating coat is greater than that of a cotton fiber coated with paraffin alone.
- E CzaHuSlO (S10) CH3 2
- n has a value of 1 to 2, there being an average of 1 to 12 (b) units for every 20 (:1) units present, and there being an average of 4 to 100 (a) units present per polymer molecule, and (2) from 99 to 50 weight percent of a compatible diluent selected from the group consisting of nondrying organic oil and wax.
- a compatible diluent selected from the group consisting of nondrying organic oil and wax.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Lubricants (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41330464A | 1964-11-23 | 1964-11-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3423235A true US3423235A (en) | 1969-01-21 |
Family
ID=23636723
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US413304A Expired - Lifetime US3423235A (en) | 1964-11-23 | 1964-11-23 | Organosiloxane-containing finishes for organic fibers |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3423235A (is") |
| AT (1) | AT263691B (is") |
| CH (1) | CH470523A (is") |
| DE (1) | DE1469335A1 (is") |
| FR (1) | FR1452303A (is") |
| GB (1) | GB1097487A (is") |
| NL (2) | NL6515112A (is") |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3493425A (en) * | 1967-01-09 | 1970-02-03 | Dow Corning | Lubricated fibers |
| US3837022A (en) * | 1973-03-30 | 1974-09-24 | Phillips Petroleum Co | Fibers for pillow stuffing |
| US3844826A (en) * | 1971-12-16 | 1974-10-29 | Bayer Ag | Dressing sewing thread to reduced friction |
| US3853607A (en) * | 1973-10-18 | 1974-12-10 | Du Pont | Synthetic filaments coated with a lubricating finish |
| US3983272A (en) * | 1974-02-06 | 1976-09-28 | Wacker-Chemie Gmbh | Method for improving the lubricating properties and imparting antistatic properties to organic fibers |
| US4035550A (en) * | 1974-12-23 | 1977-07-12 | Massachusetts Institute Of Technology | Fiber reinforced composite of high fracture toughness |
| US4105569A (en) * | 1977-02-07 | 1978-08-08 | George A. Goulston Co., Ltd. | Yarn finish formulation |
| US4169905A (en) * | 1976-11-30 | 1979-10-02 | Rhone-Poulenc Industries | Process for lubricating textile threads |
| US4171267A (en) * | 1978-10-30 | 1979-10-16 | Sws Silicones Corporation | Organopolysiloxane-hydrocarbon oil solutions |
| US4394414A (en) * | 1981-05-29 | 1983-07-19 | Ppg Industries, Inc. | Aqueous sizing composition for glass fibers for use on chopped glass fibers |
| US4477524A (en) * | 1981-05-29 | 1984-10-16 | Ppg Industries, Inc. | Aqueous sizing composition for glass fibers for use on chopped glass fibers |
| US6051316A (en) * | 1995-06-09 | 2000-04-18 | Vetrotex France | Sizing composition for composite yarns and composite yarns coated with this composition |
| US20060280939A1 (en) * | 2003-12-24 | 2006-12-14 | Gale Pacific Limited | Polymeric plastics material and manufacture thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3436164A1 (de) * | 1984-10-03 | 1986-04-10 | Bayer Ag, 5090 Leverkusen | Schmieroelzubereitungen |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2486162A (en) * | 1942-02-26 | 1949-10-25 | Corning Glass Works | Organo-siloxanes |
| US2698817A (en) * | 1951-02-28 | 1955-01-04 | Coats & Clark | Sewing thread and method for producing same |
| US2735791A (en) * | 1953-08-05 | 1956-02-21 | Waterproofing compositions and their | |
| US2872356A (en) * | 1955-06-02 | 1959-02-03 | Dow Chemical Co | Lubrication of synthetic cellulose fibers |
| US3187752A (en) * | 1962-04-27 | 1965-06-08 | American Cyanamid Co | Non-absorbable silicone coated sutures and method of making |
-
0
- NL NL129267D patent/NL129267C/xx active
-
1964
- 1964-11-23 US US413304A patent/US3423235A/en not_active Expired - Lifetime
-
1965
- 1965-10-06 FR FR33883A patent/FR1452303A/fr not_active Expired
- 1965-10-13 CH CH1410165A patent/CH470523A/de not_active IP Right Cessation
- 1965-10-22 GB GB44869/65A patent/GB1097487A/en not_active Expired
- 1965-11-22 NL NL6515112A patent/NL6515112A/xx unknown
- 1965-11-22 AT AT1047965A patent/AT263691B/de active
- 1965-11-22 DE DE19651469335 patent/DE1469335A1/de not_active Withdrawn
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2486162A (en) * | 1942-02-26 | 1949-10-25 | Corning Glass Works | Organo-siloxanes |
| US2698817A (en) * | 1951-02-28 | 1955-01-04 | Coats & Clark | Sewing thread and method for producing same |
| US2735791A (en) * | 1953-08-05 | 1956-02-21 | Waterproofing compositions and their | |
| US2872356A (en) * | 1955-06-02 | 1959-02-03 | Dow Chemical Co | Lubrication of synthetic cellulose fibers |
| US3187752A (en) * | 1962-04-27 | 1965-06-08 | American Cyanamid Co | Non-absorbable silicone coated sutures and method of making |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3493425A (en) * | 1967-01-09 | 1970-02-03 | Dow Corning | Lubricated fibers |
| US3844826A (en) * | 1971-12-16 | 1974-10-29 | Bayer Ag | Dressing sewing thread to reduced friction |
| US3837022A (en) * | 1973-03-30 | 1974-09-24 | Phillips Petroleum Co | Fibers for pillow stuffing |
| US3853607A (en) * | 1973-10-18 | 1974-12-10 | Du Pont | Synthetic filaments coated with a lubricating finish |
| US3983272A (en) * | 1974-02-06 | 1976-09-28 | Wacker-Chemie Gmbh | Method for improving the lubricating properties and imparting antistatic properties to organic fibers |
| US4035550A (en) * | 1974-12-23 | 1977-07-12 | Massachusetts Institute Of Technology | Fiber reinforced composite of high fracture toughness |
| US4169905A (en) * | 1976-11-30 | 1979-10-02 | Rhone-Poulenc Industries | Process for lubricating textile threads |
| US4105569A (en) * | 1977-02-07 | 1978-08-08 | George A. Goulston Co., Ltd. | Yarn finish formulation |
| US4171267A (en) * | 1978-10-30 | 1979-10-16 | Sws Silicones Corporation | Organopolysiloxane-hydrocarbon oil solutions |
| US4394414A (en) * | 1981-05-29 | 1983-07-19 | Ppg Industries, Inc. | Aqueous sizing composition for glass fibers for use on chopped glass fibers |
| US4477524A (en) * | 1981-05-29 | 1984-10-16 | Ppg Industries, Inc. | Aqueous sizing composition for glass fibers for use on chopped glass fibers |
| US6051316A (en) * | 1995-06-09 | 2000-04-18 | Vetrotex France | Sizing composition for composite yarns and composite yarns coated with this composition |
| US20060280939A1 (en) * | 2003-12-24 | 2006-12-14 | Gale Pacific Limited | Polymeric plastics material and manufacture thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1452303A (fr) | 1966-02-25 |
| DE1469335A1 (de) | 1969-03-27 |
| CH1410165A4 (is") | 1968-12-13 |
| CH470523A (de) | 1969-05-14 |
| GB1097487A (en) | 1968-01-03 |
| NL6515112A (is") | 1966-05-24 |
| AT263691B (de) | 1968-07-25 |
| NL129267C (is") |
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