US2743193A - Treated cellulose organic acid ester fibers - Google Patents
Treated cellulose organic acid ester fibers Download PDFInfo
- Publication number
- US2743193A US2743193A US373455A US37345553A US2743193A US 2743193 A US2743193 A US 2743193A US 373455 A US373455 A US 373455A US 37345553 A US37345553 A US 37345553A US 2743193 A US2743193 A US 2743193A
- Authority
- US
- United States
- Prior art keywords
- fibers
- phosphoric acid
- alcohol
- morpholine
- cellulose acetate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000000835 fiber Substances 0.000 title claims description 32
- -1 organic acid ester Chemical class 0.000 title description 18
- 229920002678 cellulose Polymers 0.000 title description 14
- 239000001913 cellulose Substances 0.000 title description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 33
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 29
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 23
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 16
- 229920002301 cellulose acetate Polymers 0.000 claims description 11
- 239000002480 mineral oil Substances 0.000 claims description 11
- 235000010446 mineral oil Nutrition 0.000 claims description 11
- 229920001577 copolymer Polymers 0.000 claims description 8
- 238000005299 abrasion Methods 0.000 claims description 7
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 7
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 claims description 4
- 229940055577 oleyl alcohol Drugs 0.000 claims description 4
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 description 27
- 239000000314 lubricant Substances 0.000 description 13
- 229940081735 acetylcellulose Drugs 0.000 description 9
- 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 9
- 230000003750 conditioning effect Effects 0.000 description 8
- 150000002780 morpholines Chemical class 0.000 description 8
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 230000001050 lubricating effect Effects 0.000 description 7
- 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 7
- 150000001298 alcohols Chemical class 0.000 description 6
- 238000005461 lubrication Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 125000001117 oleyl 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])=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])[H] 0.000 description 6
- 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 6
- 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 6
- 229910000831 Steel Inorganic materials 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 230000005611 electricity Effects 0.000 description 5
- 230000003068 static effect Effects 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- 239000004753 textile Substances 0.000 description 5
- 108010010803 Gelatin Proteins 0.000 description 4
- 238000009960 carding Methods 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- TVACALAUIQMRDF-UHFFFAOYSA-N dodecyl dihydrogen phosphate Chemical class CCCCCCCCCCCCOP(O)(O)=O TVACALAUIQMRDF-UHFFFAOYSA-N 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 229910052573 porcelain Inorganic materials 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000004513 sizing Methods 0.000 description 4
- 238000009987 spinning Methods 0.000 description 4
- 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 3
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 3
- 229920006218 cellulose propionate Polymers 0.000 description 3
- 238000009940 knitting Methods 0.000 description 3
- 238000009941 weaving Methods 0.000 description 3
- 238000004804 winding Methods 0.000 description 3
- 229920008347 Cellulose acetate propionate Polymers 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- ZAMLGGRVTAXBHI-UHFFFAOYSA-N 3-(4-bromophenyl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(CC(O)=O)C1=CC=C(Br)C=C1 ZAMLGGRVTAXBHI-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical class [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VFEOWTNBQADBBD-UHFFFAOYSA-N morpholin-4-ium;phosphate Chemical class OP(O)(O)=O.C1COCCN1.C1COCCN1.C1COCCN1 VFEOWTNBQADBBD-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000007586 terpenes Nutrition 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
-
- 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 lubrication and conditioning of textile yarns and filaments, and more particularly to the lubrication and conditioning of textile yarns and filaments composed of organic derivatives of cellulose such as cellulose acetate, cellulose propionate, cellulose acetate-propio'nate, and cellulose acetate-butyrate, to render them amenable to a variety of textile operations such as warping, weaving, knitting, spinning, carding and the like.
- This invention has as its object to provide *lubricants which are applicable to treatment of both continuous filament yarns and cut staple fibers as said filaments emerge from the spinningca-binet in which theyare formed.
- a further object is to provide lubricants which are suitable for continuous filament yarn intended for warping, filling, and knitting.
- Another object is to provide lubricating and conditioning compositions which have antistatic characteristics, low kinetic friction, and low slip-stick friction.
- Another "object of this invention is to provide lubricants which promote superior bonding between the yarn and warp sizes such as gelatin and 'copolymers of maleic anhydride fand styrene which are commonly used in the trade.
- compositions which may be used to effectively lubricate filaments and fibers, both continuous filaments and cut staple. That is, textile material's maybe treated by 'the compositions to be described in detail herein, to render them more amenable to subsequent textile operations such as knitting, weaving, winding, card ing, opening, drafting, combing and other operations.
- One of the important components of our fibertreating composition comprises a .certainreaction product of long chain aliphatic alcohol partial esters of phosphoric acid.
- the preferred compound of :this class is illustrated 2,743,193 Patented Apr. 24, 1956 2 by the morpholine salt or salts of laul'yl phosphoric acid partial esters.
- fibers treated with lubricants containing compounds as just mentioned, and specifically compositions containing salts of morpholine and lauryl phosphoric acid partial esters, have unexpectedly high resistance to abrasion when sized with materials such as gelatin and copolymers of maleic 'anhydride and styrene which are commonly used in the trade. This is one of the novel features of our invention and is believed to be new and unobvious.
- the lauryl partial ester of phosphoric acid since the lauryl phosphoric acid salt of morpholine gives us the desired lubricating properties together with a satisfactory viscosity and color.
- the lauryl phosphoric acid salt of morpholine gives us the desired lubricating properties together with a satisfactory viscosity and color.
- most of the amine salts of the partial esters of long chain saturated aliphatic alcohols and phosphoric acid are either solids or waxy or gummy materials. We have found this to be a disadvantage in the use of these materials for the lubricating and conditioning of both continuous filament and staple fibers made from organic derivatives of cellulose.
- the morpholine salts of the partial esters of long chain saturated aliphatic alcohols and phosphoric acid are free flowing liquids. This is an unobvious fact and was disclosed to us through experimentation.
- No other amine salts such as monoethanolamine, diethanolarnine, triethanolamlne, diethylcyciohexylamine, ethylenediamine, or Z-amino-Z-methyll-propauol, of long chain saturated aliphatic alcohol phosphoric acid partial esters which we have examined have exhibited this property of being a free-flowing liquid.
- phosphates of long chain aliphatic alcohols exemplified by lauryl phosphate, which compounds may be purchased on the open market, may be satisfactorily used in the'present invention. It is possible, if desired, to purchase long chain aliphatic alcohol and phosphoric acid or other source of phosphorus radical and to make the partial ester therefrom. This may be accomplished by reacting the alcohol and phosphoric acid or other phosphor-us derivative together in the presence of a catalyst, "but such procedure is not required as a number of partial ester intermediates may be purchased cornmercially.
- the partial ester of phosphoric acid is either prepared or purchased. It is then reacted with morpholine, as will be described in detail hereinafter, to form the new salt which is used 'hereinin preparing 'fiber treating compositions.
- a lubricating and conditioning composition preferably is comprised of a partial ester of phosphoric acid with a long chain aliphatic alcohol, moiphol-ine, and a .long chain aliphatic alcohol together with mineral oil in suitable proportions.
- Our composition is thoroughly dispersed over the fibers in application thereto, and the fibers obtained are completely autistatic so that-a superior degree of lubrication and corn dition'ing is achieved.
- composition preferably comprises from 10-40 parts by weight of the partial ester of phosphoric acid with a long chain saturated aliphatic alcohol, 2-15 parts by weight of morpholine, 5-l5 parts by weight of fatty alcohols, and 40-70 parts by weight of mineral oil having a viscosity from 45-135. (Saybolt Universal seconds at F.)
- the components are preferably combined by adding the long chain saturated aliphatic alcohol phosphoric acid partial ester to the mineral oil with stirring, followed by the addition of morpholine, and the addition of the fatty alcohol.
- the long chain saturated aliphatic alcohol phosphoric acid partial ester to the mineral oil with stirring, followed by the addition of morpholine, and the addition of the fatty alcohol.
- saturated cyclic alcohols we have found it advantageous to add saturated cyclic alcohols.
- other emulsifiers such as terpene glycol ethers and fatty acid soaps serve as good dispersing agents for the morpholinium phosphates in mineral oil.
- a partial long chain aliphatic alcohol ester of phosphoric acid is either prepared or obtained, exemplified by the lauryl partial ester of phosphoric acid.
- This partial ester has the formula:
- the salt may be purified by various procedures as known to those skilled in the art.
- the preferred method is to purify the lauryl phosphoric acid partial ester and the morpholine before they are caused to react as described above.
- the morpholine salt of the partial long chain aliphatic alcohol ester of phosphoric acid is then formulated into the fiber treating compositions as already described above.
- Example I This cut staple was carded and spun into yarn and was found to process well in all operations.
- This lubricant which contributes to the satisfactory processing of cut staple to which it is applied is the low static electricity developed on the fibers. This is illustrated in the examples below comparing the static electricity on staple'fibers during carding, which have been lubricated with the composition above, with fibers lubricated with another type of lubricant, identified as oil A.
- the units are arbitrary.
- Example II The lubricating and conditioning composition described below was applied as a 25% aqueous emulsion to denier l9 filament bright yarn and was tested for its static electricity, kinetic friction over porcelain and steel surfaces, and slip-stick friction over a steel surface. The values were compared with those for a similar yarn treated with another lubricant, identified as oil B. The units are arbitrary.
- composition of the lubricant is as follows:
- Example III A lubricating and conditioning composition, which is described below, was applied to 75 denier 19 filament bright yarn and was tested for its static electricity, kinetic friction over porcelain and steel surfaces, and slip-stick friction over a steel surface. The values were compared with those for a similar yarn lubricated with another lubricant identified as oil C. The units are arbitrary.
- the lubricant was applied by means of an applicator roll as the filaments left the spinning cabinet.
- the composition might equally well have been applied at other stages of processing and in other operations such as twisting, winding, and reeling, or they might have been applied to cut staple fibers during any of the processes which are normal to the preparation of such fibers.
- the lubricant may be applied by passing the filaments over a roll, other devices which serve to deposit oil on filaments or fibers, such as by wick, spray, or both, may be used.
- lauryl alcohol represents the component of our preferredcompound
- other long chain alcohols exemplified by the'following alcohols: oleyl, myristyl,
- Treated cellulose acetate fibers which will exhibit high resistance to abrasion when sized with a sizing material exemplified by copolymers of maleic anhydride and styrene, said fibers being essentially comprised of cellulose-acetate, which fibers have applied thereto a treating composition containing a morpholine salt which is a free flowing liquid, said treating composition resulting from the following combination of materials: 25% partial ester of lauryl alcohol and phosphoric acid, 10% oleyl alcohol, 5-7% morpholine, and the major component mineral oil of a viscosity from 45-135 seconds Saybolt Universal at 100 F.
- Treated cellulose acetate fibers which will exhibit high resistance to abrasion when sized with a sizing material exemplified by copolymers of maleic anhydride and styrene, saidfibers being essentially comprised of cellulose acetate which. has applied thereto a treating composition containing a morpholine salt which is a free flowing liquid, said treating composition resulting from the following combination of materials: 10-40 parts by weight of lauryl alcohol partial ester of phosphoric acid, 2 parts by Weightof morpholine, 5-15 parts by weight of an alcohol from the group consisting of oleyl.
- Treated cellulose organic acid ester fibers from the group consisting of cellulose acetate, cellulose propionate, cellulose acetate propionate and cellulose acetate butyrate, which will exhibit high resistance to abrasion 6 when sized with a sizing material exemplified by copolymers of maleic anhydride and styrene, said fibers being essentially comprised of cellulose organic acid ester which has applied thereto a treating composition containing a morpholine salt which is a free flowing liquid, said treating composition resulting from the following combination of materials: l040 parts by weight of a partial ester of phosphoric acid with an alcohol from the group consisting of lauryl, oleyl, myristyl, cetyl and stearyl alcohols, 2-15 parts by weight of morpholine, 5-15 parts by weight of an'alcohol from the group consisting of oleyl, lauryl, cyclohexyl, myristyl, cetyl, ste
- Treated cellulose organic acid ester fibers from the group consisting of cellulose acetate, cellulose propionate, cellulose acetate propionate and cellulose acetate butyrate, which will exhibit high resistance to abrasion when sized with a sizing material exemplified by copolymers of maleic anhydride and styrene, said fibers being essentially comprised of cellulose organic acid ester which has applied thereto a treating composition containing a morpholine salt which is a free flowing liquid, said treating composition resulting from the following combination of materials: a major amount of mineral oil of a viscosity of 45-135 seconds Saybolt Universal at 100 F., 10-40 parts by weight of a partial ester of phosphoric acid with an alcohol from the group consisting of oleyl, lauryl, myristyl,- cetyl, and stearyl, 2-15 parts by weight of morpholine, 5-15 parts by weight of an alcohol fromthe group consisting of oleyl, lau
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
United States Patent TREATED CELLULOSE ORGANIC ACID ESTER FIBERS Raymond E. Donaldson and Charles Clayton White,
Kingsport, Tenn, assignor to Eastman Kodak Company, Rochester, N. Y., a corporation of New Jersey No Drawing. Application August 10, 1953, Serial No. 373,455
4 Claims. (Cl. 117-1395) This invention relates to the lubrication and conditioning of textile yarns and filaments, and more particularly to the lubrication and conditioning of textile yarns and filaments composed of organic derivatives of cellulose such as cellulose acetate, cellulose propionate, cellulose acetate-propio'nate, and cellulose acetate-butyrate, to render them amenable to a variety of textile operations such as warping, weaving, knitting, spinning, carding and the like.
As is well known in the manufacture of yarns, particularly those composed of cellulose organic derivatives, it is necessary to treat the yarn in order to reduce the tendency toward breakage of the individual filaments or fibers when they are subjected to various mechanical strains and to lubricate the yarn in 'order to facilitate handling in such operations as spinning, twisting, winding, reeling, warping, carding, drafting, combing, weaving, and other operations.
The lubrication of derivatives of cellulose, such as the cellulose esters, is a complex problem, and a diversity of materials has been employed to meet the demands or" such lubrication. To those skilled in the art, it is well known that while certain problems are common to the lubrication of continuous filament yarn and of staple fibers, each has its own peculiar problems.
After extended investigation, we have found a new chemical compound which may be formulated'wi'th other components to give a fiber treating composition which exhibits improved qualities over comparable compositions heretofore used in the art.
This invention has as its object to provide *lubricants which are applicable to treatment of both continuous filament yarns and cut staple fibers as said filaments emerge from the spinningca-binet in which theyare formed. A further object is to provide lubricants which are suitable for continuous filament yarn intended for warping, filling, and knitting. Another object is to provide lubricating and conditioning compositions which have antistatic characteristics, low kinetic friction, and low slip-stick friction. Another "object of this invention is to provide lubricants which promote superior bonding between the yarn and warp sizes such as gelatin and 'copolymers of maleic anhydride fand styrene which are commonly used in the trade.
We have found that certain derivatives of alcohol phosphates when incorporated into suitable mediums such as mineral oil together with the use of certain cosolvents provide compositions which may be used to effectively lubricate filaments and fibers, both continuous filaments and cut staple. That is, textile material's maybe treated by 'the compositions to be described in detail herein, to render them more amenable to subsequent textile operations such as knitting, weaving, winding, card ing, opening, drafting, combing and other operations.
One of the important components of our fibertreating composition comprises a .certainreaction product of long chain aliphatic alcohol partial esters of phosphoric acid. The preferred compound of :this class is illustrated 2,743,193 Patented Apr. 24, 1956 2 by the morpholine salt or salts of laul'yl phosphoric acid partial esters.
We have found that fibers treated with lubricants containing compounds as just mentioned, and specifically compositions containing salts of morpholine and lauryl phosphoric acid partial esters, have unexpectedly high resistance to abrasion when sized with materials such as gelatin and copolymers of maleic 'anhydride and styrene which are commonly used in the trade. This is one of the novel features of our invention and is believed to be new and unobvious.
We preferably use the lauryl partial ester of phosphoric acid, since the lauryl phosphoric acid salt of morpholine gives us the desired lubricating properties together with a satisfactory viscosity and color. We have found that most of the amine salts of the partial esters of long chain saturated aliphatic alcohols and phosphoric acid are either solids or waxy or gummy materials. We have found this to be a disadvantage in the use of these materials for the lubricating and conditioning of both continuous filament and staple fibers made from organic derivatives of cellulose. However, the morpholine salts of the partial esters of long chain saturated aliphatic alcohols and phosphoric acid are free flowing liquids. This is an unobvious fact and was disclosed to us through experimentation. No other amine salts, such as monoethanolamine, diethanolarnine, triethanolamlne, diethylcyciohexylamine, ethylenediamine, or Z-amino-Z-methyll-propauol, of long chain saturated aliphatic alcohol phosphoric acid partial esters which we have examined have exhibited this property of being a free-flowing liquid.
-' For use in preparing compositions described herein we have found that the phosphates of long chain aliphatic alcohols, exemplified by lauryl phosphate, which compounds may be purchased on the open market, may be satisfactorily used in the'present invention. It is possible, if desired, to purchase long chain aliphatic alcohol and phosphoric acid or other source of phosphorus radical and to make the partial ester therefrom. This may be accomplished by reacting the alcohol and phosphoric acid or other phosphor-us derivative together in the presence of a catalyst, "but such procedure is not required as a number of partial ester intermediates may be purchased cornmercially.
The partial ester of phosphoric acid is either prepared or purchased. It is then reacted with morpholine, as will be described in detail hereinafter, to form the new salt which is used 'hereinin preparing 'fiber treating compositions.
We 'h'ave'now found that staple fibers of both cellulose acetate or other organic derivatives of cellulosi'c materials, partially saponified :cellulose acetate or other partially saponified 'oitganicflesters of cellulose, may be satisfactorily lubricated and conditioned for spinning operations by the application thereto of =.a single application of a lubricating and conditioning composition. This composition preferably is comprised of a partial ester of phosphoric acid with a long chain aliphatic alcohol, moiphol-ine, and a .long chain aliphatic alcohol together with mineral oil in suitable proportions. Our composition is thoroughly dispersed over the fibers in application thereto, and the fibers obtained are completely autistatic so that-a superior degree of lubrication and corn dition'ing is achieved.
Our JIIGVC]. composition preferably comprises from 10-40 parts by weight of the partial ester of phosphoric acid with a long chain saturated aliphatic alcohol, 2-15 parts by weight of morpholine, 5-l5 parts by weight of fatty alcohols, and 40-70 parts by weight of mineral oil having a viscosity from 45-135. (Saybolt Universal seconds at F.)
, In forming said lubricating and conditioning compositions the components are preferably combined by adding the long chain saturated aliphatic alcohol phosphoric acid partial ester to the mineral oil with stirring, followed by the addition of morpholine, and the addition of the fatty alcohol. In some of our compositions, as shown in the examples, we have found it advantageous to add saturated cyclic alcohols. Also, we have found that other emulsifiers such as terpene glycol ethers and fatty acid soaps serve as good dispersing agents for the morpholinium phosphates in mineral oil. After the components are mixed, gentle agitation is continued until a smooth, homogeneous blend is obtained.
In further detail, a partial long chain aliphatic alcohol ester of phosphoric acid is either prepared or obtained, exemplified by the lauryl partial ester of phosphoric acid. This partial ester has the formula:
The partial ester if desired can be reacted with morpholine as follows:
If desired, the salt may be purified by various procedures as known to those skilled in the art. The preferred method is to purify the lauryl phosphoric acid partial ester and the morpholine before they are caused to react as described above.
The morpholine salt of the partial long chain aliphatic alcohol ester of phosphoric acid is then formulated into the fiber treating compositions as already described above.
Example I This cut staple was carded and spun into yarn and was found to process well in all operations. One of the important characteristics of this lubricant which contributes to the satisfactory processing of cut staple to which it is applied is the low static electricity developed on the fibers. This is illustrated in the examples below comparing the static electricity on staple'fibers during carding, which have been lubricated with the composition above, with fibers lubricated with another type of lubricant, identified as oil A. The units are arbitrary.
Example II The lubricating and conditioning composition described below was applied as a 25% aqueous emulsion to denier l9 filament bright yarn and was tested for its static electricity, kinetic friction over porcelain and steel surfaces, and slip-stick friction over a steel surface. The values were compared with those for a similar yarn treated with another lubricant, identified as oil B. The units are arbitrary.
Instant Lubricant B Percent Lubricant on Yarn 2. 38 3.02 Static Electricity:
Porcelain Surface +1 6 Steel Surface-.- +1 -8 Kinetic Friction:
Porcelain Surface 23 27 24 30 Slip-Stick Friction 17 26 Abrasion Resistance of Gelatin Sized Yarn 7O 49 The composition of the lubricant is as follows:
Per cent Mineral oil 58.0 Partial ester of lauryl alcohol and phosphoric acid 25.0 Oleyl alcohol 10.0 Morpholine 7.0
Example III A lubricating and conditioning composition, which is described below, was applied to 75 denier 19 filament bright yarn and was tested for its static electricity, kinetic friction over porcelain and steel surfaces, and slip-stick friction over a steel surface. The values were compared with those for a similar yarn lubricated with another lubricant identified as oil C. The units are arbitrary.
Partial ester of lauryl alcohol and phosphoric acid 25.0
Lauryl alcohol 8.0 Cyclohexyl alcohol 6.0 Morpholine 7.0
Although we have indicated in the above examples certain percentages of oil applied to filaments foruse as cut staple fibers, or continuous filament yarns, our invention is in no way restricted to these values, nor are the electrical and physical properties given here changed greatly if the oil content on the filaments is altered over wide ranges.
In the examples stated above, we have indicated that the lubricant was applied by means of an applicator roll as the filaments left the spinning cabinet. However, the composition might equally well have been applied at other stages of processing and in other operations such as twisting, winding, and reeling, or they might have been applied to cut staple fibers during any of the processes which are normal to the preparation of such fibers. Also, although we have indicated that the lubricant may be applied by passing the filaments over a roll, other devices which serve to deposit oil on filaments or fibers, such as by wick, spray, or both, may be used.
While in the foregoing disclosure we have specifically referred to lauryl alcohol as this represents the component of our preferredcompound, it is possible to use other long chain alcohols in preparing the partial ester, exemplified by the'following alcohols: oleyl, myristyl,
cetyl, stearyl, etc. Or, it is possible to use mixed alcohols to form the partial mixed ester.
In place of oleyl alcohol we may use lauryl, cyclohexyl, myristyl, cetyl, stearyl, linolyl, ricinolyl, or mixtures of these. Other changes may be made in our process and product as exemplified by the following: In place of gelatin or copolymers of maleic anhydride and styrene other sizes may be used such as polyvinyl alcohol or substituted acrylamides.
While the foregoing illustrates certain of the broader aspects of our invention for the treatment of, cellulose ester yarn as already described above in detail, we prefer to use the morpholine salt of the lauryl partial ester of phosphoric acid inasmuch as certain additional advantages and improvements are obtained which are not obtainable by other compounds.
We claim: 7 v
l. Treated cellulose acetate fibers which will exhibit high resistance to abrasion when sized with a sizing material exemplified by copolymers of maleic anhydride and styrene, said fibers being essentially comprised of cellulose-acetate, which fibers have applied thereto a treating composition containing a morpholine salt which is a free flowing liquid, said treating composition resulting from the following combination of materials: 25% partial ester of lauryl alcohol and phosphoric acid, 10% oleyl alcohol, 5-7% morpholine, and the major component mineral oil of a viscosity from 45-135 seconds Saybolt Universal at 100 F.
2. Treated cellulose acetate fibers which will exhibit high resistance to abrasion when sized with a sizing material exemplified by copolymers of maleic anhydride and styrene, saidfibers being essentially comprised of cellulose acetate which. has applied thereto a treating composition containing a morpholine salt which is a free flowing liquid, said treating composition resulting from the following combination of materials: 10-40 parts by weight of lauryl alcohol partial ester of phosphoric acid, 2 parts by Weightof morpholine, 5-15 parts by weight of an alcohol from the group consisting of oleyl. lauryl, cyclohexyl, myristyl, cetyl, stearyl, linolyl and ricinolyl alcohols and 40-70 parts by weight of mineral oil of a viscosity of45-135 seconds Saybolt Universal at 100 F.
3. Treated cellulose organic acid ester fibers from the group consisting of cellulose acetate, cellulose propionate, cellulose acetate propionate and cellulose acetate butyrate, which will exhibit high resistance to abrasion 6 when sized with a sizing material exemplified by copolymers of maleic anhydride and styrene, said fibers being essentially comprised of cellulose organic acid ester which has applied thereto a treating composition containing a morpholine salt which is a free flowing liquid, said treating composition resulting from the following combination of materials: l040 parts by weight of a partial ester of phosphoric acid with an alcohol from the group consisting of lauryl, oleyl, myristyl, cetyl and stearyl alcohols, 2-15 parts by weight of morpholine, 5-15 parts by weight of an'alcohol from the group consisting of oleyl, lauryl, cyclohexyl, myristyl, cetyl, stearyl, linolyl and ricinolyl alcohols, and 40-70 parts by weight of mineral oil of a viscosity of 45-135 seconds Saybolt Universal at F. i g
4. Treated cellulose organic acid ester fibers from the group consisting of cellulose acetate, cellulose propionate, cellulose acetate propionate and cellulose acetate butyrate, which will exhibit high resistance to abrasion when sized with a sizing material exemplified by copolymers of maleic anhydride and styrene, said fibers being essentially comprised of cellulose organic acid ester which has applied thereto a treating composition containing a morpholine salt which is a free flowing liquid, said treating composition resulting from the following combination of materials: a major amount of mineral oil of a viscosity of 45-135 seconds Saybolt Universal at 100 F., 10-40 parts by weight of a partial ester of phosphoric acid with an alcohol from the group consisting of oleyl, lauryl, myristyl,- cetyl, and stearyl, 2-15 parts by weight of morpholine, 5-15 parts by weight of an alcohol fromthe group consisting of oleyl, lauryl, cyclohexyl, myristyl, cetyl, stearyl, linolyl and ricinolyl alcohols, and wherein the last-mentioned alcohol is different from the alcohol radical in the said partial ester.
References Cited in the file of this patent UNITEDSTATES PATENTS
Claims (1)
1. TREATED CELLULOSE ACETATE FIBERS WHICH WILL EXHIBIT HIGH RESISTANCE TO ABRASION WHEN SIZED WITH A SIZING MATERIAL EXEMPLIFIED BY COPOLYMERS OF MALEIC ANHYDRIDE AND STYRENE, SAID FIBERS BEING ESSENTIALLY COMPRISED OF CELLULOSE ACETATE, WHICH FIBERS HAVE APPLIED THERETO A TREATING COMPOSITION CONTAINING A MORPHOLINE SALT WHICH IS A FREE FLOWING LIQUID, SAID TREATING COMPOSITION RESULTING FROM THE FOLLOWING COMBINATION OF MATERIALS: 25% PARTIAL ESTER OF LAURYL ALCOHOL AND PHOSPHORIC ACID, 10% OLEYL ALCOHOL, 5-7% MORPHOLINE, AND THE MAJOR COMPONENT MINERAL OIL OF A VISCOSITY FROM 45-135 SECONDS SAYBOLT UNIVERSAL AT 100* F.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US373455A US2743193A (en) | 1953-08-10 | 1953-08-10 | Treated cellulose organic acid ester fibers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US373455A US2743193A (en) | 1953-08-10 | 1953-08-10 | Treated cellulose organic acid ester fibers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2743193A true US2743193A (en) | 1956-04-24 |
Family
ID=23472490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US373455A Expired - Lifetime US2743193A (en) | 1953-08-10 | 1953-08-10 | Treated cellulose organic acid ester fibers |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2743193A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2872351A (en) * | 1953-11-14 | 1959-02-03 | Bohme Fettchemie Gmbh | Compositions for and methods of finishing textile materials |
| US3242074A (en) * | 1963-03-22 | 1966-03-22 | Eastman Kodak Co | Fiber treating compositions and fibers treated therewith |
| US3245905A (en) * | 1962-10-09 | 1966-04-12 | Eastman Kodak Co | Blended fibers having improved antistatic properties |
| US3267189A (en) * | 1959-11-03 | 1966-08-16 | Celanese Corp | Wet spinning of cellulose triesters |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2005619A (en) * | 1934-11-10 | 1935-06-18 | Du Pont | Esters of acids of phosphorus |
| US2047398A (en) * | 1930-06-26 | 1936-07-14 | Ig Farbenindustrie Ag | Artificial resins and process of making them |
| US2186628A (en) * | 1937-11-26 | 1940-01-09 | Eastman Kodak Co | Yarn conditioning process and composition therefor |
| US2196753A (en) * | 1938-12-17 | 1940-04-09 | Eastman Kodak Co | Yarn conditioning process |
| US2385423A (en) * | 1942-10-03 | 1945-09-25 | Celanese Corp | Treatment of textile materials |
| US2480056A (en) * | 1946-01-11 | 1949-08-23 | Gulf Oil Corp | Heterocyclic nitrogen base salts of 3-methyl-butyl, 2-ethyl-hexyl orthophosphate |
| US2498408A (en) * | 1945-12-06 | 1950-02-21 | Gen Aniline & Film Corp | Antistatic textile materials |
| US2563506A (en) * | 1951-08-07 | Quaternary ammonium salts of | ||
| US2609350A (en) * | 1946-12-21 | 1952-09-02 | Gen Aniline & Film Corp | Textile finishing agent |
| US2616867A (en) * | 1950-08-30 | 1952-11-04 | Monsanto Chemicals | Composition for and method of sizing yarns |
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1953
- 1953-08-10 US US373455A patent/US2743193A/en not_active Expired - Lifetime
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2563506A (en) * | 1951-08-07 | Quaternary ammonium salts of | ||
| US2047398A (en) * | 1930-06-26 | 1936-07-14 | Ig Farbenindustrie Ag | Artificial resins and process of making them |
| US2005619A (en) * | 1934-11-10 | 1935-06-18 | Du Pont | Esters of acids of phosphorus |
| US2186628A (en) * | 1937-11-26 | 1940-01-09 | Eastman Kodak Co | Yarn conditioning process and composition therefor |
| US2196753A (en) * | 1938-12-17 | 1940-04-09 | Eastman Kodak Co | Yarn conditioning process |
| US2385423A (en) * | 1942-10-03 | 1945-09-25 | Celanese Corp | Treatment of textile materials |
| US2498408A (en) * | 1945-12-06 | 1950-02-21 | Gen Aniline & Film Corp | Antistatic textile materials |
| US2480056A (en) * | 1946-01-11 | 1949-08-23 | Gulf Oil Corp | Heterocyclic nitrogen base salts of 3-methyl-butyl, 2-ethyl-hexyl orthophosphate |
| US2609350A (en) * | 1946-12-21 | 1952-09-02 | Gen Aniline & Film Corp | Textile finishing agent |
| US2616867A (en) * | 1950-08-30 | 1952-11-04 | Monsanto Chemicals | Composition for and method of sizing yarns |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2872351A (en) * | 1953-11-14 | 1959-02-03 | Bohme Fettchemie Gmbh | Compositions for and methods of finishing textile materials |
| US3267189A (en) * | 1959-11-03 | 1966-08-16 | Celanese Corp | Wet spinning of cellulose triesters |
| US3245905A (en) * | 1962-10-09 | 1966-04-12 | Eastman Kodak Co | Blended fibers having improved antistatic properties |
| US3242074A (en) * | 1963-03-22 | 1966-03-22 | Eastman Kodak Co | Fiber treating compositions and fibers treated therewith |
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