US2345734A - Self-emulsifying phosphated and phosphited oils as antistatic lubricants - Google Patents
Self-emulsifying phosphated and phosphited oils as antistatic lubricants Download PDFInfo
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- US2345734A US2345734A US285208A US28520839A US2345734A US 2345734 A US2345734 A US 2345734A US 285208 A US285208 A US 285208A US 28520839 A US28520839 A US 28520839A US 2345734 A US2345734 A US 2345734A
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
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- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S260/00—Chemistry of carbon compounds
- Y10S260/15—Antistatic agents not otherwise provided for
-
- 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
- Y10T428/2904—Staple length fiber
- Y10T428/2907—Staple length fiber with coating or impregnation
Definitions
- This invention relates to the preparation and use of dispersing agents in the compounding of compositions adapted for the lubrication and other treatment of filaments and yarns composed of or containing organic derivatives of cellulose such as cellulose acetate, cellulose propionate, cellulose acetate propionate and cellulose acetate butyrate.
- This invention has as its principal object to provide a new class of self-dispersible compounds which are particularly adapted for use as emulsiflers for textile yarn lubricants, as textile lubricants as such, and as deelectrifying or anti-static agents.
- a further object is to provide yarn lubrihydroxylated or unblown oils, fats, and waxes, such as castor oil, cod liver oil, rapeseed oil, carnauba wax and Japan wax with a phosphating agent such as phosphoric acid and the various pyro-phosphoric acids, thio-phosphoric acids and the corresponding pyro acids, phosphorus pentoxide, phosphorus pentasulilde, phosphorus pentachloride, phosphorus oxychloride, phosphorus thiochloride and the like, or with a phosphiting agent such as phosphorus acid, phosphorus trichloride, phosphorus oxide, P(OH) 2C1, P(OH) C12, PClz-NH: and the like-self-dispersible compounds which are excellent emulsifiers for textile lubricants and also good lubricants in and of themselves, may be produced.
- a phosphating agent such as phosphoric acid and the various pyro-
- phosphoric acid is probably the least eflicacious.
- the highly hydroxylated oils such as castor oil and cod liver ,oil are outstanding in their ability togive phosphated and .phosphited compounds capable of acting as surface active, de-electrifying, emulsifying, and lubricating agents in accordance with our invention.
- oils within the contemplation of our invention are composed of or contain compounds having at least one free hydroxyl group or its equivalent, in its molecule which is subject to phosphation or phosphition.
- oils those resulting from the phosphation or phosphition of vegetable, animal and marine oils having an iodine value between and 100, and the organic and inorganic base salts of these phosphated and phosphited oils, are of exceptional value as surface-active, deelectrifying, emulsifying, and lubricating agents.
- phosphated oils of our invention those which have proved outstanding in actual practice are phosphated blown neats-foot, phosphated blown olive and phosphated blown castor oil's.
- phosphated unblown or hydroxylated oils phosphated castor and cod liver oils are outstanding.
- these phosphated and phosphited blown and unblown oils and in par ticular the inorganic and organic base salts of phosphated and phosphited blown oils having an iodine number of 50-100 are especially effective in the compounding of compositions adapted for the lubrication and other treatment of yarns composed of or containing organic derivatives of cellulose, such as cellulose acetate, since, not only are they excellent dispersing or emulsifying agents for the textile lubricants commonly employed in such compounds, for example, neat'sroot, olive, and light mineral oils, but also are themselves selt-emulsifiable oils which may be used as the primary lubricant in such compositions.
- phosphated and phosphited oils are also excellent de-electriiying or anti-static agents and may also be used as'vehiclesfor fugitive dyes and as dye assistants in the permanent dyeing or various types of textile fabrics includ- Pnosrna'ran COMPOUNDS
- Example 1 37 gm. of castor oil are added to 6 gm. of PO Cla in pyridine. The reaction is completed by warming. The product is filtered, washed with aqueous bicarbonate, and neutralized. The reaction product is a seli-dispersible, cloudy, brown oil.
- Example 2 200 gm. of rapseseed oil are warmed with 25 gm. of
- Example 3 Carnauba wax and crystalline phosphoric acid are heated in a molecular proportion of. 1:1 on the steam bath for 24-60 hr.
- the product after neutralization with asuitable base such as diethylcyolohexylamine, triethanolamine, tetra-- ethylammonium hydroxide, ditetrahydroiurfurylamine, etc., is a selt-dispersible, gelatinous dark oil.
- a suitable base such as diethylcyolohexylamine, triethanolamine, tetra-- ethylammonium hydroxide, ditetrahydroiurfurylamine, etc.
- Example 4 g A mixture of '75 gm. of castor oil and 25 gm. of carnauba wax is treated with 75 gm. of ethylene glycol and 20 gm. of P205. The reaction product is neutralized with 90% triethanolamine. The heavy brown 011 obtained is self-emulsifiable in water.
- Example 5 100 gm. of reduced and partially acetylated castor oil are heated with 60 gm. oi sirupy phosphoric acid and 20 gm. of P205 for hr. at 60.
- the neutralized product is an oily solid.
- Example 6 200 gm. of Japan wax are heated with 250 gm. of PS0]: (NHCnHas) and 50 gm. of Cellulosolve for 10 hr. in 1 liter of C014. The reaction is completed by removing the HCl and 0014 in vacuo. The product is a low melting waxy solid.
- Example 7 100 gm. of castor oil are heatedin vacuo at 180 with 100 gm. of anhydrous NazHP04, using glycerine as a solvent. The reaction product is washed with a small quantity of water, leaving a slippery waxy powder.
- Example 9 100 gm. of phosphated carnauba wax are added to 900 gm. of olive oil and 10 kg. of water. This emulsion is then applied to threads of cellulose and its derivatives to assist in processing operations such as weaving, spinning and knitting.
- Example 10 1 lb. of the neutralized product of the reaction between castor oil, P205 and ethylene glycol is added to 10 lb. of neats-foot oil and the mixture applied to threads and filaments of cellulose and its organic derivatives such as cellulose acetate, to reduc friction in processing operations.
- Example 11 5% of a neutralized phosphated castor oil prepared as described above is added to the common lubricants such as mineral oils, vegetable oils and blown oils to produce stabl emulsions of the latter to facilitate their application to filaments and threads of cellulose and its derivatives, and their removal therefrom.
- common lubricants such as mineral oils, vegetable oils and blown oils
- Example 12 3-10% by weight of the neutral reaction product obtained in Example 6 is applied by means of a wick, roll, or spray to threads or filaments of cellulose and its derivatives, to assist in textile processing operations.
- Example 13 10% of the neutral reaction product between castor oil, cetyl alcohol and POCls worked up as previously described is applied to knitting yarn to reduce friction and electrification.
- Example 14 Mixtures of any of the phosphated oils prepared above or similar ones are added to oils such as neats-foot and applied to leather and leather substitutes to give softness and line handle.
- Example 15 100 gm. of reduced rapeseed oil are treated with 20 gm.of
- Example 16 I 50 gm. of reduced'castor oil are treated with in benzene and the HCl formed and benzene removed in vacuo. The reaction product is a lowmelting waxy solid.
- Example 17 100 gms. of unblown castor oil are heated with 40 grains of euro-r m):
- Example 18 100 gm. of oxidized neats-foot oil are heated with '70 gm. of 75% phosphoric acid at 60 for 8 hr. and the product washed with water several times and dried. The orange, viscous oil produced is soluble in water when neutralized with a base.
- Example 20 50 gm. of oxidized olive oil are treated in the cold with 10 gm. of phosphorus pentoxide and 2 cc. of water. The reaction product is well washed with water and dried. The clear thick oil obtained is soluble in a :basic solution.
- Example 21 35 gm. of blown sperm oil are heated at 95 for 4 hr. with 10 gm. of sirupy phosphoric acid and 0.1 gm. of concentrated sulfuric acid. The heavy oily product is washed with water, dried under reduced pressure, and neutralized.
- Example 22 500 gm. of blown rapeseed oil are treated with one equivalent of in benzene and then warmed. The hydrochloric acid and benzene are removed under reduced pressure. The reaction product is hydrolyzed with dilute sodium bicarbonate. The acid phosphate may be neutralized with a base such as ditetrahydrofurfurylamine or diethylcylohexylamine to give a water-soluble compound.
- a base such as ditetrahydrofurfurylamine or diethylcylohexylamine
- Example 23 200 gm. of blown Japan wax are warmed with 50 gm. of C11H35OPOC12 in chloroform. The chloroform and hydrochloric acid are distilled of! under reduced pressure. The product is hydrolyzed and then neutralized with triethanolmine. It is a thick, yellow-brown, self-dispersible oil.
- Example 24 A mixture of 33 gm. of blown teaseed oil, 88 gm. blown rapeseed oil, and 33 gm. blown peanut oil is treated with 140 gm. of PSClflNH-Cufia) in carbon tetrachloride and the reaction product worked up as previously described. The oil obtained is seli-emulsiflable, stable to heat, and very viscous.
- Example 25 A mixture of gm. of blown neats-foot oil-and 25 gm. of blowncarnauba wax is treated with 75 gm. of ethylene glycol and 20 gm. of phosphorus pentoxide. The reaction product is washed. dried, and neutralized. The semi-solid waxy material is fairly soluble in water.
- Example 26 100 gm. of oxidized olive oil with a high acetyl value are treated with 10 gm. phosphorus pen-toxide and 50 gm. methyl Cellosolve. The reaction product is neutralized with ditetrahydrofurfurylamine. The product is a resinous brown oil, fairly soluble in water.
- Emmple 27 100 rm. of neats-foot oil are blown in the presence of 20 gm. of sirupy phosphoric acid at 100 for 10 hr. The resulting product is water-soluble and resembles that obtained in Example 19.
- Example 28 A mixture consisting of 50 ounces castor oil and 50 ounces .blown kapok seed oil is heated with 20 ounces of phosphoric acid and 6.7 ounces of phosphoric anhydride for 4 hr. The product is washed, dried and neutralized. It is a gelatinous, water-soluble oil.
- Example 29 100 gm. of castor oil are heated with 60 gm. crystalline phosphoric acid until a jell is formed. The product is melted, washed with hot water and neutralized with an organic or inorganic base.
- Example 30 100 gm. of blown and reduced neat's-foot oil are heated 10 hr. with 100 gm. of 75% mmphosphoric acid. The product is washed and neutralized.
- Example 31 To -5 lb. of an anthraquinone dye are added 2 lb. of phosphated blown castor which has been previously almost completely neutralized, and the mixture is poured into water heated to 200 lb. of textile material in the form of thread or cloth are then dipped and dyed.
- Example 32 1 lb. of a phosphated oxidized neats-foot oil prepared as described above is added to 10 lb. of olive oil and 80 lb. of water. The emulsion is then applied to threads of cellulose and its derivatives to assist in processing operations such as weaving, spinning, etc.
- Example 33 1 lb. of the neutralized product of the reaction between blown castor oil, phosphoric anhydride, and ethylene glycol is added to 10 lb. of neats-foot oil and the mixture applied to threads of cellulose and its derivatives, especially cellulose acetate, to reduce friction in processln'g operations.
- Example 34 by weight of a. neutralized phosphated castor oil-blown rapeseed oil mixture is added to the common lubricants such as mineral oil, vegetable oils, and blown oils to produce stable emulsions of the latter and facilitate their application to filaments and threads of cellulose and its derivatives, as well as to facilitate the removal of these oils therefrom.
- common lubricants such as mineral oil, vegetable oils, and blown oils
- Example 35 1-5% of the neutral reaction product of blown olive oil, phosphorus oxychloride and Cellosolve is applied in the usual way to threads or filaments of cellulose and its derivatives to aid in textile processing operations.
- Example 36 85% of the neutral reaction product between castor oil, blown rapeseed 'oil and blown sesame oil is mixed with of a softener such as glyce'ryl acetals, Cellosolve formal, glycols and polyglycols and ethers thereof. The mixture is applied to threads of cellulose and its derivatives to facilitate knitting operations.
- a softener such as glyce'ryl acetals, Cellosolve formal, glycols and polyglycols and ethers thereof.
- Example 37 Mixtures of any of the phosphates prepared above with oils such neats-foot oil are: applied to leather to give softness and a fine handle.
- Example 38 10% of the neutral product of the reaction between blown carnauba wax, POC12(OC17H35), and cetyl alcohol isdissolved together with cellulose acetate stearate and of a common plasticizer such as butyl or any phthalate, triphenyl phosphate, Cellosolve phthalate, etc. in a suitable solvent to produce a plastic of good strength, elasticity and appearance.
- a common plasticizer such as butyl or any phthalate, triphenyl phosphate, Cellosolve phthalate, etc.
- Example 39 1% of a slightly acid phosphated oxidized castor oil is added to soap which is to be used in hardwater.
- Example 40 A fugitive tint solution is prepared for ap plication to textile threads, particularly of cellulose acetate, having the following composition:
- the emulsion is applied to the yarn by any suitable means such as a spray, wick, or roller and may be dried if desired.
- Example 41 Grams Phosphated blown castor oil triethanol- Pnosrm'rsn COMPOUNDS
- Example 43 37 g. of castor oil are added to 6 g. phosphorus trichloride in pyridine. The reaction is completed by warming. The product is filtered, treated with aqueous sodium carbonate. The reaction product is self dispersible in water.
- Example 44 200 g. of rapeseed oil are warmed with g.
- Example 45 Carnauba wax and phosphorus trioxide are heated in a molecular proportion of 1:1 on the steam bath for 24-60 hours.
- the product after neutralization with a suitable base such as diethylcyclohexylamine, ditetrahydrofurfurylamine,
- ethanolamine, etc. is self-dispersible in water.
- Example 46 A mixture of 75 g. castor oil and 25 g. carnauba wax is treated with g. phosphorus trioxide. The reaction product is neutralized with triethanolamine. The heavy brown oil forms an aqueous dispersion.
- Example 47 a 100 g. of reduced partly acetylated castor oil are treated at till-100 for 10 hours with 60 g. phosphorus acid and 30 g. phosphorus trisulfide. The product is neutralized with tetramethylammonium hydroxide. The product forms an aqueous suspension.
- Example 48 200 g. Japan wax are treated with 200 g.
- Example 49 100 g. blown castor oil are heated with 25 g. phosphorus acid at 110-115 for 5 hours with stirring. The product is then neutralized with triethanolamine and is soluble in warm water. In place of blown castor oil, we may use blown neats-foot, sperm, olive, teaseed, soya bean, rape-- seed, com, menhaden, carnauba, Japan wax, etc.
- Example 50 100 g. blown neats-foot oil are heated with 50 g. phosphorus acid as in Example 49 and the product is then' treated in pyridine with 20 g. phosphorus trichloride. The reaction product is poured into dilute sodium hydroxide.
- Example 51 g. blown castor oil are reacted with 75 g. phosphorus acid as in Example 49 and then in pyridine with 20 g. phosphorus oxychloride.
- diethylcyclohexylamine salt is made in the usual manner.
- the product is water soluble.
- Example 52v 100 g. blown sperm oil are heated with a mixture of 40 g. phosphorus acid and 30 g. phosphoric acid at 96-120 for 4 hours.
- the trimethylbenzyl ammonium hydroxide salt is water soluble.
- Example 54 A mixture 01' 50 g. blown soya bean oil and 50 g. blown teaseed oil is reacted with 70 g. phosphorus acid as above and neutralized with a mixture oi potassium hydroxide and dibutylamine.
- Example 55 5 pounds -1,4-dimethylamino anthraquinone are finely ground with 2 pounds 01' the sodium salt of phosphited blown olive oil and poured into water heated to 85. 200 pounds of cellulose acetate knit fabric are entered and dyed blue.
- Example 56 1 pound of a phosphited oxidized neats-foot oil is added to pounds olive oil and 80 pounds water. The emulsion is then appliedto threads of cellulose or its derivatives to assist in weaving, knitting, etc.
- Example 57 fats, or waxes of our invention may be employed with a high degree of effectiveness as emulsifying, wetting out and deelectrifying agents in the compounding of yarn treating compositions.
- Various ingredients such as other lubricating agents, solvents, non-solvents, blending agents and the like may be employed in connection with these compounds within the scope of our invention.
- various dyes or other coloring matter may be employed in case it is desired to permanently or fugitively tint or dye the mate-' rial undergoing treatment.
- compositions containing specific percentages of the various ingredients may vary widely depending upon the particular purpose for which the composition is intended.
- emulsions particularly adapted for the treatment of yarns composed of organic derivatives of cellulose such as cellulose acetate
- the broad scope of our invention includes the preparation of emulsions adapted for the treatment of many other types of cellulose derivative yarns such as those composed of or containing cellulose propionate, cellulose butyrate, cellulose acetate propionate, cellulose acetate butyrate, ethyl cellulose, methyl cellulose, benzyl cellulose and others, as well as to the conditioning of silk, wool, cotton, viscose and other natural or artificial materials.
- yarn as used herein and in the claims is to be understood as including a single filament, a plurality of filaments associated into the form of a thread, either of high or low twist, single or'multiple threads associated or twisted together, composite threads composed of a mix ture of natural and artificial filaments or a composite thread formed by twisting together indivldual strands of natural or artificial materials, as well as cut staple fibers produced from natural and/or artificial filaments or threads and spun yarn produced from such staple fibers.
- the process of simultaneously lubricating and eliminating the tendency of yarns, filaments or fibers composed of or containing organic de- 'rivatives of cellulose to accumulate charges of static electricity which comprises applying thereto a composition containing a its essential lubricating and anti-static component an oil which is the product of reaction obtained by first blowing an oil containing compounds having a certain degree of unsaturation to produce compounds having at least one free hydroxyl group or its equivalent in its molecule which is subject to phosphation or phosphition, and then reacting the blown oil with an agent selected from the group consisting of phosphating and phosphiting agents.
- the process of simultaneously lubricating and eliminating the tendency of yarns, filaments or fibers composed of or containing organic derivatives of cellulose to accumulate charges of static electricity which comprises applying thereto a composition containing as its essential lubricating and anti-static component a phosphated oil which is the product of reaction obtained by first blowing an oil containing compounds having a certain degree of unsaturation to produce compounds having at least one free hydroxyl group or its equivalent in its molecule which is subject to phosphation, and then reacting the blown oil with a phosphating agent.
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Description
Patented Apr. '4, 1944 SELF-EMULSIFYING PHOSPHATE!) AND PHOSPHITED OILS AS ANTISTATIC LU- BBICAN TS Joseph B. Dickey and James G. McNally, Rochester, N. Y., asslgnors to Eastman Kodak Com- Y., a corporation of New pany, Rochester, N.
Jersey No Drawing. Application July 18, 1939, Serial No. 285,208
7 Claims. ('Cl. 8-1425) This invention relates to the preparation and use of dispersing agents in the compounding of compositions adapted for the lubrication and other treatment of filaments and yarns composed of or containing organic derivatives of cellulose such as cellulose acetate, cellulose propionate, cellulose acetate propionate and cellulose acetate butyrate.
As is well known in the manufacture of yarns, particularly those composed. of or containing 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 and reeling. It is also necessary to treat yarn to adapt it for use as warp or filling or for the manufacture of various types of knitted fabrics. In knitting, it is particularly important that the yarn be soft and pliable in order that it may conform readily to the contour of the needles and thus produce a closely knit. fabric free from such defects as stitch distortion, "pin holes," laddering, and the like.
In the preparation of compositions for this purpose it is customary to employ as emulsifying agents metallic and organic soaps and water-soluble soaps or dispersing agents containing a sulphonic acid group. Notwithstanding the many material which have been suggested as emulsifying or dispersing agents in the preparation of yarn treating emulsions, there is still a great demand in the textile industry for agents which will give stable aqueous emulsions of the textile lubricants commonly employed to lubricate and otherwise treat yarns composed of or containing organic derivatives of cellulose and similar cellulosic materials.
This invention has as its principal object to provide a new class of self-dispersible compounds which are particularly adapted for use as emulsiflers for textile yarn lubricants, as textile lubricants as such, and as deelectrifying or anti-static agents. A further object is to provide yarn lubrihydroxylated or unblown oils, fats, and waxes, such as castor oil, cod liver oil, rapeseed oil, carnauba wax and Japan wax with a phosphating agent such as phosphoric acid and the various pyro-phosphoric acids, thio-phosphoric acids and the corresponding pyro acids, phosphorus pentoxide, phosphorus pentasulilde, phosphorus pentachloride, phosphorus oxychloride, phosphorus thiochloride and the like, or with a phosphiting agent such as phosphorus acid, phosphorus trichloride, phosphorus oxide, P(OH) 2C1, P(OH) C12, PClz-NH: and the like-self-dispersible compounds which are excellent emulsifiers for textile lubricants and also good lubricants in and of themselves, may be produced. Although all of the above-mentioned phosphating and phosphiting agents are operative to produce such compounds in accordance with our invention, phosphoric acid is probably the least eflicacious. Of the various hydroxylated or unblown oils which we have found satisfactory for the purposes of our invention, the highly hydroxylated oils such as castor oil and cod liver ,oil are outstanding in their ability togive phosphated and .phosphited compounds capable of acting as surface active, de-electrifying, emulsifying, and lubricating agents in accordance with our invention.
It should be noted that all of the oils within the contemplation of our invention are composed of or contain compounds having at least one free hydroxyl group or its equivalent, in its molecule which is subject to phosphation or phosphition.
Of thesevarious oils we have found that those resulting from the phosphation or phosphition of vegetable, animal and marine oils having an iodine value between and 100, and the organic and inorganic base salts of these phosphated and phosphited oils, are of exceptional value as surface-active, deelectrifying, emulsifying, and lubricating agents.
Of the many phosphated oils of our invention those which have proved outstanding in actual practice are phosphated blown neats-foot, phosphated blown olive and phosphated blown castor oil's. Of the phosphated unblown or hydroxylated oils, phosphated castor and cod liver oils are outstanding. v
We have found that these phosphated and phosphited blown and unblown oils and in par ticular the inorganic and organic base salts of phosphated and phosphited blown oils having an iodine number of 50-100, are especially effective in the compounding of compositions adapted for the lubrication and other treatment of yarns composed of or containing organic derivatives of cellulose, such as cellulose acetate, since, not only are they excellent dispersing or emulsifying agents for the textile lubricants commonly employed in such compounds, for example, neat'sroot, olive, and light mineral oils, but also are themselves selt-emulsifiable oils which may be used as the primary lubricant in such compositions. These phosphated and phosphited oils are also excellent de-electriiying or anti-static agents and may also be used as'vehiclesfor fugitive dyes and as dye assistants in the permanent dyeing or various types of textile fabrics includ- Pnosrna'ran COMPOUNDS Example 1 37 gm. of castor oil are added to 6 gm. of PO Cla in pyridine. The reaction is completed by warming. The product is filtered, washed with aqueous bicarbonate, and neutralized. The reaction product is a seli-dispersible, cloudy, brown oil.
Example 2 200 gm. of rapseseed oil are warmed with 25 gm. of
in pyridine. The reaction product is filtered and the pyridine is removed in a vacuum. The solution is neutralized with aqueous ethylarnine to give a pleasant smelling viscous yellow 011.
Example 3 Carnauba wax and crystalline phosphoric acid are heated in a molecular proportion of. 1:1 on the steam bath for 24-60 hr. The product, after neutralization withasuitable base such as diethylcyolohexylamine, triethanolamine, tetra-- ethylammonium hydroxide, ditetrahydroiurfurylamine, etc., is a selt-dispersible, gelatinous dark oil.
Example 4 g A mixture of '75 gm. of castor oil and 25 gm. of carnauba wax is treated with 75 gm. of ethylene glycol and 20 gm. of P205. The reaction product is neutralized with 90% triethanolamine. The heavy brown 011 obtained is self-emulsifiable in water.
Example 5 100 gm. of reduced and partially acetylated castor oil are heated with 60 gm. oi sirupy phosphoric acid and 20 gm. of P205 for hr. at 60. The neutralized product is an oily solid.
Example 6 200 gm. of Japan wax are heated with 250 gm. of PS0]: (NHCnHas) and 50 gm. of Cellulosolve for 10 hr. in 1 liter of C014. The reaction is completed by removing the HCl and 0014 in vacuo. The product is a low melting waxy solid.
Example 7 100 gm. of castor oil are heatedin vacuo at 180 with 100 gm. of anhydrous NazHP04, using glycerine as a solvent. The reaction product is washed with a small quantity of water, leaving a slippery waxy powder.
Example 8 10 lb. of
are ground with 4 lb. oi phosphated castor oil, prepared as described above, and the mixture poured into hot water. 500 lb. of cellulose acetate thread, filaments, fiber or cloth are then dipped and dyed.
Example 9 100 gm. of phosphated carnauba wax are added to 900 gm. of olive oil and 10 kg. of water. This emulsion is then applied to threads of cellulose and its derivatives to assist in processing operations such as weaving, spinning and knitting.
Example 10 1 lb. of the neutralized product of the reaction between castor oil, P205 and ethylene glycol is added to 10 lb. of neats-foot oil and the mixture applied to threads and filaments of cellulose and its organic derivatives such as cellulose acetate, to reduc friction in processing operations.
Example 11 5% of a neutralized phosphated castor oil prepared as described above is added to the common lubricants such as mineral oils, vegetable oils and blown oils to produce stabl emulsions of the latter to facilitate their application to filaments and threads of cellulose and its derivatives, and their removal therefrom.
Example 12 3-10% by weight of the neutral reaction product obtained in Example 6 is applied by means of a wick, roll, or spray to threads or filaments of cellulose and its derivatives, to assist in textile processing operations.
Example 13 10% of the neutral reaction product between castor oil, cetyl alcohol and POCls worked up as previously described is applied to knitting yarn to reduce friction and electrification.
Example 14 Mixtures of any of the phosphated oils prepared above or similar ones are added to oils such as neats-foot and applied to leather and leather substitutes to give softness and line handle.
Example 15 100 gm. of reduced rapeseed oil are treated with 20 gm.of
O N(CsH11): 014
N (CnHzs)2 in a ratio of 1:1 in pyridine and the reaction completed by gentle-warming. The solution is filtered and washed. The resultant waxy solid is insoluble in water.
7 Example 16 I 50 gm. of reduced'castor oil are treated with in benzene and the HCl formed and benzene removed in vacuo. The reaction product is a lowmelting waxy solid.
Example 17 100 gms. of unblown castor oil are heated with 40 grains of euro-r m):
at 40-50 C. for hours and then on a water bath for five hours. The product is cooled and poured into iced water containing sodium carbonate. It is found to be a water-soluble oil which has valuable properties as a wetting out agent, de-electrifier, and a lubricant in the treatment of yarns composed of or containing organic derivatives of cellulose.
, Example 18 100 gm. of oxidized neats-foot oil are heated with '70 gm. of 75% phosphoric acid at 60 for 8 hr. and the product washed with water several times and dried. The orange, viscous oil produced is soluble in water when neutralized with a base.
Example 20 50 gm. of oxidized olive oil are treated in the cold with 10 gm. of phosphorus pentoxide and 2 cc. of water. The reaction product is well washed with water and dried. The clear thick oil obtained is soluble in a :basic solution.
Example 21 35 gm. of blown sperm oil are heated at 95 for 4 hr. with 10 gm. of sirupy phosphoric acid and 0.1 gm. of concentrated sulfuric acid. The heavy oily product is washed with water, dried under reduced pressure, and neutralized.
Example 22 500 gm. of blown rapeseed oil are treated with one equivalent of in benzene and then warmed. The hydrochloric acid and benzene are removed under reduced pressure. The reaction product is hydrolyzed with dilute sodium bicarbonate. The acid phosphate may be neutralized with a base such as ditetrahydrofurfurylamine or diethylcylohexylamine to give a water-soluble compound.
Example 23 200 gm. of blown Japan wax are warmed with 50 gm. of C11H35OPOC12 in chloroform. The chloroform and hydrochloric acid are distilled of! under reduced pressure. The product is hydrolyzed and then neutralized with triethanolmine. It is a thick, yellow-brown, self-dispersible oil.
Example 24 A mixture of 33 gm. of blown teaseed oil, 88 gm. blown rapeseed oil, and 33 gm. blown peanut oil is treated with 140 gm. of PSClflNH-Cufia) in carbon tetrachloride and the reaction product worked up as previously described. The oil obtained is seli-emulsiflable, stable to heat, and very viscous.
Example 25 A mixture of gm. of blown neats-foot oil-and 25 gm. of blowncarnauba wax is treated with 75 gm. of ethylene glycol and 20 gm. of phosphorus pentoxide. The reaction product is washed. dried, and neutralized. The semi-solid waxy material is fairly soluble in water.
Example 26 100 gm. of oxidized olive oil with a high acetyl value are treated with 10 gm. phosphorus pen-toxide and 50 gm. methyl Cellosolve. The reaction product is neutralized with ditetrahydrofurfurylamine. The product is a resinous brown oil, fairly soluble in water.
Emmple 27 100 rm. of neats-foot oil are blown in the presence of 20 gm. of sirupy phosphoric acid at 100 for 10 hr. The resulting product is water-soluble and resembles that obtained in Example 19.
Example 28 A mixture consisting of 50 ounces castor oil and 50 ounces .blown kapok seed oil is heated with 20 ounces of phosphoric acid and 6.7 ounces of phosphoric anhydride for 4 hr. The product is washed, dried and neutralized. It is a gelatinous, water-soluble oil.
Example 29 100 gm. of castor oil are heated with 60 gm. crystalline phosphoric acid until a jell is formed. The product is melted, washed with hot water and neutralized with an organic or inorganic base.
- Example 30 100 gm. of blown and reduced neat's-foot oil are heated 10 hr. with 100 gm. of 75% mmphosphoric acid. The product is washed and neutralized.
Example 31 To -5 lb. of an anthraquinone dye are added 2 lb. of phosphated blown castor which has been previously almost completely neutralized, and the mixture is poured into water heated to 200 lb. of textile material in the form of thread or cloth are then dipped and dyed.
Example 32 1 lb. of a phosphated oxidized neats-foot oil prepared as described above is added to 10 lb. of olive oil and 80 lb. of water. The emulsion is then applied to threads of cellulose and its derivatives to assist in processing operations such as weaving, spinning, etc.
Example 33 1 lb. of the neutralized product of the reaction between blown castor oil, phosphoric anhydride, and ethylene glycol is added to 10 lb. of neats-foot oil and the mixture applied to threads of cellulose and its derivatives, especially cellulose acetate, to reduce friction in processln'g operations.
- Example 34 by weight of a. neutralized phosphated castor oil-blown rapeseed oil mixture is added to the common lubricants such as mineral oil, vegetable oils, and blown oils to produce stable emulsions of the latter and facilitate their application to filaments and threads of cellulose and its derivatives, as well as to facilitate the removal of these oils therefrom.
Example 35 1-5% of the neutral reaction product of blown olive oil, phosphorus oxychloride and Cellosolve is applied in the usual way to threads or filaments of cellulose and its derivatives to aid in textile processing operations.
Example 36 85% of the neutral reaction product between castor oil, blown rapeseed 'oil and blown sesame oil is mixed with of a softener such as glyce'ryl acetals, Cellosolve formal, glycols and polyglycols and ethers thereof. The mixture is applied to threads of cellulose and its derivatives to facilitate knitting operations.
Example 37 Mixtures of any of the phosphates prepared above with oils such neats-foot oil are: applied to leather to give softness and a fine handle.
Example 38 10% of the neutral product of the reaction between blown carnauba wax, POC12(OC17H35), and cetyl alcohol isdissolved together with cellulose acetate stearate and of a common plasticizer such as butyl or any phthalate, triphenyl phosphate, Cellosolve phthalate, etc. in a suitable solvent to produce a plastic of good strength, elasticity and appearance.
Example 39 1% of a slightly acid phosphated oxidized castor oil is added to soap which is to be used in hardwater.
Example 40 A fugitive tint solution is prepared for ap plication to textile threads, particularly of cellulose acetate, having the following composition:
Grams Phosphated blown olive oil sodium salt 0.2 Blown olive oil 2.0 Chicago blue dye 0.02 'Water 100 The emulsion is applied to the yarn by any suitable means such as a spray, wick, or roller and may be dried if desired.
Example 41 Grams Phosphated blown castor oil triethanol- Pnosrm'rsn COMPOUNDS Example 43 37 g. of castor oil are added to 6 g. phosphorus trichloride in pyridine. The reaction is completed by warming. The product is filtered, treated with aqueous sodium carbonate. The reaction product is self dispersible in water.
Example 44 200 g. of rapeseed oil are warmed with g.
' Pol,
Hi l-C1211 and the reaction is completed by warming. The solution is filtered and the pyridine is removed under reduced pressure. The product is treated with water and then with ethylamine to give a viscous yellow oil.
Example 45 Carnauba wax and phosphorus trioxide are heated in a molecular proportion of 1:1 on the steam bath for 24-60 hours. The product after neutralization with a suitable base such as diethylcyclohexylamine, ditetrahydrofurfurylamine,
. ethanolamine, etc., is self-dispersible in water.
Example 46 A mixture of 75 g. castor oil and 25 g. carnauba wax is treated with g. phosphorus trioxide. The reaction product is neutralized with triethanolamine. The heavy brown oil forms an aqueous dispersion.
Example 47 a 100 g. of reduced partly acetylated castor oil are treated at till-100 for 10 hours with 60 g. phosphorus acid and 30 g. phosphorus trisulfide. The product is neutralized with tetramethylammonium hydroxide. The product forms an aqueous suspension.
Example 48 200 g. Japan wax are treated with 200 g.
PCI:
NH-CH and worked up as above. The sodium salt is prepared.
Example 49 100 g. blown castor oil are heated with 25 g. phosphorus acid at 110-115 for 5 hours with stirring. The product is then neutralized with triethanolamine and is soluble in warm water. In place of blown castor oil, we may use blown neats-foot, sperm, olive, teaseed, soya bean, rape-- seed, com, menhaden, carnauba, Japan wax, etc.
} Example 50 100 g. blown neats-foot oil are heated with 50 g. phosphorus acid as in Example 49 and the product is then' treated in pyridine with 20 g. phosphorus trichloride. The reaction product is poured into dilute sodium hydroxide.
Example 51 g. blown castor oil are reacted with 75 g. phosphorus acid as in Example 49 and then in pyridine with 20 g. phosphorus oxychloride. The
diethylcyclohexylamine salt is made in the usual manner. The product is water soluble.
Example 52v 100 g. blown sperm oil are heated with a mixture of 40 g. phosphorus acid and 30 g. phosphoric acid at 96-120 for 4 hours. The trimethylbenzyl ammonium hydroxide salt is water soluble.
- Example 53 100 g. blown camauba wax are reacted with 60 g. phosphorus acid as above.
Example 54 A mixture 01' 50 g. blown soya bean oil and 50 g. blown teaseed oil is reacted with 70 g. phosphorus acid as above and neutralized with a mixture oi potassium hydroxide and dibutylamine.
Example 55 5 pounds -1,4-dimethylamino anthraquinone are finely ground with 2 pounds 01' the sodium salt of phosphited blown olive oil and poured into water heated to 85. 200 pounds of cellulose acetate knit fabric are entered and dyed blue.
Example 56 1 pound of a phosphited oxidized neats-foot oil is added to pounds olive oil and 80 pounds water. The emulsion is then appliedto threads of cellulose or its derivatives to assist in weaving, knitting, etc.
Example 57 fats, or waxes of our invention may be employed with a high degree of effectiveness as emulsifying, wetting out and deelectrifying agents in the compounding of yarn treating compositions. Various ingredients such as other lubricating agents, solvents, non-solvents, blending agents and the like may be employed in connection with these compounds within the scope of our invention. Likewise, various dyes or other coloring matter may be employed in case it is desired to permanently or fugitively tint or dye the mate-' rial undergoing treatment.
Although we have found it convenient to illustrate our invention by reference to compositions containing specific percentages of the various ingredients, these percentages may vary widely depending upon the particular purpose for which the composition is intended.
While we have described our invention with reference to the preparation of emulsions particularly adapted for the treatment of yarns composed of organic derivatives of cellulose such as cellulose acetate, the broad scope of our invention includes the preparation of emulsions adapted for the treatment of many other types of cellulose derivative yarns such as those composed of or containing cellulose propionate, cellulose butyrate, cellulose acetate propionate, cellulose acetate butyrate, ethyl cellulose, methyl cellulose, benzyl cellulose and others, as well as to the conditioning of silk, wool, cotton, viscose and other natural or artificial materials.
The term yarn as used herein and in the claims is to be understood as including a single filament, a plurality of filaments associated into the form of a thread, either of high or low twist, single or'multiple threads associated or twisted together, composite threads composed of a mix ture of natural and artificial filaments or a composite thread formed by twisting together indivldual strands of natural or artificial materials, as well as cut staple fibers produced from natural and/or artificial filaments or threads and spun yarn produced from such staple fibers.
What we claim is:
1. The process of simultaneously lubricating and eliminating the tendency of yarns, filaments or fibers composed of or containing organic de- 'rivatives of cellulose to accumulate charges of static electricity, which comprises applying thereto a composition containing a its essential lubricating and anti-static component an oil which is the product of reaction obtained by first blowing an oil containing compounds having a certain degree of unsaturation to produce compounds having at least one free hydroxyl group or its equivalent in its molecule which is subject to phosphation or phosphition, and then reacting the blown oil with an agent selected from the group consisting of phosphating and phosphiting agents.
2. The process of simultaneously lubricating and eliminating the tendency of yarns, filaments or fibers composed of or containing organic derivatives of cellulose to accumulate charges of static electricity, which comprises applying thereto a composition containing as its essential lubricating and anti-static component a phosphated oil which is the product of reaction obtained by first blowing an oil containing compounds having a certain degree of unsaturation to produce compounds having at least one free hydroxyl group or its equivalent in its molecule which is subject to phosphation, and then reacting the blown oil with a phosphating agent.
3. The process of simultaneously lubricating and eliminating the tendency of yarns, filaments or fibers composed of or containing cellulose acetate to accumulate charges of static electricity, which comprises applying thereto a composition containing as its essential lubricating and anti-static component a phosphated oil which is the product of reaction obtained by first blowing an oil containing compounds having a certain degree of unsaturation to produce compounds having at least one free hydroxyl group' cating and anti-static component a phosphited oil which is the product of reaction obtained by first blowing an oil containing compounds having a certain degree of unsaturation to produce compounds having at least one free hydroxyl group or its equivalent in its molecule which is subject to phosphition and then reacting the blown oil with a phosphiting agent.
5. The process of claim 2 in which the phos-- phated oil is phosphated blown neats-foot oil. 6. The process of claim 2 in which the phoshated oil is phosphated blown olive oil.
7. The process of claim 2 in which the phosphated oil is phosphated blown sperm oil.
JOSEPH B. DICKEY. JAMES G. McNALLY.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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US285208A US2345734A (en) | 1939-07-18 | 1939-07-18 | Self-emulsifying phosphated and phosphited oils as antistatic lubricants |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US285208A US2345734A (en) | 1939-07-18 | 1939-07-18 | Self-emulsifying phosphated and phosphited oils as antistatic lubricants |
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US2345734A true US2345734A (en) | 1944-04-04 |
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ID=23093236
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US285208A Expired - Lifetime US2345734A (en) | 1939-07-18 | 1939-07-18 | Self-emulsifying phosphated and phosphited oils as antistatic lubricants |
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Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2466393A (en) * | 1945-06-29 | 1949-04-05 | Eastman Kodak Co | Preparation of esters of acids of phosphorus |
US2466394A (en) * | 1945-06-29 | 1949-04-05 | Eastman Kodak Co | Preparation of esters of acids of phosphorus |
US2478377A (en) * | 1945-06-29 | 1949-08-09 | Eastman Kodak Co | Preparation of esters of acids of phosphorus |
US2490748A (en) * | 1945-06-29 | 1949-12-06 | Eastman Kodak Co | Preparation of esters of acids of phosphorus |
US2498408A (en) * | 1945-12-06 | 1950-02-21 | Gen Aniline & Film Corp | Antistatic textile materials |
US2529304A (en) * | 1948-02-19 | 1950-11-07 | Standard Oil Dev Co | Extreme pressure lubricants |
US2600058A (en) * | 1949-03-09 | 1952-06-10 | Texas Co | Lubricant containing soap of phosphated hydroxy fatty acid or glyceride |
US2895973A (en) * | 1955-02-09 | 1959-07-21 | Exxon Research Engineering Co | Metal salts of dithiophosphoric acids |
US2965657A (en) * | 1956-06-04 | 1960-12-20 | Swift & Co | Phosphorated oils |
US3676468A (en) * | 1966-03-26 | 1972-07-11 | Henkel & Cie Gmbh | Preparation of factice-like products |
US4160089A (en) * | 1973-10-18 | 1979-07-03 | Aquila S.P.A. | Utilization of orthophosphoric esters for the production of aqueous fluids for working metals |
US4173679A (en) * | 1976-12-24 | 1979-11-06 | Hoechst Aktiengesellschaft | Liquid thermostable phosphoric acid esters for the fiber conditioning |
JPS62286041A (en) * | 1986-06-04 | 1987-12-11 | Konica Corp | Photographic film magazine |
US5972497A (en) * | 1996-10-09 | 1999-10-26 | Fiberco, Inc. | Ester lubricants as hydrophobic fiber finishes |
-
1939
- 1939-07-18 US US285208A patent/US2345734A/en not_active Expired - Lifetime
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2466393A (en) * | 1945-06-29 | 1949-04-05 | Eastman Kodak Co | Preparation of esters of acids of phosphorus |
US2466394A (en) * | 1945-06-29 | 1949-04-05 | Eastman Kodak Co | Preparation of esters of acids of phosphorus |
US2478377A (en) * | 1945-06-29 | 1949-08-09 | Eastman Kodak Co | Preparation of esters of acids of phosphorus |
US2490748A (en) * | 1945-06-29 | 1949-12-06 | Eastman Kodak Co | Preparation of esters of acids of phosphorus |
US2498408A (en) * | 1945-12-06 | 1950-02-21 | Gen Aniline & Film Corp | Antistatic textile materials |
US2529304A (en) * | 1948-02-19 | 1950-11-07 | Standard Oil Dev Co | Extreme pressure lubricants |
US2600058A (en) * | 1949-03-09 | 1952-06-10 | Texas Co | Lubricant containing soap of phosphated hydroxy fatty acid or glyceride |
US2895973A (en) * | 1955-02-09 | 1959-07-21 | Exxon Research Engineering Co | Metal salts of dithiophosphoric acids |
US2965657A (en) * | 1956-06-04 | 1960-12-20 | Swift & Co | Phosphorated oils |
US3676468A (en) * | 1966-03-26 | 1972-07-11 | Henkel & Cie Gmbh | Preparation of factice-like products |
US4160089A (en) * | 1973-10-18 | 1979-07-03 | Aquila S.P.A. | Utilization of orthophosphoric esters for the production of aqueous fluids for working metals |
US4173679A (en) * | 1976-12-24 | 1979-11-06 | Hoechst Aktiengesellschaft | Liquid thermostable phosphoric acid esters for the fiber conditioning |
JPS62286041A (en) * | 1986-06-04 | 1987-12-11 | Konica Corp | Photographic film magazine |
US5972497A (en) * | 1996-10-09 | 1999-10-26 | Fiberco, Inc. | Ester lubricants as hydrophobic fiber finishes |
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