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Treated cellulose organic acid ester fibers

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US2743193A
US2743193A US37345553A US2743193A US 2743193 A US2743193 A US 2743193A US 37345553 A US37345553 A US 37345553A US 2743193 A US2743193 A US 2743193A
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Prior art keywords
cellulose
acid
alcohol
ester
partial
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Raymond E Donaldson
White Charles Clayton
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Eastman Kodak Co
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Eastman Kodak Co
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS, OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M7/00Treating 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
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS, OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/40Reduced friction resistance, lubricant properties; Sizing compositions
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/29Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913Rod, strand, filament or fiber
    • Y10T428/2933Coated or with bond, impregnation or core
    • Y10T428/2964Artificial fiber or filament
    • Y10T428/2965Cellulosic

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.
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Cited By (4)

* Cited by examiner, † Cited by third party
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

Citations (10)

* Cited by examiner, † Cited by third party
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

Patent Citations (10)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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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