CA1219252A - Fatty acid esters of phenol derivative alkoxylates and their use as fiber finish components - Google Patents
Fatty acid esters of phenol derivative alkoxylates and their use as fiber finish componentsInfo
- Publication number
- CA1219252A CA1219252A CA000424456A CA424456A CA1219252A CA 1219252 A CA1219252 A CA 1219252A CA 000424456 A CA000424456 A CA 000424456A CA 424456 A CA424456 A CA 424456A CA 1219252 A CA1219252 A CA 1219252A
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- Canada
- Prior art keywords
- carbon atoms
- fiber
- compound
- lubricant formulation
- weight
- 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.)
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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
- 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
- D06M13/10—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 oxygen
- D06M13/165—Ethers
-
- 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
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
FATTY ACID ESTERS OF PHENOL DERIVATIVE
ALKOXYLATES AND THEIR USE AS FIBER FINISH COMPONENTS
Abstract of the Disclosure A fatty acid ester of alkoxylated phenol deriva-tives provides an effective fiber lubricant when applied pure or in a water emulsion.
ALKOXYLATES AND THEIR USE AS FIBER FINISH COMPONENTS
Abstract of the Disclosure A fatty acid ester of alkoxylated phenol deriva-tives provides an effective fiber lubricant when applied pure or in a water emulsion.
Description
2~;~
FATTY ACI~ ESTERS OF PHENOL DERIVATIVE
ALKOXYLATES AND THEIR USE AS FIBER FINISH COMPONENTS
. ~
Back~round of the Invention 1. Field of the Invention 7 ~ :. __ _ __ The invention relates to a fiber lubricant, a fatty acid ester of an alkoxylated phenol derivative, which has effective thermal and oxidative stability, non-volatility, product stability and, in a preferred embodi-ment, emulsification properties and which when applied to a fiber, as a fiber lubricant formulation, exhibits effective viscosity and lubricity.
2. Description of the Prior Art . _ . . .
Traditionally, a fiber lubricant formulation consists of a base material, or lubricant, such as mineral oil, alkyl esters of fatty acids or vegetable oils; emulsi-fiers that allow the lubricant to be applied from a water solution; antistatic agents; antioxidants; bacteriocides;
friction modifiers; and buffering agents.
A fiber lubricant is critical to the conversion of nylon or polyester fiber into useful yarn for textile manufacturing. The fiber lubrlcant has several functions.
One function is to control friction. The fiber lubricant may protect the newly spun fiber from fusion or breakage by controlling the yarn-to-metal friction at frictional contact points between the yarn and machine guides, rollers, draw ~19'~S~
plates, heater plate and texturing false twist spindles or friction discs. The lubricant also functions to provide yarn cohesion giving strength to the yarn by holding the yarn bundled together and by allowing the yarn to build up an acceptable package at the end of processing. Static electricity that is formed as the yarn rapidly moves through the processing equipment would also be controlled. The lubricant must also protect machine surfaces from wear.
U.S~ ~,165,405 discloses fiber lubricants based upon fatty esters of heteric polyoxyalkylated alcohols wherein mononuclear, monofunctional initiators are alkoxy-lated and then esterified. U.S ~,127,490 relates to lubricating fibers with a major amount of lubricant and a minor amount of a stabilizer, said stabilizer being the reaction product of one mole of dicyclopentadiene and at least one mole of p-cresol, further reacted with at least one-half mole of isobutylene. U.S. 4,134,841 relates to a fiber lubricant which is a composition comprising a non-hindered polyphenyl stabilizer and a polyether lubricant.
U.S. 4,252,528 relates to a spin finish for synthetic fibers of a thermally stable lubricant and a surfactant deri~ed from an ethylene oxide-propylene oxide block copolymer adduct of an alkylated phenol. U.S. 3,578,594 relates to a fiber treating composition consisting essentially of about 90 percent to about 25 percent by weight of at least one .
~2~25~
ester of an ethoxylated aliphatic alcohol and about 10 percent to about 75 percent by weight of at least one ester of an ethoxylated arylphenol. The examples relate to ~-methyl benzyl phenol or bis ~-methyl benzyl phenol as the aryl phenol. A problem of the prior art fiber lubricants mentioned above is that they are not disclosed as being capable of being used alone or in a water emulsion as a fiber lubricant formulation. None of the above references discloses the use as a fiber lubricant of the products of applicants' invention, nor do they suggest the use of applicants' product alone or as a water emulsion.
A purpose of the invention was to provide a fiber lubricant which may be used by itself in pure form as a fiber lubricant formulation. Another purpose of the invention was to provide a self-emulsifiable fiber lubricant for use as a fiber lubricant formulation.
Summar~ of the Invention . _ A fiber lubricant has been discovered having effective thermal and oxidative stability, non-volatility, product stability, and, in a preferred embodiment, emulsifi-cation properties, and which when applied to a fiber, as a fiber lubricant formulation, exhibits effective viscosity and lubricity. The fiber lubricant is useful as a fiber lubricant formulation in pure application to polyester or nylon fiber during a drawing and texturing operation. The ~2~9;~
fiber lubricant formulation is used in a process of lubri- -cating synthetic fibers which comprises applying the fiber lubricant to the fiber in an amount between 0.05 percent by weight and 5 percent by weight, based on the weight of the lubricated fiber~ The fiber lubricant comprises a compound selected from the group consisting of O(A)nR
I
X ~ X ~ (I) O(A)nR
R"~X~
( I I ) f (A,nR
~ R~ ~ "' (III) : R""
and : -4-32~
(A)nR
X ~ R~ (IV) R'' wherein A is an oxyalkylene radical having 2 carbon atoms to 4 carbon atoms or mixtures thereof, R is hydrogen or acyl containing from 8 carbon atoms to 22 carbon atoms, R' is alkyl containing from 1 carbon atom to 10 carbon atoms, R'' is alkyl containing from l carbon atom to 22 carbon atomst R''' is alkyl containing from 4 carbon atoms to 8 carbon atoms and R'"' is R'' or R''', X is an alkylidene radical containing from 1 carbon atom to 3 carbon atoms and n is an integer such that the molecular weight of the compound is between 500 and 2500 and with the proviso that either R'7 or R''' is ortho to the oxygen in Eormula III. In preferred embodiments the oxyalkylene radical is oxyethylene or a mixture of oxyethylene and up to 50 percent by weight of an oxyalkylene radical having 3 carbon atoms to 4 carbon atoms and provides effective hydrophilicity to the compound to enable it to self emulsify in waterO
Description of the Preferred Embodiments The lubricants of the present invention are prepared from three essential ingredients, i.e., certaln phenol derivatives, alkylene oxides and fatty acids.
. .
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Useful as the phenol derivatives are compounds selected from the group consisting.of the following form-ulas:
<~X~X-<~, tV) R'' ~ X ~
r tVI) ~R t V I I ) ~ R'''' ~X ~) ( VI I I ) R~ R' wherein X~ R', R'', R''' and R'''' are as described above.
Examples o X are alkylidene radicals such as methylene, ethylene and propylidene. Examples of R' and R'' are methyl lZ~9'~5~
and isobutyl. Examples of R''' and R'''' are butyl and octyl. Preferably used as the phenol derivative of formula V is a compound wherein X is fH3 --c--H
as the phenol derivative of formula VI is a compound wherein x is c~3 as the phenol derivative of formula VII is a compound wherein R'' is C4Hg , R''' is C8H17- and R
is C8H17 - or C4Hg- or a compound wherein R'' is C4Hg-, R''' is C4Hg- and R'''' is CH3- and as the phenol derivative of formula VIII is a compound wherein X is ~C-R' is CH3- and R'' is C4H9-.
Useful as alkylene oxides, from which the oxy-alkylene radisal derives, are al~ylene oxides containing 2 carbon atoms to 4 carbon atoms such as ethylene oxide, ~Z~Z5~
propylene oxide and butylene oxide. Useful in a preferred embodiment i9 ethylene oxide or a mixture of ethylene oxide and other alkylene oxides which when used in a mixture with ethylene oxide impart a hydrophilicity effective to self emulsify the compound. In lieu of the other alkylene oxides, other 3 or 4-carbon cyclic ethers such as tetrahydrofuran, oxetane, and methyl oxetane may be used.
Preferaby used are mixtures of ethylene oxide and propylene oxide.
The oxyalkylene is present in the fiber lubricant in an amount, as represented by n, such that the molecular weight of the compound is between 500 and 2500. Preferably used is a block of between 5 and 20 moles, such as 5, 10 or 15 moles of ethylene oxide per mole of phenol derivative.
Also preferably used is a heteric mixture of about 70 percent by weight oxyethylene and about 30 percent by weight oxypropylene.
Useful as fatty acids are those containing between 8 carbon atoms and 22 carbon atoms, preferably between 16 and 20 carbon atoms and more preferably 18 carbon atoms, such as isostearic acid.
The phenol derivative is ethoxylated by adding the phenol derivative and a basic catalyst to an autoclave evacuated to a vacuum and pressurized with nitrogen and equipped -~ith temperature, pressure and vacuum controls, and thereafter heated. The alkylene oxide is added at a ;~ constant rate until all the oxide is added. The reaction then proceeds at a temperature between 90C and 130C until a constant pressure is observed. Esterification is then ~23~9J~S'~
accomplished by adding approximately equal molar amounts of fatty acid and alkoxylated phenol derivative. Acid cata-lysts, such as methane sulfonic acid and hypophosphorus acid are added and the esterification reaction is allowed to proceed at a constant temperature, such as 165C under a nitrogen blanket.
The lubricants of this invention are applied to the fiber in an amount between 0.05 percent by weight and 5 percent by weight~ based on the weight of the lubricated fiber.
The lubricity of the products of this invention on synthetic yarns may be determined using any reasonable method One useful test method measures the lubricity, in units of the coefficient of friction, of nylon filaments having fiber lubricants applied to them at a concentration of about 1 percent lubricant by weight of filament by the procedure of the following two paragraphs.
A stable aqueous emulsion of the lubricant is prepared. This emulsion is applied to the yarn, such as nylon or polyester, using an apparatus in which the yarn is passed at a controlled speed through a continually replen-ished drop of finished solution or dispersion of specified concentration. A suitable apparatus is the ATLAS*yarn finish applicator sold by the Precision Machine and Develop-ment Company of Wilmington, Delaware. The lubricant * trademark _g_ dispersion is metered to the continually replenished drop of solution using a syringe pump. The yarn is fed over an adjustable canter roller which functions to space the yarn over a drying drum used to remove water. The yarn is finally passed over a winding tube and subsequently con-ditioned for 16 to 24 hours at 65 percent relative humidity and 70F before being tested.
The coefficient of friction (f~ may be determined on any suitable machine, such as a Rothschild F Meter utilizing 0.313 inch diameter ceramic (Al Si Mg) and satin chrome fric~on pins that has friction surface at a yarn contact angle of 180. The yarn speed is varied, such as at 50, 100, 150, 200, and 250 meters per minute. The yarn tension may be varied such as at 4 or 6 grams on the input side as determined by tensiometers by the Rothschild*F
meter. The (f) values are determined directly by reading the chart produced by the Rothschild*~ meter.
Viscosity may be determined by any standard procedure, such as using a~Brookfield*viscometer or Ubelohde*
tube Eollowing ASTM D444 71/79 or D2161-79. The viscosity of the fiber lubricants of this invention have a controlled viscosity range, from 500 to 1500 Saybolt universal sec-onds. A viscosity below this range i5 detrimental to processing the fibers and a viscosity above this range causes excessive add on to the fibers.
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Thermal and oxidative stability as well as non-volatility of the fiber lubricant may be tested by a number of suitable procedures such as the hot plate test, the circulating air oven test, dynamic thermogravimetric analysis and isothermal thermogravimetric analysis. The hot plate test proceeds by placing metal cups, 3 for each example, on a heater and maintaining the temperature at 240C for 24 hours. At intervals of time, the weight loss for each of the 3 samples is determined and averaged and the quality of residue determined. The hot plate test is representative of thermal stability as measured by the results at 240C for 24 hours and of oxidative stability by the quality of the residue. The circulating air oYen test proceeds as in the hot plate test except the hot plate and samples are placed in a circulating air oven. The thermo-gravimetric analyses proceed as follows: the dynamic thermogravimetric analysis measures the temperature in degrees centi~rade at which a specific percentage by weight, such as 1 percent by weight and 10 percent by weight, of the sample is lost in a test atmosphere, such as air or nitrogen, while heating the sample at a constant heating rate, such as 20 degrees per minute; and the isothermal thermogravimetric analysis measures the percent by weight loss of the sample at a constant temperature) such as 210C, for a specific time interval, such as 40 minutes, while the 5~
sample is continuously weighed.
The product stability of the fiber lubricant may be tested by any suitable method. The ability of the product of the invention to be storage stable is excellent.
The emulsification properties of the fiber lubricant may be tested by preparing a mixture containing 10 parts of fiber lubricant, 20 parts of mineral oil and 70 parts of water. The mixture is shaken vigorously and allowed to stand for 24 hours. If separation of the emulsion does not occur, the emulsion is considered stable.
The products of a preferred embodiment of the invention are self emulsifiable with water and do not require additives to make an emulsion.
Additional additives may, however, be added to the fiber lubricants in preparing fiber lubricant formula-tions. These additives are described in U.S. 4,134,8417 ~2~9~S~
The followin~ examples will further illustrate the various aspects of the invention. Where not otherwise specified throughout the specification and claims, temper-atures are in degrees Centigrade, and parts, percentages and proportions are by weight.
Example 1 To an autoclave e~uipped with temperature, pressure, and vacuum controls was added 780 parts of butylated, styrenated cresol (WINGSTAY~ V - Goodyear Company) and 8 parts of 45 percent potassium hydroxide solution. The autoclave was heated to 125C after evacu-ating to a vacuum of less than 10 millimeters mercury and then pressurizing to 34 lbs./square inch with nitrogen.
Ethylene oxide was added at a rate of 250 parts/hour until 1921 parts were added. When constant pressure was observed, the catalyst was removed by deionization and the mixture was further stripped to remove volatiles. This ethoxylate, Example lA, had a hydroxyl number of 66.2 and a viscosity of 883 Saybolt universal seconds at 100F.
To a 2 liter flask having temperature control, stirrer and distillation apparatus were added 891 parts of the above ethoxylate. Next, 279.1 parts of isostearic acid, 4.12 parts of methanesulfonic acid, (70 percent), and 4.0 parts of hypophosphorous acid were added. The temperature was held at a constant 165C in a nitrogen atmosphere until s~
the esterification reaction was complete. After catalyst removal, the product of Example 1 of this invention, the isostearate ester of ethoxylated butylated styrenated cresol, a specific product containing compounds of formula IV above, was obtained having a hydroxyl number of 4.4, an acid number of 1.56 and a viscosity of 781 Saybolt universal seconds at 100F.
Comparison Examples A, B, C and D
A is a polyoxypropylene block adduct of a polyoxy-ethylene adduct of ethylene glycol of approximate average molecular weight of the hydrophobe of 1000 and an oxy-ethylene content of about 50 percent by weight.
B is a polyoxyethylene block adduct of a polyoxy-propylene adduct of propylene glycol of approximate average molecular weight of the hydrophobe of 950 and an oxyethylene content of about 50 percent by weight.
C is a heteric ethylene oxide propylene oxide adduct of a C12-C15 fatty alcohol, having an overall approximate average molecular weight of 1280 and containing about 50 percent ethylene oxide.
D is a polyoxyethylene block adduct of a polyoxy-propylene adduct of bisphenol A of approximate average overall molecular weight of 8350 and an oxyethylene content of about 80 percent by weight.
~z~s~æs~
Lubricity, heat stability and emulsion properties were obtained as follows: An aqueous emulsion of the lubricant of Example 1 was prepared. This emulsion was applied to yarn using an Atlas yarn finish applicator. The coefficient of friction (f) was determined on a Rothschild F
meter utili~ing 0.313 inch diameter ceramic (Al Si Mag) and satin chrome friction pins as the friction surface at a yarn contact angle of 180. The ASTM procedure Standard Test Method for Coefficient Friction, Yarn to Metal Designation 03108-76 was generally followed. The lubricity results, using 40/12 denier nylon 6 yarn, are shown in Table I for ; the products of Example 1 and comparison Example A.
TABLE I
Input Speed Coefficient of Friction Tension Meters/ Example 1Comparison Example A
(Grams)Minute f f 4 50 .70 .73 4 100 .71 .76 4 150 .71 .77 4 200 .71 .77 6 50 .64 .67 6 100 .66 .69 6 150 .67 .70 6 200 .67 .71 Thermal and oxidative stability of the products of Example 1 and comparisons B and C, using a hot plate set at 240C and 3 gram samples, are shown in Table II.
-lS-9~5~
TABLE II
Heat Stability Hot Plate Test Percent Residue ExampleAfter 24 Hours Nature of Residue 1 76.7 Light brown liquid B 2.9 Varnish C 38.8 Dark Brown Liquid Heat stability results for the products of Example 1 and Comparison Example C, using a circulating air oven set at 210C and 3 gram samples, are shown in Table ; IIIo TABLE III
Heat Stability Circulating Air Oven Test Percent Residue ExampleAfter 24 Hours Nature of Residue 187.6 Light Brown Liquid C22.9 Dark Brown Liquid Heat stability results for the product of Example 1 of the invention using thermogravimetric analysis and isothermal percent weight loss are shown in Table IV.
!L9'2~
TABLE IV
Thermogravimetric Analysis Dynamic C Weight Loss of 1% 10% 50%
Example Air/ N2 Air/ N2 Air/N2 Isothermal ~ Weight Loss Smoke Point at 210C -40 Minutes C
1 18.0/4~0 187 Stable emulsions, made with the product of Example 1, and water and with the product of Example 1, water and other materials are shown in Table V.
~'~19%S'~
TABLE V
Emulsions Stable Emulsion Component parts parts parts parts Product of Example 1 12 5 2 20 Tridecyl Stearate36 - - -Butyl Stearate - 15.0 Mineral Oil - - 8 (Crystosol TW) KLEARFAC~ A270 - 3 ~neutralized) Water 52 77 90 80 , ~2~ 5~
Examples 2-20 Examples 3-10 and 14-19 were prepared using the procedure to prepare Example lA. Examples 2, 11-13 and 20 were prepared using the procedure for preparing the product of Example 1. EO is ethylene oxide, PO i5 propylene oxide, product Yl is a commercial product of formula V wherein X is -- C -- , H
(WINGSTAY~ S - Goodyear Company), product Y2 is a commer-cial product of formula VII wherein R" is C4Hg-, ~"' is C8H17- and R"" is either C4Hg- or C8H17-(WINGSTAY~ T - Goodyear Company) and product Y3 is a commercial product of Eormula VI wherein X is -- C --and R" is C~Hg- (WINGSTAY~ C - Goodyear Company).
9~5~
The products are as follows:
Example Composition 2 Laurate ester of Example LA
FATTY ACI~ ESTERS OF PHENOL DERIVATIVE
ALKOXYLATES AND THEIR USE AS FIBER FINISH COMPONENTS
. ~
Back~round of the Invention 1. Field of the Invention 7 ~ :. __ _ __ The invention relates to a fiber lubricant, a fatty acid ester of an alkoxylated phenol derivative, which has effective thermal and oxidative stability, non-volatility, product stability and, in a preferred embodi-ment, emulsification properties and which when applied to a fiber, as a fiber lubricant formulation, exhibits effective viscosity and lubricity.
2. Description of the Prior Art . _ . . .
Traditionally, a fiber lubricant formulation consists of a base material, or lubricant, such as mineral oil, alkyl esters of fatty acids or vegetable oils; emulsi-fiers that allow the lubricant to be applied from a water solution; antistatic agents; antioxidants; bacteriocides;
friction modifiers; and buffering agents.
A fiber lubricant is critical to the conversion of nylon or polyester fiber into useful yarn for textile manufacturing. The fiber lubrlcant has several functions.
One function is to control friction. The fiber lubricant may protect the newly spun fiber from fusion or breakage by controlling the yarn-to-metal friction at frictional contact points between the yarn and machine guides, rollers, draw ~19'~S~
plates, heater plate and texturing false twist spindles or friction discs. The lubricant also functions to provide yarn cohesion giving strength to the yarn by holding the yarn bundled together and by allowing the yarn to build up an acceptable package at the end of processing. Static electricity that is formed as the yarn rapidly moves through the processing equipment would also be controlled. The lubricant must also protect machine surfaces from wear.
U.S~ ~,165,405 discloses fiber lubricants based upon fatty esters of heteric polyoxyalkylated alcohols wherein mononuclear, monofunctional initiators are alkoxy-lated and then esterified. U.S ~,127,490 relates to lubricating fibers with a major amount of lubricant and a minor amount of a stabilizer, said stabilizer being the reaction product of one mole of dicyclopentadiene and at least one mole of p-cresol, further reacted with at least one-half mole of isobutylene. U.S. 4,134,841 relates to a fiber lubricant which is a composition comprising a non-hindered polyphenyl stabilizer and a polyether lubricant.
U.S. 4,252,528 relates to a spin finish for synthetic fibers of a thermally stable lubricant and a surfactant deri~ed from an ethylene oxide-propylene oxide block copolymer adduct of an alkylated phenol. U.S. 3,578,594 relates to a fiber treating composition consisting essentially of about 90 percent to about 25 percent by weight of at least one .
~2~25~
ester of an ethoxylated aliphatic alcohol and about 10 percent to about 75 percent by weight of at least one ester of an ethoxylated arylphenol. The examples relate to ~-methyl benzyl phenol or bis ~-methyl benzyl phenol as the aryl phenol. A problem of the prior art fiber lubricants mentioned above is that they are not disclosed as being capable of being used alone or in a water emulsion as a fiber lubricant formulation. None of the above references discloses the use as a fiber lubricant of the products of applicants' invention, nor do they suggest the use of applicants' product alone or as a water emulsion.
A purpose of the invention was to provide a fiber lubricant which may be used by itself in pure form as a fiber lubricant formulation. Another purpose of the invention was to provide a self-emulsifiable fiber lubricant for use as a fiber lubricant formulation.
Summar~ of the Invention . _ A fiber lubricant has been discovered having effective thermal and oxidative stability, non-volatility, product stability, and, in a preferred embodiment, emulsifi-cation properties, and which when applied to a fiber, as a fiber lubricant formulation, exhibits effective viscosity and lubricity. The fiber lubricant is useful as a fiber lubricant formulation in pure application to polyester or nylon fiber during a drawing and texturing operation. The ~2~9;~
fiber lubricant formulation is used in a process of lubri- -cating synthetic fibers which comprises applying the fiber lubricant to the fiber in an amount between 0.05 percent by weight and 5 percent by weight, based on the weight of the lubricated fiber~ The fiber lubricant comprises a compound selected from the group consisting of O(A)nR
I
X ~ X ~ (I) O(A)nR
R"~X~
( I I ) f (A,nR
~ R~ ~ "' (III) : R""
and : -4-32~
(A)nR
X ~ R~ (IV) R'' wherein A is an oxyalkylene radical having 2 carbon atoms to 4 carbon atoms or mixtures thereof, R is hydrogen or acyl containing from 8 carbon atoms to 22 carbon atoms, R' is alkyl containing from 1 carbon atom to 10 carbon atoms, R'' is alkyl containing from l carbon atom to 22 carbon atomst R''' is alkyl containing from 4 carbon atoms to 8 carbon atoms and R'"' is R'' or R''', X is an alkylidene radical containing from 1 carbon atom to 3 carbon atoms and n is an integer such that the molecular weight of the compound is between 500 and 2500 and with the proviso that either R'7 or R''' is ortho to the oxygen in Eormula III. In preferred embodiments the oxyalkylene radical is oxyethylene or a mixture of oxyethylene and up to 50 percent by weight of an oxyalkylene radical having 3 carbon atoms to 4 carbon atoms and provides effective hydrophilicity to the compound to enable it to self emulsify in waterO
Description of the Preferred Embodiments The lubricants of the present invention are prepared from three essential ingredients, i.e., certaln phenol derivatives, alkylene oxides and fatty acids.
. .
~2~925'~
Useful as the phenol derivatives are compounds selected from the group consisting.of the following form-ulas:
<~X~X-<~, tV) R'' ~ X ~
r tVI) ~R t V I I ) ~ R'''' ~X ~) ( VI I I ) R~ R' wherein X~ R', R'', R''' and R'''' are as described above.
Examples o X are alkylidene radicals such as methylene, ethylene and propylidene. Examples of R' and R'' are methyl lZ~9'~5~
and isobutyl. Examples of R''' and R'''' are butyl and octyl. Preferably used as the phenol derivative of formula V is a compound wherein X is fH3 --c--H
as the phenol derivative of formula VI is a compound wherein x is c~3 as the phenol derivative of formula VII is a compound wherein R'' is C4Hg , R''' is C8H17- and R
is C8H17 - or C4Hg- or a compound wherein R'' is C4Hg-, R''' is C4Hg- and R'''' is CH3- and as the phenol derivative of formula VIII is a compound wherein X is ~C-R' is CH3- and R'' is C4H9-.
Useful as alkylene oxides, from which the oxy-alkylene radisal derives, are al~ylene oxides containing 2 carbon atoms to 4 carbon atoms such as ethylene oxide, ~Z~Z5~
propylene oxide and butylene oxide. Useful in a preferred embodiment i9 ethylene oxide or a mixture of ethylene oxide and other alkylene oxides which when used in a mixture with ethylene oxide impart a hydrophilicity effective to self emulsify the compound. In lieu of the other alkylene oxides, other 3 or 4-carbon cyclic ethers such as tetrahydrofuran, oxetane, and methyl oxetane may be used.
Preferaby used are mixtures of ethylene oxide and propylene oxide.
The oxyalkylene is present in the fiber lubricant in an amount, as represented by n, such that the molecular weight of the compound is between 500 and 2500. Preferably used is a block of between 5 and 20 moles, such as 5, 10 or 15 moles of ethylene oxide per mole of phenol derivative.
Also preferably used is a heteric mixture of about 70 percent by weight oxyethylene and about 30 percent by weight oxypropylene.
Useful as fatty acids are those containing between 8 carbon atoms and 22 carbon atoms, preferably between 16 and 20 carbon atoms and more preferably 18 carbon atoms, such as isostearic acid.
The phenol derivative is ethoxylated by adding the phenol derivative and a basic catalyst to an autoclave evacuated to a vacuum and pressurized with nitrogen and equipped -~ith temperature, pressure and vacuum controls, and thereafter heated. The alkylene oxide is added at a ;~ constant rate until all the oxide is added. The reaction then proceeds at a temperature between 90C and 130C until a constant pressure is observed. Esterification is then ~23~9J~S'~
accomplished by adding approximately equal molar amounts of fatty acid and alkoxylated phenol derivative. Acid cata-lysts, such as methane sulfonic acid and hypophosphorus acid are added and the esterification reaction is allowed to proceed at a constant temperature, such as 165C under a nitrogen blanket.
The lubricants of this invention are applied to the fiber in an amount between 0.05 percent by weight and 5 percent by weight~ based on the weight of the lubricated fiber.
The lubricity of the products of this invention on synthetic yarns may be determined using any reasonable method One useful test method measures the lubricity, in units of the coefficient of friction, of nylon filaments having fiber lubricants applied to them at a concentration of about 1 percent lubricant by weight of filament by the procedure of the following two paragraphs.
A stable aqueous emulsion of the lubricant is prepared. This emulsion is applied to the yarn, such as nylon or polyester, using an apparatus in which the yarn is passed at a controlled speed through a continually replen-ished drop of finished solution or dispersion of specified concentration. A suitable apparatus is the ATLAS*yarn finish applicator sold by the Precision Machine and Develop-ment Company of Wilmington, Delaware. The lubricant * trademark _g_ dispersion is metered to the continually replenished drop of solution using a syringe pump. The yarn is fed over an adjustable canter roller which functions to space the yarn over a drying drum used to remove water. The yarn is finally passed over a winding tube and subsequently con-ditioned for 16 to 24 hours at 65 percent relative humidity and 70F before being tested.
The coefficient of friction (f~ may be determined on any suitable machine, such as a Rothschild F Meter utilizing 0.313 inch diameter ceramic (Al Si Mg) and satin chrome fric~on pins that has friction surface at a yarn contact angle of 180. The yarn speed is varied, such as at 50, 100, 150, 200, and 250 meters per minute. The yarn tension may be varied such as at 4 or 6 grams on the input side as determined by tensiometers by the Rothschild*F
meter. The (f) values are determined directly by reading the chart produced by the Rothschild*~ meter.
Viscosity may be determined by any standard procedure, such as using a~Brookfield*viscometer or Ubelohde*
tube Eollowing ASTM D444 71/79 or D2161-79. The viscosity of the fiber lubricants of this invention have a controlled viscosity range, from 500 to 1500 Saybolt universal sec-onds. A viscosity below this range i5 detrimental to processing the fibers and a viscosity above this range causes excessive add on to the fibers.
* trademarks ~`
~2~9~5~
Thermal and oxidative stability as well as non-volatility of the fiber lubricant may be tested by a number of suitable procedures such as the hot plate test, the circulating air oven test, dynamic thermogravimetric analysis and isothermal thermogravimetric analysis. The hot plate test proceeds by placing metal cups, 3 for each example, on a heater and maintaining the temperature at 240C for 24 hours. At intervals of time, the weight loss for each of the 3 samples is determined and averaged and the quality of residue determined. The hot plate test is representative of thermal stability as measured by the results at 240C for 24 hours and of oxidative stability by the quality of the residue. The circulating air oYen test proceeds as in the hot plate test except the hot plate and samples are placed in a circulating air oven. The thermo-gravimetric analyses proceed as follows: the dynamic thermogravimetric analysis measures the temperature in degrees centi~rade at which a specific percentage by weight, such as 1 percent by weight and 10 percent by weight, of the sample is lost in a test atmosphere, such as air or nitrogen, while heating the sample at a constant heating rate, such as 20 degrees per minute; and the isothermal thermogravimetric analysis measures the percent by weight loss of the sample at a constant temperature) such as 210C, for a specific time interval, such as 40 minutes, while the 5~
sample is continuously weighed.
The product stability of the fiber lubricant may be tested by any suitable method. The ability of the product of the invention to be storage stable is excellent.
The emulsification properties of the fiber lubricant may be tested by preparing a mixture containing 10 parts of fiber lubricant, 20 parts of mineral oil and 70 parts of water. The mixture is shaken vigorously and allowed to stand for 24 hours. If separation of the emulsion does not occur, the emulsion is considered stable.
The products of a preferred embodiment of the invention are self emulsifiable with water and do not require additives to make an emulsion.
Additional additives may, however, be added to the fiber lubricants in preparing fiber lubricant formula-tions. These additives are described in U.S. 4,134,8417 ~2~9~S~
The followin~ examples will further illustrate the various aspects of the invention. Where not otherwise specified throughout the specification and claims, temper-atures are in degrees Centigrade, and parts, percentages and proportions are by weight.
Example 1 To an autoclave e~uipped with temperature, pressure, and vacuum controls was added 780 parts of butylated, styrenated cresol (WINGSTAY~ V - Goodyear Company) and 8 parts of 45 percent potassium hydroxide solution. The autoclave was heated to 125C after evacu-ating to a vacuum of less than 10 millimeters mercury and then pressurizing to 34 lbs./square inch with nitrogen.
Ethylene oxide was added at a rate of 250 parts/hour until 1921 parts were added. When constant pressure was observed, the catalyst was removed by deionization and the mixture was further stripped to remove volatiles. This ethoxylate, Example lA, had a hydroxyl number of 66.2 and a viscosity of 883 Saybolt universal seconds at 100F.
To a 2 liter flask having temperature control, stirrer and distillation apparatus were added 891 parts of the above ethoxylate. Next, 279.1 parts of isostearic acid, 4.12 parts of methanesulfonic acid, (70 percent), and 4.0 parts of hypophosphorous acid were added. The temperature was held at a constant 165C in a nitrogen atmosphere until s~
the esterification reaction was complete. After catalyst removal, the product of Example 1 of this invention, the isostearate ester of ethoxylated butylated styrenated cresol, a specific product containing compounds of formula IV above, was obtained having a hydroxyl number of 4.4, an acid number of 1.56 and a viscosity of 781 Saybolt universal seconds at 100F.
Comparison Examples A, B, C and D
A is a polyoxypropylene block adduct of a polyoxy-ethylene adduct of ethylene glycol of approximate average molecular weight of the hydrophobe of 1000 and an oxy-ethylene content of about 50 percent by weight.
B is a polyoxyethylene block adduct of a polyoxy-propylene adduct of propylene glycol of approximate average molecular weight of the hydrophobe of 950 and an oxyethylene content of about 50 percent by weight.
C is a heteric ethylene oxide propylene oxide adduct of a C12-C15 fatty alcohol, having an overall approximate average molecular weight of 1280 and containing about 50 percent ethylene oxide.
D is a polyoxyethylene block adduct of a polyoxy-propylene adduct of bisphenol A of approximate average overall molecular weight of 8350 and an oxyethylene content of about 80 percent by weight.
~z~s~æs~
Lubricity, heat stability and emulsion properties were obtained as follows: An aqueous emulsion of the lubricant of Example 1 was prepared. This emulsion was applied to yarn using an Atlas yarn finish applicator. The coefficient of friction (f) was determined on a Rothschild F
meter utili~ing 0.313 inch diameter ceramic (Al Si Mag) and satin chrome friction pins as the friction surface at a yarn contact angle of 180. The ASTM procedure Standard Test Method for Coefficient Friction, Yarn to Metal Designation 03108-76 was generally followed. The lubricity results, using 40/12 denier nylon 6 yarn, are shown in Table I for ; the products of Example 1 and comparison Example A.
TABLE I
Input Speed Coefficient of Friction Tension Meters/ Example 1Comparison Example A
(Grams)Minute f f 4 50 .70 .73 4 100 .71 .76 4 150 .71 .77 4 200 .71 .77 6 50 .64 .67 6 100 .66 .69 6 150 .67 .70 6 200 .67 .71 Thermal and oxidative stability of the products of Example 1 and comparisons B and C, using a hot plate set at 240C and 3 gram samples, are shown in Table II.
-lS-9~5~
TABLE II
Heat Stability Hot Plate Test Percent Residue ExampleAfter 24 Hours Nature of Residue 1 76.7 Light brown liquid B 2.9 Varnish C 38.8 Dark Brown Liquid Heat stability results for the products of Example 1 and Comparison Example C, using a circulating air oven set at 210C and 3 gram samples, are shown in Table ; IIIo TABLE III
Heat Stability Circulating Air Oven Test Percent Residue ExampleAfter 24 Hours Nature of Residue 187.6 Light Brown Liquid C22.9 Dark Brown Liquid Heat stability results for the product of Example 1 of the invention using thermogravimetric analysis and isothermal percent weight loss are shown in Table IV.
!L9'2~
TABLE IV
Thermogravimetric Analysis Dynamic C Weight Loss of 1% 10% 50%
Example Air/ N2 Air/ N2 Air/N2 Isothermal ~ Weight Loss Smoke Point at 210C -40 Minutes C
1 18.0/4~0 187 Stable emulsions, made with the product of Example 1, and water and with the product of Example 1, water and other materials are shown in Table V.
~'~19%S'~
TABLE V
Emulsions Stable Emulsion Component parts parts parts parts Product of Example 1 12 5 2 20 Tridecyl Stearate36 - - -Butyl Stearate - 15.0 Mineral Oil - - 8 (Crystosol TW) KLEARFAC~ A270 - 3 ~neutralized) Water 52 77 90 80 , ~2~ 5~
Examples 2-20 Examples 3-10 and 14-19 were prepared using the procedure to prepare Example lA. Examples 2, 11-13 and 20 were prepared using the procedure for preparing the product of Example 1. EO is ethylene oxide, PO i5 propylene oxide, product Yl is a commercial product of formula V wherein X is -- C -- , H
(WINGSTAY~ S - Goodyear Company), product Y2 is a commer-cial product of formula VII wherein R" is C4Hg-, ~"' is C8H17- and R"" is either C4Hg- or C8H17-(WINGSTAY~ T - Goodyear Company) and product Y3 is a commercial product of Eormula VI wherein X is -- C --and R" is C~Hg- (WINGSTAY~ C - Goodyear Company).
9~5~
The products are as follows:
Example Composition 2 Laurate ester of Example LA
3 5 mole ethoxylate of the butylated styrenated cresol of Example 1
4 10 mole ethoxylate of the butylated styrenated cresol of Example 1
5 EO adduct of product Y
6 10 EO ~
7 15 EO "
8 70/30 EO/PO "
9 11 PO ~ 9 EO + 11 PO "
25 EO "
11 isostearate ester of Example 7 12 isostearate ester of Example 10 13 isostearate ester of Example 9 14 5 EO adduct of product Y2
25 EO "
11 isostearate ester of Example 7 12 isostearate ester of Example 10 13 isostearate ester of Example 9 14 5 EO adduct of product Y2
10 EO "
16 15 EO "
17 5 EO adduct of product Y3 18 10 EO "
19 15 EO "
the isostearate ester of Example lA
The physical properties of the fiber lubricants of Examples 2-20 are shown below in Table VI.
_ ble VI
ExampleMolecular HydroxylViscosity Weight No.SUS at 100F
2 1047 7~6 905 3 467 120 ~ 2 1406 4 680 82. 5 936 504 111 ~ 2 1570 6 742 75~6 1111 7 946 59~3 1088 8 1465 38~ 3 1320 9 1556 36~1 1243 1320 42~ S 1657
16 15 EO "
17 5 EO adduct of product Y3 18 10 EO "
19 15 EO "
the isostearate ester of Example lA
The physical properties of the fiber lubricants of Examples 2-20 are shown below in Table VI.
_ ble VI
ExampleMolecular HydroxylViscosity Weight No.SUS at 100F
2 1047 7~6 905 3 467 120 ~ 2 1406 4 680 82. 5 936 504 111 ~ 2 1570 6 742 75~6 1111 7 946 59~3 1088 8 1465 38~ 3 1320 9 1556 36~1 1243 1320 42~ S 1657
11 1200 6~0 974 1~ 1580 6~ 5 1320 13 1800 10~0 1162 14 576 97~ 4 1470 695 80 r 7 1159 20 16 1578 71.1 981 17 610 91~9 25g9 18 851 65~ 9 1139 19 1024 54~ 1094 1134 12~ 8 1096 Thermal properties of heat resistant lubricants of the invention and comparison Example B, determined in an aluminum pan test on a hot plate set at 240C are shown in Table VII.
5'~
Table VII
Example rcent Residue, Hours Appearance*
0.5 2 4 8 24 2 99.4 98.6 97.0 93.3 78.2 b 3 97.8 93.6 89.1 82.7 76.1 b 4 99.6 97.6 95.0 89.4 71.9 b 99.3 97.3 95.2 91.6 86.1 a 6 99.8 99O3 98.8 97.6 93.0 b 7 99.7 99.2 97.9 94.8 84.5 b 8 99.5 98.3 95.9 90.7 80.4 b 9 98.7 95.0 89.6 79.2 62.9 b 14 92.9 85.2 79~6 72.1 61.0 b 98.9 96.7 94~3 89~0 64.8 b 16 97.6 95.7 93~3 88.4 65.5 b 17 94.1 88.8 85.5 78.9 71.0 b 18 95.9 93.0 90.0 83.7 57.0 b 19 96.6 94.9 92.3 86.2 65.0 b B 97.3 80.8 41.4 6.6 2.4 c * a-brown b-light brown c-varnish Thermal properties of heat resistant lubricants of the invention and comparison examples B and D as determined in an aluminum pan in an air circulating oven at 210C are shown below in Table VIII.
Iable VIII
Example Percent Residue, ~urs pearance*
0.5 2 4 8 24 2 98.1 90.3 78.8 60.7 4002 d 7 98.4 92.4 85.4 75~7 52.3 a 9 94.0 73.6 56.4 37.5 16.9 d 98.1 87.5 76.1 62.7 37.0 d 11 96.6 91.9 86.4 78.4 56.4 d
5'~
Table VII
Example rcent Residue, Hours Appearance*
0.5 2 4 8 24 2 99.4 98.6 97.0 93.3 78.2 b 3 97.8 93.6 89.1 82.7 76.1 b 4 99.6 97.6 95.0 89.4 71.9 b 99.3 97.3 95.2 91.6 86.1 a 6 99.8 99O3 98.8 97.6 93.0 b 7 99.7 99.2 97.9 94.8 84.5 b 8 99.5 98.3 95.9 90.7 80.4 b 9 98.7 95.0 89.6 79.2 62.9 b 14 92.9 85.2 79~6 72.1 61.0 b 98.9 96.7 94~3 89~0 64.8 b 16 97.6 95.7 93~3 88.4 65.5 b 17 94.1 88.8 85.5 78.9 71.0 b 18 95.9 93.0 90.0 83.7 57.0 b 19 96.6 94.9 92.3 86.2 65.0 b B 97.3 80.8 41.4 6.6 2.4 c * a-brown b-light brown c-varnish Thermal properties of heat resistant lubricants of the invention and comparison examples B and D as determined in an aluminum pan in an air circulating oven at 210C are shown below in Table VIII.
Iable VIII
Example Percent Residue, ~urs pearance*
0.5 2 4 8 24 2 98.1 90.3 78.8 60.7 4002 d 7 98.4 92.4 85.4 75~7 52.3 a 9 94.0 73.6 56.4 37.5 16.9 d 98.1 87.5 76.1 62.7 37.0 d 11 96.6 91.9 86.4 78.4 56.4 d
12 96.9 91.2 83.4 70~3 42.3 d
13 98.4 81~3 65.1 48.0 ?6.8 d B 67.0 1.7 1.1 - - c D 98.0 87.1 77.4 68.3 51.2 d * a - brown c - varnish d - dark brown
Claims (11)
1. A fiber lubricant formulation comprising at least one lubricant in admixture with one or more standard lubricant formulation additives, wherein said at least one lubricant is a compound selected from the group consist-ing of:
(I) (II) (III) (IV) wherein A is an oxyalkylene radical having 2 carbon atoms to 4 carbon atoms or mixtures thereof, R is hydrogen or acyl containing from 8 carbon atoms to 22 carbon atoms, R' is alkyl containing from 1 carbon atom to 10 carbon atoms, R"
is alkyl containing from 1 carbon atom to 22 carbon atoms, R''' is alkyl containing from 4 carbon atoms to 8 carbon atoms, and R'''' is R" or R''', X is an alkylidene radical containing from 1 carbon atom to 3 carbon atoms, and n is an integer such that the molecular weight of the compound is between 500 and 2500 and with the proviso that either R" or R''' is ortho to the oxygen in formula III.
(I) (II) (III) (IV) wherein A is an oxyalkylene radical having 2 carbon atoms to 4 carbon atoms or mixtures thereof, R is hydrogen or acyl containing from 8 carbon atoms to 22 carbon atoms, R' is alkyl containing from 1 carbon atom to 10 carbon atoms, R"
is alkyl containing from 1 carbon atom to 22 carbon atoms, R''' is alkyl containing from 4 carbon atoms to 8 carbon atoms, and R'''' is R" or R''', X is an alkylidene radical containing from 1 carbon atom to 3 carbon atoms, and n is an integer such that the molecular weight of the compound is between 500 and 2500 and with the proviso that either R" or R''' is ortho to the oxygen in formula III.
2. The fiber lubricant formulation of claim 1, wherein A is oxyethylene.
3. The fiber lubricant formulation of claim 1, wherein A is a mixture of oxyethylene and an alkylene oxide containing 3 carbon atoms to 4 carbon atoms, said A imparting a hydrophilicity effective to self emulsify the compound.
4. The fiber lubricant formulation of claim 2, wherein the compound is of formula IV, R is an acyl radical containing 18 carbon atoms, R' is methyl, R" is C4H9-, and X is
5. The fiber lubricant formulation of claim 4, except that A is a heteric mixture of about 70 percent by weight ethylene oxide and about 30 percent by weight propylene oxide.
6. The fiber lubricant formulation of claim 2, wherein the compound is of formula I, R is an acyl containing 18 carbon atoms and X is and n is about 15 to about 25.
7. The fiber lubricant formulation of claim 2, wherein the compound is of formula II, R is an acyl containing 18 carbon atoms, and X is
8. The fiber lubricant formulation of claim 1, 2 or 3, wherein the standard lubricant formulation additives are selected from the group consisting of emulsifiers, antistatic agents, antioxidants, bacteriocides, friction modifiers, buffering agents and mixtures thereof.
9. A process of lubricating synthetic fibers which comprises applying to the fiber, in an amount between 0.05 percent by weight and 5 percent by weight, based on the weight of lubricated fiber, a compound selected from the group consisting of:
(I) (II) (III) and (IV) wherein A is an oxyalkylene radical having 2 carbon atoms to 4 carbon atoms or mixtures thereof, R is hydrogen or acyl containing from 8 carbon atoms to 22 carbon atoms, R' is alkyl containing from 1 carbon atom to 10 carbon atoms, R"
is alkyl containing from 1 carbon atom to 22 carbon atoms, R''' is alkyl containing from 4 carbon atoms to 8 carbon atoms, and R'''' is R" or R''', X is an alkylidene radical containing from 1 carbon atom to 3 carbon atoms, and n is an integer such that the molecular weight of the compound is between 500 and 2500 and with the proviso that either R"
or R''' is ortho to the oxygen in formula III.
(I) (II) (III) and (IV) wherein A is an oxyalkylene radical having 2 carbon atoms to 4 carbon atoms or mixtures thereof, R is hydrogen or acyl containing from 8 carbon atoms to 22 carbon atoms, R' is alkyl containing from 1 carbon atom to 10 carbon atoms, R"
is alkyl containing from 1 carbon atom to 22 carbon atoms, R''' is alkyl containing from 4 carbon atoms to 8 carbon atoms, and R'''' is R" or R''', X is an alkylidene radical containing from 1 carbon atom to 3 carbon atoms, and n is an integer such that the molecular weight of the compound is between 500 and 2500 and with the proviso that either R"
or R''' is ortho to the oxygen in formula III.
10. The process of claim 9, wherein the compound is applied as such to the fiber.
11. The process of claim 9, wherein A in the definition of the compound is oxyethylene and said compound is applied to the fiber in the form of an emulsion with water.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36240882A | 1982-03-26 | 1982-03-26 | |
| US362,408 | 1982-03-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1219252A true CA1219252A (en) | 1987-03-17 |
Family
ID=23426011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000424456A Expired CA1219252A (en) | 1982-03-26 | 1983-03-25 | Fatty acid esters of phenol derivative alkoxylates and their use as fiber finish components |
Country Status (2)
| Country | Link |
|---|---|
| EP (1) | EP0090273A3 (en) |
| CA (1) | CA1219252A (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3578594A (en) * | 1967-11-24 | 1971-05-11 | Diamond Shamrock Corp | Fiber treating compositions |
| US4134841A (en) * | 1978-03-10 | 1979-01-16 | Union Carbide Corporation | Fiber lubricants |
-
1983
- 1983-03-17 EP EP83102632A patent/EP0090273A3/en not_active Withdrawn
- 1983-03-25 CA CA000424456A patent/CA1219252A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0090273A2 (en) | 1983-10-05 |
| EP0090273A3 (en) | 1986-01-08 |
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