Poly (ethylene oxide) adducts of fatty oils and fatty amines as antistatic coating for polyolefin fibers

United States Patent Office _{Patented Ja}i , ’_lM7 oil, corn oil, coconut oil, soya bean oil, palm oil, perilla oil, tallow, whale oil, bone oil, etc. If desired, these oils may be partially hydrogenated to increase saturation and vary the melting range thereof.

The fatty oils are reacted with ethylene oxide to obtain polyethylene oxide adducts of the fatty oil. The adducts generally have an average or from about 15 to 40 or more ethylene oxide units per glycerine molecule in the fatty oil and preferably from 20 to about 30 ethylene oxide units per molecule.

The fatty acid primary amines of this invention are preferably derived from the amination of fatty acids or a mixture of fatty acids obtained from the distillation of the products of hydrolysis of the above described fatty oils. The Ci₂-C₁₈ fatty acids include, for example, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, etc. Mixtures of these acids, for example those obtained from tallow oil, namely, stearic, palmitic and oleic, are as good or better than individual fatty acids for the purposes of this invention. The fatty acid primary amines are reacted with ethylene oxide to obtain polyethylene oxide adducts of the fatty acid amines wherein each fatty amine molecule has attached thereto a chain having an average of from about 10 to 30' and more ethylene oxide units and preferably from about 15 to 25 ethylene oxide units per molecule of fatty amine.

Many lubricant-antistat combinations were investigated to develop a satisfactory finish composition for polyolefin fiber. Before combinations of lubricants and antistats were tried, however, a screening test was conducted to determine whether the lubricant or antistat material would degrade the polyolefin. Screening involved placing approximately 0.2 ml. of the liquid lubricant or antistat onto a sheet of polypropylene film which has been secured to a glass plate. A piece of graph paper was placed between the film and the glass and served two purposes; it would indicate penetration of the film by the liquid, and also give an indication of the spreading action of the lubricant or antistat. The material passed the screening test if 24 hours of film contact produced no change in film appearance such as waviness or puckering. If puckering did occur it was assumed that it was caused by penetration of the lubricant or antistat into the film and this type of behavior would also occur with a polypropylene fiber. Puckering was considered to be caused by plasticization or a similar phenomenon and test materials causing it were rejected.

The above screening test indicated that paraffinic oils and low molecular weight esters had a noticeable undesirable effect on the test film. Applications of these materials to polyolefin yarn at spinning and the consequential softening or plasticization of this yam corroborated the screening test results.

To demonstate the specificity of this invention there is set forth in the following table a list of finishes, the components of which have passed screening tests but which have been found unsatisfactory either in their application or in their ability to improve characteristics of the yarn.

3,296,019

POLYETHYLENE OXIDE) ADDUCTS OF FATTY OILS AND FATTY AMINES AS ANTISTATIC COATING FOR POLYOLEFIN FIBERS 5

Ann S. Keller, Norristown, and Harry H. Hall, Springfield, Pa., assignors, by mesne assignments, to FMC Corporation, San Jose, Calif., a corporation of Delaware

No Drawing. Filed Apr. 19, 1962, Ser. No. 188,838 10

Claims. (Cl. 117—138.8)

This invention relates to finished polyolefin fibers. More particularly, it relates to* polyolefin yarns or fibers having applied finishes which enable the yarns to be satis- ¹⁵factorily processed and utilized in the commercial production of textiles and in machine sewing operations.

Polyolefin yams, for example polypropylene and polyethylene yarns, tend to develop high electrostatic charges 20 and excessive tensions when running over guides, godets and other objects during processing and subsequent handling. The utilization of unfinished polyolefin yarns in textile production and sewing equipment is unsatisfactory.

Static and tension problems have been encountered in the use of other natural and synthetic polymer yams, and finishes which are satisfactory from both the standpoints of application and use have been developed for them. However, the polyolefins have different physical charac- 30 teristics than most other filament forming polymers and conventional finishes and methods for application thereof are not suitable or effective in providing the necessary fiber to fiber lubrication, proper fiber to metal frictional behavior, and adequate static suppression.

The primary object of this invention is to provide a finished polyolefin yarn which is suitable for high speed processing, textile and sewing operations.

It is another object of this invention to provide a meth- 40 od of finishing polyolefin fibers which is effective in providing fiber lubrication and static suppression.

These and other objects are accomplished in accordance with this invention with a finish composition for polyolefin fibers comprising from about 10' to about 30% 45 by weight of a finish consisting essentially of 1 to 5 parts by weight of a polyethylene oxide modified fatty oil and 1 part by weight of a polyethylene oxide modified C₁₂-Ci₈fatty acid primary amine, and from about 90 to 70% by weight of water. This finish composition is applied to polyolefin yarns including, for example, polyethylene, polypropylene and polyisobutylene yarns or fibers by any known means including bath, spray, padding, kiss roll application or the like. 55

Generally speaking, water base finish compositions are unsatisfactory for application to polyolefin yarn or fibers because of the hydrophobic nature of these polymers. The present finish composition, however, is an exception θθ and provides unexpectedly good lubrication and static suppression.

The fatty oils of the invention include, for example, castor oil, cotton seed oil, flax seed oil, olive oil, peanut

3,296,019

TABLE I

Percent By Weight

No.

Finish Composition

<td> 1 _______ 2________ 3________ 4________ 5________</td><td> Diethyl cyclohexylamine salt of lauryl sulfate----------------- Coconut oil___________________________________________________ Diethyl cyclohexylamine salt of lauryl sulfate----------------- Sorbitan monooleate__________________________________________ Butyl stearate_________________________________________________ Diethanolamine salt of dilauryl phosphate____________________ Sorbitan monooleate__________________________________________ Butyl stearate--- ____________________________________________ l-hydroxyethyl-2-oleyl ethyl glyoxolinium ethosulfate--------- Sorbitan monooleate------------------------------------------ Butyl stearate___________________________;--------------------- Sorbitan monooleate__________________________________________ Butyl stearate_________________________________________________</td>

<td> 6________ 7________ 8________ 9________ 10_______ 11_______</td><td> l-hydroxyethyl-2-oleyl ethyl glyoxolinium ethosulfate--------- Sorbitan monooleate__________________________________________ Coconut oil__________________________________________________- l-hydroxyethyl-2-oleyl ethyl glyoxolinium ethosulfate--------- Sorbitan trioleate_____________________________________________ Esterified pentaerythritol_____________________________________ Diethyl cyclohexylamine salt of lauryl sulfate----------------- Water_________________________________________________________ Diethyl cyclohexylamine salt of lauryl sulfate----------------- Diethylene glycol_____________________________________________ Deithyl cyclohexylamine salt of lauryl sulfate----------------- Polyethylene glycol (M.W. 400) monooleate------------------- Diethyl cyclohexylamine salt of lauryl sulfate_________________ Dialiphatic ether of polyethylene glycol_______________________</td>

<td> 12_______ 13_______ 14_______</td><td> Esterified pentaerythritol_____________________________________ Nonionic emulsifying agents---------------------------------- Finish No. 12---______________________________________________ Water_________________________________________________________ Finish No. 12_________________________________________________ Sorbitan monooleate__________________________________________</td>

<td> 15_______ 16_______ 17_______ 18--.-.- 19_______ 20_______ 21_______ 22_______ 23_______ 24_______ 25_______ 26_______</td><td> N-cetyl N-ethyl morpholinium ethosulfate--------------------- Finish No. 14_________________________________________________ Water_________________________________________________________ N-cetyl N-ethyl morpholinium ethosulfate____________________ Technical grade octanol_______________________________________ N-cetyl N-ethyl morpholinium ethosulfate____________________ Water_________________________________________________________ N-cetyl N-ethyl morpholinium ethosulfate____________________ Diethylene glycol_____________________________________________ N-cetyl N-ethyl morpholinium ethosulfate-------------------- Finish No. 12_________________________________________________ Polyoxyethylene modified tallow aeld primary amine--------- Polyethylene glycol (M.W. 200) monolaurate__________________ Polyethylene glycol (M.W. 200) monopelargonate-------------- Polyethylene glycol (M.W. 1000) monostearate---------------- Polyethylene glycol (M.W. 200) monopelargonate______________ Diethanolamine salt of dilauryl phosphate-------------------- Finish No. 22_________________________________________________ Diethanolamine salt of dilauryl phosphate____________________ Polyethylene glycol (M.W. 200) monopelargonate-------------- Polyethylene glycol (M.W. 400) monopalmitate________________ Water_________________________________________________________ Diethanolamine salt of dilauryl phosphate____________________ Polyethylene glycol (M.W. 200) monolaurate__________________</td>

3-5 95-97 3-10 1.5-5 85-95.5

4

3 3

5

3 4

5

75 10 90

90

95

95 60 40 10 90 95

2

80

95

90

90

98

95

100

98

95 10 90

98

90

In addition to the above yarn finish compositions, many other unsatisfactory combinations were tested Which were identifiable only under chemical trade names and/or broad chemical terms.

Polyolefin fibers and in particular polypropylene fibers are much more difficult to finish than other synthetic or natural polymer fibers. They are non-polar materials and as such have no affinity for the usual yarn finishes. They are hydrophobic, and in general, water base finish compositions cannot 'be used to obtain a satisfactory finish. The polyolefin fibers are degraded by treatment with hydrocarbon oil base compositions and become undesirably soft. For these reasons, the finish composition is extremely critical in order to obtain satisfactory yam characteristics.

The following examples are set forth to demonstrate finish application and composition in accordance with the invention.

Example I

A mixed composition of 2 parts of the polyethylene oxide adduct of hydrogenated castor oil having an average of 25 ethylene oxide units per glyceride molecule of the castor oil and 1 part of the polyethylene oxide adduct of primary amines prepared from fatty acids derived from tallow oil having an average of 20' ethylene oxide units per molecule of fatty amine, was mixed with water at a concentration of 20% by weight. Then, the finished solution was applied to polypropylene ap50 proximately 800 denier, 34 filament yarn by means of a kiss roll 6 inches in diameter and 1½ inches wide just prior to primary take-up. The finished yarn was collected onto a standard take-up tube with ease. The finish was also found to be an aid in processing the yarn through a draw-twisting unit.

Example II

A finish was prepared and applied to polypropylene fiber as described in Example I except that 4 parts of the polyethylene oxide adduct of hydrogenated castor oil were used instead of 2 parts and the combination was mixed with water at a concentration of 15'% by weight. The fiber was found to have even better processing properties than the finished yarn of Example I.

Various changes and modifications may be made in practicing the invention without departing from the spirit and scope thereof and, therefore, the invention is not to be limited except as defined in the appended claims.