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Publication numberUS2839464 A
Publication typeGrant
Publication dateJun 17, 1958
Filing dateFeb 16, 1954
Priority dateFeb 16, 1954
Also published asDE1053139B
Publication numberUS 2839464 A, US 2839464A, US-A-2839464, US2839464 A, US2839464A
InventorsJames H Norton, Lorne W Sproule
Original AssigneeExxon Research Engineering Co
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Textile oil
US 2839464 A
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Description  (OCR text may contain errors)

United States 2,839,464 TEXTILE OIL Lorne W. Sproule, Sarnia, Ontario, and James H. Norton, Corunna, Ontario, Canada, assignors to Esso Research and Engineering Company, a corporation of Delaware N0 Drawing. Application February 16, 1954 Serial No. 410,738

1 Claim. (Cl. 252-83) The present invention relates to an improved textile oil and to an improved method of treating certain textile materials prior to dyeing. More particularly, the invention is concerned with an improved textile oil which affords effective lubrication in all textile processing operations and which may be readily removed by scouring prior to dyeing.

In brief compass, the invention pertains to a mineral oil base textile oil which contains dissolved therein small amounts of. three non-ionizing components, to Wit a detergent, an emulsifying agent and a coupling agent, which have a synergistic effect on the solution stability, emulsion stability and scouring efficiency of the oil. The

textile oil of the invention has particular utility in the treatment of certain raw animal fibres, such as raw wool, containing substantial proportions of lime or other alkaline metal compounds reacting with anionic materials to form salts of low water solubility.

The textile oils most commonly used heretofore are based on various fatty oils of animal or vegetable origin. These oils are rather expensive and readily oxidizable. Mineral oils which are superior with respect to availability and oxidtaion resistance cannot be used as such because they are diificult to remove from the finished textiles by conventional scouring with Water containing soap and soda ash.

Many suggestions have been made prior to the present invention to improve the utility of mineral oils for textile treating purposes by means of various modifying agents. Most of these improved oils contain ionizing emulsifiers or detergents of the metal sulfonate type alone or together with certain other emulsifier, rust preventives, Wetting or surface active agents, such as sorbitan esters of fatty limed wool is normally used. This W001, which is removed from the animal hides with the aid of a depilatory agent such as lime, contains-large quantities of free lime. Textile oils and scouring baths used in. the manufacture of fabrics from this type of wool must be lime resistant. Conventional textile oils and scouring baths are greatly deficient in this respect. The calcium ions present in the raw wool react with the anions of sodium sulfonates and other soaps'of conventional Wool oils and with anions of the soaps of the scouring baths to form Water-insoluble soaps and salts. These insoluble compounds are adsorbed on the W001, forming a curd or scum which resists subsequent scouring and seriously interferes with the dyeing process. Similar complications arise when hard water is used in scouringall types of textiles treated WithiBXtlle oils containing constituents which ionize in aqueous solutions to yield anions formingwater-insoluble compounds with calcium or thelike. The, present invention-oven atent Thirdly, the oil must be easily removable by scouring I with distilled and hard water scouring baths.

It has now been found that all these requirements are adequately met by a mineral base textile oil which is substantially free of constituents ionizing in aqueous solutions to yield ions forming compounds of low water solubility with calcium or the like and which contains small proportions of three non-ionizing oil-soluble components acting as a detergent, an emulsifier and a coupling or stabilizing agent, respectively. These three non-ionizing components have a synergistic effect upon each other and the mineral oil base with respect to their oil solubility, the detergency and the emulsion stability of the finished textile oil.

Compounds suitable as the detergent component of the textile oil of the invention are the polyglycol esters of unsaturated high molecular weightfatty acids having the general formula wherein R is an unsaturated aliphatic radical having 14-22 carbon atoms, more specifically 16-18 carbon atoms, n is an integer of from 2-6, more specifically 2-4, and x is an integer offrom about 5 to about 30, more specifically 5-15. In accordance with the preferred embodiment of the invention, R is the hydrocarbon radical of oleic acid, 11 is 2 and x averages about 13. A product of this type is now on the market under the trade name Antarox Agent 377-AE (Chemical Developments of Canada Ltd.; General Dyestuif Corp. U. S. A.). These products are probably mixtures composed chiefly of the mono-ester with some di-ester present. A concentration of about 0.5-20 wt. percent, preferably about 5-15 Wt. percent, of this component, based on mineral oil, may be used. i

The emulsifier component of the textile oil of the invention is a polyether alcohol of the general formula wherein R is an aryl, aralkyl or saturated or unsaturated alkyl group having 10-20, more specifically 14-16, carbon atoms, n is an integer of 2-6, more specifically 2-4, and x is an integer averaging about 2-20, more specifically 2-6. The preferred-emulsifiers are alkyl-aryl polyether alcohols in which R is essentially nonyl phenyl, n is 2 and x averages about 4%. A product of this type is on the market under the trade name Triton X-45 (Rohm and Haas Co.) which is essentially an alkylated aryl polyetheralcohol having the general formula r of the latter.

The coupling or stabilizing agent of the textile oil of the invention is an oil-soluble unsaturated fatty acid partial ester of a higher polyhydric alcohol of the type disclosed in the MacLaurin Patent No. 2,404,240. The preferred coupling agent of the invention is sorbitan mono-oleate which may be used in concentrations of about 1-10 wt. percent, preferably about 2-6 wt. percent, based on mineral oil. The concentration of the coupling agent in the finished textile oil should likewise be substantially below that of the detergent component and should not exceed about 50% of the latter.

In general, it has been found desirable to add a small 4 (Triton X-45) and the coupling agent was sorbitan mono-oleate.

The difierent textile oils were tested for their solution stability and emulsion stability as follows. The solution stability was tested, storing the freshly prepared samples in sealed glass bottles at room temperature and observing visually the degree of separation after 1, 7 and 30 days of storage. The emulsion stability was measured by adding 10 mls. of oil to 90 mls. of the proportion of about 0.05-2 wt. percent, preferably less 10 test water in a glass stoppered graduate, shaking for 1 than 1 Wt. percent, say about 0.5-0.8 wt. percent, of minute and then allowing the solution to standfor 24 water to the textile oil. Such small amounts of water hours. The number of mls. of oil or cream separating cooperate with the coupling agent in increasing the from the emulsion within this time was recorded. The compatibility of the other components with the mineral composition and properties of the oils tested are sumil b 15 marized in Table I below.

Table I Designation B21 B-7 13-23 13-22 13-1 13-20 13-16 13-8 B-B B910 Formula, weight percent: Antarox agent377-AE l 6 6. 5 8 10 11.3 12. 5 15 10 10 Triton X45; 3 3 3 3 3 3 3 3 1. 5 4. 5 Sorbitan mono-o1eate 4 4 4 4 4 4 4 4 4 4 er 0.7 0.7 0.7 0.7 0.7 0.7 0.7 0.7 0.7 0,7 Mineral oil 01. 3 87. 3 85.8 84. 3 82. 3 81. 79. 8 77. 3 83. 8 8018 Solution stability:

1 day at room temp Clear Clear Clear Clear Clear Clear Sep. Sep. Clear Clear 7 days at room temp Clear Clear Clear Clear Clear Scp. Clear Clear 30 days at room temp Clear Clear Clear Clear Clear Clear Clear Emulsion stability (cc. sep'n./24 hrs):

Dist. water 15 0 0 0 0 0 2 0' 300 p. p. in. hard water. 13 4 0 0 0 0. 0 600 p. p. in. hard water". 10 15 0 0 0 0 0. 1,200 p. p. in. hard water 0 Designation B-l7 B-4 13-5 B15 3-13 13-11 B-14 13-3 13-2 Formula, weight percent:

Antarox agent 377-AE 10 10 10 10 10 10 5 Triton X 6 3 3 3 3 3 1.5 6 Sorbitan mono-cleats. 4 4 2 2 8 \Vatep 0. 7 0. 7 0. 7 0. 35 It Mincral 01L 79. 3 90 97 87 83 84. 3 86.3 91. 1 64.5 Solution stabilit 1 day at room temp Sep 1 Sep 1 Hazy Sep. Sep Sep. Sep. Sep Clear 7 days at room temp l Hazy Clear 30 days at room temp Clear Emulsion stability (on. sepn./24 hrs):

Dist. water a o 300 p. p. m. hard water 0 600 p. p. in. hard water..-" .0' 1,200 p. p. in. hard Water 1 0.7% water does not clarify solutions. 1 Almost transparent emulsion.

The mineral oil base of the textile oil of the invention It will be seen from the above data that stable soluinay be any mineral oil distillate havinga viscosity of tions are formed using from 1-10 wt. percent of the about -200 SSU at 100 F. Relatively light oils obtained from naphthenic or paraffinic base stocks, such as Mid-Continent crudes and having a viscosity of about 75-150 SSU at 100 F. and a viscosity index of about 50-100 are preferred. I

' The invention will be further illustrated by the following specific examples.

EXAMPLE I detergent of the invention (Antarox Agent-377-AE)'at constant concentrations of emulsifier (Triton X-45), coupling agent (sorbitan mono-oleate) and water at 3 wt. percent, 4 wt. percent and 0.7 wt. percent, respectively (Formulae B-21, B-7, B-23, B-22 and B-1). Formulae B-9 and 3-10 show that a range of from 1.5-4.5 wt. percent of the emulsifier used forms stable solutions for given concentrations of the other ingredients. A stable solution was also formed when the concentration of the ingredients of Formulae B-l were doubled as shown in Formula B-2.

It is also significant that the detergent and emulsifier were not soluble in the mineral oil either alone or together, as shown in Formulae B-4, B-5, and B-IS. However, these components become soluble in the presence of the coupling agent of the invention as shown by the other formulae.

The above data also show that stable emulsions as well as stable solutions are obtained in accordance with the invention. This is demonstrated by Formulae B-1 and 3-2 for a wide range of component concentrations. Formulae B-9 and B-10 show that stable emulsions are obtained at emulsifier concentrations as low as 1.5 wt.

percent and as high at 4.5 wt. percent in oilsof the type of Formula B-l.


Two textile oils of the type of Formula B-l of Example I were prepared as described in Example I with the exception that the detergent of one oil was a polyglyeol ester of oleic acid containing moles of ethylene oxide per mole of acid (Antarox Agent 377-BK) and the detergent of the other, oil was a polyglycol ester of oleic acid containing 8 moles oiethylene oxide ,per mole of acid (Antarox Agent 377-LE). The mineral oil was the same as that used in Example I. These oils were tested as described in Example I. The composition and properties of these oils are compared with those of Formula 3-1 in Table II below.

Table II Designation 3-18 3-19 B-l Formula. weight percent:

Antarox agent I3177-13 K. 10...

Triton X-45 3. Sorbitan mono-cleats 4 4. Water 0.7. Mineral oil 82.3 82.3... 82.3. Solution stability:

1 day at room temperature. Hazy Clear Clear 7 days at room temperature S1. hazy .-do. Do.

30 days at room temperature slhsepara- .do Do.

on. Emulsion stability (cc. sep'n. in 24 hours):

Distilled water 20 0 O.

300 p. p. m. hard water 0.

600 p. p. in. hard water-" 0.

1,200 p. p. in. hard water. 0.

The data of Table II show that at the 10% concentration level only the highest molecular weight detergent is capable of forming stable emulsions, particularly in hard water (Formula B-l), thus demonstrating the superiority of this detergent over lower molecular weight compounds (Formulae 13-18 and B-l9) in this respect.

EXAMPLE III A prior art type mineral oil base textile oil was compared with an oil of the present invention (Formula B-l of Example I) for solution stability, emulsion stability and scourability. The prior art oil contained 12 wt. percent of sodium sulfonate and 1.8 wt. percent of Tween 81 (Atlas Powder Co.) which is a polyoxyethylene sorbitan mono-oleate containing about 8 moles of ethylene oxide per 1 mole of sorbitan mono-oleate and about 86 wt. percent of a solvent refined Mid-Continent type distillate of 100 SSU viscosity at 100 F. and 90 Viscosity Index.

The solution and emulsion stability was measured as described in Example I. The scourability was evaluated by the Ontario Research Foundation (0. R. F.) method described in U. S. Patent No. 2,565,403 of Sproule and Dixon which is as follows:

A 20 gram sample of cloth, previously extracted with ether, is oiled with 10% of its weight of oil. The sample is placed in a 4 litre jar together with 1 litre of scouring solution. The scouring solution is composed of 0.2% soap and 0.1% soda ash. The jar is then placed in a frame capable of rotating about its central axis at 50 R. P. M. The duration of the test is 1 hour at a temperature of 110 F. After scouring, the sample of cloth is rinsed, dried and the oil content determined by ether extraction. The residual oil content is expressed as the percentage of the original oil applied.

In addition to this standard test, four other scouring tests were used to evaluate the non-ionic wool oils. These tests were modifications of the standard method using distilled and hard water with a synthetic detergent replacing the conventional anionic soap. Sodium chloride was added in one case to simulate actual plant practice in which it is used as a synergistic builder to aid the detergent in scouring the wool. The synthetic detergent was technically pure sodium lauryl sulfate. The results of these experiments are summarized in Table III below. i

Table III Designation Formula, weight percent:

odium suhonate- Tween 8l Mineral oil V. I.)..

b-H 888 can: 0

M P' s s s O M NDFU! Dec 6 1 U. S. Navy hard Water, 300 p. p. m. hardness: (Ca Cir/21120 0.2345 gum.) or litre of (Mg Ch/GH O 0.2680 gms.) distilled water.

I 0.2% soap and 0.1% soda ash in distilled water at F. for 1 hour.

I 0.25% sodium lauryl sulfate in distilled water.

10.25% sodium lauryl sulfate and 0.5% sodium chloride in distilled we er.

' N 0 separation.

b 011 and cream.

v Oil.

The data of Table 111 show that both oils produce stable emulsions in distilled water and 300 p. p. m. synthetic hard water. However, the conventional anionic wool oil shows some oil separation at 600 p. p. m. hard water and complete oil separation at 1200 p. p. m. hard water. The non-ionic wool oil of the invention forms stable emulsions up to 1200 p. p. m. hard water. In the case of the anionic-wool oil of the prior art, the calcium and magnesium ions in the hard water are reacting with the sulfonate to form insoluble soaps, thus depleting the emsulsifier. This extreme degree of hard water is at times encountered in mills where limed wool is employed.

The data also show that the prior art oil in. the O. R. F. standard scouring test using distilled water, 0.2% soap and 0.1% soda ash gives 27% residual oil whereas the non-ionic oil of the invention gives 23.5% oil. In the detergent scour using distilled water and 0.25% synthetic detergent, the prior art oil and the oil of the invention show 25% and 16.4% residual oil, respectively. When 0.5% of sodium chloride is added to the detergent scour, the non-ionic oil of the invention gives only 9.2% residual oil whereas the anionic prior art oil shows 20% oil left in the cloth.

In synthetic hard water, the non-ionic wo'ol oil is vastly superior to the anionic oil, giving 8.2% and 5.0% oil in 300 p. p. m. and 600 p. p. in. hard water, respectively, compared to 26 and 23% residual oil for the anionic oil.

It will be understood that various modifications may be made in the composition of the textile oils within the spirit of the invention. The invention also embraces the improved process for oiling various textile fibres, yarns and fabrics, particularly textiles of the type of limed wool with the textile oils of the invention and scouring such textiles with distilled water or water of any hardness References Cited in the file of this patent UNITED STATES PATENTS 1,970,578 Schoeller et a1 Aug. 21, 1934 8 Steindorf et a1. Sept. 2, 1940 MacLaurin July 16, 1946 Sproule et al Aug. 21, 1951 Jeiferson Sept. 28, 1954 OTHER REFERENCES Atlas Surface Active Agents, Atlas Powder Company, 1950 (Table No. 1), and page 24.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US1970578 *Nov 24, 1931Aug 21, 1934Ig Farbenindustrie AgAssistants for the textile and related industries
US2213477 *Nov 18, 1936Sep 3, 1940Gen Aniline & Film CorpGlycol and polyglycol ethers of isocyclic hydroxyl compounds
US2404240 *Nov 13, 1941Jul 16, 1946Ind Rayon CorpComposition for conditioning thread
US2565403 *Apr 27, 1948Aug 21, 1951Standard Oil Dev CoTextile oils
US2690426 *Mar 7, 1950Sep 28, 1954Atlas Powder CoLubricating compositions
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3198732 *Jun 12, 1962Aug 3, 1965Atlas Chem IndTire yarn finish
US3297570 *May 28, 1964Jan 10, 1967Eastman Kodak CoYarn treating compositions
US5190676 *Nov 30, 1990Mar 2, 1993Kao CorporationHigh-speed spinning oil composition containing an organophosphoric ester salt and an oxyalkylene polymer
US7153447 *Jul 22, 2002Dec 26, 2006Emini ShefqetEmulsion for use as a lubricant in the production of threads, containing mineral oil and emulsifiers selected from sorbitan esters, polyglyerol esters, polyricinoleate
U.S. Classification252/8.85
International ClassificationD06M15/53
Cooperative ClassificationC10M2207/289, C10N2240/62, D06M7/00, D06M15/53, C10M2201/02, D06M2200/40
European ClassificationD06M7/00, D06M15/53