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Publication numberUS3746644 A
Publication typeGrant
Publication dateJul 17, 1973
Filing dateAug 31, 1971
Priority dateAug 31, 1971
Publication numberUS 3746644 A, US 3746644A, US-A-3746644, US3746644 A, US3746644A
InventorsF Magne, R Mod, W Parker, G Sumrell
Original AssigneeUs Agriculture
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
N-substituted fatty acid amide lubricants
US 3746644 A
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Description  (OCR text may contain errors)

United States Patent 3,746,644 N-SUBSTITUTED FATTY ACID AMIDE LUBRICANTS Frank C. Magne, Robert R. Mod, and Gene Sumrell, New Orleans, La., and Winfred E. Parker, Philadelphia, Pa., assignors to the United States of America as represented by the Secretary of Agriculture No Drawing. Filed Aug. 31, 1971, Ser. No. 176,734 Int. Cl. Cm 1/38 US. Cl. 25247.5 16 Claims ABSTRACT OF THE DISCLOSURE This invention relates to N-acylmorpholines and N- mono and N,N-disubstituted fatty acid amides and to similar derivatives of epithioamides which are useful as base and extreme pressure lubricants and additives.

A non-exclusive, irrevocable, royalty-free license in the invention herein described, throughout the world for all purposes of the United States Government, with the power to grant sublicenses for such purposes, is hereby granted to the Government of the United States of America.

This invention relates to certain compounds which are N-fatty acyl derivatives of primary and secondary amine and N-substituted acyl derivatives of primary and secondary amines which have exhibited utility as base lubricants, extreme pressure lubricants or lube additives. More particularly, this invention relates to N- and N,N-disubstituted long chain aliphatic amides the acyl component of which is a normal, branched, or substituted alkenoic or alkanoic acyl group containing from 16 to 22 carbon atoms the amide nitrogen of which may be derived from an alkyl amine, dialkyl amine, alkylalkoxyalkylamine, dialkoxyalkylamine or nitrogen heteroalicyclic. Typical amines are butylamines, dibutylamines, N-methyl-alkoxyethyl amine, di-ethoxyethyl amine, and morpholine. The acyl substituted referred to may be divalent sulfur or pentavalent phosphorous.

We have discovered that many of the simple N-alkyl and N,N-dialkyl or N-alkyl-N-alkoxyalkyl amides of the C to C alkenoic or alkanoic fatty acids are good base lubricants. We have further discovered that the introduction of divalent sulfur into the fatty acid moiety imparts excellent extreme pressure lubricant characteristics to such compounds. In particular we have found the epithio group ethyloleamide. Compounds showing particular promise as extreme pressure lubricants or additives are N,N-dibutyl 9,10 epithiostearamide, N,N-dibutyl-9,10,12,13- diepithiostearamide, 9,10-epithiostearoyl morpholine, N- ethoxyethoxyethoxypropyl 9,10 epithiostearamide, n-9, 10,12,13-diepithiostearoylmorpholine and N-[9(l0)-hydroxy-9 10) -dibutylphosphato] stearamide.

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Compounds showing particular promise as antiwear additives are N,N-dibutyl- [9 10) -hydroxy- 9) IO-dibutylphosphato1stearamide and N,N-[9(10)mercapto-(9) 10- dibutylphosphatostearoyl]morpholine.

EXAMPLE 1 N-methyl-N-butyloleamide.- grams (0.33 mole) of oleoyl chloride was added dropwise and with stirring to a mixture of 29 grams (0.33 mole) of N-methyl-N- butylamine and 27 grams (0.33 mole) of pyridine. Stirring was continued until the heat of reaction subsided. The solid pyridine hydrochloride was filtered off and the filtrate was washed successively with aqueous HCl and water until acid free. It was dried, stripped, percolated through an activated alumina column, and the product removed from the percolate by stripping oif the solvent. Analysis of die product: Percent C, 78.87 (theory 78.63); percent H, 13.02 (theory 12.82); percent N, 3.96 (theory 3.99).

EXAMPLE 2 N,N-dibutyloleamide.-This material was prepared by the procedure of Example 1 from 100 grams (0.33 mole) of oleoyl chloride, 42.5 grams (0.33 mole) of di-n-butylamine and 27 grams (0.33 mole) pyridine. Analysis of the product: Percent C, 78.94 (theory 79.25); percent H, 13.16 (theory 13.06); percent N, 3.44 (theory 3.56) confirm the preparation.

EXAMPLE 3 Ethoxyethoxyethoxy propyloleamide.-This material was prepared by the procedure of Example 1 from 100 grams (0.33 mole) of oleoyl chloride, 73.0 grams (0.33 mole) ethoxyethoxyethoxy-propylamine and 27.0 grams (0.33 mole) pyridine. Analysis of percent C, 71.84 (theory 72.04); H, 11.80 (theory 11.80), and N, 2.96 (theory 2.90) confirm the preparation.

EXAMPLE 4 Ethoxyethoxypropyloleamide.--This material was prepared by the procedure of Example 1 from 100 grams (0.33 mole) of oleoyl chloride, 58.3 grams (0.33 mole) ethoxyethoxypropylamine and 27.0 grams (0.33 mole) of pyridine. Analyses of percent C, 71.45 (theory 73.80); percent 'H, 11.87 (theory 12.07); and percent N, 2.92 (theory 3.18) confirm the preparation.

EXAMPLE 5 Methoxyisopropyloleamide.-This material was prepared b the procedure of Example 1 from 100 grams (0.33 mole) of oleoyl chloride, 29.3 grams (0.33 mole) methoxyisopropylamine and 27.0 grams (0.33 mole) pyridine. Analysis of percent C, 73.15 (theory 74.99); percent H, 12.01 (theory 11.93); and percent N, 3.67 (theory 3.97) confirm the preparation.

EXAMPLE 6 Methoxyethyloleamide.-This material was prepared by the procedure of Example 1 from 10 grams (0.33 mole) of oleoyl chloride, 24.4 grams (0.33 mole) of methoxyethylamine and 27.0 grams (0.33 mole) pyridine. Analysis of percent C, 73.08 (theory 74.55); percent H, 11.98 (theory 11.83); and percent N, 3.31 (theory 4.14) confirm the preparation.

EXAMPLE 7 Oleoylmorpholine.-This material was prepared by the procedure of Example 1 from 100 grams (0.33 mole) of oleoyl chloride, 28.7 grams (0.33 mole) of morpholine and 27.0 grams (0.33 mole) of pyridine.

3 EXAMPLE 8 N,N-dibutyloleamide.'lhis product was prepared following the exact procedure of Example 2 except for the substitution of oleoyl chloride by linoleoyl chloride.

EXAMPLE 9 N,N-dirbutyl-9,10-epithiostearamide.120 grams (0.30 mole) of N,N-dibutyloleamide was epoxidized by the addition with stirring of 62.0 grams (0.36 mole) of metachloroperbenzoic acid in 630 ml. of chloroform. Reaction was continued for 1 hour beyond final addition and the excess peracid destroyed by a small amount of a solution of Na SO The metachlorobenzoic acid was removed by a NaHCO Wash, followed by water washing. The CHCl solution was then dried with anhydrous Na SO and the CHCl stripped off to recover the product N,N-dibutyl-9,10-epoxystearamide, oxirane content 3.45% (theory 3.91%). 100 grams (0.24 mole) of this product was added to a well stirred slurry of 55.7 g. (0.73 mole) of thiourea and 89.5 g. (0.73 mole) of benzoic acid in acetone. Stirring was continued for 3 hours beyond the terminal addition whereupon the benzoic acid was washed out with 38.8 g. (0.36 mole) of Na CO and the organic product extracted with hexane. The organic phase extract was dried and stripped to recover the product N,N-dibutyl-9,lO-epithiostearamide containing 6.41% sulfur (theory 6.67%

EXAMPLE 10 N (9,10 epithiostearoyl)morpholine.This product was prepared by the exact procedure described in Example 9 except for the substitution of oleoylmorpholine for the N,N-dibutyloleamide of Example 9. Analysis of product showed percent C, 71.22 (theory 69.34); percent H, 11.22 (theory 10.77); percent N, 3.66 (theory 3.68); percent S, 3.44 (theory 7.80).

EXAMPLE 11 N,N dibutyl 9,10-12,13 diepithiostearamide.This product was prepared following the procedure described in Example 9 except for the replacement of the N,N-dibutyloleamide of Example 9 by N,N-dibutyllinoleamide, and a doubling of the molar ratios of all reagents. The product analyzed as follows: percent C, 69.64 (theory 68.57); percent H, 10.93 (theory 10.76); percent N, 3.10 (theory 3.07); percent S, 11.7 (theory 14.06).

EXAMPLE 12 N ethoxyethoxyethoxypropyl 9,10 epithiostearamide.To 166 g. of N-ethoxyethoxyethoxypropyl oleamide, Example 3, was added dropwise and with stirring 73.8 g. of m-chloroperbenzoic acid in 800 ml. of CHCI The spent m-chloroperbenzoic acid was removed with 10% aqueous NaHCO and the epoxide recovered by drying and stripping 01f the CHCl 171 g. of this epoxide was added dropwise to a slurry of 56 g. thiourea in 1000 ml. of acetone and the concurrent addition of 43.4 g. of glacial acetic acid and the reaction mixture stirred for 3 hours. The glacial acetic acid was neutralized with Na CO and the episulfide, N-ethoxyethoxyethoxypropyl-9,10-epithiostearamide, extracted with Skellysolve B and washed, dried, and stripped. Its elemental analysis was C=67.1 (66.52), H=11.42 (10.88), N=2.67 (2.87), S=2.29 (6.57).

EXAMPLE 13 N-ethoxyethoxyethoxypropyl 9 10 mercaptostearamide.--173 g. of N-ethoxyethoxyethoxy propyloleamide in CCl, was treated in the cold with a CCl solution containing 60.9 g. of bromine. Any unreacted bromine was removed by a thiosulfate wash. 140 g. of the resulting dibromo compound was added dropwise to a well stirred solution of 72 g. of Na S'9H O in dimethylsulfoxide maintained at 80 C. Stirring was continued at 80 C. for 3 hours. Water was added and the reaction product was extracted with hexane; washed, dried, and stripped. Ele- EXAMPLE 14 N,N dibutyl 9(10) [dibutylphosphono]stearamide.- g. of N,N-dibutyloleamide, Example 2, 148 g. of dibutyl phosphite, and 1.29 of benzoyl peroxide catalyst were heated at C. for 3 /2 hours. Additional units of 1.29 g. of benzoyl peroxide was added after the first and second hours of reaction time. The excess dibutyl phosphite was then removed by distillation at reduced pressure, 0.45 mm. Hg. The stillpot contents showed strong adsorption bonds at 8, 9.3, and 9.7 microns characteristic of the phosphonate group. The elemental analysis was C=obs. 71.46 (69.50), H=obs. 12.42 (11.92), N=obs. 2.20 (2.38), P=obs. 4.24 (5.28) percent respectively.

EXAMPLE 15 N9,10-12,13-diepithiostearoylmorpholine.-This product was prepared by the same procedure described in Example 9 except for the substitution of linoleoyl morpholine for the N,N-dibutyloleamide of Example 8 and the doubling of molar proportions of the m-chloroperbenzoic acid in the epoxidation step and the thiourea and benzoic acid in the epithioation step. The elemental analysis was C=obs. 68.89 (63.92), H=obs. 10.26 (9.44), N=obs. 3.29 (3.38), S=obs. 4.00 (15.49) percent respectively.

EXAMPLE 16 N,N dibutyl [9(10) hydroxy (9) 10 dibutylphosphato]stearamide.-44.7 g. of dibutylhydrogen phosphate was added to 182.2 g. of N,N-dibutyl-9,10-epoxystearamide at 90-95 C. with stirring. Reaction conditions were continued for 3 /2 hours after termination of the addition. The reaction product was dissolved in commercial hexane and the unreacted dibutyl hydrogen phosphate neutralized and washed out with portions of aqueous 10% NaHCO followed by several water washes. Acidulation of the hexane phase with diluted I-ICl followed by several water washes, drying and stripping, yielded the product. Elemental analysis was, C=obs. 66.56 (65.91), H=obs. 11.04 (11.30), N=obs. 2.90 (2.26), P=obs. 3.04 (4.20).

EXAMPLE 17 N-[9(10)mercapto (9)10 dibutylphosphatostearoyl] morpholine.-12 g. of dibutylhydrogen phosphate was added dropwise with stirring to 51.0 g. of (9,10-epithiostearoyl)morpholine, the preparation of Example 10, at 85-90 C. and the heating and stirring continued for 3 hours beyond the terminal addition. The reaction product was dissolved in commercial hexane and any excess or unreacted was neutralized and washed out with aqueous 10% NaHCO The hexane extract was washed several times with water, dried and stripped. The elemental analysis of the product was C=obs. 66.74 (69.36), H=obs. 10.69 (11.05), N=obs. 2.89 (3.32), S=obs. 3.27 (2.17), P=obs. 1.68 (2.10) percent respectively.

EXAMPLE 18 The compounds prepared in accordance to the procedures given in Examples 1 through 7 were evaluated as base lubricants in the Shell Four-Ball Wear tests following a modified procedure of ASTM D2266-67. The resulting scar diameter on the balls after running at 600 r.p.m. for 1 hour at C. and 50 kg. load were compared with the scars obtained using commercial lubricants such as Aeroshell Mil-L-708 (di-2-ethylhexyl sebacate and additive), Gulfpride, single G, MS, multiviscosity, and 100 sec. parafiin oil. The results of these tests are re ported in Table I.

TABLE I.ANTIWEAR LUBRICANT PROPERTIES OF FATTY ACID AMIDES Avg. wear seer, mm.

With- With out addiaddi- Compound tive tive Additive 1...... N,N-bis(2-eth0xyethyl)- 0. 597 0. 735 N,N-di-butyloleamide. 9,10-epithiostearamide.

2-..... N,N-dl-n-butyl-9,10epithio- 0. 842 None.

stearemide.

3-. Oleoylmorpholine 0.623 0.658 Do.

4 N ,N-dimethyloleamide 0. 797 0. 987 D0.

5 N,N-di-n-propyloleamide 0. 908 0. 885 D0.

6 N,N-di-n-hexyloleamide 0. 893 0. 898 D0.

7. N,N-di-n-butylerueamide-.... 0.758 0. 798 Do.

8. N,N-dl-n-butyl amide of sel. 0. 798 0. 958 Do.

hydrogenated cottonseed fatty acids.

9 N,N-bis(2-methoxyethyl)- 0. 626 0. 725 Do.

oleamide.

10 N,N-dibutyloleamide 0. 710

11 N-oleoyl-4-propylpiperidine. 0. 847

12 Morpholide oi sel. hydrogen- 0. 642

ated cottonseed fatty acids.

13.. N-methyl-N-butyloleamide 0. 607

14 N-ethoxyethoxyethoxypro- 0. 503

pyoleamide.

15 N-ethoxyethoxypropyl- 0. 526

oleamide.

16 N-methoxyisopropyloleamide 0. 705

17 N-methoxyethyloleamide 0. 420

18- 102 sec paraifin oil 0.902 N-methoxyethyloleamide.

19.--. D.O. 0.906 Do.

20 N,N-dibutyl-Q (10) -carbo- 0. 610

butoxy octadecanamide.

21.... 102 sec parafiin oil 0. 818 N,N-dibutyl- 9(10)-carbobutoxyoctadecanemide.

22--.- .O.S 0.945 Do.

23 N-[9 (10)mercapto-(9)10- 0. 615

dibutyl-phosphatostearoyl] morpholine.

24-... 102 sec paraffin oil 0. 552 N-[9(l0)rnercapto-(Q)10- dibutylphosphatostearoyl] morpholine.

25---. D.0.S 0.535 Do.

26 N ,N-dibutY -l (1 Ydr0xy' 0. 498

(9)10-dibutylphosphato] stearamide. 27-... 102 sec paraflin oil 0. 498 N,N-dlbutyl- [9(10)-hydroxy (9)104iibutylphosphate]- stearamide.

28---; D.O.S 0.498

. ,N-dibutyl-9 (10) -[dibutyl- 0. 530

phosphono1stearamide. 30 N-ethoxyethoxyethoxyphopyl-9,loepithiostearamlde. 31 N-ethoxyethoxyethoxypropyl-9(10)mercaptostearamide. 32 N- (9,l0-12,13-diepithiostearoyl)morpholine.

3 Bis (2-ethylhexyl) sebacate.

34-.-- 100 sec paraflin oil 0 803 35-..- Aero Shell (Mil-7808) 0 5 36.... Gulf Pride, single G, MS,

multiviscosity.

37. 100 see paraffin oil 0. 813 N,N-dibutyl- 14.10-12.13- diepithiosteammide.

38. Bis(2-ethylhexyl) sebacate 0.836 0. v

39---. 100 see paraifin oil 0. 723 N-9,10-epithiostearoyl mor-' pholine. 40 Bis(2-ethylhexyl) sebacate 0. 915 Do. 41.... 100 sec paraffin oil 0.917 N,N-dibutyl-9,

- 10dichlor0-. stearamide. 42 Bis (2-ethylhexyl)sebacate 0. 848 Do.

' mercapto- (9) 10-dibutylphosphatostearoyl] morpholine not only exhibit low wear characteristics in themselves but also impart as additives such characteristics to parafiin oil and DOS base lubricants.

6 EXAMPLE 19 The various amides were evaluated as extreme pressure lubricants or additives in a Shell 4-ball extreme pressure tester at 1440 ppm. following ASTM Procedure D 2596- 67T. Loads were increased in increments of 20 kg. to weld point and the test ran for one minute or to weld whichever occured first. Commercial hypoid fluid SAE was employed as the control E.P. lubricant. The performance of the amides tested is given in Tables II, III, and IV.

TABLE II.-EXTREME PRESSURE TESTS (ASTM D3596-67T) Weld point No With addi- 5% Compound tive #2 1 N,N-bis(2-ethoxyethyl) oleamide 170 2- N,N-di-n-butyl-9,10epithlostearamide 300 3 Oleoylmorpholine 120 150 4. N,N-dimethyloleamide. 120 5 N,N-dl-n-propyloleamide 120 6 N,Ndi-n-hexyloleamide 120 180 7 N,N-di-n-butylerueamide 120 200 8 N,N-di-n-butyl amide of hydrogenated cotton- 120 seed fatty acids. 9 N,N-bis(2-methoxyethyl)oleamide...-- 10 N-methyl-N-butyloleemi de 11 N,N-dibutyl-9,lO-epithiostearamide 12 N,N-dibuty1-9,1012,13-diepithiostearamide.... 13 N-ethoxyethoxyethoxypropyloleamide 14 N-ethoxyethoxypropyloleamide 15 N-methoxyisopropyioleamide l6 N-methoxyethyloleamide 17 N-9,IO-epithiostearoylmorpholine.. 18 Bis(2-ethylhexyl) sebacate 19 100 see paraffin oil 20-. SAE #90 commercial hypoid fluid TABLE III.-EVALUATION OF N ,N-DIBUTYL-9,1012,13-DI EPITHIOSTEARAMIDE AS AN ADDITIVE AND AS A BASE OIL IN EXTREME PRESSURE TESTS. (ASTM D2596-67T) Wear Percent Load, sear,

Base 011 additive kg. mm.

100 sec paraflin oil 5 140 1. 90 Do. 5 200 2. 35 5 220 2. 75

5 240 Weld 5 200 9 Weld 10 270 Weld None 120 1. 38

None 160 1. 61

None 200 1. 89

None 280 2. 13

None 320 2. 47

None 360 2. 70

None 400 2. 88

Do None 440 4 Weld Extreme pressure tests on N-ethoxyethoxyethoxypropyl-9,10-eplthiostearamide (PC0N0. 7682) TABLE III-Continued Avg. Percent Applied scar, Base oil additive load mm.

Extreme pressure tests on N-ethoxyethoxyethoxypropyl-O(10)-mer captostearamide (P OONo. 7683) 7683 None 200 1. 54

7683.- None 360 2.26

7683 None 400 2. 25

7683 None 450 2. 15

83 None 500 2. 15

- 7683 (5%) 160 Weld D.O.S 7683 (5%) 180 Weld Extreme pressure tests on N-(9,1012, 13-diepithiostearoyl)morplioline (P O-O-No. 7684) None 200 2. 21

None 260 2.38

None 340 2. 43

None 400 2.75

None 460 2.90

None 500 7 2. 98

7684 (5%) 140 Weld (5%) 150 Weld (5%) 170 Weld Extreme pressure tests on N,N-dibutyl-9(l0)-(dibutylphosphono)stearamide (PC-O-No. 7685) None 120 3. 05 None 140 4. 50 None 150 Weld Extreme pressure tests on N,N-dlbutyl-[(10)-hydroxy-9(l0)-dibutylphosphatolstearamide (P C-O-No. 7 686) None 200 0.887

None 300 2.78

None 340 4. 32

None 350 4. 50

None 360 Weld 7686 (5%) 150 3.01 7686 (5%) 160 Weld 7686 (5%) 120 1. 95 (5%) 140 2.85

86 (5%) 160 Weld Extreme pressure tests on N-[9(10)-mercapto-9(l0)-dibutylphosphatostearoyl1morpholine (0 0-0-No. 7687) None 120 0. 608 None 160 1. 45 None 200 1. 40 None 240 1. 70 None 280 3. 36

Extreme pressure tests on N N-dibutyl-SJ()carbobutoxyoctadec anamide (P ONo. 7688) None 80 1. 92 None 90 2. 18 None 100 2. 45 None 120 Weld 5 seconds. 2 4 seconds. a 10 seconds. 4 46 seconds. 5 Incipient seizure.

6 Test stopped because of extreme decomposition and noxious fumes. Did not weld.

7 Test stopped because of extreme decomposition. Did not weld.

TABLE 1V.EVALUATION OF N-9, IO-EPITHIOSTEAROYL MORPHOLINE AS AN ADDITIVE AND AS A BASE OIL IN EXTREME PRESSURE TESTS (ASTM D2596-67T) We claim:

1. A composition of matter useful as a base and extreme pressure lubricant consisting of a base lubricant selected from the group consisting of N-methoxyethyloleamide, N, N-bis-( 2-ethoxyethyl oleamide, N,N-bis (Z-mcthoxyethyl) oleamide, oleoylmorpholine, N,N-dimethyloleamide, N,N- dipropyloleamide, N,N dibutylolcamide, N,N-dib utylerucamide, and N,N-dibutylamide of hydrogenated cottonseed fatty acids, and an extreme pressure lubricant selected from the group consisting of N-(9,10-12,13-diepithiostearoyl)morpholinc and N,N dibuty1-9,l0'epithi0stearamide.

2. The composition of claim 1 wherein the base lubricant is N-methoxyethyloleamide and the extreme pressure lubricant is N-(9,l0-l2,l3 diepithiostearoyDmorpholinc.

3. The composition of claim 1 wherein the base lubricant is N,N-bis(2 ethoxycthyl)oleamide and the extreme pressure lubricant is N,N-dibutyl-9,10-epithiostearamide.

4. The composition of claim 1 wherein the base lubricant is N,N-bis(2-methoxyethyl)oleamide and the extreme pressure lubricant is N,N-dibutyl-9,IO-epithiostearamide.

5. The composition of claim 1 wherein the base Inbricant is oleoylmorpholine and the extreme pressure lubricant is N,N-dibutyl9,lO-epithiostearamide.

6. The composition of claim 1 wherein the base lubricant is N,N-dimethyloleamide and the extreme pressure lubricant is N,N-dibutyl-9,IO-epithiostearamide.

7. The composition of claim 1 wherein the base Inbricant is N,N-dipropyloleamide and the extreme pressure lubricant is N,N-dibutyl-9,IO-epithiostearamide.

8. The composition of claim 1 wherein the base lubricant is N,N-dibutyloleamide and the extreme pressure lubricant is N,N-dibutyl-9,IO-epithiostearamide.

9. The composition of claim 1 wherein the base lubricant is N,N-dibutylerucamide and the extreme pressure lubricant is N,N-dibutyl-9,lo epithiostearamide.

10. The composition of claim 1 wherein the base Inbricant is N,N-dibutylamidc of the hydrogenated cottonseed fatty acids and the extreme pressure lubricant is N, N-dibutyl-9,10-epithiostearamide.

11. An extreme pressure lubricant composition wherein the extreme pressure lubricant is N,N-dibutyl-9,10-epithiostearamide.

12. An extreme pressure lubricant composition wherein the extreme pressure lubricant is N,N-dibutyl-9,l0-12,13- diepithiostearamide.

13. An extreme pressure lubricant composition wherein the extreme pressure lubricant is N(ethoxyethoxyethoxy) propyl-9,IO-epithiostearamide.

14. An extreme pressure lubricant composition wherein the extreme pressure lubricant is N-(9,10-epithiostearoyl) morpholine.

15. An extreme pressure lubricant composition wherein the extreme pressure lubricant is N-(9,10-l2,13-diepithiostearoyl)morpholine.

16. An extreme pressure lubricant composition wherein the extreme pressure lubricant is N- (ethoxyethoxyethoxy) propyl-9 10) -mercaptostcaramide.

References Cited UNITED STATES PATENTS 3,119,877 1/1964 Campbell et al. 252-475 3,166,504 1/1965 Krukzicner et a1. 252-475 3,312,620 4/1967 Low et a1. 252-475 3,312,619 4/1967 Vineyard 252-475 3,413,224 11/1968 Knapp 252-475 WERTEN F. W. BELLAMY, Primary Examiner US. Cl. X.R.

Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3846449 *Apr 6, 1973Nov 5, 1974Us AgricultureN-substituted fatty acid amide lubricants
US3873457 *Feb 21, 1973Mar 25, 1975Us AgricultureN-substituted fatty acid amide lubricants
US3894958 *Nov 5, 1973Jul 15, 1975Texaco IncMixed secondary alkyl amide synthetic lubricant compositions
US4199460 *Sep 26, 1978Apr 22, 1980The United States Of America As Represented By The Secretary Of AgricultureAddition products of dialkylphosphorodithioic acid, hexachlorocyclopentadiene or bromotrichloromethane to unsaturated or epoxy fatty acid amides and esters
US4208293 *Nov 13, 1978Jun 17, 1980Ethyl CorporationFatty acid amide of diethanolamine
US4439336 *Jul 1, 1981Mar 27, 1984Ethyl CorporationLubricant composition containing mixed fatty acid ester and amide of diethanolamine
US5766612 *Oct 12, 1994Jun 16, 1998Basf AktiengesellschaftUse of endgroup-capped fatty amide alkoxylates
DE2945851A1 *Nov 13, 1979May 14, 1980Ethyl CorpSchmieroel-zubereitung