US3928381A - Sulfurized and chlorinated alkylene polyamine reaction product lubricant additive and lubricating composition containing same - Google Patents

Sulfurized and chlorinated alkylene polyamine reaction product lubricant additive and lubricating composition containing same Download PDF

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US3928381A
US3928381A US462679A US46267974A US3928381A US 3928381 A US3928381 A US 3928381A US 462679 A US462679 A US 462679A US 46267974 A US46267974 A US 46267974A US 3928381 A US3928381 A US 3928381A
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reaction product
polyamine
sulfurized
trithione
chlorinated
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US462679A
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William P Cullen
Harry Chafetz
Walter W Hellmuth
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Texaco Inc
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Texaco Inc
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/18—Introducing halogen atoms or halogen-containing groups
    • C08F8/20—Halogenation
    • C08F8/22—Halogenation by reaction with free halogens
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/48—Isomerisation; Cyclisation
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106—Thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2221/00—Organic macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2221/04—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds

Definitions

  • R" is a divalent alkylene radical having from 2 to 6 carbon atoms and x is an integer ranging from 1 to 6.
  • R and R are derived from polyisobutylene and polypropylene.
  • the prescribed trithione is reacted with chlorine gas at a moderately elevated temperature to effect chlorination.
  • chlorine gas is contacted with or bubbled through the trithione while maintaining a temperature ranging from about 20 to 95C. While the foregoing temperature range is effective and is not considered critical, a preferred temperature range is from about 45 to 80C. With the most preferred temperature range being from about 50 to C.
  • Sufficient chlorine is employed so that the reaction produces an intermediate reaction product which contains an average of two atoms of chlorine per molecule as indicated by the formula above. While an excess of chlorine can be employed, the reaction takes place between-about 1 mole of trithione and 1 mole of chlorine.
  • the chlorinated trithione or chlorinated intermediate reaction product is then reacted with an alkylene diamine or polyalkylene polyamine to produce the lubricant additive of the invention.
  • an alkylene diamine or polyalkylene poly- 3 amine are reacted with the chlorinated trithione as indicated by the formulas above, with the preferred ratiobeing one to two moles of the amine per mole of trithione.
  • the reaction between the chlorinated intermediate product and the alkylenediamine or polyalkylene polyamine is conducted at a temperature ranging from about 100 to 275C., and preferably from about 150 to 225C. in the presence of an alkali or halide acceptor.
  • Any alkali or alkaline earth metal salt which is alkaline reacting or is effective as a halide acceptor can be employed to facilitate the above reaction.
  • the following example is of a reaction product prepared without the intermediate chlorination step.
  • the nitrogen content of the reaction product of Example IV is only about 36 percent of the nitrogen content of Example 111 of the invention. Since the nitrogen content of these additives governs their effectiveness as lubricating oil dispersants, it is evident that the same amount of the reaction product of the invention is much more effective as a dispersant or that a substantially smaller quantity of the reaction product of the invention can be used to realize an equivalent level of effectiveness. In either case a surprising improvement is obtained.
  • mineral lubricating oils having an SUS Viscosity at 100F between 50 and 1000 may be used in the formulation of the improved lubricants of this invention with the preferred base oils having a viscosity range from to 300 SUS at F.
  • a blend of base oils can be employed to provide a suitable base oil for either a single or multigrade motor oil.
  • reaction product of the invention was determined by formulating a motor oil composition and testing this in the MS-VB Engine Test.
  • the base oil employed for preparing the motor oil was a paraffinic mineral oil having an SUS Viscosity at 100F of about 450. Seven (7.0) weight percent of the reaction product of Example Ill illustrative of the present invention was incorporated in the base oil and the motor oil composition tested in the MS-VB Engine Test. The results of this test are set forth in Table I below:
  • R" is a divalent alkylene radical having from 2 to 6 carbon atoms and x is a integer ranging from 1 to 6 to produce a reaction product characterized by consisting of from 0.10 to 5.0 weight percent sulfur, 0.10 to 5.0 weight percent chlorine and 0.10 to 5.0 weight percent nitrogen.
  • reaction product according to claim 1 in which R is a radical derived from polyisobutylene and R is hydrogen.
  • An oil-soluble ashless sulfurized and chlorinated alkylene polyamine reaction product prepared by chlorinating a trithione using at least a mole of chlorine per mole of trithione at a temperature ranging from about 20 to 95C to form a chlorinated intermediate product, said trithione being represented by the formula:
  • R and R represent hydrogen or an aliphatic hydrocarbon radical having from about 50 to 125 carbon atoms, at least one of R and R representing an aliphatic hydrocarbon radical, and, reacting said intermediate product with a polyamine in the proportion of 1 to 2 moles of said polyamine per mole of said intermediate product at a temperature in the range of to 275C, said polyamine being represented by the formula H,N-(R"-NH),H

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  • Chemical & Material Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Lubricants (AREA)

Abstract

Sulfurized and chlorinated alkylene-polyamine reaction product effective as an ashless lubricant additive and a mineral lubricating oil composition containing same.

Description

United States Patent 1 Cullen et al.
[ SULFURIZED AND Cl-ILORINATED ALKYLENE POLYAMINE REACTION PRODUCT LUBRICANT ADDITIVE AND LUBRICATING COMPOSITION CONTAINING SAME [75] Inventors: William P. Cullen, Fishkill; Harry Chafctz, Poughkeepsie; Walter W. Hellmuth, Beacon, all of N.Y.
[73] Assignee: Texaco Inc., New York, N.Y.
[22] Filed: Apr. 22, 1974 [21] App]. No.: 462,679
Related US. Application Data [62] Division of Ser. No. 314.315, Dec. 12, 1972, Pat, No.
[52] US. Cl 260/327 C; 252/47; 252/47.5
[ 51 Dec. 23, 1975 Primary Examiner-John D. Randolph Attorney, Agent, or Firm-T. H. Whaley; C. G. Ries; James J, OLoughlin [57] ABSTRACT Sulfurized and chlorinated alkylene-polyamine reaction product effective as an ashless lubricant additive and a mineral lubricating oil composition containing same.
8 Claims, No Drawings SULFURIZED AND CHLORINATED ALKYLENE POLYAMINE REACTION PRODUCT LUBRICANT ADDITIVE AND LUBRICATING COMPOSITION CONTAINING SAME This is a division of Ser. No. 314,315, filed Dec. 12, 1972, now US. Pat. No. 3,843,533, granted Oct. 22, l974.
BACKGROUND OF THE INVENTION Mineral lubricating oils by themselves cannot meet the lubrication needs of modern internal combustion engines and it is customary to incorporate additives in formulated lubricating oil compositions in order to enhance the dispersant, detergent, corrosion inhibiting and antiwear properties of the composition. The difficulties of providing a satisfactory motor oil are increased because these oils are subjected to a wide range of operating conditions. In particular, it is extremely difficult to formulate a motor oil composition which will be effective under both high temperature, high speed operating conditions as well as under low temperature stop and go driving conditions. This problem is compounded when the motor oil is employed in different types of engines, such as diesel and gasoline engines both of which put very severe but greatly different stresses on the motor oil composition.
Nitrogen-containing and sulfurized nitrogen-containing ashless lubricating oil additives are well known and are effective for reducing varnish and sludge deposits in an internal combustion engine. The dispersant effectiveness of these lubricant additives is attributed primarily to the nitrogen content of the additive. However, there appears to be a limit to the amount of nitrogen which can be incorporated in the nitrogen-containing and in the sulfurized-nitrogen-containing ashless lubricant additives.
PRIOR ART US. Pat. No. 3,459,664 discloses a class of trithione polyamine reaction products which are sulfurized ashless lubricant additives.
SUMMARY OF THE INVENTION A novel ashless lubricating oil additive is provided which comprises oil-soluble sulfurized and chlorinated polyalkylene polyamine reaction product as well as a lubricating oil composition containing same.
The additive of the invention is obtained by reacting a known trithione compound, which is obtained from the reaction of a polyalkylene compound and sulfur as described in US. Pat. No. 3,459,664, withchlorine under suitable conditions to effect chlorination of the trithione compound. This product is then reacted with an alkylene polyamine, i.e. an alkylene diamine or a polyalkylene polyamine to produce the sulfurized and chlorinated polyalkylene-polyamine ashless lubricating oil additive of the invention. This reaction product is characterized by consisting of from about 0.10 to 5.0
2 weight percent sulfur, 0.10 to 5.0 weight percent chlorine and 1.0 to 5.0 weight percent nitrogen.
More'specifically, a trithione represented by the formula:
Til
where R and R have the values noted above. The intermediate product which may include some other chlorinated compounds, is then reacted with an alkylene diamine or a polyalkylene polyamine generally represented as follows: 1
and
in which R" is a divalent alkylene radical having from 2 to 6 carbon atoms and x is an integer ranging from 1 to 6. In the preferred trithione compounds, R and R are derived from polyisobutylene and polypropylene.
The prescribed trithione is reacted with chlorine gas at a moderately elevated temperature to effect chlorination. In general, chlorine gas is contacted with or bubbled through the trithione while maintaining a temperature ranging from about 20 to 95C. While the foregoing temperature range is effective and is not considered critical, a preferred temperature range is from about 45 to 80C. With the most preferred temperature range being from about 50 to C. Sufficient chlorine is employed so that the reaction produces an intermediate reaction product which contains an average of two atoms of chlorine per molecule as indicated by the formula above. While an excess of chlorine can be employed, the reaction takes place between-about 1 mole of trithione and 1 mole of chlorine.
The chlorinated trithione or chlorinated intermediate reaction product is then reacted with an alkylene diamine or polyalkylene polyamine to produce the lubricant additive of the invention. In general, one to five moles of an alkylene diamine or a polyalkylene poly- 3 amine are reacted with the chlorinated trithione as indicated by the formulas above, with the preferred ratiobeing one to two moles of the amine per mole of trithione. I
The diamine or polyamine reactants which can be employed in this reaction include alkylene diamines such as ethylenediamine, 1,2-, and 1,3-propylene diamine, 1,4-butylenediamine, 1,5-amylenediamine, 1,6- hexylenediamine and the like.
The polyalkylene polyamines which can be employed include diethylene triamine, tetraethylene pentamine, pentaethylene hexamine and hexaethylene heptamine. The diamine and polyamine reactants can be represented by the formula I-I N-(R"NH) I-I in which R is a divalent alkylene radical having from 2 to 6 carbon atoms and x has a value from 1 to 6. Additionally, ring containing nitrogenous materials, such as piperazine, aminethyl piperazine, aminoethylpiperidine etc. may also be employed.
In general, the reaction between the chlorinated intermediate product and the alkylenediamine or polyalkylene polyamine is conducted at a temperature ranging from about 100 to 275C., and preferably from about 150 to 225C. in the presence of an alkali or halide acceptor. Any alkali or alkaline earth metal salt which is alkaline reacting or is effective as a halide acceptor can be employed to facilitate the above reaction.
The product resulting from the foregoing reactions starting from a trithione which represents a mixture of compounds taken with the steps of chlorination and reaction with an alkylene diamine or polyalkylene polyamine is a very complex reaction product characterized by its method of preparation and the sulfur, chlorine and nitrogen content.
The following examples illustrate the preparation of the reaction product of the invention.
EXAMPLE I SULFURIZATION OF POLYISOBUTYLENE Polyisobutylene of about 1200 average molecular weight (496 g., 0.41 m) and sulfur (80 g., 2.5 m) were heated at 250C for 4 hours with stirring and nitrogen purge. The reaction mixture was cooled, dissolved in isooctane and chilled in an ice bath. Filtration followed by stripping under aspirator pressure afforded 504 g. product which contained 4.32%S (theory 6.9).
EXAMPLE II CHLORINATION OF SULFURIZED POLYISOBUTYLENE Sulfurized polyisobutylene from Example 1 above (288 g., .19 m) was charged to a 500 ml flask fitted with gas inlet tube, thermowell and thermocouple, stirrer and condenser. Chlorine was bubbled through the sulfurized material at 60C until net weight gained was approximately 8-10g. The mixture was purged with nitrogen for 1 hour. Elemental analysis found: %S 3.75; %CI 4.20.
EXAMPLE III REACTION OF CHLORINATED SULFURIZED POLYISOBUTYLENE WITH PENTAETI-IYLENEHEXAMINE To a 500 ml 3 necked flask fitted with gas inlet tube, thermowell and couple, stirrer and condenser was charged chlorinated sulfurized polyisobutylene from Example 11 (218 g., 0.18 m), pentaethylenehexamine (138 g., 0.6 m) and sodium carbonate (63 g., 0.6 m). The mixture was heated at 200C for 5 hours, cooled, dissolved in isooctane, filtered and extracted three times with methanol. The isooctane solution was stripped under aspirator pressure to 100C. Elemental analysis found: %N 1.1; %S 2.3; %CI 1.1.
The following example is of a reaction product prepared without the intermediate chlorination step.
EXAMPLE IV REACTION OF SULFURIZED POLYISOBUTYLENE WITH PENTAETHYLENEHEXAMINE Sulfurized polyisobutylene (120 g., 0.10m) from Example I above and pentaethylenehexamine (116 g., 0.5 m) were charged to a 500 ml 3 neck flask and heated with stirring at 250C for 6 hours. The mixture was cooled, dissolved in isooctane and triply extracted with methanol. The isooctane solution was stripped under aspirator pressure to 100C. Elemental analysis found: %N 0.4; %S 1.09.
It can be seen that the nitrogen content of the reaction product of Example IV is only about 36 percent of the nitrogen content of Example 111 of the invention. Since the nitrogen content of these additives governs their effectiveness as lubricating oil dispersants, it is evident that the same amount of the reaction product of the invention is much more effective as a dispersant or that a substantially smaller quantity of the reaction product of the invention can be used to realize an equivalent level of effectiveness. In either case a surprising improvement is obtained.
The hydrocarbon mineral base oil employed in preparing the lubricating oil composition of the invention can be a paraffinic base, naphthene base or mixed paraffin-naphthene base distillate or residual oil. Paraffin base distillate lubricating oil fractions are preferred for the formulation of the highest quality engine or motor oils. The lubricating oil base generally will have been subjected to solvent refining to improve its lubricity and viscosity temperature relationship as well as to solvent dewaxing to remove waxy components and to improve the pour of the oil. Generally, mineral lubricating oils having an SUS Viscosity at 100F between 50 and 1000 may be used in the formulation of the improved lubricants of this invention with the preferred base oils having a viscosity range from to 300 SUS at F. A blend of base oils can be employed to provide a suitable base oil for either a single or multigrade motor oil.
The effectiveness of the reaction product of the invention was determined by formulating a motor oil composition and testing this in the MS-VB Engine Test.
The MS-VB Engine Test is conducted in accordance with the detailed procedures found in ASTM Special Technical Publication No. 3l5-D; Engine Test Sequences for Evaluating Automatic Lubricants For API Service MS, published by the American Society for Testing Materials, 1916 Ruse Street, Philadelphia, Pa. The test is cyclic in nature alternating between operating and soak" periods. At test termination engine inspection according to standard procedures is conducted in the completely dissembled engine and the results of various lubricants compared accordingly.
The base oil employed for preparing the motor oil was a paraffinic mineral oil having an SUS Viscosity at 100F of about 450. Seven (7.0) weight percent of the reaction product of Example Ill illustrative of the present invention was incorporated in the base oil and the motor oil composition tested in the MS-VB Engine Test. The results of this test are set forth in Table I below:
TABLE I MS-VB ENGINE TEST PCV Value Sludge Varnish PSV Oil Ring Oil Screen at 4" Hg.
in which R and R represent hydrogen or a hydrocarbyl radical having from about 50 to 125 carbon atoms, at least one of R and R representing an aliphatic hydrocarbon radical, and, reacting said intermediate product with a polyamine in the proportion of 1 to 5 moles of said polyamine per mole of said intermediate product at a temperature in the range of 100 to 275C., said polyamine being represented by the formula:
H,N-(R"-NH),H
in which R" is a divalent alkylene radical having from 2 to 6 carbon atoms and x is a integer ranging from 1 to 6 to produce a reaction product characterized by consisting of from 0.10 to 5.0 weight percent sulfur, 0.10 to 5.0 weight percent chlorine and 0.10 to 5.0 weight percent nitrogen.
2. A reaction product according to claim 1 in which R is a radical derived from polyisobutylene and R is hydrogen.
3. A reaction product according to claim 1 in which R is a radical derived from polypropylene and R is hydrogen.
4. A reaction product according to claim 1 in which said polyamine is pentaethylenehexamine.
5. A reaction product according to claim 1 in which said polyamine is tetraethylenepentamine.
6. A reaction product according to claim 1 in which said polyamine is triethylenetetramine.
7. A reaction product according to claim 1 in which said chlorination is conducted at a temperature ranging from about 50 to 70C and said reaction with said polyamine is conducted at a temperature from 150 to 225C.
8. An oil-soluble ashless sulfurized and chlorinated alkylene polyamine reaction product prepared by chlorinating a trithione using at least a mole of chlorine per mole of trithione at a temperature ranging from about 20 to 95C to form a chlorinated intermediate product, said trithione being represented by the formula:
Til
in which R and R represent hydrogen or an aliphatic hydrocarbon radical having from about 50 to 125 carbon atoms, at least one of R and R representing an aliphatic hydrocarbon radical, and, reacting said intermediate product with a polyamine in the proportion of 1 to 2 moles of said polyamine per mole of said intermediate product at a temperature in the range of to 275C, said polyamine being represented by the formula H,N-(R"-NH),H
in which R is a divalent alkylene radical having from 2 to 3 carbon atoms and x is an integer ranging from 1 to 5, said reaction product being characterized by consisting of 0.10 to 5.0 weight percent sulfur, 0.10 to 5.0 weight percent chlorine and 0.10 to 5.0 weight percent nitrogen.

Claims (8)

1. AN OIL-SOLUBLE ASHLESS SULFURIZED AND CHLORINATED ALKYLENE POLYAMINE REACTION PRODUCT PREPARED BY CHLORINATING A REACTION PRODUCT OF SULFUR AND A POLYOLEFIN CONTAINING A TRITHIONE USING AT LEAST A MOLE OF CHLORINE PER MOLE OF TRITHIONE AT A TEMPERATURE RANGING FROM ABOUT 20* TO 95*C. TO FORM A CHLORINATED INTERMEDIATE PRODUCT, SAID TRITHIONE BEING REPRESENTED BY THE FORMULA:
2. A reaction product according to claim 1 in which R is a radical derived from polyisobutylene and R'' is hydrogen.
3. A reaction product according to claim 1 in which R is a radical derived from polypropylene and R'' is hydrogen.
4. A reaction product according to claim 1 in which said polyamine is pentaethylenehexamine.
5. A reaction product according to claim 1 in which said polyamine is tetraethylenepentamine.
6. A reaction product according to claim 1 in which said polyamine is triethylenetetramine.
7. A reaction product according to claim 1 in which said chlorination is conducted at a temperature ranging from about 50* to 70*C and said reaction with said polyamine is conducted at a temperature from 150* to 225*C.
8. An oil-soluble ashless sulfurized and chlorinated alkylene polyamine reaction product prepared by chlorinating a trithione using at least a mole of chlorine per mole of trithione at a temperature ranging from about 20* to 95*C to form a chlorinated intermediate product, said trithione being represented by the formula:
US462679A 1972-12-12 1974-04-22 Sulfurized and chlorinated alkylene polyamine reaction product lubricant additive and lubricating composition containing same Expired - Lifetime US3928381A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4317738A (en) * 1980-10-10 1982-03-02 Standard Oil Company (Indiana) Dispersants and dispersant viscosity modifiers from oxidized-sulfurized olefins

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3459664A (en) * 1966-04-08 1969-08-05 Chevron Res Trithione polyamine reaction products
US3843533A (en) * 1972-12-12 1974-10-22 Texaco Inc Lubricant composition containing sulfurized and chlorinated alkylene polyamine reaction product

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3459664A (en) * 1966-04-08 1969-08-05 Chevron Res Trithione polyamine reaction products
US3843533A (en) * 1972-12-12 1974-10-22 Texaco Inc Lubricant composition containing sulfurized and chlorinated alkylene polyamine reaction product

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4317738A (en) * 1980-10-10 1982-03-02 Standard Oil Company (Indiana) Dispersants and dispersant viscosity modifiers from oxidized-sulfurized olefins

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