Succinimide derivatives and processes for their preparation

• US 5,286,873 A
• Filed: 05/12/1992
• Issued: 02/15/1994
• Est. Priority Date: 09/21/1989
• Status: Expired due to Fees

• Current Assignee: BP Chemical Company (BP PLC)
• Original Assignee: BP Chemical Company (BP PLC)
• Inventors: Cook, Stephen J.
• Primary Examiner(s): Springer, David B.
• Application Number:
  US07/881,692
• Time in Patent Office: 644 Days
• Field of Search: 548/522
• US Class Current: 548/522
• CPC Class Codes: C07D 207/412 Acyclic radicals containing more than six carbon atoms
• CPC Class Codes: C08F 10/00 Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
• CPC Class Codes: C08F 8/30 Introducing nitrogen atoms or nitrogen-containing groups
• CPC Class Codes: C10M 133/52 having a carbon chain of 30 or more atoms
• CPC Class Codes: C10M 133/56 Amides; Imides
• CPC Class Codes: C10M 2215/042 containing hydroxy groups; Alkoxylated derivatives thereof
• CPC Class Codes: C10N 2040/25 Internal-combustion engines
• CPC Class Codes: C10N 2040/251 Alcohol fueled engines
• CPC Class Codes: C10N 2040/255 Gasoline engines
• CPC Class Codes: C10N 2040/28 Rotary engines

Abstract

A process for producing a lubricating oil dispersant additive comprises:

step (1) reacting compound (A), wherein compound (A) is a hydrocarbyl-substituted or a substituted hydrocarbyl-substituted succinic acid or anhydride or ester thereof, with compound (B) of formula (I)

H.sub.2 N(CHR.sup.1 CHR.sup.2 O).sub.n CHR.sup.3 CHR.sup.4 NH.sub.2(I)

wherein one of R¹ and R² is hydrogen and the other is hydrogen or a lower alkyl group and n is an integer from 1 to 10 and one of R³ and R⁴ is hydrogen and the other is hydrogen or a lower alkyl group, each of the --(CHR¹ CHR² O)-- units being independently defined, to give a product (C) and

step (2) reacting product (C) with a diisocyanate (D) of formula (II)

OCN--R.sup.5 --NCO                                         (II)

wherein R⁵ is a divalent organic group. Novel succinimides have been prepared by the disclosed process, lubricating oil compositions comprise 1-20% w/w of the modified succinimides. The succinimides have dispersancy and VI improver properties.

Claims

1. A product suitable as an oil dispersant additive which product is prepared by a process which comprises:

step (1) reacting compound (A), wherein compound (A) is a hydrocarbyl-substituted or a substituted hydrocarbyl-substituted succinic acid or anhydride or ester thereof, with compound B of formula (I)

space="preserve" listing-type="equation">H.sub.2 N(CHR.sup.1 CHR.sup.2 O).sub.n CHR.sup.3 CHR.sup.4 NH.sub.2(I)

wherein one of R¹ and R² is hydrogen and the other is hydrogen or a lower alkyl group, n is an integer from 1 to 10, and one of R³ and R⁴ is hydrogen and the other is hydrogen or a lower alkyl group, each of the --(CHR¹ CHR² O)-- units being independently defined, to give a product (C) and

step (2) reacting product (C) with a diisocyanate (D) of formula (II)

space="preserve" listing-type="equation">OCN--R.sup.5 --NCO (II)

wherein R⁵ is a divalent hydrocarbyl group.

2. A product as defined in claim 1 wherein said compound (A) is a compound of formula (III):

##STR3## where R⁶ is an alkyl or alkenyl group or substituted alkyl or alkenyl group having a number average molecular weight in the range from about 500 to about 3,000.

3. A product as defined in either claim 1 or claim 2 wherein said compound (B) is a compound of formula (I) wherein n is an integer from 2 to 7, R¹ and R³ are each hydrogen, and R² and R⁴ are each methyl.

4. A product as defined in claim 1 wherein the molar ratio of succinic groups added to compound (B) added is in the range 5:

1 to 0.5;

1.

5. A product as defined in claim 4 wherein the molar ratio of succinic groups added to compound (B) added is in the range 1.5:

1 to 1.1;

1.

6. A product as defined in either claim 1 or claim 2 wherein the molar ratio of compound (B) to compound (D) is in the range 20:

1 to 0.5;

1.

7. A product as defined in claim 1 wherein the ratio of moles of primary amino groups in product (C) to moles of compound (B) reacted is greater than 0.5:

1.

8. A product as defined in claim 1 wherein R⁵ in formula II is selected from the group consisting of alkylene, aralkylene, cycloalkylene, arylene, alkenylene, and alkynylene.

9. A product as defined in claim 8 wherein R⁵ is a C₄ -C₁₂ alkylene group.

10. A product as defined in claim 8 wherein R⁵ is a tolyl group.

11. A product as defined in claim 8 wherein R⁵ is a methylene diphenylene group.