Substituted Succinimides

• US 5,554,768 A
• Filed: 05/25/1994
• Issued: 09/10/1996
• Est. Priority Date: 05/27/1993
• Status: Expired due to Fees

• Current Assignee: Hoechst Aktiengesellschaft (Sanofi )
• Original Assignee: Hoechst Aktiengesellschaft (Sanofi )
• Inventors: Ehrler, Rudolf, D onges, Reinhard, Helwerth, Rainer
• Primary Examiner(s): Springer, David B.
• Application Number:
  US08/248,764
• Time in Patent Office: 839 Days
• Field of Search: 548/545, 548/531, 548/536, 548/544, 548/550
• US Class Current: 548/545
• CPC Class Codes: C07D 207/404 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
• CPC Class Codes: C07D 207/408 Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms
• CPC Class Codes: C07D 207/412 Acyclic radicals containing more than six carbon atoms
• CPC Class Codes: C07D 207/416 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
• CPC Class Codes: C11D 3/28 Heterocyclic compounds containing nitrogen in the ring

Abstract

The present invention relates to succinimides of the formula I ##STR1## in which R¹ and R², independently of one another, are hydrogen, C₁ -C₂₄ -alkyl, C₂ -C₂₄ -alkenyl, C₆ -C₁₂ -cycloalkyl, C₆ -C₁₂ -cycloalkenyl, C₆ -C₁₂ -aryl, C₁ -C₂₄ -alkoxy, C₁ -C₂₄ -acyl, C₁ -C₂₄ -acyloxy, a hydroxyl, amino or sulfo group or a C₁ -C₂₄ -dialkylamino, C₁ -C₂₄ -acylamino, C₁ -C₂₄ -alkylsulfato, C₁ -C₂₄ -alkylsulfonato, C₁ -C₂₄ -alkylsulfito, C₁ -C₂₄ -alkylsulfinyl or C₁ -C₂₄ -alkoxycarbonyl radical, and

R³ is a polyhydroxyalkyl radical of the formula ##STR2## in which R⁴ is --(CHOR⁷)_n --H,

R⁵ is --(CHOR⁷)_m --H,

R⁶ is --(CHOR⁷)_o --H where n+m+o is 2-6, and

R⁷ is H or a carbohydrate attached in the form of a glycoside from the series comprising reducing sugars, a process for their preparation and their use.

Claims

1. A succinimide of the formula I ##STR7## in which R¹ and R², independently of one another, are hydrogen, C₁ -C₂₄ -alkyl, C₂ -C₂₄ -alkenyl, C₆ -C₁₂ -cycloalkyl, C₆ -C₁₂ -cycloalkenyl, C₆ -C₁₂ -aryl, C₁ -C₂₄ -alkoxy, C₁ -C₂₄ -acyl, C₁ -C₂₄ -acyloxy, a hydroxyl, amino or sulfo group or a C₁ -C₂₄ -dialkylamino, C₁ -C₂₄ -acylamino, C₁ -C₂₄ -alkylsulfato, C₁ -C₂₄ -alkylsulfonato, C₁ -C₂₄ -alkylsulfito, C₁ -C₂₄ -alkylsulfinyl or C₁ -C₂₄ -alkoxycarbonyl radical, and

R³ is a polyhydroxyalkyl radical of the formula ##STR8## in which R⁴ is --(CHOR⁷)_n --H,

R⁵ is --(CHOR⁷)_m --H,

R⁶ is --(CHOR⁷)_o --H where n+m+o is 2-6, and

R⁷ is H.

2. A process for preparing a succinimide of the formula I, comprising the steps of

introducing the amino polyol of the formula III ##STR9## in which R³, R⁴ and R⁵ have the meaning given in claim 1, into a suspending agent or solvent,

adding the carboxylic acid IIa and/or the carboxylic anhydride IIb, ##STR10## in which R¹ and R² have the meaning given in claim 1, if appropriate with slight heating, and

heating this mixture at a temperature and over a sufficiently long period to make the mixture substantially free of suspending agent or of solvent and the water of reaction formed and to bring the base nitrogen content of the reaction mixture down to less than 0.1% by weight.

3. The process as claimed in claim 2, wherein the suspending agents or solvents used are water, alcohol, or a water/alcohol mixture.

4. The process as claimed in claim 2, wherein the addition takes place at a temperature of between 20°

and 80°

C.

5. The process as claimed in claim 2, wherein, in order to remove the suspending agent or solvent present, the mixture is heated to a maximum temperature of 160°

C. and then, optionally, to a maximum temperature of 190°

C.

6. The process as claimed in claim 2, wherein the mixture is heated over a period of up to 3 hours.

7. An aqueous solution, containing a succinimide of the formula I as claimed in claim 1.

8. An aqueous solution as claimed in claim 7, which contains 10-60% by weight of a nitrogen base, and has a pH of greater than 7.

9. The process as claimed in claim 3, wherein the alcohol is a lower aliphatic alcohol.

10. The process as claimed in claim 4, wherein the temperature is between 50°

to 70°

C.

11. An aqueous solution as claimed in claim 8, wherein said nitrogen base is a tertiary amine.