FUEL ADDITIVE COMPOUNDS AND METHOD OF MAKING THE COMPOUNDS

1 . A process for forming a detergent base product, the process comprising:

forming a bis-Mannich intermediate compound by reacting (i) at least one hydroxyl substituted aromatic ring compound having on the ring an aliphatic hydrocarbyl substituent derived from a polyolefin having a number average molecular weight of about 500 to about 3000; (ii) at least one primary amine; and (iii) at least one aldehyde; and

reacting the bis-Mannich intermediate compound with at least one second amine compound chosen from primary and secondary amines to form the detergent base product.

2 . The process of claim 1 , wherein at least one hydroxyl substituted aromatic ring compound has a formula 1,

where R 1 , R 2 and R 3 are substituents independently chosen from a hydrogen radical, C 1-6 alkyls and hydrocarbyl substituents having a number average molecular weight in the range of about 500 to about 3000, with the proviso that at least one of R 1 , R 2 and R 3 is a hydrocarbyl substitutent.

3 . The process of claim 2 , wherein one of R 1 , R 2 and R 3 is a C 1-6 alkyl chosen from methyl, ethyl, propyl, isopropyl, butyl, and isobutyl.

4 . The process of claim 2 , wherein the hydrocarbyl substituent is a group chosen from polypropylene groups, polybutylene groups, polyalpha-olefin groups, and ethylene/alpha-olefin copolymer groups.

5 . The process of claim 2 , wherein the hydrocarbyl substituent is a copolymer group having at least one monomer chosen from butylene, isobutylene, and propylene, and at least one monomer chosen from mono-olefinic comonomers.

6 . The process of claim 2 , wherein the hydrocarbyl substituent is a polyisobutylene group.

7 . The process of claim 2 , wherein R 1 is methyl, R 2 is a hydrogen radical and R 3 is a polyisobutylene group.

8 . The process of claim 1 , wherein the at least one primary amine is a compound of formula (II),

where R 4 is a substituent chosen from alkyl, aryl, alkenyl, alkyl amino, dialkyl amino, alkylaminoalkyl, and dialkylaminoalkyl groups.

9 . The process of claim 8 , wherein R 4 is a -C 1-8 NR′R″ group, where the C 1-8 portion of the group is a straight or branched chain alkyl, and R′ and R″ are independently chosen from hydrogen radicals, methyl, ethyl, propyl and butyl groups.

10 . The process of claim 1 , wherein at least one primary amine is chosen from dimethylaminopropyl amine, diethylaminopropyl amine, and dimethylaminobutyl amine.

11 . The process of claim 1 , wherein the at least one aidehyde is chosen from formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, valeraldehyde, caproaldehyde, heptaldehyde, stearaldehyde, benzaldehyde, salicylaldehyde, furfural aldehyde, thiophene aldehyde, and paraformaldehyde.

12 . The process of claim 1 , wherein at least one hydroxyl substituted aromatic ring compound, the at least one primary amine and the at least one aldehyde are mixed in a ratio of about 1 mole of hydroxyl substituted aromatic ring compound; about 0.3 to about 0.7 moles of primary amine; and from about 0.8 to about 1.5 moles aldehyde.

13 . The process of claim 1 , wherein at least one second amine is a compound of formula (IV),

wherein R 5 and R 6 are each independently chosen from a hydrogen radical, alkyl, cycloalkyl, aryl, alkaryl, and aralkyl groups, with the proviso that at least one of R 5 and R 6 is not a hydrogen radical.

14 . The process of claim 1 , wherein at least one second amine is a compound of formula (V):

where R 7 is a linear, branched, or cyclic alkyl group having from 1 to 10 carbon atoms.

15 . The process of claim 14 , where R 7 is a saturated, straight chain hydrocarbon having 1 to 6 carbon atoms.

16 . The process of claim 14 , where R 7 is a substituted or unsubstituted cycloalkane having a 4 to 8 carbon member ring that is optionally substituted with one or more methyl, ethyl or propyl groups.

17 . The process of claim 1 , wherein the at least one second amine is chosen from dimethylamine, diethylamine, dipropylamine, dibutylamine, and dipentylamine.

18 . The process of claim 1 , wherein the at least one second amine is chosen from cyclohexaneamine; 1,3-propanediamine; 1,2 ethane diamine; 1,4-butanediamine; 1,6-hexanediamine; 1,2-diaminocyclohexane; 1,2-amino-3 methyl cyclohexane; 1,2 amino 4 methyl cyclohexane; N-methylamine methanediamine and 3,3 dimethyl amino propyl amine.

19 . A detergent base product formed by the method of claim 1 .

20 . A process for forming a Mannich reaction product, the process comprising:

reacting at least one amine compound chosen from primary and secondary amines with a bis-Mannich compound having a formula III,

where R 1 is chosen from a hydrogen radical and C 1-6 alkyl;

R 3 is a hydroxyaromatic compound having on the ring an aliphatic hydrocarbyl substituent derived from a polyolefin having a number average molecular weight of about 500 to about 3000; and

R 4 is a linear, branched, or cyclic, substituted or unsubstituted, saturated or unsaturated alkyl amine group.

21 . A fuel composition comprising:

a base fuel; and

a detergent base product comprising a mixture of formulae (VI) and (VII),

where R 1 and R 3 are substituents independently chosen from a hydrogen radical, C 1-6 alkyls and hydrocarbyl substituents having a number average molecular weight in the range of about 500 to about 3000, with the proviso that at least one of R 1 and R 3 is a hydrocarbyl substitutent,

R 4 is a substituent chosen from alkyl, aryl, alkenyl, alkyl amino, dialkyl amino, alkylaminoalkyl, and dialkylaminoalkyl groups,

R 5 and R 6 are each independently chosen from a hydrogen radical, alkyl, cycloalkyl, aryl, alkaryl, and aralkyl groups, with the proviso that at least one of R 5 and R 6 is not a hydrogen radical.