US2006196107A1PendingUtilityA1

Cyclic mannich products

48
Assignee: MALFER DENNIS JPriority: Mar 4, 2005Filed: Mar 4, 2005Published: Sep 7, 2006
Est. expiryMar 4, 2025(expired)· nominal 20-yr term from priority
Inventors:Dennis J. MalferMay Duffield ThomasRoger M. Sheets
C10L 10/06C10L 10/18C10L 1/233C10L 10/04C10L 1/1985C10L 1/143
48
PatentIndex Score
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Claims

Abstract

The present teachings relate to fuel additives useful for reducing and/or preventing the formation of intake valve deposits. The fuel additives include cyclic Mannich products prepared by the reaction of (A) a substituted hydroxyaromatic compound, (B) a formaldehyde source, and (C) a primary amine.

Claims

exact text as granted — not AI-modified
1 . A compound of formula (I):  
       
         
           
           
               
               
           
         
         wherein R 1  R 3 , R 4 , and R 5  are each independently chosen from H and substituted and unsubstituted hydrocarbyl radicals, wherein the substituents are chosen from halogen, hydroxyl, alkyl, alkenyl, alkynyl, nitro, and amino radicals;  
         R 2  is chosen from substituted and unsubstituted hydrocarbyl radicals having a number average molecular weight ranging from 500 to 3000, wherein the substituents are chosen from halogen, hydroxyl, alkyl, alkenyl, alkynyl, nitro, and amino radicals; and  
         R 6  and R 7  are each independently chosen from H and C 1 -C 5  hydrocarbyl radicals.  
       
     
     
         2 . The compound according to  claim 1 , wherein R 1  is chosen from unsubstituted alkyl radicals.  
     
     
         3 . The compound according to  claim 1 , wherein R 1  is methyl.  
     
     
         4 . The compound according to  claim 1 , wherein R 2  is chosen from unsubstituted alkenyl radicals.  
     
     
         5 . The compound according to  claim 1 , wherein R 2  is a polyisobutyl radical.  
     
     
         6 . The compound according to  claim 1 , wherein R 5  is chosen from aminoalkyl radicals.  
     
     
         7 . The compound according to  claim 1 , wherein R 5  is an N,N-dimethylaminopropyl radical.  
     
     
         8 . The compound according to  claim 1 , wherein R 3 , R 4 , R 6  and R 7  are hydrogen.  
     
     
         9 . The compound according to  claim 1 , wherein said compound is:  
       
         
           
           
               
               
           
         
       
     
     
         10 . A process for preparing a compound of formula (I):  
       
         
           
           
               
               
           
         
       
       comprising reacting a compound of formula (II):  
       
         
           
           
               
               
           
         
         with (A) a formaldehyde source, (B) optionally a ketone, and (C) a primary amine to yield the compound of formula (I),  
         wherein R 1 , R 3 , R 4  and R 5  are each independently chosen from H and substituted and unsubstituted hydrocarbyl radicals, wherein the substituents are chosen from halogen, hydroxyl, alkyl, alkenyl, alkynyl, nitro, and amino radicals;  
         R 2  is chosen from substituted and unsubstituted hydrocarbyl radicals having a number average molecular weight ranging from 500 to 3000, wherein the substituents are chosen from halogen, hydroxyl, alkyl, alkenyl, alkynyl, nitro, and amino radicals; and  
         R 6  and R 7  are each independently chosen from H and C 1 -C 5  hydrocarbyl radicals.  
       
     
     
         11 . The process according to  claim 10 , wherein the formaldehyde source is chosen from paraformaldehyde, aqueous formaldehyde compositions, and compositions comprising formaldehyde and methanol.  
     
     
         12 . The process according to  claim 10 , wherein the ketone is a compound of formula (III):  
       
         
           
           
               
               
           
         
       
     
     
         13 . The process according to  claim 10 , wherein the primary amine is chosen from aliphatic polyamines.  
     
     
         14 . The process according to  claim 13 , wherein the aliphatic polyamine is chosen from N,N-dialkyl-α,ω-alkylenediamines.  
     
     
         15 . The process according to  claim 14 , wherein the N,N-dialkyl-α,ω-alkylenediamine is N,N-dimethyl-1,3-propanediamine.  
     
     
         16 . The process according to  claim 10 , wherein the compound of formula (II), (A), and (C) are reacted in a molar ratio of 1:2:1.  
     
     
         17 . The process according to  claim 10 , wherein R 1  is methyl, R 2  is polyisobutyl, R 3 , R 4 , R 6 , and R 7  are H, R 5  is N,N-dimethylaminopropyl, and the primary amine is dimethylaminopropylamine.  
     
     
         18 . A fuel additive composition comprising a compound according to  claim 1 .  
     
     
         19 . A fuel additive composition comprising a compound according to  claim 9 .  
     
     
         20 . A fuel additive composition comprising a cyclic Mannich product prepared by the reaction of: 
 (A) a substituted hydroxyaromatic compound having at least one unsubstituted position ortho to the hydroxy group,    (B) a formaldehyde source, and    (C) a primary amine.    
     
     
         21 . The fuel additive composition according to  claim 20 , wherein the substituted hydroxyaromatic compound is one mole part of a phenol substituted with a hydrocarbyl substituent, in which said hydrocarbyl substituent is derived from polypropylene, polybutylene or a copolymer of propylene and butylenes having a number average molecular weight ranging from 500 to 3000 and a polydispersity in the range of 1 to 4.  
     
     
         22 . The fuel additive composition according to  claim 20 , wherein the substituted hydroxyaromatic compound is polyisobutylcresol and the primary amine is dimethylaminopropylamine.  
     
     
         23 . The fuel additive composition according to  claim 20 , further comprising a liquid carrier.  
     
     
         24 . The fuel additive composition according to  claim 23 , wherein the liquid carrier is at least one fuel-soluble poly(oxyalkylene) compound.  
     
     
         25 . The fuel additive composition according to  claim 24 , wherein the weight ratio of said poly(oxyalkylene) compound to the cyclic Mannich product on an active ingredient basis is 2.0:1.0 or less.  
     
     
         26 . A fuel composition for use in spark ignition internal combustion engines into which has been blended from 5 to 2000 ptb of a fuel additive composition according to  claim 20 .  
     
     
         27 . A fuel composition comprising: 
 (A) a fuel in a major amount, and    (B) a compound according to  claim 1  in a minor amount.    
     
     
         28 . The fuel composition according to  claim 27 , wherein the fuel comprises gasoline.  
     
     
         29 . The fuel composition according to  claim 27 , further comprising at least one additive chosen from dispersants, detergents, antioxidants, carrier fluids, metal deactivators, dyes, markers, corrosion inhibitors, biocides, antistatic additives, drag-reducing agents, demulsifiers, dehazers, anti-icing additives, anti-knock additives, anti-valve-seat recession additives, friction modifiers, lubricity additives, multifunctional additives, and combustion improvers.  
     
     
         30 . A fuel composition comprising: 
 (A) a fuel in a major amount, and    (B) a compound according to  claim 9  in a minor amount.    
     
     
         31 . The fuel composition according to  claim 30 , wherein the fuel comprises gasoline.  
     
     
         32 . The fuel composition according to  claim 30 , further comprising at least one additive chosen from dispersants, detergents, antioxidants, carrier fluids, metal deactivators, dyes, markers, corrosion inhibitors, biocides, antistatic additives, drag-reducing agents, demulsifiers, dehazers, anti-icing additives, anti-knock additives, anti-valve-seat recession additives, friction modifiers, lubricity additives, multifunctional additives, and combustion improvers.  
     
     
         33 . A method for reducing and/or preventing the formation of intake valve deposits in an engine, comprising fueling and operating said engine with a fuel composition according to  claim 27 .  
     
     
         34 . A method for reducing and/or preventing the formation of intake valve deposits in an engine, comprising fueling and operating said engine with a fuel composition according to  claim 30 .  
     
     
         35 . An engine combusting a fuel composition according to  claim 27 .  
     
     
         36 . An engine combusting a fuel composition according to  claim 30.

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