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US 11,161,807 B2Granted
Thermo-thickening compounds for non-polar liquid
AssigneesSorbonne Universite, Centre National De La Recherche Scientifique
InventorsVirgile Ayzac, Laurent Bouteiller, Matthieu Raynal, Benjamin Isare
Life of this patent
Estimating the term…
Abstract
A bis-urea compound of general formula (IV): The compound is useful as a thermo-thickening agent in a non-polar liquid such as engine lubricating oil or thermosetting varnish. Also, a method for preparing the thermo-thickening compound. Further, a composition comprising the thermo-thickening compound and a non-polar liquid.
Claims16
A method for thermo-thickening a composition comprising the addition to said composition of a compound of general formula (IV bis):
- wherein:
- Ra, Rb, Rc and Rd are each independently selected from H, alkyl, heteroalkyl, alkoxy, amino, alkylamino and halo;
- R1′ and R2′ are each independently selected from linear alkyl, heteroalkyl, alkenyl, heteroalkenyl, alkynyl, heteroalkynyl and macromolecular groups, substituted or not substituted by one or more halo;
- R3, R3, R4, and R4′ are each independently selected from H, alkyl, alkenyl, aryl, heteroalkyl, heteroalkenyl, heteroaryl, alkylaryl, arylalkyl, heteroarylalkyl or alkylheteroaryl, substituted or not substituted by guanidine, aryl, pyrrolidine, imidazole, hydroxyaryl, carboxy, selanyl, hydroxyl, amide, thiol, alkylthio, amino, deuterium or halo;
- Z1, Z1′, Z2, and Z2′ represent O atoms;
- and
- optionally, * stands for a stereogenic center;
- provided that R1′ and R2′ do not represent both a methyl group.
5 more elements
A compound of general formula (IV bis):
- wherein:
- Ra, Rb, Rc and Rd are each independently selected from H, alkyl, heteroalkyl, alkoxy, amino, alkylamino and halo;
- R1′ and R2′ are each independently selected from linear alkyl, heteroalkyl, alkenyl, heteroalkenyl, alkynyl, heteroalkynyl and macromolecular groups, substituted or not substituted by one or more halo;
- R3′, R3, R4 and R4′ are each independently selected from H, alkyl, alkenyl, aryl, heteroalkyl, heteroalkenyl, heteroaryl, alkylaryl, arylalkyl, heteroarylalkyl or alkylheteroaryl, substituted or not substituted by guanidine, aryl, pyrrolidine, imidazole, hydroxyaryl, carboxy, selanyl, hydroxyl, amide, thiol, alkylthio, amino, deuterium or halo;
- Z1, Z1′, Z2 and Z2′ represent O atoms;
- and
- optionally, * stands for a stereogenic center.
4 more elements
A process for manufacturing a compound of formula (IV bis):
- wherein:
- Ra, Rb, Rc and Rd are each independently selected from H, alkyl, heteroalkyl, alkoxy, amino, alkylamino and halo;
- R1′ and R2′ are each independently selected from linear alkyl, heteroalkyl, alkenyl, heteroalkenyl, alkynyl, heteroalkynyl and macromolecular groups, substituted or not substituted by one or more halo;
- R3′, R3, R4, and R4′ are each independently selected from H, alkyl, alkenyl, aryl, heteroalkyl, heteroalkenyl, heteroaryl, alkylaryl, arylalkyl, heteroarylalkyl or alkylheteroaryl, substituted or not substituted by guanidine, aryl, pyrrolidine, imidazole, hydroxyaryl, carboxy, selanyl, hydroxyl, amide, thiol, alkylthio, amino, deuterium or halo;
- Z1, Z1′, Z2 and Z2′ represent O atoms;
- and
- optionally, * stands for a stereogenic center;
- said process comprising reacting at least one ester ammonium salt of formula (A-1):
- wherein
- R3′ and R3 are each independently selected from H, alkyl, alkenyl, aryl, heteroalkyl, heteroalkenyl, heteroaryl, alkylaryl, arylalkyl, heteroarylalkyl or alkylheteroaryl, substituted or not substituted by guanidine, aryl, pyrrolidine, imidazole, hydroxyaryl, carboxy, selanyl, hydroxyl, amide, thiol, alkylthio, amino, deuterium or halo;
- R1′ is each independently selected from linear alkyl, heteroalkyl, alkenyl, heteroalkenyl, alkynyl and heteroalkynyl group, substituted or not substituted by one or more halo;
- and
- X− is an anion
- with
- (a) either a diisocyanate of general formula (A-2bis):
- wherein Ra, Rb, Rc and Rd are each independently selected from H, alkyl, heteroalkyl, alkoxy, amino, alkylamino and halo;
- (b) or a mixture of reagents allowing the in situ preparation of diisocyanate of formula (A-2bis).
14 more elements
Dependencies are inferred from the claim text.