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US 6,632,895 B1Granted
Functionalized alkoxyamine initiators
AssigneeBayer Aktiengesellschaft
InventorsMartin Melchiors, Hartwig Höcker, Helmut Keul, Dirk Achten
Life of this patent
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Abstract
The invention relates to a new process for the preparation of functionalized alkoxyamine initiators, new alkoxyamine initiators based on (meth)acrylate which are prepared by this process, and their use for the preparation of polymers.
Claims11
A process for the preparation of mono- and difunctional alkoxyamine initiators of the formula (I)
- wherein
- R1, R2 and R3 are the same or different and represent H, C1-C20-(cyclo)alkyl, C6-C24-aryl, halogen, CN, C1-C20-(cyclo)alkyl ester or -amide or C6-C24-aryl ester or -amide, and
- R4 and R5 are the same or different and represent aliphatic, cycloaliphatic or mixed aliphatic/aromatic radicals having 1 to 24 carbon atoms, which can also be part of a 4- to 8-membered ring,
- wherein the carbon atom of the radicals R4 and R5 directly adjacent to the alkoxyamine nitrogen atom is in each case substituted by 3 further organic substituents (i.e. not hydrogen) or a double-bonded carbon, oxygen, sulfur or nitrogen atom and a further organic substituent (not hydrogen), and
- wherein at least one of the radicals R4 and R5 can contain a functional group Y selected from the group consisting of hydroxy, primary amine, secondary amine and epoxide,
- wherein
- A) a monomer which can be polymerized by free radicals, of the formula (M)
- HR1C═CR2R3,
- is reacted with
- B) a system, which produces free radicals, of
- B1) a compound having a reducing action,
- B2) a compound which can be split into one or more free radicals by the action of component B1,
- B3) a cyclic or acyclic nitroxide of the formula (N)
- R4R5NO
- in a solvent.
12 more elements
Alkoxyamine initiators of the formula (II)
- wherein
- R4 and R5 are the same or different and represent aliphatic, cycloaliphatic or mixed aliphatic/aromatic radicals having 1 to 24 carbon atoms, which can also be part of a 4- to 8-membered ring,
- wherein the carbon atom of the radicals R4 and R5 directly adjacent to the alkoxyamine nitrogen atom is in each case substituted by 3 further organic substituents (i.e. not hydrogen) or a double-bonded carbon, oxygen, sulfur or nitrogen atom and a further organic substituent (not hydrogen), and
- wherein at least one of the radicals R4 and R5 can contain a functional group Y selected from the group consisting of hydroxy, primary amine, secondary amine and epoxide,
- R6 represents H or a C1-C20-(cyclo)alkyl radical and
- R7 represents a linear or branched C1-C24-(cyclo)alkyloxocarbonyl radical (i.e. a (cyclo)aliphatic ester group) or CN.
3 more elements
Alkoxyamine initiators of the formula (IIb)
- wherein
- R8, R9, R10 and R11 are the same or different and represent C1-C20-(cyclo)alkyl or C6-C24-aryl radicals or C7-C24-aliphatic/aromatic hydrocarbon radicals, which can additionally contain cyano groups, ether groups, amide groups or OH groups and can also be part of a ring structure,
- R17 represents hydrogen or a group selected from the group consisting of hydroxy, primary, amine, secondary amine and epoxide
- R18 is a (cyclo)aliphatic alkyl group having 1 to 20 carbon atoms and
- R19 is H or CH3.
2 more elements
Dependencies are inferred from the claim text.