US 6,583,245 B1Granted

Polymeric stabilizers having low polydispersity

AssigneeCiba Specialty Chemicals Corporation

InventorsAlfred Steinmann, Michael Roth, Werner Stauffer, Peter Nesvadba, Andreas Mühlebach

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Abstract

The present invention relates to a polymerizable composition, comprising a) at least one compound of formula (I) (RG)—A—(Stab) (I), wherein (Stab) is a light stabilizer radical selected from the group consisting of sterically hindered amines, hydroxyphenyl-s-triazines, hydroxyphenyl-benzotriazols and o-hydroxy-benzophenones; A is a spacer group or a direct bond; and (RG) is a group containing at least one ethylenically unsaturated functional group; and either b1) a compound of formula (II) Y—X (II), wherein X represents a group having at least one carbon atom and is such that the free radical derived from X is capable of initiating polymerization and Y represents a group being such that the free radical Y· derived from it forms a stable free radical; or b2) a stable free radical Y· and a free radical source from which a radical is formed capable of initiating polymerization, or b3) a compound of formula (III) and a catalytically effective amount of an oxidizable transition metal complex catalyst, wherein p represents a number greater than zero and defines the number of initiator fragments; q represents a number greater than zero; [In] represents a radically transferable atom or group capable of initiating polymerization and -[Hal] represents a leaving group; and optionally c) one or more ethylenically unsaturated monomers or oligomers different from those of formula (I). Further subjects of the invention are a polymerization process, the polymers, copolymers oligomers and cooligomers obtainable by this process and the use of the polymers, copolymers oligomers and cooligomers as heat or light stabilizers.

Claims21

Dependent claims

A polymerizable composition, comprising

a) at least one compound of formula (I)
(RG)—A—(Stab) (I)
wherein
(Stab) is a light stabilizer radical selected from the group consisting of sterically hindered amines, hydroxyphenyl-s-triazines, hydroxyphenyl-benzotriazols and o-hydroxy-benzophenones;
A is a spacer group or a direct bond;
and
(RG) is a group containing at least one ethylenically unsaturated functional group;
and
a compound selected from the group consisting of
b1) a compound of formula (II)
Y—X (II)
which contains a structural element>N—O—X where the nitrogen atom is part of a cyclic ring system or is substituted to form an acyclic structure, and wherein X represents a group having at least one carbon atom and is such that the free radical derived from X is capable of initiating polymerization;
and a compound selected from the group consisting of
b2) a stable free radical having a structural element>N—O· where the nitrogen atom is part of a cyclic ring system or is substituted to form an acyclic structure and
a free radical source from which a radical is formed capable of initiating polymerization;
b3) a compound of formula (III)
and
a catalytically effective amount of an oxidizable transition metal complex catalyst where the transition metal is present as a transition metal complex ion in the lower oxidation state of a redox system;
wherein
[In] represents a polymerization initiator fragment of a polymerization initiator of formula (III) capable of initiating polymerization of monomers or oligomers, which polymerization initiator is selected from the group consisting of C1-C8-alkyl halides, C6-C15-aralkylhalides, C2-C8α-haloalkyl esters, arene sulfonyl chlorides, haloalkanenitriles, α-haloacrylates and halolactones;
p and q represent one;
and
-[Hal] represents a leaving group;
and optionally
c) one or more ethylenically unsaturated monomers or oligomers different from those of formula (I).

22 more elements

A process for preparing an oligomer, cooligomer, polymer or copolymer with a polydispersity Mw/Mn between 1 and 3, which process comprises reacting a composition of

a) at least one compound of formula (I)
(RG)—A—(Stab) (I)
wherein
(Stab) is a light stabilizer radical selected from the group consisting of sterically hindered amines, hydroxyphenyl-s-triazines, hydroxyphenyl-benzotriazols and o-hydroxy-benzophenones;
A is a spacer group or a direct bond;
and
(RG) is a group containing at least one ethylenically unsaturated functional group;
and a compound selected from the group consisting of
b1) a compound of formula (II)
Y—X (II)
which compound contains a structural element>N—O—X where the nitrogen atom is part of a cyclic ring system or is substituted to form an acyclic structure, and wherein X represents a group having at least one carbon atom and is such that the free radical derived from X is capable of initiating polymerization;
b2) a stable free radical having a structural element>N—O· where the nitrogen atom is part of a cyclic ring system or is substituted to form an acyclic structure and
a free radical source from which a radical is formed capable of initiating polymerization;
b3) a compound of formula (III)
a catalytically effective amount of an oxidizable transition metal complex catalyst, where the transition metal is present as a transition metal complex ion in the lower oxidation state of a redox system;
wherein
[In] represents a polymerization initiator fragment of a polymerization initiator of formula (III) capable of initiating polymerization of monomers or oligomers, which polymerization initiator is selected from the group consisting of C1-C8-alkyl halides, C6-C15-aralkylhalides, C2-C8α-haloalkyl esters, arene sulfonyl chlorides, haloalkanenitriles, α-haloacrylates and halolactones;
p and q represent one;
and
-[Hal] represents a leaving group;
and optionally simultaneously or in a subsequent step with
c) one or more ethylenically unsaturated monomers or oligomers different from those of formula (I), at a temperature between 50° C. and 180° C.

19 more elements

Dependencies are inferred from the claim text.