CA2262435A1 - Preparation of sterically hindered amine ethers - Google Patents
Preparation of sterically hindered amine ethers Download PDFInfo
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- CA2262435A1 CA2262435A1 CA002262435A CA2262435A CA2262435A1 CA 2262435 A1 CA2262435 A1 CA 2262435A1 CA 002262435 A CA002262435 A CA 002262435A CA 2262435 A CA2262435 A CA 2262435A CA 2262435 A1 CA2262435 A1 CA 2262435A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/94—Oxygen atom, e.g. piperidine N-oxide
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0066—Flame-proofing or flame-retarding additives
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
- C08K5/34926—Triazines also containing heterocyclic groups other than triazine groups
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/30—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing heterocyclic ring with at least one nitrogen atom as ring member
Abstract
A new process is described for the preparation of a compound of the formula I
wherein R1, R2, R3 and R4, independently of each other, are C1-C8alkyl or C1-C5hydroxyalkyl, or R1 and R2 together with the carbon atom they are attached to are C5-C12cycloalkyl, or R3 and R4 together with the carbon atom they are attached to are C5-C12cycloalkyl;
R5, R6, R7, R8 and R9, independently of each other, are H, C1-C8alkyl, C5-C12alkenyl, C5-C2aryl, C1-C4haloalkyl, an electron withdrawing group, or C6-C12aryl which is substituted by a residue selected from C1-C4alkyl, C1-C4alkoxy, halogen; and R7 and R8 together may also form a chemical bond; and R is an organic linking group containing 2-500 carbon atoms and forming, together with the carbon atoms it is directly connected to and the nitrogen atom, a substituted, 5-, 6 or 7-membered cyclic ring structure; characterized in that a compound of the formula II
is oxidized. The compound of the formula I can be hydrogenated and/or halogenated by conventional methods.
Compounds of the formula I and the corresponding hydrogenated and/or halogenated compounds are well suitable as stabilizers for organic material against degradation by light, oxygen and/or heat or yellowing; some are also active as flame retardants.
wherein R1, R2, R3 and R4, independently of each other, are C1-C8alkyl or C1-C5hydroxyalkyl, or R1 and R2 together with the carbon atom they are attached to are C5-C12cycloalkyl, or R3 and R4 together with the carbon atom they are attached to are C5-C12cycloalkyl;
R5, R6, R7, R8 and R9, independently of each other, are H, C1-C8alkyl, C5-C12alkenyl, C5-C2aryl, C1-C4haloalkyl, an electron withdrawing group, or C6-C12aryl which is substituted by a residue selected from C1-C4alkyl, C1-C4alkoxy, halogen; and R7 and R8 together may also form a chemical bond; and R is an organic linking group containing 2-500 carbon atoms and forming, together with the carbon atoms it is directly connected to and the nitrogen atom, a substituted, 5-, 6 or 7-membered cyclic ring structure; characterized in that a compound of the formula II
is oxidized. The compound of the formula I can be hydrogenated and/or halogenated by conventional methods.
Compounds of the formula I and the corresponding hydrogenated and/or halogenated compounds are well suitable as stabilizers for organic material against degradation by light, oxygen and/or heat or yellowing; some are also active as flame retardants.
Claims (18)
1. Process for the preparation of a compound of the formula I
wherein R1, R2, R3 and R4, independently of each other, are C1-C8alkyl or C1-C5hydroxyalkyl, or R1 and R2 together with the carbon atom they are attached to are C5-C12cycloalkyl, or R3 and R4 together with the carbon atom they are attached to are C5-C12cycloalkyl;
R5, R6, R7, R8 and R9, independently of each other, are H, C1-C8alkyl, C2-C8alkenyl, C5-C12aryl, C1-C4haloalkyl, an electron withdrawing group, or C6-C12aryl which is substituted by a residue selected from C1-C4alkyl, C1-C4alkoxy, halogen; and R7 and R8 together may also form a chemical bond; and R is an organic linking group containing 2-500 carbon atoms and forming, together with the carbon atoms it is directly connected to and the nitrogen atom, a substituted, 5-, 6 or 7-membered cyclic ring structure;
characterized in that a compound of the formula II
wherein all residues R and R1-R9 are as defined for formula I, is oxidized.
wherein R1, R2, R3 and R4, independently of each other, are C1-C8alkyl or C1-C5hydroxyalkyl, or R1 and R2 together with the carbon atom they are attached to are C5-C12cycloalkyl, or R3 and R4 together with the carbon atom they are attached to are C5-C12cycloalkyl;
R5, R6, R7, R8 and R9, independently of each other, are H, C1-C8alkyl, C2-C8alkenyl, C5-C12aryl, C1-C4haloalkyl, an electron withdrawing group, or C6-C12aryl which is substituted by a residue selected from C1-C4alkyl, C1-C4alkoxy, halogen; and R7 and R8 together may also form a chemical bond; and R is an organic linking group containing 2-500 carbon atoms and forming, together with the carbon atoms it is directly connected to and the nitrogen atom, a substituted, 5-, 6 or 7-membered cyclic ring structure;
characterized in that a compound of the formula II
wherein all residues R and R1-R9 are as defined for formula I, is oxidized.
2. Process according to claim 1, wherein the oxidation reaction is carried out in presence of a solvent and an oxidant selected from oxygen, peroxides, nitrates, permanganates, chlorates.
3. Process according to claim 1 for the preparation of a compound of formula I
by oxidation of a compound of formula II, wherein R1, R2, R3 and R4, independently of each other, are C1-C8alkyl or C1-C5hydroxyalkyl, or R1 and R2 together with the carbon atom they are attached to are C5-C12cycloalkyl, or R3 and R4 together with the carbon atom they are attached to are C5-C12cycloalkyl;
R5, R6, R7, R8 and R9, independently of each other, are H, C1-C4alkyl, C3-C4alkenyl, C5-C12aryl, an electron withdrawing group, C6-C12aryl which is substituted by C1-C4alkyl, C1-C4alkoxy, halogen; and R is a C3-C500hydrocarbon optionally containing 1-200 hetero atoms selected from nitrogen, oxygen, phosphorus, sulfur and halogen, and forming, together with the two carbon and the nitrogen atom, a substituted, 6-membered cyclic ring structure.
by oxidation of a compound of formula II, wherein R1, R2, R3 and R4, independently of each other, are C1-C8alkyl or C1-C5hydroxyalkyl, or R1 and R2 together with the carbon atom they are attached to are C5-C12cycloalkyl, or R3 and R4 together with the carbon atom they are attached to are C5-C12cycloalkyl;
R5, R6, R7, R8 and R9, independently of each other, are H, C1-C4alkyl, C3-C4alkenyl, C5-C12aryl, an electron withdrawing group, C6-C12aryl which is substituted by C1-C4alkyl, C1-C4alkoxy, halogen; and R is a C3-C500hydrocarbon optionally containing 1-200 hetero atoms selected from nitrogen, oxygen, phosphorus, sulfur and halogen, and forming, together with the two carbon and the nitrogen atom, a substituted, 6-membered cyclic ring structure.
4. Process according to claim 1, wherein in the compounds of formulae I and II
R1, R2, R3 and R4 independently preferably are methyl or ethyl, R5 and R6 independently are H or methyl, and R7, R8 and R9 independently are C1-C4haloalkyl, phenyl, vinyl, nitro, CN, COOR10, or R7 and R8 together form a chemical bond, and the linking group R is a C2-C500hydrocarbon or a C2-C500 hydrocarbon containing 1-200 hetero atoms selected from nitrogen, oxygen, phosphorus, sulfur, silicon and halogen.
R1, R2, R3 and R4 independently preferably are methyl or ethyl, R5 and R6 independently are H or methyl, and R7, R8 and R9 independently are C1-C4haloalkyl, phenyl, vinyl, nitro, CN, COOR10, or R7 and R8 together form a chemical bond, and the linking group R is a C2-C500hydrocarbon or a C2-C500 hydrocarbon containing 1-200 hetero atoms selected from nitrogen, oxygen, phosphorus, sulfur, silicon and halogen.
5. Process for the preparation of a compound of the formula V
wherein R, R1, R2, R3 and R4, R5, R6, and R9 are as defined for formula I in claim 1, R7 and R8 are H, C1-C8alkyl, C3-C8alkenyl, C5-C12aryl, C1-C4haloalkyl, halogen, an electron withdrawing group, or C6-C12aryl which is substituted by a residue selected from C1-C4alkyl, C1-C4alkoxy, halogen; and both of R20 and R21 are either hydrogen or halogen; characterized in that a compound of the formula II as described in claim 1 is oxidized and the resulting intermediate of formula I is subjected to hydrogenation and/or halogenation.
wherein R, R1, R2, R3 and R4, R5, R6, and R9 are as defined for formula I in claim 1, R7 and R8 are H, C1-C8alkyl, C3-C8alkenyl, C5-C12aryl, C1-C4haloalkyl, halogen, an electron withdrawing group, or C6-C12aryl which is substituted by a residue selected from C1-C4alkyl, C1-C4alkoxy, halogen; and both of R20 and R21 are either hydrogen or halogen; characterized in that a compound of the formula II as described in claim 1 is oxidized and the resulting intermediate of formula I is subjected to hydrogenation and/or halogenation.
6. Composition comprising A) an organic polymer which is sensitive to oxidative, thermal and/or actinic degradation, and B) at least one compound of the formula IIIa, IVa or Va wherein R' and R each is an organic linking group of the formula E2 is -CO- or -(CH2)p-, where p is 0, 1 or 2;
E1 is a carbon atom carrying the two residues R24 and R25, or is >N-R25, or is oxygen, and R24 and R25 are hydrogen or an organic residue, characterized in that the linking group R in total contains 2-500 carbon atoms;
R1, R2, R3 and R4, independently of each other, are C1-C5alkyl or C1-C5hydroxyalkyl, or R1 and R2 together with the carbon atom they are attached to are C5-C12cycloalkyl, or R3 and R4 together with the carbon atom they are attached to are C5-C12cycloalkyl;
R5, R6, R7, R8 and R9, independently of each other, are H, C1-C8alkyl, C2-C8alkenyl, C5-C12aryl, C1-C4haloalkyl, an electron withdrawing group, or C6-C12aryl which is substituted by a residue selected from C1-C4alkyl, C1-C4alkoxy, halogen;
R20 and R21 are halogen; and R22 and R23 are hydrogen or together are a chemical bond.
E1 is a carbon atom carrying the two residues R24 and R25, or is >N-R25, or is oxygen, and R24 and R25 are hydrogen or an organic residue, characterized in that the linking group R in total contains 2-500 carbon atoms;
R1, R2, R3 and R4, independently of each other, are C1-C5alkyl or C1-C5hydroxyalkyl, or R1 and R2 together with the carbon atom they are attached to are C5-C12cycloalkyl, or R3 and R4 together with the carbon atom they are attached to are C5-C12cycloalkyl;
R5, R6, R7, R8 and R9, independently of each other, are H, C1-C8alkyl, C2-C8alkenyl, C5-C12aryl, C1-C4haloalkyl, an electron withdrawing group, or C6-C12aryl which is substituted by a residue selected from C1-C4alkyl, C1-C4alkoxy, halogen;
R20 and R21 are halogen; and R22 and R23 are hydrogen or together are a chemical bond.
7. A composition according to claim 6 comprising as organic polymer a thermoplastic organic polymer or a binder for a coating.
8. A composition according to claim 6 comprising from 0.1 to 10 % by weight, based on the material to be stabilized, of the stabilizer of component B.
9. A composition according to claim 6 comprising a further component selected from solvents, pigments, dyes, plasticizers, antioxidants, stabilizers, thixotropic agents, levelling assistants, further light stabilizers, metal passivators, phosphates and phosphonites.
10. A composition according to claim 9 comprising a further component a UV
absorber selected from the 2-hydroxyphenyl-benzotriazoles, the 2-hydroxyphenyl-s-triazines, the benzophenones.
absorber selected from the 2-hydroxyphenyl-benzotriazoles, the 2-hydroxyphenyl-s-triazines, the benzophenones.
11. Compound of the formula Ia in which the index n ranges from 1 to 15;
R5, R6, R7, R8 and R9, independently of each other, are C1-C8alkyl, C3-C8alkenyl, C5-C12aryl, an electron withdrawing group, C6-C12aryl which is substituted by C1-C4alkyl, C1-C4alkoxy, halogen;
R12 is C2-C12alkylene, C4-C12alkenylene, C5-C7cycloalkylene, C5-C7cycloalkylene-di(C1-C4alkylene), C1-C4alkylenedi(C5-C7cycloalkylene), phenylenedi(C1-C4alkylene) or C4-C12alkylene interrupted by 1,4-piperazinediyl, -O- or >N-X1 with X1 being C1-C12acyl or (C1-C12alkoxy)carbonyl or having one of the definitions of R14 given below except hydrogen;
or R12 is a group of the formula (Ib') or (Ic');
with m being 2 or 3, X2 being C1-C18alkyl, C5-C12cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl; phenyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl or C1-C4alkoxy; C7-C9phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4alkyl; and the radicals X3 being independently of one another C2-C12alkylene;
the radicals A are independently of one another -OR13, -N(R14)(R15) or a group of the formula (Id');
R13, R14 and R15, which are identical or different, are hydrogen, C1-C18alkyl, C5-C12cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl; C3-C18alkenyl, phenyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl or C1-C4alkoxy; C7-C9phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4alkyl;
tetrahydrofurfuryl or C2-C4alkyl which is substituted in the 2, 3 or 4 position by -OH, C1-C8alkoxy, di(C1-C4alkyl)amino or a group of the formula (Ie');
with Y being -O-, -CH2-, -CH2CH2- or >N-CH3, or -N(R14)(R15) is additionally a group of the formula (Ie');
X is -O- or >N-R16;
R16 is hydrogen, C1-C18alkyl, C3-C12alkenyl, C5-C12cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl; C7-C9phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4alkyl; tetrahydrofurfuryl, a group of the formula (If'), or C2-C4alkyl which is substituted in the 2, 3 or 4 position by -OH, C1-C8alkoxy;
di(C1-C4alkyl)amino or a group of the formula (Ie');
R11 has one of the definitions given for R16; and the radicals B have independently of one another one of the definitions given for A.
R5, R6, R7, R8 and R9, independently of each other, are C1-C8alkyl, C3-C8alkenyl, C5-C12aryl, an electron withdrawing group, C6-C12aryl which is substituted by C1-C4alkyl, C1-C4alkoxy, halogen;
R12 is C2-C12alkylene, C4-C12alkenylene, C5-C7cycloalkylene, C5-C7cycloalkylene-di(C1-C4alkylene), C1-C4alkylenedi(C5-C7cycloalkylene), phenylenedi(C1-C4alkylene) or C4-C12alkylene interrupted by 1,4-piperazinediyl, -O- or >N-X1 with X1 being C1-C12acyl or (C1-C12alkoxy)carbonyl or having one of the definitions of R14 given below except hydrogen;
or R12 is a group of the formula (Ib') or (Ic');
with m being 2 or 3, X2 being C1-C18alkyl, C5-C12cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl; phenyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl or C1-C4alkoxy; C7-C9phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4alkyl; and the radicals X3 being independently of one another C2-C12alkylene;
the radicals A are independently of one another -OR13, -N(R14)(R15) or a group of the formula (Id');
R13, R14 and R15, which are identical or different, are hydrogen, C1-C18alkyl, C5-C12cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl; C3-C18alkenyl, phenyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl or C1-C4alkoxy; C7-C9phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4alkyl;
tetrahydrofurfuryl or C2-C4alkyl which is substituted in the 2, 3 or 4 position by -OH, C1-C8alkoxy, di(C1-C4alkyl)amino or a group of the formula (Ie');
with Y being -O-, -CH2-, -CH2CH2- or >N-CH3, or -N(R14)(R15) is additionally a group of the formula (Ie');
X is -O- or >N-R16;
R16 is hydrogen, C1-C18alkyl, C3-C12alkenyl, C5-C12cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl; C7-C9phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4alkyl; tetrahydrofurfuryl, a group of the formula (If'), or C2-C4alkyl which is substituted in the 2, 3 or 4 position by -OH, C1-C8alkoxy;
di(C1-C4alkyl)amino or a group of the formula (Ie');
R11 has one of the definitions given for R16; and the radicals B have independently of one another one of the definitions given for A.
12. Compound of the formula IIIc, IVa or Va , wherein R is an organic linking group of the formula E2 is -CO- or -(CH2)P-, where p is 0, 1 or 2;
E1 is a carbon atom carrying the two residues R24 and R25, or is >N-R25, or is oxygen, and R24 and R25 are hydrogen or an organic residue, characterized in that the linking group R in total contains 2-500 carbon atoms and forms, together with the carbon atoms it is directly connected to it and the nitrogen atom, a substituted, 5-, 6 or 7-membered cyclic ring structure;
R1, R2, R3 and R4, independently of each other, are C1-C8alkyl or C1-C5hydroxyalkyl, or R1 and R2 together with the carbon atom they are attached to are C5-C12cycloalkyl, or R3 and R4 together with the carbon atom they are attached to are C5-C12cycloalkyl;
R5, R6, R7, R8 and R9, independently of each other, are H, C1-C8alkyl, C2-C8alkenyl, C5-C12aryl, C1-C4haloalkyl, an electron withdrawing group, or C6-C12aryl which is substituted by a residue selected from C1-C4alkyl, C1-C4alkoxy, halogen;
R20 and R21 are halogen; and R22 and R23 are hydrogen or together are a chemical bond, with the proviso that R in formula IIIc is not the linking group wherein R24 and R25 together are =O or wherein R24 is hydrogen and R25 is hydrogen, OH, or alkanoyloxy which is substituted by phenoxy or alkylphenoxy.
E1 is a carbon atom carrying the two residues R24 and R25, or is >N-R25, or is oxygen, and R24 and R25 are hydrogen or an organic residue, characterized in that the linking group R in total contains 2-500 carbon atoms and forms, together with the carbon atoms it is directly connected to it and the nitrogen atom, a substituted, 5-, 6 or 7-membered cyclic ring structure;
R1, R2, R3 and R4, independently of each other, are C1-C8alkyl or C1-C5hydroxyalkyl, or R1 and R2 together with the carbon atom they are attached to are C5-C12cycloalkyl, or R3 and R4 together with the carbon atom they are attached to are C5-C12cycloalkyl;
R5, R6, R7, R8 and R9, independently of each other, are H, C1-C8alkyl, C2-C8alkenyl, C5-C12aryl, C1-C4haloalkyl, an electron withdrawing group, or C6-C12aryl which is substituted by a residue selected from C1-C4alkyl, C1-C4alkoxy, halogen;
R20 and R21 are halogen; and R22 and R23 are hydrogen or together are a chemical bond, with the proviso that R in formula IIIc is not the linking group wherein R24 and R25 together are =O or wherein R24 is hydrogen and R25 is hydrogen, OH, or alkanoyloxy which is substituted by phenoxy or alkylphenoxy.
13. Compound according to claim 12, wherein R is a divalent C7-C500 hydrocarbon or a C2-C500hydrocarbon containing 1-200 hetero atoms selected from nitrogen, oxygen, phosphorus, sulfur, silicon and halogen, and conforms to the structure , or where p is 0, 1 or 2;
R1, R2, R3 and R4, independently of each other, are C1-C8alkyl or C1-C5hydroxyalkyl, or R1 and R2 together with the carbon atom they are attached to are C5-C12cycloalkyl, or R3 and R4 together with the carbon atom they are attached to are C5-C12cycloalkyl;
R5 and R6 independently are H or methyl; and R7, R8 and R9 independently are C1-C4haloalkyl, phenyl, vinyl, nitro, CN, COOR10, where R10 is C1-C12alkyl, C5-C12cycloalkyl or phenyl;
R24 and R25 independently are hydrogen or an organic residue as defined, and R26 is hydrogen or an organic residue forming, together with the remaining structure of formula (VIb) a C2-C500hydrocarbon containing 1-200 hetero atoms selected from nitrogen, oxygen, phosphorus, sulfur, silicon and halogen.
R1, R2, R3 and R4, independently of each other, are C1-C8alkyl or C1-C5hydroxyalkyl, or R1 and R2 together with the carbon atom they are attached to are C5-C12cycloalkyl, or R3 and R4 together with the carbon atom they are attached to are C5-C12cycloalkyl;
R5 and R6 independently are H or methyl; and R7, R8 and R9 independently are C1-C4haloalkyl, phenyl, vinyl, nitro, CN, COOR10, where R10 is C1-C12alkyl, C5-C12cycloalkyl or phenyl;
R24 and R25 independently are hydrogen or an organic residue as defined, and R26 is hydrogen or an organic residue forming, together with the remaining structure of formula (VIb) a C2-C500hydrocarbon containing 1-200 hetero atoms selected from nitrogen, oxygen, phosphorus, sulfur, silicon and halogen.
14. Compound according to claim 12 corresponding to the formulae (1a), (1b) or (2a) or containing at least one group of the formula (3) or (4) , , , in which n1 is a number from 1 to 4, G and G1, independently of one another, are hydrogen or methyl, G11 is n-propoxy, O-CH=C=CH2, O-CH=CH-CH3 or halogenated n-propoxy, especially n-propoxy, or brominated n-propoxy;
G12, if n1 is 1, is C1-C18alkyl which is uninterrupted or interrupted by one or more oxygen atoms, cyanoethyl, benzoyl, glycidyl, a monovalent radical of an aliphatic, cycloaliphatic, unsaturated or aromatic carboxylic acid, carbamic acid or phosphorus-containing acid or a monovalent silyl radical, preferably a radical of an aliphatic carboxylic acid having 2 to 18 carbon atoms, of a cycloaliphatic carboxylic acid having 7 to 15 carbon atoms, or an .alpha.,.beta.-unsaturated carboxylic acid having 3 to 5 carbon atoms, where each carboxylic acid can be substituted in the aliphatic, cycloaliphatic or aromatic moiety, if present, by 1 to 3 -COOZ12 groups, in which Z12 is H, C1-C20alkyl, C3-C12alkenyl, C5-C7cycloalkyl, phenyl or benzyl, G12, if n1 is 2, is C2-C12alkylene, C4-C12alkenylene, xylylene, a divalent radical of an aliphatic, cycloaliphatic, araliphatic or aromatic dicarboxylic acid, dicarbamic acid or phosphorus-containing acid or a divalent silyl radical, preferably a radical of an aliphatic dicarboxylic acid having 2 to 36 carbon atoms, or a cycloaliphatic or aromatic dicarboxylic acid having 8-14 carbon atoms or of an aliphatic, cycloaliphatic or aromatic dicarbamic acid having 8-14 carbon atoms, where each dicarboxylic acid may be substituted in the aliphatic, cycloaliphatic or aromatic moiety by one or two -COOZ12 groups, G12, if n1 is 3, is a trivalent radical of an aliphatic, cycloaliphatic or aromatic tricarboxylic acid, which may be substituted in the aliphatic, cycloaliphatic or aromatic moiety by -COOZ12, of an aromatic tricarbamic acid or of a phosphorus-containing acid, or is a trivalent silyl radical, and G12, if n1 is 4, is a tetravalent radical of an aliphatic, cycloaliphatic or aromatic tetracarboxylic acid;
R1, R2, R3 and R4, independently of each other, are C1-C8alkyl or C1-C5hydroxyalkyl, or R1 and R2 together with the carbon atom they are attached to are C5-C12cycloalkyl, or R3 and R4 together with the carbon atom they are attached to are C5-C12cycloalkyl;
G is hydrogen or methyl;
G1 and G2, independently of one another, are hydrogen, methyl or together are a substituent =O; and G3 is a direct bond or methylene, open bonds of formulae (3) and (4) are linked to a carbon, nitrogen or oxygen atom of an organic residue as defined above, G13 is hydrogen, C1-C12alkyl, C2-C6hydroxyalkyl, C5-C7cycloalkyl, C7-C8aralkyl, C1-C18alkanoyl, C3-C5alkenoyl, benzoyl or a group of the formula (1b-1) n2 is the number 1, 2 or 3;
and G14, if n2 is 1, is hydrogen, C1-C18alkyl, C3-C8alkenyl, C5-C7cycloalkyl, C1-C4alkyl which is substituted by a hydroxyl, cyano, alkoxycarbonyl or carbamide group, glycidyl, a group of the formula -CH2-CH(OH)-Z or of the formula -CONH-Z, in which Z is hydrogen, methyl or phenyl;
G14, if n2 is 2, is C2-C12alkylene, C6-C12arylene, xylylene, a -CH2-CH(OH)-CH2 group or a -CH2-CH(OH)-CH2-O-D-O- group, in which D is C2-C10alkylene, C6-C15arylene;
C6-C12cycloalkylene, or, provided that G13 is not alkanoyl, alkenoyl or benzoyl, G14 can alternatively be 1-oxo-C2-C12alkylene, a divalent radical of an aliphatic, cycloaliphatic or aromatic dicarboxylic acid or dicarbamic acid or alternatively the group -CO-, G14, if n2 is 3, is a group , or, if n2 is 1, G13 and G14 together can be the divalent radical of an aliphatic, cycloaliphatic or aromatic 1,2- or 1,3-dicarboxylic acid.
G12, if n1 is 1, is C1-C18alkyl which is uninterrupted or interrupted by one or more oxygen atoms, cyanoethyl, benzoyl, glycidyl, a monovalent radical of an aliphatic, cycloaliphatic, unsaturated or aromatic carboxylic acid, carbamic acid or phosphorus-containing acid or a monovalent silyl radical, preferably a radical of an aliphatic carboxylic acid having 2 to 18 carbon atoms, of a cycloaliphatic carboxylic acid having 7 to 15 carbon atoms, or an .alpha.,.beta.-unsaturated carboxylic acid having 3 to 5 carbon atoms, where each carboxylic acid can be substituted in the aliphatic, cycloaliphatic or aromatic moiety, if present, by 1 to 3 -COOZ12 groups, in which Z12 is H, C1-C20alkyl, C3-C12alkenyl, C5-C7cycloalkyl, phenyl or benzyl, G12, if n1 is 2, is C2-C12alkylene, C4-C12alkenylene, xylylene, a divalent radical of an aliphatic, cycloaliphatic, araliphatic or aromatic dicarboxylic acid, dicarbamic acid or phosphorus-containing acid or a divalent silyl radical, preferably a radical of an aliphatic dicarboxylic acid having 2 to 36 carbon atoms, or a cycloaliphatic or aromatic dicarboxylic acid having 8-14 carbon atoms or of an aliphatic, cycloaliphatic or aromatic dicarbamic acid having 8-14 carbon atoms, where each dicarboxylic acid may be substituted in the aliphatic, cycloaliphatic or aromatic moiety by one or two -COOZ12 groups, G12, if n1 is 3, is a trivalent radical of an aliphatic, cycloaliphatic or aromatic tricarboxylic acid, which may be substituted in the aliphatic, cycloaliphatic or aromatic moiety by -COOZ12, of an aromatic tricarbamic acid or of a phosphorus-containing acid, or is a trivalent silyl radical, and G12, if n1 is 4, is a tetravalent radical of an aliphatic, cycloaliphatic or aromatic tetracarboxylic acid;
R1, R2, R3 and R4, independently of each other, are C1-C8alkyl or C1-C5hydroxyalkyl, or R1 and R2 together with the carbon atom they are attached to are C5-C12cycloalkyl, or R3 and R4 together with the carbon atom they are attached to are C5-C12cycloalkyl;
G is hydrogen or methyl;
G1 and G2, independently of one another, are hydrogen, methyl or together are a substituent =O; and G3 is a direct bond or methylene, open bonds of formulae (3) and (4) are linked to a carbon, nitrogen or oxygen atom of an organic residue as defined above, G13 is hydrogen, C1-C12alkyl, C2-C6hydroxyalkyl, C5-C7cycloalkyl, C7-C8aralkyl, C1-C18alkanoyl, C3-C5alkenoyl, benzoyl or a group of the formula (1b-1) n2 is the number 1, 2 or 3;
and G14, if n2 is 1, is hydrogen, C1-C18alkyl, C3-C8alkenyl, C5-C7cycloalkyl, C1-C4alkyl which is substituted by a hydroxyl, cyano, alkoxycarbonyl or carbamide group, glycidyl, a group of the formula -CH2-CH(OH)-Z or of the formula -CONH-Z, in which Z is hydrogen, methyl or phenyl;
G14, if n2 is 2, is C2-C12alkylene, C6-C12arylene, xylylene, a -CH2-CH(OH)-CH2 group or a -CH2-CH(OH)-CH2-O-D-O- group, in which D is C2-C10alkylene, C6-C15arylene;
C6-C12cycloalkylene, or, provided that G13 is not alkanoyl, alkenoyl or benzoyl, G14 can alternatively be 1-oxo-C2-C12alkylene, a divalent radical of an aliphatic, cycloaliphatic or aromatic dicarboxylic acid or dicarbamic acid or alternatively the group -CO-, G14, if n2 is 3, is a group , or, if n2 is 1, G13 and G14 together can be the divalent radical of an aliphatic, cycloaliphatic or aromatic 1,2- or 1,3-dicarboxylic acid.
15. Compound according to claim 12 of the formula IIIb in which the radicals A are independently of one another -OR13, -N(R14)(R15) or a group of the formula (IIId);
X is -O- or >N-R16;
R16 is hydrogen, C1-C18alkyl, C3-C18alkenyl, C5-C12cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl; C7-C9phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4alkyl; tetrahydrofurfuryl, a group of the formula (IIIf), or C2-C4alkyl which is substituted in the 2, 3 or 4 position by -OH, C1-C8alkoxy, di(C1-C4alkyl)amino or a group of the formula (Ie');
R11 has one of the definitions given for R16; and the radicals B have independently of one another one of the definitions given for A; and where formula (Ie') and all other symbols are as defined in claim 11 for formula Ia.
X is -O- or >N-R16;
R16 is hydrogen, C1-C18alkyl, C3-C18alkenyl, C5-C12cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl; C7-C9phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4alkyl; tetrahydrofurfuryl, a group of the formula (IIIf), or C2-C4alkyl which is substituted in the 2, 3 or 4 position by -OH, C1-C8alkoxy, di(C1-C4alkyl)amino or a group of the formula (Ie');
R11 has one of the definitions given for R16; and the radicals B have independently of one another one of the definitions given for A; and where formula (Ie') and all other symbols are as defined in claim 11 for formula Ia.
16. Use of a compound of formula Ia according to claim 11 and/or IIIc, IVa, Va according to claim 12 as stabilizer for organic material against degradation by light, oxygen and/or heat.
17. Process for stabilizing an organic material against degradation by light, oxygen and/or heat by applying a stabilizer to or incorporating a stabilizer into said material, characterized in that the stabilizer is a compound of the formula Ia according to claim 11 and/or IIIc, IVa or Va according to claim 12.
18. Use of a compound of formula IIIc or Va according to claim 12 as flame retardant for an organic polymer.
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| Application Number | Priority Date | Filing Date | Title |
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| CA2643170A CA2643170C (en) | 1998-02-25 | 1999-02-23 | Sterically hindered amine ethers as stabilizers against light, oxygen and/or heat |
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| ITMI98A000366 | 1998-02-25 | ||
| IT98MI000366A ITMI980366A1 (en) | 1998-02-25 | 1998-02-25 | PREPARATION OF STERICALLY PREVENTED AMINE ETHERS |
| US10471898A | 1998-06-25 | 1998-06-25 | |
| US09/104,718 | 1998-06-25 |
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| CA002262435A Expired - Lifetime CA2262435C (en) | 1998-02-25 | 1999-02-23 | Preparation of sterically hindered amine ethers |
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| JP (2) | JP4798815B2 (en) |
| KR (1) | KR100561146B1 (en) |
| CN (2) | CN100384826C (en) |
| AR (1) | AR015238A1 (en) |
| BE (1) | BE1014990A5 (en) |
| BR (1) | BR9900807B1 (en) |
| CA (2) | CA2643170C (en) |
| CZ (1) | CZ302752B6 (en) |
| DE (2) | DE19964603B4 (en) |
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| FR (1) | FR2777004B1 (en) |
| GB (1) | GB2334717B (en) |
| ID (1) | ID23225A (en) |
| MY (1) | MY123467A (en) |
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| US11001698B2 (en) | 2016-10-14 | 2021-05-11 | Basf Se | Stabilizer composition |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11001698B2 (en) | 2016-10-14 | 2021-05-11 | Basf Se | Stabilizer composition |
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| Publication number | Publication date |
|---|---|
| AR015238A1 (en) | 2001-04-18 |
| ES2159462A1 (en) | 2001-10-01 |
| CA2643170A1 (en) | 1999-08-25 |
| MY123467A (en) | 2006-05-31 |
| BR9900807A (en) | 2000-03-28 |
| CN1235159A (en) | 1999-11-17 |
| GB2334717A (en) | 1999-09-01 |
| KR100561146B1 (en) | 2006-03-15 |
| CA2643170C (en) | 2013-04-16 |
| NL1011394C2 (en) | 1999-10-26 |
| DE19964603B4 (en) | 2013-02-28 |
| JP4798815B2 (en) | 2011-10-19 |
| JPH11315067A (en) | 1999-11-16 |
| SG74700A1 (en) | 2000-08-22 |
| GB2334717B (en) | 2000-04-26 |
| RU2224758C2 (en) | 2004-02-27 |
| CZ302752B6 (en) | 2011-10-19 |
| GB9903463D0 (en) | 1999-04-07 |
| DE19907945A1 (en) | 1999-08-26 |
| DE19907945B4 (en) | 2013-06-06 |
| CN100384826C (en) | 2008-04-30 |
| KR19990072904A (en) | 1999-09-27 |
| BE1014990A5 (en) | 2004-08-03 |
| ID23225A (en) | 2000-03-30 |
| CN1552758A (en) | 2004-12-08 |
| ES2159462B1 (en) | 2002-05-01 |
| NL1011394A1 (en) | 1999-08-26 |
| BR9900807B1 (en) | 2013-06-11 |
| FR2777004B1 (en) | 2005-12-30 |
| CN1202085C (en) | 2005-05-18 |
| JP2011006443A (en) | 2011-01-13 |
| FR2777004A1 (en) | 1999-10-08 |
| CA2262435C (en) | 2009-12-22 |
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Effective date: 20190225 |