JPS6037094B2 - Method for stabilizing metal complexes and organic polymers, and method for producing metal complexes - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a metal key containing a sterically hindered amine and a monovalent anion, a method for producing the same, and its use as a stabilizer for synthetic polymers.

Various sterically hindered amines have been reported in recent years as stabilizers for synthetic polymers, and are described, for example, in the following patent specifications.

In the table below, GB-PS refers to British patent, US-PS
is a US patent, DT-OS is a German publication, JA-PS
represents a Japanese patent.

GB-PS1,325,774DT-OS2,321,
526GB-PS1,325,775DT-OS2,3
51,865US-PS3,853,890DT-OS
2,352,379GB-PS1,329,847DT
-OS2,352,658US-PS3,769,25
9DT-OS2,402,636DT-OS2,257
,997DT-OS2,415,8180S-PS3,
847,930DT-OS2,425,425DT-O
S2,258,086DT-OS2,427,853G
B-PS1,365,319DT-OS2,428,8
77DT-OS2, 258, 752DT-OS2, 43
5,170DT-OS2,319,816US-PS3
,536,722DT-OS2,337,822GB-
PS1, 202, 298DT-OS2, 337, 847
GB-PS1,202,299DT-OS2,337,
796US-PS3,547,874US-PS3,8
50,877US-PS3,542,729DT-OS
2,314,105US-PS3,639,409DT
-OS2,314,091US-PS3,640,92
8DT-OS2,314,115US-PS3,790
,525DT-OS2,315,042US-PS3,
862,155DT-OS2,315,245DT-O
S2,030,908DT-OS2,o4o,983U
S-PS3,829,404GB-PS1,262,2
34DT-OS2, 304, 374DT-OS2, o4
7,846DT-OS2,233,122DT-OS2
,o4o,975DT-OS2,327,717US-
PS3,84o,494DT-OS2,326,010
US-PS3,839,273DT-OS2,338,
076US-PS3,859,293DT-OS2,3
49,962JA-PS559,16oJA-OS49
-60337JA-PS591,467DT-OS2,
352,606JA-PS6oo,o42JA-OS4
9-63738JA-PS6oo, o43DT-OS2
,352,538JA-PS694,198DT-OS
2,353,5391A-PS64o,258DT-O
S2,258,368JA-pS64o,259JA-
OS49-72332JA-pS64o,26oJA-
OS49-77944JA-PS652,775JA-
OS48-65179JA-PS652,776DT-
OS2,425,984JA-PS72o,111DT
-OS2,433,639JA-PS659,579D
T-OS2,453,174DT-OS2,227,6
89DT-OS 2,418,540 Sterically hindered amines of this type stabilize polymers, such as polyolefins, such as polypropylene, against degradation by the action of ultraviolet radiation.

These may be used alone or together with other known stabilizers, for example antioxidants, UV inhibitors, light stabilizers, metal deactivators, phosphites, peroxides, as is customary in the stabilization of polymers. Oxide decomposer, polyamide stabilizer, basic C
2,2'-thiobis-[
4-(1,1,3,3-tetramethylbutyl)-phenol], bis[2-hydroxy-4-(1,1 , nickel complex of 3,3-tetramethylbutyl)-phenyl]-sulfone, 4-hydroxy-3
, 5-di-t-phthylbenzyl-phosphonic acid monoalkyl esters, such as the nickel salt of ethyl ester, as well as nickel-3,5-di-t-butyl 4-hydroxybenzoate (such as the above-mentioned DE 2,427,8
53). The present inventors have demonstrated that metal complexes containing sterically hindered amines and specific anions according to the invention exhibit a significantly better light-fastening effect in polymers than would be expected on the basis of the individual components. I saw it and put it out.

This advantageous property is accompanied by good prolongation of protective action in polymers and extraction stability and good compatibility, making the novel anchor compounds excellently suited for stabilizing polymers against UV degradation. has. When using the anions according to the invention, a synergistic effect with respect to the light-fastening effect occurs, ie the protective effect is greater than the sum of the effects of the individual components, but the known combinations of sterically hindered amines and the nickel complexes mentioned as state of the art; For example, sterically hindered amines and 2,2-thiobis[4-(1,1,3,3-tetramethyl-butyl)]
-phenol], nickel complex of bis[2-hydroxy-4-(1,1,3,3-tetramethylbutyl)-phenyl]-sulfone, or 4-hydroxy-3,5-di-t-butyl-penzylphosphonic acid The combination of monoethyl ester with a nickel collar does not exhibit such a synergistic effect (see Comparative Example). The stabilizers according to the invention were therefore not obvious from the current state of the art. The metal coin body according to the present invention has the following formula (1) [wherein Me represents magnesium, calcium, manganese, zinc, cobalt, nickel, chromium or aluminum, w represents 2 or 3, and p represents 1 or 2] where r represents 1 or 2, s represents a numerical value of 0 to 2, R,, R2, R3 and R4 each independently represent an alkyl group, Y represents hydrogen, an oxyl group or an alkyl group, X is the following group (wherein R'8 represents hydrogen or an alkyl group, R'9 represents a monovalent aliphatic or aromatic residue, and R', o are optionally substituted with a phenyl group) It's good to be done 2
R', . represents a monovalent aliphatic or aromatic residue, and R',2 represents an alkylene group which may be substituted with a hydroxyl group.

) represents a divalent residue that supplements the N-containing ring to become a 6-membered ring, and L represents a
a monovalent anion of aminophosphinic acid or aminophosphonic acid or a monovalent anion of formula (0): (wherein Z represents an oxo group or an alkylimy/group, and R5 represents an alkyl group, a substituted alkyl group, an aryl group or a substituted aryl group, R6 represents hydrogen or an alkyl group, or R5 and R6 together represent optionally substituted 1,4-butadiy-1,3-phenylene, and R
7 represents an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an alkoxy group or a substituted amino group.

) represents a monovalent anion of phenol. ]
It is expressed as Me is, as a metal ion with a divalent positive charge, in particular a divalent ion of magnesium, calcium and especially manganese, zinc, cobalt and especially nickel.

Me is a trivalently positively charged metal ion, in particular a chromium ion and especially an aluminum ion. In particular, p is 1.

R, , R2, R3 and R4 as alkyl radicals are each independently especially alkyl having 1 to 6 carbon atoms, preferably ethyl, especially methyl.

Y as an alkyl group is in particular alkyl of 1 to 8 carbon atoms, in particular alkyl of 1 to 4 carbon atoms, preferably hydrogen-substituted in the Q position, especially methyl.

A divalent residue X that replenishes the N-containing ring to become a 6-membered ring
is selected from the group:

■Sulfonyl group -S02-, ■Basis (R'6 is hydrogen or a Represents a rukyl group.

), ■ methylene group substituted with carboxyl group (R'9
represents a monovalent aliphatic or aromatic residue.

), ■ Cal esterified with methylene group substituted by boxyl group (R',.

represents a divalent aliphatic residue which may be substituted with an optionally substituted phenyl group, R,,R2,R3,
R4 and Y are as defined above. ), ■ group (R', . represents a monovalent aliphatic or aromatic residue).

), ■ base (R', 2 is replaced by a hydroxyl group. represents an alkylene group that may be

), and ■ groups (R,, R2, R3 and Y are as defined above.

). The monovalent anion L of the aliphatic carboxylic acid is especially R-
COO is the anion of a carboxylic acid in which the residue is an optionally substituted aliphatic hydrocarbon residue.

Optionally substituted aliphatic hydrocarbons are in particular alkyls having 1 to 2 carbon atoms, especially alkyls having 1 to 12 carbon atoms, cycloalkyls having 5 to 12 carbon atoms, especially 5 to 6 carbon atoms, Alkenyl having 2 to 23 carbon atoms, especially 2 to 12 carbon atoms, aralkyl having 7 to 1 carbon atoms, especially 7 to 12 carbon atoms (these may optionally be halogens, especially chlorine, hydroxyl, 1 to 6 carbon atoms) or alkoxy of 1 to 6 carbon atoms), e.g. methyl, ethyl, n
-hexyl, n-undecyl, 1-ethyl-n-pentyl, cyclohexyl, vinyl, benzyl, chlorobenzyl, hydroxybenzyl, methyl besodyl and methoxybenzyl. The monovalent anion L of the aliphatic carbosic acid is an anion of the aliphatic Q- or 8-aminocarboxylic acid,
In particular, those having 2 to 2M carbon atoms, especially those having 2 to 12 carbon atoms,
the amino group is unsubstituted, preferably the amino group is branched or straight-chain, having 1 to 12 carbon atoms,
Examples of Q-aminocarboxylic acids which are anions of aliphatic Q-1- or 8-aminocarboxylic acids which are mono- or dialkylated, especially with 1 to 8 alkyls, are glycine, Q-alanine, valine and isoleucine; is substituted in particular by one or two n-alkyl groups having 1 to 8 carbon atoms, such as di-n-octylglycine.

Examples of 8-amino acids include those in which the amino group has 1 to 8 carbon atoms.
8-alanine substituted with one or two n-alkyls, such as di-n-bropyl-6-alanine.

The monovalent anion L of aminophosphinic acid or aminophosphonic acid has, in particular, the following formula (la): [wherein R, .
a and R2,a each independently represent hydrogen, alkyl, aralkyl, aryl or aryl or aralkyl substituted with chlorine and/or an alkyl group and/or an alkoxy group, or R, . a and R2,a together form a cycloalkane ring with the carbon atom to which they are bonded; and/or represents an aralkyl group substituted with an alkyl and/or alkoxy group, and the substituents R, . If neither a nor R is an aromatic group, or only one is an aromatic group, then R3, a
or R4,a may be an aryl or an aryl group substituted with chlorine and/or an alkyl group and/or an alkoxy group, or R3,a and R may be combined with the nitrogen atom to which they are bonded. forming a saturated heterocyclic ring, R
5, a represents alkyl, cycloalkyl, aralkyl, aryl, alkoxy, cycloalkoxy, aralkoxy or aryloxy, the aromatic group being substituted with chlorine and/or an alkyl group and/or an alkoxy group; You can.

] If RI・a, R2・a, R, R4,a or R5,a is alkyl, this means linear or branched alkyl,
For example, methyl, ethyl, propyl, isopropyl, n-
It may be butyl, n-hexyl, n-octyl, 2-ethylhexyl, n-dodecyl or n-octadecyl.

If R3,a and R4,a represent alkoxyalkyl, this may be, for example, 2-methoxyethyl or 3-methoxypropyl. When these substituents are aralkyl or substituted aralkyl, they are, for example, penzyl, 4-methylbenzyl, 4-isopropylbenzyl, 3-chlorobenzyl, 4-methoxybenzyl, 2,4
-dichlorobenzyl, 2-chloro-4-methylbenzyl, 1- or 2-naphthylmethyl, phenylethyl or 2-dichlorobenzyl
- may be naphthyl ethyl. In the definition of aryl or substituted aryl, these are, for example, phenyl, diphenylyl, naphthyl, 4-methylphenyl, 3-chlorophenyl, 3,4-dichlorophenyl, 4-methoxynaphthyl-1,4-butoxyphenyl, 3-chloro-4-methylphenyl. or 3-ethoxyphenyl. R,.
a and R2. If a together with the carbon atoms to which they are attached form a cycloalkane ring, this may be, for example, a cyclobentane, cyclohexane or 4-methylcyclohexane ring. R3,a, R4,a or R5,a
If represents cycloalkyl, this may be, for example, cyclobentyl, cyclohexyl or 3-methylcyclohexyl.

When R and R4,a together with the N atom to which they are bonded represent a heterocyclic ring, this means, for example, a pyrrolidine moiety, a methylpyrrolidine moiety, a dimethylpyrrolidine ring, a piperidine moiety, a morpholine ring, an N-methylpyrrolidine moiety. It may be a verazine ring or a N-ethylpiverazine ring. When R58 represents an alkoxy group or a cycloalkoxy group, these may be methoxy, ethoxy, isopropoxy, butoxy, hexoxy, 2-ethylhexoxy or cyclohexoxy. The R arc representing aralkoxy or substituted aralkoxy is, for example, a benzoxy group, 4
-chlorobenzoxy, 2,4-dichlorobenzoxy, 3-methylbenzoxy or 2-phenylethoxy. R5. represents aryloxy or substituted aryloxy. a can be, for example, a phenoxy group, p-tolyloxy group, 4-chlorophenoxy group, 8-naphthoxy group, 3-methoxyphenoxy group or 3-chloro-4-methylphenoxy group (German Application No. 2,
443,40 P). formula (la)
In,R,. a and R each independently represent hydrogen, alkyl having 1 to 12 carbon atoms, or 7 to 1 carbon atoms;
1 aralkyl or aryl having 6 to 12 carbon atoms, the aromatic ring being one or two chlorine and/or methyl and/or alkoxy groups having 1 to 8 carbon atoms; May be substituted or R, . a and R2
・a forms a cyclobentane ring or cyclohexane ring with the carbon atom to which they are bonded, and R3,a and R4,a each independently represent an alkyl group having 1 to 12 carbon atoms, 5 carbon atoms, or 6 cycloalkyl or an aralkyl group having 7 to 1 carbon atoms; this aralkyl is 1 or 2 chlorine and/or methyl and/or alkoxy groups having 1 to 8 carbon atoms; may be substituted, or the substituents R, . If neither a nor R2,a represents an aromatic group, or only one of them represents an aromatic group, R3,a and R4,a may represent an aryl group, which may represent chlorine and ( or) may be substituted with one or two alkyl groups having 1 to 4 carbon atoms and (or) alkoxy groups having 1 to 8 carbon atoms, or R3,a and R4,a are substituted with Combined N
Together with the atoms, they form a pyrrolidine, piveridiso, piperazine or morpholine heterocyclic ring, and R5,a is alkyl having 1 to 8 carbon atoms, cycloalkyl having 5 or 6 carbon atoms, carbon represents aralkyl having 7 to 1 atoms or aryl having 6 to 12 carbon atoms, the aromatic ring being chlorine and/or a methyl group and/or an alkoxy group having 1 to 8 carbon atoms; Phenoxy which may be substituted one or two times, or R5, a is substituted one or two times with an alkoxy group having 1 to 8 carbon atoms, a cyclohexyl group, a benzoxy group, a phenoxy group, or a chlorine or methyl group. Preference is given to anions of the formula (la) which represent groups.

Furthermore, in formula (la), R, . a and R2・a are
each independently hydrogen, alkyl having 1 to 8 carbon atoms,
benzyl or CH3- or <represents a phenyl group substituted with CH30-, or R, . a and R2,a are
These form a cyclohexane ring together with the carbon atoms to which they are bonded, and R3M and R4,a each independently represent hydrogen, alkyl having 1 to 8 carbon atoms, cyclohexyl, or aralkyl having 7 to 11 carbon atoms. The aralkyl may be substituted with one methyl, chlorine or alkoxy group having 1 to 4 carbon atoms, or the substituent R
、． When neither a nor R2,a represents an aromatic group, or only one thereof represents an aromatic group, R3,
Also represents a phenyl group in which a or R cape may be substituted with chlorine and/or an alkyl group having 1 to 4 carbon atoms and/or an alkoxy group having 1 to 5 carbon atoms. or R3,a and R4,a together with the N atom to which they are bonded form a pyrrolidine ring, piverizine ring or morpholine ring, and R58 is alkyl having 1 to 8 carbon atoms, cyclohexyl, or Aralkyl group having 7 to 11 atoms, aryl group having 6 to 10 carbon atoms (C
Anions of the formula (la) which represent an alkoxy group having 1 to 4 carbon atoms, a benzoxy group, a phenoxy group, a chlorophenoxy group or a tolyloxy group are preferred. It is.

In formula (la), R, . a is hydrogen, number of carbon atoms is 1~
6 alkyl, phenyl or 4-methoxyphenyl, R represents hydrogen or methyl, R3, a is hydrogen, alkyl having 2 to 8 carbon atoms, cyclohexyl,
Represents benzyl or 4-methoxybenzyl, R4,a
represents hydrogen, alkyl having 2 to 8 carbon atoms, cyclohexyl, phenyl, 4-methoxyphenyl, 2-methoxy5-t-butylphenyl, or R3, a and R48 together with the nitrogen atom are a piverdine group or a morpholine group Particular preference is given to the anion (la) in which R represents C1-4 alkyl, phenyl, 4-tolyl, 4-methoxyphenyl or C1-4 alkoxy.

Examples of anions of formula (la) are listed below: la. 1(
C2 day 5) 2N-CH2-p (=o) (1 oe). C2
Day 5la. 2nd day 2N-CH (C6 public)-p (=○) (1○e).

C2 day 5la. 3C4day9NH-CH(C6鴇)-P(
=○) (10e) OC3rd 7la. 4C6 days 5NH-C
H(C3day 7)-P(=○)(10e)OCH3la.
5(C44)2H-C(CH3)2-P(=○)(1o
e) OC3H? la. 6CH3(CH2)3CH(C2
Day 5) -CH2-NH-CH(4-CH30-cyclohexyl)-P(=0)(-oe)oc2 Day 5 1a. 7pyrrolidino-CH2P (:○) (1○e).

C4 day 9la. 8n-C4&NH-CH(4-CH3-
cyclohexyl) 1P (=○) (1.

e) P-(CH3〇1 phenyl) 1a. 9 piberidino CH21P(=○)(1○e)n
C4 day 9la. 10(n-C4day9)2N-CH(CH
3)-P(=.

) (1 oe) OC 2nd 51a. 11 (n-C4)3N
-C(CH3)(C3day7)-P(=0)(1oe)o
c2 day 51a. 12n-C4 day H-CH (C6 day 5)
-P (=○) (1○e) C6 is la. 13 (C2 day 5)
2N-C Koichi p (=○) (-.

e) The C6 extended imino group Z has, in particular, no carbon atoms, and 1 carbon atom.
2, especially 1 to 6 alkyls as substituents.

The substituted imino group is further one N=C(R7)-C(R6)=C
(〇e) It may also be an alkylimino group substituted by R5, the alkyl having especially 1 to 6, especially 2 carbon atoms, the substituent being particularly present in the 2-position, and R5 ,R6
and R7 particularly represent the following: Alkyl R5,R
6 and R7 preferably have 1 to 12, especially 1 to 6 carbon atoms and are, for example, methyl, ethyl or n-propyl.

Arralkyl R5 and R7 are especially those having 7 to 12 carbon atoms, such as penzyl or phenethyl.

Aryl R5 and R7 is in particular cycloaliphatic or heterocyclic aryl having 4 to 10 carbon atoms, such as phenyl or alkyl having 1 to 12 carbon atoms, especially 1 to 6 carbon atoms, such as methyl, carbon atom Phenyl substituted by a number of 1 to 12, especially 1 to 6, alkoxy or halogens, such as chlorine or, for example, chenyl.

Optionally substituted 1,4-butadi-1,3-enylene R50R6 is in particular unsubstituted or substituted with alkyl having 1 to 12 carbon atoms, especially 1 to 6 carbon atoms, such as methyl, Alkoxy having 1 to 12 carbon atoms, especially 1 to 8 carbon atoms, such as n-octyloxy, or halogen, such as chlorine.

Optionally substituted alkyl R7 is in particular alkyl having 1 to 12 carbon atoms, in particular 1 to 6 carbon atoms, which carries a halogen, such as fluorine or chlorine, as a substituent, such as trifluoromethyl.

Alkoxy R7 has especially 1 to 12 carbon atoms, especially 1
~6 alkoxy, such as methoxy or ethoxy.

Amino R7, which may have been imitated in some cases, may have 1 carbon atom.
~12 alkylaminos, such as methylamino, dialkylaminos having 2 to 24 carbon atoms/and especially undiluted anilinos, or 1 to 6 carbon atoms as substituents in the p-, m- or o-positions anilino with alkyl, such as methyl, or especially C1-C6 alkoxy, such as methoxy.

As L, in formula (1), Z represents oxo or imi/, R5 represents alkyl, R6 represents hydrogen, or R5 and R6 together represent 1,4-butadi-1,3
- henylene and R7 represents alkoxy (1
), especially when Z represents oxo, R5 represents alkyl, R6 represents hydrogen, and R7
Preference is given to monovalent anions in which represents alkoxy.

It is likewise advantageous for R7 to be alkyl, especially methyl, or phenyl. Preference is given to metal complexes of the following formula (rainbow);
alkenyl, alkynyl, aralkyl, hydroxyalkyl, alkoxyalkyl, aliphatic or aromatic acyloxyalkyl, cyanoalkyl, halogenalkyl,
represents epoxyalkyl or alkoxycarbonylalkyl, R, . represents hydrogen or methyl].

Alkyl R8 and R9 preferably has 1 to 12, especially 1 to 6 carbon atoms, for example methyl.

Alkenyl R8 and R9 are especially 2 to 12, especially 2 to 12
It has a number of carbon atoms of 6 and is, for example, aryl. Alkyl R8 and R9 have 2 to 12, especially 2 to 6 carbon atoms, for example propargyl. Aralkyl R8
and R9 in particular has 7 to 12 carbon atoms, optionally in particular alkyl of 1 to 12 carbon atoms, especially 1 to 6 carbon atoms, alkoxy of 1 to 12 carbon atoms, especially 1 to 6 carbon atoms,
or substituted with a halogen, such as chlorine or pendyl. Hydroxyalkyl R8 and R9 preferably has 1 to 12, especially 1 to 6 carbon atoms, for example 2-hydroxyethyl. Alkoxyalkyl R8 and R9 preferably has 2 to 12, especially 2 to 6 carbon atoms, for example 2-methoxyethyl. Aliphatic acyloxyalkyl R8 and R9 have a total of preferably 2 to 18, especially 2 to 12 carbon atoms. Aromatic acyloxyalkyl R8
and R9 have a total of 7 to 18, especially 7 to 12 carbon atoms. Cyanoalkyl R8 and R9 are especially 2-12
, especially 2 to 6 carbon atoms, for example cyanomethyl. Halogenalkyl R8 and R9 are especially 1-1
It has 2, especially 1 to 6 carbon atoms, and halogen is especially chlorine, for example 2-chloroethyl. Epoxyalkyl R8 and R9 are especially 2 to 12, especially 2 to 6
carbon atoms, for example 2,3-epoxypropyl. Alkoxycarbonylalkyl R8 and R9 have a total of 3 to 18, especially 3 to 12 carbon atoms.
For example, 2,2',6,6-tetraethyl-4,4-dihydroxy-2,2',3,3,',6,6-hexamethyl-4,4'-bipiveridine and 2,2,2',2,6
,6,6,6'-octamethyl-4,4,-dihydroxy-4,4-bipiveridine, R8 and R
Advantageously, 9 are identical and represent hydrogen or alkyl, especially methyl.

Preference is also given to metal anchor bodies of the formula (N): in which Me, p, r, s and L are as indicated above, q'' is 1 or 2, and R, 2 are represents alkyl, R. 3 represents alkyl, R, 4 represents alkyl "phenyl or aralkyl, or R, 3 and R, 4 together represent alkylene, R, 5
represents hydrogen, alkyl or allyl, R, 6 is hydrogen,
Represents oxyl, alkyl, alkenyl, aralkyl, eboxyalkyl, 2-hydroxyethyl, 2-alkoxyethyl, 2-aryloxyethyl, 2-aralkoxyethyl or 2-acyloxyethyl, R, 7
represents hydrogen, alkyl or alkenyl, R,8 is
When n is 1, hydrogen, alkyl, alkenyl, aralkyl, aryl, cycloalkyl, epoxyalkyl, alkoxyalkyl, phenoxyalkyl, alkoxycarbonylmethyl, phenoxycarbonylmethyl,
represents hydroxyalkyl, acyloxyalkyl, 2-hydroxyphenethyl, 2-alkoxyphenethyl, 2-aryloxyphenethyl, 2-aralkoxyphenethyl or 2-acyloxyphenethyl, or R
, 8 is alkylene, oxaalkylene, when n is 2,
alkenylene, arylene alkylene, arylene,
Oxydiphenylene, methylene diphenylene, alkylene di(oxycarbonylalkylene), alkylene di(carbonyloxyalkylene), alkylene diphenylene (carbonyloxyalkylene), thiaalkylene di(carbonyloxyalkylene), thiaalkylene di - (carbonyloxyalkylene), alkenylene (carbonyloxyalkylene), alkenylene (carbonyloxyalkylene),
Phenylene Di(carbonyloxyalkylene), Phenylene Di(carbonyloxyalkylene, 1
,4-sik.

Hexylene-di-(carbonyloxyalkylene) or 1,4-cyclohexylene-di(carbonyloxyalkylene)]. Alkyl R,2,R,3
, R,4, R,5, R,6, R,7 and R,8 each independently have 1 to 12, especially 1 to 8 carbon atoms, such as ethyl, n-propyl and especially methyl. Aralkyl RMR,6 and R,8 each independently preferably have 7 to 12 carbon atoms, such as phenethyl and especially penzyl. Alkylene R,30R,4 preferably has 4 to 12, especially 5 carbon atoms and is, for example, pentamethylene. alkenyl R,6,R. 7 and R. 8 is each independently particularly 2 to 12, especially 2 to 6
carbon atoms, for example allyl or methallyl. Epoxyalkyl R,6 and R,8 each independently have 2 to 12, especially 3 to 6 carbon atoms and are, for example, 2,3-epoxypropyl. 2-Alkoxyethyl R,6 has especially 1 to 12, especially 1 to 6 carbon atoms in the alkoxy moiety, for example 2-methoxyethyl.

2-aryloxyethyl R,6 is in the aryl moiety,
Especially with 6 to 12, especially 6 carbon atoms, e.g. 2
-Phenoxycetil.

2-Alkoxyethyl R,6 especially has 7 to 12 carbon atoms in the aralkoxy moiety, for example 2-penzyloxyethyl.

2-Acyloxyethyl R,6 preferably has 1 to 20, especially 2 to 8 carbon atoms in the acyloxy moiety and is, for example, alkanoyloxy, such as 2-acetoxyethyl.

Aryl R,8 especially has 6 to 12 carbon atoms, for example phenyl, which in particular has 1 to 12 carbon atoms, especially 1 to 6 alkyl, 1 to 12 carbon atoms, especially It may be substituted with 1 to 6 alkoxy or halogens, such as chlorine. Cycloalkyl R,8 is especially 5-
It has 12, especially 5 to 6 carbon atoms, for example cyclohexyl. Alkoxyalkyl R,8 is especially 2
~18, especially 2 to 12 carbon atoms, for example methoxymethyl or 2-methoxyethyl. Phenoxyalkyl R,8 preferably has 7 to 18, especially 7 to 12 carbon atoms, for example 2-phenoxyethyl.
Alkoxycarbonylmethyl R,8 is especially 3-2 hard,
In particular it has 3 to 9 carbon atoms, for example methoxycarbonylmethyl. Hydroxyalkyl R,8 especially has 1 to 12, especially 1 to 6 carbon atoms, for example 2
-Hydroxyethyl. Acyloxyalkyl R,
8 preferably has 1 to 2 carbon atoms, especially 2 to 18 carbon atoms, for example alkanoyloxyalkyl, such as 2-acetoxyethyl. 2-alkoxyphenethyl R,8
has especially 1 to 12, especially 1 to 6 carbon atoms in the alkoxy moiety.

2-Aryloxyphenethyl R,8 has especially 6 to 12, especially 6 carbon atoms in the aryl part.

2-Aralkoxyphenethyl R,8 has especially 7 to 12, especially 7 carbon atoms in the aralkoxy moiety.

2-Acyloxyphenethyl R,8 has especially 1 to 2, especially 2 to 12 carbon atoms in the acyloxy moiety, for example alkanoyloxy.

Alkylene R,8 preferably has 1 to 2 carbon atoms, especially 1 to 8 carbon atoms, for example methylene, ethylene, 1'3-
Propylene, 1,4-butylene or 1,8-octylene. Oxaalkylene R,8 is especially 2 to 2 solids,
In particular it has 2 to 10 carbon atoms, for example 3-oxabentamethylene. Alkenylene R,8 is especially 2-
2 hard carbon atoms, especially 2 to IM hard carbon atoms, for example 1,
It is 4-buty-2-enylene. Arylene dialkylene R,8 preferably has a total of 8 to 2 carbon atoms, especially 8 to 14 carbon atoms, for example phenylene dimethylene. aryreso R,8 especially has 6 to 12 carbon atoms,
For example, phenylene. Alkylene (oxycarbonylalkylene) R,8 is especially a total of 5 to 2 rivers,
In particular, it has 5 to 12 carbon atoms, for example alkylene di(oxycarbonylmethylene), such as 3,6-dioxor-2,7-dioxooctamethylene. Alkylene di(carbonyloxyalkylene) R,8 has a total of preferably 5 to 2 carbon atoms, especially 7 to 14 carbon atoms, such as alkylene di(carbonyloxyethylene), for example 3,8-dioxar 4,7 - dioxadecamethylene. Alkylene-di(carbonyloxy-alalkylene) R,8 has a total number of carbon atoms in the alkylene moiety from 1 to 8, and the aralkylene moiety is particularly a phenyl group in which the free valence of R,8 originates from the 8-carbon atom. tyrene, such as 2,9-diphenyl-3,8
-dioxa-4,7-dioxo-decamethylene.
thiaalkylene di(carbonyloxyalkylene) R,8 has especially 2 to 1 carbon atoms, especially 2 to 6 carbon atoms in the thiaalkylene moiety and 2 carbon atoms in the alkylene moiety , for example 3,11-dioxa-4,10
-dioxo-7-thiatridecamethylene. Thialkyl range (thialkyloxyalkylene)
R,8 has especially 2 to 10, especially 2 to 6 carbon atoms in the thiaalkylene moiety; the aralkylene moiety has R,
Phenylethylene in which the free valence of 8 originates from the 8-C atom, such as 2,12-diphenyl-3,11-dioxor-4,10-dioxo-7-thiatridecamethylene. Alkenylene di-(carbonyloxyalkylene) R,8 is particularly 2 to 1 in the alkenylene moiety.
It has 2, especially 4 to 1 hard carbon atoms, and the alkylene moiety is especially ethylene, for example 3,10-dioxo-4,9-dioxo-6,7-dehydrododecamethylene. Alkenyresodi-(carbonyloxyalalkylene)R. 8 is particularly 2 to 12 in the alkenylene moiety
, in particular 4 to 1 hard carbon atoms, the aralkylene moiety is in particular phenylethylene in which the free valence of R,8 originates from the 81 C atom, for example 2,11-diphenyl 3,10-dioxor 4,9-dioxo-6,7
-dehydrodedecamethylene. Phoenix range
(Carbonyloxyalkylene) R,8 especially has 2 carbon atoms in the alkylene moiety, for example phenylene di-(carbonyloxyethylene). 1,4-cyclohexylene (carbonyloxyalkylene)
R,8 especially has 2 carbon atoms in the alkylene moiety, for example 1,4-cyclohexylene.

1,4-cyclohexylene-di(carbonyloxyalalkylene) R,8 has as aralkylene, in particular phenylethylene, in which the free valence of R,8 emanates from the 31 C atom.

R,2, R,3 and R,4 are each methyl or ethyl, R,5 is hydrogen or methyl, R,6 is hydrogen, oxyl or methyl, R,7 is hydrogen, n
is 1, R, 8 is hydrogen, alkyl having 1 to 8 carbon atoms, allyl, benzyl, 2,3-epoxypropyl, 2-alkano having 2 to 18 carbon atoms in the alkanoyloxy moiety 2-(alkyloxy)*-ethyl, 2-benzoyloxy-ethyl, 2-(alkylbenzoyloxy)-ethyl having 1 to 4 carbon atoms in the alkyl moiety or 2-(3,5-di-t-butyl-4- hydroxyphenethyloxy)-ethyl, and when n is 2, 7
,9-diethyl-6,7,9-trimethyl-1,3,8
- from 2 to 6 carbon atoms, as in triazaspiro[4,5]decane-2,4-dione or 7,7,9,9-tetramethyl-1,3,8 triazaspiro[4,5]decane-2,4-dione. Advantageously, it is p-phenylene dimethylene or p-phenylene dimethylene.

R,2 and R,3 are -C ratio -R',2 and R,5 is R',3, then all R',3 are the same and are hydrogen or methyl; , 4 is methyl,
Particularly advantageous. Metallic bodies of the formula (V) are also advantageous;
In the formula, Me, p, r, s and L represent those mentioned above, R, 9 and R2o each independently represent a hydrogen atom, alkyl, alkenyl, alkynyl or aralkyl, and R2 and R22 each represent independently represents alkyl, R23 represents alkyl, R24 represents alkyl, phenyl, aralkyl, or a 5- or 6-membered tetraherocyclic group containing 0, S or N;
23 and R24 together represent alkylene or optionally substituted 3-azabentamethylene, R25 is hydrogen, oxyl, alkyl, alkenyl, alkoxyalkyl, aralkyl, epoxyalkyl, alkoxycarbonylmethyl, alkenyloxycarbonylmethyl,
Represents phenoxycarbonylmethyl, aralkoxycarbonylmethyl, cycloalkyloxycarbonylmethyl, hydroxyalkyl or acyloxyalkyl,
q'' represents 1, 2, 3 or 4, R26 is hydrogen, 1-
represents a trivalent optionally substituted hydrocarbon residue or a mono- to tetravalent acid residue derived from an organic or inorganic acid by elimination of at least one hydroxyl group].

The monovalent optionally substituted hydrocarbon residue R26 is
In particular alkyl, alkenyl, aralkyl, cycloalkyl, 2-alkoxycarbonyl-vinyl, 2-alkoxycarbonyl-1-methylvinyl or 2-alkoxycarbonyl-1-phenylvinyl.

The divalent optionally substituted hydrocarbon residue R26 is
In particular alkylene, alkenylene or phenylene dimethylene.

The trivalent optionally substituted hydrocarbon residue R26 is
Especially s-triazine-2,4,6-tolyl.

Monovalent radicals R26 of organic or inorganic acids are in particular monovalent radicals of aliphatic, araliphatic, cycloaliphatic, aromatic or heterocyclic carboxylic acids, monovalent radicals of S monovalent acids, such as aliphatic or monovalent groups of aromatic sulfonic acids, monovalent groups of P-containing acids such as optionally substituted phosphoric acids, phosphonic acids or phosphorous acids,
or an optionally substituted carbamoyl group.

A monovalent group R26 of an organic or inorganic acid is in particular a divalent group of an aliphatic, aromatic, alicyclic or heterocyclic dicarboxylic acid,
Carbonyl, sulfinyl, sulfonyl, residues of P-containing acids, such as >P, >P-alkyl, >P-aryl, >P-aralkyl or -P(OC ratio)2C(CH
20) 2P-, alkylene-di-aminocarbonyl, arylene-di-aminocarbonyl, phenylene-di-methyleneaminocarbonyl, Siku.

hexylene diaminocarbonyl, oxydi(phenylene aminocarbonyl), methylene diphenylene diaminocarbonyl), biphenylylene diaminocarbonyl, dimethylbiphenylene diaminocarbonyl, methylene di(1,4-cyclohexyl) silene-aminocarbonyl) or 1,4-cyclohexylene-di-(methylesoaminocarbonyl). The trivalent group R26 of the organic or inorganic acid is in particular the trivalent group of benzenetricarboxylic acid, >P-, >P(=○)- or >B-, and the tetravalent group of the acid is especially benzenetricarboxylic acid. It is a tetravalent group of tetracarboxylic acid or >Si<.

Alkyl R,9,R2.

, R2, , R22, R numbers, R24, R25 and R26 preferably have 1 to 12, especially 1 to 6 carbon atoms, such as ethyl, n-propyl and especially methyl. Alkenyl R,9, R27, R25 and R26 are especially 2-12
, especially 3 to 4 carbon atoms, for example allyl or metaallyl. Alkynyl R,9 and R2o especially has 3 to 4 carbon atoms and is, for example, propargyl. Aralkyl R, 9, R2o, R24, R25 and R-Sat in particular has 7 to 18, especially 7 to 12 carbon atoms and is preferably optionally substituted penzyl or phenethyl, with the phenyl moiety In particular, the substituent has a carbon atom number of 1
to 12, especially 1 to 6 alkyl, such as methyl, alkoxy, such as methoxy, having 1 to 12, especially 1 to 6 carbon atoms, or halogen, such as chlorine. ○、S
or a 5- or 6-membered heterocyclic group R24 containing N is especially pyridyl, such as 2-, 3- or 4-pyridyl, 2-
Furyl or 2-thienyl. Alkylene R230R
24 especially has 4 to 6 carbon atoms and is especially pentamethylene. Optionally substituted 3-aza-pentamethylene R23+R24 is a substituent in which in the 11-position and/or in the 5-position there is optionally alkyl having 1 to 6 carbon atoms, such as methyl, in the 21-position and in the 4-position. 2 alkyls in each position, e.g. methyl and/or ethyl, R2 in the 3-position
a group corresponding to 5, especially oxyl, or with 1 to 6 carbon atoms
alkyl, e.g. methyl, or 3-azabentamethylene is unsubstituted in the 3-position, e.g. 2,
2,4,4-tetramethylene-3-azabentamethylene, 2,2,3,4,4-bentamethyl-3-azabentamethylene, or 1,2,4-trimethyl-2,4-jethyl-3-azabentamethylene. Alkoxyalkyl R25 typically has 2 to 12, especially 3 to 6 carbon atoms and is, for example, 2-methoxyethyl. Epoxyalkyl Rpuma especially has 2 to 12, especially 2 to 6 carbon atoms, for example 2,3-epoxypropyl.
Alkoxycarbonylmethyl R25 has especially 1 to 12, especially 1 to 6 carbon atoms in the alkoxy moiety, for example methoxycarbonylmethyl. Alkenyloxycarbonylmethyl
12, in particular 3 to 6 carbon atoms, for example AIJ
is carbonylmethyl. Aral,koxycarbonylmethyl R25 has especially 7 to 12 carbon atoms in the aralkoxy moiety, for example penzyloxycarbonylmethyl. Cycloalkoxycarbonylmethyl, in which the cycloalkoxy moiety preferably has 5 to 12, especially 6 carbon atoms, is, for example, cyclohexyloxycarbonylmethyl. Hydroxyalkyl R25 is
It preferably has 1 to 12, especially 1 to 6 carbon atoms, for example 2-hydroxyethyl. Acyloxyalkyl R25 has especially 1 to 12, especially 1 to 6 carbon atoms in the alkyl moiety, in particular 1 to 18, especially 2 to 12 carbon atoms in the acyl moiety, e.g. -acetoxyethyl. Especially 5 to 12 cycloalkyl R26,
In particular it has 5 to 6 carbon atoms, for example cyclohexyl. 2-Alkoxycarbonylvinyl R26 preferably has 1 to 12, especially 1 to 6 carbon atoms in the alkoxy moiety, for example 2-methoxycarbonylvinyl.

2-Alkoxycarbonyl-1-methyl-vinyl R26
has especially 1 to 12, especially 1 to 6 carbon atoms in the alkoxy moiety, for example 2-methoxycarbonyl-1-methyl-vinyl.

2-alkoxycarponyl-1-phenyl-vinyl R2
6 has especially 1 to 12, especially 1 to 6 carbon atoms in the alkoxy moiety, for example 2-methoxycarbonyl-1
- Phenylruvinyl.

Alkylene has especially 1 to 18, especially 1 to 12 carbon atoms, such as especially straight-chain C1-C8 alkylene, such as 1,2-ethylene, 1,3-propylene or It is 1,4-butylene. Alkenylene R26
has especially 2 to 18, especially 2 to 12 carbon atoms,
For example, especially straight-chain alkenylene, such as 1,4-phthalene,
It is 2-phenylene. Monovalent valence R2 of aliphatic carboxylic acid
6 is in particular the residue of an alkanecarboxylic acid having 1 to 22 carbon atoms, in particular 1 to 18 carbon atoms, such as acetic acid, propionic acid or acetic acid. Monovalent group R26 of aromatic aliphatic carboxylic acid
has especially 8 to 2 carbon atoms, especially 8 to 12 carbon atoms,
For example, the residue of phenylacetic acid or 8-phenylpropionic acid. The monovalent base 26 of the cycloaliphatic carboxylic acid preferably has 6 to 14, especially 6 to 9 carbon atoms and is, for example, the residue of cyclohexanecarboxylic acid. The monovalent group R26 of the aromatic carboxylic acid is particularly 7 to 18, especially 4 to 13
carbon atoms, such as penzoyl, which optionally has 1 to 12 carbon atoms, especially 1 to 6 alkyls, such as methyl, 1 to 12 carbon atoms, especially 1 to 6 carbon atoms;
substituted with 6 alkoxy, e.g. methoxy, halogen, e.g. chlorine and/or hydroxyl, e.g. 4-
Hydroxy-3,5-dialkyl-penzoyl, such as 4-hydroxy-3,5-di-tert-butylbenzoyl. The monovalent radical R26 of the heterocyclic carboxylic acid is in particular the residue of pyridinecarboxylic acid, furocarboxylic acid or thiophenecarboxylic acid. Aliphatic sulfonic acid residue R
The spheres preferably have 1 to 20, especially 1 to 6 carbon atoms,
For example, the residue of an alkanesulfonic acid, such as methanesulfonic acid. The aromatic sulfonic acid residue R26 is particularly 6-
residues of benzenesulfonic acid or naphthalenesulfonic acid having 2 carbon atoms, in particular 6 to 12 carbon atoms, e.g. alkyl, such as methyl, alkoxy having 1 to 12 carbon atoms, especially 1 to 6 carbon atoms, such as methoxy, or halogen, such as chlorine or bromine), and P-containing acids which are the residues of p-toluenesulfonic acid. monovalent group R of
26 is especially (ethylenedioxy)P-, 1P(OCH
2) 2C(CH3)2 or -P(=○)(OC2&)C
It is H2C6&. Optionally substituted carbamoyl R26 in particular has 1 to 20 carbon atoms, for example carbamoyl, N-mono- or N-disubstituted carbamoyl (
Substituents are in particular alkyl having 1 to 18 carbon atoms, in particular 1 to 4 carbon atoms, such as methyl or ethyl, especially 7 to 18 carbon atoms.
8 aralkyl, such as penzyl or phenethyl,
In particular aryl of 6 to 12 carbon atoms, such as unsubstituted phenyl or substituted with halogen, such as chlorine, in particular phenyl substituted with alkyl of 1 to 4 carbon atoms, such as methyl, cycloalkyl, eg cyclohexyl), or the two substituents together with the N atom to which they are attached form a piberidino, pyrrolidino or morpholino. Preference is given to N-monosubstituted carbamoyl. Divalent radicals R26 of aliphatic or cycloaliphatic carboxylic acids preferably have 2 to 2, in particular 2 to 10, for example alkylene dicarbonyl, such as oxalyl, malonyl, ethylene dicarbonyl, tetramethylene dicarbonyl. , hexamethylene dicarboxylic acid, octamethylene dicarbonyl or decamethylene dicarbonyl or especially thiaalkylene dicarbonyl having 4 to 12 carbon atoms, such as 3-thiabentamethylene dicarbonyl, or especially 4 to 12 carbon atoms, especially 4 to 6 alkenylene dicarbonyls, such as vinylenedicarbonyl or 1,4-phthalene
2-phenylene dicarbonyl, or cyclohexylene dicarbonyl, such as p-cyclohexylene dicarbonyl. However, the divalent group R26 of the aliphatic carboxylic acid is C
It may be a divalent group of 36-dicarboxylic acid, and the trivalent group may be a residue of C37-C54-tricarboxylic acid. The divalent base of aromatic or heterocyclic carboxylic acid is
Especially having 6 to 12 carbon atoms, for example phenylene dicarbonyl, such as o-, m- or p-phenylene dicarbonyl, or pyridine-2,4- or -2,5-dicarbonyl or thiophene. -2,5-dicarbonyl. The radical R26 as P-alkyl preferably has 1 to 4 carbon atoms, for example methyl or ethyl. >P-
The radical R as aryl is in particular >P-phenyl.
>The radical R26 as P-aralkyl has in particular 7 to 12 carbon atoms and optionally an alkyl and/or hydroxyl group of 1 to 12 carbon atoms, in particular 1 to 8 carbon atoms, in the aralkyl moiety; For example penzyl or 3,5-di-tert-butyl-4-hydroxybenzyl. alkylene range
Aminocarbonyl R26 is unsubstituted in the amino moiety or substituted with alkyl having especially 1 to 6 carbon atoms, such as methyl, and in the alkylene moiety having especially 2 to 10 carbon atoms,
Examples include ethylene or tetramethylene. Arylene-di-aminocarbonyl R26 is unsubstituted in the amino moiety or substituted, in particular with alkyl having 1 to 6 carbon atoms, such as methyl, in particular in the arylene moiety
~10, especially 6 carbon atoms and optionally alkyl substituents, such as methyl, such as o-, m- or p
-phenylene-di-aminocarbonyl. Malonyl R26 is advantageously a mono- or di-substituted malonyl in compounds of formula (V) in which q'' is 2 and the remaining symbols of formula (V) have the general and advantageous definitions given above. be.

The substituent at the 2-position of malonyl is one or two 3
, 5-dialkyl-4-hydroxy-penzyl group (alkyl having 1 to 8 carbon atoms). Alkyl is especially primary, secondary or especially tertiary alkyl, such as methyl, tert-octyl or especially tert-butyl. Examples of malonyl of this type include, in particular, 3,5-di-tert-butyl-4
-hydroxybenzylmalonyl and bis-(3,5-di-t-butyl-4-hydroxybenzyl)-malonyl. In compounds of formula (V) in which q'' is 2 and the others exhibit the general and advantageous definitions given above, substituted malonyl R
26 is also advantageously of the following formula (Va); [wherein R26' represents 3,5-dialkyl-4-hydroxybenzyl or 2,6-dialkyl-3-hydroxybenzyl, R26'' is a monovalent 1 to 18 carbon atoms as a group
, cyanoalkyl having 2 to 5 carbon atoms, C, -C4
-Alkoxycarbonyl-C,-C4-alkyl, optionally N-C. -C,2-alkylated or pendylated 2,2,6,6-tetra-C,1C6-alkylpiveridinyl-4-oxycarbonyl-C,1C4-alkyl,C21-C,8-alkanoyloxy -C, 1C4-
Alkyl, cyclohexylcarbonyloxy-C, 1C
4-alkyl, benzoyloxy-C. -C4-alkyl or pendylcarbonyloxy-1C,1C4-alkyl, di(C.1C4-alkyl)-phosphonoC,1C4
-alkyl, di-allylphosphono-C, -C4-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, phenyl or C7-C represents aralkyl, R2
6'' is a divalent group, such as a direct bond, an alkylene having 1 to 12 carbon atoms which may be interrupted by one or two -○-, -S- or -CO-○-, C8- C,
4-arylenepisalkylene or C4-C8-alkenylene].

R26' is 33,5-di-t-butyl-4-hydroxybenzyl or 2,6-di-t-butyl-3-hydroxybenzyl, and R26'' is a monovalent group such as alkyl having 1 to 8 carbon atoms, C3-C4 - alkenyl, propargyl, benzyl, phenyl or optionally N-methylated or N-benzylated 2,2,6,6-tetramethyl-piveridinyl-4-oxocarbonylmethyl, with R26 as the divalent group; '' is preferably C2-C6-alkylene or C8-C,4-arylenebisalkylene. Alkyl in hydroxybenzyl R26'' especially has 1 to 8 carbon atoms, such as methyl, t-octyl and especially t-butyl. Alkyl R2 is especially alkyl having 1 to 8 carbon atoms, such as methyl. Cyanoalkyl R26'' is, for example, cyanomethyl.Alkoxycarbonylalkyl R2
6/'' is in particular C,1C4-alkoxycarbonylmethyl, such as methoxycarbonylmethyl. The 2- and 6-layer moieties in the piveridinyl group are especially methyl,
Alkanoyloxy-alkyl R26″ is especially C2-C
, 8-alkanoyloxy-methyl, such as acetoxymethyl. Cyclohexylcarbonyloxyalkyl R26'' is, for example, cyclohexylcarbonyloxymethyl. Penzoyloxyalkyl R26'' is, for example, penzoyloxymethyl. Penzylcarbonyloxyalkyl R26'' is, for example, penzylcarbonyloxymethyl.Dialkylphosphonoalkyl R
26'' is, for example, dimethylphosphonomethyl. Diallylphosphonoalkyl R26'' is, for example, diallylphosphonomethyl. Alkenyl R26'' is, for example, methalyl, and alkynyl is, for example, propargyl.

Aralkyl R26'' is, for example, pendyl. Alkylene R26'' is, for example, ethyllene, and arylenebisalkylene is, for example, phenylenebismethylene. In formula (V), R and 9 are hydrogen, and R2.

is hydrogen or methyl, R2, is methyl, R2
2 and R24 are methyl or ethyl, R25 is hydrogen, methyl, allyl, benzyl, 2,3-epoxypropyl, 2-hydroxyethyl, alkanoyl moiety 2-18
2-alkanoyloxyethyl or 2-benzoyloxyethyl having 5 carbon atoms, especially hydrogen or methyl, and q″ is 1 or 2, when q″ is 1,
R26 is alkanoyl having 2 to 18 carbon atoms, benzoyl, penzoyl having 1 to 3 substituents, which are the same or different and are alkyl or hydroxyl groups having 1 to 4 carbon atoms;
8-(3,5-di-t-butyl-4-hydro.xyphenyl)-propionyl, alkyl moiety has 1 to 1 carbon atoms
8 alkylcarbamoyl, phenylcarbamoyl or cyclohexylcarbamoyl, and when q″ is 2, R26 is a fullkylene dicarbonyl having 2 to 12 carbon atoms in the alkylene moiety, 3-azabentamethylene dicarbonyl, phenylene dicarbonyl Carbonyl, sulfinyl, hexamethylene-di-aminocarbonyl, 2,4-tolylene-di-aminocarbonyl or methylene-di(p
-phenylene-aminocarbonyl). R2. When is methyl, R and R24 are preferably ethyl. R2. is hydrogen, R
22 and R24 are preferably methyl. When q'' is 1, R scales are alkanoyl or benzoyl having 2 to 18 carbon atoms, benzoyl having 1 to 3 substituents which are the same or different and are alkyl or hydroxyl groups having 1 to 4 carbon atoms; or 8-(3,5-di-t-butyl-4-hydroxyphenyl)-propionyl, and when q″ is 2, R26 is an alkylene moiety having 2 to 12 carbon atoms.
Particular preference is given to alkylene dicarbonyl, 3-azabentamethylene dicarbonyl or phenylene dicarbonyl, such as, for example, 4-benzoyloxy-2,6-diethyl-2,3,6-trimethylpiveridine, 4-benzoyloxy-2,2,6,6-tetramethylpiveridine, 4-stearoyloxy-2,2,
6,6-tetramethylpiveridine or bis(2,2,
6,6-tetramethyl-4-piveridyl)-sebacate. A metal key body of formula (W) is also advantageous; and R28 each independently represent hydrogen, alkyl, alkenyl, alkynyl or aralkyl, R29 and R3o each independently represent alkyl, R3 represents alkyl, phenyl, benzyl or phenethyl, R32 represents alkyl, or R3. and R32 together represent tetramethylene or pentamethylene, R33 is hydrogen, oxyl, alkyl,
alkenyl, alkoxyalkyl, aralkyl, 2,
3-epoxypropyl, alkoxycarbonylmethyl,
Alkenyloxycarbonylmethyl, phenoxycarbonylmethyl, aralkoxycarbonylmethyl, cyclohexyloxycarbonylmethyl, 2-hydroxyethyl, 2-hydroxypropyl, 2-phenyl-2-hydroxyethyl, 2-acyloxyethyl, 2-acyloxypropyl or 2-phenyl-2-acyloxyethyl, R34 represents hydrogen, alkyl, cycloalkyl or aralkyl, q represents 1, 2 or 3, R35 is q''' is 1 , alkanoyl, alkenoyl, alkoxycarbonyl, benzyloxycarbonyl, cycloalkoxycarbonyl, arylcarbonyl, styrylcarbonyl, aralkylcarbonyl, heterocyclylcarbonyl, optionally substituted carbamoyl, alkylsulfonyl, arylsulfonyl, 1P(alkoxy)2, 1P (aryloxy)
2, 1P (alkyl) 2, 1P (aryl) 2, 1P (
aralkyl)2,1P(cyclohexyl)2,1P(
0 or S) (alkoxy) 2, 1 P (0 or S) (aryloxy) 2, 1 P (0 or S) (alkyl) 2, 1 P (0 or S) (aryl) 2, 1 P (0 or S)(aralkyl)2-P(0 or S)(cyclohexyl)2
or R35 and R34 together with the nitrogen atom to which they are bonded represent succinimide, maleimide,
or represents phthalimide, and when R35 is 2, carbonyl, oxalyl, alkylene dicarbonyl, thiaalkylene dicarbonyl, alkenylene dicarbonyl, arylene dicarbonyl, cyclohexylene dicarbonyl, alkylene di-aminocarbonyl, arylene dicarbonyl Aminocarbonyl, cyclohexylene-diaminocarbonyl, >P (alkoxy), >P (aryloxy), >P (alkyl), >P (aryl), >
P (aralkyl), >P (cyclohexyl), >P(
0 or S) (alkyl), >P (0 or S) (aralkyl) or >P (0 or S) (cyclohexyl), and when q is 3, R35 is benzenetricarbonyl, s triazine- 2,4,6-trill, woP,
(represents woPO or woPS).

The alkyl radicals R27 and R28 preferably have 1 to 5 carbon atoms, such as the methyl radical.

The alkenyl radicals R27 and R28, like the allyl group, in particular have 3 to 4 carbon atoms. The alkynyl radicals R27 and R28 in particular have 7 to 8 carbon atoms, like the penzyl radical. The alkyl radicals R29 and R3o preferably have 1 to 6 carbon atoms, such as methyl or ethyl. The alkyl group R3 has especially 1 to 9 carbon atoms, such as a methyl or ethyl group. The alkyl group R32 preferably has 1 to 6 carbon atoms, such as a methyl or ethyl group. The alkyl plug 33 specifically has 1 to 8 carbon atoms, such as a methyl group. The alkenyl plug 33 especially has 3 to 6 carbon atoms, such as an allyl group. The alkoxyalkyl group R33 preferably has 2 to 21 carbon atoms, especially 2 to 1 carbon atoms, such as 2-methoxyethyl group.
It has 2. The aralkyl group R33 particularly has 7 to 8 carbon atoms, such as a penzyl group or a phenethyl group, and in some cases, the aryl moiety is a chlorine atom, a hydroxyl atom, as in a 3,5-di-butyl-4-hydroxybenzyl group. C1-C4 alkyl group or C1-C4 alkoxy group.
In the alkoxycarbonylmethyl group R33, the alkyl portion particularly has 1 to 8 carbon atoms, like a methoxycarbonylmethyl group. Alkenyloxycarbonylmethyl group R
In 33, the alkenyl moiety particularly has 3 to 6 carbon atoms, such as an allyloxycarbonylmethyl group. In the aralkoxycarbonylmethyl group R33, the aralkyl moiety particularly has 7 to 8 carbon atoms, like the penzyloxycarbonylmethyl group. 2-acyloxyethyl, 2-acyloxypropyl, and 2-phenyl-2-acyloxyethyl groups R33 may contain a chlorine atom or a carbon atom in some cases, such as a 3,5-di-tert-butyl-4-hydroxy-penzoyl group. Penzoyloxy group substituted with an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, and/or a hydroxyl group, B-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionyl Penzylcarbonyl or phenethylcarbonyl groups in which the aryl moiety is optionally substituted with an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a chlorine atom and/or a hydroxyl group; The acyloxy moiety preferably has up to 18 carbon atoms, such as an aroyloxy group, an alkanoyloxy group, an alkenoyloxy group, such as an aralkylcarbonyl group such as or a cycloalkylcarbonyl group such as a cyclohexylcarbonyl group.

The alkyl group R34 is especially one having 1 carbon atom, such as a methyl group.
It has 12 to 12. Cycloalkyl radicals especially have 5 to 7 carbon atoms, such as cyclohexyl. Aralkyl group R34 especially has 7 carbon atoms, such as penzyl group.
to 8. Alkanoyl radical R35 especially has 2 to 18 carbon atoms, such as acetyl, propionyl, lauroyl or stearoyl. The alkenyl radical R35 in particular has 3 to 6 carbon atoms. In the alkoxycarbonyl group R35, the alkoxy moiety, such as a methoxycarbonyl group, particularly has 1 to 8 carbon atoms.
In the cycloalkoxycarbonyl group R35, the cycloalkoxy moiety particularly has 5 to 7 carbon atoms, like a cyclohexyloxycarbonyl group. The arylcarbonyl group 35 is particularly 3,5-di-tert-butyl-4-hydroxy-
It represents a penzoyl group optionally substituted with a chlorine atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and/or a hydroxyl group, such as penzoyl. The aralkyl group is followed by a penzylcarbonyl group or a phenethylcarbonyl group, in particular the aralkyl part has 7 to 12 carbon atoms and the aryl part is a 6-(3,5-di-tert-butylphenyl)-propionyl group. In some cases, chlorine atoms, such as
Substituted with an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms and/or a hydroxyl group. As the heterocyclic carbonyl radical 35, for example, 2-
, 3- or 4-pyridinylcarbonyl group, 2-furylcarbonyl group or 2-chenylcarbonyl group. optionally substituted carbamoyl group R35
Examples include a carbamoyl group, an alkylcarbamoyl group in which the alkyl moiety has 1 to 18 carbon atoms, and a phenylcarbamoyl group in which the phenyl moiety may be substituted with a chlorine atom or an alkyl group having 1 to 4 carbon atoms. An arylcarbamoyl group in which the aryl moiety has 6 to 10 carbon atoms, such as an aralkylcarbamoyl group or cyclohexylcarbamoyl group in which the aralkyl group has 7 to 8 carbon atoms, such as benzylcarbamoyl group In this case, mention may be made of mono- or di-substituted carbamoyl radicals in which these carbamoyl radicals can have a C 1 -C 4 alkyl radical, in particular a methyl radical, as second N-substituent.
The alkylsulfonyl group R35 represents in particular a methyl group or an ethylsulfonyl group. Arylsulfonyl group R35
represents in particular a phenyl or trisulfonyl group. R
The alkoxy group in the P group described as 35 has in particular 1 to 12 carbon atoms, like the methoxy group; the aryloxy group has especially 6 to 12 carbon atoms, like the phenoxy group; the alkyl group has especially a methyl group. Aryl, like phenyl, especially has 6 to 14 carbon atoms; aralkyl, like penzyl, especially has 7 to 8 carbon atoms. The alkylene dicarbonyl group R$ has especially 1 to 10 carbon atoms in the alkylene part, such as a methylene, ethylene or octamethylene group. Thia-alkylene dicarbonyl radicals, such as the 3-thia-pentamethylene dicarbonyl group, preferably have a total of 4 to 6 carbon atoms. The alkenylene dicarbonyl group preferably has a total of 4 to 6 carbon atoms. Arylene dicarbonyl represents a phenylene dicarbonyl group or in particular an alkyl-phenylene dicarbonyl group in which the alkyl moiety has 1 to 4 carbon atoms. An alkylene-diaminocarbonyl group R35 has in particular 2 to 10 carbon atoms in the alkylene moiety, such as an ethylene- or 1,4-butylene-diaminocarbonyl group. In arylene-di-aminocarbonyl R35, the arylene moiety particularly has 6 to 13 carbon atoms, like the phenylene-di-aminocarbonyl group. R27 represents a hydrogen atom, R28, R29 and R3 represent a methyl group, and R3. and R32 preferably represent an ethyl group, particularly preferably R27
and R28 represents a hydrogen atom, R29, R, R3,
and R32 represents a methyl group. In the compound of formula, the methylene dicarbonyl (malonyl) group R35 preferably represents a monosubstituted malonyl group in which q... represents 2, and the remaining symbols of formula W have the general and preferred meanings given above.

The substituent at the 2-position of the malonyl group is 3,5-dialkyl-
4-hydroxy-penzyl group (alkyl group has 1 to 8 carbon atoms). In particular, alkyl represents a primary, secondary or tertiary alkyl group, such as methyl, tert-octyl or especially tert-butyl. Examples of such malonyl groups include 3,5-di-tert-butyl-4
-Hydroxypendylmalonyl group. The piveridine group in parentheses p is b of the following formula: (where n* is 1
or 2, Y* represents an oxy group or an imino group, R, *, R2* and R3* each independently represent an alkyl group having 1 to 6 carbon atoms, and R4* represents a carbon atom number 1 to 9 alkyl group, phenyl group, benzyl group or Q-phenylethyl group, or R3
* and R4* together represent a tetramethylene group or a pentamene group, R5* and R6* each independently represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and R7* and R8* are independently of each other, the number of carbon atoms is 1
represents an alkyl group having 7 to 9 carbon atoms, an aralkyl group having 7 to 9 carbon atoms, or a cycloalkyl group having 5 to 8 carbon atoms, R9* represents a hydrogen atom or a methyl group, and X* represents a hydrogen atom, an oxyl group, a carbon Alkyl group having 1 to 12 atoms, alkenyl group having 3 to 6 carbon atoms, alkynyl group having 3 to 4 carbon atoms, alkoxyalkyl group having 2 to 21 carbon atoms, aralkyl group having 7 to 8 carbon atoms , 2,3-epoxypropyl group or the following formula: -CH2C
OOR, o* or -C is -CH(R,.*)-OR,
2*{In the formula, R and o* represent an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 3 to 6 carbon atoms, a phenyl group, an aralkyl group having 7 to 8 carbon atoms, or a cyclohexyl group, R, ．． * represents a hydrogen atom, a methyl group, or a phenyl group, and R,2* represents a hydrogen atom, an aliphatic, aromatic, araliphatic, or alicyclic acyl group having 1 to 18 carbon atoms (in the formula, the aromatic moiety may be a chlorine atom,
Alkyl group having 1 to 4 carbon atoms, 1 to 8 carbon atoms
may be substituted with an alkoxy group and/or a hydroxyl group.

). }, and R. 4
* is a cyano group, one CHO-, one COR, 6*, -SQ-
R,7*, 1P(=0)(OR.8*)2 or a nitro group, where R,6* and R,7* have 1 carbon atom
R. 6* represents a group bonded to R, 5*, and R
, 8* represents an alkyl group having 1 to 18 carbon atoms, a phenyl group or an allyl group. And R, 5* is a hydrogen atom when n represents 1; c in the following formula; (in the formula R7*, R
8* and R9 represent the above meanings, or an alkyl group or phenoxy group having 1 to 20 carbon atoms, an alkylphenoxy group having 7 to 10 carbon atoms, a benzyloxy group, a cyclohexyloxy group, a phenylthio group, or a phenylthio group having 7 carbon atoms.
to 10 alkyl phenylthio groups, alkanoyl groups having 2 to 13 carbon atoms, cyano groups, 1C(=○)OR,
9*, 10-C (=○) R2.

* or represents an alkyl group having 1 to 10 carbon atoms substituted by 1P(=0)(OR2,*)2, in which case R,9* represents an alkyl group having 1 to 18 carbon atoms, an alkyl group having 1 to 18 carbon atoms, 5 to 12 cycloalkyl groups or d of the following formula: (
In the formula R. *, R2*, R3*, R4*, R5*, R6*
and ×* represent the above meanings.

), and R number * represents an alkyl group having 1 to 17 carbon atoms, a cycloalkyl group having 5 to 12 carbon atoms, a phenyl group, or a phenylalkyl group having 7 to 9 carbon atoms (in which case, The two groups have a phenyl moiety of 2
may be substituted with C1-C4 alkyl groups and/or hydroxyl groups. ), and R2,* represents an alkyl group having 1 to 8 carbon atoms, an allyl group, or a phenyl group. And R,5* is further 10-, 1S-,
represents an alkyl group having 2 to 22 carbon atoms interrupted by 1-SO- or 1-S02-, or an alkenyl group having 3 to 18 carbon atoms, an alkynyl group having 3 to 8 carbon atoms, or an alkynyl group having 5 to 12 carbon atoms; a cycloalkyl group having 6 to 18 carbon atoms, a cycloalkylalkyl group having 6 to 14 carbon atoms, an aralkyl group having 7 to 19 carbon atoms, an alkylaralkyl group having 7 to 19 carbon atoms, represents a phenyl group or a group represented by d in the above formula, or optionally an oxo group and/or an adjacent R. 4*
(R, 4* represent the above meanings.) and e of the following formula: (X*, Y*, R, *, R2*, R3*, R4*'R5
* and R6* represent the above meanings.

) represents a trimethylene group or a tetramethylene group substituted with
Direct bond, alkyl group having 1 to 20 carbon atoms, interrupted by one or two 10-, 1S-, 1SO1, 1S02- or 1CO-○-, having 2 to 20 carbon atoms represents an alkylene group having 8 to 14 carbon atoms, an allene-bis-alkylene group having 8 to 14 carbon atoms, an alkenylene group having 4 to 8 carbon atoms, or an alkynylene group having 4 to 8 carbon atoms.

The metal body of the formula a corresponding to the formula W representing a group represented by ] is particularly suitable, and Me, r, L and s have the abovementioned meanings. R, *, as an alkyl group
R2* and R3* are linear groups having 1 to 6 carbon atoms, such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, isobentyl group, or n-hexyl group, or Represents a branched alkyl group.

Among the preferred compounds, the compounds to be described are R, * and R.
This is a compound in which 3* represents a methyl group or an ethyl group, and R2* represents a methyl group. R4* as an alkyl group
is a methyl group, ethyl group, isopropyl group, n-butyl group, isobentyl group, n-hexyl group, 2-ethylhexyl group or isononyl group, especially a methyl group having 1 to 9 carbon atoms, especially 1 to 9 carbon atoms, 6 and especially a straight-chain or branched alkyl group having 1 carbon atom.

R5 and R6 as alkyl groups having 1 to 5 carbon atoms
represents a straight-chain or branched alkyl group, such as methyl, ethyl, isopropyl, isobutyl, n-pentyl.

R5 preferably has one less carbon atom than R,*;
R6* has one less carbon atom than R2*. Preferably R5* represents a hydrogen atom or a methyl group and R
6* represents a hydrogen atom. A penzyl group with R7*, R8* and R9* can be a para- or meta-hydroxybenzyl group. Substituents R7* and R of penzyl group
Examples of 8* include methyl group, ethyl group, isopropyl group, tert-butyl group, n-hexyl group, 1,1,3,3
- It can be a straight chain or branched alkyl group having 1 to 9 carbon atoms, such as a tetramethylbutyl group or a tertiary nonyl group. When R7* or R8* represents a cycloalkyl group, it can be, for example, a cyclobentyl group, a methylcyclobentyl group, a cyclohexyl group or a methylcyclohexyl group. When R7* or R8* represents an aralkyl group, it can be, for example, a penzyl group or a Q,Q-dimethylbenzyl group. Preferably R7* and R8* represent an alkyl group having 1 to 4 carbon atoms, especially a methyl group or a tert-butyl group. X* as an alkyl group having 1 to 12 carbon atoms is, for example, a methyl group, ethyl, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-octyl group, n-decyl group or n- Represents a dodecyl group.

Alkyl is preferably C1 -C8 alkyl, especially C1 -C4 alkyl and especially methyl. X* as C3 -C6 alkenyl is, for example, allyl, 2-butenyl or 2-hexenyl, in particular allyl.

X* as an alkynyl group having 3 to 4 carbon atoms represents, for example, a propargyl group.

When X* represents an alkoxyalkyl group having 2 to 21 carbon atoms, for example, methoxymethyl group, ethoxymethyl, 2-methoxyethyl group, 2-ethoxyethyl group, 2
-n-butoxycetyl group, 3-n-butoxycetyl group,
The alkyl moiety may contain 1 to 3 carbon atoms and the alkoxy group may consist of 1 to 18 carbon atoms, especially when Compounds representing an alkoxyalkyl group having numbers 2 to 6 may be mentioned.

Examples of x* as an aralkyl group having 7 to 8 carbon atoms include a penzyl group or a Q-phenylethyl group.

X* is a group -CH2COOR. When o* is represented, R as an alkyl group having 1 to 12 carbon atoms, o* is, for example, a methyl group, ethyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, isobentyl group, n-octyl group. group, n-decyl group or n-dodecyl group.

R and o* are preferably alkyl groups having 1 to 4 carbon atoms. R,o* as alkenyl group having 3 to 6 carbon atoms
is, for example, an allyl group, a 2-putenyl group or a 2-hexenyl group. R, o* as aralkyl having 7 to 8 carbon atoms represents, for example, penzyl group or Q-phenylethyl group. X* is a group -CH2-CH(R, .
*) -OR, 2*, R, . * represents a hydrogen atom, a methyl group or a phenyl group, especially a hydrogen atom.

Aliphatic, aromatic, cycloaliphatic or araliphatic carbon number: 1
As the acyl group of 1 to 18, R, 2* may be an alkyl group having 1 to 4 carbon atoms such as a chlorine atom, a methyl group, an ethyl group, an n-propyl group, or tert-butyl, or Optionally substituted with C1-C8 alkoxy and/or hydroxyl groups such as methoxy, ethoxy, butoxy or octoxy; for example acetyl, propionyl, butyryl, octanoyl, dodecanoyl. group, stearoyl group, acryloyl group, benzoyl group, chlorobenzoyl group, toluoyl group, improbilbenzoyl group, 2,4
-dichlorobenzoyl group, 4-methoxybenzoyl group,
3-butoxybenzoyl group, 2-hydroxybenzoyl group, 3,5-di-tert-butyl-4-hydroxybenzoyl group, 8-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionyl group, phenyl Examples include acetyl, cinnamoyl, hexahydrobenzoyl, 1- or 2-naphthoyl or decahydronaphthyl. R as an alkyl group having 1 to 17 carbon atoms,
6* and R, 7* particularly have the same meaning as X* as an alkyl group having 1 to 8 carbon atoms, especially a methyl group; The alkylphenyl group represented by 9 is, for example, methylphenyl, ethylphenyl or propylphenyl; the hydroxyalkylphenyl group having 11 to 14 carbon atoms is preferably an alkyl group such as a methyl group or especially a tert-butyl group. In particular, 4-hydroxy-3, having 1 to 8 carbon atoms, especially 4-hydroxy-3, having 1 to 4 carbon atoms;
5-dialkylphenyl group; Similarly, hydroxyalkyl group having 12 to 16 carbon atoms; phenylalkyl group particularly includes 4-hydroxy-3,5-dialkylbenzyl group, 4-hydroxy-3,5-dialkylphenethyl group or 4-Hydroxy-3,5-dialkyl-8-phenylpropylpropyl group.

R as an alkyl group having 1 to 20 carbon atoms,
5* is, for example, one of the alkyl groups mentioned above for ×*
They also mean branched alkyl groups such as isopropyl, isobentyl, 2-ethylbutyl, 2-ethylhexyl or isononyl or, for example, n-hexadecyl, n-octadecyl or n-
- Can be a higher alkyl group such as an eicosyl group.

Substituted or interrupted alkyl groups include R,
5* can be, for example, one of the following groups: 2-phenoxyethyl, 2-benzoyloxyethyl, 21p-tolyloxypropyl, cyclohexyloxymethyl, 21(8- naphthoxy)-ethyl group, 2-phenylthioethyl group, 2-(4-tert-butylphenylthio)-ethyl group, 2-acetylethyl group, 2-isobutylethyl group, 2-(dodecylcarbonyl)-ethyl group, 2 -cyanoethyl group, cyanomethyl group, 3-cyanopropyl group,
Methoxycarbonylmethyl group, dodecyloxycarbonylmethyl group, 2-ethoxycarbonylethyl group, 2-(
cyclohexyloxycarbonyl)ethyl group, 2-(tert-butyloxycarbonyl)ethyl group, 2-(octadecyloxycarbonyl)-propyl group, 4-(propoxycarbonyl)-butyl group, 2-acetoxyethyl group,
2-(isooctanoyloxy)propyl group, 2-(
octadecanoyloxy)ethyl group, 2-(cyclobentylcarbonyloxy)ethyl group, 3-penzoyloxypropyl group, 2-(p-tert-butylbenzoyloxyethyl group, 2-salioxyethyl group) Tyroloxyethyl group, 2-(3
, 5-di-tert-butyl-4-hydroxybenzoyloxy)-ethyl group, 2-phenylacetyloxyethyl group, 2-(3,5-di-tert-butyl-4-hydroxyphenylpropionyloxy)-propyl group, Tylphosphonomethyl group, 2-dimethylphosphonoethyl group, 2-
(dioctylphosphono)-ethyl, diphenylphosphonomethyl group, 3-(diallylphosphono)-propyl group,
Methoxymethyl group, 2-butoxyethyl group, 2-octadecyloxyethyl group, isopropoxymethyl group, 3-
Butylthiopropyl group, 2-dodecylthioethyl group, 2
-(isohexylsulfinyl)-ethyl group, 2-octadecylsulfonylethyl group, 2-ethylsulfonylpropyl group. R as alkenyl or alkynyl group
, 5* is, for example, allyl group, methallyl group, 2-butene-1
-yl group, 3-hexen-1-yl group, undecenyl group, oleyl group, propargyl group or 2-hebutyne-1
-yl group.

Examples of R, 5* as a cycloalkyl group, an alkylcycloalkyl group, or a cycloalkyl-alkyl group include a cyclobentyl group, a cyclohexyl group, a cyclooctyl group, a cyclododecyl group, a methylcyclobentyl group,
Examples include dimethylcyclohexyl group, propylcyclooctyl group, hexylcyclododecyl group, cyclohexylmethyl group, 3-cyclooctylpropyl group, and decahydronaphthyl-Q-methyl group.

R as aralkyl group or alkyl-aralkyl group
, 5* include, for example, penzyl group, 2-phenylethyl group, 2-phenylpropyl group, 8-naphthylmethyl group,
Examples include 4-methylbenzyl group, 4-tert-butylbenzyl group, and 4-methylnaphthyl-1-methyl group.

When n represents 2, R,5* represents a direct bond or a divalent organic residue.

These can be, for example, methylene groups, ethylene groups or polymethylene groups having up to 20 carbon atoms. Or the alkylene group is a divalent group, one CH20-CH2-, one C
Ratio CH20-CH2CH2-,-CH2C ratio-○-CQ
C day 21○-CH2CH21,1 (CQ)31S-(C
3-, 1CH2CQ-S-(CH2)4-S-C&
CH21,1CH2Cday21SO-CH2CH2-,1CQCday2-S02-Cmochi2CH2-,1CH2C ratio-S021(CH2)81SQ-CQCday2-CQCO
OCH2CH200CCH2CQCH2COOCH2C
H200CCH2C ratio 1 CQC day 21 COO (CH2)
4-00C-CH2C uniform, C&CH20C.

(CH2)4COOCH2CH2-C ratio CH20C○(
CH2) interrupted by one or two heteroatoms, such as COOCH2CH2. This also includes p-xylylene, benzene-1,3-bisethylene, diphenyl-
It can be an arene-bis-alkylene group such as a 4,4'-bismethylene or naphthalene-1,4-bismethylene group. Finally this is 2-butenylene-1,4, 2-butenylene-1,4 or 2,4-hexadiynylene-1
, 6 or an alkynylene group having 4 to 8 carbon atoms. A preferred compound Wa of formula a is one in which n* represents 1 or 2, Y* represents an oxy group or an imino group, and R, *, R2*, R
3* and R4* each independently represent an alkyl group having 1 to 6 carbon atoms, or R8* and R4* together represent a tetramethylene group or a pentamethylene group, and R5
* and R6* each independently represent a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R7* and R8* each independently represent an alkyl group having 1 to 4 carbon atoms,
R9* represents a hydrogen atom, X* is a hydrogen atom, oxyl group, alkyl group having 1 to 8 carbon atoms, alkenyl or alkynyl group having 3 to 4 carbon atoms, alkoxyalkyl group having 5 to 6 carbon atoms an aralkyl group having 7 to 8 carbon atoms or the following formula: -CH2-COOR; * or one C ratio -CH(R,.*)-OR,2* [in the formula R, o
* indicates an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 3 to 4 carbon atoms, a phenyl group, or a 7 to 8 carbon atom group.
represents an aralkyl group or a cyclohexyl group, R,
．． *represents a hydrogen atom, methyl group or phenyl group,
R, 2* is a hydrogen atom or an aliphatic, aromatic, alicyclic or araliphatic acyl group having 1 to 18 carbon atoms (the aromatic moiety may be a chlorine atom or an alkyl group having 1 to 4 carbon atoms, depending on the case) , may be substituted with an alkoxy group having 1 to 8 carbon atoms and/or a hydroxy group), and R, 4
* is a cyano group, -COR, 6* (R, 6* represents the above meaning), -S02-R, 7* (R, 7* represents the above meaning) or -P (=○) ( OR,8*)2(R
, 8* represent the above meaning. ) represents a group R.
5* means when n represents 1, a hydrogen atom, a group represented by c in the formula expressing the above meaning, an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 3 to 4 carbon atoms, a propargyl group, a benzyl group. groups, phenyl groups, and nitrile groups, 1C(=○)OR, 9*, 10-C(C=○)R2.
*or 1P(=○)(OR,2*)2(R,9*,R
2o*, R, 2* represent the above meanings. ) or a group of the formula V1d having the abovementioned meanings or trimethylene, optionally substituted as described above, formed together with R, 6*; or a tetramethylene group, and when n represents 2, R, 5* is a compound representing an alkylene group having 2 to 6 carbon atoms or an allene-pis-alkylene group having 8 to 14 carbon atoms. Compounds represented by a of the formula (2) Particularly preferred compounds b are those in which n* is 1 or 2.
, Y* represents an oxy group or an imino group, and R
, * and R3* represent a methyl group or an ethyl group, and R
2* and R4* represent a methyl group, R5* represents a hydrogen atom when R and * represent a methyl group, R5* represents a methyl group when R and * represent an ethyl group, and R6* represents a methyl group.
represents a hydrogen atom, R7* and R8* each independently represent an alkyl group having 1 to 4 carbon atoms, and R
9* represents a hydrogen atom, in which case R7*, R8* and R
The penzyl group carrying 9* represents a 4-hydroxy-penzyl group, and X* is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an allyl group, a propargyl group, or an alkoxyalkyl group having 2 to 6 carbon atoms, or 1C ratio COOR
,.

* (in the formula, R, o* represent an alkyl group having 1 to 4 carbon atoms), -CH2-CH(R,.*)-OH (in the formula, R, .* represent a hydrogen atom or a methyl group) .), R, 4* is a cyano group, -C representing the above meaning
OR, 6* group or -S02-R representing the above meaning,
7* group, and when n* represents 1, R, 5* is a hydrogen atom, 4-hydroxy-3,5-di alkylbenzyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 12 carbon atoms. , an alkenyl group having 3 to 4 carbon atoms, a bropargyl group, a benzyl group, a phenyl group or f, W of the following formula
g: (wherein R, *, R2*, R3*, R4*, R5* and X represent the preferred meanings given above for a in the formula.

), and R* and R23* represent a hydrogen atom or a methyl group, or a trimethylene or tetramethylene group optionally substituted as described above when formed together with R,6*. , when n is 2, R, 5* is a compound representing an n-alkylene group having 2 to 6 carbon atoms or an arene-bis-alkylene group having 8 to 14 carbon atoms. What should be particularly emphasized in the formula Wa is that n* represents 1 or 2, Y* represents an oxy group or an imino group, R, *, R2*, R3* and R, * represent a methyl group, and R5 * and R6* represent a hydrogen atom, or R, * and R3* represent an ethyl group, R2*, R4* and R5* represent a methyl group,
and R6 represents a hydrogen atom, R7* and R8* represent a methyl group or a tert-butyl group, and R9* represents a hydrogen atom, in which case the penzyl group carrying R7*, R8* and R9* is a 4- Represents hydroxybenzyl group, ×*
represents a hydrogen atom or a methyl group, R, 4* represents a cyano group, 1COR, 6* (R, 6* represents an alkyl group having 1 to 6 carbon atoms or an alkylsulfonyl group having 1 to 6 carbon atoms) .

) group, R, 5* represents a hydrogen atom when n represents 1, a 4-hydroxy-3,5-di-tert-butylbenzyl group, an n-alkyl group having 1 to 12 carbon atoms, a benzyl group, Phenyl group, optionally N-methylated (2,2
,6,6-tetramethyl-piveridinyl-4-oxycarbonylmethyl group or optionally N-methylated (2,3,6-triethyl-2,6-dimethyl-piveridinyl-4)-oxycarbonyl group Represents a methyl group or a trimethylene group or tetramethylene group formed together with R,6*, and when n represents 2, R,5*
is a compound Wa representing an n-alkylene group having 2 to 6 carbon atoms. Among these compounds, compounds that should be particularly emphasized are those in which n* is 1 in formula a, Y* is an oxy group, and R, *, R2*, R3*, R4*, R
5*, R6*, R? *, R8*, R9*, Represents 1 to 6 alkyl groups.

) group or a trimethylene group or tetramethylene group formed together with R, 5*. Preferably, in the body of the formula, R27 represents a hydrogen atom, R27 represents a hydrogen atom or a methyl group, and R27 preferably represents a hydrogen atom or a methyl group;
29 and R3 represent a methyl group or an ethyl group, and R
3.

and R32 represents a methyl group, R33 is a hydrogen atom, an oxyl group, a methyl group, an allyl group, a benzyl group, an alkoxycarbonylmethyl group having 1 to 4 carbon atoms in the alkoxy moiety, a 2-hydroxyethyl group, an alkanoyl group. represents a 2-alkanoyloxyethyl group or a 2-penzoyloxyethyl group having 1 to 4 carbon atoms in the oxy moiety, R33 particularly represents a hydrogen atom or a methyl group, and R3
4 represents a hydrogen atom or a methyl group, q represents 1 or 2, and when q represents 1, R35 is an alkanoyl group having 2 to 18 carbon atoms, the same or different 1 to 3 substituents [ Alkyl group and/or hydroxyl group having 1 to 4 carbon atoms or 8-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionyl group, methylsulfonyl group, phenylsulfonyl group, tolylsulfonyl group, carbon of alkyl moiety represents a penzoyl group having an alkylcarbamoyl group, phenylcarbamoyl group or cyclohexylcarbamoyl group having 1 to 12 atoms, and when q... represents 2, R35 represents a carbonyl group, oxalyl group, or alkylene moiety; Alkylene dicarbonyl group having 1 to 10 carbon atoms, phenylene dicarbonyl group, hexamethylenediaminocarbonyl group, 2,
4-tolylene-di-aminocarbonyl group or 4,4'
-diphenylenemethane- is a compound representing a diaminocarbonyl group. For example, 4-acetamido-2,6-diethyl-2,3,6-trimethylpiveridine, 4-benzamido-2,2,6,6-tetramethylpiveridine or N,N'-bis-(2,2, 6,6-tetramethyl-4-piveridyl-succinic acid amide.Also preferred is the following formula: [wherein Me, p, q, r, s and L represent the meanings listed as preferred above, R36 and R nails each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, or an aralkyl group, R38 and R39 each independently represent an alkyl group, and R4.

represents an alkyl group, phenyl group, benzyl group or phenethyl group, R4 represents an alkyl group or
4. and R represents a tetramethyllene group or pentamethylene group formed together with R4, and when q represents 1, R42 is a hydrogen atom, an oxyl group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxyalkyl group, an aralkyl group, 2,3-epoxypropyl group, alkoxycarbonylmethyl group, alkenyloxycarbonylmethyl group, phenoxycarbonylmethyl group, aralkoxycarbonylmethyl group, cyclohexyloxycarbonylmethyl group, 2-hydroxyethyl group, 2-hydroxybropyl group group, 2-phenyl-2-hydroxyethyl group, 2-acyloxyethyl group, 2-acyloxypropyl group or 2-phenyl-2-acyloxyethyl group, q
represents 2, R42 is an alkylene group, a 1,4-buto-2-enylene group, an alkylene-di(carbonyloxyethylene) group, an alkylene-di(carbonyloxy-methylethylene) group (the methyl group is at the Q-position with respect to the carbonyloxy group) ) represents alkylene-di-(phenylethylene), (the phenyl group is in the Q position with respect to the carbonyloxy group), alkylene-dioxycarbonylmethyl or xylylene-dioxycarbonylmethyl. ] It is a metal flange body. The alkyl radicals R36 and R37 preferably have 1 to 5 carbon atoms, such as the methyl radical. The alkenyl groups R36 and R37 have 3 to 4 carbon atoms, like the allyl group. The alkynyl radicals R36 and R37 preferably have 3 to 4 carbon atoms, such as the propargyl radical. Aralkyl radicals R36 and R37, like the penzyl radical, in particular have 7 to 8 carbon atoms. The alkyl radicals R38 and R39 preferably have 1 to 6 carbon atoms, such as methyl or ethyl. The alkyl group R4o, like the methyl group, in particular has 1 to 9 carbon atoms. The alkyl group R4, like the methyl group, in particular has 1 to 6 carbon atoms. Alkyl group R
42 particularly has 1 to 8 carbon atoms, such as a methyl group. The alkenyl group R42 has 3 to 6 carbon atoms, like the allyl group. The alkynyl group R42, like the propargyl group, in particular has 3 to 4 carbon atoms. The alkoxyalkyl group R42 has especially 2 to 21 carbon atoms, in particular 2 to 12 carbon atoms, like the 2-methoxyshetyl group. The aralkyl group R42, like the penzyl group, in particular has 7 to 8 carbon atoms. The alkoxycarbonylmethyl group R42 has particularly 1 to 12 carbon atoms in the alkoxy moiety, like a methoxycarbonylmethyl group. The alkenyloxycarbonylmethyl group R42 particularly has 3 to 6 carbon atoms in the alkenyloxy moiety, like the allyloxycarbonylmethyl group. The aralkoxycarbonylmethyl group R42 preferably has 7 to 8 carbon atoms in the aralkoxy group, such as the penzyloxycarbonylmethyl group. 2-acyloxyethyl group, 2-acyloxypropyl group and 2-phenyl-2-acyloxyethyl group R42, for example, the following aliphatic groups having up to 18 carbon atoms,
Including acyl groups of aromatic, cycloaliphatic, araliphatic carboxylic acids: alkanoyl groups such as acetyl or propionyl groups; optionally, such as 3,5-di-tert-butyl-4-hydroxybenzoyl group; A penzoyl group substituted with a chlorine atom, a C1-C4 alkyl group, a C1-C8 alkoxy group and/or a hydroxyl group: a cyclohexylcarbonyl group; or an aralkylcarbonyl group such as P-(3,5-di In some cases, the phenyl moiety is substituted with a chlorine atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, and/or a hydroxyl group, such as in the case of tert-butyl-4-hydroxyphenyl-propionyl group. For example, a pendylcarbonyl group or a phenethylcarbonyl group.

The alkylene radical R42, like the tetramethylene radical, in particular has 4 to 8 carbon atoms.

Examples of the alkylene group include, in particular, an alkylene group R42 having 1 to 10 carbon atoms, such as a methylene group or an ethylene group. Alkylene-dioxycarbonylmethyl group The alkylene group in R42 particularly has 2 to 8 carbon atoms, such as an ethylene group.
has. Among the flange bodies represented by the type plate, preferably R
36 represents a hydrogen atom, R37 represents a hydrogen atom or a methyl group, R38 and R4. represents a methyl group or an ethyl group, R39 and R4. represents a methyl group,
When q represents 1, R42 is a hydrogen atom, a methyl group, or 2 in which the alkanoyloxy moiety has 2 to 12 carbon atoms;
-alkanoyloxyethyl group, 2-benzoyloxyethyl group, 2-(3,5-di-tert-butyl-4-hydroxy-benzoyloxy)ethyl group or 2-[B-(
3,5-di-tert-butyl-4-hydroxyphenyl)-
propionyloxy)-ethyl group and in particular R42 is a hydrogen atom or a methyl group, such as 2,6-jethyl-2,3,6-trimethylpiveridine, 2,2,6,6-tetra Methylpiveridine or 1,2,2,*6,6-bentamethylpiveridine is mentioned. R38 and R4. When represents an ethyl group, R
37 particularly represents a methyl group. R38 and R4. When represents a methyl group, R37 particularly represents a hydrogen atom. The following formula side: [In the formula, Me, p, q, r, s and L represent the above-mentioned preferred meanings, and R43 and R44 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, or an aralkyl group. R45 and R46 each independently represent an alkyl group, R47 represents an alkyl group, and R represents an alkyl group, phenyl group, benzyl group or phenethyl group, or R47 and R48 formed together Represents a tetramethylene group or a pentamethylene group, R49 is a hydrogen atom, oxyl group, alkyl group, alkenyl group, alkynyl group, alkoxyalkyl group, aralkyl group, 2,3-epoxypropyl group, alkoxycarbonylmethyl group, alkenyloxycarbonyl Methyl group, phenoxycarbonylmethyl group, aralkoxycarbonylmethyl group, cyclohexyloxycarbonylmethyl group, 2-hydroxyethyl group, 2-hydroxyph.

Lopyl group, 2-phenyl-2-hydroxyethyl group,
represents a 2-acyloxyethyl group, a 2-acyloxypropyl group, or a 2-phenyl-2-acyloxyethyl group, and when q represents 1, R5o is an optionally substituted ethylene group, an o-phenylene group, an optionally substituted represents a 1,3-propylene group, and when q represents 2, R5o represents the following formula: (CH)2C(CH21
)2・(CH2)2CR book-C ratio-○-R5, -CH2
-CR53(CH2-)2.(In the formula, R5 represents a divalent acyl group, and R53 represents a hydrogen atom, a methyl group, or an ethyl group.

) represents a group represented by A metal rust body represented by the following is also preferred. The alkyl radicals R43 and R44 preferably have 1 to 5 carbon atoms, such as the methyl radical.

Alkenyl R43 and R44, like allyl, in particular have 3 to 4 carbon atoms. Alkynyl groups R43 and R
44 particularly has 3 to 4 carbon atoms, such as a propargyl group.
has. The aralkyl radicals R43 and R44 preferably have 7 to 8 carbon atoms, like the penzyl radical. The alkyl radicals R45 and R46 preferably have 1 to 6 carbon atoms, such as methyl or ethyl. The alkyl group R47 particularly has 1 to 6 carbon atoms, such as a methyl group or an ethyl group.
has. Alkyl R48 especially has 1 to 9 carbon atoms, such as methyl or ethyl. The alkyl plug 49 specifically has 1 to 8 carbon atoms, such as a methyl group. The alkenyl group R49 especially has 3 to 6 carbon atoms, such as the propargyl group. Alkoxyalkyl group R
The group preferably has 2 to 21 carbon atoms, in particular 2 to 12 carbon atoms, such as the 2-methoxyshetyl group. The aralkyl group R49 particularly has 7 to 8 carbon atoms, such as a penzyl group, and the alkoxycarbonylmethyl group R49 particularly has 1 to 12 carbon atoms in the alkyl moiety, such as a methoxycarbonylmethyl group. The alkenyloxycarbonylmethyl group R49 particularly has 3 to 6 carbon atoms in the alkenyloxy moiety, like the allyloxycarbonylmethyl group. The aralkoxycarbonylmethyl group R49 particularly has 7 to 8 carbon atoms in the aralkoxy moiety, like the penzyloxycarbonylmethyl group. 2-acyloxyethyl group, 2-acyloxypropyl group and 2-phenyl-2-acyloxyethyl group R49 are acyloxy groups such as the following aliphatic, aromatic,
with acyloxy groups having up to 18 carbon atoms, such as araliphatic or cycloaliphatic anloxy groups; e.g. alkanoyloxy groups such as acetoxy; e.g. 3,5-di-tert-butyl-4-hydroxybenzoy; A penzoyloxy group optionally substituted with a chlorine atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, and/or a hydroxy group, such as a hydroxyl group: 8
-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionyloxy group in which the phenyl moiety is a chlorine atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, and A penzylcarbonyloxy group or a phenethylcarbonyloxy group which may be substituted with/or a hydroxyl group; a cyclohexylcarbonyloxy group.

The optionally substituted ethylene R5o is particularly of the formula:
-CR52R group -CHR54- (in the formula, R52 is a hydrogen atom, a methyl group, an acyloxymethyl group, an alkoxymethyl group having 1 to 4 carbon atoms in the alkoxy moiety, an alkenyloxymethyl group having 2 to 4 carbon atoms in the alkyloxy moiety) R53 represents a hydrogen atom, a methyl group or an ethyl group, and R54 represents a hydrogen atom, a methyl group or an ethyl group.

) represents a group represented by The acyl radical in acyloxymethyl represents an aliphatic, cycloaliphatic, aromatic or araliphatic acyl radical having up to 18 carbon atoms, in particular an aliphatic, cycloaliphatic, aromatic or araliphatic acyl radical, such as an acetyl radical; a cycloalkylcarbonyl radical; group; a penzoyl group optionally substituted with a halogen atom, a C1-C4 alkyl group and/or a hydroxyl group such as 3,5-di-tert-butylhydroxybenzoyl; 8-(
3,5-di-tert-butyl-4-hydroxyphenyl)-
Aralkylcarbonyl groups, especially those having 7 to 8 carbon atoms, in which the aryl moiety is optionally substituted with a chlorine atom, an alkyl group of 1 to 4 carbon atoms and/or a hydroxy group, such as propionyl. The optionally substituted carbamoyloxymethyl group particularly includes an alkyl group having 1 to 12 carbon atoms such as a methyl group, an aralkyl group having 7 to 8 carbon atoms such as a cyclohexyl group, a benzyl group, and a phenyl group. represents a group substituted with an N-mono-substituted aryl group having 6 to 12 carbon atoms, such as

an optionally substituted 1,3-propylene group R5o
In particular, the following formula: 1 CHR 1 CH2 1 CR53R54 1 CHR53-CH2 1 CR52R Koichi, 1 CH2 1 CR
521R group - CHR541 (in the formula R52, R53 and R
54 represents the above meaning.

). The divalent acyl group 5, is particularly carbonaceous, such as an aliphatic, aromatic or araliphatic dicarboxylic acid, such as an alkylene dicarbonyl group (e.g. malonyl or ethylene dicarbonyl group), a phenylene dicarbonyl group or a phenylene dimethyl carbonyl group. or R5. has up to 12 atoms or has the formula: -CON-alkylene-NHCO-, where the alkylene radical has in particular 2 to 8 carbon atoms, such as the ethylene radical or the 1,4-butylene radical.

) or of the following formula: -CONH-arylene-NHC◯ (wherein the arylene group, like the phenylene group, particularly has 6 to 12 carbon atoms.

) or -CONH-xylylene-NHCO- or -
CONH-C6 represents the -CH2-C6 ratio -NHCO-.

Preferably, R43 represents a hydrogen atom, R44 represents a hydrogen atom or a methyl group, R45 represents a methyl group, R paper and R48 represent a methyl group or an ethyl group, and R49 represents a methyl group or an ethyl group. Represents a hydrogen atom or a methyl group, q represents 1 or 2, and when q represents 1, R rice is an ethylene group, methylethylene group, or hydrogen.

oxymethylethylene group, acyl moiety has 2 to 1 carbon atoms
an acyloxymethylethylene group having 2, in some cases an alkyl group in which the penzoyl moiety has 1 to 4 carbon atoms,
and/or a penzoyloxymethylethylene group substituted with a hydroxyl group, B-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionylmethylethylene group, 1,3- Propylene group, 2-methyl-1,3-
Propylene group or 2-ethyl-1,3-propylene group (all of these propylene groups have a methyl group, hydroxymethyl group, or acyloxymethyl group having 2 to 12 carbon atoms at the 2-position, and a carbon atom at the benzyl moiety) A penzoyloxymethyl group which may be substituted with a number 1 to 4 alkyl group and/or a hydroxyl group: or a 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionyloxymethyl group. ),
When q represents 2, R5o is (1CH2)2C(CH
2-) A compound representing 2, for example 8-other 6,
7,9-trimethyl-7,9-diethyl-1,4-dioxaspiro[4,5]-decane, 8-aza-7,7,9
,9-tetramethyl-1,4-dioxaspiro[4,5
] Decane or 9-other 8,8,10,10-tetramethyl-1,5-dioxaspiro[5,5]undecane. When R46 and R48 represent an ethyl group, R44 particularly represents a methyl group.

When R46 and R48 represent a methyl group, R44 particularly represents a hydrogen atom. The next most preferred metal anchor is represented by the following formula represents an alkynyl group or an aralkyl group, R57 and R58 each independently represents an alkyl group, R represents an alkyl group, phenyl group, benzyl group or phenethyl group, R6o represents an alkyl group, or R59 represents R6.

R6 represents a hydrogen atom, an oxyl group, an alkyl group, an alkenyl group, an alkoxyalkyl group, or an aralkyl group, and R62 represents a hydrogen atom, an alkyl group, or an alkenyl group. , propargyl group, aralkyl group, -CH2COOR63 or -CH2CH2COOR63
{In the formula, R63 is an alkyl group, phenyl group, benzyl group, or cyclohexyl group, or -CH2CH(Rscale)OR
(In the formula, R represents a hydrogen atom, a methyl group, or a phenyl group, and R represents a hydrogen atom or an acyl group.)
represents a group. ]. Alkyl R55 and R5
6 particularly has 1 to 5 carbon atoms, such as a methyl group.

Alkenyl R55 and R56, like allyl, in particular have 3 to 4 carbon atoms. Alkynyl groups R55 and R
56 particularly has 3 to 4 carbon atoms, such as a propargyl group.
has. The aralkyl radicals R55 and R56 preferably have 7 to 8 carbon atoms, like the penzyl radical. The alkyl radicals R57 and R58 in particular have 1 to 6 carbon atoms, such as methyl or ethyl. The alkyl group R59 particularly has 1 to 9 carbon atoms, such as a methyl group or an ethyl group.
has. The alkyl group R6o has in particular 1 to 6 carbon atoms, such as a methyl or ethyl group. Alkenyl group R6. has especially 3 to 6 carbon atoms, such as allyl. Alkoxyalkyl radicals 6, like the 2-methoxyshetyl group, preferably have 2 to 21 carbon atoms, especially 2 to 12 carbon atoms. The aralkyl group R6, like the penzyl group, in particular has 7 to 8 carbon atoms. The alkyl group R62 particularly has 1 to 1 carbon atoms, such as a methyl group.
It has 2. The alkenyl group R62, like the allyl group, in particular has 3 to 6 carbon atoms. The aralkyl group R62, like the penzyl group, in particular has 7 to 8 carbon atoms.
The alkyl group R63 especially has 1 carbon atom, such as a methyl group.
to 8. Acyl group R65 is an alkanoyl group such as an acetyl group or a propionyl group, a chlorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms in some cases, such as a 3,5-di-tert-butyl-4-hydroxybenzoyl group. a penzoyl group optionally substituted with 1 to 8 alkoxy groups and/or hydroxyl groups, 8-(3,5
-The phenyl moiety is substituted with a chlorine atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, and/or a hydroxy group, as in the case of -di-tert-butyl-4-hydroxyphenyl)propionyl group. In particular, the acyl group may have up to 18 carbon atoms, such as an aliphatic, aromatic, araliphatic or cycloaliphatic acyl group, such as a pendylcarbonyl group or a phenethylcarbonyl group. Preferably, in the complex represented by formula K, R55 represents a hydrogen atom, R represents a hydrogen atom or a methyl group, R57 and R59 represent a methyl group or an ethyl group, and R59 and R represent a methyl group. , R6, represents a hydrogen atom, an oxyl group, or an alkyl group having 1 to 4 carbon atoms, and R
62 is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms,
Allyl group, benzyl group, alkoxycarbonylmethyl group having 1 to 8 carbon atoms in the alkoxy moiety, alkylcarbamoyl group having 1 to 12 carbon atoms in the alkyl moiety, phenylcarbamoyl group, chlorophenylcarbamoyl group , a methylphenylcarbamoyl group, a benzylcarbamoyl group, or a cyclohexylcarbamoyl group.

In particular, R55 represents a hydrogen atom, R56 represents a hydrogen atom or a methyl group, R57 and R59 represent a methyl group or an ethyl group, R58 and R6. represents a methyl group, and R6. represents a hydrogen atom or a methyl group, R6
2 is a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an allyl group, a benzyl group, and an alkyl moiety having 1 to 12 carbon atoms
A compound having an alkylcarbamoyl group, phenylcarbamoyl group or cyclohexylcarbamoyl group, such as 2,7-diethyl-2,3,7-trimethyl-1,4-diaza-5-oxocyclohebetane, 2
, 2,7,7-tetramethyl-1,4-diaza-5-oxocyclohebutane or 1,2,2,7,7-bentamethyl-1,4-diaza-5-oxocyclohebutane. When R57 and R59 represent an ethyl group, R represents in particular a methyl group. R57 and R5
When 9 represents a methyl group, R56 particularly represents the number of hydrogen atoms. In addition, the following formula , R68, R69 and R7o each independently represent an alkyl group, and R7 represents an alkyl group, phenyl group, benzyl group or phenethyl group, or R7.

and R7,1 represent a tetramethylene group or a pentamethylene group formed together, and the R flower represents a hydrogen atom, an oxyl group, an alkyl group, an alkenyl group, an alkoxyalkyl group, an aralkyl group, an alkoxycarbonylmethyl group, an alkenyloxycarbonylmethyl group. group, phenoxycarbonylmethyl group, aralkoxycarbonylmethyl group, cyclohexyloxycarbonylmethyl group or mono-C-CH
(R76) represents an OR77 (in the formula, R76 represents a hydrogen atom, a methyl group, or a phenyl group, and R77 represents a hydrogen atom or an acyl group), and R73 represents a hydrogen atom, a methyl group, a phenyl group, or a vinyl group. , R7d and R75 each independently represent a hydrogen atom, methyl group, phenyl group, vinyl group, alkoxy group, alkoxyalkoxy group, cyclohexyloxy group, aralkoxy group, aryloxy group, 1-R72-2-R68-2 1R spot-3-R
66-5-R67-6-R7. -61R7,14-piveridyloxy group (R72, R spot, R69, R56, R6
7, R7o, R7· represent the above meanings. ),
When R and R74 represent a hydrogen atom, a methyl group, a phenyl group, or a vinyl group, R75 can be represented by the following formula: (wherein m represents an integer from 1 to 10, R66, R, R6
8, R69, R7o, R? ,,R72,Rne,R74 represent the above meanings.

) represents a group represented by ] Also preferable is a metal coin body. The alkyl radicals R66 and R67 preferably have 1 to 5 carbon atoms, like the methyl radical.

The alkenyl radicals R66 and R67, like the allyl group, in particular have 3 to 4 carbon atoms. The alkynyl radicals R66 and R67 preferably have 3 to 4 carbon atoms, like the propargyl radical. Aralkyl radicals R66 and R67, like penzyl radicals, in particular have 7 to 8 carbon atoms. The alkyl radicals R68, R69 and R7o preferably have 1 to 6 carbon atoms, such as methyl or ethyl. Alkyl radicals R7, in particular have 1 to 9 carbon atoms, such as methyl or ethyl radicals. The alkyl group R72, like the methyl group, in particular has 1 to 12 carbon atoms. The alkenyl group R72, like the allyl group, in particular has 3 to 6 carbon atoms. The alkoxyalkyl group R72 in particular has 2 to 14 carbon atoms, such as the 2-methoxyethyl group. Aralkyl group R72 especially has 7 carbon atoms, such as penzyl group.
8. Alkoxycarbonylmethyl group R cedar has particularly 1 to 8 carbon atoms in the alkoxy moiety, like methoxycarbonylmethyl group. Alkenyloxycarbonylmethyl group has 3 to 6 carbon atoms in the alkenyloxy moiety, such as allyloxycarbonylmethyl group.
has. The aralkoxycarbonylmethyl group R72 particularly has 7 to 8 carbon atoms in the aralkoxy moiety, like the penzyloxycarbonylmethyl group. Acyl group R77
is an alkanoyl group such as an acetyl group or a propionyl group,
For example, 3,5-di-tert-butyl-4-hydroxybenzoyl may optionally contain a chlorine atom, a C1-C4 alkyl group, a C1-C8 alkoxy group, and/or a hydroxyl group. Substituted penzoyl group, 8-(3,5-di-tert-butyl-4-hydroxy-
(phenyl)-propionyl group, which may optionally be substituted with a chlorine atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, and/or a hydroxyl group; groups, especially those having up to 18 carbon atoms, such as aliphatic, aromatic, araliphatic or cycloaliphatic acyl groups, such as the cyclohexylcarbonyl group. Alkoxy radicals 74 preferably have 1 to 8 carbon atoms, such as methoxy groups. The alkoxyalkoxy radicals R74 and R75 preferably have 3 to 10 carbon atoms, such as the 2-methoxyshethoxy radical. Aralkoxy R7Z skin R75 preferably has 7 to 8 carbon atoms, such as penzyloxy or phenethyloxy. The aryloxy radicals R74 and R75 represent in particular a phenoxy radical optionally substituted with a chlorine atom, a C1-C4 alkyl group or a C1-C4 alkoxy group. In the chain of formula ×, preferably,
R66 represents a hydrogen atom, R represents a hydrogen atom or a methyl group, R68 and R7.

represents a methyl group or an ethyl group, R69 and R7,
represents a methyl group, R72 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R73 and R74 represent a methyl group or a phenyl group, and R75 represents a methyl group, a phenyl group or a 1-R72-2- R68-2
-Methyl-5-R67-6-R? It is a compound representing an o-6-methyl-4-piveridyloxy group (R67, R68, R7. and R flower represent the above meanings). Particularly preferably R66 represents a hydrogen atom, R67 represents a hydrogen atom or a methyl group, R68 and R7. represents a methyl group or an ethyl group, R69 and R7 represent a methyl group, R72 represents a hydrogen atom or a methyl group,
R73 and R74 represent a methyl group or a phenyl group, and R75 represents a methyl group, a phenyl group or 1-R7
2-2-R68-2-methyl-5-R67-61R7.
-6-methyl-4-piveridyloxy (R67, R68
, R7. and R72 represent the above meanings. ) group, such as '2,2,6,6-tetramethyl-4-trimethylsiloxypiveridine, diphenylbis(2,2
, 6,6-tetramethylpiveridine-4-oxy)-silane, dimethyl-bis(2,2,6,6-tetramethylpiveridine-4-oxy)-silane or 1,2,2,
6,6-pentamethyl-4-triphenylsiloxypiveridine is mentioned. R68 and R7. When represents an ethyl group, R67 particularly represents a methyl group. R68 and R7. When represents a methyl group, R67 particularly represents a hydrogen atom. The complexes according to the invention optionally also contain various stereoisomers which are also the subject of the invention.

In the synthesis of the collar body of the present invention, a mixture of stereoisomers is obtained.

In particular, the starting material may already be a mixture of stereoisomers. Such mixtures can be separated, if necessary, at a given stage of the synthesis in a manner known per se. Among the preferred metal complexes, particularly preferred are those in which Me represents zinc, cobalt and especially nickel, r represents 1 or 2, and q
represents 1 or 2, p represents 1, and s represents 0 to 2
and L represents a monovalent anion of an alkanecarboxylic acid having 1 to 12 carbon atoms or a monovalent anion of an phenol corresponding to the above-mentioned formula B, in particular an anion of acetylacetonate; It is a compound represented by

Preference is also given, however, to those compounds in which Me represents a trivalent cation, ie aluminum or chromium, and the other symbols have the meanings given above.

The metal flange body expressed by the formula (1) is expressed by the formula (blood) Mew■L
We (kari) (where Me, w and L represent the above.

) or its hydrate represented by the formula (Kari) (
In the formula, R,, R2, R3, R4, X and Y represent the above.

) or a hydrate thereof. Preferably, about r mol of the metal compound willow and about p mol of the amine plate are used.

The reaction is carried out by dissolving the two reactants together, especially in stoichiometric proportions, in an inert solvent and then removing the solvent, for example by evaporation. Suitable solvents include in particular the following inert organic solvents: hydrocarbons such as kerosene, cyclohexane, benzene, toluene, xylene; chlorinated hydrocarbons such as chloroform; ketones such as acetone, methyl ethyl ketone; esters such as ethyl acetate; ethers such as dioxane. , tetrahydrofuran, ethylene glycol dimethyl ether,
Dimethylene glycol dimethyl ether, ethylene glycol monomethyl ether or ethylene glycol monoethyl ether; alcohols, alkanols such as methanol, ethanol or isopropanol; nitrites such as acetonitrile or mixtures of these solvents.

An inert solvent is one that is inert especially under the reaction conditions.

The formula plates and starting materials designated by Xm are known and in many cases commercially available, but if one or the other of these is new, they are prepared in a manner known per se.

Thus, for example, 1-4-oxopiveridine with various substituents at the 2- and 6-positions is a ketone R, 1CO-
It can be produced by reacting R2 with ammonia.

The pyrimidine formed is Helvetic acid compound (He
lv. Chim. Acta) 30, 114 (1947)
is hydrolyzed to the r-aminoketone as described in
(Monash.C
hemje) 88464 (1957)]. It is then hydrolyzed to produce the desired NH compound, which can be used as a starting material for various amines of the formula. For example, for piveridine as obtained by formula m, 2,6-dimethyl-2,6-di-R,o-3-R, . -4-oxopiveridine; 2-methyl 2-R,2-3-R,5-4-oxo-
6-R, 3-6-R, 4-piveridine; 2-R2, 2-R2, 3-R, 9-4-oxo-5-R number- 61R Genichi 61R
Pine-piveridine; 2-R29-2-R3 for piveridine as obtained by the formula. -3-R27-4-oxo 5-R29-6-R31 one dose 32-piverizine; 2R4o-2
-R4,-3-R37-4-oxo5-R36-6-R38-6-R39-piveridine; 2-R for piveridine as obtained by shikikei 2-RKyo-13-R4
3-4-Oxo5-R44-61R47-61R48
- Piveridine; 2-R57-2-R58-3-R55-4-oxo-5 for amines such as those obtained with formula K;
-R56-6-R59-6-R6o-piveridine (all symbols of R in the above formula represent the above meanings). Further modification of each of these intermediates can be carried out in a manner similar to that of the sterically hindered amines first described in the prior art.

The metal chains of formula 1 according to the invention can protect many organic polymers from damage caused by light, and at the same time they have excellent extraction stability and compatibility with polymeric substrates.

Examples of polymers to be stabilized in this manner include the following. 1 mono- and diolefin polymers;
For example, polyethylene (which may be crosslinked depending on the case).

), polypropylene, polyisobutylene, polymethylbutene-1, polymethylbentene-1, polyisoprene or polybutadiene. Mixture of polymers described in 21:
For example mixtures of polypropylene with polyethylene or polyisoptylene.

3 mono- and diolefin copolymers; for example, ethylene-propylene copolymers, propylene-butene-1 copolymers, propylene-isobutylene copolymers, ethylene-butene-1 copolymers, and ethylene, propylene, and hexadiene. , dicyclobentadiene, or terpolymers with diene such as ethylidene norbornene.

4 polystyrene.

Copolymers of 5-styrene or methylstyrene and diene or acrylic derivatives, such as styrene-butadiene, styrene-acrylonitrile, styrene-acrylonitrile-methylacrylate copolymers; styrene copolymers and polyacrylates, diene polymers or ethylene- A high impact mixture consisting of a block copolymer of styrene with another polymer such as a propylene-diene terpolymer; a block copolymer of styrene such as styrene-butadiene-styrene, styrene-isobrene-styrene or styrene-ethylene/butylene-styrene. Block copolymer.

6. Graft copolymers of styrene, such as styrene to polybutadiene, styrene and acrylonitrile graft copolymers to polybutadiene, and mixtures with the copolymers described under 5, such as are known as so-called ABS polymers.

7 Polyurethane and polyurea.

The compound of formula 1 is incorporated into the substrate in a concentration of 0.005 to 5% by weight, calculated based on the substance to be stabilized.

Preferably from 0.01 to 1.0% for the substance to be stabilized. Particularly preferably from 0.02 to 0.5% by weight
A compound of the invention is incorporated into this material at a concentration of .

Incorporation involves incorporating at least one compound of formula 1 and optionally further additives into the melt before or during molding, or by melting or This can be done by applying the dispersed compound to the polymer, optionally followed by evaporation of the solvent. The compounds of formula 1 can be added before or during the polymerization, so that as a result of possible incorporation into the polymer chain a stabilized matrix is obtained in which the stabilizer is not volatile and cannot be extracted.

However, the addition can also be carried out by incorporating the components of the formula and Xm into the substrate, in particular using the anhydrous form of the components of the formula and Xm. In this case, the symbols in Shikiyanagi and Xm represent the meanings described above as particularly preferred. The invention therefore also relates to a process for photostabilizing organic polymers using compounds of formula (1) as photostabilizers for organic polymers.

In particular, it is possible to preferably use the broadly described components consisting of a collar body, the components specifically described above, and the complex components described in the Examples.

The proportions of compounds of Formula 1 and Xm are chosen, although not necessarily, to match the rust body of Formula 1. Fine: The mol% ratio of Xm is 0.1:99.9 to 99.9:0.1
is suitable, especially a ratio of 1:99 to 99.9:0.1, especially 1:99. The ratio is between 80:20 and particularly preferably between 5:95 and 70:30. Such stabilizer mixtures can be used as described for compounds of formula 1, in particular in amounts of 0.01 to 5% by weight, based on the polymer to be stabilized.
Below are further examples of additives which can be used together with the stabilizers and stabilizer mixtures according to the invention.

1 Antioxidants (examples are listed below).

)1.1 Simple 2,6-dialkylphenols 2,6
-Di-tert-butyl-4-methylphenol 2-tert-butyl-4,6-dimethylphenol-2,6-dibutyl-4-methoxymethylphenol 2,6-dioctadecyl-4-methylphenol 1.2 Alkylated hydroquinone derivatives 2,5-di-tert-butyl-hydroquinone 2,5-di-tert-mil-hydroquinone 2,6-di-tert-butyl-hydroquinone 2,5-di-tert-butyl -4-hydrocyanisole 3,5-di-tert-butyl-4-hydrocyaniso-norephosphite-tris(3,5-di-tert-butyl-4-hydroxycyphenyl) 3,5-di-tert stearate Butyl-4-hydroxyphenyladipate-bis-(3,5-di-tert-butyl-4-hydroxyphenyl) 1.3 Hydroxylated thiodiphenyl ethers 2,2-thiobis-(6-tert-butyl-4-hydroxyphenyl) -methylphenol) 2,2'-thiobis(4-octylphenol) 4,4'-thiobis(6-tert-butyl-3-methylphenol) 4,4'-thiopis(3,6-di-secondary amylphenol) 4 ,4'-thiobis-(6-tert-butyl-2-methylphenol) 4,4'-bis(2,6-dimethyl-4-hydroxyphenyl)-disulfide 1,4-alkylidene-bisphenols 2,2-methylenebis- (6-tert-butyl-4-methylphenol) 2,2'-methylenebis-(6-tert-butyl-4-ethylphenol) 4,4-methylenebis-(6-tert-butyl-2-methylphenol) 4, 4-Methylenebis-(2,6-di-tert-butylphenol) 2,6-di(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol 2,2'-methylenebis-[4-methyl -6-(Q-methylcyclohexyl)-phenol] 1,1-bis-(3,5-dimethyl-2-hydroxyphenyl)-butane 1,1-bis-(5-tert-butyl-4-hydroxy- 2-Methylphenyl)-phthane 2,2-bis-(5-tert-butyl-4-hydroxy-2-methylphenyl)-phthane 2,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)- Propane 1,1,3-tris(5-tert-butyl-4-hydroxy-2-methylphenyl)-butane 2,2-bis-(5-tert-butyl-4-hydroxy-2-methylphenylphenyl)-4 -n Dodecylmercabutophthane 1,1,6,5-tetra-(5-tert-butyl-4-hydroxy-2-methylphenyl)-pentaneethylene glycose-bis[3,3-bis-(3'-tert. Butyl-4'-hydroxy-phenyl)-butyrate] 1.50 1,N- and S-penzyl compounds 3,5,3,5'-tetratert-butyl-4,4
-dihydroxydibenzyl ether-7 Nore-4-hydroxy-3,5-dimethylbenzyl-mercaptoacetic acid-octadecyl ester tri-(3,5-di-tert-butyl-4-hydroxybenzyl)-aminebis-(4-tert-butyl-3 -Hydroxy-2,6-dimethylbenzyl)-dithiol terephthalate 1.6 hydroxybenzylated malonic acid esters 2,2
-bis-(3,5-di-tert-butyl-2-hydroxybenzyl)-malonic acid-dioctadecyl ester 2-(3-tert-butyl-4-hydroxy-5-methylbenzyl)-malonic acid-dioctadecyl ester 2 ,2-bis-(3,5-di-tert-butyl-4-hydroxybenzyl)-malonic acid-didodecylmercaptoethyl esteth 2,2-bis-(3,5-di-tert-butyl-4-hydroxybenzyl) -malonic acid-di[4-(1,1,3,3-tetramethylbutyl)-phenyl]-estenole 1.7 hydroxybenzyl-aromatic compound 1,3,5-
tri(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6,-trimethylbenzene1,4-di(3,5-di-tert-butyl-4-hydroxybenzyl)-2,3, 5,6-tetramethylbenzene 2,4,6-tri-(3,5-di-tert-butyl-4-hydroxybenzyl)-phenol 1.8S-triazine compound 2,4-bis-octylmercapto-6 (3,5-di-tert-butyl-4-hydroxyanilino)-s-triazine 2-octylmercapto-4,6-bis-(3,5-tert-butyl-4-hydroxyanilino)-s-triazine 2-octylmercapto Pto-4,6-bis-(3,5-di-tert-butyl-4-hydroxyphenoxy)-s-triazine 2,4,6-tris-(3,5-di-tert-butyl-4-hydroxyphenoxy) -S triazine 2,4,6-tris-(3,5-di-tert-butyl-4-hydroxyphenylethyl) -s-triazine 1,3,5-tris(3,5-di-tert-butyl -4-hydroxybenzyl)-isocyanurate 1.96-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionic acid amides 1,3,5-tris(3,5-di-tert-butyl- 4-Hydroxyphenylpropionyl)-hexahydro-s-triazine N,N'-di(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)-hexamethylenediamine 1.103-(3,5 -di-tert-butyl-4-hydroxyphenyl)-propionic acid and a monohydric or polyhydric alcohol (only the names of alcohols forming the estes are exemplified) methanol, ethanol, octadecanol, 1,6-
Hexanediol, 1,9-/nanediol, ethylene glycol, 1,2-pro/andiol, diethylene glycol, thiodiethylene glycol, neobentyl glycol, bentaerythritol, 3-thiaundecanol, 3-thiabentadecanol , trimethylhexanediol, trimethylolethane, trimethylolpro/gum, tris-hydroxyethyl isocyanurate, 4-hydroxymethyl-1-phosphor 2,6,
7-trioxapicyclo[2,2,2]-octane 1.
116 Ester of -(5-tert-butyl-4-hydroxy-3-methylphenyl)-propionic acid and monohydric or polyhydric alcohol (only names of alcohols forming esters are exemplified) Methanol, ethanol, octadecanol, 1, 6-
Hexanediol, 1,9 nonanediol, ethylene glycol, 1,2-propanediol, diethylene glycol, thiodiethylene glycol, neobentyl glycol, bentaerythritol, 3-thiaundecanol, 3-thia-pentadecanol, trimethylhexanediol , trimethylolethane, trimethylolpropane, tris-hydroxyethyl isocyanurate, 4-hydroxymethyl-1-phosphor 2,6,7-
trioxabicyclo[2,2,2]-octane 1.12
Esters of 3,5-di-tert-butyl-4-hydroxyphenylacetic acid and monohydric or polyhydric alcohols (only alcohol names forming estes are exemplified): methanol, ethanol, octadecanol, 1,6-hexanediol, 1,9 nonanediol, ethylene glycol, 1,2-propanediol, diethylene glycol, thiodiethylene glycol, neobentyl glycol, bentaerythritol, 3-thiaundecanol, 3-thiabentadecanol, trimethylhexanediol, Trimethylolethane, trimethylolpro/gun, tris-hydroxyethyl isocyanurate, 4-hydroxymethyl-1-phosphor 2,6,7
-trioxabicyclo[2,2,2]-octane 1.1
3-Acylaminophenols N-(3,5-di-tert-butyl-4-hydroxyphenyl)-stearamide N,N'-di(3,5-di-tert-butyl-4-hydroxyphenyl)-thiobis- Acetamide 1.14 Penzylphosphonic acid estethic acid 3,5-di-tert-butyl-4-hydroxybenzyl-phosphonic acid dimethyl este/3,5-di-tert-butyl-4-hydroxybenzyl-phosphonic acid estethenolate 3 , 5-di-tert-butyl-4-hydroxybenzyl-phosphonic acid dioctadecyl ester 5-tert-butyl-4-hydroxy-3-methylbenzyl-phosphonic acid dioctadecyl ester 1.15 spiro compound 3,9-bis-(3 , 5-di-tert-butyl-4-hydride.

xyphenyl)-2,4,8,10-tetraspiro[5
,5]undecane 3,9-bis[1,1-dimethyl-2(3,5-di-tert-butyl-4-hydroxyphenyl)-ethyl]-2,4,8,10-tetraspiro[5,5]undecane 1.16 Aminoaryl conductor Phenyl-1 naphthylamine Phenyl-2 naphthylamine N,N'-diphenyl-p-phenylenediamine N,N'-di-2-naphthyl-p-phenylesodiamine N,N'- Di-sec-butyl-p-phenylenediamine 6-ethoxy-2,2,4-trimethyl-1,2-dihydroquinoline monooctyliminodibenzyl and dioctyliminobenzyl 2,2,4-trimethyl-1,2-dihydroquinoline Polymer octylated diphenylamine nonylated diphenylamine N-phenyl-N'-isopropyl-p-phenylenediamine N,N'-di-sec-octyl-p-phenylenediamine N-phenyl-N'-sec-octyl-p-phenylenediamine N,N '-dimethyl(1,4-dimethylbentyl)-p-phenylenediamine N,N'-dimethyl-N,N'-di(sec-octyl)-
p-phenylenediamine 2,6-dimethyl-4-methoxyaniline 4-ethoxy-N-sec-butylaniline Condensation product of diphenylamine and acetone Aldol-1-naphthylamine Phenothiazine 2 Ultraviolet absorbers and light stabilizers e.g. 1(2'-hydroxyphenyl)-benzotriazole, 2,4-bis. (2'-Hydroxyphenyl)-6-alkyl-s-triazine, 2-hydroxybenzophenone, optionally substituted benzoic acid ester, acrylate, oxalic acid diamide, 3 metal deactivator 4 phosphite 5 week oxide decomposition Agent 6 Basic co-stabilizer 7 Nucleating agent 8 Other additives such as lubricant, filler, carbon black, asbestos, kaolin, talc, glass fiber, pigment, crab optical brightener, flame retardant, antistatic agent .

The use of stabilizers or stabilizer mixtures of formula 1 together with the above-mentioned antioxidants is particularly effective in polyolefins.

Next, examples of the present invention will be shown, but these are not intended to limit the present invention in any way.

Examples 1 to 39 The following general methods are suitable for obtaining these compounds.

The sterically hindered amine and the metal compound of formula Mew were dissolved in a solvent that is inert and sufficiently effective for these components and the final product. If necessary, heat the mixture until a homogeneous solution is obtained. The mixture was then briefly refluxed and the solvent was distilled off under a pressure of 11 feet Hg. When choosing a solvent, it is important that either of the two components to be dissolved precipitates out due to insufficient solubility during the subsequent evaporation of the solvent mixture, resulting in a ternary body of general formula 1. Particular care should be taken to ensure that they are not excluded from the equilibrium formation of The residue was then dried under conditions such that the amine component could not volatilize. The examples defined in columns 1 to 4 in Table 1 were combined with appropriate solvents, reaction conditions (column 5) and drying conditions (column 6).
showed that.

Column 7 describes the properties of the final product obtained.

ship fence Guidance vertical earth Selection ship skin key ■ pond lotus Satoshi Table 1 (continued) *The amine component is shown here as a number from 1 to 8.

The meanings of these abbreviations are listed in Table 2 below. **"solubility"
represents the solubility of the final product in the stated solvent; plus and minus have the following meanings:

A substance becomes a solution at room temperature. (10) A substance becomes a solution only when heated.

One substance does not dissolve significantly. ＊＊＊“Regroin”=
Oil crab boils at 110 to 140 oo.

○ required to obtain the compounds of Examples 19, 20 and 53
-The nickel isomer of methoxyacetoacetic acid anilide can be produced in the same manner as the nickel-ro-8-ketoamine complex [Inorganic Synthesis (lno
rg. Synthesis, volume 11, page 72].

Table 2 Example 59 1000 parts of polypropylene powder (melt index at 23 and 0, 10 min., 2160 min.) were mixed in a drum mixer with pentaerythrittatetetrakis [3-(3
',6-di-tert-butyl-4-hydroxyphenyl)-
propionate] and 2.5 parts of the nickel compound shown in Table W were mixed and then granulated in an extruder at a temperature of 200 to 22,000 °C.

The resulting granules were processed into sheets in the usual manner using an extruder with a slot die. The sheet was cut into ribbons and then heated to stretch to six times its length and wound onto a spool. Ribbon weave is 900 to 1000
Denier (den.) and their final tension is 5.5
to 6.5 tanodenier (den.). These polypropylene ribbons were attached without tension to the specimen carrier and irradiated in the xenotest apparatus 150. Five specimens were run at different times and their final tensions were measured.

The criteria for determining the protective effect of individual nickel compounds was expressed as the "protective factor" defined below. Light irradiation time until the stabilized sample loses its final tension of 50*Protection Factor - Irradiation time until the unstabilized sample loses its final tension of 50* The values obtained are listed in Tables m and W below.

Table M Table W Example 60 1000 parts of polypropylene powder (melt index 2.5g at 230o0, 2160%) was mixed with pentaerythrittatetetrakis [31(3',5'- 1 part of di-tert-butyl-4-hydroxy-phenyl)-propionate and 1.5 parts of the mixture of components 1 and 2 of Table V were mixed, and then 200 to 2
Granulation was carried out at a temperature of 30 oo.

The resulting granules were processed into sheets in the usual manner using an extruder with a slot die. The sheet was cut into ribbons and then heated to stretch to six times its length and wound onto a spool. Ribbon weave is 900 to 1000
Denier (den.) and their final tension is 5.5
6.5 to 6.5 denier (den.). These polypropylene ribbons were attached without tension to a specimen carrier and irradiated in a xenotest apparatus 1200. Five specimens were run at different times and their final tensions were measured.

The criteria for determining the protective effect of each nickel compound are expressed as the "protective factor" defined below. Light irradiation time until the stabilized sample reaches a final tension of 50* and is destroyed [1f.

Rotectebu factor - “Unstabilized sample has 50% final tension” Irradiation time until extinction The values obtained are listed in Table V below.

Table V

Claims (1)

[Claims] 1 Formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, Me represents magnesium, calcium, manganese, zinc, cobalt, nickel, chromium, or aluminum, and w represents 2 or 3, p represents 1 or 2, r represents 1 or 2, s represents a numerical value of 0 to 2, R_1, R_2, R_3 and R_4 each independently represent an alkyl group, Y is hydrogen, X represents an oxyl group or an alkyl group, and X represents the following group ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R'_8 represents hydrogen or an alkyl group, and R '_9 represents a monovalent aliphatic or aromatic residue, R'_1_0
represents a divalent aliphatic residue optionally substituted by a substituted phenyl group, R'_1_1 represents a monovalent aliphatic or aromatic residue, and R'_1_
2 represents an alkylene group which may be substituted with a hydroxyl group. ) represents a divalent residue that supplements the N-containing ring to become a 6-membered ring;
Valid anion, monovalent anion of aminophosphinic acid or aminophosphonic acid, or formula (II): ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (In the formula, Z represents an oxo group or an alkylimino group, R_5 represents an alkyl group, substituted alkyl group, aryl group or substituted aryl group, R_6 represents hydrogen or an alkyl group, or R_5 and R_6 taken together optionally substituted 1,4-butadi-1,3 −represents enylene;
And R_7 represents an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an alkoxy group, or a substituted amino group. ) represents a monovalent anion of enol. ]
A metal complex represented by 2 L represents formula (II) (Z represents an oxo group or an alkylimino group having 1 to 4 carbon atoms, R_5 represents an alkyl group having 1 to 12 carbon atoms, R_6 represents hydrogen, or R_5 and R_6
taken together are 1,4-butadi-1,3 optionally substituted by C1 -C12 alkyl, C1 -C12 alkoxy or halogen;
-enylene, and R_7 represents a C1-C12 alkoxy group, a C1-C12 alkyl group or a phenyl group. ) The metal complex according to claim 1, which is an enol represented by formula (I). Claim 2, wherein 3 L is an enolate ion of acetylacetone.
Metal complexes described in Section. 4. A metal complex according to claim 1, wherein w represents 2 and Me represents nickel. 5 The amine is bis-(2,2,6,6-tetramethyl-4-piperidyl)-sebacate, 2,2,6,6-tetramethyl-4-benzoyloxypiperidine, 3-n
-octyl-7,7,9,9-tetramethyl-1,3,
8-triazaspiro[4,5]decane-2,4-dione, 1,2,2,6,6-pentamethyl-4-stearoyloxypiperidine or n-butyl(3,5-di-tert-butyl-4- hydroxybenzyl)-malonate bis-(
Claim 1 represented by formula (I) which is 2,2,6,6-tetramethyl-4-piperidyl)-ester
Metal complexes described in Section. 6 As a light stabilizer for organic polymers, formula (I):
▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, Me represents magnesium, calcium, manganese, zinc, cobalt, nickel, chromium, or aluminum, w represents 2 or 3, p represents 1 or 2, r represents 1 or 2, S represents a numerical value of 0 to 2, R_1, R_2, R_3 and R_4 each independently represent an alkyl group, Y represents hydrogen, an oxyl group or an alkyl group, and X represents the following Group ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R'_8 represents hydrogen or an alkyl group, and R'_9 represents a monovalent aliphatic or aromatic residue. represents a group, R'_1_0
represents a divalent aliphatic residue optionally substituted by a substituted phenyl group, R'1_1 represents a monovalent aliphatic or aromatic residue, and R'_1_2
represents an alkylene group which may be substituted with a hydroxyl group. ) represents a divalent residue that supplements the N-containing ring to become a 6-membered ring;
valent anion, monovalent anion of aminophosphinic acid or aminophosphonic acid or formula (II) ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (In the formula, Z represents an oxo group or an alkylimino group, R_5 represents an alkyl group, a substituted alkyl group, an aryl group or a substituted aryl group, R_6 represents hydrogen or an alkyl group, or R_5 and R_6 taken together optionally substituted 1,4-butadi-1,3- represents enylene,
And R_7 represents an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an alkoxy group, or a substituted amino group. ) represents a monovalent anion of enol. ]
A method for stabilizing an organic polymer, characterized by using a metal complex represented by: 7 Formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, Me represents magnesium, calcium, manganese, zinc, cobalt, nickel, chromium, or aluminum, w represents 2 or 3, and p represents 1 or 2, r represents 1 or 2, s represents a numerical value of 0 to 2, R_1, R_2, R_3 and R_4 each independently represent an alkyl group, Y represents hydrogen, an oxyl group or an alkyl group. The expression,
R′_1_0 represents a divalent aliphatic residue optionally substituted with a phenyl group, R′_1_1 represents a monovalent aliphatic or aromatic residue; represents a group residue, and R′_1_2
represents an alkylene group which may be substituted with a hydroxyl group. ) represents a divalent residue that supplements the N-containing ring to become a 6-membered ring;
Valid anion, monovalent anion of aminophosphinic acid or aminophosphonic acid, or formula (II): ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (In the formula, Z represents an oxo group or an alkylimino group, R_5 represents an alkyl group, substituted alkyl group, aryl group or substituted aryl group, R_6 represents hydrogen or an alkyl group, or R_5 and R_6 taken together optionally substituted 1,4-butadi-1,3 −represents enylene;
And R_7 represents an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, an alkoxy group, or a substituted amino group. ) represents a monovalent anion of enol. ]
In order to produce a metal complex represented by formula (XII): M
e＾w■L_W■(XII) (In the formula, Me, w and L represent the above.) A metal compound or its hydrate represented by the formula (XII)
:▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R_1, R_2, R_3, R_4, A method for producing metal complexes.