Polyether polyol and polyurethane compositions protected against oxidation and core scorching
AssigneeCiba-Geigy Corporation
InventorPeter Michaelis
Life of this patent
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Abstract
Described are compositions protected against thermal and oxidative degradation that comprise A) a polyether polyol or mixtures of such polyols, B) at least one benzofuranone derivative of formula I, ##STR1## wherein L, G, m, R.sub.1 to R.sub.5 and R.sub.21 to R.sub.24 are as defined in claim 1, C) at least one compound from the group of the phenolic anti-oxidants, and/or D) at least one compound from the group of the amino anti-oxidants of the secondary amine type. Also polyurethane(s) (foam(s)) prepared therefrom are protected against thermal and oxidative degradation, especially against core scorching.
Claims12
A composition comprising
- A) a polyether polyol or mixtures of such polyols,
- B) at least one benzofuranone derivative of formula I ##STR38## wherein L is oxygen or, when G is a direct bond and R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, does not exist,
- G is a direct bond or a group --CR.sub.18 R.sub.19 --CO--,
- m is 1 or 2,
- R.sub.1, when m=1 and G is a direct bond, is hydrogen, C.sub.1 -C.sub.25 alkyl, C.sub.3 -C.sub.25 alkenyl, C.sub.2 -C.sub.18 alkanoyl, C.sub.3 -C.sub.25 alkenoyl, C.sub.7 -C.sub.9 phenylalkyl, unsubstituted or C.sub.1 -C.sub.4 alkyl-substituted phenyl, unsubstituted or C.sub.1 -C.sub.4 alkyl-substituted C.sub.5 -C.sub.8 cycloalkyl, C.sub.3 -C.sub.25 -alkyl, -alkanoyl or -alkenyl interrupted by oxygen, sulfur or by >NR.sub.16, C.sub.6 -C.sub.9 cycloalkoxycarbonyl, benzoyl or C.sub.1 -C.sub.12 alkyl-substituted benzoyl, or
- R.sub.1, when m=2 and G is a direct bond, is --CO--R.sub.17 --CO--, or
- R.sub.1, when m=1 and G is a group --CR.sub.18 R.sub.19 --CO--,
- is hydroxy, C.sub.1 -C.sub.30 alkoxy, C.sub.3 -C.sub.30 alkoxy interrupted by oxygen, sulfur or by >NR.sub.13, C.sub.7 -C.sub.9 phenylalkoxy, C.sub.5 -C.sub.12 cycloalkoxy, C.sub.2 -C.sub.18 alkenyloxy, unsubstituted or C.sub.1 -C.sub.12 alkyl-substituted phenoxy, ##STR39## or R.sub.1, when m=2 and G is a group --CR.sub.18 R.sub.19 --CO--, is C.sub.2 -C.sub.12 alkanedioxy, C.sub.3 -C.sub.25 alkanedioxy interrupted by oxygen, sulfur or by >NR.sub.16, ##STR40## R.sub.2 and R.sub.4 are each, independently of the other, hydrogen or C.sub.1 -C.sub.6 alkyl, R.sub.3 and R.sub.5 are each, independently of the other, hydrogen, C.sub.1 -C.sub.25 alkyl, C.sub.7 -C.sub.9 phenylalkyl, unsubstituted or C.sub.1 -C.sub.4 alkyl-substituted phenyl, unsubstituted or C.sub.1 -C.sub.4 alkyl-substituted C.sub.5 -C.sub.8 cycloalkyl, C.sub.1 -C.sub.18 alkoxy, hydroxy, C.sub.1 -C.sub.25 alkanoyloxy, C.sub.3 -C.sub.25 alkenoyloxy, C.sub.3 -C.sub.25 alkenyloxy interrupted by oxygen, sulfur or by >NR.sub.16, C.sub.6 -C.sub.9 cycloalkylcarbonyloxy, benzoyloxy or C.sub.1 -C.sub.12 alkyl-substituted benzoyloxy, or a radical of the formula --(CH.sub.2).sub.n --CO--OR.sub.6, --(CH.sub.2).sub.n --COR.sub.11 or --(CH.sub.2).sub.n --CO--N(R.sub.7).sub.2,
- R.sub.3, when m=1, is furthermore a radical of the formula ##STR41## when m=1 and R.sub.4, R.sub.5, R.sub.21 R.sub.24 are hydrogen, R.sub.3 in addition is a radical of the formula ##STR42## R.sub.2 together with R.sub.3 or R.sub.4 together with R.sub.5, in each case together with the carbon atoms to which they are bonded, form a phenyl ring,
- R.sub.6 is hydrogen, C.sub.2 -C.sub.18 alkyl, C.sub.1 -C.sub.18 alkyl interrupted by oxygen or by sulfur, C.sub.3 -C.sub.16 dialkylaminoalkyl, cyclohexyl, phenyl, or phenyl substituted by from 1 to 3 alkyl radicals together having a maximum of 18 carbon atoms,
- n is 0, 1 or 2, the substituents
- R.sub.7 are each, independently of the other, hydrogen, C.sub.1 -C.sub.18 alkyl, cyclopentyl, cyclohexyl, phenyl, phenyl substituted by 1 or 2 alkyl radicals together having a maximum of 16 carbon atoms, a radical of the formula --C.sub.2 H.sub.4 OH, --C.sub.2 H.sub.4 --O--C.sub.q H.sub.2q+1 or --C.sub.2 H.sub.4 --O--CO--R.sub.10, together with the nitrogen atom to which they are bonded, form a piperidine or morpholine radical, wherein q is 1 to 18,
- R.sub.8 is hydrogen, alkyl having from 1 to 18 carbon atoms, cyclopentyl, cyclohexyl, phenyl, benzyl, phenyl substituted by 1 or 2 alkyl radicals together having a maximum of 16 carbon atoms, or benzyl,
- R.sub.9 is alkyl having from 1 to 18 carbon atoms,
- R.sub.10 is hydrogen, alkyl having from 1 to 22 carbon atoms or cycloalkyl having from 5 to 12 carbon atoms
- R.sub.11 is hydroxy, ##EQU2## C.sub.1 -C.sub.18 alkoxy or --NR.sub.14 R.sub.15, R.sub.12 and R.sub.13 are each, independently of the other, hydrogen, C.sub.1 -C.sub.12 alkyl or phenyl, or form together with the C-atom to which they are bound a C.sub.5 -C.sub.7 -alkylidene-ring which is unsubstituted or substituted by 1 to 3 C.sub.1 -C.sub.4 alkyl groups,
- R.sub.14 and R.sub.15 are each, independently of the other, hydrogen or C.sub.1 -C.sub.18 alkyl, M is an r-valent metal cation and r is 1, 2 or 3,
- A* is an alkylene radical having from 2 to 22 carbon atoms that may or may not be interrupted by nitrogen, oxygen or by sulfur,
- Y is --O--, --S--, --SO--, --SO.sub.2 -- or --C(R.sub.20).sub.2 --, wherein the substituents R.sub.20 are each, independently of the other, hydrogen, C.sub.1 -C.sub.16 alkyl, phenyl or a radical of the formula --(CH.sub.2).sub.n --CO--OR.sub.6 or --(CH.sub.2).sub.n --CO--N(R.sub.7).sub.2,
- E is a radical of the formula ##STR43## R.sub.16 is hydrogen or C.sub.1 -C.sub.8 alkyl, R.sub.17 is a direct bond, C.sub.1 -C.sub.18 alkylene, C.sub.2 -C.sub.18 alkylene interrupted by oxygen, sulfur or by >NR.sub.16, C.sub.2 -C.sub.18 alkenylene, C.sub.2 -C.sub.20 alkylidene, C.sub.7 -C.sub.20 phenylalkylidene, C.sub.5 -C.sub.8 cycloalkylene, C.sub.7 -C.sub.8 bicycloalkylene or phenylene,
- R.sub.18 and R.sub.19 are each, independently of the other, hydrogen, C.sub.1 -C.sub.4 alkyl or phenyl, and
- R.sub.21, R.sub.22, R.sub.23 R.sub.24 are each, independently of the others, hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, provided that at least one of the radicals R.sub.21, R.sub.22, R.sub.23 and R.sub.24 is hydrogen,
- C) at least one compound from the group of the phenolic anti-oxidants, and
- D) at least one compound of formula III ##STR44## wherein R.sub.38 is C.sub.1 -C.sub.18 alkyl, phenyl-C.sub.1 -C.sub.4 alkyl, C.sub.5 -C.sub.12 cycloalkyl, phenyl, naphthyl, or phenyl or naphthyl substituted by C.sub.1 -C.sub.12 alkyl or by C.sub.1 -C.sub.12 alkoxy,
- R.sub.39 is phenyl, naphthyl, or phenyl or naphthyl substituted by C.sub.1 -C.sub.12 alkyl or by C.sub.1 -C.sub.12 alkoxy, or
- R.sub.38 and R.sub.39 together form a radical of the formula IV ##STR45## wherein R.sub.40 and R.sub.41 are hydrogen or C.sub.1 -C.sub.18 alkyl or
- R.sub.41 is hydrogen or C.sub.1 -C.sub.18 alkyl and
- R.sub.40 together with R.sub.42 forms a group of the formula ##STR46## or, a composition comprising (A), (B) and (D).
Dependencies are inferred from the claim text.