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US 4,529,533 AGranted
Substituted 2-(2,6-di-t-butly-4-alkylphenoxy) 4H-1,3,2-benzodioxaphosphorins and compositions thereof
AssigneeThe B. F. Goodrich Company
InventorDwight W. Chasar
Life of this patent
Estimating the term…
Abstract
Substituted 2-(2,6-di-t-butyl-4-alkylphenoxy)-4H-1,3,2-benzodioxaphosphorins that are readily prepared, for example from hindered phenols and ortho-methylolphenols, are effective heat and anti-oxidant stabilizers for organic materials subject to degradation by heat and oxygen, and provide particularly efficient stabilizer systems when combined with hydroxyphenylalkyleneyl isocyanurates.
Claims18
2-(2,6-di-t-butyl-4-alkylphenoxy)-4H-1,3,2-benzodioxaphosphorin cyclic phosphites of the formula ##STR7## wherein:
- + is t-butyl;
- R.sub.1 is hydrogen, an alkyl radical containing 1 to 8 carbon atoms, a cycloalkyl radical containing 3 to 6 carbon atoms, halogen, an alkoxy radical containing 1 to 8 carbon atoms, phenyl, a --CH.sub.2 CH.sub.2 COOR.sub.6 group wherein R.sub.6 is an alkyl radical containing 1 to 8 carbon atoms, or t-alkyl radical containing 4 to 8 carbon atoms, and when R.sub.1 is t-butyl, no more than three of R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hydrogen;
- R.sub.2 is hydrogen, an alkyl radical containing 1 to 8 carbon atoms, and methoxy or phenyl when R.sub.3, R.sub.4 and R.sub.5 are hydrogen, or when R.sub.3 and R.sub.4 are hydrogen and R.sub.5 is methyl;
- R.sub.3 is methyl when R.sub.4 is methyl or hydrogen and R.sub.2 and R.sub.5 are hydrogen;
- R.sub.4 is hydrogen, an alkyl radical containing 1 to 8 carbon atoms, a cycloalkyl radical containing 3 to 6 carbon atoms, a t-alkyl radical containing 4 to 8 carbon atoms, methoxy, phenyl, halogen or methoxycarbonyl, when R.sub.2 is hydrogen, an alkyl radical containing 1 to 8 carbon atoms, a cycloalkyl radical containing 3 to 6 carbon atoms and a t-alkyl radical containing 4 to 8 carbon atoms, and R.sub.3 and R.sub.5 are hydrogen;
- R.sub.5 is methyl when R.sub.2, R.sub.3 and R.sub.4 are hydrogen, or when R.sub.4 is methyl and R.sub.2 and R.sub.3 are hydrogen, and hydrogen when R.sub.2, R.sub.3, R.sub.4 are the same as above;
- and when R.sub.4 and R.sub.5 are (--CH.dbd.CR.sub.7 --CH.dbd.CH--), R.sub.7 is hydrogen or t-butyl, and R.sub.2 is t-butyl or hydrogen and R.sub.3 is hydrogen;
- and when R.sub.2 and R.sub.3 are (--CH.dbd.CH--).sub.2, R.sub.4 and R.sub.5 are hydrogen;
- and at least one of said R.sub.2, R.sub.3 and R.sub.4 is an alkyl radical containing 1 to 8 carbon atoms.
6 more elements
A composition comprising polyolefin materials subject to degradation and stabilizing amounts of 2-(2,6-di-t-butyl-4-alkylphenoxy)-4H-1,3,2-benzodioxaphosphorins of the formula ##STR8## wherein:
- + is t-butyl;
- R.sub.1 is hydrogen, an alkyl radical containing 1 to 8 carbon atoms, a cycloalkyl radical containing 3 to 6 carbon atoms, halogen, an alkoxy radical containing 1 to 8 carbon atoms, phenyl, a --CH.sub.2 CH.sub.2 COOR.sub.6 group wherein R.sub.6 is an alkyl radical containing 1 to 8 carbon atoms, or t-alkyl radical containing 4 to 8 carbon atoms, and when R.sub.1 is t-butyl, no more than three of R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hydrogen;
- R.sub.2 is hydrogen, an alkyl radical containing 1 to 8 carbon atoms, and methoxy or phenyl when R.sub.3, R.sub.4 and R.sub.5 are hydrogen, or when R.sub.3 and R.sub.4 is hydrogen and R.sub.5 is methyl;
- R.sub.3 is methyl when R.sub.4 is methyl or hydrogen and R.sub.2 and R.sub.5 are hydrogen;
- R.sub.4 is hydrogen, an alkyl radical containing 1 to 8 carbon atoms, a cycloalkyl radical containing 3 to 6 carbon atoms, a t-alkyl radical containing 4 to 8 carbon atoms, methoxy, phenyl, halogen or methoxycarbonyl, when R.sub.2 is hydrogen, an alkyl radical containing 1 to 8 carbon atoms, a cycloalkyl radical containing 3 to 6 carbon atoms and a t-alkyl radical containing 4 to 8 carbon atoms, and R.sub.3 and R.sub.5 are hydrogen;
- R.sub.5 is methyl when R.sub.2, R.sub.3 and R.sub.4 are hydrogen, or when R.sub.4 is methyl and R.sub.2 and R.sub.3 are hydrogen, and hydrogen when R.sub.2, R.sub.3, R.sub.4 are the same as above;
- and when R.sub.4 and R.sub.5 are (--CH.dbd.CR.sub.7 --CH.dbd.CH--), R.sub.7 is hydrogen or t-butyl, and R.sub.2 is t-butyl or hydrogen and R.sub.3 is hydrogen;
- and when R.sub.2 and R.sub.3 are (--CH.dbd.CH--).sub.2, R.sub.4 and R.sub.5 are hydrogen;
- and at least one of said R.sub.2, R.sub.3, R.sub.4 and R.sub.5 is an alkyl radical containing 1 to 8 carbon atoms.
6 more elements
A composition comprising polyolefin materials subject to degradation and stabilizing amounts of (1) 2-(2,6-di-t-butyl-4-alkylphenoxy)-4H-1,3,2-benzodioxaphosphorins of the formula:
- ##STR9## wherein:
- + is t-butyl;
- R.sub.1 is hydrogen, an alkyl radical containing 1 to 8 carbon atoms, a cycloalkyl radical containing 3 to 6 carbon atoms, halogen, an alkoxy radical containing 1 to 8 carbon atoms, phenyl, a --CH.sub.2 CH.sub.2 COOR.sub.6 group wherein R.sub.6 is an alkyl radical containing 1 to 8 carbon atoms, or t-alkyl radical containing 4 to 8 carbon atoms, and when R.sub.1 is t-butyl, no more than three of R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hydrogen;
- R.sub.2 is hydrogen, an alkyl radical containing 1 to 8 carbon atoms, and methoxy or phenyl when R.sub.3, R.sub.4 and R.sub.5 are hydrogen, or when R.sub.3 and R.sub.4 are hydrogen and R.sub.5 is methyl;
- R.sub.3 is methyl when R.sub.4 is methyl or hydrogen and R.sub.2 and R.sub.5 are hydrogen;
- R.sub.4 is hydrogen, an alkyl radical containing 1 to 8 carbon atoms, a cycloalkyl radical containing 3 to 6 carbon atoms, a t-alkyl radical containing 4 to 8 carbon atoms, methoxy, phenyl, halogen or methoxycarbonyl, when R.sub.2 is hydrogen, an alkyl radical containing 1 to 8 carbon atoms, a cycloalkyl radical containing 3 to 6 carbon atoms and a t-alkyl radical containing 4 to 8 carbon atoms, and R.sub.3 and R.sub.5 are hydrogen;
- R.sub.5 is methyl when R.sub.2, R.sub.3 and R.sub.4 are hydrogen, or when R.sub.4 is methyl and R.sub.2 and R.sub.3 are hydrogen, and hydrogen when R.sub.2, R.sub.3, R.sub.4 are the same as above;
- and when R.sub.4 and R.sub.5 are (--CH.dbd.CR.sub.7 --CH.dbd.CH--), R.sub.7 is hydrogen or t-butyl, and R.sub.2 is t-butyl or hydrogen and R.sub.3 is hydrogen;
- and when R.sub.2 and R.sub.3 are (--CH.dbd.CH--).sub.2, R.sub.4 and R.sub.5 are hydrogen;
- and at least one of said R.sub.2, R.sub.3, R.sub.4 and R.sub.5 is an alkyl radical containing 1 to 8 carbon atoms;
- and (2) hydroxyphenylalkyleneyl isocyanurates of the formula ##STR10## wherein R' is a hydroxyphenylalkyleneyl radical of the formula ##STR11## where m is 1 to 4, r.sub.1 is an alkyl radical having 1 to 18 carbon atoms and is positioned immediately adjacent to the hydroxy group on the ring;
- r.sub.2, r.sub.3 and r.sub.4 are hydrogen or an alkyl radical containing 1 to 18 carbon atoms;
- and R" and R"' are hydrogen, an alkyl radical containing 1 to 18 carbon atoms, or are the same as r';
- and R" and R"' are hydrogen, an alkyl radical containing 1 to 18 carbon atoms, or are the same as R'.
11 more elements
Dependencies are inferred from the claim text.