Substituted 2-(2,6-di-t-butly-4-alkylphenoxy) 4H-1,3,2-benzodioxaphosphorins and compositions thereof

Claim 2

2-(2,6-di-t-butyl-4-alkylphenoxy)-4H-1,3,2-benzodioxaphosphorin cyclic phosphites of the formula ##STR7## wherein: + is t-butyl; R 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 2 CH 2 COOR 6 group wherein R 6 is an alkyl radical containing 1 to 8 carbon atoms, or t-alkyl radical containing 4 to 8 carbon atoms, and when R 1 is t-butyl, no more than three of R 2 , R 3 , R 4 and R 5 are hydrogen; R 2 is hydrogen, an alkyl radical containing 1 to 8 carbon atoms, and methoxy or phenyl when R 3 , R 4 and R 5 are hydrogen, or when R 3 and R 4 are hydrogen and R 5 is methyl; R 3 is methyl when R 4 is methyl or hydrogen and R 2 and R 5 are hydrogen; R 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 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 3 and R 5 are hydrogen; R 5 is methyl when R 2 , R 3 and R 4 are hydrogen, or when R 4 is methyl and R 2 and R 3 are hydrogen, and hydrogen when R 2 , R 3 , R 4 are the same as above; and when R 4 and R 5 are (--CH═CR 7 --CH═CH--), R 7 is hydrogen or t-butyl, and R 2 is t-butyl or hydrogen and R 3 is hydrogen; and when R 2 and R 3 are (--CH═CH--) 2 , R 4 and R 5 are hydrogen; and at least one of said R 2 , R 3 and R 4 is an alkyl radical containing 1 to 8 carbon atoms.

Claim 3

Cyclic phosphites of claim 1 wherein R 1 is hydrogen, a primary, secondary or tertiary alkyl group containing 1 to 4 carbon atoms, or a --CH 2 CH 2 COOR 6 group wherein R 6 is an alkyl radical containing 1 to 4 carbon atoms; R 2 is hydrogen, a primary, secondary tertiary alkyl radical containing 1 to 4 carbon atoms; R 3 is hydrogen or methyl; R 4 is hydrogen or a primary, secondary or tertiary alkyl radical containing 1 to 4 carbon atoms; and R 5 is hydrogen.

Claim 4

A cyclic phosphite of claim 2, 2-[4-methyl-2,6-bis(1,1-dimethylethyl)phenoxy]-6-methyl-4H-1,3,2-benzodioxaphosphorin.

Claim 5

A cyclic phosphite of claim 2, 2-[4-methyl-2,6-bis(1,1-dimethylethyl)phenoxy]-6,8-dimethyl-4H-1,3,2-benzodioxaphosphorin.

Claim 6

A cyclic phosphite of claim 2, 2-[2,4,6-tris(1,1-dimethylethyl)phenoxy]6,8-dimethyl-4H-1,3,2-benzodioxaphosphorin.

Claim 7

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 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 2 CH 2 COOR 6 group wherein R 6 is an alkyl radical containing 1 to 8 carbon atoms, or t-alkyl radical containing 4 to 8 carbon atoms, and when R 1 is t-butyl, no more than three of R 2 , R 3 , R 4 and R 5 are hydrogen; R 2 is hydrogen, an alkyl radical containing 1 to 8 carbon atoms, and methoxy or phenyl when R 3 , R 4 and R 5 are hydrogen, or when R 3 and R 4 is hydrogen and R 5 is methyl; R 3 is methyl when R 4 is methyl or hydrogen and R 2 and R 5 are hydrogen; R 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 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 3 and R 5 are hydrogen; R 5 is methyl when R 2 , R 3 and R 4 are hydrogen, or when R 4 is methyl and R 2 and R 3 are hydrogen, and hydrogen when R 2 , R 3 , R 4 are the same as above; and when R 4 and R 5 are (--CH═CR 7 --CH═CH--), R 7 is hydrogen or t-butyl, and R 2 is t-butyl or hydrogen and R 3 is hydrogen; and when R 2 and R 3 are (--CH═CH--) 2 , R 4 and R 5 are hydrogen; and at least one of said R 2 , R 3 , R 4 and R 5 is an alkyl radical containing 1 to 8 carbon atoms.

Claim 8

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 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 2 CH 2 COOR 6 group wherein R 6 is an alkyl radical containing 1 to 8 carbon atoms, or t-alkyl radical containing 4 to 8 carbon atoms, and when R 1 is t-butyl, no more than three of R 2 , R 3 , R 4 and R 5 are hydrogen; R 2 is hydrogen, an alkyl radical containing 1 to 8 carbon atoms, and methoxy or phenyl when R 3 , R 4 and R 5 are hydrogen, or when R 3 and R 4 is hydrogen and R 5 is methyl; R 3 is methyl when R 4 is methyl or hydrogen and R 2 and R 5 are hydrogen; R 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 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 3 and R 5 are hydrogen; R 5 is methyl when R 2 , R 3 and R 4 are hydrogen, or when R 4 is methyl and R 2 and R 3 are hydrogen, and hydrogen when R 2 , R 3 , R 4 are the same as above; and when R 4 and R 5 are (--CH═CR 7 --CH═CH--), R 7 is hydrogen or t-butyl, and R 2 is t-butyl or hydrogen and R 3 is hydrogen; and when R 2 and R 3 are (--CH═CH--) 2 , R 4 and R 5 are hydrogen; and at least one of said R 2 , R 3 , R 4 and R 5 is an alkyl radical containing 1 to 8 carbon atoms.

Claim 9

A composition of claim 6 wherein R 1 is hydrogen, a primary, secondary or tertiary alkyl group containing 1 to 4 carbon atoms, or a --CH 2 CH 2 COOR 6 group wherein R 6 is an alkyl radical contianing 1 to 4 carbon atoms; R 2 is hydrogen, a primary, secondary or tertiary alkyl radical containing 1 to 4 carbon atoms; R 3 is hydrogen or methyl; R 4 is hydrogen or a primary, secondary or tertiary alkyl radical containing 1 to 4 carbon atoms; and R 5 is hydrogen.

Claim 10

A composition of claim 7 containing polypropylene and 2-[4-methyl-2,6-bis(1,1-dimethylethyl)phenoxy]-6-methyl-4H-1,3,2-benzodioxaphosphorin.

Claim 11

A composition of claim 7 containing polypropylene and 2-[4-methyl-2,6-bis(1,1-dimethylethyl)phenoxy]-6,8-dimethyl-4H-1,3,2-benzodioxaphosphorin.

Claim 12

A composition of claim 7 containing polypropylene and 2-[2,4,6-tris(1,1-dimethylethyl)phenoxy]-6,8-dimethyl-4H-1,3,2-benzodioxaphosphorin.

Claim 13

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 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 2 CH 2 COOR 6 group wherein R 6 is an alkyl radical containing 1 to 8 carbon atoms, or t-alkyl radical containing 4 to 8 carbon atoms, and when R 1 is t-butyl, no more than three of R 2 , R 3 , R 4 and R 5 are hydrogen; R 2 is hydrogen, an alkyl radical containing 1 to 8 carbon atoms, and methoxy or phenyl when R 3 , R 4 and R 5 are hydrogen, or when R 3 and R 4 are hydrogen and R 5 is methyl; R 3 is methyl when R 4 is methyl or hydrogen and R 2 and R 5 are hydrogen; R 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 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 3 and R 5 are hydrogen; R 5 is methyl when R 2 , R 3 and R 4 are hydrogen, or when R 4 is methyl and R 2 and R 3 are hydrogen, and hydrogen when R 2 , R 3 , R 4 are the same as above; and when R 4 and R 5 are (--CH═CR 7 --CH═CH--), R 7 is hydrogen or t-butyl, and R 2 is t-butyl or hydrogen and R 3 is hydrogen; and when R 2 and R 3 are (--CH═CH--) 2 , R 4 and R 5 are hydrogen; and at least one of said R 2 , R 3 , R 4 and R 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 1 is an alkyl radical having 1 to 18 carbon atoms and is positioned immediately adjacent to the hydroxy group on the ring; r 2 , r 3 and r 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'.

Claim 14

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 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 2 CH 2 COOR 6 group wherein R 6 is an alkyl radical containing 1 to 8 carbon atoms, or t-alkyl radical containing 4 to 8 carbon atoms, and when R 1 is t-butyl, no more than three of R 2 , R 3 , R 4 and R 5 are hydrogen; R 2 is hydrogen, an alkyl radical containing 1 to 8 carbon atoms, and methoxy or phenyl when R 3 , R 4 and R 5 are hydrogen, or when R 3 and R 4 are hydrogen and R 5 is methyl; R 3 is methyl when R 4 is methyl or hydrogen and R 2 and R 5 are hydrogen; R 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 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 3 and R 5 are hydrogen; R 5 is methyl when R 2 , R 3 and R 4 are hydrogen, or when R 4 is methyl and R 2 and R 3 are hydrogen, and hydrogen when R 2 , R 3 , R 4 are the same as above; and when R 4 and R 5 are (--CH═CR 7 --CH═CH--), R 7 is hydrogen or t-butyl, and R 2 is t-butyl or hydrogen and R 3 is hydrogen; and when R 2 and R 3 are (--CH═CH--) 2 , R 4 and R 5 are hydrogen; and at least one of said R 2 , R 3 , R 4 and R 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 1 is an alkyl radical having 1 to 18 carbon atoms and is positioned immediately adjacent to the hydroxy group on the ring; r 2 , r 3 and r 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'.

Claim 15

A composition of claim 11 wherein in (1) R 1 is hydrogen, a primary, secondary or tertiary alkyl group containing 1 to 4 carbon atoms, or a --CH 2 CH 2 COOR 6 group wherein R 6 is an alkyl radical containing 1 to 4 carbon atoms; R 2 is hydrogen, a primary, secondary or tertiary alkyl group containing 1 to 4 carbon atoms; R 3 is hydrogen or methyl; R 4 is hydrogen or a primary, secondary or tertiary alkyl radical containing 1 to 4 carbon atoms; and R 5 is hydrogen.

Claim 16

A composition of claim 12 wherein in (2) R" and R"' are equal to R', r 1 is a tertiary alkyl radical containing 4 to about 12 carbon atoms, r 2 is an alkyl radical containing 1 to about 12 carbon atoms, r 3 and r 4 are hydrogen, and m=1.

Claim 17

A composition of claim 13 where (2) has the formula ##STR12## where n is 4 to 8.

Claim 18

A composition of claim 14 where (2) is 1,35,-tris(3,5-di-t-butyl-4-hydroxybenzyl)isocyanurate.

Claim 19

A composition of claim 15 wherein said polyolefin is polypropylene and (1) is 2-[4-methyl-2,6-bis(1,1-dimethylethyl)phenoxy]-6-methyl-4H-1,3,2-benzodioxaphosphorin.

Claim 20

A composition of claim 15 wherein said polyolefin is polypropylene and (1) is 2-[4-methyl-2,6-bis(1,1-dimethylethyl)phenoxy]-6,8-dimethyl-4H-1,3,2-benzodioxaphosphorin.

Claim 21

A composition of claim 15 wherein said polyolefin is polypropylene and (1) is 2-[2,4,6-tris(1,1-dimethylethyl)phenoxy]-6,8-dimethyl-4H-1,3,2-benzodioxaphosphorin.