5-Membered cyclic phosphonates and compositions thereof

Claim 2

2-[alkylphenoxy]-2,3-dihydro-1,2-benzoxaphosphole 2-oxide cyclic phosphonates 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 a t-alkyl radical containing 4 to 8 carbon atoms; 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═CH 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.

Claim 3

Cyclic phosphonates of claim 1 wherein R 1 is hydrogen, a 1°, 2° or 3° alkyl group of 1 to 4 carbon atoms, and the --CH 2 CH 2 COOR 6 group where R 6 is an alkyl group of 1 to 4 carbon atoms; R 2 is hydrogen or a 1°, 2°, or 3° alkyl group of 1 to 4 carbon atoms; R 3 is hydrogen or methyl; R 4 is hydrogen or a 1°, 2°, or 3° alkyl group of 1 to 4 carbon atoms; and R 5 is hydrogen.

Claim 4

A cyclic phosphonate of claim 2, 2-[4-methyl-2,6-bis(1,1-dimethylethyl)phenoxy]-7-(1,1-dimethylethyl)-2,3-dihydro-1,2-benzophosphole 2-oxide.

Claim 5

A cyclic phosphonate of claim 2, 2-[4-methyl-2,6-bis(1,1-dimethylethyl)phenoxy]-5-(1,1-dimethylethyl)-7-methyl-2,3-dihydro-1,2-benzoxaphosphole 2-oxide.

Claim 6

A cyclic phosphonate of claim 2, 2-[4-methyl-2,6-bis(1,1-dimethylethyl)phenoxy]-5-methyl-7-(1,1-dimethylethyl)-2,3-dihydro-1,2-benzoxaphosphole 2-oxide.

Claim 7

A cyclic phosphonate of claim 2, 2-[2,4,6-tris(1,1-dimethylethyl)phenoxy]-5-methyl-2,3-dihydro-1,2-benzoxaphosphole 2-oxide.

Claim 8

A composition comprising organic materials subject to degradation and stabilizing amounts of 2-[alkylphenoxy]-2,3-dihydro-1,2-benzoxaphosphole 2-oxide cyclic phosphonates 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; 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═CH 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.

Claim 9

A composition comprising organic materials subject to degradation and stabilizing amounts of 2-[alkylphenoxy]-2,3-dihydro-1,2-benzoxaphosphole 2-oxide cyclic phosphonates 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; 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═CH 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.

Claim 10

A composition of claim 7 wherein said organic material is a polymer and R 1 is hydrogen, a 1°, 2°, or 3° alkyl group of 1 to 4 carbon atoms, and the --CH 2 CH 2 COOR 6 group where R 6 is an alkyl group of 1 to 4 carbon atoms; R 2 is hydrogen or a 1°, 2°, or 3° alkyl group of 1 to 4 carbon atoms; R 3 is hydrogen or methyl; R 4 is hydrogen or a 1°, 2°, or 3° alkyl group of 1 to 4 carbon atoms; and R 5 is hydrogen.

Claim 11

A composition of claim 8 containing a polyolefin and 2-[4-methyl-2,6-bis(1,1-dimethylethyl)phenoxy]-7-(1,1-dimethylethyl)-2,3-dihydro-1,2-benzoxaphosphole 2-oxide.

Claim 12

A composition of claim 8 containing a polyolefin and 2-[4-methyl-2,6-bis(1,1-dimethylethyl)phenoxy]-5-(1,1-dimethylethyl)-7-methyl-2,3-dihydro-1,2-benzoxaphosphole 2-oxide.

Claim 13

A composition of claim 8 containing a polyolefin and 2-[4-methyl-2,6-bis(1,1-dimethylethyl)phenoxy]-5-methyl-7-(1,1-dimethylethyl)-2,3-dihydro-1,2-benzoxaphosphole 2-oxide.

Claim 14

A composition of claim 8 containing a polyolefin and 2-[2,4,6-tris(1,1-dimethylethyl)phenoxy]-5-methyl-2,3-dihydro-1,2-benzoxaphosphole 2-oxide.

Claim 15

A stabilizer composition for organic materials subject to degradation comprising (1) 2-[alkylphenoxy]-2,3-dihydro-1,2-benzoxaphosphole 2-oxide cyclic phosphonates 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 a t-alkyl radical containing 4 to 8 carbon atoms; 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 1 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 (2) a hydroxyphenylalkyleneyl isocyanurate 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'. A more preferred compound is when R" and R"' are equal to R'.

Claim 16

A stabilizer composition for organic materials subject to degradation comprising (1) 2-[alkylphenoxy]-2,3-dihydro-1,2-benzoxaphosphole 2-oxide cyclic phosphonates 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 a t-alkyl radical containing 4 to 8 carbon atoms; 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 1 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 (2) a hydroxyphenylalkyleneyl isocyanurate 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'. A more preferred compound is when R" and R"' are equal to R'.

Claim 17

A stabilizer of claim 13 wherein in (1) R 1 is hydrogen, a 1°, 2° or 3° alkyl group of 1 to 4 carbon atoms, and the --CH 2 CH 2 COOR 6 group where R 6 is an alkyl group of 1 to 4 carbon atoms; R 2 is hydrogen or a 1°, 2°, or 3° alkyl group of 1 to 4 carbon atoms; R 3 is hydrogen or methyl; R 4 is hydrogen or a 1°, 2° or 3° alkyl group of 1 to 4 carbon atoms; and R 5 is hydrogen; and 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 18

A stabilizer of claim 14 where (2) has the formula ##STR12## where n is 4 to 8.

Claim 19

A stabilizer of claim 15 where (2) is 1,3,5-tris(3,5-di-t-butyl-4-hydroxybenzyl) isocyanurate.

Claim 20

A stabilizer of claim 16 wherein (1) is 2-[4-methyl-2,6-bis(1,1-dimethylethyl)phenoxy]-7-(1,1-dimethylethyl)-2,3-dihydro-1,2-benzoxaphosphole 2-oxide.

Claim 21

A stabilizer of claim 16 wherein (1) is 2-[4-methyl-2,6-bis(1,1-dimethylethyl)phenoxy]-5-(1,1-dimethylethyl)-7-methyl-2,3-dihydro-1,2-benzoxaphosphole 2-oxide.

Claim 22

A stabilizer of claim 16 wherein (1) is 2-[4-methyl-2,6-bis(1,1-dimethylethyl)phenoxy]-5-methyl-7-(1,1-dimethylethyl)-2,3-dihydro-1,2-benzoxaphosphole 2-oxide.

Claim 23

A stabilizer of claim 16 wherein (1) is 2-[2,4,6-tris(1,1-dimethylethyl)phenoxy]-5-methyl-2,3-dihydro-1,2-benzoxaphosphole 2-oxide.

Claim 24

A composition comprising organic materials subject to degradation and stabilizing amounts of (1) 2-[alkylphenoxy]-2,3-dihydro-1,2-benzoxaphosphole 2-oxide cyclic phosphonates of the formula: ##STR13## 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 a t-alkyl radical containing 4 to 8 carbon atoms; 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 (2) a hydroxyphenylalkyleneyl isocyanurate of the formula ##STR14## wherein R' is a hydroxyphenylalkyleneyl radical of the formula ##STR15## 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'.

Claim 25

A composition comprising organic materials subject to degradation and stabilizing amounts of (1) 2-[alkylphenoxy]-2,3-dihydro-1,2-benzoxaphosphole 2-oxide cyclic phosphonates of the formula: ##STR13## 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 a t-alkyl radical containing 4 to 8 carbon atoms; 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 (2) a hydroxyphenylalkyleneyl isocyanurate of the formula ##STR14## wherein R' is a hydroxyphenylalkyleneyl radical of the formula ##STR15## 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'.

Claim 26

A composition of claim 21 wherein said organic material is a polymer and in (1) R 1 is hydrogen, a 1°, 2° or 3° alkyl group of 1 to 4 carbon atoms, and the --CH 2 CH 2 COOR 6 group where R 6 is an alkyl group of 1 to 4 carbon atoms; R 2 is hydrogen or a 1°, 2°, or 3° alkyl group of 1 to 4 carbon atoms; R 3 is hydrogen or methyl; R 4 is hydrogen or a 1°, 2°, or 3° alkyl group of 1 to 4 carbon atoms; and R 5 is hydrogen.

Claim 27

A composition of claim 22 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 28

A composition of claim 23 where (2) has the formula ##STR16## where n is 4 to 8.

Claim 29

A composition of claim 24 where (2) is 1,3,5-tris(3,5-di-t-butyl-4-hydroxybenzyl) isocyanurate.

Claim 30

A composition of claim 25 wherein said polymer is a polyolefin and (1) is 2-[4-methyl-2,6-bis(1,1-dimethylethyl)phenoxy]-7-(1,1-dimethylethyl)-2,3-dihydro-1,2-benzoxaphosphole 2-oxide.

Claim 31

A composition of claim 25 wherein said polymer is a polyolefin and (1) is 2-[4-methyl-2,6-bis(1,1-dimethylethyl)phenoxy]-5-(1,1-dimethylethyl)-7-methyl-2,3-dihydro-1,2-benzoxaphosphole 2-oxide.

Claim 32

A composition of claim 25 wherein said polymer is a polyolefin and (1) is 2-[4-methyl-2,6-bis(1,1-dimethylethyl)phenoxy]-5-methyl-7-(1,1-dimethylethyl)-2,3-dihydro-1,2-benzoxaphosphole 2-oxide.

Claim 33

A composition of claim 25 wherein said polymer is a polyolefin and (1) is 2-[2,4,6-tris(1,1-dimethylethyl)phenoxy]-5-methyl-2,3-dihydro-1,2-benzoxaphosphole 2-oxide.