Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...
Reexamination Certificate
1997-11-26
2001-06-05
Ambrose, Michael G. (Department: 1626)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Processes of preparing a desired or intentional composition...
C524S119000, C558S082000, C558S086000
Reexamination Certificate
active
06242514
ABSTRACT:
The present invention relates to a novel pentavalent phosphorus-containing compound, a method for producing the same and use thereof.
When organic materials such as a thermoplastic resin, thermosetting resin, natural or synthetic rubber, mineral oil, lubricating oil, adhesive, paint and the like are produced, processed or used, they are tend to be degraded by the action of heat, oxygen and the like. Such degradation causes decrease in physical strength, change of flowability, coloration, decrease in surface physical property and the like of the organic materials, and lowers market value thereof remarkably. It is conventionally known to include various phenolic antioxidants, phosphorus antloxidants and the like in an organic material in order to solve such problems as heat degradation and oxygen degradation and to stabilize the organic material.
For example, as the phosphorus antioxidant, pentavalent phosphorus compounds such as 3,5-di-t-butyl-4-hydroxybenzylphosphonate diethylester are known. However, these known phosphorus antioxidants are still insufficient in stabilization effect against heat degradation and oxygen degradation.
The present inventors have produced various phosphorus compounds and intensively studied about them, and as a result, found that a specific phosphorus compound such as a cyclic pentavalent phosphorus compound exhibits excellent stabilization effect. The present invention was thus completed.
The present invention provides a pentavalent phosphorus compound represented by the formula (I):
wherein R
A
forms a cyclic group together with E, O and P, E represents a direct bond or oxygen atom, F represents a connecting group, and R
B
represents a phenyl group which may be optionally substituted.
The present invention also provides a method for producing the same, and use thereof.
In the pentavalent phosphorus compound of formula (I), R
A
forms a cyclic group together with E, O and P. Examples of R
A
include a bisphenylene group having a total carbon atom number of about 12 to 80, which may be optionally substituted, a phenylene group having a total carbon atom number of about 6 to 30, which may be optionally substituted, or an alkylene group having a total carbon atom number of about 3 to 60, which may be optionally substituted.
Typical examples of the bisphenylene group as R
A
include a biphenylene group, an alkylenebisphenylene group or a thiobisphenylene group, represented by the formula (II):
wherein R
1
and R
2
each independently represents a hydrogen atom, alkyl group having 1 to 8 carbon atoms, cycloalkyl group having 5 to 8 carbon atoms, alkylcycloalkyl group having 6 to 12 carbon atoms, aralkyl group having 7 to 12 carbon atoms or phenyl group, R
3
represents a hydrogen atom or alkyl group having 1 to 8 carbon atoms, X represents a direct bond, sulfur atom, unsubstituted methylene group or methylene group substituted with an alkyl having 1 to 8 carbon atoms or a cycloalkyl having 5 to 8 carbon atoms.
Typical examples of the phenylene group as R
A
include o-phenylene group represented by the formula (III):
wherein R
1
and R
2
are as defined above.
In the formulae (II) and (III), substituents R
1
and R
2
each independently represent a hydrogen atom, alkyl group having 1 to 8 carbon atoms, cycloalkyl group having 5 to 8 carbon atoms, alkylcycloalkyl group having 6 to 12 carbon atoms, aralkyl group having 7 to 12 carbon atoms or phenyl group. In the formula (II), substituent R
3
represents a hydrogen atom or alkyl group having 1 to 8 carbon atoms.
Typical examples of the alkyl group having I to 8 carbon atoms, as R
1
, R
2
or R
3
, include methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, t-butyl, t-pentyl, i-octyl, t-octyl and 2-ethylhexyl.
Typical examples of the cycloalkyl group having 5 to 8 carbon atoms, as R
1
or R
2
, include cyclo-entyl, cyclohexyl, cycloheptyl and cyclooctyl.
Typical examples of the alkylcycloalkyl group having 6 to 12 carbon atoms, as R
1
or R
2
, include 1-methylcyclopentyl, 1-methylcyclohexyl and 1-methyl-4-i-propylcyclohexyl.
Typical examples of the aralkl group having 7 to 12 carbon atoms, as R
1
or R
2
, include benzyl, a-methylbenzyl and &agr;,&agr;-dimethylbenzyl.
R
1
is preferably t-alkyl group such as t-butyl, t-pentyl, t-octyl and 1-methylcyclohexyl. R
2
is preferably alkyl group having 1 to 5 carbon atoms such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, t-butyl and t-pentyl, and particularly preferably t-butyl. R
3
is preferably a hydrogen atom or alkyl group having 1 to 5 carbon atoms, and particularly preferably a hydrogen atom or methyl group.
The substituent X represents a direct bond, sulfur atom, unsubstituted methylene group or methylene group substituted with alkyl having 1 to 8 carbon atoms or cycloalkyl having 5 to 8 carbon atoms. Typical examples of said alkyl group having 1 to 8 carbon atoms, as the substituent on the methylene group as X, include methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, t-butyl, t-pentyl, i-octyl, t-octyl and 2-ethylhexyl. Typical examples of said cycloalkyl group having 5 to 8 carbon atoms, as the substituent on the methylene group as X, include cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
X is preferably a direct bond, unsubstituted methylene group or methylene group substituted with methyl group.
Typical examples of the alkylene group as R
A
include propylene group represented by the formulae (IV):
wherein R
4
, R
5
, R
6
and R
7
each independently represent a hydrogen atom, alkyl group having 1 to 8 carbon atoms, cycloalkyl group having 5 to 8 carbon atoms, alkylcycloalkyl group having 6 to 12 carbon atoms, aralkyl group having 7 to 12 carbon atoms or phenyl group, and ethylene group represented by the formulae (V):
wherein R
4
, R
5
and R
6
are as defined above.
Typical examples of the alkyl group having 1 to 8 carbon atoms, as R
4
, R
5
, R
6
or R
7
, include methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, t-butyl, t-pentyl, i-octyl, t-octyl and 2-ethylhexyl.
Typical examples of the cycloalkyl group having 5 to 8 carbon atoms, as R
4
, R
5
, R
6
or R
7
, include cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. Typical examples of the alkylcycloalkyl group having 6 to 12 carbon atoms, as R
4
, R
5
, R
6
or R
7
, include 1-methylcyclopentyl, 1-methylcyclohexyl and 1-methyl-4-i-propylcyclohexyl. Typical examples of the aralkyl group having 7 to 12 carbon atoms, as R
4
, R
5
, R
6
or R
7
, include benzyl, &agr;-methylbenzyl and &agr;,&agr;-dimethylbenzyl.
R
4
, R
5
, R
6
and R
7
are preferably a hydrogen atom or alkyl group having 1 to 8 carbon atoms, and more preferably a hydrogen atom or methyl group.
The mark E in the formula (I) represents a direct bond or oxygen atom, and preferably an oxygen atom.
The mark F represents a connecting group. Examples of such connecting group as F include a direct bond and a divalent connecting group having about 1 to 20 carbon atoms in total optionally having a hetero atom. Specific example of the divalent connecting group include those represented by the following formulae (VI) (VII), (VIII), (IX), (X), (XI) or (XII):
*—A— (VI)
*—C(O)—A— (VII)
*—B—O—A— (VIII)
*—B—O—C(O)—A— (IX)
*—D—C(O)—O—A— (X)
*—G—N(R
8
)—A— (XI)
*—G—N(R
8
)—C(O)—A— (XII)
wherein *— represents a bond to the oxygen atom, A represents a direct bond or an alkylene group having 1 to 8 carbon atoms, B represents a divalent alcohol residue, D represents an alkylene group having 1 to 8 carbon atoms, G represents an alkylene group having 2 to 8 carbon atoms, and R
8
represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a group represented by the formula (XIII)
wherein R
A
, E and G are as defined above.
Typical examples of said alkylene group having 1 to 8 carbon atoms, as A or D, include straight-chain alkylene such as methylene, ethylene, propylene, butylene, pentamethylene, hexamethylene and octamethylene; branched alkylenes such as 1-methylethylene, dimethyl
Fukuda Kanako
Inui Naoki
Kikuchi Taketoshi
Sanada Takashi
Ambrose Michael G.
Pillsbury & Winthrop LLP
Sumitomo Chemical Company Ltd.
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