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US 7,767,739 B2Granted
Cyanato group-containing cyclic phosphazene compound and method for producing the same
AssigneeFushimi Pharmaceutical Co., Ltd.
InventorsYuji Tada, Takashi Inoue
Life of this patent
Estimating the term…
Abstract
A phosphazene compound, which can effectively enhance flame retardancy without deteriorating mechanical properties of a resin molded product, and is also less likely to deteriorate thermal reliability and dielectric properties, is represented by the formula (1) shown below. n represents an integer of 3 to 15. wherein A represents a group selected from the group consisting of an alkoxy group, an aryloxy group and a group having a cyanato group, and at least one is a group having a cyanato group, and an example of A is a cyanatophenyl-substituted phenyloxy group represented by the formula (4) shown below, and Y in the formula (4) represents O, S, SO2, CH2, CHCH3, C(CH3)2, C(CF3)2, C(CH3)CH2CH3 or CO.
Claims14
A cyanato group-containing cyclic phosphazene compound represented by the following formula (1):
- in the formula (1), n represents an integer of 3 to 15, A represents a group selected from the group consisting of an A1 group, an A2 group and an A3 group shown below, and at least one group is an A3 group:
- A1 group:
- an alkoxy group having 1 to 8 carbon atoms which may be substituted with at least one group selected from an alkyl group having 1 to 6 carbon atoms, an alkenyl group and an aryl group,
- A2 group:
- an aryloxy group having 6 to 20 carbon atoms which may be substituted with at least one group selected from an alkyl group having 1 to 6 carbon atoms, an alkenyl group and an aryl group, and
- A3 group:
- a group selected from the group consisting of a cyanatophenyloxy group represented by the formula (2) shown below, a cyanatophenyl-substituted phenyloxy group represented by the formula (3) shown below, a cyanatophenyl-substituted phenyloxy group represented by the formula (4) shown below, a cyanatophenyl-substituted indanoxy group represented by the formula (5) shown below and a cyanatoindane-substituted phenyloxy group represented by the formula (6) shown below:
- in the formula (4), Y represents O, S, SO2, CH2, CHCH3, C(CH3)2, C(CF3)2, C(CH3)CH2CH3 or CO,
- in the formulas (5) and (6), R1 and R2 represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group or a phenyl group.
6 more elements
A method for producing a cyanato group-containing cyclic phosphazene compound, which comprises the steps of:
- substituting all halogen atoms of a cyclic phosphonitrile dihalide represented by the formula (7) shown below with a group selected from the group consisting of an E1 group, an E2 group and an E3 group shown below so as to substitute at least one of the halogen atoms with the E3 group shown below to produce a cyclic phosphonitrile-substituted compound;
- in the formula (7), n represents an integer of 3 to 15 and X represents a halogen atom,
- E1 group:
- an alkoxy group having 1 to 8 carbon atoms which may be substituted with at least one group selected from an alkyl group having 1 to 6 carbon atoms, an alkenyl group and an aryl group,
- E2 group:
- an aryloxy group having 6 to 20 carbon atoms which may be substituted with at least one group selected from an alkyl group having 1 to 6 carbon atoms, an alkenyl group and an aryl group, and
- E3 group:
- a group selected from the group consisting of a substituted phenyloxy group represented by the formula (8) shown below, a substituted phenyloxy group represented by the formula (9) shown below, a substituted phenyloxy group represented by the formula (10) shown below, a substituted indanoxy group represented by the formula (11) shown below and a substituted phenyloxy group represented by the formula (12) shown below:
- wherein Z in the formulas (8), (9), (10), (11) and (12) represents a protecting group capable of forming an OH group when eliminated, Y in the formula (10) represents O, S, SO2, CH2, CHCH3, C(CH3)2, C(CF3)2, C(CH3)CH2CH3 or CO, and R1 and R2 in the formulas (11) and (12) represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group or a phenyl group;
- eliminating the protecting group from the E3 group of the cyclic phosphonitrile-substituted compound to produce a cyclic phosphonitrile-substituted compound having a hydroxyl group;
- and
- reacting the cyclic phosphonitrile-substituted compound having a hydroxyl group with a cyanogen halide.
9 more elements
A resin composition comprising:
- a resin component, and
- a cyanato group-containing cyclic phosphazene compound represented by the following formula (1):
- in the formula (1), n represents an integer of 3 to 15, A represents a group selected from the group consisting of an A1 group, an A2 group and an A3 group shown below, and at least one group is an A3 group:
- A1 group:
- an alkoxy group having 1 to 8 carbon atoms which may be substituted with at least one group selected from an alkyl group having 1 to 6 carbon atoms, an alkenyl group and an aryl group,
- A2 group:
- an aryloxy group having 6 to 20 carbon atoms which may be substituted with at least one group selected from an alkyl group having 1 to 6 carbon atoms, an alkenyl group and an aryl group, and
- A3 group:
- a group selected from the group consisting of a cyanatophenyloxy group represented by the formula (2) shown below, a cyanatophenyl-substituted phenyloxy group represented by the formula (3) shown below, a cyanatophenyl-substituted phenyloxy group represented by the formula (4) shown below, a cyanatophenyl-substituted indanoxy group represented by the formula (5) shown below and a cyanatoindane-substituted phenyloxy group represented by the formula (6) shown below:
- in the formula (4), Y represents O, S, SO2, CH2, CHCH3, C(CH3)2, C(CF3)2, C(CH3)CH2CH3 or CO,
- in the formulas (5) and (6), R1 and R2 represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group or a phenyl group.
8 more elements
A resin molded product made of a resin composition comprising a resin component and a cyanato group-containing cyclic phosphazene compound represented by the following formula (1):
- in the formula (1), n represents an integer of 3 to 15, A represents a group selected from the group consisting of an A1 group, an A2 group and an A3 group shown below, and at least one group is an A3 group:
- A1 group:
- an alkoxy group having 1 to 8 carbon atoms which may be substituted with at least one group selected from an alkyl group having 1 to 6 carbon atoms, an alkenyl group and an aryl group,
- A2 group:
- an aryloxy group having 6 to 20 carbon atoms which may be substituted with at least one group selected from an alkyl group having 1 to 6 carbon atoms, an alkenyl group and an aryl group, and
- A3 group:
- a group selected from the group consisting of a cyanatophenyloxy group represented by the formula (2) shown below, a cyanatophenyl-substituted phenyloxy group represented by the formula (3) shown below, a cyanatophenyl-substituted phenyloxy group represented by the formula (4) shown below, a cyanatophenyl-substituted indanoxy group represented by the formula (5) shown below and a cyanatoindane-substituted phenyloxy group represented by the formula (6) shown below:
- in the formula (4), Y represents O, S, SO2, CH2, CHCH3, C(CH3)2, C(CF3)2, C(CH3)CH2CH3 or CO,
- in the formulas (5) and (6), R1 and R2 represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group or a phenyl group.
6 more elements
A polymerizable composition comprising a cyanato group-containing cyclic phosphazene compound represented by the following formula (1):
- in the formula (1), n represents an integer of 3 to 15, A represents a group selected from the group consisting of an A1 group, an A2 group and an A3 group shown below, and at least one group is an A3 group:
- A1 group:
- an alkoxy group having 1 to 8 carbon atoms which may be substituted with at least one group selected from an alkyl group having 1 to 6 carbon atoms, an alkenyl group and an aryl group,
- A2 group:
- an aryloxy group having 6 to 20 carbon atoms which may be substituted with at least one group selected from an alkyl group having 1 to 6 carbon atoms, an alkenyl group and an aryl group, and
- A3 group:
- a group selected from the group consisting of a cyanatophenyloxy group represented by the formula (2) shown below, a cyanatophenyl-substituted phenyloxy group represented by the formula (3) shown below, a cyanatophenyl-substituted phenyloxy group represented by the formula (4) shown below, a cyanatophenyl-substituted indanoxy group represented by the formula (5) shown below and a cyanatoindane-substituted phenyloxy group represented by the formula (6) shown below:
- in the formula (4), Y represents O, S, SO2, CH2, CHCH3, C(CH3)2, C(CF3)2, C(CH3) CH2CH3 or CO,
- in the formulas (5) and (6), R1 and R2 represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group or a phenyl group.
6 more elements
A resin molded product made of a polymer of a polymerizable composition comprising a cyanato group-containing cyclic phosphazene compound represented by the following formula (1):
- in the formula (1), n represents an integer of 3 to 15, A represents a group selected from the group consisting of an A1 group, an A2 group and an A3 group shown below, and at least one group is an A3 group:
- A1 group:
- an alkoxy group having 1 to 8 carbon atoms which may be substituted with at least one group selected from an alkyl group having 1 to 6 carbon atoms, an alkenyl group and an aryl group,
- A2 group:
- an aryloxy group having 6 to 20 carbon atoms which may be substituted with at least one group selected from an alkyl group having 1 to 6 carbon atoms, an alkenyl group and an aryl group, and
- A3 group:
- a group selected from the group consisting of a cyanatophenyloxy group represented by the formula (2) shown below, a cyanatophenyl-substituted phenyloxy group represented by the formula (3) shown below, a cyanatophenyl-substituted phenyloxy group represented by the formula (4) shown below, a cyanatophenyl-substituted indanoxy group represented by the formula (5) shown below and a cyanatoindane-substituted phenyloxy group represented by the formula (6) shown below:
- in the formula (4), Y represents O, S, SO2, CH2, CHCH3, C(CH3)2, C(CF3)2, C(CH3)CH2CH3 or CO,
- in the formulas (5) and (6), R1 and R2 represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group or a phenyl group.
6 more elements
Dependencies are inferred from the claim text.