Curable compound

Patent metadata

Field	Value
Publication number	US-11021438-B2
Application number	US-201716470057-A
Country	US
Kind code	B2
Filing date	Nov 10, 2017
Priority date	Dec 16, 2016
Publication date	Jun 1, 2021
Grant date	Jun 1, 2021

Abstract

There is provided a curable compound having good solvent solubility and being capable of forming a cured material having super heat resistance. The curable compound according to the present invention is represented by the following formula (1). In the formula (1), R 1 and R 2 each represent a curable functional group; D 1 and D 2 each represent a single bond or a linking group; and L represents a divalent group having a repeating unit containing a structure represented by the following formula (I) and a structure represented by the following formula (II) (wherein Ar 1 to Ar 3 each represent a group made by eliminating two hydrogen atoms from a structural formula of an aromatic ring or a group made by eliminating two hydrogen atoms from a structural formula in which two or more aromatic rings are bound through a single bond or a linking group; X represents —CO—, —S— or —SO 2 —; each Y represents —S—, —SO 2 —, —O—, —CO—, —COO— or —CONH—; and n represents an integer of 0 or more):

First claim

The invention claimed is:

1. A curable compound represented by the following formula (1):

wherein R 1 and R 2 are identical or different and each represent a curable functional group; D 1 and D 2 are 1,4-phenylene group; and L represents a divalent group represented by the following formula (1-1):

wherein Ar 1 to Ar 3 are identical or different and each represent a group made by eliminating two hydrogen atoms from a structural formula of an aromatic ring or a group made by eliminating two hydrogen atoms from a structural formula in which two or more aromatic rings are bound through a single bond or a linking group; X represents —CO—, —S— or —SO 2 —; each Y is identical or different and represents —S—, —SO 2 —, —O—, —CO—, —COO— or —CONH—; n represents an integer of 0 or more; and m1 represents 3 to 40,
wherein the curable functional group is represented by the following formula (r):

wherein the bond extending from the nitrogen atom in formula (r) is bound to D 1 or D 2 , each Q represents C or CH, and Q optionally forms a double bond, n′ is an integer of 0 to 3, R 3 to R 6 are identical or different, and each R 3 to R 6 represent a hydrogen atom, a saturated or unsaturated aliphatic hydrocarbon group, an aromatic hydrocarbon group, or a group in which two or more groups selected from the saturated or unsaturated aliphatic hydrocarbon group and the aromatic hydrocarbon group are bound, two groups selected from R 3 to R 6 are optionally bound to each other to form a ring with neighboring carbon atoms, and
wherein the linking group represents divalent hydrocarbon groups having 1 to 5 carbon atoms or groups made by replacing one or more hydrogen atoms of the divalent hydrocarbon group having 1 to 5 carbon atoms with halogen atoms.

2. The curable compound according to claim 1 , wherein R 1 and R 2 in the formula (1) are identical or different and are each a group selected from groups represented by the following formulas (r-1) to (r-6):

wherein a bond extending from a nitrogen atom in the formulas is bound to D 1 or D 2 .

3. The curable compound according to claim 1 , wherein Ar 1 to Ar 3 in the formula (I-1) are identical or different and are each a group made by eliminating two hydrogen atoms from a structural formula of an aromatic ring having 6 to 14 carbon atoms, or a group made by eliminating two hydrogen atoms from a structural formula in which two or more aromatic rings having 6 to 14 carbon atoms are bound through a single bond, a straight-chain or branched-chain alkylene group having 1 to 5 carbon atoms or a group made by replacing one or more hydrogen atoms of a straight-chain or branched-chain alkylene group having 1 to 5 carbon atoms with halogen atoms.

4. The curable compound according to claim 1 , wherein the structure represented by the following formula (I) is a structure derived from benzophenone

5. The curable compound according to claim 4 , wherein a proportion of an amount of a structural unit derived from benzophenone to a total amount of the curable compound represented by the formula (1) is 5% by weight or more.

6. The curable compound according to claim 1 , wherein the structure represented by the following formula (II) is a structure derived from at least one compound selected from hydroquinone, resorcinol, 2,6-naphthalenediol, 2,7-naphthalenediol, 4,4′-dihydroxybiphenyl, 4,4′-dihydroxydiphenyl ether, 4,4′-dihydroxybenzophenone, 4,4′-dihydroxydiphenyl sulfide, 4,4′-dihydroxydiphenyl sulfone and bisphenol A

7. The curable compound according to claim 6 , wherein a proportion of an amount of a structural unit derived from hydroquinone, resorcinol and bisphenol A to a total amount of the curable compound represented by the formula (1) is 5% by weight or more.

8. A curable composition comprising a curable compound according to claim 1 .

9. A cured material of a curable composition according to claim 8 .

10. A molding comprising a cured material according to claim 9 .

11. The curable compound according to claim 1 , wherein R 1 and R 2 in the formula (1) are identical or different and are each a group selected from groups represented by the following formulas (r-1) and (r-5):

wherein a bond extending from a nitrogen atom in the formulas is bound to D 1 or D 2 .

Assignees

• Daicel Corp

Inventors

• Yang Fei
• Okano Yoshimichi
• Nakatani Kouji
• Liu Feng
• Nakai Michiyo
• Yaegashi Takayuki
• Okamoto Yusuke
• Yoshida Tsukasa

Classifications

• C07D207/452

  with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom · CPC title

• C07D209/48 Primary

  with oxygen atoms in positions 1 and 3, e.g. phthalimide · CPC title

• C07D209/50

  with oxygen and nitrogen atoms in positions 1 and 3 · CPC title

• C07D207/456

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms · CPC title

• C08G73/126

  the unsaturated precursors being wholly aromatic · CPC title