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US 2019/0055357 A1Published application
Polymer, composition, molded article, cured product and laminate
AssigneeJsr Corporation
InventorsRyouyuu HIFUMI, Toshiaki Kadota, Nobuyuki Miyaki, Shintarou Fujitomi, Yasutaka Yoshida, Ryouji Tatara
Life of this patent
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Abstract
A novel polymer having high glass transition temperature and an excellent balance between heat resistance, high refractive index and mechanical properties, and a composition and molded article containing the polymer are provided. The polymer according to the invention has a first structural unit represented by at least one of formulae (1-1), (1-2) and (1-3) below and a second structural unit having either a secondary amino structure or a tertiary amino structure at two or more terminals.
Claims14
1:
- A polymer comprising:
- a first structural unit represented by at least one of formulae (1-1), (1-2) and (1-3) below;
- and
- a second structural unit having either a secondary amino structure or a tertiary amino structure at two or more terminals,
- wherein in formulae (1-1) to (1-3), R1 is each independently a halogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, a nitro group, a cyano group, any of primary to tertiary amino groups or a salt of any of primary to tertiary amino groups;
- n is each independently an integer of 0 to 2;
- and when n is 2, two or more R1 may be the same or different and may be joined together in any combination to form a part of a cyclic structure.
4 more elements
2:
- The polymer according to claim 1, wherein the second structural unit is a structural unit represented by formula (2-A) below
- wherein in formula (2-A), R2 and R3 are respectively and independently a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms;
- and X is a bivalent organic group.
3:
- The polymer according to claim 2, wherein X in formula (2-A) is a group represented by formulae (2-1) to (2-8) below, a bivalent hydrocarbon group having 1 to 20 carbon atoms, a bivalent halogenated hydrocarbon group having 1 to 20 carbon atoms or a 3- to 10-membered bivalent heterocyclic group
- wherein in formula (2-1), R4 and R5 are respectively and independently a halogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, a nitro group, a cyano group, a carboxy group, a sulfonic acid group, a phosphonic acid group, a phosphoric acid group, a hydroxy group, any of primary to tertiary amino groups, a salt of carboxy group, a salt of sulfo group, a salt of phosphonic acid group, a salt of phosphate group, a salt of hydroxy group or a salt of any of primary to tertiary amino groups;
- c and d are respectively and independently an integer of 0 to 2;
- a and b are respectively and independently an integer of 0 to 8;
- when a is 2 or more, two or more R4 may be the same or different and may be joined together in any combination to form a part of a cyclic structure;
- when b is 2 or more, two or more R5 may be the same or different and may be joined together in any combination to form a part of a cyclic structure;
- Q and Z are respectively and independently a single bond, —O—, —S— or —N(R17)—;
- R17 is a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms or a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms;
- L is a single bond or a bivalent organic group;
- y is an integer of 0 to 5;
- when y is 2 or more, two or more Q, L and Z may be respectively the same or different;
- when y is 2 or more and a is 1 or more, two or more R4 may be the same or different;
- R6 and R7 are respectively and independently a single bond, a methylene group or an alkylene group having 2 to 4 carbon atoms;
- wherein in formula (2-2), Ra and Rb are respectively and independently a 5- to 30-membered bivalent alicyclic hydrocarbon skeleton;
- R8 and R9 are respectively and independently a halogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, a nitro group, a cyano group, a carboxy group, a sulfonic acid group, a phosphonic acid group, a phosphoric acid group, a hydroxy group, any of primary to tertiary amino groups, a salt of carboxy group, a salt of sulfo group, a salt of phosphonic acid group, a salt of phosphate group, a salt of hydroxy group or a salt of any of primary to tertiary amino groups;
- e and f are respectively and independently an integer of 0 to 20;
- when e is 2 or more, two or more R8 may be the same or different and may be joined together in any combination to form a part of a cyclic structure;
- when f is 2 or more, two or more R9 may be the same or different and may be joined together in any combination to form a part of a cyclic structure;
- Q and Z are respectively and independently a single bond, —O—, —S— or —N(R8)—;
- R1′ is a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms or a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms;
- L is a single bond or a bivalent organic group;
- y is an integer of 0 to 5;
- when y is 2 or more, two or more Q, L and Z may be respectively the same or different;
- when y is 2 or more and e is 1 or more, two or more R8 may be the same or different;
- R10 and R11 are respectively and independently a single bond, a methylene group or an alkylene group having 2 to 4 carbon atoms;
- wherein in formula (2-3), R12 is a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms or a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms;
- R13 and R14 are respectively and independently a bivalent linear or alicyclic hydrocarbon group having 1 to 20 carbon atoms or a bivalent linear or alicyclic halogenated hydrocarbon group having 1 to 20 carbon atoms;
- g is 0 or 1;
- h is an integer of 1 to 10;
- and when h is 2 or more, two or more R12 and R14 may be respectively the same or different;
- wherein in formula (2-4), R15 and R16 are respectively and independently a bivalent linear or alicyclic hydrocarbon group having 1 to 20 carbon atoms or a bivalent linear or alicyclic halogenated hydrocarbon group having 1 to 20 carbon atoms;
- i is 0 or 1;
- j is an integer of 1 to 10;
- and when j is 2 or more, two or more R16 may be the same or different;
- wherein in formula (2-5), R21 and R22 are respectively and independently a halogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, a nitro group, a cyano group, a carboxy group, a sulfonic acid group, a phosphonic acid group, a phosphoric acid group, a hydroxy group, any of primary to tertiary amino groups, a salt of carboxy group, a salt of sulfo group, a salt of phosphonic acid group, a salt of phosphate group, a salt of hydroxy group or a salt of any of primary to tertiary amino groups;
- k and 1 are respectively and independently an integer of 0 to 3;
- when k is 2 or 3, two or more R21 may be the same or different;
- when 1 is 2 or 3, two or more R22 may be the same or different;
- R23 is a single bond, —O—, —S—, —C(O)—, —S(O)— or —S(O)2—;
- wherein in formula (2-6), R24 and R25 are respectively and independently a halogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, a nitro group, a cyano group, a carboxy group, a sulfonic acid group, a phosphonic acid group, a phosphoric acid group, a hydroxy group, any of primary to tertiary amino groups, a salt of carboxy group, a salt of sulfo group, a salt of phosphonic acid group, a salt of phosphate group, a salt of hydroxy group or a salt of any of primary to tertiary amino groups;
- m and n are respectively and independently an integer of 0 to 3;
- when m is 2 or 3, two or more R24 may be the same or different;
- when n is 2 or more, two or more R25 may be the same or different;
- R26 and R27 are respectively and independently a single bond, —O—, —S—, —C(O)—, —S(O)— or —S(O)2—;
- wherein in formula (2-7), R28 and R29 are respectively and independently a halogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, a nitro group, a cyano group, a carboxy group, a sulfonic acid group, a phosphonic acid group, a phosphoric acid group, a hydroxy group, any of primary to tertiary amino groups, a salt of carboxy group, a salt of sulfo group, a salt of phosphonic acid group, a salt of phosphate group, a salt of hydroxy group or a salt of any of primary to tertiary amino groups;
- o is an integer of 0 to 3;
- p is an integer of 0 to 4;
- when o is 2 or more, two or more R28 may be the same or different;
- when p is 2 or more, two or more R29 may be the same or different;
- n is an integer of 0 to 6;
- R30 is a monovalent hydrocarbon group having 1 to 20 carbon atoms or a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms;
- q is an integer of 0 to 15;
- when q is 2 or more, two or more R30 may be the same or different;
- and
- wherein in formula (2-8), R31 and R32 are respectively and independently a halogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, a nitro group, a cyano group, a carboxy group, a sulfonic acid group, a phosphonic acid group, a phosphoric acid group, a hydroxy group, any of primary to tertiary amino groups, a salt of carboxy group, a salt of sulfo group, a salt of phosphonic acid group, a salt of phosphate group, a salt of hydroxy group or a salt of any of primary to tertiary amino groups;
- r and s are respectively and independently an integer of 0 to 4;
- when r is 2 or more, two or more R31 may be the same or different;
- when s is 2 or more, two or more R32 may be the same or different;
- m is an integer of 1 to 5;
- n is an integer of 0 to 5;
- R33 is a monovalent hydrocarbon group having 1 to 20 carbon atoms or a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms;
- t is an integer of 0 to 20;
- when t is 2 or more, two or more R33 may be the same or different.
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4:
- The polymer according to claim 3, wherein X in the formula (2-A) is a group represented by formulae (2-1) to (2-4), a bivalent hydrocarbon group having 1 to 20 carbon atoms, a bivalent halogenated hydrocarbon group having 1 to 20 carbon atoms or a 3- to 10-membered bivalent heterocyclic group.
5:
- The polymer according to claim 1, wherein a weight average molecular weight of the polymer based on polystyrene is 500 to 600,000 inclusive.
6:
- A polymer comprising:
- a first structural unit represented by at least one of formulae (1-1), (1-2) and (1-3) below;
- and
- a third structural unit represented by at least one of formulae (3-1) and (3-2) below:
- wherein in formulae (1-1) to (1-3), R1 is each independently a halogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, a nitro group, a cyano group, any of primary to tertiary amino groups or a salt of any of primary to tertiary amino groups;
- n is each independently an integer of 0 to 2;
- when n is 2, two or more R1 may be the same or different and may be joined together in any combination to form a part of a cyclic structure;
- wherein in formulae (3-1) and (3-2), R2 and R3 are respectively and independently a halogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, a nitro group or a cyano group;
- e and f are respectively and independently an integer of 0 to 2;
- a and b are respectively and independently an integer of 0 to 8;
- when a is 2 or more, two or more R2 may be the same or different and may be joined together in any combination to form a part of a cyclic structure;
- when b is 2 or more, two or more R3 may be the same or different and may be joined together in any combination to form a part of a cyclic structure;
- Z1 to Z4 are respectively and independently —O— or —S—;
- R5 and R6 are respectively and independently a methylene group or an alkylene group having 2 to 4 carbon atoms;
- v is an integer of 0 to 2;
- when v is 2, two R5 may be the same or different and two Z1 may be the same or different;
- w is an integer of 0 to 2;
- when w is 2, two R6 may be the same or different and two Z4 may be the same or different;
- G is —O—, —S—, —C═O—, —SO— or —SO2—;
- L is a bivalent group represented by formula (L-1) or (L-2) below;
- y is an integer of 1 to 3;
- when y is 2 or more, two or more L may be the same or different;
- when y is 2 or more and a is 1 or more, two or more R2 may be the same or different;
- wherein in formulae (L-1) and (L-2), A is each independently —C(O)—, —SO— or —SO2—;
- B is each independently —O—, —S— or —N(R8)—;
- R8 is a hydrogen atom, a halogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms or a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms;
- R7 is each independently a halogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, a nitro group or a cyano group, 1 is each independently an integer of 0 to 2;
- s is each independently an integer of 0 to 8;
- when s is 2 or more, two or more R7 may be the same or different and may be joined together in any combination to form a part of a cyclic structure;
- and “*” indicates a bond.
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7:
- The polymer according to claim 6, wherein the third structural unit is represented by formula (3-1).
8:
- A composition comprising:
- a polymer having a structural unit represented by at least one of formulae (1-1), (1-2) and (1-3) below;
- and
- a curable compound,
- wherein in formulae (1-1) to (1-3), R1 is each independently a halogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, a nitro group, a cyano group, any of primary to tertiary amino groups or a salt of any of primary to tertiary amino groups;
- n is each independently an integer of 0 to 2;
- and when n is 2, two or more R1 may be the same or different and may be joined together in any combination to form a part of a cyclic structure.
4 more elements
9:
- The composition according to claim 8, wherein the curable compound is at least one selected from the group consisting of an epoxy compound, a cyanate ester compound, a vinyl compound, a silicone compound, an oxazine compound, a maleimide compound and an allyl compound.
10:
- The composition according to claim 8, further comprising a curing auxiliary agent.
11:
- A composition, comprising the polymer according to claim 1 and an organic solvent.
12:
- A molded article, comprising the polymer according to claim 1.
13:
- A cured product obtained by curing the composition according to claim 8.
14:
- A laminate comprising:
- a substrate;
- and
- a cured product layer formed on the substrate by using the composition according to claim 8.
1 more element