KR102629376B1 - 조성물, 경화물 및 경화물의 제조 방법 - Google Patents
조성물, 경화물 및 경화물의 제조 방법 Download PDFInfo
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- KR102629376B1 KR102629376B1 KR1020197035706A KR20197035706A KR102629376B1 KR 102629376 B1 KR102629376 B1 KR 102629376B1 KR 1020197035706 A KR1020197035706 A KR 1020197035706A KR 20197035706 A KR20197035706 A KR 20197035706A KR 102629376 B1 KR102629376 B1 KR 102629376B1
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- 239000000203 mixture Substances 0.000 title claims abstract description 208
- 238000004519 manufacturing process Methods 0.000 title claims description 83
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 415
- 150000001875 compounds Chemical class 0.000 claims abstract description 285
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 154
- 229940126062 Compound A Drugs 0.000 claims abstract description 105
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- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 55
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 16
- 125000001424 substituent group Chemical group 0.000 claims description 111
- 125000003118 aryl group Chemical group 0.000 claims description 107
- 125000000623 heterocyclic group Chemical group 0.000 claims description 90
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 62
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 61
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 59
- 125000005647 linker group Chemical group 0.000 claims description 40
- 125000005843 halogen group Chemical group 0.000 claims description 35
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- 125000004429 atom Chemical group 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
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- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
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- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
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- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
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- 239000002562 thickening agent Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical class S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
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- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
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- NLSXASIDNWDYMI-UHFFFAOYSA-N triphenylsilanol Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(O)C1=CC=CC=C1 NLSXASIDNWDYMI-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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Classifications
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- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
- C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety
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- C08K5/00—Use of organic ingredients
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- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/07—Aldehydes; Ketones
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3472—Five-membered rings
- C08K5/3475—Five-membered rings condensed with carbocyclic rings
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- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
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Abstract
(식 중의 부호는 명세서를 참조)
Description
Claims (9)
- 하기 일반식(A1), (A2) 또는 (A3)으로 나타내는 화합물 A와,
하기 일반식(B)로 나타내는 화합물 B를 포함하는 조성물.
(식 중 R1 및 R2는 각각 독립적으로, 수소 원자, 할로겐 원자, 시아노기, 수산기, 니트로기, 카르복실기, 탄소 원자수 1~40의 알킬기, 탄소 원자수 6~20의 아릴기, 탄소 원자수 7~20의 아릴알킬기, 탄소 원자수 2~20의 복소환함유기 또는 -O-R9를 나타내고,
R1 및 R2 중 적어도 한쪽은 상기 -O-R9이며,
R3 및 R4는 각각 독립적으로 할로겐 원자, 시아노기, 수산기, 니트로기, 카르복실기, 탄소 원자수 1~40의 알킬기, 탄소 원자수 6~20의 아릴기, 탄소 원자수 7~20의 아릴알킬기 또는 탄소 원자수 2~20의 복소환함유기를 나타내고,
R9는 탄소 원자수 1~20의 알킬기, 탄소 원자수 2~20의 알케닐기, 탄소 원자수 6~20의 아릴기, 탄소 원자수 7~20의 아릴알킬기, 탄소 원자수 2~20의 복소환함유기 또는 트리알킬실릴기를 나타내며, 상기 알킬기, 아릴기, 아릴알킬기, 복소환함유기 및 트리알킬실릴기 중의 메틸렌기는 탄소-탄소 이중결합, -O-, -S-, -CO-, -O-CO-, -CO-O-, -O-CO-O-, -O-CO-O-, -S-CO-, -CO-S-, -S-CO-O-, -O-CO-S-, -CO-NH-, -NH-CO-, -NH-CO-O-, -NR'-, >P=O, -S-S-, -SO2- 또는 이들의 조합으로 치환되어 있는 경우가 있고,
상기 알킬기, 아릴기, 아릴알킬기, 복소환함유기 및 트리알킬실릴기는 치환기를 가지고 있는 경우가 있으며,
R'는 수소 원자 또는 탄소 원자수 1~8의 알킬기를 나타내고,
복수의 R3끼리 및 복수의 R4끼리는 각각 결합하여 벤젠환 또는 나프탈렌환을 형성하고 있는 경우가 있으며,
복수의 R3 및 복수의 R4는 각각 동일한 경우도 있고 다른 경우도 있으며,
m1은 1~10의 정수를 나타내고,
a1은 0~4의 정수를 나타내며,
a2는 0~2의 정수를 나타내고,
Xa1은 직접결합 또는 m1가의 원자 혹은 결합기를 나타낸다.)
(식 중 R1' 및 R2'는 각각 독립적으로 수소 원자, 할로겐 원자, 시아노기, 수산기, 니트로기, 카르복실기, 탄소 원자수 1~40의 알킬기, 탄소 원자수 6~20의 아릴기, 탄소 원자수 7~20의 아릴알킬기, 탄소 원자수 2~20의 복소환함유기 또는 -O-R9를 나타내고,
R1' 및 R2' 중 적어도 한쪽은 상기 -O-R9이며,
R5 및 R6은 각각 독립적으로 할로겐 원자, 시아노기, 수산기, 니트로기, 카르복실기, 탄소 원자수 1~40의 알킬기, 탄소 원자수 6~20의 아릴기, 탄소 원자수 7~20의 아릴알킬기 또는 탄소 원자수 2~20의 복소환함유기를 나타내고,
R9는 식(A1)과 같은 의미이며,
상기 알킬기, 아릴기, 아릴알킬기, 복소환함유기 및 트리알킬실릴기 중의 메틸렌기는 탄소-탄소 이중결합, -O-, -S-, -CO-, -O-CO-, -CO-O-, -O-CO-O-, -O-CO-O-, -S-CO-, -CO-S-, -S-CO-O-, -O-CO-S-, -CO-NH-, -NH-CO-, -NH-CO-O-, -NR'-, >P=O, -S-S-, -SO2- 또는 이들의 조합으로 치환되어 있는 경우가 있고,
상기 알킬기, 아릴기, 아릴알킬기, 복소환함유기 및 트리알킬실릴기는 치환기를 가지고 있는 경우가 있으며,
R'는 수소 원자 또는 탄소 원자수 1~8의 알킬기를 나타내고,
복수의 R5끼리 및 복수의 R6끼리는 각각 결합하여 벤젠환 또는 나프탈렌환을 형성하고 있는 경우가 있으며,
복수의 R5 및 복수의 R6은 각각 동일한 경우도 있고 다른 경우도 있으며,
m2는 1~10의 정수를 나타내고,
a3은 0~4의 정수를 나타내며,
a4는 0~3의 정수를 나타내고,
Xa2는 직접결합 또는 m2가의 원자 혹은 결합기를 나타낸다.)
(식 중 R1" 및 R2"의 한쪽은 -O-R9이며, 다른 쪽은 -O-R9, 수소 원자, 수산기, 탄소 원자수 1~40의 알킬기, 탄소 원자수 6~20의 아릴기, 탄소 원자수 7~20의 아릴알킬기 또는 탄소 원자수 2~20의 복소환함유기이고,
R9는 -CO-O-R300이고, R300은 탄소 원자수 1~19의 알킬기 또는 탄소 원자수 2~19의 알케닐기이고,
R7 및 R8은 각각 독립적으로 할로겐 원자, 시아노기, 수산기, 니트로기, 카르복실기, 탄소 원자수 1~40의 알킬기, 탄소 원자수 6~20의 아릴기, 탄소 원자수 7~20의 아릴알킬기 또는 탄소 원자수 2~20의 복소환함유기를 나타내고,
상기 알킬기, 아릴기, 아릴알킬기, 복소환함유기 및 트리알킬실릴기 중의 메틸렌기는 탄소-탄소 이중결합, -O-, -S-, -CO-, -O-CO-, -CO-O-, -O-CO-O-, -O-CO-O-, -S-CO-, -CO-S-, -S-CO-O-, -O-CO-S-, -CO-NH-, -NH-CO-, -NH-CO-O-, -NR'-, >P=O, -S-S-, -SO2- 또는 이들의 조합으로 치환되어 있는 경우가 있고,
상기 알킬기, 아릴기, 아릴알킬기, 복소환함유기 및 트리알킬실릴기는 치환기를 가지고 있는 경우가 있으며,
R'는 수소 원자 또는 탄소 원자수 1~8의 알킬기를 나타내고,
복수의 R7끼리는 결합하여 벤젠환 또는 나프탈렌환을 형성하고 있는 경우가 있으며,
복수의 R7 및 복수의 R8은 각각 동일한 경우도 있고 다른 경우도 있으며,
m3은 1~3의 정수를 나타내고,
a5는 0~3의 정수를 나타내며,
a6은 0~3-m3의 정수를 나타낸다.
단, 하기 (1) 또는 (2)를 만족한다.
(1) m3은 1 또는 2이다.
(2) m3이 3일 때, a5는 2이고, R7 중 하나는 치환기를 가지고 있지 않은 탄소 원자수 1~20의 알콕시기, 또는 치환기로서 에틸렌성 불포화기를 적어도 가지는, 탄소 원자수 1~20의 알콕시기이고, R7 중 다른 쪽은 탄소 원자수 1~40의 알킬기이다.)
(식 중 R11은 탄소 원자수 1~20의 알킬기, 탄소 원자수 2~20의 알케닐기, 탄소 원자수 6~20의 아릴기, 탄소 원자수 7~20의 아릴알킬기, 탄소 원자수 2~20의 복소환함유기 또는 트리알킬실릴기를 나타내고,
R12 및 R13은 각각 독립적으로 수소 원자 또는 탄소 원자수 1~40의 알킬기를 나타내며,
R14는 할로겐 원자, 시아노기, 수산기, 니트로기, 카르복실기, 탄소 원자수 1~40의 알킬기, 탄소 원자수 6~20의 아릴기, 탄소 원자수 7~20의 아릴알킬기 또는 탄소 원자수 2~20의 복소환함유기를 나타내고,
상기 알킬기, 아릴기, 아릴알킬기, 복소환함유기 및 트리알킬실릴기 중의 메틸렌기는 탄소-탄소 이중결합, -O-, -S-, -CO-, -O-CO-, -CO-O-, -O-CO-O-, -O-CO-O-, -S-CO-, -CO-S-, -S-CO-O-, -O-CO-S-, -CO-NH-, -NH-CO-, -NH-CO-O-, -NR'-, >P=O, -S-S-, -SO2- 또는 이들의 조합으로 치환되어 있는 경우가 있으며,
상기 알킬기, 아릴기, 아릴알킬기, 복소환함유기 및 트리알킬실릴기는 치환기를 가지고 있는 경우가 있고,
R'는 수소 원자 또는 탄소 원자수 1~8의 알킬기를 나타내며,
복수의 R14끼리는 결합하여 벤젠환 또는 나프탈렌환을 형성하고 있는 경우가 있고,
복수의 R14는 각각 동일한 경우도 있고 다른 경우도 있으며,
n은 1~10의 정수를 나타내고,
b1은 0~2의 정수를 나타내며,
Xb는 직접결합 또는 n가의 원자 혹은 결합기를 나타낸다.) - 제1항에 있어서,
일반식(A3)에서, R1" 및 R2" 중 적어도 한쪽은 -O-COO-t부틸이고, 다른 쪽은 수소 원자인, 조성물. - 제1항에 있어서,
일반식(A3)에서 m3이 3일 때,
2개 존재하는 R7 중 하나는, -O-COO-t부틸인 R1" 또는 R2"에 대해 오르토위에 존재하는, 탄소 원자수 1~40의 알킬기이며,
다른 하나는, 상기 알킬기에 대하여 오르토위에 존재하는, 치환기를 가지고 있지 않은 탄소 원자수 1~20의 알콕시기, 또는 치환기로서 에틸렌성 불포화기를 적어도 가지는, 탄소 원자수 1~20의 알콕시기인, 조성물. - 제3항에 있어서,
일반식(A3)에서 m3이 3일 때,
2개 존재하는 R7 중 하나는, -O-COO-t부틸인 R1" 또는 R2"에 대해 오르토위에 존재하는 메틸기인, 조성물. - 제1항 또는 제2항에 있어서,
상기 R9 및 R11은 산소 원자 측의 말단의 메틸렌기가 -CO-O-로 치환되어 있는 탄소 원자수 1~20의 알킬기인, 조성물. - 제1항 또는 제2항에 있어서,
상기 화합물 A의 함유량이 상기 화합물 A 및 상기 화합물 B의 합계 100질량부에 대하여 1질량부 이상 99질량부 이하인, 조성물. - 제1항 또는 제2항에 있어서,
중합성 화합물을 포함하는, 조성물. - 제7항에 기재된 조성물의 경화물.
- 제7항에 기재된 조성물의 경화물을 형성하는 공정을 가지는, 경화물의 제조 방법.
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