JP7229527B2 - ジイミドジカルボン酸およびそれを用いたエポキシ樹脂硬化物 - Google Patents
ジイミドジカルボン酸およびそれを用いたエポキシ樹脂硬化物 Download PDFInfo
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- JP7229527B2 JP7229527B2 JP2019092240A JP2019092240A JP7229527B2 JP 7229527 B2 JP7229527 B2 JP 7229527B2 JP 2019092240 A JP2019092240 A JP 2019092240A JP 2019092240 A JP2019092240 A JP 2019092240A JP 7229527 B2 JP7229527 B2 JP 7229527B2
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- epoxy resin
- diamine
- carbon atoms
- dicarboxylic acid
- reaction
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- 239000003822 epoxy resin Substances 0.000 title claims description 102
- 229920000647 polyepoxide Polymers 0.000 title claims description 102
- 239000002253 acid Substances 0.000 title claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 46
- 150000004985 diamines Chemical class 0.000 claims description 37
- 238000006243 chemical reaction Methods 0.000 claims description 30
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 22
- 150000008064 anhydrides Chemical class 0.000 claims description 21
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims description 20
- 229910000071 diazene Inorganic materials 0.000 claims description 20
- -1 docosane Diamine Chemical class 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 11
- 239000000539 dimer Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 7
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical group OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 7
- 150000002430 hydrocarbons Chemical group 0.000 claims description 3
- WTKALCXKBKEKTL-UHFFFAOYSA-N CCCCCCCCCCCCCCCCCCCCC(N)N Chemical compound CCCCCCCCCCCCCCCCCCCCC(N)N WTKALCXKBKEKTL-UHFFFAOYSA-N 0.000 claims description 2
- QNTIPRAMJVCLOP-UHFFFAOYSA-N icosane-1,1-diamine Chemical compound CCCCCCCCCCCCCCCCCCCC(N)N QNTIPRAMJVCLOP-UHFFFAOYSA-N 0.000 claims description 2
- HOWGUJZVBDQJKV-UHFFFAOYSA-N n-propyl-nonadecane Natural products CCCCCCCCCCCCCCCCCCCCCC HOWGUJZVBDQJKV-UHFFFAOYSA-N 0.000 claims description 2
- GYMBMZSWTJBJPE-UHFFFAOYSA-N nonadecane-1,1-diamine Chemical compound CCCCCCCCCCCCCCCCCCC(N)N GYMBMZSWTJBJPE-UHFFFAOYSA-N 0.000 claims description 2
- YNVQYOQLKGNUBZ-UHFFFAOYSA-N octadecane-1,1-diamine Chemical group CCCCCCCCCCCCCCCCCC(N)N YNVQYOQLKGNUBZ-UHFFFAOYSA-N 0.000 claims description 2
- FNXVLESIGLBAQC-UHFFFAOYSA-N C(CCCCCCCCCCCCCCCCCCCCCCCCCCC)(N)N Chemical compound C(CCCCCCCCCCCCCCCCCCCCCCCCCCC)(N)N FNXVLESIGLBAQC-UHFFFAOYSA-N 0.000 claims 1
- NQZHBAHTUIDZLN-UHFFFAOYSA-N NC(CCCCCCCCCCCCCCCCCCCCCCCCC)N Chemical compound NC(CCCCCCCCCCCCCCCCCCCCCCCCC)N NQZHBAHTUIDZLN-UHFFFAOYSA-N 0.000 claims 1
- LJAMIZJLDPYKST-UHFFFAOYSA-N pentacosane-1,1-diamine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCC(N)N LJAMIZJLDPYKST-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 27
- 238000000034 method Methods 0.000 description 19
- 125000000524 functional group Chemical group 0.000 description 11
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 10
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 10
- 239000002994 raw material Substances 0.000 description 10
- 238000004566 IR spectroscopy Methods 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- 238000002835 absorbance Methods 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 238000011978 dissolution method Methods 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
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- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000002950 deficient Effects 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004962 Polyamide-imide Substances 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 229920003055 poly(ester-imide) Polymers 0.000 description 2
- 229920002312 polyamide-imide Polymers 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- ZCEHQPCGOUBSJR-UHFFFAOYSA-N 1,3-dioxo-2-benzofuran-4-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=C1C(=O)OC2=O ZCEHQPCGOUBSJR-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- BJQWYEJQWHSSCJ-UHFFFAOYSA-N Heptacosane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCC BJQWYEJQWHSSCJ-UHFFFAOYSA-N 0.000 description 1
- HMSWAIKSFDFLKN-UHFFFAOYSA-N Hexacosane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCC HMSWAIKSFDFLKN-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- IGGUPRCHHJZPBS-UHFFFAOYSA-N Nonacosane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCC IGGUPRCHHJZPBS-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000006358 imidation reaction Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000000752 ionisation method Methods 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- ZYURHZPYMFLWSH-UHFFFAOYSA-N n-octacosane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCC ZYURHZPYMFLWSH-UHFFFAOYSA-N 0.000 description 1
- YKNWIILGEFFOPE-UHFFFAOYSA-N n-pentacosane Natural products CCCCCCCCCCCCCCCCCCCCCCCCC YKNWIILGEFFOPE-UHFFFAOYSA-N 0.000 description 1
- FIGVVZUWCLSUEI-UHFFFAOYSA-N n-tricosane Natural products CCCCCCCCCCCCCCCCCCCCCCC FIGVVZUWCLSUEI-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- POOSGDOYLQNASK-UHFFFAOYSA-N tetracosan acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC POOSGDOYLQNASK-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
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- Indole Compounds (AREA)
- Epoxy Resins (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019092240A JP7229527B2 (ja) | 2019-05-15 | 2019-05-15 | ジイミドジカルボン酸およびそれを用いたエポキシ樹脂硬化物 |
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| JP2019092240A JP7229527B2 (ja) | 2019-05-15 | 2019-05-15 | ジイミドジカルボン酸およびそれを用いたエポキシ樹脂硬化物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020186208A JP2020186208A (ja) | 2020-11-19 |
| JP2020186208A5 JP2020186208A5 (enrdf_load_stackoverflow) | 2021-10-07 |
| JP7229527B2 true JP7229527B2 (ja) | 2023-02-28 |
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| JP2019092240A Active JP7229527B2 (ja) | 2019-05-15 | 2019-05-15 | ジイミドジカルボン酸およびそれを用いたエポキシ樹脂硬化物 |
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| JP (1) | JP7229527B2 (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021117686A1 (ja) * | 2019-12-10 | 2021-06-17 | ユニチカ株式会社 | イミド基含有化合物、イミド基含有硬化剤ならびにエポキシ樹脂硬化物およびそれを用いた電気絶縁性材料 |
| TWI809528B (zh) * | 2021-10-14 | 2023-07-21 | 財團法人工業技術研究院 | 組成物、封裝結構、與拆解封裝結構的方法 |
| KR20240087791A (ko) * | 2021-10-25 | 2024-06-19 | 유니티카 가부시끼가이샤 | 아마이드 화합물 및 그를 포함하는 경화성 수지 조성물 |
| WO2023074481A1 (ja) * | 2021-10-25 | 2023-05-04 | ユニチカ株式会社 | アミド化合物およびそれを含む硬化性樹脂組成物 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010215785A (ja) | 2009-03-17 | 2010-09-30 | Hitachi Chem Co Ltd | 耐熱性ポリアミドイミド系樹脂及びそれを用いたシームレス管状体、塗膜、塗膜板、耐熱性塗料 |
| JP2011079965A (ja) | 2009-10-07 | 2011-04-21 | Hitachi Chem Co Ltd | 耐熱性ポリアミドイミド樹脂、それを用いたシームレス管状体、塗膜、塗膜板及び耐熱性塗料 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2399412A1 (fr) * | 1977-08-05 | 1979-03-02 | France Etat | Bis-imide a base d'adamantane et procede pour sa fabrication |
| JPS58101161A (ja) * | 1981-12-14 | 1983-06-16 | Toyo Ink Mfg Co Ltd | 顔料組成物 |
| JPH086014B2 (ja) * | 1988-03-29 | 1996-01-24 | 三菱化学株式会社 | 熱可塑性ポリエステル樹脂組成物 |
| JPH0816188B2 (ja) * | 1988-03-29 | 1996-02-21 | 三菱化学株式会社 | 熱可塑性ポリエステル樹脂組成物 |
-
2019
- 2019-05-15 JP JP2019092240A patent/JP7229527B2/ja active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010215785A (ja) | 2009-03-17 | 2010-09-30 | Hitachi Chem Co Ltd | 耐熱性ポリアミドイミド系樹脂及びそれを用いたシームレス管状体、塗膜、塗膜板、耐熱性塗料 |
| JP2011079965A (ja) | 2009-10-07 | 2011-04-21 | Hitachi Chem Co Ltd | 耐熱性ポリアミドイミド樹脂、それを用いたシームレス管状体、塗膜、塗膜板及び耐熱性塗料 |
Non-Patent Citations (6)
| Title |
|---|
| Bull. Korean Chem. Soc.，2008年，29，2009-2016 |
| J. Appl. Polym. Sci.，2006年，100，3203-3211 |
| J. Polym. Sci.: Part A: Polym. Chem.，1999年，37，2873-2889 |
| Macromol. Chem. Phys.，1996年，197，701-704 |
| REGISTRY（STN）［online］，2006年，CAS 登録番号：904306-78-1他多数 |
| Sadavarte, N. V.; Patil, Sachin S.; Avadhani, C. V.; et al，New organosoluble aromatic poly(esterimide)s containing pendent pentadecyl chains: synthesis and characterization，High Performance Polymers，2013年，25(7),，735-743, 9 pp. |
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| JP2020186208A (ja) | 2020-11-19 |
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