JP6432814B2 - アルコール変性ポリアミドイミド樹脂およびその製造方法 - Google Patents
アルコール変性ポリアミドイミド樹脂およびその製造方法 Download PDFInfo
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- JP6432814B2 JP6432814B2 JP2018521670A JP2018521670A JP6432814B2 JP 6432814 B2 JP6432814 B2 JP 6432814B2 JP 2018521670 A JP2018521670 A JP 2018521670A JP 2018521670 A JP2018521670 A JP 2018521670A JP 6432814 B2 JP6432814 B2 JP 6432814B2
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- alcohol
- polyamideimide resin
- acid anhydride
- resin
- producing
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- 239000011347 resin Substances 0.000 title claims description 192
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- 238000006243 chemical reaction Methods 0.000 claims description 69
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 65
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- 239000011342 resin composition Substances 0.000 claims description 58
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 31
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- 150000002513 isocyanates Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 23
- 125000001931 aliphatic group Chemical group 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 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 6
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- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 6
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- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 5
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- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 235000019837 monoammonium phosphate Nutrition 0.000 description 1
- 239000006012 monoammonium phosphate Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 1
- WRYWBRATLBWSSG-UHFFFAOYSA-N naphthalene-1,2,4-tricarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC(C(O)=O)=C21 WRYWBRATLBWSSG-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 239000011255 nonaqueous electrolyte Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical group 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 238000002161 passivation Methods 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical class [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- FSDNTQSJGHSJBG-UHFFFAOYSA-N piperidine-4-carbonitrile Chemical compound N#CC1CCNCC1 FSDNTQSJGHSJBG-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920005575 poly(amic acid) Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005650 polypropylene glycol diacrylate Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 239000012783 reinforcing fiber Substances 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 229910021647 smectite Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229960004025 sodium salicylate Drugs 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- FOZHTJJTSSSURD-UHFFFAOYSA-J titanium(4+);dicarbonate Chemical compound [Ti+4].[O-]C([O-])=O.[O-]C([O-])=O FOZHTJJTSSSURD-UHFFFAOYSA-J 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 description 1
- PZRXQXJGIQEYOG-UHFFFAOYSA-N zinc;oxido(oxo)borane Chemical compound [Zn+2].[O-]B=O.[O-]B=O PZRXQXJGIQEYOG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/14—Polyamide-imides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
工程(1)で得られたポリアミドイミド樹脂(A1)に、さらにアルコール化合物(a3)を加えて反応させることによりアルコール変性ポリアミドイミド樹脂(A2)を生成する工程(2)、を有するアルコール変性ポリアミドイミド樹脂の製造方法であって、
前記工程(1)は、トリカルボン酸無水物(a1)に対して、前記イソシアヌレート型ポリイソシアネート(a2)を少なくとも2回に分けて加えることにより、前記イソシアヌレート型ポリイソシアネート(a2)とトリカルボン酸無水物(a1)とを反応させた後、得られた反応物に、さらに、前記イソシアヌレート型ポリイソシアネート(a2)を反応させる工程(1a)を含むことを特徴とするアルコール変性ポリアミドイミド樹脂の製造方法に関する。
工程(1)で得られたポリアミドイミド樹脂(A1)に、さらにアルコール化合物(a3)を反応させることによりアルコール変性ポリアミドイミド樹脂(A2)を生成する工程(2)を有し、
前記工程(1)は、トリカルボン酸無水物(a1)に対して、前記イソシアヌレート型ポリイソシアネート(a2)を少なくとも2回に分けて加えることにより、トリカルボン酸無水物(a1)と、前記イソシアヌレート型ポリイソシアネート(a2)とを反応させた後、得られた生成物に、さらに前記イソシアヌレート型ポリイソシアネート(a2)を反応させる工程(1a)を含むことを特徴とする。
(1)ポリアミドイミド樹脂(A1)を、溶剤等で希釈し、KOH水溶液の滴定により酸価(a)を求める。
(2)ポリアミドイミド樹脂(A1)を溶剤等で希釈し、酸無水物基に過剰量のn−ブタノールを反応させた後、KOH水溶液の滴定により酸価(b)を求める。なお、(2)において、酸無水物基とn−ブタノールの反応は、117℃にて行うものとする。酸無水物の消失は赤外スペクトルにて、酸無水物基の特性吸収である1860cm-1が完全に消滅したことで確認する。
(3)上記酸価(a)と酸価(b)の差より、本発明のポリアミドイミド樹脂(A1)中の酸無水物基の濃度を算出し、モル数(M3)に換算する。
測定装置:東ソー株式会社製 HLC−8120GPC、UV8020
カラム :東ソー株式会社製 TFKguardcolumnhxl−L、TFKgel(G1000HXL、G2000HXL、G3000HXL、G4000HXL)
検出器 :RI(示差屈折計)及びUV(254nm)
測定条件:カラム温度 40℃
溶媒 THF
流束 1.0ml/min
標準 :ポリスチレン標準試料にて検量線作成
試料 :樹脂固形分換算で0.1質量%のTHF溶液をマイクロフィルターでろ過したもの(注入量:200μl)
もちろん、活性エネルギー線と熱とを併用して硬化させることについてもその使用にあたっては、何ら限定がない。
本発明の白色プリプレグは、本発明の硬化性樹脂組成物と白色顔料を含む混合物を、シート状ガラス繊維基材に含浸または塗布させた後、乾燥させてなることを特徴とする。具体的には、本発明の硬化性樹脂組成物と白色顔料を含む混合物を、シート状ガラス繊維基材に含浸または塗布させた後、100〜200℃の範囲の乾燥機中で1〜60分間の範囲にて半硬化させることを特徴とする。以下に白色プリプレグ、その製造方法を具体的に説明する。
〔ポリアミドイミド樹脂(A1−1)の調製〕
撹拌装置、温度計、コンデンサーを付けたフラスコにPGMAc(プロピレングリコールモノメチルエーテルアセテート)1102.8g、IPDI3N(イソホロンジイソシアネートから合成されたイソシアヌレート型トリイソシアネート:NCO%=17.2)197.6g(0.27mol)及びシクロヘキサン−1,3,4−トリカルボン酸-3,4−無水物506.9g(2.56mol)を加え、140℃まで2時間掛けて昇温した。反応は、発泡とともに進行した。この温度で2時間反応させた。系内は淡黄色の液体となり、赤外スペクトルにて特性吸収を測定した結果、イソシアネート基の特性吸収である2270cm−1が完全に消滅したことが確認された。更に、IPDI3Nを197.6g(0.27mol)加え、反応を継続させた。赤外スペクトルにて特性吸収を測定し、イソシアネート基の特性吸収である2270cm−1が完全に消滅したことを確認した後、更にIPDI3Nを197.6g(0.27mol)加え、反応を継続させた。赤外スペクトルにて特性吸収を測定し、イソシアネート基の特性吸収である2270cm−1が完全に消滅し、1780cm−1、1720cm−1にイミド基の吸収が確認された。酸価は、固形分換算で190KOHmg/gであった。この樹脂の溶液をイミド樹脂(A1−1)の溶液と略記する。
続いて、得られたイミド樹脂(A1−1)の溶液にn−ブタノール99.8g(1.35mol)を加え、120℃にて2時間反応させた。赤外スペクトルにて特性吸収を測定した結果、酸無水物基の特性吸収である1860cm−1の吸収が完全に消失した。酸価は、固形分換算で、162KOHmg/gで、分子量はポリスチレン換算で数平均分子量1180、質量平均分子量2054、分散度は1.74であった。この樹脂の溶液をアルコール変性ポリアミドイミド樹脂(A1−2)と略記する。
〔ポリアミドイミド樹脂(A2−1)の調製〕
撹拌装置、温度計、コンデンサーを付けたフラスコにPGMAc(プロピレングリコールモノメチルエーテルアセテート)331.9g、IPDI3N(イソホロンジイソシアネートから合成されたイソシアヌレート型トリイソシアネート:NCO%=17.2)35.1g(0.05mol)及びシクロヘキサン−1,3,4−トリカルボン酸-3,4−無水物150.3g(0.76mol)を加え、140℃まで2時間掛けて昇温した。反応は、発泡とともに進行した。この温度で2時間反応させた。系内は淡黄色の液体となり、赤外スペクトルにて特性吸収を測定した結果、イソシアネート基の特性吸収である2270cm−1が完全に消滅したことが確認された。更に、IPDI3Nを35.1g(0.05mol)加え、反応を継続させた。赤外スペクトルにて特性吸収を測定し、イソシアネート基の特性吸収である2270cm−1が完全に消滅したことを確認した後、更にIPDI3Nを35.1g(0.05mol)加え、反応を継続させた。赤外スペクトルにて特性吸収を測定し、イソシアネート基の特性吸収である2270cm−1が完全に消滅したことを確認した後、更にIPDI3Nを35.1g(0.05mol)加え、反応を継続させた。赤外スペクトルにて特性吸収を測定し、イソシアネート基の特性吸収である2270cm−1が完全に消滅したことを確認した後、更にIPDI3Nを35.1g(0.05mol)加え、反応を継続させた。赤外スペクトルで特性吸収を測定し、イソシアネート基の特性吸収である2270cm−1が完全に消滅し、1780cm−1、1720cm−1にイミド基の吸収が確認された。酸価は、固形分換算で196KOHmg/gであった。この樹脂の溶液をイミド樹脂(A2−1)の溶液と略記する。
続いて、得られたイミド樹脂(A2−1)の溶液にn−ブタノール29.4g(0.40mol)を加え、120℃にて2時間反応させた。赤外スペクトルにて特性吸収を測定した結果、酸無水物基の特性吸収である1860cm−1の吸収が完全に消失した。酸価は、固形分換算で、161KOHmg/gで、分子量はポリスチレン換算で数平均分子量990、質量平均分子量1822、分散度は1.84であった。この樹脂の溶液をアルコール変性ポリアミドイミド樹脂(A1−2)と略記する。
〔ポリアミドイミド樹脂(A3−1)の調製〕
撹拌装置、温度計、コンデンサーを付けたフラスコにPGMAc(プロピレングリコールモノメチルエーテルアセテート)331.9g、IPDI3N(イソホロンジイソシアネートから合成されたイソシアヌレート型トリイソシアネート:NCO%=17.2)87.8g(0.12mol)及びシクロヘキサン−1,3,4−トリカルボン酸-3,4−無水物150.3g(0.76mol)を加え、140℃まで2時間掛けて昇温した。反応は、発泡とともに進行した。この温度で2時間反応させた。系内は淡黄色の液体となり、赤外スペクトルにて特性吸収を測定した結果、イソシアネート基の特性吸収である2270cm−1が完全に消滅したことが確認された。更に、IPDI3Nを58.6g(0.08mol)加え、反応を継続させた。赤外スペクトルにて特性吸収を測定し、イソシアネート基の特性吸収である2270cm−1が完全に消滅したことを確認した後、更にIPDI3Nを29.3g(0.04mol)加え、反応を継続させた。赤外スペクトルにて特性吸収を測定し、イソシアネート基の特性吸収である2270cm−1が完全に消滅し、1780cm−1、1720cm−1にイミド基の吸収が確認された。酸価は、固形分換算で185KOHmg/gであった。この樹脂の溶液をイミド樹脂(A3−1)の溶液と略記する。
続いて、得られたイミド樹脂(A3−1)の溶液にn−ブタノール29.4g(0.40mol)を加え、120℃にて2時間反応させた。赤外スペクトルにて特性吸収を測定した結果、酸無水物基の特性吸収である1860cm−1の吸収が完全に消失した。酸価は、固形分換算で、157KOHmg/gで、分子量はポリスチレン換算で数平均分子量1007、質量平均分子量1762、分散度は1.75であった。この樹脂の溶液をアルコール変性ポリアミドイミド樹脂(A3−2)と略記する。
〔ポリアミドイミド樹脂(A4−1)の調製〕
撹拌装置、温度計、コンデンサーを付けたフラスコにPGMAc(プロピレングリコールモノメチルエーテルアセテート)331.9g、IPDI3N(イソホロンジイソシアネートから合成されたイソシアヌレート型トリイソシアネート:NCO%=17.2)29.3g(0.04mol)及びシクロヘキサン−1,3,4−トリカルボン酸-3,4−無水物150.3g(0.76mol)を加え、140℃まで2時間掛けて昇温した。反応は、発泡とともに進行した。この温度で2時間反応させた。系内は淡黄色の液体となり、赤外スペクトルにて特性吸収を測定した結果、イソシアネート基の特性吸収である2270cm−1が完全に消滅したことが確認された。更に、IPDI3Nを58.6g(0.08mol)加え、反応を継続させた。赤外スペクトルにて特性吸収を測定し、イソシアネート基の特性吸収である2270cm−1が完全に消滅したことを確認した後、更にIPDI3Nを87.8g(0.12mol)加え、反応を継続させた。赤外スペクトルにて特性吸収を測定し、イソシアネート基の特性吸収である2270cm−1が完全に消滅し、1780cm−1、1720cm−1にイミド基の吸収が確認された。酸価は、固形分換算で190KOHmg/gであった。この樹脂の溶液をイミド樹脂(A4−1)の溶液と略記する。
続いて、得られたイミド樹脂(A4−1)の溶液にn−ブタノール29.4g(0.40mol)を加え、120℃にて2時間反応させた。赤外スペクトルにて特性吸収を測定した結果、酸無水物基の特性吸収である1860cm−1の吸収が完全に消失した。酸価は、固形分換算で、161KOHmg/gで、分子量はポリスチレン換算で数平均分子量1022、質量平均分子量1931、分散度は1.89であった。この樹脂の溶液をアルコール変性ポリアミドイミド樹脂(A4−2)と略記する。
撹拌装置、温度計、コンデンサーを付けたフラスコにPGMAc(プロピレングリコールモノメチルエーテルアセテート)276.4g、IPDI3N(イソホロンジイソシアネートから合成されたイソシアヌレート型トリイソシアネート:NCO%=17.2)146.4g(0.20mol)及びシクロヘキサン−1,3,4−トリカルボン酸-3,4−無水物125.1g(0.63mol)を加え、140℃まで2時間掛けて昇温した。反応は、発泡とともに進行した。この温度で4時間反応させた。系内は淡黄色の液体となり、赤外スペクトルにて特性吸収を測定した結果、イソシアネート基の特性吸収である2270cm−1が完全に消滅し、1780cm−1、1720cm−1にイミド基の吸収が確認された。酸価は、固形分換算で212KOHmg/gであった。この樹脂の溶液をイミド樹脂(A5−1)の溶液と略記する。
続いて、得られたイミド樹脂(A5−1)の溶液にn−ブタノール24.5g(0.33mol)を加え、120℃にて2時間反応させた。赤外スペクトルにて特性吸収を測定した結果、酸無水物基の特性吸収である1860cm-1の吸収が完全に消失した。酸価は、固形分換算で、162KOHmg/gで、分子量はポリスチレン換算で数平均分子量1289、質量平均分子量3152、分散度は2.45であった。この樹脂の溶液をアルコール変性ポリアミドイミド樹脂(A5−2)と略記する。
撹拌装置、温度計、コンデンサーを付けたフラスコにPGMAc(プロピレングリコールモノメチルエーテルアセテート)276.4g、IPDI3N(イソホロンジイソシアネートから合成されたイソシアヌレート型トリイソシアネート:NCO%=17.2)146.4g(0.20mol)及びシクロヘキサン−1,3,4−トリカルボン酸−3,4−無水物125.1g(0.63mol)を加え、140℃まで4時間掛けて昇温した。反応は、発泡とともに進行した。この温度で4時間反応させた。系内は淡黄色の液体となり、赤外スペクトルにて特性吸収を測定した結果、イソシアネート基の特性吸収である2270cm−1が完全に消滅し、1780cm−1 、1720cm−1にイミド基の吸収が確認された。酸価は、固形分換算で184KOHmg/gであった。この樹脂の溶液をイミド樹脂(A6−1)の溶液と略記する。
続いて、得られたイミド樹脂(A6−1)の溶液にn−ブタノール24.5g(0.33mol)を加え、120℃にて2時間反応させた。赤外スペクトルにて特性吸収を測定した結果、酸無水物基の特性吸収である1860cm-1の吸収が完全に消失した。酸価は、固形分換算で、163KOHmg/gで、分子量はポリスチレン換算で数平均分子量1216、質量平均分子量2528、分散度は2.08であった。この樹脂の溶液をアルコール変性ポリアミドイミド樹脂(A6−2)と略記する。
上記で得られたアルコール変性ポリアミドイミド樹脂を用いて、表1に記載した配合条件で、硬化性樹脂組成物1〜6を製造した。
EHPE3150:ダイセル化学工業株式会社製の環式脂肪族系エポキシ樹脂(2,2−ビス(ヒドロキシメチル)−1−ブタノールの1,2−エポキシ−4−(2−オキシラニル)シクロヘキサン付加物)。エポキシ当量は177。樹脂分の濃度は100質量%。
160℃に加熱したホットプレート上で加熱し、当該硬化性樹脂組成物1〜6の糸引きがなくなるまでの時間をそれぞれ測定した。得られた結果を表2に「160℃ゲルタイム」として示した。
樹脂をガラス基板上に乾燥後に膜厚17μmになるように塗装を行った。塗装板を90℃の乾燥機で15分乾燥させて、塗膜を得た。次いで、塗装板を25℃の1%Na2CO3水溶液に浸漬し、塗膜が消失するまでの時間を測定した。表3に示した。
フラスコに樹脂を10g加えた後、25℃のPGMAcを加えていき、濁りが確認されたところを希釈限界とした。表3に示した。
ポリスチレン換算の数平均分子量と質量平均分子量の比から算出した。表3に示した。
Claims (13)
- トリカルボン酸無水物(a1)と、脂肪族構造を有するイソシアネートから合成されたイソシアヌレート型ポリイソシアネート(a2)とを反応させることによりポリアミドイミド樹脂(A1)を生成する工程(1)、
工程(1)で得られたポリアミドイミド樹脂(A1)に、さらにアルコール化合物(a3)を反応させることによりアルコール変性ポリアミドイミド樹脂(A2)を生成する工程(2)、を有するアルコール変性ポリアミドイミド樹脂の製造方法であって、
前記工程(1)は、トリカルボン酸無水物(a1)に対して、前記イソシアヌレート型ポリイソシアネート(a2)を少なくとも2回に分けて加えることにより、前記イソシアヌレート型ポリイソシアネート(a2)とトリカルボン酸無水物(a1)とを反応させた後、得られた反応物に、さらに前記イソシアヌレート型ポリイソシアネート(a2)を反応させる工程(1a)を含むことを特徴とするアルコール変性ポリアミドイミド樹脂の製造方法。 - 前記工程(1a)は、前記イソシアヌレート型ポリイソシアネート(a2)のイソシアネート基のモル数に対して、トリカルボン酸無水物(a1)のカルボキシ基のモル数及び酸無水物基モル数の合計が過剰量となる割合で、トリカルボン酸無水物(a1)と、前記イソシアヌレート型ポリイソシアネート(a2)とを反応させた後、得られた反応物に、さらに前記イソシアヌレート型ポリイソシアネート(a2)を反応させる工程である、請求項1記載のアルコール変性ポリアミドイミド樹脂の製造方法。
- 前記工程(1a)は、トリカルボン酸無水物(a1)と前記イソシアヌレート型ポリイソシアネート(a2)とを反応させ、赤外吸収スペクトル測定においてイソシアネート基の特性吸収である2270cm−1が消滅するまで反応を進行させた後に、得られた反応物に、さらに前記イソシアヌレート型ポリイソシアネート(a2)を反応させる工程である請求項1又は2記載のアルコール変性ポリアミドイミド樹脂の製造方法。
- 前記イソシアヌレート型ポリイソシアネート(a2)のイソシアネート基の合計のモル数(N)に対する、トリカルボン酸無水物(a1)のカルボキシ基のモル数(M1)及び酸無水物基モル数(M2)の合計のモル数の比〔(M1)+(M2))/(N)〕が1.1〜3である請求項1〜3の何れか一項記載のアルコール変性ポリアミドイミド樹脂の製造方法。
- 前記工程(2)において、赤外吸収スペクトル測定においてイソシアネート基の特性吸収である2270cm−1が消滅したポリアミドイミド樹脂(A1)に対して、アルコール化合物(a3)を反応させる、請求項1〜4の何れか一項記載のアルコール変性ポリアミドイミド樹脂の製造方法。
- 前記工程(2)において、前記ポリアミドイミド樹脂(A1)とアルコール化合物(a3)との反応は、該ポリアミドイミド樹脂(A1)中の酸無水物基モル数(M3)と、アルコール化合物(a3)の水酸基のモル数(L)との比が、M3/L=1〜5の範囲である請求項1〜5の何れか一項記載のアルコール変性ポリアミドイミド樹脂の製造方法。
- 分子量分布が2.0以下の範囲である請求項1〜6の何れか一項記載のアルコール変性ポリアミドイミド樹脂の製造方法。
- 数平均分子量が800〜20000の範囲であり、質量平均分子量が1600〜40000の範囲である請求項1〜7の何れか一項記載のアルコール変性ポリアミドイミド樹脂の製造方法。
- 酸価が70〜210KOHmg/gである請求項1〜8の何れか一項記載のアルコール変性ポリアミドイミド樹脂の製造方法。
- 前記脂肪族構造を有するイソシアネートが、環式脂肪族構造を有するイソシアネートである請求項1〜9の何れか一項記載のアルコール変性ポリアミドイミド樹脂の製造方法。
- 請求項1〜10のいずれか1項記載のアルコール変性ポリアミドイミド樹脂と、硬化性樹脂(B)及び/又は有機溶剤(C)とを含有することを特徴とする硬化性樹脂組成物の製造方法。
- さらに、光重合開始剤(D)を含有する請求項11項記載の硬化性樹脂組成物の製造方法。
- 請求項11または12記載の硬化性樹脂組成物を硬化させてなることを特徴とする硬化物の製造方法。
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KR20190020295A (ko) | 2019-02-28 |
TWI745383B (zh) | 2021-11-11 |
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