KR20200001464A

KR20200001464A - 화학 증폭형 포지티브형 감광성 수지 조성물, 감광성 드라이 필름, 감광성 드라이 필름의 제조 방법, 패턴화된 레지스트막의 제조 방법, 주형 부착 기판의 제조 방법, 도금 조형물의 제조 방법 및 함질소 복소 고리 화합물

화학 증폭형 포지티브형 감광성 수지 조성물, 감광성 드라이 필름, 감광성 드라이 필름의 제조 방법, 패턴화된 레지스트막의 제조 방법, 주형 부착 기판의 제조 방법, 도금 조형물의 제조 방법 및 함질소 복소 고리 화합물 Download PDF

Info

Publication number: KR20200001464A
Authority: KR; South Korea
Prior art keywords: group; substituent; photosensitive resin; formula; acid
Prior art date: 2018-06-27

Application number

KR1020190056520A

Other languages

English (en)

Korean (ko)

Inventor

가즈아키 에비사와

Original Assignee

도오꾜오까고오교 가부시끼가이샤

Priority date

2018-06-27

Filing date

2019-05-14

Publication date

2020-01-06

2019-05-14 Application filed by 도오꾜오까고오교 가부시끼가이샤 filed Critical 도오꾜오까고오교 가부시끼가이샤

2020-01-06 Publication of KR20200001464A publication Critical patent/KR20200001464A/ko

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-1 nitrogen-containing heterocyclic compound Chemical class 0.000 title claims abstract description 205
239000011342 resin composition Substances 0.000 title claims abstract description 126
239000000758 substrate Substances 0.000 title claims abstract description 61
238000004519 manufacturing process Methods 0.000 title claims abstract description 43
229920005989 resin Polymers 0.000 claims abstract description 148
239000011347 resin Substances 0.000 claims abstract description 148
239000002253 acid Substances 0.000 claims abstract description 87
230000005855 radiation Effects 0.000 claims abstract description 18
239000003513 alkali Substances 0.000 claims abstract description 13
230000009471 action Effects 0.000 claims abstract description 11
125000001424 substituent group Chemical group 0.000 claims description 186
125000001931 aliphatic group Chemical group 0.000 claims description 120
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 111
150000001875 compounds Chemical class 0.000 claims description 107
125000004122 cyclic group Chemical group 0.000 claims description 88
238000000034 method Methods 0.000 claims description 64
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 62
229910052717 sulfur Inorganic materials 0.000 claims description 46
229910052751 metal Inorganic materials 0.000 claims description 44
239000002184 metal Substances 0.000 claims description 44
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 40
239000004925 Acrylic resin Substances 0.000 claims description 34
229920000178 Acrylic resin Polymers 0.000 claims description 34
238000007747 plating Methods 0.000 claims description 29
125000005647 linker group Chemical group 0.000 claims description 28
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 27
239000011593 sulfur Substances 0.000 claims description 27
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 23
238000000465 moulding Methods 0.000 claims description 20
125000004434 sulfur atom Chemical group 0.000 claims description 20
230000009467 reduction Effects 0.000 claims description 19
239000002585 base Substances 0.000 claims description 14
230000008569 process Effects 0.000 claims description 13
239000007864 aqueous solution Substances 0.000 claims description 12
238000011161 development Methods 0.000 claims description 12
125000000623 heterocyclic group Chemical group 0.000 claims description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
238000000576 coating method Methods 0.000 claims description 10
239000012528 membrane Substances 0.000 claims description 10
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
229920003986 novolac Polymers 0.000 claims description 10
239000011248 coating agent Substances 0.000 claims description 9
238000010438 heat treatment Methods 0.000 claims description 6
230000001678 irradiating effect Effects 0.000 claims description 5
238000010030 laminating Methods 0.000 claims description 5
238000003475 lamination Methods 0.000 claims description 5
230000003213 activating effect Effects 0.000 abstract 1
125000000217 alkyl group Chemical group 0.000 description 136
125000004432 carbon atom Chemical group C* 0.000 description 88
239000010408 film Substances 0.000 description 84
125000002947 alkylene group Chemical group 0.000 description 48
229940048053 acrylate Drugs 0.000 description 37
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 34
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 31
150000002430 hydrocarbons Chemical group 0.000 description 30
125000003545 alkoxy group Chemical group 0.000 description 28
229910052799 carbon Inorganic materials 0.000 description 28
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125000001153 fluoro group Chemical group F* 0.000 description 26
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239000000243 solution Substances 0.000 description 24
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ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 22
125000003118 aryl group Chemical group 0.000 description 22
125000002887 hydroxy group Chemical group [H]O* 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 21
239000000203 mixture Substances 0.000 description 21
150000001721 carbon Chemical group 0.000 description 20
125000005843 halogen group Chemical group 0.000 description 20
239000004094 surface-active agent Substances 0.000 description 20
125000005842 heteroatom Chemical group 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
229920002120 photoresistant polymer Polymers 0.000 description 17
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 16
238000005859 coupling reaction Methods 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
230000008878 coupling Effects 0.000 description 15
238000010168 coupling process Methods 0.000 description 15
150000002596 lactones Chemical class 0.000 description 15
125000003367 polycyclic group Chemical group 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 14
230000015572 biosynthetic process Effects 0.000 description 14
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 14
125000002768 hydroxyalkyl group Chemical group 0.000 description 14
229920001296 polysiloxane Polymers 0.000 description 14
125000003396 thiol group Chemical group [H]S* 0.000 description 14
239000010949 copper Substances 0.000 description 13
125000001624 naphthyl group Chemical group 0.000 description 13
238000002360 preparation method Methods 0.000 description 12
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
125000004429 atom Chemical group 0.000 description 11
238000009792 diffusion process Methods 0.000 description 11
230000002349 favourable effect Effects 0.000 description 11
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 11
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 11
239000003960 organic solvent Substances 0.000 description 11
229910052760 oxygen Inorganic materials 0.000 description 11
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
125000006165 cyclic alkyl group Chemical group 0.000 description 10
230000018109 developmental process Effects 0.000 description 10
238000011156 evaluation Methods 0.000 description 10
125000002950 monocyclic group Chemical group 0.000 description 10
239000000126 substance Substances 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
230000000052 comparative effect Effects 0.000 description 9
125000004093 cyano group Chemical group *C#N 0.000 description 9
229910052740 iodine Inorganic materials 0.000 description 9
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
239000001301 oxygen Substances 0.000 description 9
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
229910052801 chlorine Inorganic materials 0.000 description 8
230000002401 inhibitory effect Effects 0.000 description 8
UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
238000003860 storage Methods 0.000 description 8
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
238000007112 amidation reaction Methods 0.000 description 7
150000001450 anions Chemical class 0.000 description 7
238000004380 ashing Methods 0.000 description 7
150000001768 cations Chemical group 0.000 description 7
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
238000004090 dissolution Methods 0.000 description 7
229910052698 phosphorus Inorganic materials 0.000 description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
150000001491 aromatic compounds Chemical class 0.000 description 6
150000004945 aromatic hydrocarbons Chemical group 0.000 description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
238000006664 bond formation reaction Methods 0.000 description 6
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
238000005886 esterification reaction Methods 0.000 description 6
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
125000005358 mercaptoalkyl group Chemical group 0.000 description 6
150000002763 monocarboxylic acids Chemical class 0.000 description 6
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
239000011574 phosphorus Substances 0.000 description 6
229920000139 polyethylene terephthalate Polymers 0.000 description 6
239000005020 polyethylene terephthalate Substances 0.000 description 6
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YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
238000005160 1H NMR spectroscopy Methods 0.000 description 5
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 5
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
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150000008064 anhydrides Chemical class 0.000 description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
230000008859 change Effects 0.000 description 5
229910052802 copper Inorganic materials 0.000 description 5
150000001991 dicarboxylic acids Chemical class 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
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239000007788 liquid Substances 0.000 description 5
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238000005259 measurement Methods 0.000 description 5
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 5
238000002156 mixing Methods 0.000 description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 5
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
238000006467 substitution reaction Methods 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
238000005406 washing Methods 0.000 description 5
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125000006833 (C1-C5) alkylene group Chemical group 0.000 description 4
JHVQWALHXJPODC-ALCCZGGFSA-N (z)-2-[2-(2-methylprop-2-enoyloxy)ethyl]but-2-enedioic acid Chemical compound CC(=C)C(=O)OCC\C(C(O)=O)=C\C(O)=O JHVQWALHXJPODC-ALCCZGGFSA-N 0.000 description 4
NWHNXXMYEICZAT-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidin-4-ol Chemical class CN1C(C)(C)CC(O)CC1(C)C NWHNXXMYEICZAT-UHFFFAOYSA-N 0.000 description 4
YUTHQCGFZNYPIG-UHFFFAOYSA-N 1-[2-(2-methylprop-2-enoyloxy)ethyl]cyclohexane-1,2-dicarboxylic acid Chemical compound CC(=C)C(=O)OCCC1(C(O)=O)CCCCC1C(O)=O YUTHQCGFZNYPIG-UHFFFAOYSA-N 0.000 description 4
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125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
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KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
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IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
239000004698 Polyethylene Substances 0.000 description 4
239000004743 Polypropylene Substances 0.000 description 4
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
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239000000654 additive Substances 0.000 description 4
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238000005266 casting Methods 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
229920001577 copolymer Polymers 0.000 description 4
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230000000694 effects Effects 0.000 description 4
230000032050 esterification Effects 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
238000005755 formation reaction Methods 0.000 description 4
239000001530 fumaric acid Substances 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical class 0.000 description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 4
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