CA2045093C - Procede de fabrication de polymeres et de copolymeres a faible densite optique servant a des photoresines et a des applications optiques - Google Patents

Procede de fabrication de polymeres et de copolymeres a faible densite optique servant a des photoresines et a des applications optiques Download PDF

Info

Publication number: CA2045093C
Authority: CA; Canada
Prior art keywords: poly; acetoxystyrene; hydroxystyrene; monomer; methyl
Prior art date: 1990-10-26
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

CA 2045093

Other languages

English (en)

Other versions

CA2045093A1 (fr

Inventor

Michael T. Sheehan

James H. Rea

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

TriQuest LP

Original Assignee

TriQuest LP

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1990-10-26

Filing date

1991-06-20

Publication date

2004-02-03

1991-05-28 Priority claimed from US07/706,601 external-priority patent/US5239015A/en

1991-06-20 Application filed by TriQuest LP filed Critical TriQuest LP

1992-04-27 Publication of CA2045093A1 publication Critical patent/CA2045093A1/fr

2004-02-03 Application granted granted Critical

2004-02-03 Publication of CA2045093C publication Critical patent/CA2045093C/fr

2011-06-20 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

229920000642 polymer Polymers 0.000 title claims abstract description 122
238000000034 method Methods 0.000 title claims abstract description 102
230000008569 process Effects 0.000 title claims abstract description 76
230000003287 optical effect Effects 0.000 title claims abstract description 19
229920001577 copolymer Polymers 0.000 title claims description 40
229920002120 photoresistant polymer Polymers 0.000 title abstract description 8
-1 poly(4-hydroxystyrene) Polymers 0.000 claims abstract description 233
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 110
238000006243 chemical reaction Methods 0.000 claims abstract description 99
239000012429 reaction media Substances 0.000 claims abstract description 88
239000000178 monomer Substances 0.000 claims abstract description 81
239000003999 initiator Substances 0.000 claims abstract description 77
JAMNSIXSLVPNLC-UHFFFAOYSA-N (4-ethenylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C=C)C=C1 JAMNSIXSLVPNLC-UHFFFAOYSA-N 0.000 claims abstract description 55
238000005809 transesterification reaction Methods 0.000 claims abstract description 55
230000005855 radiation Effects 0.000 claims abstract description 18
238000002360 preparation method Methods 0.000 claims abstract description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 93
FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 claims description 57
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
239000011541 reaction mixture Substances 0.000 claims description 34
239000000203 mixture Substances 0.000 claims description 32
239000003377 acid catalyst Substances 0.000 claims description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
150000001298 alcohols Chemical group 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 17
239000003960 organic solvent Substances 0.000 claims description 15
239000000047 product Substances 0.000 claims description 14
238000001556 precipitation Methods 0.000 claims description 12
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 11
WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical group CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 claims description 9
238000000354 decomposition reaction Methods 0.000 claims description 8
238000002955 isolation Methods 0.000 claims description 8
AQKYLAIZOGOPAW-UHFFFAOYSA-N 2-methylbutan-2-yl 2,2-dimethylpropaneperoxoate Chemical compound CCC(C)(C)OOC(=O)C(C)(C)C AQKYLAIZOGOPAW-UHFFFAOYSA-N 0.000 claims description 7
OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 claims description 7
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
239000004342 Benzoyl peroxide Substances 0.000 claims description 5
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 5
235000019400 benzoyl peroxide Nutrition 0.000 claims description 5
239000002244 precipitate Substances 0.000 claims description 5
FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 claims description 4
QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 claims description 4
ZACVGCNKGYYQHA-UHFFFAOYSA-N 2-ethylhexoxycarbonyloxy 2-ethylhexyl carbonate Chemical compound CCCCC(CC)COC(=O)OOC(=O)OCC(CC)CCCC ZACVGCNKGYYQHA-UHFFFAOYSA-N 0.000 claims description 4
MKTOIPPVFPJEQO-UHFFFAOYSA-N 4-(3-carboxypropanoylperoxy)-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)OOC(=O)CCC(O)=O MKTOIPPVFPJEQO-UHFFFAOYSA-N 0.000 claims description 4
XKXGWYAQJRXDPI-UHFFFAOYSA-N 7-methyloctanoyl 7-methyloctaneperoxoate Chemical compound CC(C)CCCCCC(=O)OOC(=O)CCCCCC(C)C XKXGWYAQJRXDPI-UHFFFAOYSA-N 0.000 claims description 4
239000004793 Polystyrene Substances 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 claims description 4
238000005227 gel permeation chromatography Methods 0.000 claims description 4
239000003112 inhibitor Substances 0.000 claims description 4
229920002223 polystyrene Polymers 0.000 claims description 4
NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 claims description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
229910017604 nitric acid Inorganic materials 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims 8
AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 claims 6
KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 claims 6
ZIDNXYVJSYJXPE-UHFFFAOYSA-N 2-methylbutan-2-yl 7,7-dimethyloctaneperoxoate Chemical compound CCC(C)(C)OOC(=O)CCCCCC(C)(C)C ZIDNXYVJSYJXPE-UHFFFAOYSA-N 0.000 claims 3
JEVXBEZNMVWKMK-UHFFFAOYSA-N CC(C)(CCC(C)(OOC(C(CCCC)CC)=O)C)OOC(C(CCCC)CC)=O.C(C)(C)(C)OOC(CCCCCC(C)(C)C)=O Chemical compound CC(C)(CCC(C)(OOC(C(CCCC)CC)=O)C)OOC(C(CCCC)CC)=O.C(C)(C)(C)OOC(CCCCCC(C)(C)C)=O JEVXBEZNMVWKMK-UHFFFAOYSA-N 0.000 claims 3
229960003328 benzoyl peroxide Drugs 0.000 claims 3
NSGQRLUGQNBHLD-UHFFFAOYSA-N butan-2-yl butan-2-yloxycarbonyloxy carbonate Chemical compound CCC(C)OC(=O)OOC(=O)OC(C)CC NSGQRLUGQNBHLD-UHFFFAOYSA-N 0.000 claims 3
QZYRMODBFHTNHF-UHFFFAOYSA-N ditert-butyl benzene-1,2-dicarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1C(=O)OOC(C)(C)C QZYRMODBFHTNHF-UHFFFAOYSA-N 0.000 claims 3
YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 claims 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
238000006467 substitution reaction Methods 0.000 claims 2
229940098779 methanesulfonic acid Drugs 0.000 claims 1
238000006116 polymerization reaction Methods 0.000 abstract description 36
238000002835 absorbance Methods 0.000 abstract description 10
230000015572 biosynthetic process Effects 0.000 abstract description 7
239000000376 reactant Substances 0.000 abstract description 6
239000003054 catalyst Substances 0.000 abstract description 5
239000012986 chain transfer agent Substances 0.000 abstract description 4
238000003384 imaging method Methods 0.000 abstract description 3
230000000379 polymerizing effect Effects 0.000 abstract description 3
239000000126 substance Substances 0.000 abstract description 2
238000001429 visible spectrum Methods 0.000 abstract 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
239000002904 solvent Substances 0.000 description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
229920001519 homopolymer Polymers 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 8
238000007792 addition Methods 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
238000010992 reflux Methods 0.000 description 8
XLLXMBCBJGATSP-UHFFFAOYSA-N 2-phenylethenol Chemical compound OC=CC1=CC=CC=C1 XLLXMBCBJGATSP-UHFFFAOYSA-N 0.000 description 7
239000007795 chemical reaction product Substances 0.000 description 7
239000008367 deionised water Substances 0.000 description 7
229910021641 deionized water Inorganic materials 0.000 description 7
JESXATFQYMPTNL-UHFFFAOYSA-N mono-hydroxyphenyl-ethylene Natural products OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 7
238000010926 purge Methods 0.000 description 7
150000003254 radicals Chemical class 0.000 description 7
230000011514 reflex Effects 0.000 description 7
FMFHUEMLVAIBFI-UHFFFAOYSA-N 2-phenylethenyl acetate Chemical compound CC(=O)OC=CC1=CC=CC=C1 FMFHUEMLVAIBFI-UHFFFAOYSA-N 0.000 description 6
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
230000006870 function Effects 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
239000000463 material Substances 0.000 description 5
QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 5
239000002245 particle Substances 0.000 description 5
229920002959 polymer blend Polymers 0.000 description 5
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000011521 glass Substances 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000012454 non-polar solvent Substances 0.000 description 4
239000002798 polar solvent Substances 0.000 description 4
239000002002 slurry Substances 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
COXCGWKSEPPDAA-UHFFFAOYSA-N 2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)C#N COXCGWKSEPPDAA-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
230000002745 absorbent Effects 0.000 description 3
239000002250 absorbent Substances 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
238000003965 capillary gas chromatography Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
229910001882 dioxygen Inorganic materials 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
150000004053 quinones Chemical class 0.000 description 3
239000000725 suspension Substances 0.000 description 3
KWTNHNLZKCUWCF-UHFFFAOYSA-N (4-ethenyl-2-methylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C=C)C=C1C KWTNHNLZKCUWCF-UHFFFAOYSA-N 0.000 description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
TZJQCUDHKUWEFU-UHFFFAOYSA-N 2,2-dimethylpentanenitrile Chemical compound CCCC(C)(C)C#N TZJQCUDHKUWEFU-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000010908 decantation Methods 0.000 description 2
ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
238000007306 functionalization reaction Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000003456 ion exchange resin Substances 0.000 description 2
229920003303 ion-exchange polymer Polymers 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
239000003505 polymerization initiator Substances 0.000 description 2
238000010557 suspension polymerization reaction Methods 0.000 description 2
229920001897 terpolymer Polymers 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
UMFCIIBZHQXRCJ-UHFFFAOYSA-N 4-prop-1-enylphenol Chemical compound CC=CC1=CC=C(O)C=C1 UMFCIIBZHQXRCJ-UHFFFAOYSA-N 0.000 description 1
YPIFGDQKSSMYHQ-UHFFFAOYSA-M 7,7-dimethyloctanoate Chemical compound CC(C)(C)CCCCCC([O-])=O YPIFGDQKSSMYHQ-UHFFFAOYSA-M 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
KUGRPPRAQNPSQD-UHFFFAOYSA-N OOOOO Chemical compound OOOOO KUGRPPRAQNPSQD-UHFFFAOYSA-N 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
230000003466 anti-cipated effect Effects 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000008901 benefit Effects 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000004907 flux Effects 0.000 description 1
239000012634 fragment Substances 0.000 description 1
239000011953 free-radical catalyst Substances 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
238000006140 methanolysis reaction Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229920003986 novolac Polymers 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
238000000206 photolithography Methods 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
230000002250 progressing effect Effects 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
235000020079 raki Nutrition 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000004065 semiconductor Substances 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000010977 unit operation Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1

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Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA 2045093 1990-10-26 1991-06-20 Procede de fabrication de polymeres et de copolymeres a faible densite optique servant a des photoresines et a des applications optiques Expired - Lifetime CA2045093C (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US60484790A	1990-10-26	1990-10-26
US07/604,847		1990-10-26
US07/706,601 US5239015A (en)	1990-06-29	1991-05-28	Process for making low optical density polymers and copolymers for photoresists and optical applications
US07/706,601		1991-05-28

Publications (2)

Publication Number	Publication Date
CA2045093A1 CA2045093A1 (fr)	1992-04-27
CA2045093C true CA2045093C (fr)	2004-02-03

Family

ID=27084782

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2045093 Expired - Lifetime CA2045093C (fr)	1990-10-26	1991-06-20	Procede de fabrication de polymeres et de copolymeres a faible densite optique servant a des photoresines et a des applications optiques

Country Status (1)

Country	Link
CA (1)	CA2045093C (fr)

1991
- 1991-06-20 CA CA 2045093 patent/CA2045093C/fr not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CA2045093A1 (fr)	1992-04-27

Legal Events

Date	Code	Title	Description
1998-03-04	EEER	Examination request
2011-06-20	MKLA	Lapsed
2012-12-02	MKEC	Expiry (correction)	Effective date: 20121202

Publication	Publication Date	Title
US5239015A (en)	1993-08-24	Process for making low optical density polymers and copolymers for photoresists and optical applications
EP0252706B1 (fr)	1992-12-23	Procédé de préparation de polyvinylphénol de polyacétoxystyrène
US4618648A (en)	1986-10-21	Copolymers of vinyl alcohol and poly(alkyleneoxy)acrylates
JP2000313721A (ja)	2000-11-14	新規ヒドロキシル基含有共重合体とその製造方法
EP0466359B1 (fr)	2000-05-10	Procédé et préparation de polymères et copolymères de basse densité optique pour photoréserves et applications optiques
JPH0655793B2 (ja)	1994-07-27	ビニルアルコールとフッ素含有アクリレート単量体との共重合体
US4708999A (en)	1987-11-24	Copolymers of vinyl acetate and poly(alkyleneoxy) acrylates
JP4343707B2 (ja)	2009-10-14	置換スチレンのホモポリマー、コポリマーおよびターポリマーの調製
CA2045093C (fr)	2004-02-03	Procede de fabrication de polymeres et de copolymeres a faible densite optique servant a des photoresines et a des applications optiques
JP4943634B2 (ja)	2012-05-30	アルコキシスチレンポリマーの精製方法
EP1076667B1 (fr)	2004-03-24	Preparation constituee de co et terpolymeres de p-hydroxystyrene et d'acrylates d'alkyle
US5376732A (en)	1994-12-27	Polymers having oxidic functionality and derivatives thereof
JPH03174416A (ja)	1991-07-29	ケトン含有光分解性ポリマーの製造法
KR20010043388A (ko)	2001-05-25	블로킹된 폴리하이드록시스티렌 수지 정제 용액의 제조방법
JPH02302406A (ja)	1990-12-14	Ｐ―アセトキシスチレンとムコン酸ジアルキルまたはソルビン酸アルキルとのコポリマーの選択的加水分解
JP2000204126A (ja)	2000-07-25	新規なマレイミド系共重合体
JPH06287205A (ja)	1994-10-11	ｐ−ｔ−ブトキシスチレン系重合体の製造方法
JPH0578403A (ja)	1993-03-30	エチレン−ビニルエステル共重合体の製造方法
GB2199836A (en)	1988-07-20	Preparation of uranyl polymers
JPS62292812A (ja)	1987-12-19	エチニル基を有する機能性共重合体およびその製造法
JPH03263406A (ja)	1991-11-22	ポリビニルアルコールの酸化方法
HK1033467B (en)	2004-09-30	Preparation of co-and terpolymers of p-hydroxystyrene and alkyl acrylates