JP2005330446A - ビニル重合体、リビングラジカル重合体およびそれらの製造方法 - Google Patents
ビニル重合体、リビングラジカル重合体およびそれらの製造方法 Download PDFInfo
- Publication number
- JP2005330446A JP2005330446A JP2004152519A JP2004152519A JP2005330446A JP 2005330446 A JP2005330446 A JP 2005330446A JP 2004152519 A JP2004152519 A JP 2004152519A JP 2004152519 A JP2004152519 A JP 2004152519A JP 2005330446 A JP2005330446 A JP 2005330446A
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- Prior art keywords
- polymerization
- borane
- polymer
- vinyl
- polymerization initiator
- Prior art date
- 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.)
- Pending
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- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 170
- 229920000642 polymer Polymers 0.000 title claims abstract description 168
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 82
- 239000012298 atmosphere Substances 0.000 claims abstract description 245
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 177
- 239000002904 solvent Substances 0.000 claims abstract description 136
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 119
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract description 63
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims abstract description 26
- GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical group CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 416
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 217
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 146
- 239000000178 monomer Substances 0.000 claims description 128
- 229910000085 borane Inorganic materials 0.000 claims description 109
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 100
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 claims description 83
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 69
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 66
- KHYAFFAGZNCWPT-UHFFFAOYSA-N boron;n,n-diethylaniline Chemical compound [B].CCN(CC)C1=CC=CC=C1 KHYAFFAGZNCWPT-UHFFFAOYSA-N 0.000 claims description 58
- FESAXEDIWWXCNG-UHFFFAOYSA-N diethyl(methoxy)borane Chemical compound CCB(CC)OC FESAXEDIWWXCNG-UHFFFAOYSA-N 0.000 claims description 56
- NNTOJPXOCKCMKR-UHFFFAOYSA-N boron;pyridine Chemical compound [B].C1=CC=NC=C1 NNTOJPXOCKCMKR-UHFFFAOYSA-N 0.000 claims description 42
- 230000000379 polymerizing effect Effects 0.000 claims description 28
- VCDGSBJCRYTLNU-CJGYBVCLSA-N 9-[(1r,3r,4s,5r)-4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]-9-borabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1B2[C@@H]1C[C@@H](C2(C)C)C[C@@H]2[C@H]1C VCDGSBJCRYTLNU-CJGYBVCLSA-N 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000010526 radical polymerization reaction Methods 0.000 abstract description 70
- 239000003999 initiator Substances 0.000 description 161
- 238000006243 chemical reaction Methods 0.000 description 130
- 150000003254 radicals Chemical class 0.000 description 107
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 77
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 75
- 238000012662 bulk polymerization Methods 0.000 description 74
- 239000012300 argon atmosphere Substances 0.000 description 51
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 47
- 239000001301 oxygen Substances 0.000 description 47
- 229910052760 oxygen Inorganic materials 0.000 description 47
- 150000001412 amines Chemical class 0.000 description 42
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 40
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 38
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 37
- 230000006399 behavior Effects 0.000 description 37
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 36
- 230000007246 mechanism Effects 0.000 description 36
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 34
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 30
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 29
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 29
- 150000002978 peroxides Chemical class 0.000 description 26
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 25
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 24
- 238000010828 elution Methods 0.000 description 24
- 238000005227 gel permeation chromatography Methods 0.000 description 24
- 238000010550 living polymerization reaction Methods 0.000 description 24
- 230000008859 change Effects 0.000 description 21
- 239000003112 inhibitor Substances 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- -1 metal hydroxide salt Chemical class 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 16
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 15
- 230000000977 initiatory effect Effects 0.000 description 15
- 241000894007 species Species 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- 230000000694 effects Effects 0.000 description 13
- 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 description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- 229910052796 boron Inorganic materials 0.000 description 12
- 238000006197 hydroboration reaction Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 239000000654 additive Substances 0.000 description 11
- 230000000996 additive effect Effects 0.000 description 11
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 10
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 10
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 9
- 239000004342 Benzoyl peroxide Substances 0.000 description 9
- 239000002841 Lewis acid Substances 0.000 description 9
- 239000002879 Lewis base Substances 0.000 description 9
- 235000019400 benzoyl peroxide Nutrition 0.000 description 9
- 150000007517 lewis acids Chemical class 0.000 description 9
- 150000007527 lewis bases Chemical class 0.000 description 9
- 238000012546 transfer Methods 0.000 description 9
- FPEQNDQUWPJCKZ-UHFFFAOYSA-N 9-borabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1B2.C1CCC2CCCC1B2 FPEQNDQUWPJCKZ-UHFFFAOYSA-N 0.000 description 8
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo[3.3.1]nonane Substances C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 description 7
- 0 C(C1)C2CC*C1*2 Chemical compound C(C1)C2CC*C1*2 0.000 description 7
- 239000012986 chain transfer agent Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000007870 radical polymerization initiator Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 6
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 6
- 229920006167 biodegradable resin Polymers 0.000 description 6
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 229920001519 homopolymer Polymers 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000012719 thermal polymerization Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 4
- 238000006897 homolysis reaction Methods 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 4
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 3
- 230000002860 competitive effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- NAMDIHYPBYVYAP-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethoxy)ethane Chemical compound COCCOCCOC.COCCOCCOC NAMDIHYPBYVYAP-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical class N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- CCAUAJMPYUTFEJ-VEDVMXKPSA-N CC1(B(C2)OO)C=C[C@H]2CCC1 Chemical compound CC1(B(C2)OO)C=C[C@H]2CCC1 CCAUAJMPYUTFEJ-VEDVMXKPSA-N 0.000 description 1
- ZNKKYYNWFKHNHZ-UHFFFAOYSA-N CC1C=CC=CC1 Chemical compound CC1C=CC=CC1 ZNKKYYNWFKHNHZ-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- OXSZTFYNKKCFFQ-ULUSZKPHSA-N OB1C2CCC[C@@H]1CC2 Chemical compound OB1C2CCC[C@@H]1CC2 OXSZTFYNKKCFFQ-ULUSZKPHSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- ITOJEBDYSWRTML-UHFFFAOYSA-N carbon tetroxide Chemical compound O=C1OOO1 ITOJEBDYSWRTML-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 150000002012 dioxanes Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 239000012372 hydroboration reagent Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000012690 ionic polymerization Methods 0.000 description 1
- 238000010982 kinetic investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- IWVKTOUOPHGZRX-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.COC(=O)C(C)=C IWVKTOUOPHGZRX-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920000052 poly(p-xylylene) Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 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
- YUPAWYWJNZDARM-UHFFFAOYSA-N tri(butan-2-yl)borane Chemical compound CCC(C)B(C(C)CC)C(C)CC YUPAWYWJNZDARM-UHFFFAOYSA-N 0.000 description 1
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
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- Polymerization Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004152519A JP2005330446A (ja) | 2004-05-21 | 2004-05-21 | ビニル重合体、リビングラジカル重合体およびそれらの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004152519A JP2005330446A (ja) | 2004-05-21 | 2004-05-21 | ビニル重合体、リビングラジカル重合体およびそれらの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005330446A true JP2005330446A (ja) | 2005-12-02 |
| JP2005330446A5 JP2005330446A5 (enExample) | 2007-07-05 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004152519A Pending JP2005330446A (ja) | 2004-05-21 | 2004-05-21 | ビニル重合体、リビングラジカル重合体およびそれらの製造方法 |
Country Status (1)
| Country | Link |
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| JP (1) | JP2005330446A (enExample) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1947122A1 (en) * | 2007-01-22 | 2008-07-23 | Total Petrochemicals France | Process for preparing high impact monovinylaromatic polymers in the presence of a borane complex |
| JP2013166835A (ja) * | 2012-02-15 | 2013-08-29 | Hitachi Ltd | 熱硬化性樹脂組成物、硬化物、導線、電気機器用コイル及び電気機器 |
| WO2014038031A1 (ja) * | 2012-09-06 | 2014-03-13 | 株式会社日立製作所 | ホウ素化合物を用いた重合体の形成方法並びに重合開始剤及び重合体 |
| JP2014136706A (ja) * | 2013-01-15 | 2014-07-28 | Hitachi Chemical Co Ltd | 樹脂組成物、樹脂組成物の製造方法、樹脂組成物を含むレジスト組成物及びレジスト組成物を用いたパターン形成方法 |
| WO2019022227A1 (ja) | 2017-07-28 | 2019-01-31 | デンカ株式会社 | 重合体の製造方法 |
| JP2020012024A (ja) * | 2018-07-13 | 2020-01-23 | 信越化学工業株式会社 | 酸素硬化性シリコーン組成物およびその硬化物 |
| JP2020012025A (ja) * | 2018-07-13 | 2020-01-23 | 信越化学工業株式会社 | 酸素硬化性シリコーン組成物およびその硬化物 |
-
2004
- 2004-05-21 JP JP2004152519A patent/JP2005330446A/ja active Pending
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1947122A1 (en) * | 2007-01-22 | 2008-07-23 | Total Petrochemicals France | Process for preparing high impact monovinylaromatic polymers in the presence of a borane complex |
| WO2008090119A1 (en) * | 2007-01-22 | 2008-07-31 | Total Petrochemicals France | Process for preparing high impact monovinylaromatic polymers in the presence of a borane complex |
| US8399561B2 (en) | 2007-01-22 | 2013-03-19 | Total Petrochemicals France | Process for preparing high impact monovinylaromatic polymers in the presence of a borane complex |
| JP2013166835A (ja) * | 2012-02-15 | 2013-08-29 | Hitachi Ltd | 熱硬化性樹脂組成物、硬化物、導線、電気機器用コイル及び電気機器 |
| WO2014038031A1 (ja) * | 2012-09-06 | 2014-03-13 | 株式会社日立製作所 | ホウ素化合物を用いた重合体の形成方法並びに重合開始剤及び重合体 |
| JP5851045B2 (ja) * | 2012-09-06 | 2016-02-03 | 株式会社日立製作所 | ホウ素化合物を用いた重合体の形成方法並びに重合開始剤及び重合体並びにケーブル被覆材、ケーブル、モールド封止材、モールド封止方法、電子部品パッケージ及び構造材料 |
| US9771436B2 (en) | 2012-09-06 | 2017-09-26 | Hitachi, Ltd. | Method for forming polymer using boron compound, polymerization initiator and the polymer |
| JP2014136706A (ja) * | 2013-01-15 | 2014-07-28 | Hitachi Chemical Co Ltd | 樹脂組成物、樹脂組成物の製造方法、樹脂組成物を含むレジスト組成物及びレジスト組成物を用いたパターン形成方法 |
| WO2019022227A1 (ja) | 2017-07-28 | 2019-01-31 | デンカ株式会社 | 重合体の製造方法 |
| US11608397B2 (en) | 2017-07-28 | 2023-03-21 | Denka Company Limited | Polymer manufacturing method |
| JP2020012024A (ja) * | 2018-07-13 | 2020-01-23 | 信越化学工業株式会社 | 酸素硬化性シリコーン組成物およびその硬化物 |
| JP2020012025A (ja) * | 2018-07-13 | 2020-01-23 | 信越化学工業株式会社 | 酸素硬化性シリコーン組成物およびその硬化物 |
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