CA1285083C - Polymere greffe a du noir de carbone, methode pour sa production et son utilisation - Google Patents

Polymere greffe a du noir de carbone, methode pour sa production et son utilisation

Info

Publication number: CA1285083C
Authority: CA; Canada
Prior art keywords: carbon black; group; polymer; parts; reactive group
Prior art date: 1986-12-17
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 - Fee Related

Application number

CA000554540A

Other languages

English (en)

Inventor

Yoshikuni Mori

Hayato Ikeda

Yoshinori Sano

Kiyoshi Kawamura

Mitsuo Kushino

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.)

Nippon Shokubai Co Ltd

Original Assignee

Nippon Shokubai Co Ltd

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.)

1986-12-17

Filing date

1987-12-16

Publication date

1991-06-18

1987-04-24 Priority claimed from JP62099648A external-priority patent/JPH0627269B2/ja

1987-09-03 Priority claimed from JP62219097A external-priority patent/JPS63270767A/ja

1987-12-16 Application filed by Nippon Shokubai Co Ltd filed Critical Nippon Shokubai Co Ltd

1991-06-18 Application granted granted Critical

1991-06-18 Publication of CA1285083C publication Critical patent/CA1285083C/fr

2008-06-18 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims abstract description 142
229910052799 carbon Inorganic materials 0.000 title claims abstract description 138
229920000578 graft copolymer Polymers 0.000 title claims abstract description 124
238000004519 manufacturing process Methods 0.000 title claims description 18
229920000642 polymer Polymers 0.000 claims abstract description 188
125000003700 epoxy group Chemical group 0.000 claims abstract description 32
125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 claims abstract description 23
125000005068 thioepoxy group Chemical group S(O*)* 0.000 claims abstract description 19
125000004069 aziridinyl group Chemical group 0.000 claims abstract description 16
239000006229 carbon black Substances 0.000 claims description 137
238000000034 method Methods 0.000 claims description 84
238000006243 chemical reaction Methods 0.000 claims description 34
229920000728 polyester Polymers 0.000 claims description 18
238000011161 development Methods 0.000 claims description 17
229920001577 copolymer Polymers 0.000 claims description 13
229920002554 vinyl polymer Polymers 0.000 claims description 11
229920000570 polyether Polymers 0.000 claims description 6
IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical group C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 2
238000010094 polymer processing Methods 0.000 claims 1
229940105289 carbon black Drugs 0.000 description 126
235000019241 carbon black Nutrition 0.000 description 126
229920005989 resin Polymers 0.000 description 52
239000011347 resin Substances 0.000 description 52
239000000203 mixture Substances 0.000 description 45
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 40
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 38
239000003795 chemical substances by application Substances 0.000 description 38
239000000178 monomer Substances 0.000 description 36
239000011230 binding agent Substances 0.000 description 31
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
239000011248 coating agent Substances 0.000 description 29
239000000976 ink Substances 0.000 description 28
239000006185 dispersion Substances 0.000 description 27
229920001971 elastomer Polymers 0.000 description 26
239000005060 rubber Substances 0.000 description 25
239000000126 substance Substances 0.000 description 25
230000000694 effects Effects 0.000 description 24
239000000243 solution Substances 0.000 description 24
239000000725 suspension Substances 0.000 description 21
238000002156 mixing Methods 0.000 description 20
239000011369 resultant mixture Substances 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 18
238000012360 testing method Methods 0.000 description 18
230000018109 developmental process Effects 0.000 description 16
239000002245 particle Substances 0.000 description 16
238000012546 transfer Methods 0.000 description 16
239000008199 coating composition Substances 0.000 description 15
239000000047 product Substances 0.000 description 15
229920001187 thermosetting polymer Polymers 0.000 description 15
229920005992 thermoplastic resin Polymers 0.000 description 14
230000005291 magnetic effect Effects 0.000 description 13
239000011572 manganese Substances 0.000 description 13
238000006116 polymerization reaction Methods 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 12
239000000758 substrate Substances 0.000 description 12
-1 ~ -methyl styrene Chemical compound 0.000 description 12
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 11
150000001875 compounds Chemical class 0.000 description 11
239000011342 resin composition Substances 0.000 description 11
238000000576 coating method Methods 0.000 description 10
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 10
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
229910001873 dinitrogen Inorganic materials 0.000 description 8
239000006249 magnetic particle Substances 0.000 description 8
239000002202 Polyethylene glycol Substances 0.000 description 7
239000004793 Polystyrene Substances 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
229920001223 polyethylene glycol Polymers 0.000 description 7
229920002223 polystyrene Polymers 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
230000009257 reactivity Effects 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
239000004342 Benzoyl peroxide Substances 0.000 description 6
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 6
230000032683 aging Effects 0.000 description 6
235000019400 benzoyl peroxide Nutrition 0.000 description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
239000011247 coating layer Substances 0.000 description 6
239000008367 deionised water Substances 0.000 description 6
229910021641 deionized water Inorganic materials 0.000 description 6
235000011121 sodium hydroxide Nutrition 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000001993 wax Substances 0.000 description 6
239000004372 Polyvinyl alcohol Substances 0.000 description 5
241000872198 Serjania polyphylla Species 0.000 description 5
239000003086 colorant Substances 0.000 description 5
238000007796 conventional method Methods 0.000 description 5
238000001914 filtration Methods 0.000 description 5
238000010348 incorporation Methods 0.000 description 5
238000004898 kneading Methods 0.000 description 5
239000000463 material Substances 0.000 description 5
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 5
229920002451 polyvinyl alcohol Polymers 0.000 description 5
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
239000004698 Polyethylene Substances 0.000 description 4
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 4
WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
239000000835 fiber Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
229920000573 polyethylene Polymers 0.000 description 4
229920003048 styrene butadiene rubber Polymers 0.000 description 4
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
239000005062 Polybutadiene Substances 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
238000004040 coloring Methods 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
229920002521 macromolecule Polymers 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
239000004033 plastic Substances 0.000 description 3
229920002857 polybutadiene Polymers 0.000 description 3
229920001721 polyimide Polymers 0.000 description 3
229920002635 polyurethane Polymers 0.000 description 3
239000004814 polyurethane Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
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 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
239000004593 Epoxy Substances 0.000 description 2
229920000181 Ethylene propylene rubber Polymers 0.000 description 2
244000043261 Hevea brasiliensis Species 0.000 description 2
229920000877 Melamine resin Polymers 0.000 description 2
239000004640 Melamine resin Substances 0.000 description 2
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
229920000459 Nitrile rubber Polymers 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
239000004952 Polyamide Substances 0.000 description 2
239000004743 Polypropylene Substances 0.000 description 2
239000002174 Styrene-butadiene Substances 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
239000001361 adipic acid Substances 0.000 description 2
235000011037 adipic acid Nutrition 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
229920005549 butyl rubber Polymers 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
BTVWZWFKMIUSGS-UHFFFAOYSA-N dimethylethyleneglycol Natural products CC(C)(O)CO BTVWZWFKMIUSGS-UHFFFAOYSA-N 0.000 description 2
239000003822 epoxy resin Substances 0.000 description 2
SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
239000000945 filler Substances 0.000 description 2
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 2
239000011874 heated mixture Substances 0.000 description 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000011261 inert gas Substances 0.000 description 2
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
239000006247 magnetic powder Substances 0.000 description 2
239000011159 matrix material Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
BSCJIBOZTKGXQP-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCCO BSCJIBOZTKGXQP-UHFFFAOYSA-N 0.000 description 2
229920003052 natural elastomer Polymers 0.000 description 2
229920001194 natural rubber Polymers 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
239000000049 pigment Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
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229920000515 polycarbonate Polymers 0.000 description 2
239000004417 polycarbonate Substances 0.000 description 2
238000006068 polycondensation reaction Methods 0.000 description 2
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230000000379 polymerizing effect Effects 0.000 description 2
229920000098 polyolefin Polymers 0.000 description 2
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230000008569 process Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000012744 reinforcing agent Substances 0.000 description 2
230000003014 reinforcing effect Effects 0.000 description 2
239000004576 sand Substances 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000007921 spray Substances 0.000 description 2
230000003068 static effect Effects 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
238000011282 treatment Methods 0.000 description 2
229920006305 unsaturated polyester Polymers 0.000 description 2
229920006337 unsaturated polyester resin Polymers 0.000 description 2
238000004073 vulcanization Methods 0.000 description 2
239000002023 wood Substances 0.000 description 2
229910000859 α-Fe Inorganic materials 0.000 description 2
YVLJEXBGMVDKBR-UHFFFAOYSA-N 1,10-dichloro-7-methyldec-1-ene Chemical compound ClCCCC(C)CCCCC=CCl YVLJEXBGMVDKBR-UHFFFAOYSA-N 0.000 description 1
BOVQCIDBZXNFEJ-UHFFFAOYSA-N 1-chloro-3-ethenylbenzene Chemical compound ClC1=CC=CC(C=C)=C1 BOVQCIDBZXNFEJ-UHFFFAOYSA-N 0.000 description 1
KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 description 1
NHZLLKNRTDIFAD-UHFFFAOYSA-N 2,5-dihydro-1,3-oxazole Chemical group C1OCN=C1 NHZLLKNRTDIFAD-UHFFFAOYSA-N 0.000 description 1
KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 1
GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
CCJAYIGMMRQRAO-UHFFFAOYSA-N 2-[4-[(2-hydroxyphenyl)methylideneamino]butyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCCCN=CC1=CC=CC=C1O CCJAYIGMMRQRAO-UHFFFAOYSA-N 0.000 description 1
ISRGONDNXBCDBM-UHFFFAOYSA-N 2-chlorostyrene Chemical compound ClC1=CC=CC=C1C=C ISRGONDNXBCDBM-UHFFFAOYSA-N 0.000 description 1
BQBSIHIZDSHADD-UHFFFAOYSA-N 2-ethenyl-4,5-dihydro-1,3-oxazole Chemical compound C=CC1=NCCO1 BQBSIHIZDSHADD-UHFFFAOYSA-N 0.000 description 1
NVADAERBBAQCLW-UHFFFAOYSA-N 2-ethenyl-4-ethyl-4,5-dihydro-1,3-oxazole Chemical compound CCC1COC(C=C)=N1 NVADAERBBAQCLW-UHFFFAOYSA-N 0.000 description 1
PBYIFPWEHGSUEY-UHFFFAOYSA-N 2-ethenyl-4-methyl-4,5-dihydro-1,3-oxazole Chemical compound CC1COC(C=C)=N1 PBYIFPWEHGSUEY-UHFFFAOYSA-N 0.000 description 1
HFRTWUSGUFBWTL-UHFFFAOYSA-N 2-ethenyl-5-ethyl-4,5-dihydro-1,3-oxazole Chemical compound CCC1CN=C(C=C)O1 HFRTWUSGUFBWTL-UHFFFAOYSA-N 0.000 description 1
HMEVYZZCEGUONQ-UHFFFAOYSA-N 2-ethenyl-5-methyl-4,5-dihydro-1,3-oxazole Chemical compound CC1CN=C(C=C)O1 HMEVYZZCEGUONQ-UHFFFAOYSA-N 0.000 description 1
WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
LPIQIQPLUVLISR-UHFFFAOYSA-N 2-prop-1-en-2-yl-4,5-dihydro-1,3-oxazole Chemical compound CC(=C)C1=NCCO1 LPIQIQPLUVLISR-UHFFFAOYSA-N 0.000 description 1
JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
PTTDUFDXZBSJTM-UHFFFAOYSA-N 4-ethyl-2-prop-1-en-2-yl-4,5-dihydro-1,3-oxazole Chemical compound CCC1COC(C(C)=C)=N1 PTTDUFDXZBSJTM-UHFFFAOYSA-N 0.000 description 1
MBLQIMSKMPEILU-UHFFFAOYSA-N 4-methyl-2-prop-1-en-2-yl-4,5-dihydro-1,3-oxazole Chemical compound CC1COC(C(C)=C)=N1 MBLQIMSKMPEILU-UHFFFAOYSA-N 0.000 description 1
IRHWINGBSHBXAD-UHFFFAOYSA-N 5-ethyl-2-prop-1-en-2-yl-4,5-dihydro-1,3-oxazole Chemical compound CCC1CN=C(C(C)=C)O1 IRHWINGBSHBXAD-UHFFFAOYSA-N 0.000 description 1
OEIDKVHIXLGFQK-UHFFFAOYSA-N 5-methyl-2-prop-1-en-2-yl-4,5-dihydro-1,3-oxazole Chemical compound CC1CN=C(C(C)=C)O1 OEIDKVHIXLGFQK-UHFFFAOYSA-N 0.000 description 1
JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 1
GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
101150034533 ATIC gene Proteins 0.000 description 1
239000004925 Acrylic resin Substances 0.000 description 1
229920000178 Acrylic resin Polymers 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
229920002799 BoPET Polymers 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
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RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 1
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KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
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OXUABORVCCLQJI-UHFFFAOYSA-N thiiran-2-ylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1CS1 OXUABORVCCLQJI-UHFFFAOYSA-N 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
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229920001567 vinyl ester resin Polymers 0.000 description 1

Landscapes

Pigments, Carbon Blacks, Or Wood Stains (AREA)
Compositions Of Macromolecular Compounds (AREA)

CA000554540A 1986-12-17 1987-12-16 Polymere greffe a du noir de carbone, methode pour sa production et son utilisation Expired - Fee Related CA1285083C (fr)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
JP29898586		1986-12-17
JP298,985/1986		1986-12-17
JP99,648/1987		1987-04-24
JP62099648A JPH0627269B2 (ja)	1987-04-24	1987-04-24	カ−ボンブラツクグラフトポリマ−の製造方法
JP62219097A JPS63270767A (ja)	1986-12-17	1987-09-03	カーボンブラックグラフトポリマー及びその製造方法
JP219,097/1987		1987-09-03

Publications (1)

Publication Number	Publication Date
CA1285083C true CA1285083C (fr)	1991-06-18

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CA000554540A Expired - Fee Related CA1285083C (fr)	1986-12-17	1987-12-16	Polymere greffe a du noir de carbone, methode pour sa production et son utilisation

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CA (1)	CA1285083C (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN117163464A (zh) *	2023-09-12	2023-12-05	常州迪瑞尔医用新材料有限公司	一种抗静电柔性隔离袋及其生产工艺

1987
- 1987-12-16 CA CA000554540A patent/CA1285083C/fr not_active Expired - Fee Related

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN117163464A (zh) *	2023-09-12	2023-12-05	常州迪瑞尔医用新材料有限公司	一种抗静电柔性隔离袋及其生产工艺
CN117163464B (zh) *	2023-09-12	2025-10-28	常州迪瑞尔医用新材料有限公司	一种抗静电柔性隔离袋及其生产工艺

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US4940749A (en)	1990-07-10	Carbon black-graft polymer, method for production thereof, and use thereof
EP0289624B1 (fr)	1992-08-12	Fines particules spheriques colorees, procede de production et utilisations
EP0978766B1 (fr)	2007-03-21	Toner pour developpement d'image electrostatique, contenant de la resine a base de polyolefine a structure cyclique
AU667908B2 (en)	1996-04-18	Encapsulated magnetic particles, pigments and carbon black, compositions and methods related thereto
US5370958A (en)	1994-12-06	Electrophotographic toner and production process thereof
US5482809A (en)	1996-01-09	Liquid toners from soluble polymeric dispersants with reactive groups
CA1305269C (fr)	1992-07-14	Toner electrophotographique
US5416166A (en)	1995-05-16	Process for preparing a binder resin useful in electrophotographic toner
CA1285083C (fr)	1991-06-18	Polymere greffe a du noir de carbone, methode pour sa production et son utilisation
US5272212A (en)	1993-12-21	Colored spherical fine particles, process for production thereof and applications thereof
JP4781534B2 (ja)	2011-09-28	エポキシ系液体トナー配合物
CA1118483A (fr)	1982-02-16	Revelateur d'images electrostatiques et methode de fabrication de ce revelateur
JP3622324B2 (ja)	2005-02-23	被覆顔料、それを含む着色用顔料組成物ならびに被覆剤
JPH01284564A (ja)	1989-11-15	表面処理されたカーボンブラック、その製造方法及びその用途
JP2532521B2 (ja)	1996-09-11	表面処理された無機填顔料の製造方法
JPS6394251A (ja)	1988-04-25	トナ−
US3950594A (en)	1976-04-13	Dielectric coating composition
JP3338507B2 (ja)	2002-10-28	カーボンブラックグラフトポリマー組成物の製造方法
JPH0756010B2 (ja)	1995-06-14	紙塗工用組成物用の高分子顔料及びその製造方法
JP2005017773A (ja)	2005-01-20	表面に凹凸を有する粒子及びその製造方法
JPWO1988003545A1 (ja)	1988-10-06	着色球状微粒子の製造方法
JPH0447305B2 (fr)	1992-08-03
JPH0447306B2 (fr)	1992-08-03
JPH0447308B2 (fr)	1992-08-03
JPH0447309B2 (fr)	1992-08-03