JPS58167606A - ラジカル共重合によるグラフト共重合体の製造方法 - Google Patents
ラジカル共重合によるグラフト共重合体の製造方法Info
- Publication number
- JPS58167606A JPS58167606A JP57048136A JP4813682A JPS58167606A JP S58167606 A JPS58167606 A JP S58167606A JP 57048136 A JP57048136 A JP 57048136A JP 4813682 A JP4813682 A JP 4813682A JP S58167606 A JPS58167606 A JP S58167606A
- Authority
- JP
- Japan
- Prior art keywords
- silicone
- acrylic
- graft copolymer
- reaction
- modified silicone
- 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.)
- Granted
Links
- 229920000578 graft copolymer Polymers 0.000 title claims description 53
- 238000007334 copolymerization reaction Methods 0.000 title description 17
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 144
- 239000000178 monomer Substances 0.000 claims abstract description 30
- -1 acrylic compound Chemical class 0.000 claims abstract description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract description 4
- 150000008282 halocarbons Chemical class 0.000 claims abstract description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 238000006482 condensation reaction Methods 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 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 abstract description 13
- 239000002904 solvent Substances 0.000 abstract description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 8
- 229920001577 copolymer Polymers 0.000 abstract description 5
- 230000007062 hydrolysis Effects 0.000 abstract description 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 2
- 239000003505 polymerization initiator Substances 0.000 abstract description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- 239000004205 dimethyl polysiloxane Substances 0.000 abstract 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 35
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 34
- 238000000034 method Methods 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000002253 acid Substances 0.000 description 9
- 239000007870 radical polymerization initiator Substances 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 8
- 239000003921 oil Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229920000620 organic polymer Polymers 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- QXKMQBOTKLTKOE-UHFFFAOYSA-N 3-[dichloro(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](C)(Cl)Cl QXKMQBOTKLTKOE-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000006356 dehydrogenation reaction Methods 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 125000005372 silanol group Chemical group 0.000 description 4
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 150000001451 organic peroxides Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- WTEVQBCEXWBHNA-YFHOEESVSA-N neral Chemical compound CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000565 sealant Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- YVLJEXBGMVDKBR-UHFFFAOYSA-N 1,10-dichloro-7-methyldec-1-ene Chemical compound ClCCCC(C)CCCCC=CCl YVLJEXBGMVDKBR-UHFFFAOYSA-N 0.000 description 1
- 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
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- GBAQKTTVWCCNHH-UHFFFAOYSA-N 3-[dichloro(methyl)silyl]propyl prop-2-enoate Chemical compound C[Si](Cl)(Cl)CCCOC(=O)C=C GBAQKTTVWCCNHH-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- WTEVQBCEXWBHNA-JXMROGBWSA-N citral A Natural products CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000010556 emulsion polymerization method Methods 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- ARLJCLKHRZGWGL-UHFFFAOYSA-N ethenylsilicon Chemical class [Si]C=C ARLJCLKHRZGWGL-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Silicon Polymers (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57048136A JPS58167606A (ja) | 1982-03-27 | 1982-03-27 | ラジカル共重合によるグラフト共重合体の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57048136A JPS58167606A (ja) | 1982-03-27 | 1982-03-27 | ラジカル共重合によるグラフト共重合体の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58167606A true JPS58167606A (ja) | 1983-10-03 |
| JPH0139445B2 JPH0139445B2 (enrdf_load_stackoverflow) | 1989-08-21 |
Family
ID=12794915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57048136A Granted JPS58167606A (ja) | 1982-03-27 | 1982-03-27 | ラジカル共重合によるグラフト共重合体の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58167606A (enrdf_load_stackoverflow) |
Cited By (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60123518A (ja) * | 1983-12-09 | 1985-07-02 | Toagosei Chem Ind Co Ltd | シリコ−ン系グラフト共重合体の製造方法 |
| JPS61136510A (ja) * | 1984-12-07 | 1986-06-24 | Mitsubishi Rayon Co Ltd | 耐衝撃性樹脂の製造方法 |
| JPS61138654A (ja) * | 1984-12-10 | 1986-06-26 | Mitsubishi Rayon Co Ltd | 耐衝撃性樹脂組成物 |
| JPS61276810A (ja) * | 1983-07-20 | 1986-12-06 | ロクタイト．コ−ポレ−シヨン | 陰影領域を有する支持体の二重硬化被覆方法と該方法の実施に直接使用するポリオルガノシロキサンプレポリマ− |
| JPS6222881A (ja) * | 1985-07-19 | 1987-01-31 | ミネソタ マイニング アンド マニュファクチュアリング コンパニ− | コ−テイングされたシ−ト材料 |
| US4693935A (en) * | 1986-05-19 | 1987-09-15 | Minnesota Mining And Manufacturing Company | Polysiloxane-grafted copolymer pressure sensitive adhesive composition and sheet materials coated therewith |
| JPH01146977A (ja) * | 1987-12-02 | 1989-06-08 | Sekisui Chem Co Ltd | 粘着剤 |
| US4883852A (en) * | 1985-12-27 | 1989-11-28 | Nippon Oil And Fats Co., Ltd. | Antifouling coating |
| JPH021785A (ja) * | 1988-03-31 | 1990-01-08 | Sanyo Chem Ind Ltd | 感圧接着剤組成物 |
| JPH0280415A (ja) * | 1988-09-16 | 1990-03-20 | Shin Etsu Chem Co Ltd | メタクリル官能性ジメチルポリシロキサン |
| JPH03170518A (ja) * | 1989-11-30 | 1991-07-24 | Kobayashi Kose Co Ltd | 皮膚化粧料 |
| US5272029A (en) * | 1991-02-28 | 1993-12-21 | Canon Kabushiki Kaisha | Image-bearing member and apparatus including same |
| US5629094A (en) * | 1994-01-31 | 1997-05-13 | Canon Kabushiki Kaisha | Image transfer medium carrier member and image forming apparatus incorporating the same |
| US6001526A (en) * | 1998-03-24 | 1999-12-14 | Minolta Co., Ltd. | Binder carrier containing ethylenic unsaturated nitrile copolymer as binder resin |
| US6099999A (en) * | 1998-04-07 | 2000-08-08 | Minolta Co., Ltd. | Binder carrier comprising magnetic particles and specific resin |
| US6130019A (en) * | 1997-12-12 | 2000-10-10 | Minolta Co., Ltd. | Binder carrier |
| JP2002105206A (ja) * | 2000-09-29 | 2002-04-10 | Shin Etsu Chem Co Ltd | （メタ）アクリロキシ基含有オルガノポリシロキサン及び該ポリシロキサンの製造方法 |
| EP1153942A4 (en) * | 1998-09-02 | 2003-07-23 | Kaneka Corp | POLYMER, PROCESS FOR PRODUCING POLYMER, AND COMPOSITION |
| WO2012018043A1 (ja) | 2010-08-06 | 2012-02-09 | 綜研化学株式会社 | ナノインプリント用樹脂製モールド |
| WO2013018450A1 (en) | 2011-07-29 | 2013-02-07 | Canon Kabushiki Kaisha | Method for producing electrophotographic photosensitive member |
| US8765335B2 (en) | 2011-07-29 | 2014-07-01 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member, process cartridge and electrophotographic apparatus |
| EP2757421A1 (en) | 2013-01-18 | 2014-07-23 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member, process cartridge and electrophotographic apparatus |
| US9170507B2 (en) | 2013-01-18 | 2015-10-27 | Canon Kabushiki Kaisha | Method of producing electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus |
| US9274496B2 (en) | 2013-01-29 | 2016-03-01 | Canon Kabushiki Kaisha | Electrophotographic process cartridge and electrophotographic apparatus |
| US9411307B2 (en) | 2013-01-24 | 2016-08-09 | Canon Kabushiki Kaisha | Process cartridge and electrophotographic apparatus |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5031041A (enrdf_load_stackoverflow) * | 1973-06-26 | 1975-03-27 |
-
1982
- 1982-03-27 JP JP57048136A patent/JPS58167606A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5031041A (enrdf_load_stackoverflow) * | 1973-06-26 | 1975-03-27 |
Cited By (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61276810A (ja) * | 1983-07-20 | 1986-12-06 | ロクタイト．コ−ポレ−シヨン | 陰影領域を有する支持体の二重硬化被覆方法と該方法の実施に直接使用するポリオルガノシロキサンプレポリマ− |
| JPS60123518A (ja) * | 1983-12-09 | 1985-07-02 | Toagosei Chem Ind Co Ltd | シリコ−ン系グラフト共重合体の製造方法 |
| JPS61136510A (ja) * | 1984-12-07 | 1986-06-24 | Mitsubishi Rayon Co Ltd | 耐衝撃性樹脂の製造方法 |
| JPS61138654A (ja) * | 1984-12-10 | 1986-06-26 | Mitsubishi Rayon Co Ltd | 耐衝撃性樹脂組成物 |
| US4728571A (en) * | 1985-07-19 | 1988-03-01 | Minnesota Mining And Manufacturing Company | Polysiloxane-grafted copolymer release coating sheets and adhesive tapes |
| JPS6222881A (ja) * | 1985-07-19 | 1987-01-31 | ミネソタ マイニング アンド マニュファクチュアリング コンパニ− | コ−テイングされたシ−ト材料 |
| US4883852A (en) * | 1985-12-27 | 1989-11-28 | Nippon Oil And Fats Co., Ltd. | Antifouling coating |
| US4693935A (en) * | 1986-05-19 | 1987-09-15 | Minnesota Mining And Manufacturing Company | Polysiloxane-grafted copolymer pressure sensitive adhesive composition and sheet materials coated therewith |
| JPH01146977A (ja) * | 1987-12-02 | 1989-06-08 | Sekisui Chem Co Ltd | 粘着剤 |
| JPH021785A (ja) * | 1988-03-31 | 1990-01-08 | Sanyo Chem Ind Ltd | 感圧接着剤組成物 |
| JPH0280415A (ja) * | 1988-09-16 | 1990-03-20 | Shin Etsu Chem Co Ltd | メタクリル官能性ジメチルポリシロキサン |
| JPH03170518A (ja) * | 1989-11-30 | 1991-07-24 | Kobayashi Kose Co Ltd | 皮膚化粧料 |
| US5272029A (en) * | 1991-02-28 | 1993-12-21 | Canon Kabushiki Kaisha | Image-bearing member and apparatus including same |
| US5629094A (en) * | 1994-01-31 | 1997-05-13 | Canon Kabushiki Kaisha | Image transfer medium carrier member and image forming apparatus incorporating the same |
| US6130019A (en) * | 1997-12-12 | 2000-10-10 | Minolta Co., Ltd. | Binder carrier |
| US6001526A (en) * | 1998-03-24 | 1999-12-14 | Minolta Co., Ltd. | Binder carrier containing ethylenic unsaturated nitrile copolymer as binder resin |
| US6099999A (en) * | 1998-04-07 | 2000-08-08 | Minolta Co., Ltd. | Binder carrier comprising magnetic particles and specific resin |
| EP1153942A4 (en) * | 1998-09-02 | 2003-07-23 | Kaneka Corp | POLYMER, PROCESS FOR PRODUCING POLYMER, AND COMPOSITION |
| US6930147B1 (en) | 1998-09-02 | 2005-08-16 | Kaneka Corporation | Polymer, processes for producing polymer, and composition |
| EP1764377A1 (en) * | 1998-09-02 | 2007-03-21 | Kaneka Corporation | Polymer, process for producing polymer and composition |
| US7223817B2 (en) | 1998-09-02 | 2007-05-29 | Kaneka Corporation | Polymer, processes for producing polymer and composition |
| JP2002105206A (ja) * | 2000-09-29 | 2002-04-10 | Shin Etsu Chem Co Ltd | （メタ）アクリロキシ基含有オルガノポリシロキサン及び該ポリシロキサンの製造方法 |
| US9393737B2 (en) | 2010-08-06 | 2016-07-19 | Soken Chemical & Engineering Co., Ltd. | Resin mold for nanoimprinting |
| WO2012018043A1 (ja) | 2010-08-06 | 2012-02-09 | 綜研化学株式会社 | ナノインプリント用樹脂製モールド |
| WO2013018450A1 (en) | 2011-07-29 | 2013-02-07 | Canon Kabushiki Kaisha | Method for producing electrophotographic photosensitive member |
| US8765335B2 (en) | 2011-07-29 | 2014-07-01 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member, process cartridge and electrophotographic apparatus |
| US8632935B2 (en) | 2011-07-29 | 2014-01-21 | Canon Kabushiki Kaisha | Method for producing electrophotographic photosensitive member |
| EP2757421A1 (en) | 2013-01-18 | 2014-07-23 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member, process cartridge and electrophotographic apparatus |
| US9170507B2 (en) | 2013-01-18 | 2015-10-27 | Canon Kabushiki Kaisha | Method of producing electrophotographic photosensitive member, process cartridge, and electrophotographic apparatus |
| US9170506B2 (en) | 2013-01-18 | 2015-10-27 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member, process cartridge and electrophotographic apparatus |
| US9411307B2 (en) | 2013-01-24 | 2016-08-09 | Canon Kabushiki Kaisha | Process cartridge and electrophotographic apparatus |
| US9274496B2 (en) | 2013-01-29 | 2016-03-01 | Canon Kabushiki Kaisha | Electrophotographic process cartridge and electrophotographic apparatus |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0139445B2 (enrdf_load_stackoverflow) | 1989-08-21 |
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