JPS6229444B2 - - Google Patents
Info
- Publication number
- JPS6229444B2 JPS6229444B2 JP3279878A JP3279878A JPS6229444B2 JP S6229444 B2 JPS6229444 B2 JP S6229444B2 JP 3279878 A JP3279878 A JP 3279878A JP 3279878 A JP3279878 A JP 3279878A JP S6229444 B2 JPS6229444 B2 JP S6229444B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- block copolymer
- block
- free radical
- mixture
- 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.)
- Expired
Links
- 229920000642 polymer Polymers 0.000 claims description 19
- 229920001400 block copolymer Polymers 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000000178 monomer Substances 0.000 claims description 11
- 150000003254 radicals Chemical class 0.000 claims description 7
- -1 dilithium compound Chemical class 0.000 claims description 6
- 230000000977 initiatory effect Effects 0.000 claims description 5
- 150000002642 lithium compounds Chemical class 0.000 claims description 5
- 238000010526 radical polymerization reaction Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000001979 organolithium group Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000003505 polymerization initiator Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 20
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 13
- 239000005062 Polybutadiene Substances 0.000 description 12
- 229920002857 polybutadiene Polymers 0.000 description 12
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- MBNVSWHUJDDZRH-UHFFFAOYSA-N 2-methylthiirane Chemical compound CC1CS1 MBNVSWHUJDDZRH-UHFFFAOYSA-N 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 5
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000003708 ampul Substances 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 229920002725 thermoplastic elastomer Polymers 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- CSTNUSIMRBYYPH-UHFFFAOYSA-N 1-(1-phenylethenyl)-4-[4-(1-phenylethenyl)phenoxy]benzene Chemical compound C=1C=C(OC=2C=CC(=CC=2)C(=C)C=2C=CC=CC=2)C=CC=1C(=C)C1=CC=CC=C1 CSTNUSIMRBYYPH-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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 150000003464 sulfur compounds Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- GSGXSPUPTHLEIQ-UHFFFAOYSA-N CC(CC(C1=CC=CC=C1)([Li])[Li])CC Chemical compound CC(CC(C1=CC=CC=C1)([Li])[Li])CC GSGXSPUPTHLEIQ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000807 solvent casting Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003553 thiiranes Chemical class 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78281477A | 1977-03-30 | 1977-03-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS53121895A JPS53121895A (en) | 1978-10-24 |
| JPS6229444B2 true JPS6229444B2 (enrdf_load_stackoverflow) | 1987-06-26 |
Family
ID=25127248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3279878A Granted JPS53121895A (en) | 1977-03-30 | 1978-03-22 | Process for producing block copolymer |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS53121895A (enrdf_load_stackoverflow) |
| AU (1) | AU521579B2 (enrdf_load_stackoverflow) |
| BE (1) | BE865465A (enrdf_load_stackoverflow) |
| BR (1) | BR7801948A (enrdf_load_stackoverflow) |
| CA (1) | CA1098637A (enrdf_load_stackoverflow) |
| DE (1) | DE2813328C2 (enrdf_load_stackoverflow) |
| FR (1) | FR2385750A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1565042A (enrdf_load_stackoverflow) |
| NL (1) | NL186090C (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3611704A1 (de) * | 1986-04-08 | 1987-10-22 | Basf Ag | Verfahren zur herstellung von schlagfestem poly(alkyl)styrol |
| DE3611705A1 (de) * | 1986-04-08 | 1987-10-22 | Basf Ag | Verfahren zur herstellung von schlagfestem poly(alkyl)styrol |
| GB2271074B (en) * | 1992-09-24 | 1996-07-10 | Extract Technology Ltd | Glove box |
| US7951887B2 (en) | 2003-05-30 | 2011-05-31 | Nippon Soda Co., Ltd. | Process for producing a polymer |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3225120A (en) * | 1962-05-16 | 1965-12-21 | Du Pont | Thermoplastic copolymer of vinyl monomer and sulfur |
| SE339105B (enrdf_load_stackoverflow) * | 1966-02-23 | 1971-09-27 | Avisun Corp | |
| GB1234581A (enrdf_load_stackoverflow) * | 1967-09-13 | 1971-06-03 | ||
| FR2071337A5 (en) * | 1969-12-24 | 1971-09-17 | V Trudov | Hydrocarbon polymers having functional - end groups |
| JPS5645923B2 (enrdf_load_stackoverflow) * | 1973-02-12 | 1981-10-29 |
-
1978
- 1978-03-14 CA CA298,867A patent/CA1098637A/en not_active Expired
- 1978-03-22 JP JP3279878A patent/JPS53121895A/ja active Granted
- 1978-03-23 NL NL7803192A patent/NL186090C/xx not_active IP Right Cessation
- 1978-03-28 FR FR7808906A patent/FR2385750A1/fr active Granted
- 1978-03-28 DE DE19782813328 patent/DE2813328C2/de not_active Expired
- 1978-03-29 GB GB1231878A patent/GB1565042A/en not_active Expired
- 1978-03-30 BR BR7801948A patent/BR7801948A/pt unknown
- 1978-03-30 BE BE2056814A patent/BE865465A/xx not_active IP Right Cessation
- 1978-04-13 AU AU35082/78A patent/AU521579B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL186090B (nl) | 1990-04-17 |
| GB1565042A (en) | 1980-04-16 |
| AU521579B2 (en) | 1982-04-22 |
| BR7801948A (pt) | 1978-11-28 |
| NL7803192A (nl) | 1978-10-03 |
| AU3508278A (en) | 1979-10-18 |
| DE2813328A1 (de) | 1978-10-05 |
| FR2385750B1 (enrdf_load_stackoverflow) | 1980-02-01 |
| BE865465A (nl) | 1978-10-02 |
| FR2385750A1 (fr) | 1978-10-27 |
| NL186090C (nl) | 1990-09-17 |
| JPS53121895A (en) | 1978-10-24 |
| CA1098637A (en) | 1981-03-31 |
| DE2813328C2 (de) | 1986-11-27 |
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