JPS6154819B2 - - Google Patents
Info
- Publication number
- JPS6154819B2 JPS6154819B2 JP52033169A JP3316977A JPS6154819B2 JP S6154819 B2 JPS6154819 B2 JP S6154819B2 JP 52033169 A JP52033169 A JP 52033169A JP 3316977 A JP3316977 A JP 3316977A JP S6154819 B2 JPS6154819 B2 JP S6154819B2
- Authority
- JP
- Japan
- Prior art keywords
- rubber
- polymer
- monomer
- molecular weight
- particles
- 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
- 229920001971 elastomer Polymers 0.000 claims description 96
- 239000005060 rubber Substances 0.000 claims description 96
- 229920000642 polymer Polymers 0.000 claims description 75
- 239000002245 particle Substances 0.000 claims description 60
- 239000000178 monomer Substances 0.000 claims description 59
- 239000000203 mixture Substances 0.000 claims description 37
- 229920003244 diene elastomer Polymers 0.000 claims description 21
- 229920002857 polybutadiene Polymers 0.000 claims description 19
- 239000006185 dispersion Substances 0.000 claims description 18
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 238000009826 distribution Methods 0.000 claims description 14
- 239000005062 Polybutadiene Substances 0.000 claims description 9
- 230000008961 swelling Effects 0.000 claims description 7
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 2
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 claims description 2
- CYLVUSZHVURAOY-UHFFFAOYSA-N 2,2-dibromoethenylbenzene Chemical compound BrC(Br)=CC1=CC=CC=C1 CYLVUSZHVURAOY-UHFFFAOYSA-N 0.000 claims 1
- CISIJYCKDJSTMX-UHFFFAOYSA-N 2,2-dichloroethenylbenzene Chemical compound ClC(Cl)=CC1=CC=CC=C1 CISIJYCKDJSTMX-UHFFFAOYSA-N 0.000 claims 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 claims 1
- YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 claims 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 22
- 238000006116 polymerization reaction Methods 0.000 description 19
- 239000000499 gel Substances 0.000 description 14
- 239000004793 Polystyrene Substances 0.000 description 12
- 229920002223 polystyrene Polymers 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000013019 agitation Methods 0.000 description 6
- 229920005669 high impact polystyrene Polymers 0.000 description 6
- 239000004797 high-impact polystyrene Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000012662 bulk polymerization Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 229920000578 graft copolymer Polymers 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- -1 halofenyl Chemical group 0.000 description 2
- 239000007970 homogeneous dispersion Substances 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000003014 reinforcing effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000011240 wet gel Substances 0.000 description 2
- VJDVKNLYGQTELS-UHFFFAOYSA-N 1,3-dichloro-2-ethenyl-5-methylbenzene Chemical compound CC1=CC(Cl)=C(C=C)C(Cl)=C1 VJDVKNLYGQTELS-UHFFFAOYSA-N 0.000 description 1
- SSZOCHFYWWVSAI-UHFFFAOYSA-N 1-bromo-2-ethenylbenzene Chemical compound BrC1=CC=CC=C1C=C SSZOCHFYWWVSAI-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
- OEVVKKAVYQFQNV-UHFFFAOYSA-N 1-ethenyl-2,4-dimethylbenzene Chemical compound CC1=CC=C(C=C)C(C)=C1 OEVVKKAVYQFQNV-UHFFFAOYSA-N 0.000 description 1
- VTPNYMSKBPZSTF-UHFFFAOYSA-N 1-ethenyl-2-ethylbenzene Chemical compound CCC1=CC=CC=C1C=C VTPNYMSKBPZSTF-UHFFFAOYSA-N 0.000 description 1
- WHFHDVDXYKOSKI-UHFFFAOYSA-N 1-ethenyl-4-ethylbenzene Chemical compound CCC1=CC=C(C=C)C=C1 WHFHDVDXYKOSKI-UHFFFAOYSA-N 0.000 description 1
- OMNYXCUDBQKCMU-UHFFFAOYSA-N 2,4-dichloro-1-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C(Cl)=C1 OMNYXCUDBQKCMU-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-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
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- SZSWKGVWJBZNIH-UHFFFAOYSA-N 2-chloro-1-ethenyl-4-methylbenzene Chemical compound CC1=CC=C(C=C)C(Cl)=C1 SZSWKGVWJBZNIH-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
- FRQQKWGDKVGLFI-UHFFFAOYSA-N 2-methylundecane-2-thiol Chemical compound CCCCCCCCCC(C)(C)S FRQQKWGDKVGLFI-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- SQHOHKQMTHROSF-UHFFFAOYSA-N but-1-en-2-ylbenzene Chemical compound CCC(=C)C1=CC=CC=C1 SQHOHKQMTHROSF-UHFFFAOYSA-N 0.000 description 1
- VUKHQPGJNTXTPY-UHFFFAOYSA-N but-2-enylbenzene Chemical compound CC=CCC1=CC=CC=C1 VUKHQPGJNTXTPY-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000011953 free-radical catalyst Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000012844 infrared spectroscopy analysis Methods 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/04—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to rubbers
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)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/670,938 US4125573A (en) | 1976-03-26 | 1976-03-26 | Polymer polyblend composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS52117347A JPS52117347A (en) | 1977-10-01 |
JPS6154819B2 true JPS6154819B2 (US20080293856A1-20081127-C00127.png) | 1986-11-25 |
Family
ID=24692500
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP3316977A Granted JPS52117347A (en) | 1976-03-26 | 1977-03-25 | Improved polymeric polyblends composition |
Country Status (13)
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6392624U (US20080293856A1-20081127-C00127.png) * | 1986-12-05 | 1988-06-15 |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6023693B2 (ja) * | 1977-04-20 | 1985-06-08 | 旭化成株式会社 | 耐衝撃性ポリスチレン組成物の製造方法 |
JPS6023691B2 (ja) * | 1977-04-20 | 1985-06-08 | 旭化成株式会社 | 耐衝撃性ポリスチレンの製造方法 |
EP0000976B1 (en) * | 1977-07-26 | 1982-05-19 | The Malaysian Rubber Producers' Research Association | A method of forming graft copolymers by attaching pre-polymerised side chains to an unsaturated natural or synthetic rubber backbone, and the resulting graft copolymers |
JPS5556114A (en) * | 1978-10-20 | 1980-04-24 | Asahi Chem Ind Co Ltd | Preparation of high-impact polystyrene resin |
US4275319A (en) * | 1979-06-01 | 1981-06-23 | Trw Inc. | Oil-filled submergible electric pump motor with improved stator winding insulation |
JPH0686559B2 (ja) * | 1984-09-27 | 1994-11-02 | 出光石油化学株式会社 | 耐フロン性シート材料 |
US4717741A (en) * | 1985-05-16 | 1988-01-05 | The Dow Chemical Company | Rubber modified styrenic polymer compositions formed from hydroperoxide derivatives of rubbery polymers |
US4826920A (en) * | 1987-12-18 | 1989-05-02 | Mobil Oil Corporation | Films of linear ethylene polymer, polystyrene, and high impact polystyrene |
US5986000A (en) | 1995-05-22 | 1999-11-16 | Playtex Products, Inc. | Soft, flexible composition and method for making same |
WO2014074872A1 (en) | 2012-11-09 | 2014-05-15 | Bridgestone Corporation | Uses of biobased styryene |
US8962067B2 (en) * | 2013-01-24 | 2015-02-24 | Tokyo Electron Limited | Real time process control of the polymer dispersion index |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3243481A (en) * | 1962-01-08 | 1966-03-29 | Dow Chemical Co | Process for making graft copolymers of vinyl aromatic compounds and stereospecific rubbers |
US3189592A (en) * | 1962-08-23 | 1965-06-15 | Phillips Petroleum Co | Production of bimodal cispolybutadiene |
US3311675A (en) * | 1963-04-16 | 1967-03-28 | Rexall Drug Chemical | Bulk solvent polymerization process |
US3868434A (en) * | 1965-05-21 | 1975-02-25 | Foster Grant Co Inc | Polymer composition and process |
US3488743A (en) * | 1966-06-14 | 1970-01-06 | Monsanto Co | Process for producing high impact strength graft copolymers with low molecular weight rubbers |
US3903202A (en) * | 1973-09-19 | 1975-09-02 | Monsanto Co | Continuous mass polymerization process for polyblends |
US3928495A (en) * | 1974-04-26 | 1975-12-23 | Monsanto Co | Continuous process for the preparation of ABS type polyblends |
US3931356A (en) * | 1974-04-26 | 1976-01-06 | Monsanto Company | Continuous process for the preparation of ABS type polyblends |
-
1976
- 1976-03-26 US US05/670,938 patent/US4125573A/en not_active Expired - Lifetime
-
1977
- 1977-03-25 AU AU23632/77A patent/AU513014B2/en not_active Expired
- 1977-03-25 DE DE19772713258 patent/DE2713258A1/de not_active Ceased
- 1977-03-25 GB GB12578/77A patent/GB1545011A/en not_active Expired
- 1977-03-25 JP JP3316977A patent/JPS52117347A/ja active Granted
- 1977-03-25 CA CA274,817A patent/CA1077188A/en not_active Expired
- 1977-03-25 MX MX168524A patent/MX145402A/es unknown
- 1977-03-25 IT IT21720/77A patent/IT1075680B/it active
- 1977-03-25 SE SE7703440A patent/SE427667B/xx not_active IP Right Cessation
- 1977-03-25 IL IL51742A patent/IL51742A/xx unknown
- 1977-03-25 BR BR7701889A patent/BR7701889A/pt unknown
- 1977-03-25 FR FR7709109A patent/FR2345484A1/fr active Granted
- 1977-03-25 BE BE176144A patent/BE852907A/xx not_active IP Right Cessation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6392624U (US20080293856A1-20081127-C00127.png) * | 1986-12-05 | 1988-06-15 |
Also Published As
Publication number | Publication date |
---|---|
BE852907A (fr) | 1977-09-26 |
MX145402A (es) | 1982-02-04 |
JPS52117347A (en) | 1977-10-01 |
AU513014B2 (en) | 1980-11-06 |
SE427667B (sv) | 1983-04-25 |
IL51742A0 (en) | 1977-05-31 |
IT1075680B (it) | 1985-04-22 |
BR7701889A (pt) | 1978-01-03 |
GB1545011A (en) | 1979-05-02 |
FR2345484B1 (US20080293856A1-20081127-C00127.png) | 1983-11-25 |
DE2713258A1 (de) | 1977-09-29 |
CA1077188A (en) | 1980-05-06 |
SE7703440L (sv) | 1977-09-27 |
FR2345484A1 (fr) | 1977-10-21 |
AU2363277A (en) | 1978-09-28 |
US4125573A (en) | 1978-11-14 |
IL51742A (en) | 1980-01-31 |
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