FR2479238A1 - Procede de preparation de resines styreniques renforcees par du caoutchouc et resines obtenues par ce procede - Google Patents
Procede de preparation de resines styreniques renforcees par du caoutchouc et resines obtenues par ce procede Download PDFInfo
- Publication number
- FR2479238A1 FR2479238A1 FR8105933A FR8105933A FR2479238A1 FR 2479238 A1 FR2479238 A1 FR 2479238A1 FR 8105933 A FR8105933 A FR 8105933A FR 8105933 A FR8105933 A FR 8105933A FR 2479238 A1 FR2479238 A1 FR 2479238A1
- Authority
- FR
- France
- Prior art keywords
- suspension
- polymerization
- monomer
- inhibitor
- period
- 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
- 229920001971 elastomer Polymers 0.000 title abstract description 13
- 238000000034 method Methods 0.000 title description 26
- 229920001890 Novodur Polymers 0.000 title description 13
- 229920005989 resin Polymers 0.000 title description 8
- 239000011347 resin Substances 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title description 7
- 239000000178 monomer Substances 0.000 abstract description 71
- 238000006116 polymerization reaction Methods 0.000 abstract description 48
- 239000003112 inhibitor Substances 0.000 abstract description 45
- 239000000725 suspension Substances 0.000 abstract description 44
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 16
- 238000010521 absorption reaction Methods 0.000 abstract description 12
- 229920000642 polymer Polymers 0.000 abstract description 12
- 239000011145 styrene acrylonitrile resin Substances 0.000 abstract description 3
- 238000010517 secondary reaction Methods 0.000 abstract description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 45
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 24
- 239000003795 chemical substances by application Substances 0.000 description 21
- 238000000354 decomposition reaction Methods 0.000 description 15
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 14
- 238000001816 cooling Methods 0.000 description 14
- 229920001577 copolymer Polymers 0.000 description 14
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 12
- 235000010288 sodium nitrite Nutrition 0.000 description 12
- 239000011159 matrix material Substances 0.000 description 11
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 8
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000004132 cross linking Methods 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000011324 bead Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 150000001993 dienes Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 5
- 239000012508 resin bead Substances 0.000 description 5
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 5
- 238000010557 suspension polymerization reaction Methods 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 4
- 125000005907 alkyl ester group Chemical group 0.000 description 4
- -1 alkyl radical Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000007872 degassing Methods 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 3
- 150000002826 nitrites Chemical class 0.000 description 3
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- DGSDBJMBHCQYGN-UHFFFAOYSA-M sodium;2-ethylhexyl sulfate Chemical compound [Na+].CCCCC(CC)COS([O-])(=O)=O DGSDBJMBHCQYGN-UHFFFAOYSA-M 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
- WROUWQQRXUBECT-UHFFFAOYSA-M 2-ethylacrylate Chemical compound CCC(=C)C([O-])=O WROUWQQRXUBECT-UHFFFAOYSA-M 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 230000001627 detrimental effect Effects 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 2
- XHRCFGDFESIFRG-UHFFFAOYSA-N 2-chloro-n-ethyl-n-[(2-methylphenyl)methyl]ethanamine Chemical compound ClCCN(CC)CC1=CC=CC=C1C XHRCFGDFESIFRG-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 1
- JSTCPNFNKICNNO-UHFFFAOYSA-N 4-nitrosophenol Chemical compound OC1=CC=C(N=O)C=C1 JSTCPNFNKICNNO-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010952 in-situ formation Methods 0.000 description 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002978 peroxides Chemical group 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 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
- C08F257/00—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00
- C08F257/02—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00 on to polymers of styrene or alkyl-substituted styrenes
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)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/134,472 US4247668A (en) | 1980-03-27 | 1980-03-27 | Process for preparing styrenic resins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2479238A1 true FR2479238A1 (fr) | 1981-10-02 |
| FR2479238B3 FR2479238B3 (OSRAM) | 1983-12-09 |
Family
ID=22463545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8105933A Granted FR2479238A1 (fr) | 1980-03-27 | 1981-03-25 | Procede de preparation de resines styreniques renforcees par du caoutchouc et resines obtenues par ce procede |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4247668A (OSRAM) |
| JP (1) | JPS56159208A (OSRAM) |
| BE (1) | BE888123A (OSRAM) |
| DE (1) | DE3112250A1 (OSRAM) |
| FR (1) | FR2479238A1 (OSRAM) |
| GB (1) | GB2072687B (OSRAM) |
| IT (1) | IT1136948B (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4354005A (en) * | 1981-10-09 | 1982-10-12 | Cosden Technology, Inc. | Method for controlling adduct formation in production of acrylonitrile-butadiene-styrene-acrylate copolymers |
| FR2515657B1 (fr) * | 1981-11-03 | 1987-07-17 | Kendall & Co | Procede de polymerisation en emulsion et produit obtenu |
| WO2017081611A1 (en) | 2015-11-12 | 2017-05-18 | Sabic Global Technologies B.V. | Methods for using nitric oxide to inhibit popcorn polymerization during butadiene processing |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA565897A (en) * | 1958-11-11 | D. D'ianni James | Butadiene grafted on styrene-acrylonitrile copolymer | |
| CA710894A (en) * | 1965-06-01 | Peyrade Jean | Graft copolymers of dienes on vinyl-type polymers | |
| GB757531A (en) * | 1953-12-30 | 1956-09-19 | Harold Newby | Improvements in the production of modified polystyrene |
| US3538194A (en) * | 1967-03-20 | 1970-11-03 | Copolymer Rubber & Chem Corp | Preparation of rubber modified plastics |
| US3951932A (en) * | 1974-06-17 | 1976-04-20 | Standard Oil Company | Process for preparing olefinic nitrile-vinyl aromatic resins |
| GB2017121B (en) * | 1978-03-27 | 1982-08-18 | Labofina Sa | Process for preparing styrenic resins |
-
1980
- 1980-03-27 US US06/134,472 patent/US4247668A/en not_active Expired - Lifetime
-
1981
- 1981-03-25 JP JP4260481A patent/JPS56159208A/ja active Granted
- 1981-03-25 IT IT20708/81A patent/IT1136948B/it active
- 1981-03-25 FR FR8105933A patent/FR2479238A1/fr active Granted
- 1981-03-26 GB GB8109446A patent/GB2072687B/en not_active Expired
- 1981-03-26 BE BE0/204258A patent/BE888123A/fr not_active IP Right Cessation
- 1981-03-27 DE DE19813112250 patent/DE3112250A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56159208A (en) | 1981-12-08 |
| FR2479238B3 (OSRAM) | 1983-12-09 |
| GB2072687A (en) | 1981-10-07 |
| DE3112250A1 (de) | 1982-04-01 |
| JPS644524B2 (OSRAM) | 1989-01-26 |
| BE888123A (fr) | 1981-07-16 |
| US4247668A (en) | 1981-01-27 |
| IT8120708A0 (it) | 1981-03-25 |
| GB2072687B (en) | 1983-12-07 |
| IT1136948B (it) | 1986-09-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |