JPH11506141A - ビニル芳香族モノマーの重合を防止するための処理 - Google Patents
ビニル芳香族モノマーの重合を防止するための処理Info
- Publication number
- JPH11506141A JPH11506141A JP8536465A JP53646596A JPH11506141A JP H11506141 A JPH11506141 A JP H11506141A JP 8536465 A JP8536465 A JP 8536465A JP 53646596 A JP53646596 A JP 53646596A JP H11506141 A JPH11506141 A JP H11506141A
- Authority
- JP
- Japan
- Prior art keywords
- vinyl aromatic
- dinitrosalicylic acid
- polymerization
- composition
- derivative
- 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
- 239000000178 monomer Substances 0.000 title claims abstract description 42
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 37
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 34
- 239000000203 mixture Substances 0.000 claims abstract description 38
- WDMUXYQIMRDWRC-UHFFFAOYSA-N 2-hydroxy-3,4-dinitrobenzoic acid Chemical class OC(=O)C1=CC=C([N+]([O-])=O)C([N+]([O-])=O)=C1O WDMUXYQIMRDWRC-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 18
- LWFUFLREGJMOIZ-UHFFFAOYSA-N 3,5-dinitrosalicylic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O LWFUFLREGJMOIZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- GBPNAALUHSMCQE-UHFFFAOYSA-N 3-[hydroxy(3-hydroxypropyl)amino]propan-1-ol Chemical compound OCCCN(O)CCCO GBPNAALUHSMCQE-UHFFFAOYSA-N 0.000 claims abstract description 5
- UMELTKSLWXJXNZ-UHFFFAOYSA-N methyl 3,5-dinitrosalicylate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O UMELTKSLWXJXNZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 44
- -1 hydroxylamine compound Chemical class 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 15
- 229910052760 oxygen Inorganic materials 0.000 description 15
- 239000001301 oxygen Substances 0.000 description 15
- 239000003112 inhibitor Substances 0.000 description 9
- 238000004821 distillation Methods 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- HOYRZHJJAHRMLL-UHFFFAOYSA-N 2,6-dinitro-p-cresol Chemical compound CC1=CC([N+]([O-])=O)=C(O)C([N+]([O-])=O)=C1 HOYRZHJJAHRMLL-UHFFFAOYSA-N 0.000 description 2
- 229920001174 Diethylhydroxylamine Polymers 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- QHJIRTVISXHLRI-UHFFFAOYSA-N 6-methyl-4,6-dinitrocyclohexa-1,3-dien-1-ol Chemical compound [O-][N+](=O)C1(C)CC([N+]([O-])=O)=CC=C1O QHJIRTVISXHLRI-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
- C09K15/24—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen containing a phenol or quinone moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/20—Use of additives, e.g. for stabilisation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S585/00—Chemistry of hydrocarbon compounds
- Y10S585/949—Miscellaneous considerations
- Y10S585/95—Prevention or removal of corrosion or solid deposits
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.ジニトロサリチル酸、それの誘導体または異性体およびヒドロキシルアミ ン化合物を含んでなる組成物。 2.ジニトロサリチル酸、それの誘導体または異性体が、式: [式中、R1はH、フェニル、メチル、エチル、n−プロピル、イソプロピル, n−ブチルおよびイソブチルである。] を有することを特徴とする請求項1記載の組成物。 3.ジニトロサリチル酸誘導体が、3,5−ジニトロサリチル酸および3,5 −ジニトロサリチル酸メチルエステルからなる群から選択されることを特徴とす る請求項1または2に記載の組成物。 4.ヒドロキシルアミン化合物が、式: [式中、R2およびR3は、同じまたは異なり、水素、アルキル、アリール、アル クアリール、アラルキルまたはヒドロキシアルキル基であり、3〜約20個の炭 素原子を有する。] を有することを特徴とする請求項1〜3のいずれかに記載の組成物。 5.ヒドロキシルアミン化合物が、ビス−(ヒドロキシプロピル)ヒドロキシ ルアミンであることを特徴とする請求項1〜4のいずれかに記載の組成物。 6.ジニトロサリチル酸、それの誘導体または異性体とヒドロキシルアミン化 合物が、1:9〜9:1の重量比であることを特徴とする請求項1〜5のいずれ かに記載の組成物。 7.請求項1〜6のいずれかに記載の組成物を、効果的に重合を防止する量で モノマーに添加することを含んでなるビニル芳香族加工系でビニル芳香族モノマ ーの重合を防止する方法。 8.ビニル芳香族モノマーに、該組成物を、ビニル芳香族モノマーに対して1 〜10,000ppmの量で添加することを特徴とする請求項7記載の方法。 9.ビニル芳香族モノマーがスチレンであることを特徴とする請求項7または 8記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/454,999 | 1995-05-31 | ||
US08/454,999 US5648572A (en) | 1995-05-31 | 1995-05-31 | Compositions and methods for inhibiting vinyl aromatic monomer polymerization |
PCT/US1996/005531 WO1996038399A1 (en) | 1995-05-31 | 1996-04-19 | Treatments for inhibiting vinyl aromatic monomer polymerization |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH11506141A true JPH11506141A (ja) | 1999-06-02 |
JP3752255B2 JP3752255B2 (ja) | 2006-03-08 |
Family
ID=23806950
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP53646596A Expired - Fee Related JP3752255B2 (ja) | 1995-05-31 | 1996-04-19 | ビニル芳香族モノマーの重合を防止するための処理 |
Country Status (10)
Country | Link |
---|---|
US (1) | US5648572A (ja) |
EP (1) | EP0840718B1 (ja) |
JP (1) | JP3752255B2 (ja) |
AT (1) | ATE188235T1 (ja) |
AU (1) | AU5562196A (ja) |
BR (1) | BR9608861A (ja) |
CA (1) | CA2215517C (ja) |
DE (1) | DE69605923T2 (ja) |
ES (1) | ES2140844T3 (ja) |
WO (1) | WO1996038399A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014037376A (ja) * | 2012-08-16 | 2014-02-27 | Katayama Chem Works Co Ltd | ビニル芳香族モノマーの重合を抑制するための組成物 |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2764882B1 (fr) * | 1997-06-23 | 1999-09-03 | Rhodia Chimie Sa | Composition et procede d'inhibition de la polymerisation radicalaire de monomeres aromatiques a insaturation ethylenique |
US6685823B2 (en) * | 2000-10-16 | 2004-02-03 | Uniroyal Chemical Company, Inc. | C-nitrosoaniline compounds and their blends as polymerization inhibitors |
US6761833B2 (en) | 2001-03-20 | 2004-07-13 | Atofina Chemicals, Inc. | Stabilization of monomers by compositions based on alkylhydroxylamines |
US7128826B2 (en) * | 2003-07-31 | 2006-10-31 | General Electric Company | Polymerization inhibitor for styrene dehydrogenation units |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2388041A (en) * | 1941-07-26 | 1945-10-30 | Goodrich Co B F | Process for the extraction of butadiene |
US4105506A (en) * | 1977-02-24 | 1978-08-08 | Cosden Technology, Inc. | Polymerization inhibitor for vinyl aromatic compounds |
US4439278A (en) * | 1982-06-21 | 1984-03-27 | Eastman Kodak Company | Process inhibitor for readily polymerizable ethylenically unsaturated aromatic compounds |
US4389285A (en) * | 1982-06-21 | 1983-06-21 | Eastman Kodak Company | Process inhibitor for readily polymerizable ethylenically unsaturated aromatic compounds |
US4409408A (en) * | 1982-09-24 | 1983-10-11 | Atlantic Richfield Company | Inhibiting polymerization of vinyl aromatic monomers |
US4466905A (en) * | 1983-04-11 | 1984-08-21 | Cosden Technology, Inc. | Polymerization inhibition process for vinyl aromatic compounds |
EP0240297A1 (en) * | 1986-04-01 | 1987-10-07 | Betz Europe, Inc. | Inhibiting polymerization of vinyl aromatic compounds |
US4720566A (en) * | 1986-10-23 | 1988-01-19 | Betz Laboratories, Inc. | Method and composition for inhibiting acrylonitrile polymerization |
US4774374A (en) * | 1987-06-12 | 1988-09-27 | Uniroyal Chemical Company, Inc. | Stabilized vinyl aromatic composition |
-
1995
- 1995-05-31 US US08/454,999 patent/US5648572A/en not_active Expired - Lifetime
-
1996
- 1996-04-19 AU AU55621/96A patent/AU5562196A/en not_active Abandoned
- 1996-04-19 BR BR9608861A patent/BR9608861A/pt not_active IP Right Cessation
- 1996-04-19 DE DE69605923T patent/DE69605923T2/de not_active Expired - Lifetime
- 1996-04-19 EP EP96912980A patent/EP0840718B1/en not_active Expired - Lifetime
- 1996-04-19 CA CA002215517A patent/CA2215517C/en not_active Expired - Lifetime
- 1996-04-19 AT AT96912980T patent/ATE188235T1/de not_active IP Right Cessation
- 1996-04-19 WO PCT/US1996/005531 patent/WO1996038399A1/en active IP Right Grant
- 1996-04-19 JP JP53646596A patent/JP3752255B2/ja not_active Expired - Fee Related
- 1996-04-19 ES ES96912980T patent/ES2140844T3/es not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014037376A (ja) * | 2012-08-16 | 2014-02-27 | Katayama Chem Works Co Ltd | ビニル芳香族モノマーの重合を抑制するための組成物 |
Also Published As
Publication number | Publication date |
---|---|
WO1996038399A1 (en) | 1996-12-05 |
US5648572A (en) | 1997-07-15 |
DE69605923D1 (de) | 2000-02-03 |
CA2215517A1 (en) | 1996-12-05 |
ES2140844T3 (es) | 2000-03-01 |
EP0840718A4 (en) | 1998-08-12 |
DE69605923T2 (de) | 2000-07-13 |
EP0840718B1 (en) | 1999-12-29 |
JP3752255B2 (ja) | 2006-03-08 |
BR9608861A (pt) | 1999-06-15 |
AU5562196A (en) | 1996-12-18 |
EP0840718A1 (en) | 1998-05-13 |
ATE188235T1 (de) | 2000-01-15 |
CA2215517C (en) | 2008-07-08 |
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