JPS5984908A - ｐ−ビニルフエノ−ル重合体の製造方法 - Google Patents
ｐ−ビニルフエノ−ル重合体の製造方法Info
- Publication number
- JPS5984908A JPS5984908A JP57194449A JP19444982A JPS5984908A JP S5984908 A JPS5984908 A JP S5984908A JP 57194449 A JP57194449 A JP 57194449A JP 19444982 A JP19444982 A JP 19444982A JP S5984908 A JPS5984908 A JP S5984908A
- Authority
- JP
- Japan
- Prior art keywords
- vinylphenol
- polymer
- low
- iron
- weight
- 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
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 title claims abstract description 146
- 229920000642 polymer Polymers 0.000 title claims abstract description 55
- 238000004519 manufacturing process Methods 0.000 title claims description 17
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 50
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 29
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229910052742 iron Inorganic materials 0.000 claims abstract description 22
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 19
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 claims description 17
- 239000006227 byproduct Substances 0.000 abstract description 37
- 238000006243 chemical reaction Methods 0.000 abstract description 18
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 239000007791 liquid phase Substances 0.000 abstract description 4
- 239000003607 modifier Substances 0.000 abstract description 3
- 150000007522 mineralic acids Chemical class 0.000 abstract description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 16
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 150000002989 phenols Chemical class 0.000 description 12
- 230000000694 effects Effects 0.000 description 9
- 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 7
- 229930003836 cresol Natural products 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 150000002506 iron compounds Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- -1 iron ions Chemical class 0.000 description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
- 229940106681 chloroacetic acid Drugs 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- VEPSWGHMGZQCIN-UHFFFAOYSA-H ferric oxalate Chemical compound [Fe+3].[Fe+3].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O VEPSWGHMGZQCIN-UHFFFAOYSA-H 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- PVFSDGKDKFSOTB-UHFFFAOYSA-K iron(3+);triacetate Chemical compound [Fe+3].CC([O-])=O.CC([O-])=O.CC([O-])=O PVFSDGKDKFSOTB-UHFFFAOYSA-K 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- FQIWSDCHZJPMII-UHFFFAOYSA-N (1-hydroxy-2-phenylethyl) acetate Chemical compound CC(=O)OC(O)CC1=CC=CC=C1 FQIWSDCHZJPMII-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- YNGIFMKMDRDNBQ-UHFFFAOYSA-N 3-ethenylphenol Chemical compound OC1=CC=CC(C=C)=C1 YNGIFMKMDRDNBQ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 241000269821 Scombridae Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000000911 decarboxylating effect Effects 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000020640 mackerel Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 231100000989 no adverse effect Toxicity 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical class CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 210000004894 snout Anatomy 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 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
- C08F12/00—Homopolymers and 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
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
- C08F12/22—Oxygen
- C08F12/24—Phenols or alcohols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Emergency Medicine (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Polymerization Catalysts (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57194449A JPS5984908A (ja) | 1982-11-04 | 1982-11-04 | ｐ−ビニルフエノ−ル重合体の製造方法 |
| CA000439761A CA1211894A (en) | 1982-11-04 | 1983-10-26 | Process for the production of p-vinyl phenol polymer |
| US06/548,255 US4517349A (en) | 1982-11-04 | 1983-11-02 | Process for the production of p-vinyl phenol polymer |
| DE198383306717T DE108624T1 (de) | 1982-11-04 | 1983-11-04 | Verfahren zur herstellung von p-vinylphenolpolymer. |
| DE8383306717T DE3362204D1 (en) | 1982-11-04 | 1983-11-04 | Process for the production of p-vinyl phenol polymer |
| EP83306717A EP0108624B1 (en) | 1982-11-04 | 1983-11-04 | Process for the production of p-vinyl phenol polymer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57194449A JPS5984908A (ja) | 1982-11-04 | 1982-11-04 | ｐ−ビニルフエノ−ル重合体の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5984908A true JPS5984908A (ja) | 1984-05-16 |
| JPS612683B2 JPS612683B2 (OSRAM) | 1986-01-27 |
Family
ID=16324752
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57194449A Granted JPS5984908A (ja) | 1982-11-04 | 1982-11-04 | ｐ−ビニルフエノ−ル重合体の製造方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4517349A (OSRAM) |
| EP (1) | EP0108624B1 (OSRAM) |
| JP (1) | JPS5984908A (OSRAM) |
| CA (1) | CA1211894A (OSRAM) |
| DE (2) | DE3362204D1 (OSRAM) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2566179B1 (fr) * | 1984-06-14 | 1986-08-22 | Commissariat Energie Atomique | Procede d'autopositionnement d'un oxyde de champ localise par rapport a une tranchee d'isolement |
| FR2570844B1 (fr) * | 1984-09-21 | 1986-11-14 | Commissariat Energie Atomique | Film photosensible a base de polymere silicie et son utilisation comme resine de masquage dans un procede de lithographie |
| US5210137A (en) * | 1990-11-19 | 1993-05-11 | Shell Oil Company | Polyketone polymer blends |
| US5200460A (en) * | 1991-04-30 | 1993-04-06 | Shell Oil Company | Polyacetal polymer blends |
| US5432249A (en) * | 1993-12-22 | 1995-07-11 | Nippon Oil Company, Limited | Liquid crystalline polyesters |
| US5448002A (en) * | 1994-08-12 | 1995-09-05 | The Goodyear Tire & Rubber Company | Synthesis of trans-1,4-polybutadiene having controlled molecular weight |
| US5463141A (en) * | 1994-12-19 | 1995-10-31 | Hoechst Clanese Corporation | Process for preparing poly(4-hydroxystyrene) |
| US6218485B1 (en) | 1995-09-19 | 2001-04-17 | Nippon Soda Co., Ltd. | Process for producing narrow polydispersity alkenylphenol polymer |
| JPH10251315A (ja) * | 1997-03-11 | 1998-09-22 | Maruzen Petrochem Co Ltd | ビニルフェノール系重合体の製造方法及び安定化されたビニルフェノール系重合原料組成物 |
| US5959051A (en) * | 1997-03-11 | 1999-09-28 | Maruzen Petrochemical Co., Ltd. | Process for preparing vinylphenol polymers and stabilized compositions of vinylphenol-containing polymerization raw material |
| KR20010040758A (ko) * | 1998-02-09 | 2001-05-15 | 우메하라 이와오 | 담색 ｐ-비닐페놀계 중합체의 제조방법 |
| DE10014381C1 (de) * | 2000-03-23 | 2001-05-31 | Siemens Ag | Sensorsystem zur Bestimmung der Insassenposition in Fahrzeugen |
| WO2005113634A1 (en) | 2004-05-05 | 2005-12-01 | Dupont Electronic Polymers L.P. | Derivatized polyhydroxystyrenes with a novolak type structure and processes for preparing the same |
| CN101558090B (zh) | 2006-08-01 | 2011-08-31 | 杜邦电子聚合物有限合伙公司 | 由酚类材料制备聚合物的方法及与之相关的组合物 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1013243A (en) * | 1963-08-24 | 1965-12-15 | Distillers Co Yeast Ltd | Process for making polychloroprene |
| US3842019A (en) * | 1969-04-04 | 1974-10-15 | Minnesota Mining & Mfg | Use of sulfonic acid salts in cationic polymerization |
| IT990992B (it) * | 1973-07-06 | 1975-07-10 | Sir Soc Italiana Resine Spa | Procedimento per la preparazione di poliacrilonitrile e di copoli meri dell acrilonitrile |
| US4376839A (en) * | 1980-01-21 | 1983-03-15 | Technicon Instruments Corporation | Heat stable, polymer-forming composition |
| US4413108A (en) * | 1980-11-03 | 1983-11-01 | Minnesota Mining & Manufacturing Company | Anaerobically-curing compositions |
-
1982
- 1982-11-04 JP JP57194449A patent/JPS5984908A/ja active Granted
-
1983
- 1983-10-26 CA CA000439761A patent/CA1211894A/en not_active Expired
- 1983-11-02 US US06/548,255 patent/US4517349A/en not_active Expired - Lifetime
- 1983-11-04 EP EP83306717A patent/EP0108624B1/en not_active Expired
- 1983-11-04 DE DE8383306717T patent/DE3362204D1/de not_active Expired
- 1983-11-04 DE DE198383306717T patent/DE108624T1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS612683B2 (OSRAM) | 1986-01-27 |
| US4517349A (en) | 1985-05-14 |
| CA1211894A (en) | 1986-09-23 |
| EP0108624B1 (en) | 1986-02-19 |
| DE3362204D1 (en) | 1986-03-27 |
| DE108624T1 (de) | 1985-01-31 |
| EP0108624A1 (en) | 1984-05-16 |
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