DE2157231C3 - Verfahren zur Herstellung von Mischpolymerharzen - Google Patents
Verfahren zur Herstellung von MischpolymerharzenInfo
- Publication number
- DE2157231C3 DE2157231C3 DE2157231A DE2157231A DE2157231C3 DE 2157231 C3 DE2157231 C3 DE 2157231C3 DE 2157231 A DE2157231 A DE 2157231A DE 2157231 A DE2157231 A DE 2157231A DE 2157231 C3 DE2157231 C3 DE 2157231C3
- Authority
- DE
- Germany
- Prior art keywords
- resins
- toluene
- catalyst
- percent
- isobutene
- 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
- 238000000034 method Methods 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 229920005989 resin Polymers 0.000 title description 25
- 239000011347 resin Substances 0.000 title description 25
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 24
- 239000003054 catalyst Substances 0.000 claims description 24
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 229920006026 co-polymeric resin Polymers 0.000 claims description 4
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 3
- 238000010538 cationic polymerization reaction Methods 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- 239000000178 monomer Substances 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 239000012943 hotmelt Substances 0.000 description 4
- 239000012188 paraffin wax Substances 0.000 description 4
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 4
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000004840 adhesive resin Substances 0.000 description 3
- 229920006223 adhesive resin Polymers 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 150000003097 polyterpenes Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000004831 Hot glue Substances 0.000 description 2
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- -1 aliphatic olefins Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000008096 xylene Substances 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
- C08F212/00—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
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Adhesives Or Adhesive Processes (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2157231A DE2157231C3 (de) | 1971-11-18 | 1971-11-18 | Verfahren zur Herstellung von Mischpolymerharzen |
| CA155,760A CA1001797A (en) | 1971-11-18 | 1972-11-03 | .alpha.-METHYLSTYRENE/STYRENE/ISOBUTENETERPOLYMER RESINS AND PROCESS FOR THEIR MANUFACTURE |
| JP47111311A JPS4880689A (enExample) | 1971-11-18 | 1972-11-08 | |
| NL7215343A NL7215343A (enExample) | 1971-11-18 | 1972-11-13 | |
| US00305668A US3814738A (en) | 1971-11-18 | 1972-11-13 | Methylstyrene/styrene/isobutene terpolymer resins and process for their manufacture |
| GB5300272A GB1378977A (en) | 1971-11-18 | 1972-11-16 | Terpolymers |
| IT31745/72A IT970942B (it) | 1971-11-18 | 1972-11-16 | Resine terpolimere di alfa metil stirene stirene isobutene e proce dimento per la loro preparazione |
| FR7241096A FR2160664B1 (enExample) | 1971-11-18 | 1972-11-20 | |
| BE791633D BE791633A (fr) | 1971-11-18 | 1972-11-20 | Resines de polymeres ternaires d'alpha -methylstyrene, de styrene et d'isobutene, et leur fabrication |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2157231A DE2157231C3 (de) | 1971-11-18 | 1971-11-18 | Verfahren zur Herstellung von Mischpolymerharzen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2157231A1 DE2157231A1 (de) | 1973-05-24 |
| DE2157231B2 DE2157231B2 (de) | 1975-10-16 |
| DE2157231C3 true DE2157231C3 (de) | 1978-08-31 |
Family
ID=5825462
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2157231A Expired DE2157231C3 (de) | 1971-11-18 | 1971-11-18 | Verfahren zur Herstellung von Mischpolymerharzen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3814738A (enExample) |
| JP (1) | JPS4880689A (enExample) |
| BE (1) | BE791633A (enExample) |
| CA (1) | CA1001797A (enExample) |
| DE (1) | DE2157231C3 (enExample) |
| FR (1) | FR2160664B1 (enExample) |
| GB (1) | GB1378977A (enExample) |
| IT (1) | IT970942B (enExample) |
| NL (1) | NL7215343A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE17009T1 (de) * | 1981-07-02 | 1986-01-15 | Hercules Inc | Terpolymerharze. |
| JPS6142514A (ja) * | 1984-08-03 | 1986-03-01 | Idemitsu Petrochem Co Ltd | オレフイン−スチレン共重合体の製造方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1155959A (fr) * | 1956-07-10 | 1958-05-12 | Exxon Research Engineering Co | Revêtements de surface pour appareils dessiccateurs de polymères |
-
1971
- 1971-11-18 DE DE2157231A patent/DE2157231C3/de not_active Expired
-
1972
- 1972-11-03 CA CA155,760A patent/CA1001797A/en not_active Expired
- 1972-11-08 JP JP47111311A patent/JPS4880689A/ja active Pending
- 1972-11-13 NL NL7215343A patent/NL7215343A/xx unknown
- 1972-11-13 US US00305668A patent/US3814738A/en not_active Expired - Lifetime
- 1972-11-16 IT IT31745/72A patent/IT970942B/it active
- 1972-11-16 GB GB5300272A patent/GB1378977A/en not_active Expired
- 1972-11-20 FR FR7241096A patent/FR2160664B1/fr not_active Expired
- 1972-11-20 BE BE791633D patent/BE791633A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT970942B (it) | 1974-04-20 |
| GB1378977A (en) | 1975-01-02 |
| DE2157231B2 (de) | 1975-10-16 |
| DE2157231A1 (de) | 1973-05-24 |
| JPS4880689A (enExample) | 1973-10-29 |
| FR2160664B1 (enExample) | 1976-08-20 |
| US3814738A (en) | 1974-06-04 |
| CA1001797A (en) | 1976-12-14 |
| BE791633A (fr) | 1973-05-21 |
| FR2160664A1 (enExample) | 1973-06-29 |
| NL7215343A (enExample) | 1973-05-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| EHJ | Ceased/non-payment of the annual fee |