DE2148662A1 - Verfahren zur herstellung von betapinen-dipenten-copolymeren - Google Patents
Verfahren zur herstellung von betapinen-dipenten-copolymerenInfo
- Publication number
- DE2148662A1 DE2148662A1 DE19712148662 DE2148662A DE2148662A1 DE 2148662 A1 DE2148662 A1 DE 2148662A1 DE 19712148662 DE19712148662 DE 19712148662 DE 2148662 A DE2148662 A DE 2148662A DE 2148662 A1 DE2148662 A1 DE 2148662A1
- Authority
- DE
- Germany
- Prior art keywords
- monomer
- catalyst
- polymer
- addition
- added
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 40
- 230000008569 process Effects 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 229920001577 copolymer Polymers 0.000 title description 9
- 239000000178 monomer Substances 0.000 claims description 100
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims description 78
- 229920000642 polymer Polymers 0.000 claims description 67
- 239000002904 solvent Substances 0.000 claims description 32
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 claims description 22
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 claims description 21
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 claims description 21
- 229930006722 beta-pinene Natural products 0.000 claims description 21
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 claims description 21
- 150000003097 polyterpenes Chemical class 0.000 claims description 21
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 238000001816 cooling Methods 0.000 claims description 9
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 7
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 3
- 125000003783 beta-pinene group Chemical group 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
- 238000006116 polymerization reaction Methods 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 22
- 235000007586 terpenes Nutrition 0.000 description 14
- 150000003505 terpenes Chemical class 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 12
- 229920001519 homopolymer Polymers 0.000 description 7
- 238000000576 coating method Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000004821 Contact adhesive Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 241000779819 Syncarpia glomulifera Species 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 239000001739 pinus spp. Substances 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- 229940036248 turpentine Drugs 0.000 description 4
- GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 230000004044 response Effects 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
- GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 1
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- PXRCIOIWVGAZEP-UHFFFAOYSA-N Primaeres Camphenhydrat Natural products C1CC2C(O)(C)C(C)(C)C1C2 PXRCIOIWVGAZEP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 229930006739 camphene Natural products 0.000 description 1
- ZYPYEBYNXWUCEA-UHFFFAOYSA-N camphenilone Natural products C1CC2C(=O)C(C)(C)C1C2 ZYPYEBYNXWUCEA-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 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
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15951071A | 1971-07-02 | 1971-07-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2148662A1 true DE2148662A1 (de) | 1973-01-11 |
Family
ID=22572855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712148662 Pending DE2148662A1 (de) | 1971-07-02 | 1971-09-29 | Verfahren zur herstellung von betapinen-dipenten-copolymeren |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3761457A (enExample) |
| JP (1) | JPS4861589A (enExample) |
| BE (1) | BE773176A (enExample) |
| CA (1) | CA980049A (enExample) |
| DE (1) | DE2148662A1 (enExample) |
| FR (1) | FR2145129A5 (enExample) |
| GB (1) | GB1319425A (enExample) |
| NL (1) | NL7113303A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7608676B2 (en) | 2006-11-29 | 2009-10-27 | Ppg Industries Ohio, Inc. | Coatings comprising the reaction product of a terpene, an acrylic monomer and a phenolic compound |
| US7776959B2 (en) | 2006-11-29 | 2010-08-17 | Ppg Industries Ohio, Inc. | Coatings comprising terpene |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4081592A (en) * | 1977-02-17 | 1978-03-28 | The Standard Oil Company | Process of polymerizing acrylonitrile copolymers employing terpinolene or gamma terpinene as a chain modifier |
| US4797460A (en) * | 1987-01-12 | 1989-01-10 | Arizona Chemical Company | Tackifier resin composition and process for preparing same |
| US4879351A (en) * | 1988-08-15 | 1989-11-07 | Arizona Chemical Company | Isomerized terpene tackifier resins |
| US5847247A (en) * | 1994-04-14 | 1998-12-08 | Arizona Chemical Company | Terpene-based solvents |
| JP5461180B2 (ja) * | 2008-04-10 | 2014-04-02 | 株式会社クラレ | β−ピネン系共重合体及びその製造方法 |
| TW200951151A (en) * | 2008-04-10 | 2009-12-16 | Kuraray Co | β-pinene-based polymer and molded product made therefrom |
| JP2012036280A (ja) * | 2010-08-05 | 2012-02-23 | Kuraray Co Ltd | β−ピネン系重合体の製造方法 |
-
1971
- 1971-07-02 US US00159510A patent/US3761457A/en not_active Expired - Lifetime
- 1971-08-04 GB GB3668071A patent/GB1319425A/en not_active Expired
- 1971-08-05 CA CA119,926A patent/CA980049A/en not_active Expired
- 1971-09-28 NL NL7113303A patent/NL7113303A/xx unknown
- 1971-09-28 BE BE773176A patent/BE773176A/xx unknown
- 1971-09-29 FR FR7135074A patent/FR2145129A5/fr not_active Expired
- 1971-09-29 JP JP46076207A patent/JPS4861589A/ja active Pending
- 1971-09-29 DE DE19712148662 patent/DE2148662A1/de active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7608676B2 (en) | 2006-11-29 | 2009-10-27 | Ppg Industries Ohio, Inc. | Coatings comprising the reaction product of a terpene, an acrylic monomer and a phenolic compound |
| US7776959B2 (en) | 2006-11-29 | 2010-08-17 | Ppg Industries Ohio, Inc. | Coatings comprising terpene |
Also Published As
| Publication number | Publication date |
|---|---|
| BE773176A (fr) | 1972-03-28 |
| GB1319425A (en) | 1973-06-06 |
| US3761457A (en) | 1973-09-25 |
| JPS4861589A (enExample) | 1973-08-29 |
| FR2145129A5 (enExample) | 1973-02-16 |
| NL7113303A (enExample) | 1973-01-04 |
| CA980049A (en) | 1975-12-16 |
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