GB477954A - A process for the manufacture of resinous condensation products - Google Patents
A process for the manufacture of resinous condensation productsInfo
- Publication number
- GB477954A GB477954A GB18744/36A GB1874436A GB477954A GB 477954 A GB477954 A GB 477954A GB 18744/36 A GB18744/36 A GB 18744/36A GB 1874436 A GB1874436 A GB 1874436A GB 477954 A GB477954 A GB 477954A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oil
- phenol
- halides
- terpine
- sesquiterpenes
- 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 abstract 3
- 239000007859 condensation product Substances 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 abstract 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 3
- 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 abstract 3
- 239000003921 oil Substances 0.000 abstract 3
- 235000019198 oils Nutrition 0.000 abstract 3
- 150000002989 phenols Chemical class 0.000 abstract 3
- 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 abstract 3
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 abstract 2
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 abstract 2
- 244000304337 Cuminum cyminum Species 0.000 abstract 2
- 235000007129 Cuminum cyminum Nutrition 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 abstract 2
- JMFRWRFFLBVWSI-NSCUHMNNSA-N coniferol Chemical compound COC1=CC(\C=C\CO)=CC=C1O JMFRWRFFLBVWSI-NSCUHMNNSA-N 0.000 abstract 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 239000010665 pine oil Substances 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- -1 terpene halides Chemical class 0.000 abstract 2
- 235000007586 terpenes Nutrition 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 abstract 1
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 abstract 1
- NFLGAXVYCFJBMK-RKDXNWHRSA-N (+)-isomenthone Natural products CC(C)[C@H]1CC[C@@H](C)CC1=O NFLGAXVYCFJBMK-RKDXNWHRSA-N 0.000 abstract 1
- NZGWDASTMWDZIW-MRVPVSSYSA-N (+)-pulegone Chemical compound C[C@@H]1CCC(=C(C)C)C(=O)C1 NZGWDASTMWDZIW-MRVPVSSYSA-N 0.000 abstract 1
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 abstract 1
- 239000001306 (7E,9E,11E,13E)-pentadeca-7,9,11,13-tetraen-1-ol Substances 0.000 abstract 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 abstract 1
- 239000005973 Carvone Substances 0.000 abstract 1
- 241000723346 Cinnamomum camphora Species 0.000 abstract 1
- 241000218631 Coniferophyta Species 0.000 abstract 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 abstract 1
- WEEGYLXZBRQIMU-UHFFFAOYSA-N Eucalyptol Chemical compound C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 abstract 1
- NFLGAXVYCFJBMK-UHFFFAOYSA-N Menthone Chemical compound CC(C)C1CCC(C)CC1=O NFLGAXVYCFJBMK-UHFFFAOYSA-N 0.000 abstract 1
- NZGWDASTMWDZIW-UHFFFAOYSA-N Pulegone Natural products CC1CCC(=C(C)C)C(=O)C1 NZGWDASTMWDZIW-UHFFFAOYSA-N 0.000 abstract 1
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 abstract 1
- USMNOWBWPHYOEA-UHFFFAOYSA-N alpha-thujone Natural products CC1C(=O)CC2(C(C)C)C1C2 USMNOWBWPHYOEA-UHFFFAOYSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 abstract 1
- 229940116229 borneol Drugs 0.000 abstract 1
- 229930008380 camphor Natural products 0.000 abstract 1
- 229960000846 camphor Drugs 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000001862 carum carvi l. seed oil Substances 0.000 abstract 1
- IRAQOCYXUMOFCW-CXTNEJHOSA-N cedrene Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@H]1C(C)=CC2 IRAQOCYXUMOFCW-CXTNEJHOSA-N 0.000 abstract 1
- SVURIXNDRWRAFU-OGMFBOKVSA-N cedrol Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@@H]1[C@@](O)(C)CC2 SVURIXNDRWRAFU-OGMFBOKVSA-N 0.000 abstract 1
- 229940026455 cedrol Drugs 0.000 abstract 1
- PCROEXHGMUJCDB-UHFFFAOYSA-N cedrol Natural products CC1CCC2C(C)(C)C3CC(C)(O)CC12C3 PCROEXHGMUJCDB-UHFFFAOYSA-N 0.000 abstract 1
- 229930007050 cineol Natural products 0.000 abstract 1
- 229960005233 cineole Drugs 0.000 abstract 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 229940119526 coniferyl alcohol Drugs 0.000 abstract 1
- 150000001896 cresols Chemical class 0.000 abstract 1
- 239000001941 cymbopogon citratus dc and cymbopogon flexuosus oil Substances 0.000 abstract 1
- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 abstract 1
- IRAQOCYXUMOFCW-UHFFFAOYSA-N di-epi-alpha-cedrene Natural products C1C23C(C)CCC3C(C)(C)C1C(C)=CC2 IRAQOCYXUMOFCW-UHFFFAOYSA-N 0.000 abstract 1
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- SVURIXNDRWRAFU-UHFFFAOYSA-N juniperanol Natural products C1C23C(C)CCC3C(C)(C)C1C(O)(C)CC2 SVURIXNDRWRAFU-UHFFFAOYSA-N 0.000 abstract 1
- 229940041616 menthol Drugs 0.000 abstract 1
- 229930007503 menthone Natural products 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 150000004780 naphthols Chemical class 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- CKMXAIVXVKGGFM-UHFFFAOYSA-N p-cumic acid Chemical compound CC(C)C1=CC=C(C(O)=O)C=C1 CKMXAIVXVKGGFM-UHFFFAOYSA-N 0.000 abstract 1
- 229930007459 p-menth-8-en-3-one Natural products 0.000 abstract 1
- 150000003097 polyterpenes Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 229930004725 sesquiterpene Natural products 0.000 abstract 1
- 150000004354 sesquiterpene derivatives Chemical class 0.000 abstract 1
- USDOQCCMRDNVAH-UHFFFAOYSA-N sigma-cadinene Natural products C1C=C(C)CC2C(C(C)C)CC=C(C)C21 USDOQCCMRDNVAH-UHFFFAOYSA-N 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- 150000003505 terpenes Chemical class 0.000 abstract 1
- 229940116411 terpineol Drugs 0.000 abstract 1
- 150000003509 tertiary alcohols Chemical class 0.000 abstract 1
- 239000002023 wood Substances 0.000 abstract 1
- 150000003739 xylenols Chemical class 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
- USDOQCCMRDNVAH-KKUMJFAQSA-N β-cadinene Chemical compound C1C=C(C)C[C@H]2[C@H](C(C)C)CC=C(C)[C@@H]21 USDOQCCMRDNVAH-KKUMJFAQSA-N 0.000 abstract 1
Classifications
-
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/28—Chemically modified polycondensates
-
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/28—Chemically modified polycondensates
- C08G8/30—Chemically modified polycondensates by unsaturated compounds, e.g. terpenes
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
In the process of producing resinous condensation products p from substituted phenols and aldehydes according to the parent Specification there are used in addition to or in place of the terpene halides used therein as starting materials halides prepared from saturated, unsaturated or hydroxy sesquiterpenes or polyterpenes or derivatives thereof or oxygen containing terpenes (that is compounds having ten carbon atoms in the molecule, six of which are bound together as a ring). The halides are prepared by addition of halogen or hydrogen halide, by substitution with halogen or by esterification or by any combination of such methods. Suitable terpine-like starting materials include cedrene, cadinene, cedrol, santalol, abietic acid, coniferyl alcohol, menthol, terpine, terpineol, borneol, cineol, menthone, pulegone, carvone, conifer oils, pine oils, cumin oil, caraway seed oil, oil of camphor, lemon grass oil, bergamot oil, gum rosin, wood rosin or rosin esters. Suitable phenols include phenol, cresols, xylenols, naphthols, polyoxybenzenes or crude mixtures containing them. In examples, American pine oil (consisting mainly of tertiary alcohols and sesquiterpenes) cumin or abietic acid is treated with hydrochloric acid, condensed with phenol in the presence of zinc chloride and then condensed with aldehyde, the excess phenol being removed or converted into a substituted phenol before the condensation.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US477954XA | 1935-07-06 | 1935-07-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB477954A true GB477954A (en) | 1938-01-06 |
Family
ID=21951020
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB18744/36A Expired GB477954A (en) | 1935-07-06 | 1936-07-06 | A process for the manufacture of resinous condensation products |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB477954A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0075771A1 (en) * | 1981-09-25 | 1983-04-06 | Bayer Ag | Phenols, process for their production and their use as stabilizers for polymers |
| WO2010144969A1 (en) * | 2009-06-19 | 2010-12-23 | Eze Board Australia Pty Ltd | Production of perlite and fiber based composite panel board |
-
1936
- 1936-07-06 GB GB18744/36A patent/GB477954A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0075771A1 (en) * | 1981-09-25 | 1983-04-06 | Bayer Ag | Phenols, process for their production and their use as stabilizers for polymers |
| WO2010144969A1 (en) * | 2009-06-19 | 2010-12-23 | Eze Board Australia Pty Ltd | Production of perlite and fiber based composite panel board |
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