GB1040037A - Process for the cationic co-oligomerization of conjugated-unsaturated fatty acids or their esters with indene and/or coumarone - Google Patents
Process for the cationic co-oligomerization of conjugated-unsaturated fatty acids or their esters with indene and/or coumaroneInfo
- Publication number
- GB1040037A GB1040037A GB7460/65A GB746065A GB1040037A GB 1040037 A GB1040037 A GB 1040037A GB 7460/65 A GB7460/65 A GB 7460/65A GB 746065 A GB746065 A GB 746065A GB 1040037 A GB1040037 A GB 1040037A
- Authority
- GB
- United Kingdom
- Prior art keywords
- coumarone
- indene
- methyl ester
- acid methyl
- fatty acid
- 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
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 title abstract 8
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 title abstract 8
- 125000002091 cationic group Chemical group 0.000 title abstract 2
- 150000002148 esters Chemical class 0.000 title abstract 2
- 238000000034 method Methods 0.000 title 1
- 238000006384 oligomerization reaction Methods 0.000 title 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 abstract 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 239000003112 inhibitor Substances 0.000 abstract 2
- 239000003921 oil Substances 0.000 abstract 2
- 235000019198 oils Nutrition 0.000 abstract 2
- BJEMXPVDXFSROA-UHFFFAOYSA-N 3-butylbenzene-1,2-diol Chemical compound CCCCC1=CC=CC(O)=C1O BJEMXPVDXFSROA-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- 235000019485 Safflower oil Nutrition 0.000 abstract 1
- 235000019486 Sunflower oil Nutrition 0.000 abstract 1
- 238000004061 bleaching Methods 0.000 abstract 1
- 239000011280 coal tar Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 229920001971 elastomer Polymers 0.000 abstract 1
- 239000006260 foam Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004033 plastic Substances 0.000 abstract 1
- 229920003023 plastic Polymers 0.000 abstract 1
- 229920001228 polyisocyanate Polymers 0.000 abstract 1
- 239000005056 polyisocyanate Substances 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000005060 rubber Substances 0.000 abstract 1
- 235000005713 safflower oil Nutrition 0.000 abstract 1
- 239000003813 safflower oil Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 235000012424 soybean oil Nutrition 0.000 abstract 1
- 239000002600 sunflower oil Substances 0.000 abstract 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 abstract 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
-
- 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
- C08F244/00—Coumarone-indene copolymers
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
- C08G18/423—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing cycloaliphatic groups
- C08G18/4233—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing cycloaliphatic groups derived from polymerised higher fatty acids 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/123—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/137—Acids or hydroxy compounds containing cycloaliphatic rings
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F7/00—Chemical modification of drying oils
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Conjugated unsaturated fatty acids and/or their esters are reacted with indene and/or coumarone in a ratio of 0.5 to 20 mols. of indene and/or coumarone per mol. of the acid component, in the presence of acid or Friedel-Crafts catalysts and phenolic polymerization inhibitor to a constant viscosity to form cationic cooligomers. Isomerized monoesters of semi-drying oils, e.g. soya oil fatty acid methyl ester, sunflower oil fatty acid methyl ester, and safflower oil fatty acid methyl ester may be used with hydrocarbon mixtures such as coal tar oil fractions or solvent naphtha which contain the indene and/or coumarone. Activated bleaching earth may be the catalyst and hydroquinone and butyl catechol the inhibitors. The products are suitable for the preparation of coatings, plastics and with polyisocyanates to form rubbers or foams.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEH0053613 | 1964-08-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1040037A true GB1040037A (en) | 1966-08-24 |
Family
ID=7158402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7460/65A Expired GB1040037A (en) | 1964-08-22 | 1965-02-22 | Process for the cationic co-oligomerization of conjugated-unsaturated fatty acids or their esters with indene and/or coumarone |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3441577A (en) |
| AT (1) | AT250941B (en) |
| BE (1) | BE660017A (en) |
| CH (1) | CH438275A (en) |
| GB (1) | GB1040037A (en) |
| NL (2) | NL6502656A (en) |
| SE (1) | SE325022B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL8103066A (en) * | 1981-06-25 | 1983-01-17 | Unilever Nv | PROCESS FOR TRIMERIZING UNSATURATED FATTY ACIDS. |
| CN105693930A (en) * | 2014-11-25 | 2016-06-22 | 上海宝钢化工有限公司 | Carboxyl coumarone resin and preparation method thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1007914B (en) * | 1953-03-30 | 1957-05-09 | Gelsenkirchener Bergwerks Ag | Process for the production of paint binders |
| FR1235546A (en) * | 1959-05-29 | 1960-07-08 | Centre Nat Rech Scient | Process for the preparation of high polymers from indene or similar compounds and products obtained |
| NL122982C (en) * | 1962-04-25 | 1900-01-01 |
-
0
- NL NL123922D patent/NL123922C/xx active
-
1965
- 1965-01-21 CH CH84365A patent/CH438275A/en unknown
- 1965-02-08 AT AT109465A patent/AT250941B/en active
- 1965-02-16 SE SE1951/65A patent/SE325022B/xx unknown
- 1965-02-19 BE BE660017D patent/BE660017A/xx unknown
- 1965-02-22 GB GB7460/65A patent/GB1040037A/en not_active Expired
- 1965-03-03 NL NL6502656A patent/NL6502656A/xx unknown
- 1965-03-22 US US441874A patent/US3441577A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NL6502656A (en) | 1966-02-23 |
| SE325022B (en) | 1970-06-22 |
| AT250941B (en) | 1966-12-12 |
| NL123922C (en) | |
| BE660017A (en) | 1965-06-16 |
| US3441577A (en) | 1969-04-29 |
| CH438275A (en) | 1967-06-30 |
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