GB724796A - Heat bodying polydiolefinic drying oils with cyclodiolefins - Google Patents
Heat bodying polydiolefinic drying oils with cyclodiolefinsInfo
- Publication number
- GB724796A GB724796A GB3853/53A GB385353A GB724796A GB 724796 A GB724796 A GB 724796A GB 3853/53 A GB3853/53 A GB 3853/53A GB 385353 A GB385353 A GB 385353A GB 724796 A GB724796 A GB 724796A
- Authority
- GB
- United Kingdom
- Prior art keywords
- drying oils
- reaction
- parts
- improved
- sodium
- 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
- 238000001035 drying Methods 0.000 title abstract 6
- 239000003921 oil Substances 0.000 title abstract 6
- 239000003054 catalyst Substances 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- -1 naphtha Substances 0.000 abstract 3
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 abstract 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract 2
- 150000001993 dienes Chemical class 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 abstract 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 abstract 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical class CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 229910000528 Na alloy Inorganic materials 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 239000001273 butane Substances 0.000 abstract 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000007334 copolymerization reaction Methods 0.000 abstract 1
- 210000003298 dental enamel Anatomy 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000000539 dimer Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000003701 inert diluent Substances 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 abstract 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 1
- 125000005609 naphthenate group Chemical group 0.000 abstract 1
- 125000005474 octanoate group Chemical group 0.000 abstract 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 235000015096 spirit Nutrition 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 abstract 1
- 239000002966 varnish Substances 0.000 abstract 1
- 238000009736 wetting Methods 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Improved drying oils are obtained by heating at 200 DEG to 300 DEG C for 1 to 3 hours, 100 parts of a drying oil derived from a conjugated diolefin having from 4 to 6 carbon atoms, preferably dissolved in an inert hydrocarbon boiling between 80 DEG and 250 DEG C., with 5 to 40 parts of a cyclodiolefin such as cyclopentadiene or methyl cyclopentadiene or their dimers. The wetting properties of the products may be improved by reaction with up to 2.5 per cent by weight of maleic anhydride before or after the reaction with the cyclodiolefin. Diolefins specified for preparing the drying oil are butadiene-1,3; isoprene; 2,3-dimethyl butadiene-1,3; piperylene and methyl pentadiene-1,3; and from 0 to 40 parts of styrene may also be included. The drying oils may be prepared by continuous or batch polymerization in an inert diluent such as naphtha, mineral spirits, butane, xylene, benzene, toluene, cyclohexane, or mixtures, or a modifying diluent, e.g. butene-2, which results in limited copolymerization and chain termination. Other diluents listed are vinyl ethyl, vinyl isobutyl, diethyl and diisopropyl ethers, dioxane, anisole and phenetole. Finely dispersed sodium is used as catalyst, preferably in conjunction with 1 to 50 per cent of a C1 to C5 aliphatic alcohol such as isopropanol or t-butanol. Alternative catalysts are potassium, sodium hydride, sodium alloys and Alfin-type catalysts. Acetic acid is used at the end of the reaction to destroy residual catalyst and the solution of the product is neutralized, filtered, preferably fractionally distilled and then concentrated to an intrinsic viscosity of 0.1 to 0.4. The viscosity may be further increased by heat bodying and naphthenate or octoate driers may be added. The improved drying oils may be used in varnishes and enamels to give films of increased chemical resistance and flexibility.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1075408XA | 1952-05-01 | 1952-05-01 | |
| US724796XA | 1952-05-01 | 1952-05-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB724796A true GB724796A (en) | 1955-02-23 |
Family
ID=33032509
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3853/53A Expired GB724796A (en) | 1952-05-01 | 1953-02-11 | Heat bodying polydiolefinic drying oils with cyclodiolefins |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR1075408A (en) |
| GB (1) | GB724796A (en) |
-
1953
- 1953-02-11 GB GB3853/53A patent/GB724796A/en not_active Expired
- 1953-02-24 FR FR1075408D patent/FR1075408A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1075408A (en) | 1954-10-15 |
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