GB573826A - Manufacture of condensation products of lac and compositions made therewith - Google Patents
Manufacture of condensation products of lac and compositions made therewithInfo
- Publication number
- GB573826A GB573826A GB1589643A GB1589643A GB573826A GB 573826 A GB573826 A GB 573826A GB 1589643 A GB1589643 A GB 1589643A GB 1589643 A GB1589643 A GB 1589643A GB 573826 A GB573826 A GB 573826A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oil
- lac
- acid
- product
- fatty acids
- 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
- 239000000203 mixture Substances 0.000 title abstract 7
- 239000007859 condensation product Substances 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 23
- 239000000047 product Substances 0.000 abstract 10
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 7
- 239000000194 fatty acid Substances 0.000 abstract 7
- 229930195729 fatty acid Natural products 0.000 abstract 7
- 150000004665 fatty acids Chemical class 0.000 abstract 7
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 abstract 6
- 239000003921 oil Substances 0.000 abstract 6
- 235000019198 oils Nutrition 0.000 abstract 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 5
- 235000021388 linseed oil Nutrition 0.000 abstract 5
- 239000000944 linseed oil Substances 0.000 abstract 5
- 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 4
- 229920001800 Shellac Polymers 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- 238000007605 air drying Methods 0.000 abstract 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 4
- 239000004208 shellac Substances 0.000 abstract 4
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 abstract 4
- 229940113147 shellac Drugs 0.000 abstract 4
- 235000013874 shellac Nutrition 0.000 abstract 4
- 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 4
- 239000002966 varnish Substances 0.000 abstract 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 abstract 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- 244000068988 Glycine max Species 0.000 abstract 2
- 235000010469 Glycine max Nutrition 0.000 abstract 2
- 244000020551 Helianthus annuus Species 0.000 abstract 2
- 235000003222 Helianthus annuus Nutrition 0.000 abstract 2
- 240000006240 Linum usitatissimum Species 0.000 abstract 2
- 235000004431 Linum usitatissimum Nutrition 0.000 abstract 2
- 235000004347 Perilla Nutrition 0.000 abstract 2
- 244000124853 Perilla frutescens Species 0.000 abstract 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 abstract 2
- 238000001035 drying Methods 0.000 abstract 2
- 230000032050 esterification Effects 0.000 abstract 2
- 238000005886 esterification reaction Methods 0.000 abstract 2
- -1 ethylene, propylene, butylene Chemical group 0.000 abstract 2
- 235000004426 flaxseed Nutrition 0.000 abstract 2
- 239000010491 poppyseed oil Substances 0.000 abstract 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 abstract 1
- 229920000877 Melamine resin Polymers 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 239000001164 aluminium sulphate Substances 0.000 abstract 1
- 238000004061 bleaching Methods 0.000 abstract 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 abstract 1
- 239000000920 calcium hydroxide Substances 0.000 abstract 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 abstract 1
- 235000011116 calcium hydroxide Nutrition 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 239000004359 castor oil Substances 0.000 abstract 1
- 235000019438 castor oil Nutrition 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 229920003086 cellulose ether Polymers 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 150000001896 cresols Chemical class 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 238000006266 etherification reaction Methods 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 235000013305 food Nutrition 0.000 abstract 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 abstract 1
- 150000002334 glycols Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 239000003350 kerosene Substances 0.000 abstract 1
- 239000004922 lacquer Substances 0.000 abstract 1
- HTUMBQDCCIXGCV-UHFFFAOYSA-N lead oxide Chemical compound [O-2].[Pb+2] HTUMBQDCCIXGCV-UHFFFAOYSA-N 0.000 abstract 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N lead(II) oxide Inorganic materials [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 abstract 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- 229910044991 metal oxide Inorganic materials 0.000 abstract 1
- 150000004706 metal oxides Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000003973 paint Substances 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- 239000000057 synthetic resin Substances 0.000 abstract 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 abstract 1
- 239000005028 tinplate Substances 0.000 abstract 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002383 tung 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
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
- 239000011787 zinc oxide 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
- C09F5/00—Obtaining drying-oils
- C09F5/08—Obtaining drying-oils by esterification of fatty 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
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
- C09F1/04—Chemical modification, e.g. esterification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Paints Or Removers (AREA)
Abstract
Lac which has been etherified with one of the hydroxyl groups of a glycol is esterified with a resin acid or with an unsaturated fatty acid containing more than one double bond, but containing no conjugated double bonds. Two or more mixed resin acids or mixed fatty acids or a mixture of a resin acid with one or more fatty acids may be employed. Suitable acids are abietic, e.g. as rosin, or the fatty acids of linseed, sunflower, perilla, soya bean or poppy seed oil. Suitable glycols are ethylene, propylene, butylene or di-, tri- or tetra-ethylene glycol. Etherification may be carried out with excess glycol above the melting point of the lac and, if desired, with an acid condensing agent such as aluminium chloride or sulphate or sulphuric or paratoluene sulphonic acid. Excess glycol and condensing agent may be removed by washing with water or the glycol only may be removed by distillation and the residue with some remaining acid catalyst used for the esterification which may be conducted at 120-300 DEG C. with or without a condensing agent, and if desired in an atmosphere of an inert gas, or in an inert solvent which is preferably an ingredient of the final composition. The lac glycol ether may be polymerized before esterification. Acidity of the products may be reduced by addition of a base, e.g. a metal oxide. The products may be purified by treatment with a bleaching earth or activated carbon in the presence of solvents. The products are soluble in drying oils which may be pre-bodied, or the lac ether-ester and the oil may be bodied together. The ether-esters are compatible with synthetic resins such as formaldehyde condensation products of phenols, cresols, urea or melamine, or with cellulose esters or ethers. They are suitable for paints, varnishes, linoleum, plasticizers, printers' ink, printers' blankets, electrical insulating coatings, or lacquers for tin plate for food containers. According to the examples: (1) the ethylene glycol ether of dewaxed lac is heated with linseed oil fatty acids at 140-150 DEG C. in presence of p-toluene sulphonic acid or at 200 DEG C. with no catalyst. Solutions of the products in organic solvents yield air drying films which may be baked; (2) the butylene glycol ether of T.N. shellac is heated first with linseed oil fatty acids and then with rosin. Litharge is dispersed in the product with heating and stirring and the product, thinned with white spirit yields an air-drying varnish; (3) an ethylene glycol ether of shellac is esterified with fatty acid from linseed, sunflower, perilla, soya bean or poppy seed oil or a mixture of these acids. The product is heated with linseed oil and thinned with white spirit. It yields air-drying films which may be baked. Pale bodied oil, dehydrated castor oil or tung oil may replace the linseed oil, or a bodied oil such as stand oil may be used without the second heating treatment; (4) ethylene glycol ether of orange shellac is heated with rosin and slaked lime or zinc oxide mixed with the product which is soluble in hydrocarbons or drying oils to yield air-drying or stoving media; (5) Dewaxed lac is melted with ethylene glycol, cooled, mixed with a little sulphuric acid, and the mixture distilled. Linseed oil fatty acids are added to the residue and the mixture heated with additional sulphuric acid. The product may be thinned with white spirit to yield a varnish or bodied by further heating in an inert atmosphere; (6) ethylene glycol ether of shellac and rosin are melted together and white spirit added. The product is refluxed, water being separated from the condensed solvent. The resulting varnish may be further diluted with xylene or a xylene-white spirit mixture. Other solvents which may be employed are tetralin, decalin or kerosene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1589643A GB573826A (en) | 1943-09-28 | 1943-09-28 | Manufacture of condensation products of lac and compositions made therewith |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1589643A GB573826A (en) | 1943-09-28 | 1943-09-28 | Manufacture of condensation products of lac and compositions made therewith |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB573826A true GB573826A (en) | 1945-12-07 |
Family
ID=10067495
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1589643A Expired GB573826A (en) | 1943-09-28 | 1943-09-28 | Manufacture of condensation products of lac and compositions made therewith |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB573826A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107216812A (en) * | 2017-07-06 | 2017-09-29 | 中国林业科学研究院林产化学工业研究所 | A kind of method that solid phase reaction prepares rosin lac carboxylate |
-
1943
- 1943-09-28 GB GB1589643A patent/GB573826A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107216812A (en) * | 2017-07-06 | 2017-09-29 | 中国林业科学研究院林产化学工业研究所 | A kind of method that solid phase reaction prepares rosin lac carboxylate |
| CN107216812B (en) * | 2017-07-06 | 2020-11-27 | 中国林业科学研究院林产化学工业研究所 | A kind of method for preparing rosin-shellac ester compound by solid-phase reaction |
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