GB836218A - Improvements in or relating to the manufacture of thixotropic materials - Google Patents
Improvements in or relating to the manufacture of thixotropic materialsInfo
- Publication number
- GB836218A GB836218A GB8357A GB8357A GB836218A GB 836218 A GB836218 A GB 836218A GB 8357 A GB8357 A GB 8357A GB 8357 A GB8357 A GB 8357A GB 836218 A GB836218 A GB 836218A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oil
- product
- reacted
- tert
- ethylene diamine
- 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
- 230000009974 thixotropic effect Effects 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000000047 product Substances 0.000 abstract 15
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 12
- 239000003921 oil Substances 0.000 abstract 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 10
- 235000019198 oils Nutrition 0.000 abstract 10
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 8
- 240000006240 Linum usitatissimum Species 0.000 abstract 6
- 235000004431 Linum usitatissimum Nutrition 0.000 abstract 6
- 150000001412 amines Chemical class 0.000 abstract 6
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 abstract 6
- 235000004426 flaxseed Nutrition 0.000 abstract 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 4
- 125000001931 aliphatic group Chemical group 0.000 abstract 4
- 229920000180 alkyd Polymers 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 229920001577 copolymer Polymers 0.000 abstract 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 abstract 4
- -1 ethylene, tetramethylene, hexamethylene Chemical group 0.000 abstract 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 abstract 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 239000004359 castor oil Substances 0.000 abstract 3
- 235000019438 castor oil Nutrition 0.000 abstract 3
- 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 3
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 abstract 3
- 239000002966 varnish Substances 0.000 abstract 3
- 244000068988 Glycine max Species 0.000 abstract 2
- 235000010469 Glycine max Nutrition 0.000 abstract 2
- 235000004443 Ricinus communis Nutrition 0.000 abstract 2
- 238000001035 drying Methods 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 150000004715 keto acids Chemical class 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 230000004048 modification Effects 0.000 abstract 2
- 238000012986 modification Methods 0.000 abstract 2
- 235000015112 vegetable and seed oil Nutrition 0.000 abstract 2
- 239000008158 vegetable oil Substances 0.000 abstract 2
- 244000061176 Nicotiana tabacum Species 0.000 abstract 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000003240 coconut oil Substances 0.000 abstract 1
- 235000019864 coconut oil Nutrition 0.000 abstract 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 abstract 1
- 235000021388 linseed oil Nutrition 0.000 abstract 1
- 239000000944 linseed oil Substances 0.000 abstract 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000003549 soybean oil Substances 0.000 abstract 1
- 235000012424 soybean oil Nutrition 0.000 abstract 1
- 229920001897 terpolymer Polymers 0.000 abstract 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 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
-
- 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
- C08G63/91—Polymers modified by chemical after-treatment
- C08G63/914—Polymers modified by chemical after-treatment derived from polycarboxylic acids and polyhydroxy compounds
-
- 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
- C08G69/34—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids using polymerised unsaturated fatty acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/08—Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/04—Thixotropic paints
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Graft Or Block Polymers (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polyesters Or Polycarbonates (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Thixotropic products are obtained by heating a vegetable oil, not containing combined ketoacids, which has been partially homopolymerized to give a product of viscosity not less than 5 poises, with 0.5-20% by weight of the oil of hydrazine or an aliphatic diprimary amine containing an even number of carbon atoms. Suitable partially polymerized oils are varnish, dehydrated castor, bodied tobacco seed, soybean, chinawood and linseed stand oils. Hydrazine may be used as the hydrate, and other suitable amines are ethylene, tetramethylene, hexamethylene and decamethylene diamines. In a modification of the process, the oils are not homopolymerized, but copolymerized with styrene, a - methylstyrene, cyclopentadiene, vinyl toluene, methyl methacrylate or acrylonitrile, the product so obtained being treated with an aliphatic diprimary amine containing an even number of carbon atoms as before, but not in this case with hydrazine. If required, the products obtained in either case may be heat blended with alkyd resins.ALSO:Thixotropic products are obtained by heating a vegetable oil, not containing combined ketoacids, which has been partially homopolymerized to give a product of viscosity not less than 5 poises, with 0.5-20% by weight of the oil of hydrazine or an aliphatic diprimary amine containing an even number of carbon atoms. Suitable partially polymerized oils are varnish, dehydrated castor, bodied tobacco-seed, soybean, chinawood and linseed stand oils. Hydrazine may be used as the hydrate, and other suitable amines are ethylene, tetramethylene, hexamethylene and decamethylene diamines. In a modification of the process, the oils are not homopolymerized but are copolymerized with styrene, a -methylstyrene, cyclopentadiene, vinyltoluene, methyl methacrylate or acrylonitrile, the product so obtained being treated with an aliphatic diprimary amine containing an even number of carbon atoms as before, but not in this case with hydrazine. The products obtained in either case may be heat blended with alkyd resins. In examples: (12) dehydrated castor oil and styrene are copolymerized in the presence of lauryl mercaptan and di-tert. butyl peroxide, and the product is reacted with ethylene diamine; (13) a drying oil-cyclopentadiene copolymer is treated with ethylene diamine; (14) a linseed oil-styrene copolymer is treated with hexamethylene diamine; (15) a drying oil-cyclopentadiene copolymer is reacted with hexamethylene diamine; (16) dehydrated castor oil and methyl methacrylate are copolymerized in presence of di-tert. butyl peroxide and the product is reacted with ethylene diamine; (17) varnish linseed oil and acrylonitrile are copolymerized in presence of di-tert. butyl peroxide and the product is reacted with ethylene diamine; (18) the product of (12) is heated in solution with a soybean oil alkyd until homogeneous; (19) the product of (15) is heated until homogeneous with a long-oil linseed/pentaerythritol alkyd; (27) linseed stand oil, a cyclopentadiene-oil copolymer and aqueous ethylene diamine are reacted together; (28) the reaction product obtained by refluxing together a solution in toluene of coconut oil and vinyl toluene in the presence of tert. butyl hydroperoxide is reacted with aqueous ethylene diamine; (29) linseed stand oil and styrene are copolymerized in the presence of di-tert. butyl peroxide and the product is reacted with aqueous ethylene diamine; and (30) a terpolymer obtained by copolymerizing dehydrated castor oil with styrene in the presence of di-tert. butyl peroxide, followed by further polymerization of the product so obtained with methyl methacrylate and di-tert. butyl peroxide, is reacted with aqueous ethylene diamine.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8357A GB836218A (en) | 1957-01-01 | 1957-01-01 | Improvements in or relating to the manufacture of thixotropic materials |
| FR754035A FR1246159A (en) | 1957-01-01 | 1957-12-17 | Process for the production of thixotropic materials usable in paints and varnishes |
| DE19571494406 DE1494406A1 (en) | 1957-01-01 | 1957-12-27 | Thixotropic modified alkyd resins |
| DE1957B0047286 DE1090357B (en) | 1957-01-01 | 1957-12-27 | Process for the production of thixotropic substances |
| GB2952759A GB896895A (en) | 1957-01-01 | 1959-08-28 | Improvements in or relating to the manufacture of thixotropic materials |
| GB2952659A GB903638A (en) | 1957-01-01 | 1959-08-28 | Improvements in or relating to the manufacture of thixotropic materials |
| FR836692A FR78284E (en) | 1957-01-01 | 1960-08-25 | Process for the production of thixotropic materials usable in paints and varnishes |
| FR836801A FR78465E (en) | 1957-01-01 | 1960-08-26 | Process for the production of thixotropic materials usable in paints and varnishes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8357A GB836218A (en) | 1957-01-01 | 1957-01-01 | Improvements in or relating to the manufacture of thixotropic materials |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB836218A true GB836218A (en) | 1960-06-01 |
Family
ID=6971334
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8357A Expired GB836218A (en) | 1957-01-01 | 1957-01-01 | Improvements in or relating to the manufacture of thixotropic materials |
| GB2952659A Expired GB903638A (en) | 1957-01-01 | 1959-08-28 | Improvements in or relating to the manufacture of thixotropic materials |
| GB2952759A Expired GB896895A (en) | 1957-01-01 | 1959-08-28 | Improvements in or relating to the manufacture of thixotropic materials |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2952659A Expired GB903638A (en) | 1957-01-01 | 1959-08-28 | Improvements in or relating to the manufacture of thixotropic materials |
| GB2952759A Expired GB896895A (en) | 1957-01-01 | 1959-08-28 | Improvements in or relating to the manufacture of thixotropic materials |
Country Status (3)
| Country | Link |
|---|---|
| DE (2) | DE1090357B (en) |
| FR (3) | FR1246159A (en) |
| GB (3) | GB836218A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3478807B1 (en) | 2016-06-30 | 2020-04-15 | Green Frix | Lubricating oil |
| EP3478806B1 (en) | 2016-06-30 | 2020-04-15 | Green Frix | Lubricating oil |
| CN114805718A (en) * | 2022-05-18 | 2022-07-29 | 中国林业科学研究院林产化学工业研究所 | Preparation method and application of high-biomass-based polyimide self-repairing polymer |
-
1957
- 1957-01-01 GB GB8357A patent/GB836218A/en not_active Expired
- 1957-12-17 FR FR754035A patent/FR1246159A/en not_active Expired
- 1957-12-27 DE DE1957B0047286 patent/DE1090357B/en active Pending
- 1957-12-27 DE DE19571494406 patent/DE1494406A1/en active Pending
-
1959
- 1959-08-28 GB GB2952659A patent/GB903638A/en not_active Expired
- 1959-08-28 GB GB2952759A patent/GB896895A/en not_active Expired
-
1960
- 1960-08-25 FR FR836692A patent/FR78284E/en not_active Expired
- 1960-08-26 FR FR836801A patent/FR78465E/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3478807B1 (en) | 2016-06-30 | 2020-04-15 | Green Frix | Lubricating oil |
| EP3478806B1 (en) | 2016-06-30 | 2020-04-15 | Green Frix | Lubricating oil |
| CN114805718A (en) * | 2022-05-18 | 2022-07-29 | 中国林业科学研究院林产化学工业研究所 | Preparation method and application of high-biomass-based polyimide self-repairing polymer |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1246159A (en) | 1961-02-03 |
| DE1090357B (en) | 1960-10-06 |
| FR78465E (en) | 1962-07-27 |
| GB903638A (en) | 1962-08-15 |
| FR78284E (en) | 1962-06-29 |
| DE1494406A1 (en) | 1969-08-07 |
| GB896895A (en) | 1962-05-23 |
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