GB1139137A - Improved drying oils containing polyalkylene oxide and/or polyurethane groups - Google Patents
Improved drying oils containing polyalkylene oxide and/or polyurethane groupsInfo
- Publication number
- GB1139137A GB1139137A GB689866A GB689866A GB1139137A GB 1139137 A GB1139137 A GB 1139137A GB 689866 A GB689866 A GB 689866A GB 689866 A GB689866 A GB 689866A GB 1139137 A GB1139137 A GB 1139137A
- Authority
- GB
- United Kingdom
- Prior art keywords
- groups
- generally
- oils
- same
- drying
- 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
- 239000003921 oil Substances 0.000 title abstract 10
- 238000001035 drying Methods 0.000 title abstract 6
- 229920000233 poly(alkylene oxides) Polymers 0.000 title abstract 3
- 239000004814 polyurethane Substances 0.000 title abstract 2
- 229920002635 polyurethane Polymers 0.000 title abstract 2
- 239000003054 catalyst Substances 0.000 abstract 4
- 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
- 125000003700 epoxy group Chemical group 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- 229920001228 polyisocyanate Polymers 0.000 abstract 3
- 239000005056 polyisocyanate Substances 0.000 abstract 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 abstract 2
- 239000012948 isocyanate Substances 0.000 abstract 2
- 150000002513 isocyanates Chemical class 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 125000000466 oxiranyl group Chemical group 0.000 abstract 2
- 229920001515 polyalkylene glycol Polymers 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 244000068988 Glycine max Species 0.000 abstract 1
- 235000010469 Glycine max Nutrition 0.000 abstract 1
- 244000020551 Helianthus annuus Species 0.000 abstract 1
- 235000003222 Helianthus annuus Nutrition 0.000 abstract 1
- 240000006240 Linum usitatissimum Species 0.000 abstract 1
- 235000004431 Linum usitatissimum Nutrition 0.000 abstract 1
- 235000010678 Paulownia tomentosa Nutrition 0.000 abstract 1
- 240000002834 Paulownia tomentosa Species 0.000 abstract 1
- 235000004443 Ricinus communis Nutrition 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 239000007822 coupling agent Substances 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 229940013317 fish oils Drugs 0.000 abstract 1
- 235000004426 flaxseed Nutrition 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical class O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- -1 hydroxyl compound Chemical class 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 239000012285 osmium tetroxide Substances 0.000 abstract 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000012286 potassium permanganate Substances 0.000 abstract 1
- 239000003784 tall oil Substances 0.000 abstract 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-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
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/36—Hydroxylated esters of higher fatty acids
-
- 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
- C08G18/48—Polyethers
- C08G18/4891—Polyethers modified with higher fatty oils or their acids or by resin acids
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
-
- 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)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Polyurethanes Or Polyureas (AREA)
- Epoxy Resins (AREA)
- Lubricants (AREA)
- Polyethers (AREA)
- Paints Or Removers (AREA)
Abstract
1,139,137. Polyalkylene oxides and polyurethanes; epoxidized drying oils. UNILEVER Ltd. 16 Feb., 1966 [17 Feb., 1965; 16 Dec., 1965; 12 Jan., 1966; 13 Jan., 1966; 31 Jan., 1966], No. 6898/66. Headings C3B and C3R. The invention comprises semi-drying and drying oils, characterized that on average not more than 1À5 ethylenic double bonds in the oil molecule have been oxidized and converted into a group where P and Q represent the same or different groups -(OR) n T, excluding the case where P and Q are both OH, R is the same or different C 2-3 alkylene group, n is zero in at least one of the groups P and Q and otherwise an integer, the average value of which varies between 3 and 400, T represents the same or different groups: where V is OH when n is an integer or the group: excluding the possibility that V is -OH when n is zero, A is the same or different hydrocarbon radical derived from an organic polyisocyanate, r is 1 or 2 and n<SP>1</SP> may be the same or different from n but satisfies the same conditions. They may be obtained by oxidizing not more than 1À5 ethylenic double bonds in each oil molecule and reacting the product thus obtained with a polyalkylene glycol and/or a polyisocyanate in this or in the reversed sequence. The oxidation of the oil (i.e. conversion of the ethylenic double bonds into oxirane groups or into vicinal hydroxyl groups with which the organic isocyanate may react) may be effected (a) by reacting the oil with a " per " acid, which may be formed in situ (e.g. from hydrogen peroxide and a caroxylic acid), generally in the presence of a catalyst below 100‹ C. and the oxirane groups may subsequently be hydrolysed to vicinal hydroxy groups, e.g. with water, generally by heating in the presence of an acid catalyst, or (b) with mild oxidation agents, e.g. H 2 O 2 , generally with a catalyst such as osmium tetroxide or vanadium pentoxide, or potassium permanganate, generally below 100‹ C. The conversion of the epoxy groups into polyalkylene oxide groups with polyalkylene glycols, which generally have an average molecular weight of 200 to 20,000 and which are generally employed in quantities exceeding 0À5 mols. per epoxy group, preferably 1 to 2 mols. per epoxy group, may be effected between 20‹ and 130‹ C., preferably in the presence of a catalyst. The reaction of the hydroxyl compound, which generally contains not more than two hydroxyl groups in the molecule, with isocyanates is generally effected at between 50‹ and 200‹ C. and conventional catalysts may be employed. The oils may be semi-drying and drying natural and mineral (synthetic) oils and fatty acid condensation products, specified natural oils being linseed, dehydrated castor, tung, citicica, soyabean, sunflower and fish oils and tall oil esters. Specified polyisocyanates are toluene, triphenylmethane and hexamethylene diisocyanates. Driers and coupling agents may be added to the products.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEU0011450 | 1965-02-17 | ||
| DEU0012283 | 1965-12-16 | ||
| DEU0012361 | 1966-01-12 | ||
| DEU0012366 | 1966-01-13 | ||
| DEU0012409 | 1966-01-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1139137A true GB1139137A (en) | 1969-01-08 |
Family
ID=27512323
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB689866A Expired GB1139137A (en) | 1965-02-17 | 1966-02-16 | Improved drying oils containing polyalkylene oxide and/or polyurethane groups |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT292872B (en) |
| CH (1) | CH475330A (en) |
| DE (5) | DE1645539C3 (en) |
| GB (1) | GB1139137A (en) |
| NL (1) | NL6602029A (en) |
| SE (1) | SE333422B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6433125B1 (en) | 1995-09-08 | 2002-08-13 | Henkel Kommanditgesellschaft Auf Aktien | Fatty chemical polyalcohols as reagent thinners |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3317194A1 (en) * | 1983-05-11 | 1984-11-15 | Henkel KGaA, 4000 Düsseldorf | POLYURETHANE PREPOLYMERS BASED ON OLEOCHEMICAL POLYOLS, THEIR PRODUCTION AND USE |
| DE3347045A1 (en) * | 1983-12-24 | 1985-07-04 | Henkel KGaA, 4000 Düsseldorf | TWO COMPONENT POLYURETHANE ADHESIVE |
| DE3630422A1 (en) * | 1986-09-06 | 1988-03-10 | Henkel Kgaa | USE OF FAT POLYOLS FOR THE PRODUCTION OF AQUEOUS POLYURETHANE DISPERSIONS |
| EP0437592A1 (en) * | 1989-08-09 | 1991-07-24 | Battelle-Institut e.V. | Process for preparing plastics from raw fats and oils |
| DE4308097A1 (en) * | 1993-03-15 | 1994-09-22 | Henkel Kgaa | Polyol for an isocyanate casting resin and coatings |
| DE19646424A1 (en) | 1996-11-11 | 1998-05-14 | Henkel Kgaa | Use of polyols for isocyanate casting resins and coating compositions |
-
1965
- 1965-02-17 DE DE19651645539 patent/DE1645539C3/en not_active Expired
- 1965-12-16 DE DE19651645564 patent/DE1645564A1/en active Pending
-
1966
- 1966-01-12 DE DE19661645570 patent/DE1645570A1/en active Pending
- 1966-01-13 DE DE19661645571 patent/DE1645571A1/en active Pending
- 1966-01-31 DE DE19661645573 patent/DE1645573A1/en active Pending
- 1966-02-16 GB GB689866A patent/GB1139137A/en not_active Expired
- 1966-02-17 SE SE207266A patent/SE333422B/xx unknown
- 1966-02-17 CH CH227766A patent/CH475330A/en not_active IP Right Cessation
- 1966-02-17 AT AT144966A patent/AT292872B/en active
- 1966-02-17 NL NL6602029A patent/NL6602029A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6433125B1 (en) | 1995-09-08 | 2002-08-13 | Henkel Kommanditgesellschaft Auf Aktien | Fatty chemical polyalcohols as reagent thinners |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1645564A1 (en) | 1970-08-06 |
| DE1645571A1 (en) | 1970-07-09 |
| DE1645539B2 (en) | 1973-03-22 |
| DE1645539A1 (en) | 1970-09-17 |
| DE1645539C3 (en) | 1973-10-25 |
| AT292872B (en) | 1971-09-10 |
| NL6602029A (en) | 1966-08-18 |
| SE333422B (en) | 1971-03-15 |
| DE1645570A1 (en) | 1970-09-24 |
| CH475330A (en) | 1969-07-15 |
| DE1645573A1 (en) | 1971-01-21 |
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