WO1992009667A1 - Aqueous autoxidatively drying alkyd composition - Google Patents
Aqueous autoxidatively drying alkyd composition Download PDFInfo
- Publication number
- WO1992009667A1 WO1992009667A1 PCT/SE1991/000765 SE9100765W WO9209667A1 WO 1992009667 A1 WO1992009667 A1 WO 1992009667A1 SE 9100765 W SE9100765 W SE 9100765W WO 9209667 A1 WO9209667 A1 WO 9209667A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyd
- alkyd composition
- alkoxylate
- emulsifier
- aqueous
- Prior art date
Links
- 229920000180 alkyd Polymers 0.000 title claims abstract description 48
- 239000000203 mixture Substances 0.000 title claims abstract description 20
- 238000001035 drying Methods 0.000 title claims abstract description 16
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000005529 alkyleneoxy group Chemical group 0.000 claims abstract 2
- 239000000839 emulsion Substances 0.000 claims description 16
- 150000004665 fatty acids Chemical class 0.000 claims description 16
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 15
- 229930195729 fatty acid Natural products 0.000 claims description 15
- 239000000194 fatty acid Substances 0.000 claims description 15
- 239000004530 micro-emulsion Substances 0.000 claims description 9
- 239000003921 oil Substances 0.000 claims description 9
- 235000019198 oils Nutrition 0.000 claims description 9
- 239000000944 linseed oil Substances 0.000 claims description 8
- 235000021388 linseed oil Nutrition 0.000 claims description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 5
- 244000068988 Glycine max Species 0.000 claims description 3
- 235000010469 Glycine max Nutrition 0.000 claims description 3
- 239000003784 tall oil Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 9
- 239000000126 substance Substances 0.000 abstract description 3
- 239000003973 paint Substances 0.000 description 17
- 239000011230 binding agent Substances 0.000 description 7
- 239000004922 lacquer Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000007046 ethoxylation reaction Methods 0.000 description 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- DTRGDWOPRCXRET-SUTYWZMXSA-N (9e,11e,13e)-4-oxooctadeca-9,11,13-trienoic acid Chemical compound CCCC\C=C\C=C\C=C\CCCCC(=O)CCC(O)=O DTRGDWOPRCXRET-SUTYWZMXSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000007605 air drying Methods 0.000 description 2
- -1 alkyl phenol Chemical compound 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000010422 painting Methods 0.000 description 2
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- SBHCLVQMTBWHCD-METXMMQOSA-N (2e,4e,6e,8e,10e)-icosa-2,4,6,8,10-pentaenoic acid Chemical compound CCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C(O)=O SBHCLVQMTBWHCD-METXMMQOSA-N 0.000 description 1
- DTRGDWOPRCXRET-UHFFFAOYSA-N (9Z,11E,13E)-4-Oxo-9,11,13-octadecatrienoic acid Natural products CCCCC=CC=CC=CCCCCC(=O)CCC(O)=O DTRGDWOPRCXRET-UHFFFAOYSA-N 0.000 description 1
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 1
- ODCMOZLVFHHLMY-UHFFFAOYSA-N 1-(2-hydroxyethoxy)hexan-2-ol Chemical compound CCCCC(O)COCCO ODCMOZLVFHHLMY-UHFFFAOYSA-N 0.000 description 1
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-UHFFFAOYSA-N 9,12-Octadecadienoic Acid Chemical compound CCCCCC=CCC=CCCCCCCCC(O)=O OYHQOLUKZRVURQ-UHFFFAOYSA-N 0.000 description 1
- YEBDWAHEIMUJQT-XVSDJDOKSA-N CCCCCC=CCC=CCC=CCC=CCCCC(O)=O.CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O Chemical compound CCCCCC=CCC=CCC=CCC=CCCCC(O)=O.CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YEBDWAHEIMUJQT-XVSDJDOKSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- HXWJFEZDFPRLBG-UHFFFAOYSA-N Timnodonic acid Natural products CCCC=CC=CCC=CCC=CCC=CCCCC(O)=O HXWJFEZDFPRLBG-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000010420 art technique Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000001427 coherent effect Effects 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 239000012971 dimethylpiperazine Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 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 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- 229960004232 linoleic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- UQKAOOAFEFCDGT-UHFFFAOYSA-N n,n-dimethyloctan-1-amine Chemical compound CCCCCCCCN(C)C UQKAOOAFEFCDGT-UHFFFAOYSA-N 0.000 description 1
- ONTCPNMXIFJGRE-UHFFFAOYSA-N octadeca-9,11,13-trienoic acid Chemical compound CCCCC=CC=CC=CCCCCCCCC(O)=O.CCCCC=CC=CC=CCCCCCCCC(O)=O ONTCPNMXIFJGRE-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229940075065 polyvinyl acetate Drugs 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- RJSZFSOFYVMDIC-UHFFFAOYSA-N tert-butyl n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC(C)(C)C RJSZFSOFYVMDIC-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- DTOSIQBPPRVQHS-UHFFFAOYSA-N α-Linolenic acid Chemical compound CCC=CCC=CCC=CCCCCCCCC(O)=O DTOSIQBPPRVQHS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/22—Amides or hydrazides
Definitions
- the present invention relates to an autoxidatively drying alkyd composition containing an emulsifier in the form of a curing alkoxylate of a monoethanolamide.
- Alkyds have long been used as binders in paints and lacquers, and are employed in both professional and hobby painting, as well as in industrial lacquering. They may be the only binder used, as in air-drying paints, or be com- bined with e.g. amino resins, as is common in many stove- curing systems.
- Alkyds are produced by condensation of a polybasic acid, a polyfunctional alcohol and a fatty acid.
- the poly- functional components form the coherent polymer skeleton, and the fatty-acid residues settle as tails on the skele ⁇ ton.
- Polyunsaturated fatty acids yield autoxidatively cur ⁇ ing, i.e. air-drying, binders, whereas saturated and only slightly unsaturated fatty acids yield alkyds for stove- curing. Even today, alkyds constitute the binder that is most commonly used in paints and lacquers.
- the alkyd is first produced in con- ventional manner, and is then emulsified in water.
- This requires the presence of a surface-active agent, usually in a content of 0.5-4% by weight of the finished paint.
- the surface- ctive agent acts as emulsifier, i.e. it con ⁇ tributes to the formation of droplets of the disperse phase and-it stabilises the structure by forming, on the droplets, an elastic surface film which reduces the ten- dency towards coalescence.
- alkyd emulsions of long storage life can be obtained.
- HLB value Hydrophilic Lipophilic Balance
- the use of alkyds in emulsion systems eliminates the hazard of hydrocarbon emission from paints, but at the same time creates other inconveniences for the user.
- the emulsifier acts as an external plasticiser in the film of paint. Being surface-active and low-molecular, the emulsifier migrates to the air-paint film of the inter ⁇ face,- where it accumulates. As a result, the film becomes softer and its water and chemical resistance is impaired compared with a conventional white-spirit-base paint based on the same alkyd as the binder. Also, the presence of a surface-active agent tends to impair the clarity and gloss of the film, as well as its drying qualities.
- microemulsions constitute an alternative to emulsions when alkyds are to be intro ⁇ quizzed in a water-base system.
- Microemulsions differ from emulsions by being thermodynamically stable, i.e. having no tendency to separate when stored, which is a major advantage.
- the production of a microemulsion requires a much larger amount of surface-active agent than does the production of an emulsion.
- the present invention relates to a method for produc ⁇ ing aqueous emulsions and microemulsions of autoxidatively curing alkyds resulting in better film properties than has been the case with the prior-art techniques.
- the invention is based on the idea that the emulsifier employed is an alkoxylate of monoalkanolamide of drying carboxylic acids, i.e. compounds of the general formula:
- R is a polyunsaturated alkyl group having 7-23 carbon atoms, preferably 9-21 carbon atoms
- X is an alky ⁇ leneoxy group derived from an alkylene oxide having 2-3 carbon atoms
- m is 2-4, preferably 2, and n is 2-30, pre- ferably 3-20.
- the emulsifier usually amounts to 0.5-25% by weight of the prepared alkyd composition. If the alkyd composition is an emulsion, the amount of emulsifier pre ⁇ ferably is 1-5% by weight, whereas, if the alkyd composi ⁇ tion is a microemulsion, the amount of emulsifier prefer- ably is 5-20% by weight.
- suitable carboxylic acids wherein R has the meaning stated above, mention may be made of dried fatty acids, such as C-18 fatty acids containing two double bonds, e.g. 9,12-octadecadienoic acid (lino- leic acid) and 9,11-octadecadienoic acid (dehydrated ricinoleic acid), and C-18 fatty acids containing three double bonds, e.g. 9,12,15-octadecatrienoic acid (lino ⁇ lenic acid), 9,11,13-octadecatrienoic acid (eleostearic acid) and 4-keto-9,11,13-octadecatrienoic acid (licanic acid).
- dried fatty acids such as C-18 fatty acids containing two double bonds, e.g. 9,12-octadecadienoic acid (lino- leic acid) and 9,11-octadecadienoic acid (dehydrated ricinoleic acid), and C-18
- polyunsaturated fatty acids such as 5,8,11,14-eicosatetraenoic acid (arachidonic acid) and 5,8,11,14,17-eicosapentaenoic acid
- Suitable natural triglycerides include linseed oil, soya bean oil, tall oil, wood oil, sunflower oil and " fish oil. Dehydrated castor oil is another triglyceride that may conveniently be used.
- the alkoxylate is produced e.g. by aminolysis of the corresponding triglyceride or methyl ester with a suitable 2-amino alkanol, followed by alkoxylation of the obtained amide in the presence of an alkaline catalyst at a tempe ⁇ rature of 150-180°C.
- Alkoxylation is preferably carried out in the presence of a tertiary amine lacking protons that react with alkylene oxide, or an alkylene-oxide- quaternised derivative of. the tertiary amine at a tempe ⁇ rature ranging from room temperature to 120°C, in which case high yields of the desired product can be obtained.
- Suitable tertiary amines include trimethylamine, triethyl ⁇ amine, tributylamine, dimethyloctylamine, tetramethylethy- lenediamine, dimethyl coconut amine, tristearyl amine, dimethyl piperazine and diazabicyclooctane.
- Alkoxylation may comprise ethoxylation, propoxylation, accumulation of propylene oxide and ethylene oxide in blocks, simultaneous addition of ethylene oxide and propylene oxide or a combi- nation thereof.
- the ethylene oxide conveniently amounts to at least 50 mole % of the added alkylene oxide. To use only ethoxylation is preferred.
- Alkoxylation is carried out in such a manner that the emulsifier is given a suitable HLB value, usually 8-15.
- HLB value usually 8-15.
- a normal fraction containing polyunsaturated C-18 acids e.g. derived from linseed oil
- this corre ⁇ sponds when only ethoxylation is used, to an addition of 3-18 moles of ethylene oxide per mole fatty acid mono- ethanolamine.
- the obtained ethoxylate always is a homologous mixture, since the alkoxylation, like most anionic polymerisation processes, results in a statistical distribution as to the degree of polymerisation.
- the alkoxylate according to the invention undergoes autoxidative curing according to the same method as autoxidatively drying alkyds.
- the emulsifier according to the invention may also be combined with other surface-active agents or solubilisers, e.g. to improve the stability of the alkyd composition. Curing can be facili ⁇ tated by certain metal salts, in particular cobalt and manganese salts, so-called driers. Drier-containing emul- sions of drying alkyds with emulsifiers in the form of alkoxylates of the type described herein, result in a film which, when fully cured, does not contain any or only a slight amount of free alkoxylate.
- the autoxidatively curing alkoxylate is bonded in the network formed by the cured binder. Since no alkoxylate, or only a slight amount thereof, is present in the film, the latter has excellent properties as to e.g. hardness, gloss, clarity, water and chemical resistance. The drying properties are also pro ⁇ moted in that the alkoxylate participates in the curing process.
- the invention will be further elucidated by the fol ⁇ lowing Examples.
- Example 1 - Pigment paint based on an alkyd emulsion A glossy paint based on 53% by weight of an alkyd emulsion with a dry content of 60% and containing 20% by weight of titanium dioxide, was formulated with different emulsifiers in an amount of 3%. Stable emulsions with a drop size of about 2 ⁇ m were obtained throughout after high-pressure homogenisation. The alkyd had an oil length of 61% and was based on soya bean oil. The effect of the different emulsifiers on the film properties were esta ⁇ blished as to drying time, gloss, hardness and water resistance. The results are apparent from the Table below. The properties are graded on a scale from 10 (the best) to 1 (the worst). Table 1
- Example 2 Non-pigment lacquer based on an alkyd emulsion
- a non-pigment lacquer based on 59.5 % by weight of an alkyd emulsion with a dry content of 60% was formulated with different emulsifiers in an amount of 2.5%.
- Emulsions of excellent stability and with a drop size of 1-2 ⁇ m were obtained throughout after ultrasound homogenisation.
- the alkyd had an oil length of 66% and was based on tall oil fatty acid.
- the effect of the different emulsifiers on the film properties were established as to drying time, cla ⁇ rity, hardness and water resistance. The results are appa ⁇ rent from the Table below, where the properties are graded on a scale from 10 (the best) to 1 (the worst).
- Table 2 Table 2
- Example 3 Non-pigment lacquer based on a microemulsion of an alkyd
- a microemulsion of an alkyd having an oil length of 64% and based on linseed oil was formulated as follows: 40% by weight of alkyd, 15% by weight of emulsifier, 10% by weight of butyl diethylene glycol, 5% by weight of tri- ethanolamine, the balance being additives and water. Dif ⁇ ferent emulsifiers were tested, and their effect on the film properties was established as to drying time, clari ⁇ ty, hardness and water resistance. The results are appa- rent from the Table below, where the properties are graded on a scale from 10 (the best) to 1 (the worst).
- the autoxidatively curing alkoxylates result in superior film properties, such as drying time and water resistance, compared with the con ⁇ ventional emulsifiers.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Paints Or Removers (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE69112431T DE69112431T2 (en) | 1990-11-23 | 1991-11-12 | AQUEOUS AUTOXIDATIVE DRYING ALKYD COMPOSITION. |
EP91920639A EP0593487B1 (en) | 1990-11-23 | 1991-11-12 | Aqueous autoxidatively drying alkyd composition |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE9003731-8 | 1990-11-23 | ||
SE9003731A SE467543B (en) | 1990-11-23 | 1990-11-23 | Aqueous AUTOXIDATIVE DRYING ALKYD COMPOSITION |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1992009667A1 true WO1992009667A1 (en) | 1992-06-11 |
Family
ID=20380988
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/SE1991/000765 WO1992009667A1 (en) | 1990-11-23 | 1991-11-12 | Aqueous autoxidatively drying alkyd composition |
Country Status (8)
Country | Link |
---|---|
US (1) | US5391649A (en) |
EP (1) | EP0593487B1 (en) |
AT (1) | ATE126820T1 (en) |
DE (1) | DE69112431T2 (en) |
DK (1) | DK0593487T3 (en) |
ES (1) | ES2075965T3 (en) |
SE (1) | SE467543B (en) |
WO (1) | WO1992009667A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000075243A1 (en) * | 1999-06-08 | 2000-12-14 | Imperial Chemical Industries Plc | Emulsions |
US6572972B2 (en) | 2001-06-15 | 2003-06-03 | Solutia Austria Gmbh | Aqueous binders |
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US20040109853A1 (en) * | 2002-09-09 | 2004-06-10 | Reactive Surfaces, Ltd. | Biological active coating components, coatings, and coated surfaces |
US20100233146A1 (en) * | 2002-09-09 | 2010-09-16 | Reactive Surfaces, Ltd. | Coatings and Surface Treatments Having Active Enzymes and Peptides |
US20110070376A1 (en) * | 2002-09-09 | 2011-03-24 | Reactive Surfaces, Ltd. | Anti-fouling Paints & Coatings |
US20090238811A1 (en) * | 2002-09-09 | 2009-09-24 | Mcdaniel C Steven | Enzymatic Antimicrobial and Antifouling Coatings and Polymeric Materials |
US20100210745A1 (en) * | 2002-09-09 | 2010-08-19 | Reactive Surfaces, Ltd. | Molecular Healing of Polymeric Materials, Coatings, Plastics, Elastomers, Composites, Laminates, Adhesives, and Sealants by Active Enzymes |
US20110065856A1 (en) * | 2008-05-13 | 2011-03-17 | Anchor Michael J | Reactive surfactants for waterborne resins |
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JP6391665B2 (en) * | 2013-03-15 | 2018-09-19 | エトクス ケミカルズ リミテッド ライアビリティ カンパニー | Aqueous alkyd resin emulsion containing a fast and reactive emulsifying surfactant |
EP2871195A1 (en) | 2013-11-07 | 2015-05-13 | ALLNEX AUSTRIA GmbH | Cationic Alkyd Resins |
BR102014008480B1 (en) | 2014-04-08 | 2021-06-01 | Oxiteno S.A Indústria E Comércio | RESIN EMULSION COMPOSITION, USE AND PROCESS FOR OBTAINING IT |
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CH531894A (en) * | 1969-03-29 | 1972-12-31 | Hoechst Ag | Mixing emulsifiers for the production of oil-in-water emulsions |
EP0000087A1 (en) * | 1977-06-13 | 1978-12-20 | Unilever N.V. | Aqueous air-drying alkyd dispersions and their use |
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US3979346A (en) * | 1973-11-08 | 1976-09-07 | Vianova-Kunstharz A.G. | Emulsifiers for preparing aqueous dispersions of alkyd resins |
JPS61114728A (en) * | 1984-11-09 | 1986-06-02 | Nippon Oil & Fats Co Ltd | Emulsifier |
-
1990
- 1990-11-23 SE SE9003731A patent/SE467543B/en not_active IP Right Cessation
-
1991
- 1991-11-12 WO PCT/SE1991/000765 patent/WO1992009667A1/en active IP Right Grant
- 1991-11-12 AT AT91920639T patent/ATE126820T1/en not_active IP Right Cessation
- 1991-11-12 EP EP91920639A patent/EP0593487B1/en not_active Expired - Lifetime
- 1991-11-12 ES ES91920639T patent/ES2075965T3/en not_active Expired - Lifetime
- 1991-11-12 DK DK91920639.1T patent/DK0593487T3/en active
- 1991-11-12 DE DE69112431T patent/DE69112431T2/en not_active Expired - Fee Related
-
1993
- 1993-05-21 US US08/066,030 patent/US5391649A/en not_active Expired - Lifetime
Patent Citations (2)
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CH531894A (en) * | 1969-03-29 | 1972-12-31 | Hoechst Ag | Mixing emulsifiers for the production of oil-in-water emulsions |
EP0000087A1 (en) * | 1977-06-13 | 1978-12-20 | Unilever N.V. | Aqueous air-drying alkyd dispersions and their use |
Non-Patent Citations (1)
Title |
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Dialog Information Services, File 351, World Patent Index 81-90, Dialog Accession No. 86-180449/28, (NIPPON OILS & FATS KK), "Emulsifier for several combinations of oil and water contg. ethylene oxide addn. prod. of monoalkanol amine of oleic acid"; & JP,A,61 114 728, 860602, 8628 (Basic). * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000075243A1 (en) * | 1999-06-08 | 2000-12-14 | Imperial Chemical Industries Plc | Emulsions |
US6613817B2 (en) | 1999-06-08 | 2003-09-02 | Imperial Chemical Industries Plc | Emulsions |
US6572972B2 (en) | 2001-06-15 | 2003-06-03 | Solutia Austria Gmbh | Aqueous binders |
Also Published As
Publication number | Publication date |
---|---|
US5391649A (en) | 1995-02-21 |
DK0593487T3 (en) | 1996-01-15 |
ATE126820T1 (en) | 1995-09-15 |
EP0593487B1 (en) | 1995-08-23 |
ES2075965T3 (en) | 1995-10-16 |
SE467543B (en) | 1992-08-03 |
DE69112431D1 (en) | 1995-09-28 |
DE69112431T2 (en) | 1996-02-01 |
EP0593487A1 (en) | 1994-04-27 |
SE9003731D0 (en) | 1990-11-23 |
SE9003731L (en) | 1992-05-24 |
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