EP1268682A1 - Utilisation de combinaisons d'additifs pour eviter la formation d'une peau sur des peintures sechant a l'air - Google Patents
Utilisation de combinaisons d'additifs pour eviter la formation d'une peau sur des peintures sechant a l'airInfo
- Publication number
- EP1268682A1 EP1268682A1 EP01913821A EP01913821A EP1268682A1 EP 1268682 A1 EP1268682 A1 EP 1268682A1 EP 01913821 A EP01913821 A EP 01913821A EP 01913821 A EP01913821 A EP 01913821A EP 1268682 A1 EP1268682 A1 EP 1268682A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- radical
- skin
- drying
- use according
- compounds
- 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.)
- Withdrawn
Links
- 239000000654 additive Substances 0.000 title claims abstract description 27
- 239000004922 lacquer Substances 0.000 title claims abstract description 23
- 230000000996 additive effect Effects 0.000 title claims abstract description 22
- 230000015572 biosynthetic process Effects 0.000 title abstract description 22
- 238000007605 air drying Methods 0.000 title description 2
- 238000001035 drying Methods 0.000 claims abstract description 40
- 239000000203 mixture Substances 0.000 claims abstract description 38
- -1 aliphatic amines Chemical class 0.000 claims description 22
- 239000003973 paint Substances 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 14
- 150000001450 anions Chemical class 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 239000011230 binding agent Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 150000007942 carboxylates Chemical class 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 239000000976 ink Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- PQLLEAYSRJFMFF-UHFFFAOYSA-N sulfuric acid;hydroiodide Chemical class I.OS(O)(=O)=O PQLLEAYSRJFMFF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004989 dicarbonyl group Chemical group 0.000 abstract description 2
- 150000003139 primary aliphatic amines Chemical class 0.000 abstract description 2
- 150000005619 secondary aliphatic amines Chemical class 0.000 abstract description 2
- 150000003510 tertiary aliphatic amines Chemical class 0.000 abstract description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 21
- 229910052791 calcium Inorganic materials 0.000 description 21
- 239000011575 calcium Substances 0.000 description 21
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 14
- WHIVNJATOVLWBW-PLNGDYQASA-N (nz)-n-butan-2-ylidenehydroxylamine Chemical compound CC\C(C)=N/O WHIVNJATOVLWBW-PLNGDYQASA-N 0.000 description 13
- 239000003921 oil Substances 0.000 description 11
- 238000009472 formulation Methods 0.000 description 10
- 229920000180 alkyd Polymers 0.000 description 9
- 230000002265 prevention Effects 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 239000008199 coating composition Substances 0.000 description 7
- 229910017052 cobalt Inorganic materials 0.000 description 7
- 239000010941 cobalt Substances 0.000 description 7
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- 235000019589 hardness Nutrition 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 4
- 150000002923 oximes Chemical class 0.000 description 4
- 230000002411 adverse Effects 0.000 description 3
- ATBNMWWDBWBAHM-UHFFFAOYSA-N n-decyl-n-methyldecan-1-amine Chemical compound CCCCCCCCCCN(C)CCCCCCCCCC ATBNMWWDBWBAHM-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 2
- GOCCREQJUBABAL-UHFFFAOYSA-N 2,2-dihydroxyacetic acid Chemical compound OC(O)C(O)=O GOCCREQJUBABAL-UHFFFAOYSA-N 0.000 description 2
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 230000001934 delay Effects 0.000 description 2
- KGGVGTQEGGOZRN-PLNGDYQASA-N (nz)-n-butylidenehydroxylamine Chemical compound CCC\C=N/O KGGVGTQEGGOZRN-PLNGDYQASA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 206010019695 Hepatic neoplasm Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 231100000037 inhalation toxicity test Toxicity 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000723 toxicological property Toxicity 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/46—Anti-skinning agents
-
- 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
- C09F9/00—Compounds to be used as driers, i.e. siccatives
Definitions
- the invention relates to the use of additive combinations which are suitable for avoiding undesirable skin formation in oxidatively drying lacquer systems and which
- the additives used according to the invention are characterized by the presence of primary, secondary or tertiary aliphatic amines and / or mixtures thereof in combination with dicarbonyl compounds.
- the invention is in the field of colorless and pigmented oxidatively drying lacquers and paints based on oxidatively drying oils, alkyd resins, epoxy esters and other oxidatively drying, refined oils and printing inks. It concerns new additives that are able to skin formation in the above. To delay paint systems. Additive systems of this type are also able to improve through-drying and flow of the coating systems.
- Oils and binders which are caused by the action of oxygen (preferably atmospheric oxygen) by adding dry substances, e.g. B. metal carboxylates of transition metals, oxidatively crosslinking and thereby form a solid binder film can in the
- phenolic skin inhibitors have a significant delay in drying, so that they can only be used for certain paint formulations.
- Oximes such as B. the methyl ethyl ketoxime or butyraldoxime, however, show due to their
- antioxidants skin preventing agents which prevent the formation of skin on paints over a long period of time and have no or only a very slight delay in drying.
- film hardnesses obtained should not be adversely affected and the products should not have any adverse toxicological properties.
- Another object of the present application was the production of anti-skinning agents that can be used in many different oxidatively drying paints can be incorporated and, due to their physical properties, are unproblematic and can be used in a variety of formulations.
- the invention therefore relates to the use of mixtures of aliphatic amines of the general formula (Ia) and / or their salts of the formula (Ib) described below:
- R 1 , R and R 3 independently of one another for hydrogen (H), alkyl radical C1-C20 linear or branched, optionally unsaturated, optionally mono- or polysubstituted, preferably with hydroxyl, alkoxy or amine radical or cycloalkyl radical with C5-C7; the amine residue optionally also substituted as described and
- R j and R 4 independently of one another for hydrogen (H), alkyl radical C -C 4 , aryl radical Cg-
- R 2 represents H, alkyl radical C 1 -C 4
- the salt-forming anion A ⁇ used can be halides - such as chloride, bromide, iodide - sulfates such as Vi SO4 2 ", carboxylates such as acetate, butyrate, lactate etc. Furthermore, these salt-forming anions A ⁇ can be used in situ when used according to the invention The salt-forming anion A ⁇ is thus formed, for example, from a compound of the formula (II) shown.
- mixtures of compounds of the general formulas (Ia), (Ib) and (II) are used alone or as solutions in water and / or organic solvents. All common solvents, e.g. B. aromatics, white spirits, ketones and alcohols can be used.
- Context means that water is either the sole solvent or more than 50% by weight, based on the solvent mixture, is added in addition to conventional organic solvents (e.g. alcohols).
- organic solvents e.g. alcohols
- the amount of additives used according to the invention depends primarily on the amount of siccatives used in the coating formulation. As a rule, about 1 to 16 moles of mixtures of the compounds of the formulas (Ia), (Ib) and (II) should be added per mole of metal used in the primary dryer (s). Equimolar mixtures of compounds of the formulas (Ia), (Ib) and (II) are preferably used here, but any other quantitative ratios of the compounds according to the invention can also be used.
- connections are used.
- the particular preferred amounts also depend on the type of binder and the pigments used.
- Particularly preferred amounts for unpigmented paints based on long oil alkyd resins e.g. B. 3 to 9 moles of a compound of formula (Ia) and / or (Ib) in a mixture with 3 to 9 moles of a compound of formula (II) based on the amount of metal used in the primary dryer.
- the relative amount of additive to be used can also be greater than 16 mol of the mixture according to the invention (based on the amount of metal in the desiccant).
- the skin-preventing agents according to the invention reliably prevent skin formation in a wide range of binders and when using different siccatives, but do not adversely affect other drying properties of the lacquer.
- a coating formulation consisting of 40.0 g of a long oil alkyd resin (Alkydal F 681 ® from Bayer AG), 4.0 g white spirit D 60, 4.0 g xylene, 1.0 g n-butanol is mixed with 0.18 g a cobalt-containing siccative (dryer 69 ® from Borchers GmbH, contains 6
- Containing butanone oxime was determined to be 8 hours.
- the König pendulum hardness (determined according to DIN 53 157) of the above. Paint films for all three samples were 21 seconds after 1 week of storage.
- a coating formulation consisting of 40.0 g of a long-oil alkyd resin (Alkydal F 681 ® from Bayer AG), 4.0 g white spirit D 60, 4.0 g xylene, 1.0 g n-butanol is mixed with 0.18 g a cobalt-containing siccative (dryer 69 ® from Borchers GmbH, contains 6
- the skin formation time, determined under identical conditions, of a sample without a skin prevention additive was 5 days, that of one Sample containing a usual, appropriate amount of butanone oxime (0.1 g), 52 days.
- the drying time of a corresponding lacquer film (100 ⁇ m wet film layer thickness) of the mixture according to the invention is 2 h 50 min. (Needle trace drying according to test specification 100-94 from Borchers GmbH).
- the drying time, determined under identical conditions, of a sample without skin prevention additive was 3 h 30 min., That of a sample which contained a customary, suitable amount (0.1 g) of butanone oxime was determined to be 4 h.
- a coating formulation consisting of 40.0 g of a long-oil alkyd resin (Alkydal F 681 ® from Bayer AG), 4.0 g white spirit D 60, 4.0 g xylene, 1.0 g n-butanol is added
- Bechers determined. Skin formation was prevented for 104 days. In comparison, the skin formation time, determined under identical conditions, of a sample without a skin-preventing additive was 8 days, that of a sample which contained a customary, suitable amount (0.1 g) of butanone oxime, 23 days. The drying time of a corresponding lacquer film (100 ⁇ m wet film layer thickness) of the mixture according to the invention was 3 h 35 min. (Needle trace drying according to test specification 100-94 from Borchers GmbH). The drying time, determined under identical conditions, of a sample without a skin prevention additive was 3 h 50 min., That of a sample which contained a customary, suitable amount of butanone oxime (0.1 g) was determined to be 8 h. The pendulum hardness according to König (determined according to
- Drying time of a corresponding lacquer film (100 ⁇ m wet film layer thickness) of the mixture according to the invention is 5 h 30 min. (Needle trace drying according to test specification 100-94 from Borchers GmbH). In comparison, the skin formation time, determined under identical conditions, of a sample without skin-preventing additive was 4 days. The one determined under identical conditions
- Drying time of a sample without skin prevention additive is 5 hours.
- a coating formulation consisting of 40.0 g of a long-oil alkyd resin (Alkydal F 681 ® from Bayer AG), 4.0 g white spirit D 60, 4.0 g xylene, 1.0 g n-butanol is mixed with 0.18 g a cobalt-containing siccative (dryer 69 ® from Borchers GmbH, contains 6
- the skin formation time, determined under identical conditions, of a sample without a skin-preventing additive was 6 days, that of a sample which contained a customary, suitable amount (0.1 g) of butanone oxime, 17 days.
- the drying time of a corresponding lacquer film (100 ⁇ m wet film layer thickness) of the mixture according to the invention was 4 h (needle trace drying after
- a lacquer formulation consisting of 40.0 g of a long-oil alkyd resin (Alkydal F 681 ® from Bayer AG), 4.0 g white spirit D 60, 4.0 g xylene, 1.0 g n-butanol is added
- Bechers determined. Skin irritation was prevented for 70 days.
- the skin formation time, determined under identical conditions, of a sample without a skin prevention additive was 5 days, that of a sample which contained a customary, suitable amount of butanone oxime (0.1 g), 36 days.
- the drying time of a corresponding lacquer film (100 ⁇ m wet film layer thickness) of the mixture according to the invention was 2 h (needle trace drying according to test specification 100-94 from Borchers GmbH).
- the drying time, determined under identical conditions, of a sample without skin prevention additive was 2 h 50 min., That of a sample which contained a customary, suitable amount (0.1 g) of butanone oxime became 2 h 30 min. certainly.
- a coating formulation consisting of 41.0 g of a medium-oil alkyd resin (Alkydal F 48 ® from Bayer AG), 4.0 g white spirit D 60, 4.0 g xylene, 1.0 g n-butanol is mixed with 0.08 g a cobalt-containing siccative (dryer 69 ® from Borchers GmbH, contains 6% by weight of Co) and 0.4 g of a calcium-containing siccative (octa-soligen
- Calcium 10 ® from Borchers GmbH, contains 10% by weight calcium). 0.18 g of the mixture listed under 1) is added to the formulation and the time taken for the skin to form on the surface of an approximately half-filled, closed 125 ml PE beaker is determined. Skin formation was prevented for 52 days. In comparison, it was determined under identical conditions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Paints Or Removers (AREA)
Abstract
L"invention concerne l"utilisation de combinaisons d"additifs adaptées pour éviter la formation non souhaitée d"une peau dans des systèmes de peinture à séchage oxydatif, lesquelles améliorent le séchage complet des films de peinture. Ces additifs se caractérisent par la présence d"amines aliphatiques primaires, secondaires ou tertiaires et/ou de mélanges de celle-ci en combinaison avec des composés dicarbonyle.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10010427A DE10010427A1 (de) | 2000-03-03 | 2000-03-03 | Neue Additive zur Vermeidung von Hautbildung an lufttrocknenden Lacken |
DE10010427 | 2000-03-03 | ||
PCT/EP2001/001922 WO2001064795A1 (fr) | 2000-03-03 | 2001-02-21 | Utilisation de combinaisons d"additifs pour eviter la formation d"une peau sur des peintures sechant a l"air |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1268682A1 true EP1268682A1 (fr) | 2003-01-02 |
Family
ID=7633399
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP01913821A Withdrawn EP1268682A1 (fr) | 2000-03-03 | 2001-02-21 | Utilisation de combinaisons d'additifs pour eviter la formation d'une peau sur des peintures sechant a l'air |
Country Status (7)
Country | Link |
---|---|
US (1) | US6849205B2 (fr) |
EP (1) | EP1268682A1 (fr) |
AU (1) | AU2001239266A1 (fr) |
DE (1) | DE10010427A1 (fr) |
NO (1) | NO20024120D0 (fr) |
TW (1) | TW593607B (fr) |
WO (1) | WO2001064795A1 (fr) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005121237A1 (fr) * | 2004-06-02 | 2005-12-22 | Arkema Inc. | Antiskinning compound and compositions containing them |
US7201796B2 (en) * | 2005-07-27 | 2007-04-10 | Arkema Inc. | Antiskinning compound and compositions containing them |
EP1772502A1 (fr) * | 2005-10-07 | 2007-04-11 | DSMIP Assets B.V. | Composition séchant par oxydation, comprenant des composés 1,2 dioxo utilisé dans des couches minces |
CN103102743B (zh) * | 2012-12-12 | 2014-11-05 | 张家港威迪森化学有限公司 | 一种塑料油墨及其制备方法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3259511A (en) * | 1962-09-05 | 1966-07-05 | Johns Manville | Anti-livering agents |
GB8918086D0 (en) * | 1989-08-08 | 1989-09-20 | Ciba Geigy | Coating compositions |
US5183842A (en) * | 1989-08-08 | 1993-02-02 | Ciba-Geigy Corporation | Method of producing an organic, corrosion-resistant surface coating |
US5916930A (en) * | 1996-11-20 | 1999-06-29 | Troy Corporation | Stabilization of biocidal activity in air drying alkyds |
DE19741644A1 (de) * | 1997-09-22 | 1999-03-25 | Borchers Gmbh | Neue Additive zur Vermeidung von Hautbildung an lufttrocknenden Lacken |
EP1115800A1 (fr) * | 1998-08-24 | 2001-07-18 | Akzo Nobel N.V. | Agent anti-usure par abrasion pour des compositions de revetement |
-
2000
- 2000-03-03 DE DE10010427A patent/DE10010427A1/de not_active Withdrawn
-
2001
- 2001-02-21 US US10/220,327 patent/US6849205B2/en not_active Expired - Fee Related
- 2001-02-21 WO PCT/EP2001/001922 patent/WO2001064795A1/fr active Application Filing
- 2001-02-21 EP EP01913821A patent/EP1268682A1/fr not_active Withdrawn
- 2001-02-21 AU AU2001239266A patent/AU2001239266A1/en not_active Abandoned
- 2001-03-01 TW TW090104626A patent/TW593607B/zh not_active IP Right Cessation
-
2002
- 2002-08-29 NO NO20024120A patent/NO20024120D0/no not_active Application Discontinuation
Non-Patent Citations (1)
Title |
---|
See references of WO0164795A1 * |
Also Published As
Publication number | Publication date |
---|---|
NO20024120L (no) | 2002-08-29 |
US20030047112A1 (en) | 2003-03-13 |
US6849205B2 (en) | 2005-02-01 |
WO2001064795A1 (fr) | 2001-09-07 |
TW593607B (en) | 2004-06-21 |
AU2001239266A1 (en) | 2001-09-12 |
DE10010427A1 (de) | 2001-09-06 |
NO20024120D0 (no) | 2002-08-29 |
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