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WO2000011090A1 - Agent anti-usure par abrasion pour des compositions de revetement - Google Patents

Agent anti-usure par abrasion pour des compositions de revetement Download PDF

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Publication number
WO2000011090A1
WO2000011090A1 PCT/EP1999/006157 EP9906157W WO0011090A1 WO 2000011090 A1 WO2000011090 A1 WO 2000011090A1 EP 9906157 W EP9906157 W EP 9906157W WO 0011090 A1 WO0011090 A1 WO 0011090A1
Authority
WO
WIPO (PCT)
Prior art keywords
coating composition
compounds
general formula
formula
compound
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.)
Ceased
Application number
PCT/EP1999/006157
Other languages
English (en)
Inventor
Hans-Jürgen FIGGE
Bodo Weber
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Akzo Nobel NV
Original Assignee
Akzo Nobel NV
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Akzo Nobel NV filed Critical Akzo Nobel NV
Priority to EP99967833A priority Critical patent/EP1115800A1/fr
Priority to AU59704/99A priority patent/AU5970499A/en
Publication of WO2000011090A1 publication Critical patent/WO2000011090A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • 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

Definitions

  • the invention pertains to a coating composition containing at least one compound of the general formula
  • anti-skinning agent wherein X, Y, R 1 -R 4 , and n have the meaning defined below. These compounds are particularly suitable for use as anti-skinning agent for air-drying coating compositions.
  • Air-drying coatings harden under the influence of atmospheric oxygen. Without appropriate precautions, these coatings, when they come into contact with oxygen - e.g. from the air - unstirred, will form a skin on their surfaces. Since air-drying is an irreversible cross-linking process, this skinning generally cannot be cancelled even by renewed thorough mixing of the coating composition and this cross-linked top paint film will be useless for further processing.
  • anti-skinning agents Similar phenomena are also known from primers and coatings which are exposed and subject to prolonged atmospheric action, e.g. dipping primers with a long turn over. Also in such covering or coating compositions use is made of anti-skinning agents. They are further used in fillers. The properties profile of anti-skinning agents requires that skinning be avoided, yet they must not have a negative effect on the actual hardening of the coating following application.
  • butanonoxim which is also marketed under the trade designations Aconox M, Metoxim 100, Ascinin R, Borchinox M2, Exkin 2, etc..
  • ketoxims as anti-skinning agent appears to be critical. For that reason a search was made for a suitable alternative which is not a ketoxim, which is unobjectionable from a toxicological point of view, and which in terms of properties profile is comparable with butanonoxim.
  • Ri and R 2 may be the same or different and represent a C C 6 alkyl group and/or one or more compounds of the general formula
  • R 3 is hydrogen or an alkyl group, R 4 , or when n is greater than 1 , each R-i group, which may be the same or different, is an alkyl, alkenyl, aralkyl, aryl, alkylaryl, amine or group, wherein R 5 represents a d-C alkyl group and n is greater than or equal to 0 and less than or equal to 3.
  • air-drying coating compositions are concerned.
  • coating composition according to the invention is to be interpreted very broadly. For instance, it concerns varnishes, priming coats, filling pastes, glazes, emulsions.
  • the compounds of formula (I) and/or (II) used according to the invention are especially suitable for use in all air-drying systems.
  • the coating compositions according to the invention preferably are solvent- based air-drying coatings and/or house paints. However, they may also be formulated as a water-dilutable or water-borne system.
  • house paints is meant the group of pigmented and unpigmented surface coating compositions which is used in priming or reconditioning coats for coating doors, windows, floors, equipment objects, and the like. They appear in the form of glazes, clear lacquers, priming coats - including fillers - precoats, and finishes and are used for coating substrates common in construction such as wood, metal, synthetic material, but also stone and mineral surfaces (e.g. concrete, ceramic material).
  • the coating compositions according to the invention are alkyd based.
  • a preferred coating composition is a house paint, e.g. an alkyd paint, which contains acetylacetone as the compound of the general formula (I) and no compound of the general formula (II). Furthermore, the use of acetylacetone by itself as the compound of general formula I without a compound of formula II as anti-skinning agent in coating compositions is an advantageous embodiment of the present invention.
  • Ri and R 2 may be, e.g., a methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, tert.-butyl, pentyl or hexyl group.
  • Ri and R 2 each are a methyl group, i.e. acetylacetone.
  • R 3 is hydrogen or an alkyl group, preferably a C C 4 alkyl group, R , or when n is greater than 1 , each R 4 group, which may be the same or different, is an alkyl, alkenyl, aralkyl, aryl, alkylaryl, amine or
  • R 5 is a C C 4 alkyl group and n is greater than or equal to 0 and less than or equal to 3.
  • the alkyl group for R 3 may be an alkyl group with C C ⁇ 5 carbon atoms, preferably with C C 4 carbon atoms.
  • R 3 being hydrogen or methyl is especially preferred.
  • the alkyl group for R4 may be an alkyl group with 1-15 carbon atoms, preferably with 1-4 carbon atoms.
  • alkyl groups suitable for use are decyl, octyl, heptyl, hexyl, pentyl, and the CrC 4 alkyl groups mentioned earlier for Ri and R 2 .
  • the alkenyl groups may be alkenyl groups with 2-15 carbon atoms, preferably 2-4 carbon atoms. Examples of alkenyl groups suitable for use are ethenyl, propenyl (e.g. 1-propenyl or 2-propenyl), and butenyl.
  • the aralkyl groups may be aralkyl groups with 7-15 carbon atoms.
  • the aryl groups may be aryl groups with 6-14 carbon atoms such as phenyl, naphthyl, and anthryl.
  • the alkylaryl groups e.g. with 7-15 carbon atoms, may be, e.g., ethylphenyl.
  • the amine groups employed may be primary, secondary, and tertiary amines. As substituents on the amine are considered, e.g., alkyl, aryl, aralkyl or alkylaryl groups.
  • substituents on the amine are considered, e.g., alkyl, aryl, aralkyl or alkylaryl groups.
  • R 4 For specific examples of these groups reference may be had to the aforementioned examples for R 4 .
  • the C C 4 alkyl groups for R 5 reference may be had to the groups mentioned for R-i and R 2 .
  • the number n substituents R 4 present on heterocycle (II) is 3 at the most, but can also be 0.
  • the present substituents R 4 may all be the same or different.
  • a preferably used compound of formula (I) is acetylacetone.
  • compound of formula (II) preferably compounds of the formula
  • the compounds of formula (I) and formula (II), respectively, can be included in the coating composition as anti-skinning agent by themselves. Moreover, in each case only one compound of the formula in question or several compounds of the formula in question may be used. Preferably, however, in the coating compso according to the invention use is made of at least one compound of general formula (I) and at least one compound of formula (II).
  • compounds of general formula (II) are pyrazole, 3- methylpyrazole, 1 ,4-dimethyipyrazole, imidazole, 1-methylimidazole, 2-methyl- imidazole, 4-methylimidazole, 2-ethylimidazole, 1 ,2-dimethylimidazole, 2-ethyl- 4-methylimidazole, N-(3-aminopropyl)imidazole, and ethyl-(3-aminopyrazole-4- carboxylate).
  • the compounds imidazole and 1 ,2-dimethylimidazole also have preference.
  • the compounds of formula (I) and formula (II) are used in the coating composition together in an amount of 0,1 to 5 wt.%, more preferably 0,5 to 3 wt.%, calculated on the coating composition.
  • the proportion thereof, calculated on the overall quantity of coating material preferably is 0,05 to 2 wt.%, especially preferably 0,25 to 1 wt.%.
  • the coating composition according to the invention may contain siccatives, for instance the naphthanate salt or octoate salt of cobalt, manganese, nickel, vanadium, zirconium or molybdenum.
  • Test coating compositions with anti-skinning agent For the determination the above-described high-gloss white test coating composition was mixed with the different anti-skinning agents in different variations of quantities and mixed thoroughly with an impeller. To evaluate the surface drying a 100 ⁇ m application of each of the thus obtained test compositions was made on lined paper and the surface drying was assigned a value after 4 and 8 hours in accordance with DIN 53230. About 200 ml of the different test coating compositions were stored in a PE beaker at room temperature, exposed, and the skinning after 24 hours was evaluated in accordance with DIN 53230. The results are listed in the Table below. Each time the above-described test coating composition without further additives was also assigned a value as a blank test sample. Results:
  • the aforesaid recipe items were dissolved for 15 minutes and then subjected to 1 passage through an agitator mill.
  • the grain size subsequently was less than ⁇ 10 ⁇ m
  • the coating compositions ware set to a processing viscosity of 5,0 to 5,5 dPas.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Paints Or Removers (AREA)

Abstract

L'invention concerne une composition de revêtement contenant au moins un composé selon la formule générale (I) et/ou au moins un composé selon la formule (II) comme agent anti-usure par abrasion. Dans les formules, X, Y, R1-R4 et n ont la signification définie dans le descriptif. Ces composés sont particulièrement appropriés comme agent anti-usure par abrasion pour les compositions de revêtement séchant à l'air.
PCT/EP1999/006157 1998-08-24 1999-08-20 Agent anti-usure par abrasion pour des compositions de revetement Ceased WO2000011090A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP99967833A EP1115800A1 (fr) 1998-08-24 1999-08-20 Agent anti-usure par abrasion pour des compositions de revetement
AU59704/99A AU5970499A (en) 1998-08-24 1999-08-20 Anti-skinning agent for coating compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19838395 1998-08-24
DE19838395.9 1998-08-24

Publications (1)

Publication Number Publication Date
WO2000011090A1 true WO2000011090A1 (fr) 2000-03-02

Family

ID=7878525

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1999/006157 Ceased WO2000011090A1 (fr) 1998-08-24 1999-08-20 Agent anti-usure par abrasion pour des compositions de revetement

Country Status (3)

Country Link
EP (1) EP1115800A1 (fr)
AU (1) AU5970499A (fr)
WO (1) WO2000011090A1 (fr)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001064795A1 (fr) * 2000-03-03 2001-09-07 Borchers Gmbh Utilisation de combinaisons d"additifs pour eviter la formation d"une peau sur des peintures sechant a l"air
EP1275701A1 (fr) * 2001-07-11 2003-01-15 Borchers GmbH Agent inhibiteur de peau
EP2474578A1 (fr) 2011-01-06 2012-07-11 Rahu Catalytics Limited Compositions antipeaux
US8318836B2 (en) 2006-07-07 2012-11-27 Omg Uk Technology Limited Liquid hardening
WO2014122432A1 (fr) 2013-02-11 2014-08-14 Chemsenti Limited Composition de revêtement durcissable par oxydation
WO2014122433A1 (fr) 2013-02-11 2014-08-14 Chemsenti Limited Siccatif pour revêtement à base d'alkyde
WO2014122434A1 (fr) 2013-02-11 2014-08-14 Catexel Limited Composition de revêtement durcissable oxydativement
CN104250512A (zh) * 2014-09-25 2014-12-31 常熟市方塔涂料化工有限公司 水性醇酸底面合一防锈漆及其制备方法
WO2015011430A1 (fr) 2013-07-25 2015-01-29 Omg Uk Technology Limited Catalyseurs encapsulés
WO2021260037A1 (fr) 2020-06-24 2021-12-30 Borchers Gmbh Peintures contenant des siccatifs à base de composés de vanadium portant des anions d'acides sulfoniques en tant que contre-ions
WO2023030700A1 (fr) 2021-08-30 2023-03-09 Borchers Gmbh Procédé pour améliorer les performances de résine
WO2023052294A1 (fr) 2021-09-30 2023-04-06 Borchers Gmbh Procédé pour améliorer la performance de résine à l'aide d'acides de lewis
WO2023117421A1 (fr) 2021-12-22 2023-06-29 Borchers Gmbh Peintures contenant des siccatifs à base de composés de vanadium portant divers anions acides

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3346523A (en) * 1964-08-03 1967-10-10 Exxon Research Engineering Co Coating compositions made from oximes
US3701781A (en) * 1971-05-14 1972-10-31 Cincinnati Milacron Chem Alpha-oximino ketone antiskinning agents
EP0078866A1 (fr) * 1980-05-12 1983-05-18 Nihon Parkerizing Co., Ltd. Formation de revêtements sur des surfaces d'aluminium
US4618371A (en) * 1984-05-22 1986-10-21 Basf Aktiengesellschaft Coating materials which contain α-hydroxyketones as antiskimming agents
US5521272A (en) * 1993-09-03 1996-05-28 Olin Corporation Isocyanate-crosslinked coatings having reduced yellowing
EP0903380A1 (fr) * 1997-09-22 1999-03-24 Borchers GmbH Agent antipeaux pour vernis sèchant à l'air

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3346523A (en) * 1964-08-03 1967-10-10 Exxon Research Engineering Co Coating compositions made from oximes
US3701781A (en) * 1971-05-14 1972-10-31 Cincinnati Milacron Chem Alpha-oximino ketone antiskinning agents
EP0078866A1 (fr) * 1980-05-12 1983-05-18 Nihon Parkerizing Co., Ltd. Formation de revêtements sur des surfaces d'aluminium
US4618371A (en) * 1984-05-22 1986-10-21 Basf Aktiengesellschaft Coating materials which contain α-hydroxyketones as antiskimming agents
US5521272A (en) * 1993-09-03 1996-05-28 Olin Corporation Isocyanate-crosslinked coatings having reduced yellowing
EP0903380A1 (fr) * 1997-09-22 1999-03-24 Borchers GmbH Agent antipeaux pour vernis sèchant à l'air

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001064795A1 (fr) * 2000-03-03 2001-09-07 Borchers Gmbh Utilisation de combinaisons d"additifs pour eviter la formation d"une peau sur des peintures sechant a l"air
US6849205B2 (en) 2000-03-03 2005-02-01 Borchers Gmbh Use of additive combinations for preventing skin formation on air-drying lacquers
EP1275701A1 (fr) * 2001-07-11 2003-01-15 Borchers GmbH Agent inhibiteur de peau
US6730157B2 (en) 2001-07-11 2004-05-04 Borchers Gmbh Anti-skinning agents having a mixture of organic compounds and coating compositions containing them
US7344588B2 (en) 2001-07-11 2008-03-18 Borchers Gmbh Anti-skinning agents having a mixture of organic compounds and coating compositions containing them
US8497314B2 (en) 2006-07-07 2013-07-30 Omg Uk Technology Ltd. Liquid hardening
US8318836B2 (en) 2006-07-07 2012-11-27 Omg Uk Technology Limited Liquid hardening
US8492461B2 (en) 2006-07-07 2013-07-23 Omg Uk Technology Ltd. Liquid hardening
US9593232B2 (en) 2006-07-07 2017-03-14 Omg Uk Technology Ltd. Liquid hardening
US8642685B2 (en) 2006-07-07 2014-02-04 OMG UK Technology, Ltd Liquid hardening
US8664306B2 (en) 2006-07-07 2014-03-04 Omg Uk Technology Ltd. Liquid hardening
WO2012093250A1 (fr) 2011-01-06 2012-07-12 Omg Additives Limited Compositions anti-peaux
EP2474578A1 (fr) 2011-01-06 2012-07-11 Rahu Catalytics Limited Compositions antipeaux
WO2014122432A1 (fr) 2013-02-11 2014-08-14 Chemsenti Limited Composition de revêtement durcissable par oxydation
WO2014122434A1 (fr) 2013-02-11 2014-08-14 Catexel Limited Composition de revêtement durcissable oxydativement
WO2014122433A1 (fr) 2013-02-11 2014-08-14 Chemsenti Limited Siccatif pour revêtement à base d'alkyde
US9732251B2 (en) 2013-02-11 2017-08-15 Chemsenti Limited Drier for alykd-based coating
US9890297B2 (en) 2013-02-11 2018-02-13 Chemsenti Limited Oxidatively curable coating composition
US10457831B2 (en) 2013-02-11 2019-10-29 Catexel Limited Oxidatively curable coating composition
WO2015011430A1 (fr) 2013-07-25 2015-01-29 Omg Uk Technology Limited Catalyseurs encapsulés
CN104250512A (zh) * 2014-09-25 2014-12-31 常熟市方塔涂料化工有限公司 水性醇酸底面合一防锈漆及其制备方法
WO2021260037A1 (fr) 2020-06-24 2021-12-30 Borchers Gmbh Peintures contenant des siccatifs à base de composés de vanadium portant des anions d'acides sulfoniques en tant que contre-ions
WO2023030700A1 (fr) 2021-08-30 2023-03-09 Borchers Gmbh Procédé pour améliorer les performances de résine
WO2023052294A1 (fr) 2021-09-30 2023-04-06 Borchers Gmbh Procédé pour améliorer la performance de résine à l'aide d'acides de lewis
WO2023117421A1 (fr) 2021-12-22 2023-06-29 Borchers Gmbh Peintures contenant des siccatifs à base de composés de vanadium portant divers anions acides

Also Published As

Publication number Publication date
EP1115800A1 (fr) 2001-07-18
AU5970499A (en) 2000-03-14

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