Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...
Reexamination Certificate
2000-05-04
2002-09-17
Dawson, Robert (Department: 1712)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
C528S403000, C528S408000, C526S273000, C549S512000, C568S606000, C525S404000, C524S284000, C524S800000, C524S612000
Reexamination Certificate
active
06451926
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to oxidatively curable coating compositions containing polyether alcohols which are; the reaction product of 3,4-epoxy-1-butene and optionally a saturated oxirane, initiated with water or an alcohol. The invention also relates to oxidatively cured films formed from the coating compositions.
BACKGROUND OF THE INVENTION
Recently, intense research efforts in the coating industry have been directed to reducing volatile organic compounds (VOCs) in coating formulations due to environmental concern and governmental regulation. One of the emerging technologies developed for this purpose is to use reactive diluents in coating formulations. A typical reactive diluent has a viscosity which is low enough to enable it to function as an organic solvent although it remains in the films when the coatings are cured. In order to achieve that and achieve optimum coating properties, a reactive diluent needs to be a non-volatile liquid under the curing condition and should have a functionality which allows it to participate in the curing process. Accordingly, a non-volatile liquid at room temperature with allyl functionality would be desirable as a reactive diluent for oxidatively curable coatings.
In a paper presented at the 65th Annual Meeting of the Federation of Societies for Coatings Technology (October 1987) by J. W. Kilapczyk of Monsanto, and published in the
Journal of Coatings Technology,
vol. 60, no. 756, p. 63, 1988, it was reported that poly(allyl glycidyl ether) resins significantly accelerate the curing of thin acrylate and methacrylate films at low temperature in air and under practical anaerobic conditions.
In J.M.S.-
Pure Appl. Chem.,
A33 (4), p.509 (1996) it was reported that lacquers obtained from an alkyd resin containing 10-16 weight % of glycerol allyl ether exhibit short drying time, good hardness of coatings, and good water resistance. In
J. Appl. Polym. Sci.,
70, 2031 (1998) it was also reported that high hardness of coatings cured in air using photoinitiators can be achieved for an unsaturated polyester resin with polyfunctional allyl ether monomers incorporated into polyester molecules as the end groups or as the pendant geminal groups.
Poly(allyl ethers) derived from polyols and carbohydrates, particularly allylated pentaerythritol, trimethylolpropane, and starches and sugars have been widely investigated as monomers suitable for protective coatings. These materials are attractive since they undergo autoxidative polymerization in contact with air. However, because of slow curing rates, color formation, high cost, and relatively poor substrate bonding strength, films of these allyl ethers have limited commercial use (see Allyl Compounds and Their Polymers by C. E. Schildknecht, Wiley Interscience, 1973).
Accordingly, it is an object of the present invention to overcome the above deficiencies and to provide oxidatively curable, low cost, allylic polyethers that are fast curing, have superior coating properties and which provide films having good hardness and high resistance to chemical attack.
SUMMARY OF THE INVENTION
The invention relates to oxidatively curable coating compositions containing an EpB polyether alcohol or a derivative thereof, which is a reaction product of 3,4-epoxy-1-butene and optionally a saturated oxirane compound, initiated with water or an alcohol. The coating compositions may contain other curable resins such that the EpB polyether alcohol functions as a reactive diluent. Alternatively, the EpB polyether alcohol can function as the main film-former in the oxidatively curable coating composition. The coating compositions containing EpB polyether alcohols cure oxidatively, preferably with commercially available metal driers.
The invention also relates to an EpB polyether alcohol or a derivative thereof, which is the reaction product of 3,4-epoxy-1-butene and a saturated oxirane compound, initiated with water or an alcohol. It is not necessary to react an alk-1-enyloxy oxirane such as those disclosed in U.S. Pat. No. 5,200,437 to Dougherty et al. to make the oxidatively curable EpB polyether alcohols of the invention. These alk-1-enyloxy oxiranes are costly and cannot be incorporated using acid catalysis due to the sensitivity of the vinyl ether group towards acid. These EpB polyether alcohols can function as reactive diluents in oxidatively curable coating compositions. In addition, these EpB polyether alcohols can function as a coating resin alone without other curable resins. The EpB polyether alcohols are also useful as surfactants, resins, chain extenders, monomers, or as an additive for various oxidatively curable coating systems including alkyds, unsaturated polyesters, acrylates, epoxies, urethanes, and latex polymers. The EpB polyether alcohols cure oxidatively, using commercially available metal driers.
One embodiment of the invention provides an oxidatively curable coating composition comprising (a) about 5-100 weight % of an oxidatively curable EpB polyether alcohol or a derivative thereof, (b) about 0-95 weight % of a curable resin, (c) about 0-40 weight % of an organic solvent, and (d) a catalytic amount of a metal drier. The EpB polyether alcohol is a reaction product of: (i) 3,4-epoxy-1-butene and (ii) an initiator selected which is water or an alcohol. The EpB polyether alcohol contains n units of residue (I) and m units of residue (II).
The sum of (n+m) is about 1 to 70 and the ratio of n/(n+m) is a value in the range of about 0.70 to 1.00.
In another embodiment of the invention, there is provided an EpB polyether alcohol which is a reaction product of: (a) 3,4-epoxy-1-butene, (b) a saturated oxirane compound; and (c) an initiator which is water or alcohol. The reactants used to make the EpB polyether alcohol which contains a saturated oxirane compound do not include an alk-1-enyloxy oxirane. The EpB polyether alcohol contains n units of residue (I) and m units of residue (II) shown above. The sum of n+m is about 2 to 70 and the ratio of n/(n+m) is a value in the range of about 0.70 to 0.95.
In a third embodiment of the invention, there is provided an oxidatively curable coating composition which contains:(a) about 5-100 weight % of an oxidatively curable polyether alcohol or derivative thereof; (b) about 0-95 weight % of a curable resin; (c) about 0-40 weight % of an organic solvent; and (d) a catalytic amount of a metal drier. The EpB polyether alcohol is a reaction product of:(i) 3,4-epoxy-1-butene: (ii) a saturated oxirane compound and (iii) an initiator which is water or an alcohol. The polyether alcohol contains n units of residue (I) and m units of residue (II) as shown above, wherein the sum of n+m is about 1 to 70 and the ratio of n/(n+m) is a value in the range of about 0.70 to 1.00.
A fourth embodiment of the invention provides a polyether alcohol which is a block copolymer formed by reacting (i) 3,4-epoxy-1-butene, (ii) a saturated oxirane compound, and (iii) an initiator which is water or an alcohol, with the proviso that the reactants do not include an alk-1-enyloxy oxirane. The block copolymer contains n units of residue (I) and m units of residue (II) shown above, wherein the sum of n+m is a value in the range of about 1 to 70 and the ratio of n/(n+m) is a value in the range of about 0.70 to 1.00.
A fifth embodiment of the invention relates to an oxidatively cured film of the oxidatively curable coating composition containing an EpB polyether alcohol which is a reaction product of: 3,4-epoxy-1-butene and an initiator which is water or an alcohol as described above.
A sixth embodiment of the invention relates to an oxidatively cured film of the oxidatively curable coating composition containing an EpB polyether alcohol which is a reaction product of: 3,4-epoxy-1-butene, a saturated oxirane compound, and an initiator which is water or an alcohol as described above.
A seventh embodiment of the invention provides a composition comprising (a) an oxidatively curable EpB polyether alcohol which is a reaction product of 3,4-epoxy-1-bu
Falling Stephen Neal
Kuo Thauming
Liu Yao-Ching
McEntire Edward Enns
Slegeir William Anthony
Blake Michael J.
Eastman Chemical Company
Graves Bernard J.
Peng Kuo-Liang
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