Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2001-08-22
2003-07-15
Harlan, Robert D. (Department: 1713)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C549S378000
Reexamination Certificate
active
06593479
ABSTRACT:
The invention pertains to a coating composition comprising a first compound comprising at least one bicyclo- or spiro-orthoester group.
BACKGROUND OF THE INVENTION
The use of compounds comprising bicyclo-orthoester groups in coating compositions is known from U.S. Patent publication No. 4,338,240. In this patent publication the use and the preparation of bicyclo-orthoester-functional compounds (hereinafter bicyclo-orthoester will be abbreviated to BOE) is described. Described are, e.g., BOE-functional compounds, which are the adduct of two compounds comprising one hydroxyl group and one BOE group and one compound comprising two isocyanate groups. The compounds are cross-linked by means of cationic ring opening homopolymerization of the BOE groups. In that case, however, the presence of moisture has to be excluded. Furthermore, energy in the form of ultraviolet, infrared or microwave irradiation or heat has to be supplied during the polymerization process.
SUMMARY OF THE INVENTION
The invention now provides a coating composition of the aforementioned type which is free of said drawbacks. For that reason the coating composition mentioned in the opening paragraph is characterized in that it comprises a second compound comprising at least two hydroxyl-reactive groups.
A coating composition comprising a compound comprising at least one bicyclo- or spiro-orthoester group (hereinafter spiro-orthoester will be abbreviated to SOE) is a composition having latent hydroxyl groups. In the presence of water or moisture from the air the BOE or SOE groups will be hydrolyzed, forming hydroxyl groups. This reaction is also known as deblocking. During deblocking few if any volatile components are released. When the BOE- or SOE-group is deblocked in this manner, it is not possible to obtain a homopolymer of BOE- or SOE groups by cationic polymerization. However, it has now been found that when a second compound comprising at least two hydroxyl-reactive groups is present in the composition, the deblocked hydroxyl groups can react with the hydroxyl-reactive groups to give a cross-linked polymer.
BOE- and SOE-functional compounds may be used as main binders or as reactive diluents in the coating compositions of the present invention.
The use of compounds comprising BOE or SOE groups in coating compositions has several advantages over the use of compounds having free hydroxyl groups, such as hydroxyl-functional reactive diluents, hydroxyl-functional main binders, e.g. polyester polyols and acrylate polyols, and even compounds where the BOE or SOE groups have already been hydrolyzed.
Firstly, the viscosity of compounds comprising BOE or SOE groups is lower than that of the corresponding hydrolyzed compounds. In consequence, less viscosity-reducing solvent which evaporates in air is needed in the coating composition.
Secondly, because of the stability of the BOE- and SOE-functional compounds the pot life:drying time ratio of compositions according to the invention is particularly favorable, for hydrolysis only takes place in the presence of water or moisture.
Thirdly, in coating compositions of the present invention BOE- and SOE functional compounds have the advantage that hydrolysis of the BOE or SOE group produces a substantial increase in the composition's viscosity. A high viscosity will give reduced sagging of the coating composition on the substrate.
Finally, it has been found that the coating compositions of the present invention provide a high build behavior.
DETAILED DESCRIPTION OF THE INVENTION
By BOE groups are meant in this connection groups having a structure according to formula I
wherein
X and Z are independently from each other selected from linear or branched alk(en)ylene groups with 1-4 carbon atoms optionally containing an oxygen or a nitrogen atom;
Y is nothing or is selected independently of X and Z from linear or branched alk(en)ylene groups with 1-4 carbon atoms optionally containing an oxygen or a nitrogen atom;
R
1
and R
2
may be the same or different and are selected from the group of monovalent radicals comprising
hydrogen, hydroxyl, alk(en)yl groups comprising 1-30 carbon atoms which may be linear or branched and may optionally contain one or more heteroatoms and groups selected from the group of oxygen, nitrogen, sulphur, phosphorus, sulphone, sulphoxy, and ester, optionally substituted with epoxy, cyano, amino, thiol, hydroxyl, halogen, nitro, phosphorus, sulphoxy, amido, ether, ester, urea, urethane, thioester, thioamide, amide, carboxyl, carbonyl, aryl, and acyl groups, and
divalent radicals comprising
alk(en)ylene groups having 1-10 carbon atoms which groups may be linear or branched and may optionally contain one or more heteroatoms and groups selected from the group of oxygen, nitrogen, sulphur, phosphorus, sulphone, sulphoxy, and ester, optionally substituted with epoxy, cyano, amino, thiol, hydroxyl, halogen, nitro, phosphorus, sulphoxy, amido, ether, ester, urea, urethane, thioester, thioamide, amide, carboxyl, carbonyl, aryl, and acyl groups, ester groups; ether groups; amide groups; thioester groups; thioamide groups; urethane groups; urea groups; and a single bond.
Preferably, X, Y, and Z are methylene. R
1
and R
2
in that case are linked to a divalent 2,6,7-trioxabicyclo[2.2.2]octane radical.
In the case of R
1
and R
2
being both monovalent radicals, the BOE group as defined by formula I is the same as the BOE-functional compound. Monovalent radicals R
1
and R
2
are preferably independently from each other selected from the group of hydrogen, hydroxyl, and linear or branched alk(en)yl groups having 1-20 carbon atoms, optionally substituted with one or more hydroxyl groups and optionally comprising an ester group. Examples of such groups are: methyl, methylol, ethyl, ethylol, propyl, propylol, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, a —CH
2
—CH
2
—O—CO—C
1-20
alk(en)yl group, and mixtures thereof.
Preferably, R
1
is linear or branched alk(en)yl having 1-20 carbon atoms, optionally substituted with hydroxyl, while R
2
is methyl or ethyl. Alternatively, R
1
can be methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and mixtures thereof, while R
2
can be methylol, ethyl, ethylol or a —CH
2
—CH
2
—C—CO—C
1-20
alk(en)yl group.
When a divalent radical is selected for either or both R
1
or R
2
groups, high-molecular weight BOE-functional compounds can be formed. These may be adducts or polymers comprising several BOE groups. Thus two BOE groups can form an adduct by selecting a monovalent radical for one of the two R
1
and R
2
groups, and a divalent radical for the other. The BOE groups will then be linked together via the divalent radical. BOE groups may also be linked via the divalent radicals to monomer or oligomer compounds. Such BOE-functional compounds are, e.g. described in above-mentioned U.S. Pat. No. 4,338,240. For example, two BOE groups may be linked to a dimer fatty acid, e.g. “PRIPOL®” 1009 (available from Unichema Chemie BV, Gouda, Netherlands). Alternatively, in the aforementioned configuration the BOE groups can function as side groups or terminal groups in a polymer chain. The polymers can be, e.g., polyesters, polyethers, polyacrylates, polyamides or polyurethanes. When the divalent radical is a single bond, the BOE group is bonded directly to the polymer. When the R
1
and R
2
groups are both divalent, the BOE groups can be incorporated into the main chain of a polymer or they can serve to link two polymer chains together. Preferably, one or both R
1
and R
2
groups are selected from the group of ester, ether, urethane, a single bond, and alk(en)ylene groups having 1-10 carbon atoms which may be linear or branched and may contain one or more ester, ether, or urethane groups.
The term SOE groups in this case refers to groups having a structure according to formula II or III
wherein
R
3
and R
5
are independently from each other selected from the group of linear or branched alk(en)yl, aryl or acyl optionally containing one or more oxygen, nitrogen, sulphur or pho
Hobel Klaus
Klinkenberg Huig
Noomen Arie
van den Berg Keimpe Jan
van Oorschot Josephus Christiaan
Akzo Nobel N.V.
Harlan Robert D.
McGillycuddy Joan M.
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