Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From reactant having at least one -n=c=x group as well as...
Reexamination Certificate
1998-07-10
2001-02-06
Acquah, Samuel A. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From reactant having at least one -n=c=x group as well as...
C528S271000, C528S272000, C528S295500, C528S296000, C528S300000, C528S301000, C528S302000, C528S307000, C528S308000, C528S308600, C528S080000, C528S083000, C528S084000, C528S085000, C427S372200, C427S385500, C427S487000
Reexamination Certificate
active
06184332
ABSTRACT:
The present invention relates to new polyesterpolyols based on selected starting materials and to their use in combination with paint polyisocyanates as binder or as binder component in two-component polyurethane coating materials in connection with the coating of metals, woods, paper and board and of polymer moldings. The object of the invention is to provide those new polyesterpolyols which meet the following requirements:
1. The new polyesterpolyols should allow the preparation of polyisocyanate-crosslinkable reactive coating materials having a markedly reduced solvent requirement, as called for in the environmental protection legislation currently in preparation, and especially in the automotive refinish sector. Drafts relating to this are already in existence. (European union of the associations of paint, printing-ink and artist's-colors manufacturers [CEPE] Technology guideline for vehicle refinishes [12.02.92]).
2. The new polyesterpolyols should be suitable as a binder component for polyisocyanate-crosslinkable clearcoats, or pigmented reactive coating materials for producing coatings on metals, woods, paper and board and on polymer moldings.
3. The coatings obtainable from reactive coating materials which comprise the new polyesterpolyols must undergo rapid physical drying at room temperature, for example, for wood varnishing, at about 60° C. for automotive refinishing and at about 80° C. for painting plastics.
4. So that the reactive coating materials which comprise the new polyesterpolyols are very diverse in terms of the possibilities for their use, chemical resistance and high mechanical resistance are absolutely necessary for the cured coating films obtained.
5. Relative to the existing polyesterpolyols for the same field of use, which usually comprise incorporated aromatic components, the new polyesterpolyols should allow the preparation of reactive coating materials whose coating films are notable for outstanding weathering stability, especially gloss retention and yellowing resistance.
6. The new polyesterpolyols should ideally be colorless in dissolved form, so that they can be used to prepare reactive coating materials which as clearcoats and white paints exhibit no intrinsic color.
It has long been known to coat various substrates with two-component polyurethane coating materials based on hydroxyl-containing polyesters, polyethers or polyacrylates and organic polyisocyanates. The resulting coatings are notable in particular for excellent hardness, very good adhesion and good weathering stability. The chemical foundations of these coating materials and coatings are described, inter alia, in “Lackkunstharze” [Synthetic coating resins] Hans Wagner/Hans Friedrich-Sarx, Carl Hanser Verlag, Munich, page 153 to 173, 1971.
The new coating system based on the new polyesterpolyols should in particular satisfy the following requirements:
1. Good gloss retention and yellowing resistance:
The coating film in the case of automotive refinishing, for example, should not degrade more quickly than that of the original finish.
2. No after-embrittlement:
The film must not undergo after-embrittlement even following prolonged weathering.
3. Low drying temperature:
The required drying temperatures and times should be as low as possible, for various reasons including that of saving energy.
4. Reparability:
The drying conditions of such a system should permit not only original finishing but also refinishing with drying at 60° C., 80° C. or room temperature.
As has now surprisingly been discovered, it is possible to achieve the required objects by using the polyesterpolyols of the invention, which are described in more detail below and are based on selected starting materials, as a polyhydroxyl component in two-component polyurethane coating materials.
The invention provides the polyesterpolyols as claimed in claims
1
to
12
and for their use as claimed in claims
13
to
15
.
The invention provides polyesterpolyols having hydroxyl numbers of from 75 to 300, acid numbers of from 5 to 30 and stoichiometrically calculated molecular masses of from 600 to 15,000, synthesized from reaction products of
a) from 5 to 50 mol-% of neopentyl glycol,
b) from 5 to 45 mol-% of trimethylolpropane,
c) from 20 to 51.5 mol-% of hexahydrophthalic acid and/or its anhydride,
d) from 0.5 to 32 mol-% of phthalic acid and/or its anhydride,
e) from 0 to 18 mol-% of other alkanediols from the group 1,2-, 1,3-, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, cyclohexane-1,4-dimethanol, neopentyl glycol hydroxypivalate, cyclohexanediol, trimethylpentanediol, ethylbutylpropanediol, ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propanediol, dipropylene glycol, individually or in a mixture,
f) from 0 to 18 mol-% of other dicarboxylic acids and/or hydroxydicarboxylic acids and/or the anhydride thereof, from the group 5-hydroxyisophthalic acid, isophthalic acid, terephthalic acid, halo acids, such as tetrachloro- and tetrabromophthalic acid, tetrahydrophthalic acid, 1,2-cyclohexanedicarboxylic acid, 1,4-cyclohexanedicarboxylic acid, 4-methylhexahydrophthalic acid, endomethylenetetrahydrophthalic acid, tricyclodecane-dicarboxylic acid, endoethylenehexahydrophthalic acid, camphoric acid (1,2,2-trimethylcyclopentane-1,3-dicarboxylic acid), adipic acid, succinic acid, azelaic acid, sebacic acid, glutaric acid, individually or in a mixture,
g) from 0 to 16 mol-% of monocarboxylic acids and/or hydroxycarboxylic acids from the group benzoic acid, p-tert-butylbenzoic acid, lauric acid, isononanoic acid, 2,2-dimethylpropionic acid, 2-ethylhexanoic acid, caproic acid, caprylic acid, capric acid, Versatic acid, hexahydrobenzoic acid, hydroxypivalic acid, 3-,4-hydroxybenzoic acid, 2-,3-hydroxy-4-methylbenzoic acid, 2-,3-,4-hydroxybenzoic acid, 2-hydroxy-2-phenylpropionic acid, individually in a mixture,
h) from 0 to 14 mol-% of aliphatic and/or cycloaliphatic monoalcohols, the monoalcohols possessing 4 to 18 C atoms,
the molar percentages stated under a), b), c) and d), and if appropriate e), f), g) and h), in each case adding up to 100 mol-%.
One embodiment of the invention relates to polyesterpolyols having hydroxyl numbers of from 100 to 280, acid numbers of from 6 to 28 and stoichiometrically calculated molecular masses of from 750 to 12,000, synthesized from reaction products of
a) from 8 to 47 mol-% of neopentyl glycol,
b) from 8 to 42 mol-% of trimethylolpropane,
c) from 25 to 51 mol-% of hexahydrophthalic acid and/or its anhydride,
d) from 1 to 27 mol-% of phthalic acid and/or its anhydride,
the molar percentages stated under a), b), c) and d) in each case adding up to 100 mol-%.
Another embodiment of the invention constitutes polyesterpolyols having hydroxyl numbers of from 110 to 270, acid numbers of from 7 to 26 and stoichiometrically calculated molecular masses of from 750 to 10,000, synthesized from reaction products of
a) from 10 to 45 mol-% of neopentyl glycol,
b) from 10 to 40 mol-% of trimethylolpropane,
c) from 30 to 50 mol-% of hexahydrophthalic acid and/or its anhydride,
d) from 1 to 22 mol-% of phthalic acid and/or its anhydride,
the molar percentages stated under a), b), c) and d) in each case adding up to 100 mol-%.
A further embodiment of the invention embraces polyesterpolyols having hydroxyl numbers of from 120 to 260, acid numbers of from 8 to 25 and stoichiometrically calculated molecular masses of from 780 to 8000, synthesized from reaction products of
a) from 12 to 43 mol-% of neopentyl glycol,
b) from 12 to 38 mol-% of trimethylolpropane,
c) from 32 to 50 mol-% of hexahydrophthalic acid and/or its anhydride,
d) from 1 to 17 mol-% of phthalic acid and/or its anhydride,
the molar percentages stated under a), b), c) and d) in each case adding up to 100 mol-%.
Another embodiment of the invention includes polyesterpolyols having hydroxyl numbers of from 125 to 255, acid numbers of from 9 to 24 and stoichiometrically calculated molecular masses of from 800 to 7000, synthesized from reaction products of
a) from 14 to 41 mol-% of neopentyl glycol,
b)
Acquah Samuel A.
Kasper Horst M.
Synthopol Chemie Dr. Rer. Pol. Koch GmbH & Co. KG
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