Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – At least one aryl ring which is part of a fused or bridged...
Reexamination Certificate
1999-02-03
2001-08-14
Woodward, Ana (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
At least one aryl ring which is part of a fused or bridged...
C524S111000, C524S380000, C524S381000, C524S386000, C524S388000, C524S389000, C524S391000, C524S502000, C524S513000, C524S514000, C427S385500, C427S388100, C427S389700, C427S391000, C427S393500, C427S395000
Reexamination Certificate
active
06274660
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a coating composition, to a process for preparing it and to its use.
BACKGROUND OF THE INVENTION
The coating materials that are known nowadays, examples being clearcoats, topcoats and surfacers, are based on binders which are required to have a large number of different functionalities in order that required coating properties can be achieved. Such coating systems are known, for example, from the German Patents DE 44 07 415, DE 44 07 409 or DE 43 10 414. The disadvantage of all these coating materials is that the solids contents cannot be increased ad infinitum. With these systems, therefore, reducing the solvent emission is a possibility only within narrow confines.
SUMMARY OF THE INVENTION
The present invention, therefore, is based on the object of providing a coating composition which relative to the coating compositions known to date has an increased solids content in conjunction with good scratch resistance and high reflow.
DETAILED DESCRIPTION OF THE INVENTION
This object is achieved in accordance with the invention in that said composition comprises polyols I which are obtained by subjecting oligomers of the formula I
R
1
R
2
C═[═CH—R—CH═]
n
═CR
3
R
4
(I)
in which R=—(—CH
2
—)
m
—, in which the index m is an integer from 1 to 6, or
in which X=—CH
2
— or an oxygen atom
R
1
,R
2
,R
3
and
R
4
independently of one another=hydrogen atoms or alkyl; and
the index n=an integer from 1 to 15;
to hydroformylation and reducing the resultant aldehyde-functional products I to give the polyols I, which, if desired, are subjected to partial or complete hydrogenation.
The value n in the formula I stands for the number of divalent radicals R which have been introduced by ring-opening metathesis reaction into the oligomers I derived from cyclic olefins such as, for example, cyclopropene, cyclopentene, cyclobutene, cyclohexene, cycloheptene, norbornene, 7-oxanorbornene or cyclooctene. Preferably, as large as possible a proportion—such as, for example, at least 40% by weight (as determined by integrating the areas of the gas chromatograms; instrument: Hewlett Packard; detector: flame ionization detector; column: DB 5.30 m×0.32 mm, covering: 1&mgr;; temperature program: 60° C. for 5 minutes, isothermal, heating rate 10° C./min, max: 300° C.)—of the oligomer mixtures I which can be employed in accordance with the invention has a value of n>1. The value n and thus the degree of ring-opening metathesis can, as set out further below, be influenced by the activity of the metathesis catalyst used.
The radicals R
1
,R
2
R
3
and R
4
stand independently of one another for hydrogen or alkyl, where the term “alkyl” embraces straight-chain and branched alkyl groups.
Preferably, the groups concerned are straight-chain or branched C
1
-C
15
-alkyl, preferably C
1
-C
10
-alkyl, and with particular preference, C
1
-C
5
-alkyl groups. Examples of alkyl groups are, in particular, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 1,1-dimethylpropyl, 1,2,2-trimethylpropyl, 1-ethylbutyl, 2-ethylbutyl, 1-ethyl-2-methylpropyl, n-heptyl, 1-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 1-propylbutyl, octyl, decyl, dodecyl, etc.
The degree of branching and the number of carbon atoms of the terminal alkyl radicals R
1
,R
2
,R
3
and R
4
depend on the structure of the acyclic monoolefins of the hydrocarbon mixture used and on the activity of the catalyst. As described with more precision below, the activity of the catalyst influences the degree of cross-metathesis (self-metathesis) of the acyclic olefins, with the formation of structurally new olefins into which, formally, cyclopentene is then inserted in the manner of a ring-opening metathesis addition polymerization.
Preference is given to the use of oligomer mixtures featuring an increased proportion of oligomers having only one terminal double bond. The oligomer is preferably prepared by subjecting a hydrocarbon mixture obtained by cracking from petroleum processing (C
5
cut) and comprising a cyclic monoolefin such as cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene, norbornene or 7-oxanorbornene, plus acyclic monoolefins, to a homogeneous or heterogeneous metathesis reaction.
The metathesis reaction formally comprises
a) the disproportionation of the acyclic monoolefins of the hydrocarbon mixture by cross-metathesis,
b) the oligomerization of the cyclic monoolefin by ring-opening metathesis,
c) chain termination by reaction of the oligomers from b) with an acyclic olefin of the hydrocarbon mixture or of a product from a),
it being possible for steps a) and/or b) and/or c) to be gone through repeatedly, either alone or in combination.
Step a)
The cross-metathesis of the acyclic monoolefins will be illustrated using the metathesis of 1-pentene and 2-pentene as an example:
CH
2
═CH—C
3
H
7
+&rlarr2;propane+1 butene+2-hexane+3-hepteneCH
3
—CH═CH—C
2
H
5
The combination of cross-metathesis of different acyclic olefins and self-metathesis of the same acyclic olefins, such as, for example, the self-metathesis of 1-pentene to ethene and 4-octene, and repetition of this reaction, produce a large number of monoolefins with different structures and numbers of carbon atoms, these monoolefins forming the end groups of the oligomers I. The proportion of cross-metathesis products, which increases as the activity of the catalyst used goes up, also influences the double bond content of the oligomers. For example, in the self-metathesis of 1-pentene described above, ethene is released which, if desired, can escape in gas form, with one double bond equivalent being removed from the reaction. At the same time, there is an increase in the proportion of oligomers without terminal double bonds. Thus in the above example an oligomer without terminal double bonds is formed, for example, by insertion of the cyclic monoolefin into 4-octene.
Step b) The average number of insertions of the cyclic monoolefin in the growing chain in the sense of a ring-opening metathesis addition polymerization determines the average molecular weight of the oligomer mixture I that is formed. Preferably, oligomer mixtures I having an average molecular weight of at least 274 g per mol are formed by the process of the invention, which corresponds to an average number of three units of a cyclic monoolefin per oligomer.
Step c)
Chain termination takes place by reaction of oligomers that still have an active chain end in the form of a catalyst complex (alkylidene complex) with an acyclic olefin; in the course of this reaction, ideally, an active catalyst complex is recovered. In that case, the acyclic olefin may originate unchanged from the hydrocarbon mixture originally employed for the reaction, or may have been modified in a cross-metathesis in accordance with stage a).
Very generally, the process is suitable for preparing oligomers I from hydrocarbon mixtures which comprise acyclic and cyclic monoolefins: monoolefins such as, for example, cyclobutene, cyclopentene, cyclohexene, cycloheptene, norbornene or 7-oxanorbornene, especially cyclopentene. Variants of this process are described, for example, in the article by M. Schuster and S. Bleckert in Angewandte Chemie, 1997, Volume 109, pages 2124 to 2144.
Preference is given to the use of a hydrocarbon mixture obtained industrially in the processing of petroleum, it being possible if desired to subject said mixture to catalytic partial hydrogenation beforehand in order to remove dienes. A particularly suitable mixture for use in the present process is, for example, a mixture enriched in saturated and unsaturated C
5
-hydrocarbons (C
5
cut). In order to obtain th
Baumgart Hubert
Farwick Thomas
Hagemeister Edeltraud
Rink Peter-Heinz
Schwab Peter
BASF Coatings AG
Woodward Ana
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