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
2001-03-02
2003-09-23
Gorr, Rachel (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...
C525S329900, C525S185000, C560S025000, C560S115000, C560S158000
Reexamination Certificate
active
06624280
ABSTRACT:
This application claims priority under 35 USC §120 upon International PCT Application PCT/EP99 filed Aug. 27, 1999 and German Patent Application DE 198 39 453.3, filed Aug. 29, 1998.
The present invention relates to novel oligomeric and high molecular mass products of reaction of allophanic esters with nucleophilic compounds and also to novel low molecular mass, oligomeric and high molecular mass compounds containing lateral and/or terminal allophanate groups. The present invention additionally relates to the use of these reaction products and compounds in coating compositions, films, adhesives, and sealing compounds. The present invention further relates to novel coating compositions, films, adhesives and sealing compounds which comprise the novel oligomeric and/or high molecular mass products of reaction of allophanic esters with nucleophilic compounds and/or the novel low molecular mass, oligomeric and high molecular mass compounds containing lateral and/or terminal allophanate groups. The present invention relates not least to novel processes for preparing these reaction products or compounds.
Clearcoat materials for the automobile sector which comprise oligomers and/or polymers containing lateral and/or terminal carbamate (—O—C(O)—NH
2
) groups are known from the patents EP-A-0 594 071, EP-A-0 594 068, EP-A-0 594 142, WO 94/10212, WO 94/10211, WO 94/10213, DE-C-36 34 780 and U.S. Pat. No. 5,098,947. They may be prepared by different processes, which are described in these patents. It has, however, proven appropriate to prepare these oligomers and polymers containing lateral and/or terminal carbamate groups by reacting hydroxyl-containing oligomers and polymers with methyl carbamate. In some cases of transcarbamation, however, the reactivity of methyl carbamate is comparatively low, so that relatively high temperatures must be employed in order to obtain higher reaction rates. However, the higher temperatures may cause thermal damage to the products, after which they are no longer suitable for use, for example, in clearcoat materials.
Low molecular mass and oligomeric compounds containing lateral and/or terminal carbamate (—HN—C(O)—O—R) groups are described in the patents U.S. Pat. No.4,710,542 and EP-B-0 245 700 and also in the article by B. Singh and co-workers,“Carbamylmethylated Melamines, Novel Cross-linkers for the Coatings Industry”, in Advanced Organic Coatings Science and Technology Series, 1991, Volume 13, pages 193 to 207. These compounds comprise reaction products of carbamates, especially alkyl carbamates, and melamine resins. These lateral and/or terminal carbamate (—HN—C(O)—O—R) groups are no longer capable of entering into crosslinking reactions with the lateral and/or terminal carbamate (—O—C(O)—NH
2
) groups. These low molecular mass and oligomeric compounds are therefore referred to, inter alia, as “partially defunctionalized amino resins”.
Low molecular mass and oligomeric compounds containing lateral and/or terminal carbamate (—HN—C(O)—O—R—O—C(O)—NH
2
) groups are described in the patents U.S. Pat. No. 5,336,566 and EP-A-0 622 387. These compounds are prepared from polyisocyanates and hydroxyalkyl carbamates. In particular, they enter into crosslinking reactions with amino resins.
An object of the present invention is to find new oligomeric and high molecular mass reaction products and low molecular mass, oligomeric and high molecular mass compounds which offer an alternative to the existing low molecular mass, oligomeric and high molecular mass reaction products and/or compounds containing lateral and/or terminal carbamate groups and which possess a higher reactivity than these products and compounds while having at least the same advantageous properties as them. The new oligomeric reaction products and/or the new low molecular mass and oligomeric compounds are to be suitable for use as new advantageous crosslinkers, and the new oligomeric and high molecular mass reaction products and the new oligomeric and high molecular mass compounds are to be suitable for use as new advantageous binders for coating compositions, adhesives and sealing compounds, or for the production of films.
A further object of the present invention is to provide new coating compositions, adhesives, sealing compounds and film precursors which have a new crosslinking chemistry and offer an advantageous alternative to the existing systems.
Yet another object of the present invention is to find new, simple and elegant processes for preparing the new oligomeric and high molecular mass reaction products and/or the new low molecular mass, oligomeric and high molecular mass compounds.
We have found, accordingly, the novel oligomeric and high molecular mass products of reaction of allophanic esters with nucleophilic compounds and also the novel low molecular mass, oligomeric and high molecular mass compounds containing lateral and/or terminal allophanate groups.
We have also found the novel coating compositions, films, adhesives and sealing compounds which comprise the novel low molecular mass, oligomeric and/or high molecular mass products of reaction of allophanic esters of nucleophilic compounds and/or the novel low molecular mass, oligomeric and/or high molecular mass compounds containing lateral and/or terminal allophanate groups.
Furthermore, we have found
A) a novel process for preparing the novel oligomeric and high molecular mass products of reaction of allophanic esters with nucleophilic compounds and/or the novel oligomeric and high molecular mass compounds containing lateral and/or terminal allophanate groups by transallophanatization of hydroxyl-containing oligomers and/or polymers (nucleophiles) with alkyl and aryl allophanates,
B) a novel process for preparing the novel low molecular mass and oligomeric compounds by reacting amino resins with alkyl and aryl allophanates, and
C) another novel process for preparing other novel low molecular mass and oligomeric compounds by reacting polyisocyanates with hydroxyalkyl allophanates.
In the light of the prior art, it was surprising and unforeseeable that the object on which the invention was based might be achieved with the aid of allophanates of the general formula I and allophanate groups of the general formulae II, III and IV:
R—O—C(O)—NH—C(O)—NH2 (I)
—O—C(O)—NH—C(O)—NH
2
(II)
—CH
2
—NH—C(O)—NH—C(O)—OR
1
(III)
—O—R
2
—O—C(O)—NH—C(O)—NH
2
(IV)
In the general formula III, the radical R
1
denotes
an alkyl or cycloalkyl group, in particular a C
1
to C
10
alkyl group or a C
5
to C
10
cycloalkyl group; examples of suitable such groups for use in accordance with the invention are methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, n-hexyl, 2-methylhexyl, n-heptyl, 2-ethylhexyl, n-octyl, isooctyl, n-nonyl, n-decyl, cyclopentyl, cyclohexyl, cycloheptyl, indenyl or decalinyl radicals;
an aryl group, in particular a phenyl group;
one of the aforementioned radicals containing essentially inert groups which do not react with crosslinking agents or binders; examples of suitable such groups are halogen atoms such as chlorine or fluorine atoms, aromatic radicals, nitro groups or alkyl or aryl ether groups; and also
one of the aforementioned groups which have at least one free hydroxyl group, especially those derived from low molecular mass, linear or branched polyols or from cycloaliphatic polyols; examples of suitable polyols are neo-alcohols, butylethyl-1,3-propanediol, 2-methyl-1,3-propane-diol, 1,6-hexeanediol, 1,8-octanediol, 2,4-diethyl-1,3-octanediol, 2-ethyl-1,3-hexanediol, 1,4-di-methylolcyclohexane, trimethylolpropane, glycerol, diglycerol, polyglycerol, pentaerythritol, dipentaerythritol or homopentaerythritol.
In the general formula IV, the radical R
2
denotes
linear or branched alkanediyl radicals or cycloalkanediyl radicals, especially methylene, ethylene, propylene-1,2-, tetramethylene, penta-methylene, hexamethylene, heptamethylene, cyclo-hexane-1,3-, -1,2- or -1,4-diyl, butylethyl-propane-1,3-diyl, 2-methylpropane-1,3-diyl, 2,4-diethylocta
Jung Werner
Rink Heinz-Peter
Röckrath Ulrike
Savino Thomas
BASF Coatings AG
Gorr Rachel
LandOfFree
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