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Compounds having isocyanate functional group substituents and coating compositions comprised thereof

A cyanate-functional, isocyanate-based technology for metal substrates, paint or varnish type coatings

Active Publication Date: 2013-01-23
VENCOREX FRANCE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In addition, too rapid exposure of these coatings to humid conditions can lead to the appearance of whitish spots due to the reaction of unreacted isocyanate functional groups with water, which in turn leads to the need for touch-up here.

Method used

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  • Compounds having isocyanate functional group substituents and coating compositions comprised thereof
  • Compounds having isocyanate functional group substituents and coating compositions comprised thereof
  • Compounds having isocyanate functional group substituents and coating compositions comprised thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0177] This example relates to the preparation of compounds of the invention having isocyanate functionality and additionally comprising urethane functionality.

[0178] 450.5 g Tolonate HDT LV2, 48.5 g HBPA (0.203 mol) and 111.8 g n-butyl acetate were continuously fed into the reactor under nitrogen flow. The NCO of the starting Tolonate HDT LV2 was detected to be 0.537 mol / 100 g. The HBPA / (HBPA+starting isocyanate) ratio was 9.72%.

[0179] The mixture was heated at 120°C for 3 hours. NCO detection changed from 0.537 mol / 100 g at the start of Tolonate HDT LV2 to 0.331 of the reaction mixture at the end of the reaction.

[0180] 610.8 g of a formulation of the compound of the invention at 82% solids in n-butyl acetate were recovered.

[0181] The NCO detection of the preparation of the compound of the present invention is 0.33 mol / 100g. For a solids content of 82% in n-butyl acetate, its viscosity at 25° C. is 1305 mPa·s.

[0182] The product was separated by gel permeat...

Embodiment 2 and 3

[0186] These examples relate to the preparation of compounds of the invention having isocyanate functionality and additionally comprising urethane functionality.

[0187] The preparation was carried out as in Example 1, but the operating conditions and the HBPA / (HBPA+starting isocyanate) ratio were varied. The results are shown in Table 1 below.

[0188] Table 1

[0189]

[0190] Q1: Quantity of Tolonate HDT LV2

[0191] Q2: The amount of HBPA

[0192] R: HBPA / (HBPA+HDT LV2) weight ratio

[0193] T: reaction temperature; t: reaction time

[0194] ES: solid content

[0195] Ti: NCO detection, in mol / 100g

[0196] Ta: Residual HDI monomer level

Embodiment 4

[0198] This example relates to the preparation of compounds of the invention having isocyanate functionality and additionally comprising allophanate functionality.

[0199] 372.4 g of Tolonate HDT LV2 and 27.4 g of HBPA (0.114 mol) were continuously fed into the reactor under nitrogen flow. Dibutyltin dilaurate was added at 200 ppm relative to Tolonate HDT LV2. The NCO detection of the starting Tolonate HDT LV2 was 0.55 mol / 100 g. The HBPA / (HBPA+starting isocyanate) weight ratio was 6.85%.

[0200] The mixture was heated at 110°C for 48 hours. The NCO detection of the reaction mixture at the end of the reaction was 0.377 mol / 100 g.

[0201] 400 g of product were recovered.

[0202] The NCO assay of the formulation of the compound of the invention with allophanate functionality was 0.377 mol / 100 g. Its viscosity at 25°C and 90% solid content in n-butyl acetate is 14000mPa·s, and for 70% solid content in n-butyl acetate, its viscosity at 25°C is 800mPa·s.

[0203] The prod...

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Abstract

The compound of the invention, having an average isocyanate functionality of greater than 2, results from the reaction of a (poly)isocyanate having an average functionality of greater than 2, with the compound X comprising a function B(H)n or B'(H)n' where n is equal to 1 or 2, n' is equal to 1, 2 or 3, H is a labile hydrogen and B denotes O, S, N, N being a primary or secondary nitrogen, -C(=O)-O, -C(=O)-N, or else the groups O=P(O)2; O=P(O)OR1; O=P(O)3; O=P(O)2 OR1; O=P(O)-OR1, R1 denoting an alkyl or aralkyl radical, and B' denotes -SiR2R3R4, R2, R3 and R4 representing oxygen, an alkyl radical bearing a function that is reacted with the (poly)isocyanate, or an aralkyl, aryl, -O-alkyl or -O-aralkyl radical, X being, in addition, a cycloaliphatic, aromatic or heterocyclic compound or a particle of a crosslinked polymer; and with the proviso that, when B denotes a secondary nitrogen and X is a cycloaliphatic compound, X is then a compound having at least two rings; the reaction being carried out with a compound X / [compound X + (poly)isocyanate] weight ratio of at most 50%. The invention also relates to a composition of the hardener type which comprises at least one compound of the above type. The compound or the composition of the invention can be used in the preparation of a coating of the paint or varnish type.

Description

[0001] This application is a divisional application of the Chinese patent application "Compounds with Isocyanate Functionality, Its Preparation and Use in Coating Preparation Method" with the filing date of November 28, 2006 and the application number of 200680051675.2. technical field [0002] The present invention relates to compounds having isocyanate functionality, to their preparation and to their use in processes for the production of coatings, in particular of the paint or varnish type, and especially for metal substrates. Background technique [0003] The automotive and aerospace industries are increasingly demanding technically very advanced coating compositions with improved conditions of use leading to high-quality finished products. [0004] Such compositions include polyurethane formulations comprising two components, one of which is a curing agent of polyisocyanate type and the other is a resin of polyol type which additionally contains the additives necessary f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6521C07D251/32C08G18/78C08G18/79C08G18/32C08G18/30C09D175/04
CPCC08G18/3885C09D175/04C08G18/7843C08G18/3212C08G18/7837C08G18/8016C08G18/792C08G18/776C07F9/65211C08G18/771C07F9/6521C07D251/34C08G18/38
Inventor J-M·贝尔纳P·巴尔博P·奥利尔
Owner VENCOREX FRANCE
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