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Production of uretdione polyisocyanates

A technology of isocyanate and pyridine, applied in the field of preparing polyisocyanates with high content of uretdione groups, can solve problems such as difficulty in use

Inactive Publication Date: 2009-06-10
COVESTRO DEUTSCHLAND AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] However, all phosphines share the common disadvantage of being air-sensitive, which makes their industrial use more difficult

Method used

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  • Production of uretdione polyisocyanates
  • Production of uretdione polyisocyanates
  • Production of uretdione polyisocyanates

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1 and 2, and comparative Embodiment 3 and 4

[0082] In a glass vessel closed by a septum, in the presence of 2 mol % of catalyst (III) (Examples 1 and 2) or N,N,-dimethylaminopyridine (DMAP) (Examples 3 and 4), under nitrogen At 23° C., 10 g of freshly degassed HDI (Examples 1 and 3) or IPDI (Examples 2 and 4) were stirred in each case using a magnetic stir bar at regular intervals by stirring the reaction mixture Refractive index (at 20°C, the optical frequency of the D line of the sodium spectrum: n D 20) were measured (see Table 1) to check the progress of the reaction. After 135 minutes, the reaction mixture was analyzed by NMR spectroscopy. After 24 hours, the reaction mixtures from Examples 1 and 2 had become very viscous and could no longer be stirred with a magnetic stir bar, whereas those from Examples 3 and 4 could still be stirred stably. The behavior of the mixtures from Examples 3 and 4 shows a significantly higher activity of the catalyst according to the invention compared to the prior art catalyst (DMA...

Embodiment 5

[0086] Catalyst: (III) (0.24 mol%, based on HDI); reaction temperature: 40°C.

[0087] 400 ml of HDI was placed in a double-walled flanged vessel, maintained at 40°C by an external circuit, equipped with a stirrer and reflux condenser, connected to an inert gas unit (nitrogen / vacuum) and a thermometer , and degassed. After flushing with nitrogen, 1.5 g of Catalyst III were added and the mixture was stirred at 40° C. for the time indicated in Table 2. The refractive index (n D 20 ) rose to 1.4760. The reaction mixture was subsequently worked up without prior catalyst deactivation. The operation is carried out by means of vacuum distillation in a short path evaporator (SPE) type thin-film evaporator equipped with an upstream pre-evaporator (PV) (distillation data: pressure: 0.08 mbar, PV temperature: 140 °C, MV temperature: 150 °C , distillation time: 1 hour), the unreacted monomers were separated together with the active catalyst as a distillate, and the polyisocyanate res...

Embodiment 6

[0093] Catalyst: (IV) (0.2mol%, based on HDI); Reaction temperature: 40°C

[0094] The procedure of Example 5 was repeated, except that 450 ml of HDI and 0.9 g of catalyst of formula IV were used.

[0095] Table 3: Catalyst: (IV) (0.2mol%, based on HDI); Reaction temperature: 40°C, semi-continuous reaction process

[0096] Example 6

[0097] The structural composition of the resins in Examples 5 and 6 is the same. The resin is essentially pure HDI uretdione with >95 mol% uretdione structures while isocyanurate and iminooxadiazinedione structures make up <5% of the total.

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Abstract

The invention relates to preparation of uretdione polyisocyanates, in particular relates to the use of specific pyridines as catalysts for the dimerization of isocyanates (uretdione formation) and a process for preparing polyisocyanates having a high content of uretdione groups.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to German Patent Application No. 10 2007 059 859.0, filed December 12, 2007, based on 35 U.S.C. § 119(a)-(d). technical field [0003] The present invention relates to the use of specific pyridine derivatives as catalysts in the dimerization of isocyanates (to uretdiones) and to a process for the preparation of polyisocyanates having a high content of uretdione groups. Background technique [0004] Aliphatic polyisocyanates containing uretdione groups and based on optionally branched linear-aliphatic diisocyanates have particularly low viscosities. Products based on aromatic, araliphatic or cycloaliphatic diisocyanates are generally highly viscous to solid substances which can be used inter alia as elimination-free, internally blocked crosslinkers in coating systems . [0005] Isocyanate oligomerization is reviewed in J. Prakt. Chem. / Chem. Ztg. 1994, 336, 185-200. [0006] Tris(dial...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D229/00B01J31/02C08G18/02
CPCC08G18/798C07D471/04C07D229/00C08G18/027
Inventor F·里克特A·赫金R·哈尔帕普
Owner COVESTRO DEUTSCHLAND AG
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