Allophonate modified polyisocyanates

a technology of polyisocyanates and allophonates, applied in the field of polyisocyanates, can solve the problems of low nco functionality of aliphatic polyisocyanates containing uretdione groups, uretdione structure can be prone to scission under high temperature or aging, and within the coating

Inactive Publication Date: 2006-10-05
BAYER MATERIALSCIENCE AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

"The present invention is about a composition that includes certain compounds with isocyanate groups. These compounds have a low average NCO functionality (less than or equal to 3.5) and a small amount of allophanate groups (between 1.5 and 8% by weight). The composition is also free of uretdione groups. The invention also provides a two-component elastomeric coating composition that includes a component A with the described compounds and a component B with reactive functional groups. The invention also includes a process for coating a substrate by contacting it with the described composition. The technical effect of this invention is to provide a composition with improved properties that can be used in various applications such as coating substrates."

Problems solved by technology

Many elastomeric coatings utilize aliphatic polyisocyanates containing uretdione groups with low NCO functionality because of their desirably low viscosity.
However, the uretdione structure can be prone to scission under high temperatures or aging, reforming monomeric isocyanates and liberating carbon dioxide.
This causes many problems within the coating, including blistering and lower tensile strength.

Method used

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  • Allophonate modified polyisocyanates
  • Allophonate modified polyisocyanates
  • Allophonate modified polyisocyanates

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0064] Hexamethylene diisocyanate (HDI, DESMODUR® H, Bayer Materials Science, LLC, Pittsburgh, Pa.) was charged to a reactor and heated to 105° C. under a nitrogen sparge. At 105° C. a mixture of 67 g n-butanol, 55 g 1-propanol, and 60 g 1-pentanol was fed to the reactor over a 30-minute period. The mix was maintained at 105° C. for 30 minutes and then heated to 115° C. at which time 2.5 g of a 10% zinc octoate solution was added over a 1-hour period. After a 30-minute hold period, the temperature was increased to 120° C. for two hours when 0.27 g p-toluene sulfonic acid was added to the reactor and the product was stripped in TFE at 140° C. at less than 300 mTorr until all volatiles were removed. The 100% solids product had 19.4 wt. % NCO groups and a viscosity of 382 cps at 25° C. at a shear rate of 200 sec−1 and 0.08 wt. % HDI monomer. Gel permeation chromatography using polystyrene standards indicated that the HDI allophanate trimer product had a number average molecular weight ...

examples 2 and 3

[0065] Polyurethanes were prepared by combining DESMOPHEN® VP LS 2328 (polyester polyol, Bayer Materials Science) and the compound of Example 1 (Example 2) and DESMODUR® N-3400 (prior art, polyisocyanate based on HDI and containing uretdione groups, Bayer Materials Science, Example 3) at a 1:1 NCO:OH equivalent ratio, pouring the mixture into a casting plaque and allowing the composition to fully cure. The compositions were cured at standard conditions of 20° C., 50% relative humidity for at least two weeks before testing. Tensile strength and percent elongation were determined according to ASTM D-412. Split and Die “C” tear strengths were determined according to ASTM D-624. The resulting films had the following properties:

TensileElongationExampleStrength(%)Split TearDie C Tear2397.4144.47.741.23181.8 87.16.534.6Improvement119%66%18%19%

[0066] The percent improvement values indicate the superior tensile and tear properties of polyurethanes prepared using the isocyanate containing c...

examples 4 and 5

[0067] Polyurethanes were prepared by combining DESMOPHEN® VP LS 2328 (polyester polyol, Bayer Materials Science) and a 50 / 50 w / w mixture of the compound of Example 1 and DESMODUR® XP-7100N (polyfunctional isocyanate based on HDI, Bayer Materials Science; Example 4) and a 50 / 50 w / w mixture of DESMODUR® N-3400 and DESMODUR® XP-7100N (prior art, Example 5) at a 1:1 NCO:OH equivalent ratio, pouring the mixture into a casting plaque and allowing the composition to fully cure. The compositions were cured at standard conditions of 20° C., 50% relative humidity for at least two weeks before testing. Tensile strength and percent elongation were determined according to ASTM D-412. Split and Die “C” tear strengths were determined according to ASTM D-624. The resulting films had the following properties:

TensileElongationExampleStrength(%)Split TearDie C Tear4485.9119.56.7532.55281.1 84.35.4 29.7Improvement72.9%41.8%25%9%

[0068] The percent improvement values indicate the superior tensile and ...

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Abstract

A composition that includes isocyanate group containing compounds that include on average i) a NCO functionality less than or equal to 3.5; and ii) from 1.5 to 8 percent by weight, based on the isocyanate containing compound, of allophanate groups; and which is substantially free of uretdione groups. The composition can be used in two component elastomeric coating compositions that include a component A the above-described composition and a component B that includes a compound containing one or more functional groups that are reactive with isocyanate groups. The elastomeric coating compositions can be used to coat substrates.

Description

BACKGROUND OF THE INVENTION [0001] 1. Field of the Invention [0002] The present invention is directed to polyisocyanates and in particular to polyisocyanates useful in elastomeric coatings. [0003] 2. Description of the Prior Art [0004] Elastomeric coating compositions are often used to form a protective coating on a substrate. In many cases, the composition forms a protective coating on roofs, or a substrate provided by one or more components of an automotive vehicle. [0005] U.S. Pat. No. 6,613,389 discloses elastomeric coating compositions that include at least two components, a polyisocyanate component; and an amine component. [0006] U.S. Pat. No. 6,733,838 discloses fluorinated polyurethane elastomer coatings prepared by the reaction of a polyol in a base component with a polyisocyanate in the curing agent. [0007] Many elastomeric coatings utilize aliphatic polyisocyanates containing uretdione groups with low NCO functionality because of their desirably low viscosity. However, th...

Claims

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Application Information

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Patent Type & AuthorityApplications(United States)
IPC IPC(8): C08G18/00
CPCC08G18/222C09D175/06C08G18/7837C08G18/00C08G18/72C08G18/78
InventorZIELINSKI, DAVID P.SHAFFER, MYRONJEFFRIES, MICHAEL K.
OwnerBAYER MATERIALSCIENCE AG