Moisture curable polydisulfides

A polydisulfide, moisture curing technology, applied in the field of polydisulfide, can solve the problems of short tank life and toxicity

Inactive Publication Date: 2012-06-13
HENKEL CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the relatively short pot life of these compositions, they are often available as two-component systems
Furthermore, these oxidizing agents are reactive and often toxic

Method used

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  • Moisture curable polydisulfides
  • Moisture curable polydisulfides
  • Moisture curable polydisulfides

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example

[0093] In each of the following synthesis examples, liquid polysulfide materials purchased from LP North America Distribution were used, and the specifications as received are shown in Table 1. The thiol equivalent weight was determined by potentiometric titration.

[0094] Table 1: Specifications of Liquid Polydisulfide

[0095]

[0096] Source: Technical Data Sheet from LP North America Distribution, Inc.

[0097] * Determined by potentiometric titration (Na 2 the s 2 o 3 / I 2 )

[0098] The general branched structures of these polydisulfides are shown below. LP 55 was prepared without branching agent, which has a linear di-telechelic structure. It can be used to prepare chain-extended linear polymers by reaction with other difunctional compounds.

[0099]

[0100] Trimercapto Capcure and trimethylolpropane-tris(3-mercapto-propionate) were supplied by Sigma Aldrich and Cognis, respectively. Vinyltrimethoxysilane and allyltrimethoxysilane purchased from Sigma ...

Embodiment 1

[0102] Example 1 : Reaction of polydisulfide LP-3 and vinyltrimethoxysilane via radical mercapto-ene addition

[0103]

[0104] To a 100-mL three-necked reaction flask equipped with a magnetic stirrer, thermocouple, and nitrogen inlet was added 183.7 g (0.18 mole) of polydisulfide LP-3 with a thiol equivalent weight of 510 g / eq and 53.3 g (0.36 mole) of vinyltrimethoxysilane.

[0105] The mixture was stirred to obtain a homogeneous solution, 2.7 g (0.008 mole) of 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile) ("V-70") was added and dissolved. The headspace was flushed with nitrogen and the solution was heated to 60°C during which time bubbling nitrogen gas was formed due to the decomposition of the azonitrile initiator. Aliquots of the mixture were removed periodically and analyzed for unreacted vinyl by infrared spectroscopy. After 6 hours, the vinyl was completely consumed. The reaction mixture was cooled to give the product α,ω-bis(trimethoxysilane) functional pol...

Embodiment 2

[0110] Example 2 : Reaction of polydisulfide LP-3 and allyltrimethoxysilane via radical mercapto-ene addition

[0111]

[0112] To a three-necked 300-mL reaction flask equipped with a nitrogen headspace purge, magnetic stirrer, heating mantle, and thermocouple was added 51.054 g (~0.05 mole) of polydisulfide LP-3 with a thiol equivalent weight of 510 g / eq. , 16.219 g (0.1 mole) of allyltrimethoxysilane and 0.681 g (2.21 mmole) of 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile). Stir the mixture and heat. At 45°C, a homogeneous pale yellow solution was formed, and at 50°C a strongly exothermic reaction occurred, driving the temperature to 85°C. The exothermic reaction ended with evolution of nitrogen. The mixture was cooled to 60°C and stirred for 5 hours, during which time gas evolution ceased. The mixture was cooled and the trimethoxysilane-functional polydisulfide was isolated in high yield.

[0113] The structure of the product was confirmed by spectroscopic analy...

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Abstract

Provided are polydisulfides that are useful in moisture curable sealants. The polydisulfides have an S-S link in the backbone and are end-capped with at least one alkoxysilane functional group. Also provided are methods of making the polydisulfides, including methods that do not require the presence of a catalyst.

Description

technical field [0001] The present invention relates to polydisulfides for use in moisture curable adhesive compositions capable of being cured by alkoxysilane groups to form high strength bonded articles. Background technique [0002] Alkoxysilylated polymers can be crosslinked by atmospheric moisture under ambient conditions. Compositions based on these types of polymers are often referred to as RTV sealants (or adhesives). The best known example is RTV silicone sealant. [0003] Flexible RTV moisture cure polymers are known in the art as useful adhesives, coatings, potting compounds and sealants. Silicone, Polyurethane, Silicone / Polyurethane, Silicone / Acrylic, just to name a few general categories that have been widely used. [0004] For example, US Patent No. 5,554,709 discloses moisture-curing alkoxysilane-functional polyurethanes and their use in adhesive and sealing compositions. US Patent No. 7,009,022 discloses moisture curable siloxy terminated ABA triblock cop...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G75/14C08L81/04C09K3/10C07F7/18
CPCC09K3/1012C08L81/04C07F7/1836C08G75/14C07F7/1804C08L81/00
Inventor J·G·伍兹A·F·雅各宾J·克莱因K·伊森比格尔
Owner HENKEL CORP
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