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Radiation- or thermally-curable oxetane barrier sealants

a technology of oxetane and barrier sealants, which is applied in the field of barrier sealants, adhesives, encapsulants, coatings, etc., can solve the problems of many systems that are merely hydrophobic not good barrier materials, and cannot be sufficient to have only a low solubility, and achieve the effect of superior barrier performan

Inactive Publication Date: 2006-10-05
HENKEL KGAA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0015] The inventors have discovered that certain resin and resin / filler systems provide superior barrier performance, particularly to moisture, through the incorporation of an oxetane resin and a cationic initiator into the barrier composition. The oxetane resin in general will have the structure which the oxetane compound has the structure: in which R1, R2, R3, R4, R5, R6 are selected from the group consisting hydrogen, and alkyl, haloalkyl, alkoxy, aryloxy, aryl, ester, thio-ester, and sulfide groups. Such barrier materials may be used alone or in combination with other curable resins and various fillers. The resulting compositions exhibit a commercially acceptable cure rate, a balance of high crosslink density and molecular packing (low permeant mobility / diffusivity term, D), hydrophobicity (low water solubility term, S), and adhesion (strong adhesive / substrate interfaces) to make them effective for use in sealing and encapsulating electronic, optoelectronic, and MEMS devices.

Problems solved by technology

It is not sufficient to have only a low solubility (S) term or only a low diffusivity (D) term in order to obtain high performance barrier materials.
Thus, many systems that are merely hydrophobic are not good barrier materials despite the fact that they exhibit low moisture solubility.

Method used

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  • Radiation- or thermally-curable oxetane barrier sealants
  • Radiation- or thermally-curable oxetane barrier sealants
  • Radiation- or thermally-curable oxetane barrier sealants

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of Oxetane, 3,3′-[1,3-Phenylenebis (Methyleneoxymethylene)]bis[3-Methyl-

[0028]

[0029] Into a 250 mL three-neck round bottom flask equipped with a reflux condenser, a mechanic stirrer were added 12.0 g NaOH (0.3 mol), 0.6 g n-Bu4N+Br− (0.0019 mol), 30.0 g 3-methyl-3-hydroxymethyl-oxetane (0.29 mol), 25.0 g α, α′-dibromo-m-xylene (0.095 mol), and 100 mL of toluene. The reaction was brought to 110° C. for 3.5 hours. The organic phase was collected by filtration and the solvents were removed. The light yellow crude product was redissolved in 200 mL of toluene and washed with deionized water three times. After drying over magnesium sulfate, the toluene solution was passed through a short column of neutral alumina to remove trace amount of the ammonium salt phase transfer catalyst. Finally, the solvents were removed with rotary evaporator and Kugelrohr and the sample was purified by distillation. 1H NMR (CDCl3): δ ppm 1.36 (6H), 3.56 (4H), 4.38-4.55 (8H), 4.60 (4H), 7.18-7.38 (4...

example 2

Synthesis of Oxetane, 3,3′-[1,4-Phenylenebis(Methyleneoxymethylene)]bis[3-Methyl-

[0030]

[0031] The reaction conditions of Example 1 were adopted except 25.0 g α, α′-dibromo-p-xylene (0.095 mol) was used instead of 25.0 g a,a′-dibromo-m-xylene (0.095 mol). 1H NMR (CDCl3): δ ppm 1.36 (6H), 3.55 (4H), 4.37-4.55 (8H), 4.59 (4H), 7.36 (4H)

example 3

Synthesis of Oxetane, 3,3′-[1,3-Phenylenebis(Methyleneoxymethylene)]bis[3-Ethyl-

[0032]

[0033] The reaction conditions of Example 1 were adopted except 34.1 g 3-ethyl-3-hydroxymethyl-oxetane (0.29 mol) was used instead of 30.0 g 3-methyl-3-hydroxymethyl-oxetane (0.29 mol). 1H NMR (CDCl3): δ ppm 0.87-0.91 (6H), 1.77-1.83 (4H), 3.61 (4H), 4.40-4.49 (8H), 4.59 (4H), 7.28-7.38 (4H).

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Abstract

This invention relates to cationically curable sealants that provide low moisture permeability and good adhesive strength after cure. The composition consists essentially of an oxetane compound and a cationic initiator.

Description

[0001] This Invention was made with support from the Government of the United States of America under Agreement No. MDA972-93-2-0014 awarded by the Army Research Laboratories. The Government has certain rights in the Invention.FIELD OF THE INVENTION [0002] This invention relates to barrier sealants, adhesives, encapsulants, and coatings for use in electronic and optoelectronic devices. (As used in this specification and claims, adhesives, sealants, encapsulants, and coatings are similar materials, all having adhesive, sealant, and coating properties and functions. When any one is recited, the others are deemed to be included.) BACKGROUND [0003] Radiation curable materials have found increased use as coatings, adhesives, and sealants over the past three decades for reasons including low energy consumption during cure, rapid cure speed through either radical or cationic mechanisms, low curing temperature, wide availability of curable materials, and the availability of solvent-free pro...

Claims

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Application Information

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IPC IPC(8): C08G59/06C08G59/08C08L63/00
CPCG03F7/038C08G65/18C08L71/00C08L63/00B01D69/00
Inventor KONG, SHENGQIAN
Owner HENKEL KGAA
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