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WO-2026094275-A1 - COMPOSITION CONTAINING POLYOXYALKYLENE (POLY)GLYCERIN-BASED ALKOXYSILANE

WO2026094275A1WO 2026094275 A1WO2026094275 A1WO 2026094275A1WO-2026094275-A1

Abstract

The purpose of the present invention is to provide a composition that makes it possible to obtain a cured coating film or a cured film which is resistant to water stains and oil stains while having flexibility when, for example, used for coating a substrate such as a film or produced as a film.　The problem has been solved by a composition containing: [A] a polyoxyalkylene (poly)glycerin-based alkoxysilane that has a skeleton in which polyoxyalkylene is condensed with (poly)glycerin having an average degree of polymerization of 1-100 and that has a plurality of alkoxysilyl groups at the terminals; [B] a silicate oligomer; and [C] a silicone-based leveling agent.

Inventors

  • MONDA Shizuki
  • KAKIKURA NOGUCHI Yuka
  • TANIHATA MIYAJI Yukiko
  • MATSUKAWA KIMIHIRO

Assignees

  • 阪本薬品工業株式会社

Dates

Publication Date
20260507
Application Date
20241112
Priority Date
20241101

Claims (7)

  1. [A] A polyoxyalkylene (poly)glycerol-based alkoxysilane having a skeleton in which polyoxyalkylene is condensed onto (poly)glycerol with an average degree of polymerization of 1 to 100, and having multiple alkoxysilyl groups at its terminals, [B] Silicate oligomers and [C] A composition characterized by containing a silicone-based leveling agent.
  2. The composition according to claim 1, characterized in that the [A] polyoxyalkylene (poly)glycerol-based alkoxysilane is a reaction product obtained by the reaction of a polyoxyalkylene (poly)glyceryl ether derivative obtained by condensing a polyoxyalkylene (poly)glyceryl ether having a hydroxyl group at one end or a compound having a first reactive functional group at one end with an alkoxysilane having a second reactive functional group at one end, wherein the product is obtained by the reaction of the hydroxyl group or the first reactive functional group with the second reactive functional group.
  3. The composition according to claim 2, characterized in that the polyoxyalkylene (poly)glyceryl ether or polyoxyalkylene (poly)glyceryl ether derivative described in claim 2 is represented by the structure of the following formula (1). (n, p, q, and r each represent the number of repeating units, where n is an integer from 1 to 100, and the sum of p, q, and r is an integer from 2 to 300. AO represents an alkylene oxide with 1 to 4 carbon atoms. X1 , X2 , and X3 are each substituents that independently contain hydrogen or a reactive functional group selected from the group consisting of a thiol group, (meth)acryloyl group, epoxy group, glycidyl group, or allyl group at their terminal end.)
  4. The composition according to claim 2 or 3, characterized in that the alkoxysilane having a second reactive functional group at its terminal end is one selected from the group consisting of a vinyl group, an isocyanate group, a thiol group, a (meth)acryloyl group, an epoxy group, a glycidyl group, a hydroxyl group, an amino group, and hydrogen.
  5. The composition according to claim 1 or 2, characterized in that the [B] silicate oligomer is at least one selected from a linear silicate oligomer, a branched silicate oligomer, or a cyclic silicate oligomer represented by the following formula (2). ( R1 and R2 are each independently hydrogen, a C1-C6 alkyl group, or a phenyl group, and m is an integer from 1 to 100. Y1 and Y2 are each independently hydrogen or a C1-C3 alkoxysilyl group.)
  6. The composition according to claim 1 or 2, characterized in that the [C] silicone-based leveling agent is a polysiloxane having a third reactive functional group selected from hydrogen, a hydroxyl group, an alkoxysilyl group, an amino group, a (meth)acryloyl group, an allyl group, an epoxy group, a carboxyl group, or a mercapto group at one end, both ends, or side chain, or a polysiloxane that does not have the third reactive functional group but has at least one alkyl group, a phenyl group, or hydrogen at its side chain.
  7. The composition according to claim 1 or 2, characterized in that the blending ratio of [A] polyoxyalkylene (poly)glycerin-based alkoxysilane and [B] silicate oligomer is [A] polyoxyalkylene (poly)glycerin-based alkoxysilane : [B] silicate oligomer = 20:80 to 70:30.

Description

Composition containing polyoxyalkylene (poly)glycerol-based alkoxysilane This invention relates to a composition containing polyoxyalkylene (poly)glycerin-based alkoxysilanes, etc., used for coating substrates, producing films, and the like. Flexible coatings are a promising technology with significant potential for future growth, particularly in applications for foldable displays such as those found in foldable smartphones. Flexible coatings utilize organic crosslinked polymers, inorganic crosslinked polymers, and organic-inorganic hybrid materials. Organic crosslinked polymers offer a high degree of freedom in molecular design, making them advantageous for imparting functionality, but they are less rigid than inorganic crosslinked polymers, posing a challenge in terms of durability. On the other hand, inorganic crosslinked polymers are suitable for durability, but it is difficult to impart functions related to softness, including flexibility. Therefore, to achieve more advanced flexible coatings, there is great expectation for organic-inorganic hybrid materials that combine the properties of both organic and inorganic polymers. For example, Patent Documents 1 and 2 disclose polyglycerin-based alkoxysilanes having a polyglycerin skeleton with alkoxysilyl groups at the terminals, obtained by reacting 3-isocyanatetopropyltriethoxysilane with an ethylene oxide adduct of polyglycerin, etc. It is disclosed that the cured coating films produced from these compounds possess sufficient flexibility despite containing inorganic components derived from alkoxysilyl groups. The compositions of the present invention will be described in detail below. While the embodiments described below are preferred examples for carrying out the present invention and therefore have various technical limitations, the present invention is not limited to these embodiments unless specifically stated in the following description. Furthermore, when the symbol "~" is used to indicate a range, it includes both an upper and lower limit to that range. The composition of the present invention contains [A] a polyoxyalkylene (poly)glycerin-based alkoxysilane having a skeleton in which polyoxyalkylene is condensed onto (poly)glycerin with an average degree of polymerization of 1 to 100, and having multiple alkoxysilyl groups at its terminals; [B] a silicate oligomer; and [C] a silicone-based leveling agent. [A] Polyoxyalkylene (poly)glycerol-based alkoxysilanes The polyoxyalkylene (poly)glycerin-based alkoxysilane of the present invention is a compound having a skeleton in which polyoxyalkylene is condensed onto (poly)glycerin with an average degree of polymerization of 1 to 100, and having multiple alkoxysilyl groups at its terminals. By using such a compound, sufficient flexibility and water repellency are imparted to the cured coating or cured film produced. Note that (poly)glycerin refers to at least one of glycerin or polyglycerin. In the polyoxyalkylene (poly)glycerin-based alkoxysilane of the present invention, the average degree of polymerization n of (poly)glycerin is preferably 1 to 100, more preferably 2 to 20, and most preferably 2 to 15. Here, the average degree of polymerization n can be calculated from the hydroxyl value by terminal analysis using the following formulas (α) and (β). The hydroxyl value in formula (β) is a numerical value that serves as an indicator of the magnitude of the number of hydroxyl groups contained in (poly)glycerin, and refers to the number of milligrams of potassium hydroxide required to neutralize the acetic acid necessary to acetylate the free hydroxyl groups contained in 1 g of (poly)glycerin. The number of milligrams of potassium hydroxide is calculated in accordance with the "Standard Methods for Analysis of Fats and Oils, 2013 Edition," edited by the Japan Oil Chemists' Society. Molecular weight=74n+18...(α) Hydroxyl value = 56110(n+2) / Molecular weight ... (β) The polyoxyalkylene (poly)glycerin-based alkoxysilane according to the present invention is preferably a reaction product obtained by the reaction of a polyoxyalkylene (poly)glyceryl ether derivative, which is obtained by condensing a polyoxyalkylene (poly)glyceryl ether having a hydroxyl group at one end or a compound having a first reactive functional group at one end, with an alkoxysilane having a second reactive functional group at one end. The polyoxyalkylene (poly)glyceryl ether or polyoxyalkylene (poly)glyceryl ether derivative is preferably a compound represented by the structure of the following formula (1). (n, p, q, and r each represent the number of repeating units, where n is an integer from 1 to 100, and the sum of p, q, and r is an integer from 2 to 300. AO represents an alkylene oxide with 1 to 4 carbon atoms. X1 , X2 , and X3 are each substituents that independently contain hydrogen or a reactive functional group selected from the group consisting of a thiol group, (meth)acryloyl group, epoxy group, glycidyl group, or allyl g