EP-4737502-A1 - METHOD FOR PRODUCING POLYETHER COMPOUND, METHOD FOR PRODUCING POLYETHER COMPOUND HAVING REACTIVE SILICON GROUP, METHOD FOR PRODUCING POLYETHER COMPOUND HAVING URETHANE BOND, AND METHOD FOR PRODUCING POLYETHER COMPOUND HAVING POLYMERIZABLE UNSATURATED GROUP

Abstract

A method of producing a polyether compound containing a hydroxyl group according to the present invention includes polymerizing an AO in an AO-containing raw material with an initiator containing a hydroxyl group in a presence of a composite metal cyanide complex catalyst, in which a content of methyl formate in the AO-containing raw material is less than 20 ppm with respect to a total mass of the AO-containing raw material, a method of producing a polyether compound containing a reactive silicon group further includes converting a hydroxyl group of a polyether compound into a group containing a reactive silicon group, a method of producing a polyether compound having a urethane bond further includes reacting a polyether compound containing a hydroxyl group with a polyisocyanate, and a method of producing a polyether compound containing a polymerizable unsaturated group further includes converting a hydroxyl group of a polyether compound into a group containing a polymerizable unsaturated group.

Inventors

• TAKEDA, HAJIME
• ARAI, TAKEAKI
• KOGUCHI, RYOHEI

Assignees

• AGC INC.

Dates

Publication Date

20260506

Application Date

20250709

Claims (9)

1. A method of producing a polyether compound containing a hydroxyl group, the method comprising: bringing an initiator containing a hydroxyl group into contact with an alkylene oxide-containing raw material in a presence of a composite metal cyanide complex catalyst and polymerizing an alkylene oxide in the alkylene oxide-containing raw material with the initiator, wherein a content of methyl formate in the alkylene oxide-containing raw material is less than 20 ppm with respect to a total mass of the alkylene oxide-containing raw material.
2. The production method according to Claim 1, wherein a content of propionaldehyde in the alkylene oxide-containing raw material is less than 20 ppm.
3. The production method according to Claim 1 or 2, wherein the alkylene oxide-containing raw material contains an alkylene oxide having 3 or more carbon atoms.
4. The production method according to any one of Claims 1 to 3, wherein the number of hydroxyl groups in the initiator is 1 to 10.
5. The production method according to any one of Claims 1 to 4, wherein a molecular weight of the polyether compound containing the hydroxyl group in terms of hydroxyl value is 1,000 to 100,000.
6. The production method according to any one of Claims 1 to 5, wherein a slurry catalyst in which particles of the composite metal cyanide complex catalyst are dispersed in a dispersion medium is used.
7. A method of producing a polyether compound containing a reactive silicon group, the method comprising: converting a hydroxyl group of a polyether compound containing the hydroxyl group, which is obtained by the production method according to any one of Claims 1 to 6, into a group containing a reactive silicon group represented by Formula 1, -SiR a X 3-a Formula 1 in Formula 1, R represents a monovalent organic group having 1 to 20 carbon atoms, which is an organic group other than a hydrolyzable group, X represents a hydroxyl group, a halogen atom, or a hydrolyzable group, a represents an integer of 0 to 2, and R's are the same as or different from each other in a case where a represents 2, and X's are the same as or different from each other in a case where a represents 0 or 1.
8. A method of producing a polyether compound having a urethane bond, the method comprising: reacting a polyether compound containing a hydroxyl group, which is obtained by the production method according to any one of Claims 1 to 6, with a polyisocyanate.
9. A method of producing a polyether compound containing a polymerizable unsaturated group, the method comprising: converting a hydroxyl group of a polyether compound containing the hydroxyl group, which is obtained by the production method according to any one of Claims 1 to 6, into a group containing a polymerizable unsaturated group.

Description

TECHNICAL FIELD The present invention relates to a method of producing a polyether compound, a method of producing a polyether compound containing a reactive silicon group, a method of producing a polyether compound having a urethane bond, and a method of producing a polyether compound containing a polymerizable unsaturated group. BACKGROUND ART A polyether compound is used as a raw material for an adhesive, a coating material, a sealant, and the like. The polyether compound is produced by polymerizing an alkylene oxide with an initiator having active hydrogen. As a polymerization catalyst for obtaining a polyether compound having a narrow molecular weight distribution, a composite metal cyanide complex catalyst is known. Patent Document 1 discloses a method of producing hydrolyzable silyl group-containing polyoxyalkylene, including a step of performing ring-opening polymerization on a monoepoxide having a moisture content of 5 ppm or greater and less than 50 ppm to obtain hydroxyl group-containing polyoxyalkylene and a step of introducing a hydrolyzable silyl group into the hydroxyl group-containing polyoxyalkylene. Patent Document 1 discloses that the hydrolyzable silyl group-containing polyoxyalkylene to be obtained can exhibit a high modulus after curing by using a monoepoxide having a low moisture content. It is known that the polyether compound containing a reactive silicon group has a property of being crosslinked by the formation of a siloxane bond accompanied by a hydrolysis reaction or the like of the reactive silicon group due to moisture or the like even at room temperature, and obtaining a rubber-like cured substance. Therefore, the polyether compound containing a reactive silicon group has already been industrially produced and is widely used for applications such as a sealing material or an adhesive. The polyether compound containing a reactive silicon group is produced using a polyether compound containing a hydroxyl group as a raw material. The polyether compound containing a hydroxyl group is produced by polymerizing an alkylene oxide with an initiator having active hydrogen. As a polymerization catalyst for obtaining a polyether compound having a small molecular weight distribution, a composite metal cyanide complex catalyst is known. A polyether compound having a urethane bond, such as a urethane prepolymer, is used as a raw material for an adhesive, a coating material, a sealant, a coating, and the like. The polyether compound having a urethane bond is produced using a polyether compound containing a hydroxyl group as a raw material. The polyether compound containing a hydroxyl group is produced by polymerizing an alkylene oxide with an initiator having active hydrogen. As a polymerization catalyst for obtaining a polyether compound having a small molecular weight distribution, a composite metal cyanide complex catalyst is known. Patent Document 2 discloses a urethane prepolymer composition (G) containing a urethane prepolymer (E) having a hydroxyl group terminal and a polyalkylene oxide (B). In addition, Patent Document 2 discloses that the urethane prepolymer (E) is a reactant of a polyol and a polyisocyanate (C), and contains at least one urethane group and at least one hydroxyl group in one molecule. Further, Patent Document 2 also discloses that the polyol can be produced by a composite metal cyanide complex catalyst. A polyether compound containing a polymerizable unsaturated group is used as a raw material for a pressure sensitive adhesive or the like in the fields of optical component materials, liquid crystal panels, and the like (for example, Patent Document 3). The polyether compound containing a polymerizable unsaturated group is produced using a polyether compound containing a hydroxyl group as a raw material. The polyether compound containing a hydroxyl group is produced by polymerizing an alkylene oxide with an initiator having active hydrogen. As a polymerization catalyst for obtaining a polyether compound having a narrow molecular weight distribution, a composite metal cyanide complex catalyst is known. Citation List Patent Documents Patent Document 1: PCT International Publication No. WO2023/095636Patent Document 2: Japanese Unexamined Patent Application, First Publication No. 2023-155601Patent Document 3: Japanese Unexamined Patent Application, First Publication No. 2012-126839 SUMMARY OF INVENTION Technical Problem However, according to the examination conducted by the present inventors, in a case where a complex metal cyanide compound complex catalyst is used, an ultrahigh-molecular-weight component of a polyether compound to be obtained is excessively produced in some cases. The ultrahigh-molecular-weight component disturbs the uniformity of the distance between crosslinking points during curing, and thus the strength of the cured substance may be decreased. An object of the present invention is to provide a method of producing a polyether compound, in which the am