Composition and cured product thereof

Patent metadata

Field	Value
Publication number	US-12528970-B2
Application number	US-202017760903-A
Country	US
Kind code	B2
Filing date	Sep 8, 2020
Priority date	Sep 17, 2019
Publication date	Jan 20, 2026
Grant date	Jan 20, 2026

Abstract

Provided is a composition capable of forming a cured product excelling in adhesion to a substrate, hardness, scratch resistance, and chemical resistance. The composition of the present disclosure contains a polyol compound (A) and an isocyanate compound (B). The polyol compound (A) includes a compound (a1) represented by Formula (1) below, where R 1 to R 3 each are a group represented by Formula (1a), the compound (a1) having a number average molecular weight (calibrated with polystyrene standard) of 800 or greater. The isocyanate compound (B) includes a polyisocyanate compound having an isocyanurate skeleton.

First claim

The invention claimed is:

1 . A composition comprising:
a polyol compound (A); and an isocyanate compound (B), wherein the polyol compound (A) comprises a compound (a1) represented by Formula (1):

wherein R 1 to R 3 are each, identically or differently, a group represented by Formula (1a):

wherein L 1 and L 2 are each, identically or differently, an alkylene group having from 1 to 10 carbons, m is a number of 0 or greater, and the bond with the wavy line bonds to a nitrogen atom in Formula (1), provided that “m”s in the groups represented by Formula (1a) in R 1 , R 2 , and R 3 are not simultaneously 0, and
wherein the compound (a1) has a number average molecular weight, calibrated with polystyrene standard, of 800 or greater, and
wherein the isocyanate compound (B) comprises a compound (b) represented by Formula (2):

wherein L 3 , L 4 , and L 5 are each, identically or differently, a hydrogen atom, an alkyl group having from 1 to 10 carbons and having an NCO group, or an alkyl group having from 1 to 10 carbons and having a group represented by Formula (2a):

wherein L 6 and L 7 are each, identically or differently, an alkylene group having from 1 to 10 carbons, and the bond with the wavy line bonds to a carbon atom configuring the alkyl group, provided that L 3 , L 4 , and L 5 are not simultaneously hydrogen atoms,
wherein a hydroxyl value of the compound (a1) is from 140 to 210 (KOH mg/g), and
wherein the polyol compound (A) further comprises a polyester polyol (a2) having a number average molecular weight, calibrated with polystyrene standard, from 200 to 600, and a hydroxyl value from 300 to 850 (KOH mg/g), and in an amount ranging from 0.5 to 1.5 parts by weight per 1 part by weight of the compound (a1).

2 . The composition according to claim 1 , wherein an equivalent ratio (NCO/OH) of the NCO groups of the isocyanate compound (B) to the OH groups of the polyol compound (A) in the composition is in a range from 0.2 to 2.0.

3 . The composition according to claim 1 , further comprising a polysiloxane derivative (C) in an amount from 0.1 to 0.5 part by weight per 100 parts by weight of the totality of the polyol compound (A) and the isocyanate compound (B).

4 . The composition according to claim 1 , further comprising a solvent represented by Formula (3):

wherein R 4 and R 6 are each, identically or differently, a hydrogen atom or an alkyl group having from 1 to 5 carbons, R 5 denotes an alkylene group having from 1 to 5 carbons, s denotes an integer of 1 or greater, t is 0 or 1, and when s is an integer of 2 or greater, R 5 s may be the same or different.

5 . The composition according to claim 1 , wherein the composition is a coating agent.

6 . A cured product of the composition described in claim 1 .

7 . A coating film-attached plastic molded article comprising:
a plastic molded article; and a coating film covering at least part of a surface of the plastic molded article, the coating film comprising the cured product described in claim 6 .

8 . The composition according to claim 1 , wherein the NCO content of compound (b) is from 17 to 25 wt. %.

9 . The composition according to claim 1 , wherein a total content of the compound (a1) and the polyester polyol (a2) is 60 wt. % or greater of the total amount of the polyol compound (A) contained in the composition.

10 . The composition according to claim 1 , wherein the content of the compound (b) is 60 wt. % or greater of the total amount of the isocyanate compound (B) contained in the composition.

11 . A method for manufacturing a coating agent, the method including mixing a polyol compound (A); and
an isocyanate compound (B), wherein the polyol compound (A) comprises a compound (a1) represented by Formula (1):

wherein R 1 to R 3 are each, identically or differently, a group represented by Formula (1a):

wherein L 1 and L 2 are each, identically or differently, an alkylene group having from 1 to 10 carbons, m is a number of 0 or greater, and the bond with the wavy line bonds to a nitrogen atom in Formula (1), provided that “m”s in the groups represented by Formula (1a) in R 1 , R 2 , and R 3 are not simultaneously 0, and
wherein the compound (a1) has a number average molecular weight, calibrated with polystyrene standard, of 800 or greater, and
wherein the isocyanate compound (B) comprises a compound (b) represented by Formula (2):

wherein L 3 , L 4 , and L 5 are each, identically or differently, a hydrogen atom, an alkyl group having from 1 to 10 carbons and having an NCO group, or an alkyl group having from 1 to 10 carbons and having a group represented by Formula (2a):

wherein L 6 and L 7 are each, identically or differently, an alkylene group having from 1 to 10 carbons, and the bond with the wavy line bonds to a carbon atom configuring the alkyl group, provided that L 3 , L 4 , and L 5 are not simultaneously hydrogen atoms,
wherein a hydroxyl value of the compound (a1) is from 140 to 210 (KOH mg/g), and
wherein the polyol compound (A) further comprises a polyester polyol (a2) having a number average molecular weight, calibrated with polystyrene standard, from 200 to 600, and a hydroxyl value from 300 to 850 (KOH mg/g), and in an amount ranging from 0.5 to 1.5 parts by weight per 1 part by weight of the compound (a1).

12 . A method for manufacturing a coating film-attached plastic molded article, the method including coating the surface of a plastic molded article with the composition described in claim 1 , thereby manufacturing a coating film-attached plastic molded article in which at least part of the surface of the plastic molded article is covered with a coating film formed from a cured product of the composition.

Assignees

• Daicel Corp

Inventors

• Konno Takashi
• Maetsu Naritoshi
• Watanabe Jun
• Hatanaka Shintarou

Classifications

• C08J2475/04

  Polyurethanes · CPC title

• C08J2367/02

  Polyesters derived from dicarboxylic acids and dihydroxy compounds; (C08J2367/06 takes precedence) · CPC title

• C08G18/792

  formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates · CPC title

• C08G18/34

  Carboxylic acids; Esters thereof with monohydroxyl compounds · CPC title

• C08G18/244

  tin salts of carboxylic acids · CPC title