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Ultraviolet light curing urethane acrylate composition, thin-film formed body, optical film, and method for manufacturing thin-film formed body

A kind of technology of ester acrylate, urethane

Active Publication Date: 2014-10-15
DAINIPPON INK & CHEM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0027] The object of the present invention is to provide an ultraviolet curable urethane acrylate composition that can be used in optical applications (such as films, sheets, fibers, coating materials, etc.) that require especially high-quality transparency. The method for producing a film molded article, an optical film, and a film molded article of the composition, the above-mentioned ultraviolet curable urethane acrylate composition does not have the following problem: migration of unreacted or decomposed products of the photopolymerization initiator ( Diffusion transfer) to the surface of the coating film or the surface of the molded product, contaminating the object in contact with the coating film or molded product when the coating film or molded product is laminated; or in the packaging field of food or pharmaceuticals, the above-mentioned unreacted substances or decomposition The substance becomes an impurity that should be removed; or the decomposed photopolymerization initiator changes into a yellow substance when recombined, which deteriorates the yellowness of the cured product

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0133] Hereinafter, the present invention will be described more specifically using examples, but the scope of the present invention is not limited to these examples.

[0134] In addition, in the present invention, unless otherwise specified, "parts" are "parts by mass" and "%" are "mass%".

[0135] In addition, the measurement method and evaluation method used in this invention are as follows.

[0136] [Method for measuring isocyanate equivalent of isocyanate group-terminated urethane prepolymer (C)]

[0137] The isocyanate equivalent (unit: g / mol) of the isocyanate group-terminated urethane prepolymer (C) used in the present invention is a value measured in accordance with JIS K7103.

[0138] Specifically, a sample of the urethane prepolymer (C) is accurately weighed in an Erlenmeyer flask, dissolved in dry toluene, 10 ml of di-n-butylamine solution is added, and the sample is uniformized and then left to stand. Using bromocresol green as an indicator, neutralize titration with a sta...

Synthetic example 1

[0164] "Synthesis of Urethane Acrylate Oligomer (E1)"

[0165] In the reaction vessel, as a polyol (A) having no aromatic skeleton, polyoxytetramethylene glycol (trade name: PTMG-1000, manufactured by Mitsubishi Chemical Corporation, Mn is 1000) 114 parts by mass, start stirring.

[0166] Next, as a polyisocyanate (B) having no aromatic skeleton, 4,4'-dicyclohexylmethane diisocyanate (hereinafter, abbreviated as "H 12 MDI".) 100 parts by mass, after raising the internal temperature to 85°C while paying attention to heat dissipation, stirring was performed for 3 hours while maintaining the temperature to obtain a urethane prepolymer (C) having an isocyanate group at the molecular end.

[0167] Furthermore, 62 parts by mass of 2-hydroxyethyl acrylate as a (meth)acrylic compound (D) having a hydroxyl group was slowly added while paying attention to heat dissipation, and stirred at 85°C for 2 hours to obtain a urethane acrylate oligomer 物(E1).

Synthetic example 2～6

[0169] "Synthesis of Urethane Acrylate Oligomers (E2)~(E6)"

[0170] As shown in Table 1, the polyol (A), the polyisocyanate (B), and the (meth)acrylic compound (D) having a hydroxyl group used were changed in their respective types and usage amounts. In addition to this, the same as in Synthesis Example 1 The same reaction conditions gave urethane acrylate oligomers (E2) to (E6).

[0171] [Table 1]

[0172] Table 1

Synthesis example 1

Synthesis Example 2

Synthesis Example 3

Synthesis Example 4

Synthesis Example 5

Synthesis Example 6

Synthetic raw material of urethane acrylate oligomer (E) (parts by mass)

(E1)

(E2)

(E3)

(E4)

(E5)

(E6)

PTMG-1000

114

81

114

114

114

123

2-hydroxyethyl acrylate

62

71

65

4-hydroxybutyl acrylate

87

2-hydroxyethyl acrylate

70

Pentaerythritol triacrylate

185

Pentaerythritol tetraacrylate

79

H 12 MDI

100

100

100

100

IPDI

100

MDI

100

[0173] It should be note...

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PUM

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Abstract

Provided is an ultraviolet light curing urethane acrylate composition with excellent ultraviolet light curing properties without containing a photo polymerization initiator, and that can be used for optical applications that require high transparency. The present invention is an ultraviolet light curing urethane acrylate composition containing (E) a urethane acrylate oligomer having a (meth)acryloyl group on the terminal of a molecule obtained by addition reaction of (D) a (meth)acrylate compound having a hydroxide group to (C) a urethane polymer having an isocyanate group on the terminal of a molecule obtained by reacting (A) a polyol that does not have an aromatic backbone and (B) a polyisocyanate that does not have an aromatic backbone; wherein the composition further contains 0.2 to 80 mass% of (F) at least one type of organic solvent that does not have an aromatic backbone, selected from the group consisting of ketone solvents, amide solvents, and alkyl halide solvents; and wherein the composition does not contain a photo polymerization initiator.

Description

Technical field [0001] The present invention relates to an ultraviolet curable urethane acrylate composition, a thin film molded body using the same, an optical film, and a method for producing a thin film molded body. [0002] In more detail, the present invention is different from the conventional ultraviolet curable resin composition, does not contain a photopolymerization initiator at all, and contains a specific organic solvent as a diluting solvent, which is cured rapidly by ultraviolet radiation, and can suppress the gain. A UV-curable urethane acrylate composition that exhibits excellent coatability or moldability and other properties such as yellowing of the cured product over time, no pollution to the contacted product, and film formed body using the composition (E.g., sheet, film), optical film, and method of manufacturing a thin film molded body. Background technique [0003] Conventionally, photocurable resins that can be cured by irradiation with active energy rays s...

Claims

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Application Information

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IPC IPC(8): C08F299/06C08J5/18
CPCC08G18/4854C08J7/04C08G18/10C08G18/672C08F299/065
Inventor 樋口大地坂元保
Owner DAINIPPON INK & CHEM INC
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