A polymerization catalyst for polythiourethanes, polymerizable liquid composition and process for the production of organic polythiourethane glass with a high refractive index

A technique for polymerizing catalysts and polymerizing compositions, which is applied in the fields of plexiglass, polymerizable liquid compositions, and organic polythiourethane glass, and can solve the problems of being unsuitable for industrial-scale production of optical products and inability to obtain polymerizable liquid compositions. Achieve good optical properties, improve toughness and impact strength, and good mold release

Active Publication Date: 2013-01-30
MITSUI CHEM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The fact that the mixing of these various components does not yield a polymerizable liquid composition, but prematur

Method used

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  • A polymerization catalyst for polythiourethanes, polymerizable liquid composition and process for the production of organic polythiourethane glass with a high refractive index
  • A polymerization catalyst for polythiourethanes, polymerizable liquid composition and process for the production of organic polythiourethane glass with a high refractive index
  • A polymerization catalyst for polythiourethanes, polymerizable liquid composition and process for the production of organic polythiourethane glass with a high refractive index

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0153] Composition No. 1 consisting of components (A), (B) and (C) in the amounts indicated in Table 1 was prepared according to the invention.

[0154] Component (A)

[0155] Component (A) consists of 4,4'-methylenebis(cyclohexylisocyanate).

[0156] Component (B)

[0157] Components obtained by mixing bis(3-mercaptopropionate)ethylene glycol and 2,3-bis((2-mercaptoethyl)thio)-1-propanethiol at 25°C and a pressure of 10 mbar (B).

[0158] Component (C)

[0159] Component (C) was obtained by mixing triethylamine and di(2-ethylhexyl)phosphate at 25°C.

[0160] Table 1

[0161]

[0162] Abbreviation

[0163] H12MDI=4,4'-methylene bis(cyclohexyl isocyanate)

[0164] GDMP = bis(3-mercaptopropionate) ethylene glycol

[0165] DMPT=2,3-bis((2-mercaptoethyl)thio)-1-propanethiol

[0166] TEA = triethylamine

[0167] Bis(2-EHP) = bis(2-ethylhexyl) phosphate

[0168] Casting (manual casting)

[0169] 1,500 g of component (A) and 9 g of previously prepared component...

Embodiment 2

[0182] According to the operation procedure of Example 1, compositions 2 to 5 of the present invention were prepared, which consisted of components (A), (B) and (C) in the amounts and conditions shown in Table 4.

[0183] Table 4

[0184]

[0185] The initial viscosity was measured on the degassed clear solution thus obtained, and then the viscosity at the same temperature was measured in successive times to obtain the values ​​shown in Table 5.

[0186] table 5

[0187]

[0188] The above data indicate a pot life of more than 2 hours in each case and are therefore suitable for the production of optical articles on an industrial scale by manual casting techniques.

[0189] The data presented in Table 5 also show how the stability of the inventive mixture can be varied by adjusting the catalyst concentration and the molar ratio between the two components of the catalyst.

[0190] The polymerizable compositions Nos. 2 to 4 thus obtained were poured into glass molds and p...

Embodiment 3

[0195]Composition No. 6 consisting of components (A), (B) and (C) in the amounts indicated in Table 7 was prepared according to the invention.

[0196] Component (C) is obtained by mixing the following products at 25°C:

[0197] 1,2,2,6,6-Pentamethyl-4-piperidinyl sebacate methyl ester (25% by weight) and bis(1,2,2,6,6-pentamethyl-4-piperidine base) sebacate (75% by weight);

[0198] Bis(2-ethylhexyl) phosphate (Bis(2-EHP)).

[0199] Table 7

[0200]

[0201] The initial viscosity was measured on the degassed clear solution thus obtained, and then the viscosity at the same temperature was measured in successive times, obtaining the values ​​shown in Table 8.

[0202] Table 8

[0203]

[0204] The above data indicate a pot life of more than 2 hours in each case and are therefore suitable for the production of optical articles on an industrial scale by manual casting techniques.

[0205] The polymerizable composition No. 6 thus obtained was poured into a glass mold an...

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Abstract

Polymerization catalysts are described for organic polythiourethane glass which do not contain organometallic compounds, and consisting of a mixture of a tertiary aliphatic amine and a disubstituted phosphoric acid in a molar ratio ranging from 1/1.3 to 1/20. Polymerizable liquid compositions of the polythiourethane type are also described, essentially consisting of three components (A), (B) and (C), wherein component (A) contains at least one cycloaliphatic diisocyanate monomer wherein the weight percentage of free isocyanate groups in said component (A) ranges from about 20% to about 50% by weight, preferably from about 25% to about 40% by weight, with respect to the total weight of component (A); component (B) contains at least one polythiol having a molecular weight ranging from 50 to 1,200 g/moles, preferably from 100 to 1000 g/moles, and a functionality ranging from 2 to 5, preferably from 2 to 4, said components (A) and (B) being present in a weight ratio varying from 0.5:1 to 2:1; component (C) being said polymerization catalyst. The process is also described for the production of organic glass starting from said polymerizable liquid compositions of the polythiourethane type.

Description

technical field [0001] The present invention relates to a polymerization catalyst for polythiourethanes, a polymerizable liquid composition containing the catalyst and the preparation of organic polythiourethanes having a high refractive index and good optical and physical-mechanical properties from said polymerizable liquid composition Process for ester glass; the invention also relates to organic glass obtained from the polymerization of said composition by mold casting. [0002] More specifically, according to the present invention, the method for preparing polythiourethane-based organic glasses having a high refractive index and good optical and physical-mechanical properties is applied to three types of glass consisting essentially of (A), (B) and (C) A polymerizable liquid composition consisting of: [0003] The first component (A) contains at least one cycloaliphatic diisocyanate monomer; the second component (B) contains one or more molecular weights in the range of 1...

Claims

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Application Information

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IPC IPC(8): C08G18/16C08G18/38C08G18/75G02B1/04C08G18/08
CPCC08G18/161G02B1/043C08G18/18C08G18/089C08G18/168C08G18/758C08G2125/00G02B1/04C08G18/0895G11B7/2533C08G18/3876C08L75/04C08L81/00C08G18/16C08G18/38C08G18/75G02B1/041
Inventor F·雷齐R·福里斯泰里A·维基艾奥尼W·博斯
Owner MITSUI CHEM INC
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