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

Patent metadata

Field	Value
Publication number	US-9568644-B2
Application number	US-201414329470-A
Country	US
Kind code	B2
Filing date	Jul 11, 2014
Priority date	May 20, 2010
Publication date	Feb 14, 2017
Grant date	Feb 14, 2017

Abstract

Polymerizable liquid compositions containing three components (A), (B) and (C) are provided, wherein component (A) contains at least one cycloaliphatic diisocyanate monomer wherein the weight percentage of free isocyanate groups in component (A) ranges from about 20% to about 50% 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 and a functionality ranging from 2 to 5, the components (A) and (B) being present in a weight ratio varying from 0.5:1 to 2:1; and component (C) being a defined polymerization catalyst. A process for the production of organic glass using the polymerizable liquid composition is further provided.

First claim

The invention claimed is:

1. A polymerizable liquid composition of polythiourethane, comprising three components (A), (B), and (C),
wherein component (A) is selected from 4,4′-methylene bis(cyclohexyl isocyanate) and bis(isocyanate methyl) cyclohexane;
component (B) is selected from 2,3-bis((2-mercaptoethyl)thio)-1-propanethiol and a mixture of 2,3-bis((2-mercaptoethyl)thio)-1-propanethiol and ethylene glycol-di(3-mercaptopropionate),
wherein said components (A) and (B) are present in a weight ratio varying from 0.5:1 to 2:1;
component (C) being a catalyst for organic polythiourethane glass, wherein the catalyst does not contain organometallic compounds and consists of a mixture of a tertiary amine and a disubstituted phosphoric acid, wherein the component (C) is selected from a mixture of triethylamine and bis(2-ethylhexyl)phosphate and a mixture of methyl-1,2,2,6,6-pentamethyl-4 piperidinyl sebacate and bis(1,2,2,6,6-pentamethyl-4 piperidinyl)sebacate with bis(2-ethylhexyl)phosphate,
wherein the tertiary amine and the disubstituted phosphoric acid are present in a molar ratio ranging from 1/1.3 to 1/20.

2. The polymerizable composition according to claim 1 , wherein component (A) is 4,4′-methylene bis(cyclohexyl isocyanate) and component (B) is a mixture of 2,3-bis((2-mercaptoethyl)thio)-1-propanethiol and ethylene glycol-di(3-mercaptopropionate).

3. The polymerizable composition according to claim 1 , wherein the quantity of component (C) ranges from 0.1 to 2% by weight with respect to the total weight of the polymerizable composition.

4. The polymerizable composition according to claim 3 , wherein the quantity of component (C) ranges from 0.2 to 1.5% by weight with respect to the total weight of the polymerizable composition.

5. The polymerizable composition according to claim 1 , wherein the catalyst consists of mixtures of triethylamine and bis(2-ethylhexyl)phosphate.

6. A process for the production of organic glass which provides a casting and polymerization process of the polymerizable liquid composition of polyurethane, according to claim 1 , comprising the following phases:
a mixing phase a) of components (A) and (C);
a mixing phase b) of the solution obtained in the mixing phase a) and component (B), optionally in the presence of other additives;
a filtration phase c) to remove any pollutants dispersed in the mixture, said filtration phase also being effected alternatively or additionally, on the single components (A) and (B) before the mixing phase b);
a filling phase d) of a mould, wherein the mixture obtained at the end of phase c) is placed inside the mould; and
a polymerization phase e) wherein the liquid composition placed in the mould, is polymerized by thermal treatment.

7. Organic glass obtained by the process according to claim 6 .

8. Manufactured products or optical articles obtained by the processing of the organic glass according to claim 7 .

9. Manufactured products or optical articles according to claim 8 , selected from the group consisting of ophthalmic lenses, solar filters, Fresnel lenses, protective and safety shields, displays, substrates for optical disks, display panels and video display units, optical guides, components for mobile phones, transparent tubes.

Assignees

• Mitsui Chemicals Inc

Inventors

• Renzi Fiorenzo
• Forestieri Roberto
• Vecchione Andrea Lukas
• Bos Willem

Classifications

• C08G18/089 Primary

  Reaction retarding agents · CPC title

• C08G2125/00

  Compositions for processes using internal mould release agents · CPC title

• C08L75/04

  Polyurethanes · CPC title

• G11B7/2533

  comprising resins · CPC title

• C08G18/3876

  containing mercapto groups · CPC title