Polymerizable Compound for High Refractive Index Optical Resins

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Solution Overview

Problem

Current optical resins fail to achieve a high refractive index exceeding 1.7 while maintaining transparency, thermal properties, and mechanical strength, which are essential for advanced plastic lenses.

Innovation Solution

A polymerizable compound comprising one or more thietane groups and a metal atom, such as Sn, Si, or Ge, is developed, which upon polymerization forms a resin with enhanced refractive index, transparency, and mechanical strength.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Temperature

If conventional optical resins (DAC-based crosslinking type) are used, then transparency and heat resistance are excellent, but refractive index is low (nd=1.50) resulting in large lens thickness

Engineering Contradiction:
Improveheat resistanceVSAvoidrefractive index
Core Design Contradiction:
TemperatureVSStability of the object's composition

Solution Approach 1:

The patent introduces a composite resin system combining polythiourethane base resin with polymerizable compounds containing high refractive index groups (episulfide, selenide, metal carboxylates). This composite approach achieves refractive index exceeding 1.7 while preserving the excellent transparency and heat resistance of the polythiourethane matrix, solving the contradiction between maintaining thermal properties and achieving high refractive index.

Inventive Principle:
Principle #40Composite materials

2Strength

If polythiourethane is used, then transparency and impact resistance are excellent with high refractive index (nd=1.6 to 1.7), but lens thickness remains large for general-purpose applications

Engineering Contradiction:
Improveimpact resistanceVSAvoidrefractive index
Core Design Contradiction:
StrengthVSStability of the object's composition

Solution Approach 1:

The patent systematically varies the refractive index contribution by changing the type and content of polymerizable compounds (episulfide 0.1-10 wt%, selenide 0.1-5 wt%, metal carboxylates 1-50 wt%). This parameter adjustment enables fine-tuning of the final refractive index above 1.7 while preserving the impact resistance inherent in the polythiourethane structure, resolving the contradiction between strength and refractive index.

Inventive Principle:
Principle #35Parameter changes

3Stability of the object's composition

If compounds with episulfide groups are polymerized, then refractive index increases, but mechanical properties deteriorate

Engineering Contradiction:
Improverefractive indexVSAvoidmechanical properties
Core Design Contradiction:
Stability of the object's compositionVSStrength

Solution Approach 1:

The patent creates a composite system where episulfide-containing polymerizable compounds (providing high refractive index) are incorporated into a polythiourethane matrix (providing mechanical strength). The synergistic combination allows the resin to achieve refractive index above 1.7 while the polythiourethane base maintains excellent mechanical properties, resolving the contradiction between refractive index and mechanical strength.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent distributes the episulfide groups locally within the polymer matrix rather than using them as the bulk material. This localized incorporation (0.1-10 wt%) allows the high refractive index function to be achieved in specific regions while the majority of the matrix retains the mechanical properties of polythiourethane, resolving the contradiction between local refractive index enhancement and overall mechanical strength.

Inventive Principle:
Principle #3Local quality

4Stability of the object's composition

If Se-containing metal compounds are used, then refractive index increases, but safety problems arise

Engineering Contradiction:
Improverefractive indexVSAvoidsafety
Core Design Contradiction:
Stability of the object's compositionVSObject-affected harmful factors

Solution Approach 1:

The patent employs metal carboxylate compounds (such as tin, zinc, calcium carboxylates) as temporary refractive index enhancers during the polymerization process. These metal-containing polymerizable compounds serve their purpose of boosting refractive index above 1.7, and any residual metal compounds are present in minimal amounts in the final cured resin, significantly reducing safety concerns compared to Se-containing compounds.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The resulting resin exhibits high transparency, good heat resistance, and mechanical strength, making it suitable for high-quality plastic lenses with a refractive index exceeding 1.7.

Implementation Method 1

a compound comprising one or two or more thietane groups and a metal atom in a molecule, while attaining a very high refractive index

Methodology Applied
Scientific EffectRefractive index enhancement through metal atom incorporation:

Implementation Method 2

a resin obtained by polymerization of the polymerizable composition

Methodology Applied
Scientific EffectPolymerization: Photopolymerisation

Data Source

PatentUS7723318B2Polymerizable compound and use thereof
Publication Date: 2010.05.25 MITSUI CHEMICALS INC
  • US7723318B2 patent drawing
  • US7723318B2 patent drawing
  • US7723318B2 patent drawing

AI summary

The present invention is to provide a polymerizable compound which can be a raw material for a resin having high transparency, good heat resistance and mechanical strength required for optical components such as plastic lenses and the like, while attaining a high refractive index (nd) exceeding 1.7, and an optical component composed of such a resin.Disclosed is a compound represented by the general formula (3),wherein, in the formula, M represents a metal atom; X1 and X2 each independently represent a sulfur atom or an oxygen atom; R1 represents a divalent organic group; m represents an integer of 0 or 1 or more; p represents an integer of from 1 to n; q represents an integer of from 1 to (n-p); n represents a valence of a metal atom M; Yq each independently represent an inorganic or organic residue; and when q is 2 or more, Yq may be bonded to one another for forming a ring structure with the intermediary of a metal atom M.