Two-Part Adhesive Composition Using Vinyl Ether Diluents

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Solution Overview

Problem

There is a need for alternative reactive diluents that do not cause premature curing of Part A composition or adversely affect the curing of adhesives when mixed with Part B, particularly in the presence of organoborane-amine complexes, which are unstable and can be toxic.

Innovation Solution

The use of vinyl ethers and vinyl-terminated polysiloxanes as reactive diluents with organoborane-amine complexes, along with a decomplexing agent, to initiate curing under ambient or mild conditions, forming stable two-part adhesive compositions that can polymerize and crosslink in the presence of oxygen.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If conventional reactive diluents (1,4-dioxo-2-butene-functional compounds, aziridine-functional compounds, vinyl aromatic compounds) are used with organoborane-amine complexes, then the adhesive composition can be formulated, but premature curing occurs and stability is compromised

Engineering Contradiction:
Improveadhesive composition formulationVSAvoidPart A composition stability
Core Design Contradiction:
Ease of manufactureVSStability of the object's composition

Solution Approach 1:

The patent introduces vinyl ether compounds as intermediary substances that mediate between the organoborane-amine complex and the final cured adhesive. These vinyl ethers act as stable reactive diluents that do not trigger premature decomplexing or curing, unlike conventional reactive diluents. The vinyl ether serves as a bridge that maintains system stability during storage while enabling proper curing when activated by moisture or heat in the Part B composition.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Ease of manufacture

If conventional reactive diluents are used, then the adhesive can be formulated, but toxicity increases and stability deteriorates

Engineering Contradiction:
Improveadhesive formulation capabilityVSAvoidtoxicity and instability
Core Design Contradiction:
Ease of manufactureVSObject-affected harmful factors

Solution Approach 1:

The patent employs vinyl ether compounds as temporary, consumable reactive diluents that serve their purpose during formulation and curing, then are consumed or transformed in the curing process. These vinyl ethers replace toxic conventional diluents with safer, more stable alternatives that fulfill the diluent function without introducing harmful effects or long-term stability issues.

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

3Productivity

If organoborane-amine complexes are used as initiators, then rapid polymerization can occur, but premature curing and instability are caused

Engineering Contradiction:
Improvepolymerization rateVSAvoidcomplex stability during storage
Core Design Contradiction:
ProductivityVSStability of the object's composition

Solution Approach 1:

The patent divides the adhesive system into two separate parts: Part A containing the organoborane-amine complex with vinyl ether diluent, and Part B containing the polymerizable monomers and decomplexing agent. This segmentation prevents premature interaction between the initiator and monomer, maintaining stability during storage while enabling rapid polymerization when the parts are mixed and the decomplexing agent releases the organoborane initiator.

Inventive Principle:
Principle #1Segmentation

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

These compositions demonstrate stability with organoborane complexes and effectively cure to form viscoelastic solids, suitable for adhesives, sealants, and potting resins, offering improved stability and performance compared to existing systems.

Implementation Method 1

an organoborane-amine complex, which can be used in the presence of oxygen or a peroxygen compound to initiate the curing (i.e., polymerization and/or crosslinking)

Methodology Applied
Scientific EffectOxidation: Oxidation

Implementation Method 2

a decomplexing agent that decomplexes the organoborane and the amine complexing agent

Methodology Applied
Scientific EffectDecomplexation:

Implementation Method 3

diluents containing vinyl ethers, and/or vinyl-terminated polysiloxanes demonstrate stability with respect to the organoborane complex

Methodology Applied
Scientific EffectComplex stabilization:

Implementation Method 4

compositions that can cure (i.e., polymerize and/or crosslink) under ambient or mild conditions

Methodology Applied
Scientific EffectPolymerization:

Implementation Method 5

compositions that can cure (i.e., polymerize and/or crosslink) under ambient or mild conditions

Methodology Applied
Scientific EffectCrosslinking:

Data Source

PatentUS10221337B2Two-part adhesive composition and method of making an adhesive composition
Publication Date: 2019.03.05 3M INNOVATIVE PROPERTIES CO
  • US10221337B2 patent drawing
  • US10221337B2 patent drawing
  • US10221337B2 patent drawing

AI summary

A two-part adhesive composition includes: a Part A including a complex of an organoborane and an amine complexing agent, and reactive diluent selected from the group consisting of at least one vinyl ether, at least one vinylpolysiloxane, or combinations thereof; and a Part B. Part B includes a decomplexing agent that decomplexes the organoborane and the amine complexing agent, and at least one silicon-free free-radically polymerizable ethylenically-unsaturated compound selected from the group consisting of (meth)acrylates, (meth)acrylamides, and combinations thereof. The two-part adhesive composition is essentially free of organic polythiol compounds. A method of making an adhesive composition by mixing Part A with Part B is also disclosed.