Polymerized Rosin Compound for High-Molecular-Weight Polyester Resins

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Solution Overview

Problem

Current methods fail to produce high-molecular-weight linear polymers using commercially available polymerized rosin due to its composition and the difficulty in removing unreacted rosin acid, which limits the incorporation of rosin in the polymer main skeleton and hinders the exploitation of its heat-resistant properties.

Innovation Solution

Introducing reactive functional groups into the rosin structure to form a bifunctional rosin dimer, which increases the rosin dimer component content and suppresses decarboxylation, allowing for the synthesis of a polymerized rosin compound with a high rosin dimer component content, enabling the production of high-molecular-weight polyester resins with improved thermal stability and heat resistance.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If polymerized rosin with high rosin dimer component content is used, then high-molecular-weight linear polymer can be obtained, but conventional polymerized rosin contains only 55 to 80% by weight of rosin dimer component which is insufficient

Engineering Contradiction:
Improverosin dimer component contentVSAvoidpolymer molecular weight control
Core Design Contradiction:
Quantity of substanceVSManufacturing precision

Solution Approach 1:

The patent applies preliminary action by pre-enriching the rosin dimer component content to 95% or higher before polymerization. This is achieved through selective extraction methods that remove monomeric rosin acid and other impurities in advance, ensuring that the polymerization reaction starts with a highly concentrated dimer component, thereby enabling the formation of high-molecular-weight linear polymers without side reactions from monomers.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent applies parameter changes by significantly increasing the rosin dimer component content from the conventional 55-80% range to 95% or higher. This parameter change fundamentally alters the polymerization outcome, transforming the product from a mixture with limited molecular weight to a high-molecular-weight linear polymer with controlled structure and improved thermal properties.

Inventive Principle:
Principle #35Parameter changes

2Quantity of substance

If distillation under reduced pressure is used to increase rosin dimer component content, then unreacted rosin acid can be removed, but decarboxylation occurs during distillation which reduces polymer quality

Engineering Contradiction:
Improverosin dimer component concentrationVSAvoidpolymer composition stability
Core Design Contradiction:
Quantity of substanceVSReliability

Solution Approach 1:

The patent applies parameter changes by carefully controlling the distillation conditions, specifically maintaining the temperature below the decarboxylation point of rosin acid while operating under reduced pressure. This parameter optimization allows efficient removal of unreacted rosin acid and enrichment of the dimer component without triggering the harmful decarboxylation reaction that would compromise polymer quality.

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If abietic acid is used as polymer material, then polymer can be produced, but abietic acid is monofunctional and grafts at chain ends rather than incorporating into main skeleton

Engineering Contradiction:
Improvepolymer production feasibilityVSAvoidpolymer main skeleton structure
Core Design Contradiction:
Ease of manufactureVSStability of the object's composition

Solution Approach 1:

The patent applies the taking out principle by extracting and removing the monomeric abietic acid component from the reaction mixture through distillation under reduced pressure. This separation isolates the desired dimer component (which has two carboxyl groups capable of forming linear chains) from the monofunctional monomer, allowing the dimer to incorporate into the polymer main skeleton while the monomer is removed as a byproduct.

Inventive Principle:
Principle #2Taking out (Extraction)

4Productivity

If commercially available polymerized rosin is used, then polymerization can proceed, but the mixture composition prevents formation of high-molecular-weight linear polymer

Engineering Contradiction:
Improvepolymerization reaction rateVSAvoidhigh-molecular-weight polymer yield
Core Design Contradiction:
ProductivityVSQuantity of substance

Solution Approach 1:

The patent applies preliminary action by performing pre-polymerization or pre-treatment steps that convert monomeric rosin acid into dimer forms before the main polymerization reaction. This preliminary transformation ensures that when polymerization occurs, the predominant species are dimers capable of forming linear high-molecular-weight chains, rather than a mixture that would produce lower molecular weight products.

Inventive Principle:
Principle #10Preliminary action

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 polymerized rosin compound with a high bifunctional rosin dimer content successfully incorporates rosin in the polymer main skeleton, resulting in polyester resins with higher molecular weight, thermal decomposition temperature, and heat resistance.

Implementation Method 1

polymerization of rosin such as gum rosin, wood rosin, or tall oil rosin

Methodology Applied
Scientific EffectPolymerization: Photopolymerisation

Data Source

PatentUS10392465B2Polymerized rosin compound and production method therefor
Publication Date: 2019.08.27 ARAKAWA CHEM IND LTD
  • US10392465B2 patent drawing

AI summary

A polymerized rosin compound includes a rosin dimer component (A) including a bifunctional rosin dimer component (a1) represented by formula (1): ROOC—X—COOR. In this formula, X represents a rosin dimer residue derived from abietic acid, neoabietic acid, or palustric acid, which are resin acids having conjugated double bonds; and R represents hydrogen, an alkyl group of I to 5 carbon atoms, or a benzyl group. The rosin dimer component (A) contains a bifunctional rosin dimer component (a1) in the amount of 80% by weight or more and a rosin trimer or higher oligomer component (B) in the range from 1.5 to 3.7% by weight, wherein the rosin dimer component is free of a monofunctional rosin dimer component (a2) having one functional group represented by formula (2): ROOC—, wherein R represents hydrogen, an alkyl group of 1 to 5 carbon atoms, or a benzyl group, and free from functional group containing rosin dimer component (a3), wherein the functional group represented by formula (2): ROOC—, wherein R represents hydrogen, an alkyl group of 1 to 5 carbon atoms, or a benzyl group. The polymerized rosin compound contains a large amount of the bifunctional rosin dimer component that makes it possible to obtain linear polymer with a high molecular weight.