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Method for preparing (meth)acrylates of biobased alcohols and polymers thereof

A secondary alkyl acrylate, bio-based technology, applied in the field of dehydration of bio-based alcohols

Inactive Publication Date: 2015-11-11
3M INNOVATIVE PROPERTIES CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The present disclosure provides a solution to the problems associated with the production of polymers, particularly polymers used in pressure sensitive adhesives (PSAs), from petroleum-only feedstocks

Method used

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  • Method for preparing (meth)acrylates of biobased alcohols and polymers thereof
  • Method for preparing (meth)acrylates of biobased alcohols and polymers thereof
  • Method for preparing (meth)acrylates of biobased alcohols and polymers thereof

Examples

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example

[0228] These examples are for illustration purposes only, and are not intended to unduly limit the scope of the appended claims. Notwithstanding that the numerical ranges and parameters setting forth the broad scope of the disclosure are approximations, the numerical values ​​set forth in the specific examples are reported as precisely as possible. Any numerical value, however, inherently contains certain errors necessarily resulting from the standard deviation found in their respective testing measurements. At the very least, and not as an attempt to limit the application of the doctrine of equivalents to the scope of the claims, each numerical parameter should at least be construed in light of the number of reported significant digits and by applying ordinary rounding techniques.

[0229] material overview

[0230] All parts, percentages, ratios, etc. in the examples, as well as in the remainder of the specification, are by weight unless otherwise indicated. Table 1 prov...

example 1

[0240] Example 1: Octene derived from 1-octanol

[0241] A 2 liter (L) Erlenmeyer flask was charged with 1200 grams (g) of 1-octanol derived from vegetable oil and 100 g of AMBERLY ST70 catalyst material (sulfonated styrene divinylbenzene copolymer). The flask was heated to about 180°C and heated at 4.2 ml / min (mLmin -1 ) at a rate of 1-octanol was continuously fed into the flask. During the reaction, product water and octene evaporate into a 1.5 inch (3.8 cm) internal diameter (I.D.) by 24 inch (61 cm) long fractionation column equipped with a condenser and reflux ratio controller (i.e., reflux valve), which were kept constant at 5°C and a 1:1 ratio, respectively. After at least 1 hour of continuous operation at 2.51gh -1 (g catalyst) -1 (6.97×10 -4 gs -1 (g catalyst) -1 ) rate was collected for analysis and found to consist primarily of a mixture of octene isomers and water. Water was then separated from the product mixture using a separatory funnel to yield the oc...

example 2

[0242] Example 2: Octene derived from 2-octanol

[0243] A 3 L round bottom flask was charged with 800 g of 2-octanol derived from vegetable oil and 100 g of AMBERLY ST70 catalyst material (sulfonated styrene divinylbenzene copolymer). The flask was heated to about 130°C and heated at 6.66mLmin -1 The rate of 2-octanol was continuously fed into the flask. During the reaction, the product water and octene evaporate into a 1.5 inch (3.8 cm) ID x 24 inch (61 cm) long splitter column equipped with a condenser and reflux ratio controller (i.e., reflux valve) , which are kept constant at 5°C and a 1:1 ratio, respectively. After at least 1 hour of continuous operation, at 4.716gh -1 (g catalyst) -1 (1.31×10 -3 gs -1 (g catalyst) -1 ) rate was collected for analysis and found to consist primarily of a mixture of octene isomers and water. Water was then separated from the product mixture using a separatory funnel to yield the octene product.

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Abstract

Polymers, particularly those used in pressure-sensitive adhesives, are prepared from a mixture of structural isomers of a secondary alkyl (meth)acrylate monomer. The mixture is made by dehydrating a biobased C2-C22 alcohol with a first acid catalyst using a continuous process to form a mixture of olefins, and reacting (meth)acrylic acid with at least some of the mixture of olefins in the presence of a second acid catalyst. The adhesives are characterized by exhibiting an overall balance of adhesive and cohesive characteristics, and containing biobased material.

Description

technical field [0001] The present disclosure relates to the selective synthesis of mixtures of olefins, including the dehydration of bio-based alcohols. Olefins are useful in the preparation of polymers such as pressure sensitive adhesives. Background technique [0002] Pressure sensitive tapes are ubiquitous in homes and workplaces. In its simplest construction, a pressure sensitive tape includes an adhesive and a backing, the overall construction is tacky at use temperatures, and adheres to a variety of substrates with only moderate pressure to form a bond. In this way, the pressure sensitive tape constitutes a complete self-contained bonding system. [0003] There are a variety of pressure sensitive adhesive (PSA) materials available today including natural or synthetic rubber, block copolymers, and (meth)acrylic-based polymer compositions. Over the past half century, (meth)acrylic-based PSAs in particular have been the focus of a great deal of development as the perf...

Claims

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Application Information

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IPC IPC(8): C07C67/04C07C1/24C09J7/00
CPCC07C67/04C07C1/24C07C2531/10C09J7/00C09J7/0217C09J2423/00C09J133/08C08F220/1808C07C69/54C07C11/02C08F220/1804C08F220/06C07C2531/08
Inventor 乔舒亚·L·科尔比阿伦·E·胡特特伦斯·D·斯帕贾森·D·克拉珀塔比萨·A·克莱姆
Owner 3M INNOVATIVE PROPERTIES CO
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