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

Patent metadata

Field	Value
Publication number	US-9908837-B2
Application number	US-201414769850-A
Country	US
Kind code	B2
Filing date	Mar 13, 2014
Priority date	Mar 15, 2013
Publication date	Mar 6, 2018
Grant date	Mar 6, 2018

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 C 2 -C 22 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.

First claim

What is claimed is:

1. A method of making a mixture of structural isomers of a secondary alkyl(meth)acrylate of Formula (I):

wherein:
R 1 and R 2 are each independently a C 1 to C 20 saturated linear alkyl group;
the sum of the number of carbons in R 1 and R 2 is 2 to 21; and
R 3 is H or CH 3 ;

wherein the method comprises:
dehydrating a biobased C 2 -C 22 alcohol derived from at least one plant oil with a first acid catalyst using a continuous process, thereby forming a mixture of olefins, the first acid catalyst comprising a sulfonated styrene divinylbenzene copolymer; and
reacting (meth)acrylic acid with at least some of the mixture of olefins in the presence of a second acid catalyst comprising a sulfonated styrene divinylbenzene copolymer.

2. The method of claim 1 wherein the first acid catalyst comprises a cation exchange resin.

3. The method of claim 1 wherein the mixture of olefins comprises between 80% and 100% by weight biobased olefins, as determined using ASTM D6866-12.

4. The method of claim 1 wherein the dehydrating occurs at a temperature of 150° C. to 190° C.

5. The method of claim 1 wherein the C 2 -C 22 alcohol comprises a C 8 alcohol, a C 10 alcohol, or a C 12 alcohol.

6. The method of claim 1 wherein the dehydrating is performed in a continuous reactor at a temperature of 150° C. to 190° C. and at a constant weight hourly space velocity (WHSV) of 0.5 h −1 to 10 h −1 , wherein the WHSV is a ratio of mass flow of the C 2 -C 22 alcohol entering the system per hour to the mass of the first acid catalyst.

7. The method of claim 1 wherein the dehydrating is performed in a continuous reactor at a temperature of 150° C. to 190° C. and combination of the mixture of olefins and water is produced at a rate of 0.5 g h −1 to 10 g h −1 per gram of the first acid catalyst.

Assignees

• 3M Innovative Properties Co

Inventors

• Colby Joshua L
• Hutt Aaron E
• Spawn Terence D
• Clapper Jason D
• Clem Tabitha A

Classifications

• C07C1/24

  by elimination of water · CPC title

• C07C2531/08

  Ion-exchange resins · CPC title

• C07C67/04 Primary

  by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds · CPC title

• C07C2531/10

  sulfonated · CPC title

• C09J133/08

  Homopolymers or copolymers of acrylic acid esters · CPC title