Ultraviolet radiation-cured pressure sensitive adhesives from plant oils or animal fats

Patent metadata

Field	Value
Publication number	US-2022017788-A1
Application number	US-201917295004-A
Country	US
Kind code	A1
Filing date	Nov 18, 2019
Priority date	Nov 20, 2018
Publication date	Jan 20, 2022
Grant date	—

Abstract

A pressure sensitive adhesive construct comprising:(A) a backing substrate; and(B) a pressure sensitive adhesive composition disposed on the backing substrate, wherein the pressure sensitive adhesive composition includes an ultraviolet radiation-cured polymer made from:(a) at least one epoxidized plant oil, at least one epoxidized animal fat, or a mixture thereof;(b) at least one dicarboxylic acid, at least one polycarboxylic acid, or a mixture thereof; and(c) at least one compound that contains both one carbon-carbon double bond (C═C) and at least one carboxylic acid group.

First claim

1 . A pressure sensitive adhesive construct comprising:
(A) a backing substrate; and (B) a pressure sensitive adhesive composition disposed on the backing substrate, wherein the pressure sensitive adhesive composition includes an ultraviolet radiation-cured polymer made from: (a) at least one epoxidized plant oil, at least one epoxidized animal fat, or a mixture thereof; (b) at least one dicarboxylic acid, at least one polycarboxylic acid, or a mixture thereof; and (c) at least one compound that contains both one carbon-carbon double bond (C═C) and at least one carboxylic acid group.

2 . The construct of claim 1 , wherein component (a) is monocarboxylic acid-modified epoxidized soybean oil.

3 . The construct of claim 2 , wherein the monocarboxylic acid modifier is formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, undecylic acid, lauric acid, tridecylic acid, myristic acid, pentadecylic acid, palmitic acid, margaric acid, stearic acid, nonadecylic acid, arachildic acid, heneicosylic acid, behenic acid, tricosylic acid, and lignoceric acid, naphthalene acid, oleic acid, linoleic acid, myristoleic acid, palmitoleic acid, sapienic acid, elaidic acid, vaccenic acid, linoelaidic acid, linolenic acid, arachidonic acid, eicosapentaenoic acid, erucic acid, docosahexanenoic acid, abietic acid or tall oil rosin that contains abietic acid, benzoic acid, phenylacetic acid, 1-naphthaleneacetic acid, 2-naphthaleneacetic acid, 1-naphthoic acid, 2-naphthoic acid, 2-furoic acid, 3-methylpyridine-2-carboxylic acid, 1-methylpyrrole-2-carboxylic acid, pyrimidine-2-carboxylic acid, or an anhydride thereof, or a mixture thereof.

4 . The construct of claim 1 , wherein component (a) is epoxidized soybean oil.

5 . The construct of claim 1 , wherein component (b) is malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, and brassylic acid, phthalic acid, isophthalic acid, terephthalic acid, dimer acid, trimer acid, or an anhydride thereof, or a mixture thereof.

6 . The construct of claim 1 , wherein component (b) is a mixture of dimer acid, trimer acid, and polymeric fatty acid.

7 . The construct of claim 1 , wherein component (b) is adipic acid.

8 . The construct of claim 1 , wherein component (b) is a polymer or an oligomer that is capped with —COOH groups at chain ends of the polymer or the oligomer.

9 . The construct of claim 1 , wherein component (c) is itaconic acid, fumaric acid, maleic acid, or an anhydride thereof, or a mixture thereof.

10 . The construct of claim 1 , wherein component (c) is itaconic acid.

11 . The construct of claim 1 , wherein component (c) is acrylic acid, methacrylic acid, or an anhydride thereof, or a mixture thereof.

12 . The construct of claim 1 , wherein component (c) is acrylic acid.

13 . The construct of claim 1 , wherein the ultraviolet radiation-cured polymer is also made from at least one thiol containing-compound.

14 . The construct of claim 13 , wherein the thiol containing-compound is trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptopropionate), 1,2-bis(2-mercaptoethoxy)ethane, tetra(ethylene glycol) dithiol, poly(ethylene glycol) dithiol, 1,6-hexanedithiol, 4,4′-thiobisbenozenethiol, a thiol containing-plant oil, or a mixture thereof.

15 . The construct of claim 13 , wherein the thiol-containing compound is a mercaptanized soybean oil from reaction of soybean oil with hydrogen disulfide, or a mercapto hydroxy soybean oil from reaction of epoxidized soybean oil with hydrogen disulfide.

16 . A pressure sensitive adhesive construct comprising:
(A) a backing substrate; and (B) a pressure sensitive adhesive composition disposed on the backing substrate, wherein the pressure sensitive adhesive composition includes an ultraviolet radiation-cured semi-interpenetrating polymer network made from a blend of: (a) at least one compound containing at least two acrylate or methacrylate groups; (b) a photoinitiator; and (c) a polyester prepared from polymerization of at least one monocarboxylic acid modified-epoxidized plant oil with at least one dicarboxylic acid or polycarboxylic acid.

17 . A pressure sensitive adhesive construct comprising:
(A) a backing substrate; and (B) a pressure sensitive adhesive composition disposed on the backing substrate, wherein the pressure sensitive adhesive composition includes an ultraviolet radiation-cured polymer having a structure of:

wherein MEPO denotes structure derived from an epoxidized plant oil or modified epoxidized plant oil; DA denotes structure derived from a dicarboxylic acid or polycarboxylic acid; each R′ is independently H or methyl group; each R is independently an alkyl derived from a part of fatty acid chains from the epoxidized plant oil or the modified epoxidized plant oil; and each represents independently a segment of a polyester chain.

18 . A pressure sensitive adhesive composition comprising an ultraviolet radiation-cured polymer made from:
(a) at least one epoxidized plant oil, at least one epoxidized animal fat, or a mixture thereof; (b) at least one dicarboxylic acid, at least one polycarboxylic acid, or a mixture thereof; and (c) at least one compound that contains both one carbon-carbon double bond (C═C) and at least one carboxylic acid group.

19 . The composition of claim 18 , wherein:
component (a) is monocarboxylic acid-modified epoxidized soybean oil or epoxidized soybean oil; component (b) is a mixture of dimer acid, trimer acid, and polymeric fatty acid; or adipic acid; and component (c) is itaconic acid or acrylic acid.

20 . The composition of claim 18 , wherein the ultraviolet radiation-cured polymer is also made from at least one thiol containing-compound.

21 . A pressure sensitive adhesive composition comprising a polymer having a structure of:

wherein MEPO denotes structure derived from an epoxidized plant oil or modified epoxidized plant oil; DA denotes structure derived from a dicarboxylic acid or polycarboxylic acid; each R′ is independently H or methyl group; each R is independently an alkyl derived from a part of fatty acid chains from the epoxidized plant oil or the modified epoxidized plant oil; and each represents independently a segment of a polyester chain.

22 . The composition of claim 18 , further comprising a tackifier.

23 . The composition of claim 23 , wherein the tackifier is the reaction product of an epoxidized plant oil with tall oil rosin.

24 . An ultraviolet radation-curable composition comprising:
(a) at least one epoxidized plant oil, at least one epoxidized animal fat, or a mixture thereof; (b) at least one dicarboxylic acid, at least one polycarboxylic acid, or a mixture thereof; (c) at least one compound that contains both one carbon-carbon double bond (C═C) and at least one carboxylic acid group; and (d) at least one photoinitiator.

25 . A method comprising:
polymerizing (a) at least one epoxidized plant oil, at least one epoxidized animal fat, or a mixture thereof, (b) at least one dicarboxylic acid, at least one polycarboxylic acid, or a mixture thereo

Assignees

• Univ Oregon State

Inventors

• Li Kaichang
• Li Anlong

Classifications

• C08K5/092

  Polycarboxylic acids · CPC title

• C09J7/38 Primary

  Pressure-sensitive adhesives [PSA] · CPC title

• C08G59/1455

  Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof · CPC title

• C09J2301/416

  use of irradiation · CPC title

• C09J2301/408

  additives as essential feature of the adhesive layer · CPC title