Adhesive precursor composition, two-part adhesive kit, and method of making an adhesive composition

Patent metadata

Field	Value
Publication number	US-2017190937-A1
Application number	US-201515313272-A
Country	US
Kind code	A1
Filing date	Jun 12, 2015
Priority date	Jun 24, 2014
Publication date	Jul 6, 2017
Grant date	—

Abstract

A two-part adhesive kit having a part A and part B is disclosed. Part A, an adhesive precursor composition, includes at least one free-radically polymerizable compound, at least one beta-dicarbonyl compound, and at least one nitro compound. Part B includes at least one free-radically polymerizable compound, at least one salt or oxide of a polyvalent metal, and at least one non-metallic halide salt. Methods of making an adhesive composition by combining part A with part B is also disclosed.

First claim

1 - 14 . (canceled)

15 . An adhesive precursor composition comprising:
at least one free-radically polymerizable compound; a beta-dicarbonyl compound represented by the formula

or a salt thereof, wherein:
R 1 and R 2 independently represent a hydrocarbyl group or a substituted-hydrocarbyl group having from 1 to 18 carbon atoms;
R 3 represents hydrogen, or a hydrocarbyl group or a substituted-hydrocarbyl group having from 1 to 18 carbon atoms; and

each X independently represents O, S,
wherein each R 4 independently represents H or a hydrocarbyl group having from 1 to 18 carbon atoms, or taken together any two of R 2 , R 3 , or R 4 form a ring; and

at least one nitro compound represented by the formula

wherein
R 5 represents an n-valent substituted or unsubstituted aromatic group having from 1 to 20 carbon atoms and free of nitroxyl groups, and
n represents a positive integer.

16 . The adhesive precursor composition of claim 15 further comprising at least one organic peroxide.

17 . The adhesive precursor composition of claim 15 , wherein the nitro compound is present in an amount of less than 10 percent by weight based on the total weight of the composition.

18 . The adhesive precursor composition of claim 15 , wherein said at least one nitro compound comprises 2-nitrobenzoic acid.

19 . The adhesive precursor composition of claim 15 , wherein at least one of said at least one beta-dicarbonyl compound is represented by the formula

wherein R 6 and R 7 are independently selected from the group consisting of H, an alkyl group having 1 to 18 carbon atoms, an aryl group having from 6 to 14 carbon atoms, an alkaryl group having from 7 to 15 carbon atoms, and an aralkyl groups having from 7 to 15 carbon atoms.

20 . The adhesive precursor composition of claim 15 , wherein the at least one free-radically polymerizable compound comprises a methacrylate monomer or acrylate monomer.

21 . A two-part adhesive kit comprising:
a part A composition comprising:
i) at least one free-radically polymerizable compound;
ii) at least one beta-dicarbonyl compound represented by the formula

or a salt thereof, wherein:
R 1 and R 2 independently represent a hydrocarbyl group or substituted-hydrocarbyl group having from 1 to 18 carbon atoms;
R 3 represents hydrogen, a hydrocarbyl group, or a substituted-hydrocarbyl group having from 1 to 18 carbon atoms; and
each X independently represents O, S,

wherein each R 4 independently represents H or a hydrocarbyl group having from 1 to 18 carbon atoms, or taken together any two of R 2 , R 3 , or R 4 form a ring; and

iii) at least one nitro compound represented by the formula

wherein
R 5 represents an n-valent substituted or unsubstituted aromatic group having from 1 to 20 carbon atoms and free of nitroxyl groups, and
n represents a positive integer; and

ii) a part B composition comprising:
at least one free-radically polymerizable compound,
at least one salt or oxide of a polyvalent metal, and
at least one non-metallic halide salt.

22 . The two-part adhesive kit of claim 21 , wherein the part A composition further comprises at least one organic peroxide.

23 . The two-part adhesive kit of claim 21 , wherein at least one of the part A composition or the part B composition further comprises a toughening agent.

24 . The two-part adhesive kit of claim 21 , wherein said at least one nitro compound is present in an amount of less than 10 percent by weight based on the total weight of the part A composition.

25 . The two-part adhesive kit of claim 21 , wherein said at least one nitro compound comprises 2-nitrobenzoic acid.

26 . The two-part adhesive kit of claim 21 , wherein at least one of said at least one beta-dicarbonyl compound is represented by the formula

wherein R 6 and R 7 are independently selected from the group consisting of H, an alkyl group having 1 to 18 carbon atoms, an aryl group having from 6 to 14 carbon atoms, an alkaryl group having from 7 to 15 carbon atoms, and an aralkyl group having from 7 to 15 carbon atoms.

27 . The two-part adhesive kit of claim 21 , wherein said at least one free-radically polymerizable compound comprises a methacrylate monomer or acrylate monomer.

28 . A method of making an adhesive composition, the method comprising combining the part A and part B compositions of the two-part adhesive kit of claim 21 .

Assignees

• 3M Innovative Properties Co

Inventors

• Thompson Zachary J
• Kasahara Takahiro

Classifications

• C09J4/00 Primary

  Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16} · CPC title

• C08K5/11

  of acyclic polycarboxylic acids · CPC title

• C09J133/06

  of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical · CPC title

• C08K5/1575

  Six-membered rings · CPC title

• C08K5/3462

  Six-membered rings · CPC title