3m Innovative Properties Company

Zachary J Thompson

Michael A Kropp

Joseph D Rule

Kolby L White

Yoshihiko Tasaka

Guy D Joly

Robert Steven Clough

Jun Fujita

William H Moser

Richard B Ross

Matthew J Kryger

Erik M Townsend

Mary M Caruso Dailey

Lianzhou Chen

Jay S Schlechte

George M Stout

Sotaro Endo

Gregory P Karp

Takahiro Kasahara

Erin A Suchara

Charlotte C Clark

Takahiro Danjo

Daiki Koseki

Yaoyao Chen

A two-part epoxy adhesive comprises a Part A and a Part B. Part A comprises, based on the total weight of components a) and b): a) 99.5 to 99.99 weight percent of at least one curable epoxy resin; and b) 0.01 to 0.5 weight percent of at least one pH indicator dye exhibiting an abrupt color change from colorless to a color in the pH range of 8.0-10.6. Part B comprises, based on the total weight of components c)-f): c) 89 to 97 weight percent of at least one aliphatic primary polyamine; d) 1 to 3 weight percent of at least one tris(2,4,6-dialkylaminoalkyl)phenol having from 13 to 24 carbon atoms; e) 1 to 3 weight percent of at least one aliphatic tertiary 1,3-bis(N,N-dialkylaminoalkyl)urea having from 6 to 24 carbon atoms; and f) 1 to 5 weight percent at least one of an alkali metal nitrate or an alkaline earth nitrate. The ratio of the total combined weight of components a) and b) to the total combined weight of components c)-f) is in the range 1.0 to 1.5. A reaction product thereof and a method of bonding are also disclosed.

Two-part epoxy adhesive with working life color change indicator

The present disclosure provides a redox initiator system for initiating polymerization comprising an oxidizing agent, a photolabile reducing agent derived from a barbiturate, and a transition metal complex that participates in a redox cycle. On exposure to actinic radiation, such as UV, the photolabile compound photolyzes, releasing the reducing agent and initiating the redox-initiated polymerization.

Photolabile barbiturate compounds

The present disclosure provides a polymeric material including a polymerized reaction product of a polymerizable composition including components and has a solids content of 90% or greater. The components include a uretdione-containing material including a reaction product of a diisocyanate reacted with itself; a first hydroxyl-containing compound; an optional second hydroxyl-containing compound having a single OH group, wherein; and an epoxy component. The first hydroxyl-containing compound has more than one OH group and the optional second hydroxyl-containing compound is a primary alcohol or a secondary alcohol. The present disclosure also provides a two-part composition, in which the polymeric material is included in the first part and the second part includes at least one amine. Further, a method of adhering two substrates is provided, including obtaining a two-part composition; combining at least a portion of the first part with at least a portion of the second part to form a mixture; disposing at least a portion of the mixture on a first substrate; and contacting a second substrate with the mixture disposed on the first substrate. The disclosure also provides a polymeric material and a method of making a two-part composition. Advantageously, two-part compositions according to the present disclosure can be used as coatings and adhesive systems with handling and performance similar to existing two-part urethane systems, but with less sensitivity to water.

Polymeric material including a uretdione-containing material and an epoxy component, two-part compositions, and methods

The present disclosure provides a polymeric material including a reaction product of a polymerizable composition and having a solids content of 90% or greater. The polymerizable composition includes a uretdione-containing material including a reaction product of a diisocyanate reacted with itself, a first hydroxyl-containing compound having a single OH group, and a second hydroxyl-containing compound having more than one OH group. The first hydroxyl-containing compound is a primary alcohol or a secondary alcohol, plus the second hydroxyl-containing compound is a diol and the reaction product contains 0.2 to 0.5, inclusive, of diol equivalents relative to isocyanate equivalents. The present disclosure also provides a two-part composition, in which the polymeric material is included in the first part and the second part includes at least one amine. Further, a method of adhering two substrates is provided, including obtaining a two-part composition; combining at least a portion of the first part with at least a portion of the second part to form a mixture; disposing at least a portion of the mixture on a first substrate; and contacting a second substrate with the mixture disposed on the first substrate. The disclosure also provides a polymeric material and a method of making a two-part composition. Advantageously, two-part compositions according to the present disclosure can be used as coatings and adhesive systems with handling and performance similar to existing two-part urethane systems, but with less sensitivity to water.

Polymeric material including a uretdione-containing material, two-part compositions, and methods

A polymerizable composition that includes: an organoborane-base complex, wherein the base is a complexing agent selected from a compound having one or more amine groups, amidine groups, hydroxide groups, alkoxide groups, or combinations thereof; a decomplexing agent that liberates the organoborane from the organoborane-base complex; a polymerizable thiol-containing component that includes at least one polymerizable thiol-containing compound having a plurality of thiol groups in which the sulfur atom of the thiol group is covalently bonded to carbon; and a polymerizable ethylenically unsaturated component that includes at least one polymerizable ethylenically unsaturated compound having a plurality of ethylenically unsaturated groups; wherein the total amount of the thiol-containing and ethylenically unsaturated compounds total at least 50% by weight of all polymerizable material in the composition.

Organoborane-containing compositions, and methods of using same

A method of curing a curable composition includes: providing the curable composition; providing a substrate having a primer disposed on at least a portion thereof, wherein the primer comprises at least one immobilized polyvalent metal compound for free-radically curing the curable composition; and contacting the curable composition with the primer, thereby causing at least partial curing of the curable composition. The curable composition includes at least one free-radically polymerizable compound and a beta-dicarbonyl compound. The method can be used for adhesive bonding of substrates and preparation of various articles.

Free-radical polymerization methods and articles thereby

A method of curing a free-radically polymerizable composition includes contacting a curable composition with at least one metal oxide selected from the group consisting of magnesium oxide, ferrous metal oxides, aluminum oxide, nickel oxide, silver oxide, and combinations thereof. The curable composition includes: free-radically polymerizable compound; and a beta-dicarbonyl compound represented by the formula (I) or a salt thereof, wherein: Xand Xindependently represent a covalent bond, wherein each Rindependently represents H or alkyl having from 1 to 18 carbon atoms; Rand Rindependently represent a hydrocarbyl or substituted-hydrocarbyl group having from 1 to 18 carbon atoms, and Rrepresents hydrogen, or a hydrocarbyl or substituted-hydrocarbyl group having from 1 to 18 carbon atoms, or taken together any two of R, R, or Rform a five-membered or six-membered ring; an organic peroxide; and a quaternary ammonium halide. Articles including the cured compositions are also disclosed. 

A method of curing a curable composition includes contacting the free-radically curable composition with the solid primer layer thereby causing at least partial curing of the curable composition. The solid primer layer includes a binder material, optional beta-dicarbonyl compound, and an organic peroxide. The curable composition includes at least one free-radically polymerizable compound, a polyvalent metal compound, and a quaternary ammonium halide. The method can be used for adhesive bonding of substrates and preparation of various articles.

A method of curing a free-radically polymerizable composition includes contacting a curable composition with at least one oxide of copper. The curable composition includes: free-radically polymerizable compound; and a beta-dicarbonyl compound represented by the formula (I) or a salt thereof, wherein: Rand Rindependently represent a hydrocarbyl or substituted-hydrocarbyl group having from 1 to 18 carbon atoms; Rrepresents hydrogen, or a hydrocarbyl or substituted-hydrocarbyl group having from 1 to 18 carbon atoms; and each X independently represents O, S, formula (II), or formula (III) wherein each R4 independently represents H or alkyl having from 1 to 18 carbon atoms, or taken together any two of R, R, R; or Rform a ring. Articles including the cured compositions are also disclosed. 

There is provided an adhesive composition comprising: a) at least one acrylic functional monomer; b) a first toughening agent; c) a second toughening agent; d) an adhesion promoter; and e) a high aspect ratio filler selected from at least one of a high aspect ratio fibrillated filler and a halloycite clay filler.

Growing community of inventors

Woodbury, MN, United States of America

Zachary J Thompson