Debondable adhesives and the high temperature use thereof

Patent metadata

Field	Value
Publication number	US-2018355231-A1
Application number	US-201816053920-A
Country	US
Kind code	A1
Filing date	Aug 3, 2018
Priority date	Feb 4, 2016
Publication date	Dec 13, 2018
Grant date	—

Abstract

Provided herein are debondable adhesive compositions comprising (A) one or more bis-maleimide (BMI), nadimide or itaconimide oligomer(s), (B) at least one ethylenically unsaturated co-monomer (e.g. co-monomers selected from the group consisting of acrylates, methacrylates, vinyl ethers, vinyl esters, styrenic compounds, allyl compounds, polybutadienes, cinnamates, crotonates, and mixtures of any two or more thereof), and (C) a photoinitiator. In another embodiment, the present invention is directed to an assembly of a substrate and a carrier for the substrate in which the debondable adhesive composition temporarily bonds the substrates, and a method for fabricating the assembly. The debondable adhesive compositions maintain their adhesion at temperatures of 300° C. or greater, are easily and cleanly debondable at ambient conditions, permit temporary bonding at high processing conditions, and do not compromise handling or performance of the substrates.

First claim

That which is claimed is:

1 . A method of making a debondable assembly, said method comprising:
forming an assembly by bringing a substrate and a carrier in contact with one another, separated only by an aliquot of a debondable adhesive composition; and thereafter curing the resulting assembly under conditions suitable to promote adhesion therebetween,
wherein said substrate is a fragile material;
wherein said carrier imparts structural integrity to said substrate upon bonding thereto;
wherein said debondable adhesive composition comprises:
in the range of about 10 up to 95 wt % of one or more bis-maleimide, nadimide or itaconimide oligomer(s);
in the range of about 5 up to 90 wt % of at least one ethylenically unsaturated co-monomer;
optionally a reactive organic diluent, which, when present, is present in the range of about 1 up to 50 wt %;
optionally a non-reactive organic diluent, which, when present, is present in the range of about 5 up to 40 wt %; and
optionally a photoinitiator;

wherein said composition is further characterized by one or more of the following:
said composition is stable to a temperature of at least 200° C.,
said composition is chemically resistant to acids, bases and solvents,
said composition undergoes low level of shrinkage upon curing thereof,
said composition has high adhesion to suitable substrates, especially at elevated temperatures,
said composition is heat and/or light curable, and
said composition is debondable at or about room temperature.

2 . The method of claim 1 wherein said maleimide, nadimide or itaconimide, has the structure:

respectively, wherein:
m is 1-15,
p is 0-15,
each R 2 is independently selected from hydrogen or lower alkyl (such as C 1-5 ), and
J is a monovalent or a polyvalent radical comprising organic or organosiloxane radicals, and
combinations of two or more thereof.

3 . The method of claim 2 wherein J is a monovalent or polyvalent radical selected from:
hydrocarbyl or substituted hydrocarbyl species typically having in the range of about 6 up to about 500 carbon atoms, where the hydrocarbyl species is selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, alkylaryl, arylalkyl, aryalkenyl, alkenylaryl, arylalkynyl or alkynylaryl, provided, however, that X can be aryl only when X comprises a combination of two or more different species;
hydrocarbylene or substituted hydrocarbylene species typically having in the range of about 6 up to about 500 carbon atoms, where the hydrocarbylene species are selected from alkylene, alkenylene, alkynylene, cycloalkylene, cycloalkenylene, arylene, alkylarylene, arylalkylene, arylalkenylene, alkenylarylene, arylalkynylene or alkynylarylene,
heterocyclic or substituted heterocyclic species typically having in the range of about 6 up to about 500 carbon atoms,
polysiloxane, or
polysiloxane-polyurethane block copolymers, as well as

combinations of one or more of the above with a linker selected from covalent bond, —O—, —S—, —NR—, —NR—C(O)—, —NR—C(O)—O—, —NR—C(O)—NR—, —S—C(O)—, —S—C(O)—O—, —S—C(O)—NR—, —O—S(O) 2 —, —O—S(O) 2 —O—, —O—S(O) 2 —NR—, —O—S(O)—, —O—S(O)—O—, —O—S(O)—NR—, —O—NR—C(O)—, —O—NR—C(O)—O—, —O—NR—C(O)—NR—, —NR—O—C(O)—, —NR—O—C(O)—O—, —NR—O—C(O)—NR—, —O—NR—C(S)—, —O—NR—C(S)—O—, —O—NR—C(S)—NR—, —NR—O—C(S)—, —NR—O—C(S)—O—, —NR—O—C(S)—NR—, —O—C(S)—, —O—C(S)—O—, —O—C(S)—NR—, —NR—C(S)—, —NR—C(S)—O—, —NR—C(S)—NR—, —S—S(O) 2 —, —S—S(O) 2 —O—, —S—S(O) 2 —NR—, —NR—O—S(O)—, —NR—O—S(O)—O—, —NR—O—S(O)—NR—, —NR—O—S(O) 2 —, —NR—O—S(O) 2 —O—, —NR—O—S(O) 2 —NR—, —O—NR—S(O)—, —O—NR—S(O)—O—, —O—NR—S(O)—NR—, —O—NR—S(O) 2 —O—, —O—NR—S(O) 2 —NR—, —O—NR—S(O) 2 —, —O—P(O)R 2 —, —S—P(O)R 2 —, or —NR—P(O)R 2 —; where each R is independently hydrogen, alkyl or substituted alkyl.

4 . The method of claim 2 wherein J is oxyalkyl, thioalkyl, aminoalkyl, carboxylalkyl, oxyalkenyl, thioalkenyl, aminoalkenyl, carboxyalkenyl, oxyalkynyl, thioalkynyl, aminoalkynyl, carboxyalkynyl, oxycycloalkyl, thiocycloalkyl, aminocycloalkyl, carboxycycloalkyl, oxycloalkenyl, thiocycloalkenyl, aminocycloalkenyl, carboxycycloalkenyl, heterocyclic, oxyheterocyclic, thioheterocyclic, aminoheterocyclic, carboxyheterocyclic, oxyaryl, thioaryl, aminoaryl, carboxyaryl, heteroaryl, oxyheteroaryl, thioheteroaryl, aminoheteroaryl, carboxyheteroaryl, oxyalkylaryl, thioalkylaryl, aminoalkylaryl, carboxyalkylaryl, oxyarylalkyl, thioarylalkyl, aminoarylalkyl, carboxyarylalkyl, oxyarylalkenyl, thioarylalkenyl, aminoarylalkenyl, carboxyarylalkenyl, oxyalkenylaryl, thioalkenylaryl, aminoalkenylaryl, carboxyalkenylaryl, oxyarylalkynyl, thioarylalkynyl, aminoarylalkynyl, carboxyarylalkynyl, oxyalkynylaryl, thioalkynylaryl, aminoalkynylaryl or carboxyalkynylaryl, oxyalkylene, thioalkylene, aminoalkylene, carboxyalkylene, oxyalkenylene, thioalkenylene, aminoalkenylene, carboxyalkenylene, oxyalkynylene, thioalkynylene, aminoalkynylene, carboxyalkynylene, oxycycloalkylene, thiocycloalkylene, aminocycloalkylene, carboxycycloalkylene, oxycycloalkenylene, thiocycloalkenylene, aminocycloalkenylene, carboxycycloalkenylene, oxyarylene, thioarylene, aminoarylene, carboxyarylene, oxyalkylarylene, thioalkylarylene, aminoalkylarylene, carboxyalkylarylene, oxyarylalkylene, thioarylalkylene, aminoarylalkylene, carboxyarylalkylene, oxyarylalkenylene, thioarylalkenylene, aminoarylalkenylene, carboxyarylalkenylene, oxyalkenylarylene, thioalkenylarylene, amino alkenylarylene, carboxyalkenylarylene, oxyarylalkynylene, thioarylalkynylene, amino arylalkynylene, carboxy arylalkynylene, oxyalkynylarylene, thioalkynylarylene, aminoalkynylarylene, carboxyalkynylarylene, heteroarylene, oxyheteroarylene, thioheteroarylene, aminoheteroarylene, carboxyheteroarylene, heteroatom-containing di- or polyvalent cyclic moiety, oxyheteroatom-containing di- or polyvalent cyclic moiety, thioheteroatom-containing di- or polyvalent cyclic moiety, aminoheteroatom-containing di- or polyvalent cyclic moiety, or a carboxyheteroatom-containing di- or polyvalent cyclic moiety.

5 . The method of claim 1 wherein said maleimide, nadimide or itaconimide is selected from the group consisting of:

as well as mixtures of any two or more thereof.

6 . The method of claim 1 wherein said maleimide, nadimide or itaconimide is an imide-extended, low molecular weight bis-maleimide oligomer having the structure:

7 . The method of claim 1 wherein said ethylenically unsaturated co-monomer is selected from the group consisting of (meth)acrylates, vinyl ethers, vinyl esters, styrenic compounds, allyl compounds, polybutadienes, cinnamates, crotonates, and mixtures of any two or more thereof.

8 . The method of claim 7 wherein said (meth)acrylate is a monofunctional (meth)acrylate, a difunctional (meth)acrylate, a trifunctional (meth)acrylate, or a polyfunctional (meth)acrylate, as well as mixtures of any two or more thereof.

9 . The method of claim 7 wherein said vinyl ether has the structure:
CH 2 ═CH—OR

wherein R is alkyl, substituted alkyl, alkenyl, substituted alkenyl, aryl, or substituted aryl.

10 . The method of claim 7 wherein said vinyl ester has the structure:
CH 2 ═CH—O—C(O)—R′

or
CH 2 ═CH—C(O)—O—R′

wherein R′ is alkyl or s

Assignees

• Henkel IP & Holding GmbH

Inventors

• Litke Alan E
• Issari Bahram
• Sridhar Laxmisha

Classifications

• C09J2479/08

  polyimide · CPC title

• C09J179/08 Primary

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title

• B32B37/1207

  Heat-activated adhesive (B32B37/04 takes precedence) · CPC title

• B32B38/0036

  Heat treatment (for heating or cooling of layers during lamination B32B37/06, B32B37/08) · CPC title

• C09J2433/00

  Presence of (meth)acrylic polymer · CPC title