US 9,315,695 B2Granted

Actinic radiation and moisture dual curable composition

AssigneeDymax Corporation

InventorsMarufur Rahim, Aysegul Kascatan Nebioglu, Ahmet Nebioglu, Maria Fe Aton Audia

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Abstract

A dual curable, liquid adhesive composition capable of polymerization by exposure to actinic radiation and moisture. The composition is particularly useful for liquid adhesives for electronic applications. The composition comprises an alkoxysilane functional polyurethane acrylate oligomer; a free radical polymerizable reactive diluent; a free radical photoinitiator; a catalyst for moisture curing of silane groups; and an optional alkoxysilane functional oligomer having a polyolefin group; an optional acrylate or methacrylate functional polyurethane acrylate oligomer; an optional hydroxyl terminated monoacrylate or monomethacrylate functional reactive diluent; an optional UV-absorber and hindered amine light stabilizer antioxidant; an optional wax capable of reducing oxygen inhibition; an optional 1,3 dicarbonyl compound chelating agent; an optional thixotropic agent; and an optional adhesion promoter. optional adhesion promoter.

Claims22

Dependent claims

An actinic radiation and moisture dual curable composition which comprises:

(a) from about 10 to about 90 percent by weight of at least one alkoxysilane functional polyurethane acrylate oligomer having the formula (1) or (2):
A-D-(P-D)n-X (1)
A-D-(P-D)n-P—Y (2)
wherein:
i) D is a di- or tri-functional isocyanate group;
ii) P is a polyol group having a molecular weight of from about 50 Daltons to about 10000 Daltons;
iii) n is from 1 to about 100;
iv) A is a monoalcohol functional acrylate or methacrylate group;
v) X is a methoxysilane or ethoxysilane functional group containing a urea or thiourethane linkage;
vi) Y is a methoxysilane or ethoxysilane functional group containing a urethane linkage;
(b) from 0 to about 40 percent by weight of at least one alkoxysilane functional oligomer having the formula (3) or (4):
Y—(PO-D)m-PO—Y (3)
X-D-(PO-D)m-X (4)
wherein:
i) D is a di- or tri-functional isocyanate group;
ii) PO is a polyolefin group having a molecular weight of from about 300 Daltons to about 10000 Daltons;
iii) m is from 1 to about 100;
iv) X is a methoxysilane or ethoxysilane functional group containing a urea or thiourethane linkage;
v) Y is a methoxysilane or ethoxysilane functional group containing a urethane linkage;
(c) from 0 to about 40 percent by weight of at least one acrylate or methacrylate functional polyurethane acrylate oligomer having the formula (5);
A-D-(P-D)k-A (5)
wherein;
i) D is a di- or tri-functional isocyanate group;
ii) P is a polyol group having a molecular weight of from about 50 Daltons to about 10000 Daltons;
iii) k is from 1 to about 100;
iv) A is a monoalcohol functional acrylate or methacrylate group;
(d) from 0 to about 20 percent by weight of at least one hydroxyl terminated monoacrylate or monomethacrylate functional reactive diluent;
(e) from 1 to about 60 percent by weight of at least one free radical polymerizable reactive diluent;
(f) from about 0.1 to about 10 percent by weight of at least one free radical photoinitiator;
(g) from about 0.01 to about 3 percent by weight of at least one catalyst for moisture curing of silane groups;
(h) from 0 to about 3 percent by weight of a UV-absorber and hindered amine light stabilizer antioxidant;
(i) from 0 to about 15 percent by weight of a wax capable of reducing oxygen inhibition;
(j) from 0 to about 3 percent by weight of 1,3 dicarbonyl compound chelating agent;
(k) from 0 to about 10 percent by weight of a thixotropic agent;
(l) from 0 to about 10 percent by weight of an adhesion promoter.

32 more elements

A method of curing an actinic radiation and moisture dual curable composition which comprises:

A) providing an actinic radiation and moisture dual curable composition which comprises:
(a) from about 10 to about 90 percent by weight of at least one alkoxysilane functional polyurethane acrylate oligomer having the formula (1) or (2):
A-D-(P-D)n-X (1)
A-D-(P-D)n-P—Y (2)
wherein:
i) D is a di- or tri-functional isocyanate group;
ii) P is a polyol group having a molecular weight of from about 50 Daltons to about 10000 Daltons;
iii) n is from 1 to about 100;
iv) A is a monoalcohol functional acrylate or methacrylate group;
v) X is a methoxysilane or ethoxysilane functional group containing a urea or thiourethane linkage;
vi) Y is a methoxysilane or ethoxysilane functional group containing a urethane linkage;
(b) from 0 to about 40 percent by weight of at least one alkoxysilane functional oligomer having the formula (3) or (4):
Y—(PO-D)m-PO—Y (3)
X-D-(PO-D)m-X (4)
wherein:
i) D is a di- or tri-functional isocyanate group;
ii) PO is a polyolefin group having a molecular weight of from about 300 Daltons to about 10000 Daltons;
iii) m is from 1 to about 100;
iv) X is a methoxysilane or ethoxysilane functional group containing a urea or thiourethane linkage;
v) Y is a methoxysilane or ethoxysilane functional group containing a urethane linkage;
(c) from 0 to about 40 percent by weight of at least one acrylate or methacrylate functional polyurethane acrylate oligomer having the formula (5);
A-D-(P-D)k-A (5)
wherein;
i) D is a di- or tri-functional isocyanate group;
ii) P is a polyol group having a molecular weight of from about 50 Daltons to about 10000 Daltons;
iii) k is from 1 to about 100;
iv) A is a monoalcohol functional acrylate or methacrylate group;
(d) from 0 to about 20 percent by weight of at least one hydroxyl terminated monoacrylate or monomethacrylate functional reactive diluent;
(e) from 1 to about 60 percent by weight of at least one free radical polymerizable reactive diluent;
(f) from about 0.1 to about 10 percent by weight of at least one free radical photoinitiator;
(g) from about 0.01 to about 3 percent by weight of at least one catalyst for moisture curing of silane groups;
(h) from 0 to about 3 percent by weight of a UV-absorber and hindered amine light stabilizer antioxidant;
(i) from 0 to about 15 percent by weight of a wax capable of reducing oxygen inhibition;
(j) from 0 to about 3 percent by weight of 1,3 dicarbonyl compound chelating agent;
(k) from 0 to about 10 percent by weight of a thixotropic agent;
(1) from 0 to about 10 percent by weight of an adhesion promoter;
and
B) providing water to the composition;
and
C) exposing the composition to sufficient actinic radiation to at least partially polymerize or crosslink the composition.

37 more elements

Dependencies are inferred from the claim text.

Facts

Application: 14/316,152Filed 26 Jun 2014
Published: US 2015/0376476 A131 Dec 2015
Granted: 19 Apr 2016
Term ends: Not estimatedThe source records don’t support an estimate.

Classification17 codes

C09J 133/14
Homopolymers or copolymers of esters: of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
C08G 18/246
Tin salts of carboxylic acids: containing also tin-carbon bonds
C08G 18/289
Compounds containing at least one heteroatom other than oxygen or nitrogen: containing silicon
C08G 18/6204
Polymers of compounds having carbon-to-carbon double bonds: polymers of olefins