Process for the assembly of glass devices subjected to high temperatures, compositions therefor and novel polymers for rheological control of such compositions

• US 6,132,548 A
• Filed: 12/30/1998
• Issued: 10/17/2000
• Est. Priority Date: 10/01/1996
• Status: Expired due to Fees

• Current Assignee: Loctite Corporation (Henkel AG & Co KGaA)
• Original Assignee: Loctite Corporation (Henkel AG & Co KGaA)
• Inventors: Woods, John G., Burdzy, Matthew P., Malofsky, Bernard M., Masterson, Maria L.
• Primary Examiner(s): Berman, Susan W.
• Application Number:
  US09/222,665
• Time in Patent Office: 657 Days
• Field of Search: 349/153, 349/182, 349/183, 349/193, 156/272.2, 156/275.3, 156/275.5, 156/275.2, 522/31, 522/32, 522/63, 522/68, 522/120, 522/150, 522/160, 522/113, 522/121, 522/129, 525/242, 525/312, 525/245, 525/255, 525/260, 525/261, 525/313, 525/495
• US Class Current: 156/275.5
• CPC Class Codes: C08F 12/24 Phenols or alcohols
• CPC Class Codes: C08F 8/02 Alkylation

Abstract

Cationically curable adhesives and sealants with increased viscosities and improved rheological control and good storage stability are prepared using a cationically curable monomer and a thickening polymer which is the alkylation reaction product of poly(4-hydroxystyrene) or poly(2-hydroxystyrene) with a compound RX where R is allyl, methallyl, crotyl or prenyl and X is Cl, Br or I. The cationically curable monomer suitably includes at least one alkenyloxystyrene monomer. Such thickened adhesives are useful as edge sealants for flat panel display devices. A-stage curing of the adhesive with UV irradiation allows for near ambient temperature fixturing of the device assemblies and B-stage thermal curing of the adhesive can be conducted at much lower temperatures than are needed for glass frit sealants. The B-stage cured products have thermal resistance, outgassing and substrate adhesion properties adequate for flat panel display devices.

Claims

1. A process for producing a bonded assembly from two substrate components, at least one of the substrate components being transparent to UV light, the process comprising:

applying a composition comprising;

a) a monomer component comprising at least one member selected from the group consisting of 4-allyloxystyrene, 4-methallyloxystyrene, 4-crotyloxystyrene, 4-prenyloxystyrene, 2-allyloxystyrene, 2-methallyloxystyrene, 2-crotyloxystyrene or 2-prenyloxystyrene,

b) a substantially linear polymer component having a formula consisting essentially of repeat units selected from the group consisting of ##STR5## where R₂, R₂ and R₃ are H;

or

R₁ is methyl and R₂ and R₃ are H;

or

R₁ and R₂, are H and R₃ is methyl;

or

R₁ is H and R₂ and R₃ are methyl, and

c) a cationic photoinitiator,

the polymer component being dissolved in the monomer component and the

composition being storage-stable, to at least one of the substrate components;

joining the two substrate components in desired alignment to produce ajoined assembly;

irradiating the joined assembly with UV light through said at least one transparent substrate component to polymerize said monomer component, thereby producing a fixtured assembly of the two substrate components; and

subsequently,

heating the fixtured assembly to a temperature and for a time sufficient to cause rearrangement of the polymerized composition to a colored B-stage crosslinked polymer.

2. A method as in claim 1 wherein said joined assembly is formed with a gap between the two substrate components, the composition being applied so as to form a perimeter around at least a portion of the joined assembly and thereby define an enclosed volume between said two substrate components, and wherein said enclosed volume is evacuated and sealed between said irradiation step and said heating step.

3. A method as in claim 2 wherein said bonded assembly is a flat panel display device.

4. A flat panel display device having a face plate and a base plate separated by a sealed and evacuated gap, the gap being sealed by B-stage curing of a composition comprising:

a) a monomer component comprising at least one member selected from the group consisting of 4-allyloxystyrene, 4-methallyloxystyrene, 4-crotyloxystyrene 4-prenyloxystyrene, 2-allyloxystyrene, 2-methallyloxystyrene, 2-crotyloxystyrene or 2-prenyloxystyrene, and

b) a substantially linear polymer component having a formula consisting essentially of repeat units selected from the group consisting of ##STR6## where R₁, R₂ and R₃ are H;

or

R₁ is methyl and R₂ and R₃ are H;

or

R₁ and R₂, are H and R₃ is methyl;

or

R₁ is H and R₂ and R₃ are methyl, the polymer component being dissolved in the monomer component and the composition being storage-stable.

5. A bonding process comprising:

a) applying a composition comprising a storage-stable solution of;

at least one cationically polymerizable monomer and a polymeric thickener of the formula;

##STR7## where n is an integer and R₁, R₂ and R₃ are H;

or

R₁ is methyl and R₂ and R₃ are H;

or

R₁ and R₂, are H and R₃ is methyl;

or

R₁ is H and R₂ and R₃ are methyl,

the composition further comprising a thermal or photo activated cationic initiator, to a first substrate,

b) contacting a second substrate to the composition on the first substrate to produce a joined assembly, and subsequently

c) thermally curing the composition to a B-stage polymer.

6. A bonding process as in claim 5 wherein the composition is cured to an A-stage polymer by cationic polymerization of the cationic monomer in a first curing stage, and then, in a second curing stage is thermally cured to said B-stage polymer.

7. A bonding process as in claim 6 wherein the composition is cured to said A-stage polymer by cationic thermal curing of the cationic monomer at a first time and temperature in said first curing stage, and then is cured to said B-stage polymer in said second curing stage by heating the composition to a higher temperature and/or for a longer period of time than said first curing stage.

8. A bonding process as in claim 6 wherein the joined assembly is held together with a fixturing apparatus during said first curing stage, said fixturing apparatus being removed between said first and second curing stages.

9. A bonding process as in claim 6 wherein said composition is cured to said A-stage polymer by cationic photopolymerization of the cationically polymerizable monomer.