Polysiloxane urethane compounds and adhesive compositions, and method of making and using the same

• US 4,684,538 A
• Filed: 02/21/1986
• Issued: 08/04/1987
• Est. Priority Date: 02/21/1986
• Status: Expired due to Fees

• Current Assignee: Loctite Corporation (Henkel AG & Co KGaA)
• Original Assignee: Loctite Corporation (Henkel AG & Co KGaA)
• Inventors: Klemarczyk, Philip T.
• Primary Examiner(s): Marquis, Melvyn I.
• Application Number:
  US06/831,785
• Time in Patent Office: 529 Days
• Field of Search: 528/28, 428/424.2, 428/424.8, 428/428, 428/447, 427/54.1, 427/36, 427/44, 427/35
• US Class Current: 427/515
• CPC Class Codes: C08G 18/61 Polysiloxanes
• CPC Class Codes: C08G 18/672 Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
• CPC Class Codes: C08G 77/388 containing nitrogen
• CPC Class Codes: C08J 5/124 using adhesives based on a macromolecular component
• CPC Class Codes: C09J 175/16 having terminal carbon-to-carbon unsaturated bonds
• CPC Class Codes: C09J 5/06 involving heating of the applied adhesive
• CPC Class Codes: Y10T 428/31573 Next to addition polymer of ethylenically unsaturated monomer
• CPC Class Codes: Y10T 428/31587 Hydrocarbon polymer [polyethylene, polybutadiene, etc.]
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane

Abstract

Silicone urethane compounds, e.g., a polysiloxane urethane (meth)acrylate, obtained as a reaction product of a polysiloxane carbinol, a polyisocyanate, and a polyfunctional compound having at least one functional group which is reactive with an isocyanate group of the polyisocyanate and after reaction therewith provides an ethylenic functional group in the reaction product. The polysiloxane carbinol has a molecular weight of from about 5,000 to about 50,000 and has R'"'"'OH end groups wherein R'"'"' is linear C₄ -C₂₀ alkylene. Such carbinol may be obtained as a reaction product of the corresponding hydride-terminated polysiloxane and a linear C₄ -C₂₀ ω-alkenyl alcohol. The hydride-terminated polysiloxane in turn may be obtained as a reaction product of either (i) the corresponding silanol of molecular weight at least 10,000 and a hydridosilane having one or more hydrolyzable groups attached to the silicon atom, or (ii) a cyclosiloxane and a 1,3-dihydrido disiloxane.

The disclosed compounds may be utilized in adhesive compositions for substrates including bonding surfaces such as glass, and polymers and copolymers of ethylenically unsaturated monomers. The bonding of such substrates may suitably be carried out at least partially under anoxic conditions, e.g., with elevated temperature and/or actinic radiation curing of the bonding composition in a substantially oxygen-free environment. A preferred vacuum degassing/anoxic curing process is disclosed for such bonding compositions, which is particularly advantageous for difficult to bond substrates, such as low density polyethylene.

Claims

1. A method of bonding a first surface formed of polyethylene, to a second surface, comprising:

(1) applying to at least one of said first and second surfaces a composition comprising a polymerizable polysiloxane urethane compound formed as a reaction product of;

(a) a polysiloxane carbinol having a molecular weight of from about 5,000 to about 50,000, of the formula ##STR9## wherein;

each R independently is C₁ -C₈ alkyl, C₃ -C₆ cycloalkyl, or phenyl;

each R'"'"' independently is linear C₄ -C₂₀ alkylene; and

x=50-700;

(b) a polyisocyanate; and

(c) a polyfunctional compound having at least one functional group which is reactive with an isocyanate group of said polyisocyanate and after reaction therewith provides an ethylenic functional group in the reaction product;

(2) placing the first and second surfaces in bondable relationship to one another in a curing zone;

(3) establishing vacuum in said curing zone;

(4) breaking said vacuum with a gas consisting essentially of nitrogen, to provide a gas environment thereof in said curing zone; and

(5) exposing said composition to elevated temperature and/or actinic radiation for sufficient time to cure same in said gas environment in said curing zone, thereby bonding said first and second surfaces to one another.

2. A method according to claim 1, wherein said polyethylene is low density polyethylene.

3. A method according to claim 1, wherein both the first and second surfaces are formed of polyethylene.

4. A method according to claim 1, wherein both the first and second surfaces are formed of low density polyethylene.

5. A process according to claim 1, wherein the pressure in said curing zone after establishment of vacuum therein is from about 0.1 to 10 Torr.

6. An article comprising a first surface formed of polyethylene and a second surface, wherein the first and second surfaces are bonded to one another by a method according to claim 1.