Radiation-curable silicone elastomers and pressure sensitive adhesives

• US 5,475,124 A
• Filed: 05/20/1994
• Issued: 12/12/1995
• Est. Priority Date: 09/22/1989
• Status: Expired due to Term

• Current Assignee: Minnesota Mining and Manufacturing Co (3M Company)
• Original Assignee: Minnesota Mining and Manufacturing Co (3M Company)
• Inventors: Leir, Charles M., Mazurek, Mieczyslaw H., Sherman, Audrey A., Kantner, Steven S.
• Primary Examiner(s): Shaver, Paul F.
• Application Number:
  US08/247,023
• Time in Patent Office: 571 Days
• Field of Search: 556/419, 556/420, 556/421, 556/425, 556/440, 556/488
• US Class Current: 556/419
• CPC Class Codes: C07F 7/0838 Compounds with one or more Si-O-Si sequences compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21
• CPC Class Codes: C07F 7/12 Organo silicon halides
• CPC Class Codes: C08F 299/08 from polysiloxanes
• CPC Class Codes: C08G 77/26 nitrogen-containing groups
• CPC Class Codes: C08G 77/388 containing nitrogen
• CPC Class Codes: C09J 155/005 Homopolymers or copolymers obtained by polymerisation of macromolecular compounds terminated by a carbon-to-carbon double bond
• CPC Class Codes: C09J 183/08 containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
• CPC Class Codes: C09J 7/38 Pressure-sensitive adhesives [PSA]
• CPC Class Codes: Y10T 428/2809 including irradiated or wave energy treated component
• CPC Class Codes: Y10T 428/2852 Adhesive compositions
• CPC Class Codes: Y10T 428/2896 including nitrogen containing condensation polymer [e.g., polyurethane, polyisocyanate, etc.]
• CPC Class Codes: Y10T 428/31663 As siloxane, silicone or silane

Abstract

A composition which is curable to an elastomer comprising:

A polymer or mixture of polymers of the formula ##STR1## A composition which is curable to a pressure sensitive adhesive comprising the above polymer and a sufficient amount of tackifier. The invention also relates to fluorosilane compounds useful in the preparation of silicone macromonomer, their preparation and the preparation of silicone macromonomer.

Claims

1. A compound of the formula:

##STR26## wherein;

X is a monovalent moiety having ethylenic unsaturation;

Y is a divalent linking group;

m is an integer of 0 to 1;

D is a monovalent moiety selected from the group consisting of hydrogen, an alkyl group of 1 to about 10 carbon atoms, aryl, and substituted aryl;

q is an integer of 0 to 1;

R is a divalent hydrocarbon group;

R² are monovalent moieties which can be the same or different selected from the group consisting of alkyl, substituted alkyl, aryl, and substituted aryl;

s is an integer 1 to 3;

and wherein the following is true;

when q=0 and m=1, R comprises a C₃ -C₁₂ alkylene group and R² comprises methyl;

when q=0 and m=0, R comprises an alkylene group.

2. The compound of claim 1 wherein:

X comprises ##STR27## Y comprises ##STR28## q=0;

m=1;

s=1;

R comprises --CH₂ CH₂ CH₂ --; and

R² comprises --CH₃.

3. The compound of claim 1 wherein:

X comprises ##STR29## m=1;

Y comprises ##STR30## q=1;

D=H;

R comprises --CH₂ CH₂₂ CH₂ --;

R² comprises --CH₃ ; and

s=1.

4. The compound of claim 1 wherein:

X comprises CH₂ ═

CH--;

m=1;

Y comprises ##STR31## q=1;

D=H;

R comprises --CH₂ CH₂ CH₂ --;

s=1; and

R² comprises --CH₃.

5. A method of preparing a compound which comprises the steps of:

(a) combining a silane selected from the group consisting of halogen-substituted silanes, nitrogen-substituted silanes, and oxygen-substituted silanes with a suitable solvent in order to form a solution;

(b) reacting said solution with at least about a molar equivalent of an acidic fluoride in order to form a solution of a compound of the formula ##STR32## wherein;

X is a monovalent moiety having ethylenic unsaturation;

Y is a divalent linking group;

m is an integer of 0 to 1;

D is a monovalent moiety selected from the group consisting of hydrogen, an alkyl group of 1 to about 10 carbon atoms, aryl, and substituted aryl;

q is an integer of 0 to 1;

R is a divalent hydrocarbon group;

R² are monovalent moieties which can be the same or different selected from the group consisting of alkyl, substituted alkyl, aryl, and substituted aryl; and

s is an integer 1 to 3.

6. A compound of the formula ##STR33## wherein:

D is a monovalent moiety selected from the group consisting of hydrogen, an alkyl group of 1 to about 10 carbon atoms, aryl, and substituted aryl;

R is a divalent hydrocarbon group;

R² are monovalent moieties which can be the same or different selected from the group consisting of alkyl, substituted alkyl, aryl, and substituted aryl;

R³ are monovalent moieties which can be the same or different selected from the group consisting of alkyl, substituted alkyl, vinyl, aryl, and substituted aryl;

R⁴ are monovalent moieties which can be the same or different selected from the group consisting of alkyl, substituted alkyl, vinyl, aryl, and substituted aryl;

R⁷ are monovalent moieties which can be the same or different selected from the group consisting of alkyl, substituted alkyl, alkoxy, alkyl amino, hydroxyl, aryl, and substituted aryl;

s is an integer of 1 to 3; and

r is an integer of about 5 to about 1000.

7. A method of preparing the compound of the formula ##STR34## wherein:

D is a monovalent moiety selected from the group consisting of hydrogen, an alkyl group of 1 to about 10 carbon atoms, aryl, and substituted aryl;

R is a divalent hydrocarbon group;

R² are monovalent moieties which can be the same or different selected from the group consisting of alkyl, substituted alkyl, aryl, and substituted aryl;

R³ are monovalent moieties which can be the same or different selected from the group consisting of alkyl, substituted alkyl, vinyl, aryl, and substituted aryl;

R⁴ are monovalent moieties which can be the same or different selected from the group consisting of alkyl, substituted alkyl, vinyl, aryl, and substituted aryl;

R⁷ are monovalent moieties which can be the same or different selected from the group consisting of alkyl, substituted alkyl, alkoxy, alkyl amino, hydroxyl, aryl, and substituted aryl;

s is an integer of 1 to 3; and

r is an integer of about 5 to about 1000 which comprises the step of reacting a fluorosilane terminating agent represented by the formula ##STR35## wherein;

D is a monovalent moiety selected from the group consisting of hydrogen, an alkyl group of 1 to about 10 carbon atoms, aryl, and substituted aryl;

R is a divalent hydrocarbon group;

R² are monovalent moieties which can be the same or different selected from the group consisting of alkyl, substituted alkyl, aryl, and substituted aryl; and

s is an integer of 1 to 3;

with a solution of a living polymeric siloxanolate in a suitable non-hydroxylic solvent in order to form the compound.

8. The compound prepared according to the method of claim 7.