IP Library Granted Patent US 11,492,491
Granted Patent B2
US 11,492,491 · App. 16/632,412 · Granted Nov 8, 2022

Solid siloxane polymers as delivery agents for siloxane tackifying resins

Inventors: Audrey A. Sherman (Woodbury, MN); Kiu-Yuen Tse (Woodbury, MN); Jay M. Jennen (Forest Lake, MN); Craig E. Hamer (Woodbury, MN)
Assignee: 3M INNOVATIVE PROPERTIES COMPANY
C08L83/10C08L83/08C09J183/08C09J183/10
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Quick Facts
Patent No.
US 11,492,491
App. No.
16/632,412
Granted
Nov 8, 2022
Kind
B2
Abstract

Blend compositions include at least one polydiorganosiloxane polyoxamide copolymer, and at least 70% by weight of at least one silicone tackifying resin. The blend composition is non-tacky at room temperature up to a temperature of at least 100° C. The polydiorganosiloxane polyoxamide copolymer can be a linear or branched copolymer. The blend compositions provide solid, non-powdery, and non-tacky delivery vehicles for silicone tackifying resin.

Claims (84)

1. A blend composition comprising:

a polymeric composition comprising at least one polydiorganosiloxane polyoxamide copolymer; and

at least 70% by weight of at least one silicone tackifying resin,

wherein the blend composition is non-tacky at room temperature up to a temperature of at least 100° C.

2. The blend composition of claim 1 , wherein the at least one polydiorganosiloxane polyoxamide block copolymers comprises a linear copolymer that contains at least two repeat units of Formula I:

wherein each R 1 is independently an alkyl, haloalkyl, aralkyl, alkenyl, aryl, or aryl substituted with an alkyl, alkoxy, or halo;

each Y is independently an alkylene, aralkylene, or a combination thereof;

the subscript n is an integer of 0 to 1500;

the subscript p is an integer of 1 to 10;

G is a divalent linking group that is the residue unit of a diamine of formula R 3 HN-G-NHR 3 minus the two —NHR 3 groups;

R 3 is hydrogen or alkyl having 1 to 10 carbon atoms, or R 3 taken together with G and with the nitrogen to which they are both attached form a heterocyclic group; and

each asterisk (*) indicates a site of attachment of the repeat unit to another group in the copolymer.

3. The blend composition of claim 2 , wherein the polydiorganosiloxane polyoxamide block copolymer comprising a linear copolymer that contains at least two repeat units of Formula I, wherein each R 1 is independently an alkyl having 1-3 carbon atoms;

each Y is independently an alkylene having 1-5 carbon atoms;

the subscript n is an integer of 0 to 10;

the subscript p is an integer of 1 to 10;

G is a divalent linking group of an alkylene, heteroalkylene, polydiorganosiloxane, arylene, aralkylene, or a combination thereof;

each R 3 is hydrogen; and

each asterisk (*) indicates a site of attachment of the repeat unit to another group in the copolymer.

4. The blend composition of claim 1 , wherein the at least one polydiorganosiloxane polyoxamide copolymer comprises a copolymer of general Formula II:

wherein each R 1 is independently an alkyl, haloalkyl, aralkyl, alkenyl, aryl, or aryl substituted with an alkyl, alkoxy, or halo;

G is a q-valent residue unit of a polyamine of the formula G(NHR 3 ) q minus the q-NHR 3 groups;

subscript q is an integer of 2 or greater;

each R 3 is hydrogen or an alkyl having 1 to 10 carbon atoms, or R 3 taken together with G and with the nitrogen to which they are both attached forms a heterocyclic group;

each Y is independently an alkylene, aralkylene, or a combination thereof;

subscript n is independently an integer of 0 to 1500;

subscript p is an integer of 1 to 10; and

each asterisk (*) indicates a site of attachment of the repeat unit to another group in the copolymer.

5. The blend composition of claim 4 , wherein the polydiorganosiloxane polyoxamide copolymer comprising a linear copolymer that contains at least two repeat units of Formula II, wherein each R 1 is independently an alkyl having 1-3 carbon atoms;

each Y is independently an alkylene having 1-5 carbon atoms;

subscript n is an integer of 0 to 10;

subscript p is an integer of 1 to 10;

G is a q-valent linking group of an alkylene, heteroalkylene, polydiorganosiloxane, arylene, aralkylene, or a combination thereof;

subscript q is an integer of 3 or greater;

each R 3 is hydrogen; and

each asterisk (*) indicates a site of attachment of the repeat unit to another group in the copolymer.

6. The blend composition of claim 1 , wherein the at least one polydiorganosiloxane polyoxamide copolymer comprises a copolymer with at least one repeat unit of Formula II:

and at least one repeat unit of Formula III:

wherein each R 1 is independently an alkyl, haloalkyl, aralkyl, alkenyl, aryl, or aryl substituted with an alkyl, alkoxy, or halo;

G is a q-valent residue unit of a polyamine of the formula G(NHR 3 ) q minus the q-NHR 3 groups;

subscript q is an integer of 2 or greater;

each R 3 is hydrogen or an alkyl having 1 to 10 carbon atoms, or R 3 taken together with G and with the nitrogen to which they are both attached forms a heterocyclic group;

each Y is independently an alkylene, aralkylene, or a combination thereof;

subscript n is independently an integer of 0 to 1500;

subscript p is an integer of 1 to 10;

D is a polyoxyalkylene group; and

each asterisk (*) indicates a site of attachment of the repeat unit to another group in the copolymer.

7. The blend composition of claim 6 , wherein the polydiorganosiloxane polyoxamide block copolymer comprising a copolymer that contains at least one repeat unit of Formula II and at least one repeat unit of Formula III,

wherein each R 1 is independently an alkyl having 1-3 carbon atoms;

each Y is independently an alkylene having 1-5 carbon atoms;

subscript n is an integer of 0 to 10;

subscript p is an integer of 1 to 10;

G is a q-valent linking group of an alkylene, heteroalkylene, polydiorganosiloxane, arylene, aralkylene, or a combination thereof;

subscript q is an integer of 3 or greater;

each R 3 is hydrogen; and

D is a polyoxyethylene group, a polyoxypropylene group, a poly(oxyethylene-co-oxypropylene) group, or a combination thereof; and

each asterisk (*) indicates a site of attachment of the repeat unit to another group in the copolymer.

8. The blend composition of claim 1 , wherein the blend composition comprises greater than 90% by weight of at least one silicone tackifying resin.

9. The blend composition of claim 1 , wherein the at least one silicone tackifying resin comprises an MQ silicone tackifying resin, a MQD silicone tackifying resin, a MQT silicone tackifying resin, or a combination thereof.

10. The blend composition of claim 1 , wherein the at least one silicone tackifying resin comprises an MQ tackifying resin.

11. The blend composition of claim 1 , wherein the blend composition is in the form of a pellet, a rod, a flake, an ellipse, a chip or a powder crumb.

12. The blend composition of claim 1 , wherein the blend composition comprises at least one additional additive comprising a UV stabilizer, an antioxidant, an antimicrobial, a filler, a UV sensitizer, an enzyme, or an oil.

13. A method of preparing a blend composition particle comprising:

providing a polymeric composition comprising at least one polydiorganosiloxane polyoxamide copolymer;

providing at least 70% by weight of at least one silicone tackifying resin;

mixing the polymeric composition and the at least one silicone tackifying resin to form a blend composition; and

forming the blend composition into a particle, wherein the blend composition particle is non-tacky at room temperature up to a temperature of at least 100° C.

14. The method of claim 13 , wherein mixing the polymeric composition and the at least one silicone tackifying resin to form a blend composition comprises hot melt mixing.

15. The method of claim 13 , wherein mixing comprises solvent mixing, and

further comprising adding at least one solvent to the polymeric composition, the silicone tackifying resin, or both; and

wherein forming the blend composition into an article further comprises drying the formed article.

16. The method of claim 13 , wherein providing a polymeric composition comprising at least one polydiorganosiloxane polyoxamide copolymer further comprises:

forming a reactive composition which upon reaction forms the polydiorganosiloxane polyoxamide; and

reacting the reactive composition to form the polydiorganosiloxane.

17. The method of claim 13 , wherein forming the blend composition particle comprises forming pellets, rods, flakes, ellipses, chips or powder crumbs.

18. A method of using a blend composition comprising:

providing a blend composition, wherein the blend composition comprises:

a polymeric composition comprising at least one polydiorganosiloxane polyoxamide copolymer; and

at least 70% by weight of at least one silicone tackifying resin, and wherein the blend composition is non-tacky at room temperature up to a temperature of at least 100° C.;

providing a second polymeric composition comprising at least one polydiorganosiloxane polymer or copolymer, or a reactive composition that upon reaction forms a polydiorganosiloxane polymer or copolymer; and

mixing the blend composition with the second polymeric composition to form a second blend composition, wherein the second blend composition comprises less than 70% by weight of the at least one silicon tackifying resin.

19. The method of claim 18 , wherein the second blend composition comprises a pressure sensitive adhesive.

20. The method of claim 18 , wherein the second polymeric composition comprises a reactive polydiorganosiloxane fluid composition which upon polymerization forms a polydiorganosiloxane matrix or a composition comprising a polydiorganosiloxane fluid which upon exposure to an electron beam forms a polydiorganosiloxane matrix.

21. The method of claim 18 , further comprising applying UV radiation at or below the B spectral range to the second blend composition.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 1, 2024
From: 3M INNOVATIVE PROPERTIES COMPANY
To: SOLVENTUM INTELLECTUAL PROPERTIES COMPANY
Reel/Frame 066430/0295 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 20, 2020
From: SHERMAN, AUDREY A.; TSE, KIU-YUEN; JENNEN, JAY M.; HAMER, CRAIG E.
To: 3M INNOVATIVE PROPERTIES COMPANY
Reel/Frame 051553/0399 →