IP Library Granted Patent US 10,533,117
Granted Patent B2
US 10,533,117 · App. 16/022,620 · Granted Jan 14, 2020

Adhesives and related methods

Inventors: Michael Zajaczkowski (Bellefonte, PA); Michael T. Waterman (Chardon, OH); Kyle R. Heimbach (Millmont, PA); Eric L. Bartholomew (Mill Hall, PA); Brandon S. Miller (Lock Haven, PA)
Assignee: Avery Dennison Corporation
C09J7/26C08K5/13C08K5/3442C08L23/02C08L33/00C09J4/00C09J4/06C09J5/06C09J7/38C09J123/02C09J133/00C09J133/064C09J133/08C09J133/14C08F2222/102C08F2222/1013C08F2222/1026C09J2205/114C09J2205/31C09J2400/243C09J2433/00C09J2453/00
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Quick Facts
Patent No.
US 10,533,117
App. No.
16/022,620
Granted
Jan 14, 2020
Kind
B2
Abstract

Cure in place pressure sensitive adhesive compositions are described that comprise one or more of a bodying component, a structural diluent, a radical diluent as well as additives such as crosslinkers, external catalysts, photoinitiators and stabilizers/process aids. The bodying component can be acrylic or non-acrylic.

Claims (36)

1. A cure in place liquid comprising:

5-70 wt % of a bodying component comprising a pre-polymerized acrylic backbone base polymer having a Mw of 15,000-100,000;

5-80 wt % of at least one structural diluent;

5-70 wt % of at least one radical addition diluent;

0-5.0 wt % of a first curative;

0.01-10 wt % of a second curative;

0-10 wt % of photosensitizer; and

0-10 wt % stabilizer/process aid.

2. The cure in place liquid of claim 1 wherein the first curative is an external catalyst.

3. The cure in place liquid of claim 1 wherein the second curative is a photoinitiator.

4. The cure in place liquid of claim 1 wherein each of the first curative and the second curative are activatable by at least one of radiation, heat, moisture, pressure, ultrasound, exposure to chemical agents, and combinations thereof.

5. The cure in place liquid of claim 1 wherein the pre-polymerized acrylic backbone base polymer does not contain any ethylenic unsaturation or acrylate unsaturation along the polymer chain.

6. A construction comprising:

one or more substrates; and

the cure in place liquid of claim 1 disposed on the one or more substrates.

7. A cure in place liquid comprising:

10-15 wt % of a bodying component comprising an acrylic base polymer having a Mw of 15,000-100,000;

45-60 wt % of at least one structural diluent;

30-40 wt % of at least one radical addition diluent;

0.01-2.0 wt % of a first curative;

0.01-10 wt % of a second curative;

0-10 wt % of photosensitizer; and

0-10 wt % stabilizer/process aid.

8. The cure in place liquid of claim 7 wherein the acrylic base polymer is a pre-polymerized acrylic backbone base polymer.

9. The cure in place liquid of claim 8 wherein the pre-polymerized acrylic backbone base polymer does not contain any ethylenic unsaturation or acrylate unsaturation along the polymer chain.

10. A cure in place liquid comprising:

5-70 wt % of a bodying component comprising a pre-polymerized acrylic backbone base polymer having a Mw of 15,000-100,000;

5-80 wt % of at least one structural diluent;

5-70 wt % of at least one radical addition diluent;

0-5.0 wt % of a first curative;

0.01-10 wt % of a second curative;

0-10 wt % of photosensitizer; and

0-10 wt % stabilizer/process aid, wherein the pre-polymerized acrylic backbone base polymer does not contain any ethylenic unsaturation or acrylate unsaturation along the polymer chain.

11. The cure in place liquid of claim 1 wherein the structural diluent is selected from the group consisting of 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate (S-21), Bis[(3,4-epoxycyclohexyl)methyl]adipate (S-28), difunctional bisphenol A/epichlorohydrin derived liquid epoxy resin (Epon 828), Bisphenol A epoxy resin having a weight per epoxide of 235-263 g/eq as measured by ASTM D1652 (Epon 834), beta-(3,4-epoxycyclohexyl)ethyltrimethoxysilane (A-186), gamma-glycidoxypropyltrimethoxysilane (A-187), glycidyl ester of neodecanoic acid (EP-10), isocyanate-functional urethane acrylate (Desmolux D100), isocyanate-bearing urethane acrylate (Desmolux D200), aliphatic polyisocyanate (low-viscosity hexamethylene diisocyanate (HDI) biuret) (Desmodur N3200), aliphatic polyisocyanate (hexamethylene diisocyanate (HDI) biuret) (Desmodur N100), aliphatic polyisocyanate (hexamethylene diisocyanate (HDI) trimer) (Desmodur N3300), poly(propylene oxide) (PPO) oligomer having a molecular weight (Mw) of less than 5,000 daltons, trimethylolpropane oxetane (TMPO), poly(ethylene oxide) (PEO) oligomer having a molecular weight (Mw) of less than 5,000 daltons, ethyl hexyl oxetane (2EH oxetane), difunctional oxetane, trimethylolpropane triacrylate (TMPTA) of the following formula (5), tripropyleneglycol diacrylate (TPGDA) of the following formula (6), ethoxylated bisphenol A diacrylate of the following formula (7) in which n+m=3, ethoxylated trimethylolpropane triacrylate of the following formula (8), bisphenol A diglycidyl ether diacrylate of the following formula (9), 1,2-cyclic ethers, 1,3-cyclic ethers, 1,4-cyclic ethers, anhydrides, lactones, lactams, cyclic ethers, siloxanes, oxazolines, oxalidines, and bismaleimides;

12. The cure in place liquid of claim 1 wherein the structural diluent is selected from the group consisting of 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate (S-21), Bis[(3,4-epoxycyclohexyl)methyl]adipate (S-28), difunctional bisphenol A/epichlorohydrin derived liquid epoxy resin (Epon 828), Bisphenol A epoxy resin having a weight per epoxide of 235-263 g/eq as measured by ASTM D1652 (Epon 834), beta-(3,4-epoxycyclohexyl)ethyltrimethoxysilane (A-186), gamma-glycidoxypropyltrimethoxysilane (A-187), glycidyl ester of neodecanoic acid (EP-10), isocyanate-functional urethane acrylate (Desmolux D100), isocyanate-bearing urethane acrylate (Desmolux D200), aliphatic polyisocyanate (low-viscosity hexamethylene diisocyanate (HDI) biuret) (Desmodur N3200), aliphatic polyisocyanate (hexamethylene diisocyanate (HDI) biuret) (Desmodur N100), aliphatic polyisocyanate (hexamethylene diisocyanate (HDI) trimer) (Desmodur N3300), poly(propylene oxide) (PPO) oligomer having a molecular weight (Mw) of less than 5,000 daltons, trimethylolpropane oxetane (TMPO), poly(ethylene oxide) (PEO) oligomer having a molecular weight (Mw) of less than 5,000 daltons, ethyl hexyl oxetane (2EH oxetane), difunctional oxetane, tripropyleneglycol diacrylate (TPGDA) of the following formula (6), ethoxylated bisphenol A diacrylate of the following formula (7) in which n+m=3, ethoxylated trimethylolpropane triacrylate of the following formula (8), bisphenol A diglycidyl ether diacrylate of the following formula (9), 1,2-cyclic ethers, 1,3-cyclic ethers, 1,4-cyclic ethers, anhydrides, lactones, lactams, cyclic ethers, siloxanes, oxazolines, oxalidines, and bismaleimides;

13. The cure in place liquid of claim 1 wherein the radical addition diluent is selected from the group consisting of epoxy acrylate monomer (ACE™ hydroxyl acrylate), isostearyl acrylate, heptadecyl acrylate, dicyclopentadiene acrylate, 3-ethyl-3-(methyl acrylate) oxetane (OXE-10), 3-ethyl-3-(methyl methacrylate) oxetane (OXE-30), 3,4-epoxycyclohexyl methyl methacrylate (S-100), acrylic macromer having a molecular weight (Mw) of less than 10,000 daltons, 2-acryloyloxypropyl phthalate (V2100), 1,2-cyclohexanedicarboxylic acid, mono[1-methyl-2-[(1-oxo-2-propenyl)oxy]ethyl] ester (cycloaliphatic V2100), polyalkyl methacrylate (PAMA), alkoxylated tetrahydrofurfuryl (THF) acrylate of the following formula (1), hydroxyethyl acrylate of the following formula (2), phenoxyethylacrylate of the following formula (3), tetrahydrofurfuryl acrylate (THFA or THF acrylate) of the following formula (4), and urethane acrylates having a molecular weight (Mw) of less than 2000 daltons,

Assignments (3)
CHANGE OF CORPORATE ADDRESS Recorded Feb 9, 2024
From: AVERY DENNISON CORPORATION
To: AVERY DENNISON CORPORATION
Reel/Frame 066614/0887 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE ADDRESS FROM 8080 NORTON PARKWAY, MENTOR, OHIO 44060 TO 207 GOODE AVENUE, GLENDALE, CALIFORNIA 91203 PREVIOUSLY RECORDED AT REEL: 059822 FRAME: 0817. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jul 21, 2022
From: AVERY DENNISON CORPORATION
To: AVERY DENNISON CORPORATION
Reel/Frame 060799/0698 →
CHANGE OF CORPORATE ADDRESS Recorded Apr 29, 2022
From: AVERY DENNISON CORPORATION
To: AVERY DENNISON CORPORATION
Reel/Frame 059822/0817 →
Continuity (4)
Continuation 15620774 · Jun 12, 2017
Continuation 14433901
Provisional Application 61711386 · Oct 9, 2012
Related Publication 20180305585A1 · Oct 25, 2018