IP Library Granted Patent US 12,234,390
Granted Patent B2
US 12,234,390 · App. 16/000,193 · Granted Feb 25, 2025

Debondable compositions

Inventors: Shengqian Kong (Hillsborough, NJ); Yayun Liu (Franklin Park, NJ); Wenhua Zhang (Farmington, CT); Stephen Hynes (Dublin, IE); John G. Woods (Farmington, CT); Jiangbo Ouyang (Wallingford, CT); Chunyu Sun (Shanghai, CN); Bahram Issari (Glastonbury, CT)
Assignee: Henkel AG & Co. KGaA
C09J183/06B32B7/12B32B37/12B32B37/18B32B43/006C09J5/00C09J5/06B32B2310/0831B32B2457/00C08G77/12C08G77/20C09J7/35C09J131/00C09J2301/40C09J2301/414C09J2301/416C09J2301/502C09J2483/00
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Quick Facts
Patent No.
US 12,234,390
App. No.
16/000,193
Granted
Feb 25, 2025
Kind
B2
Abstract

Dual-cure compositions for use in high temperature adhesive applications, and particularly for temporarily adhesively attaching one substrate to another substrate, are provided. These dual-cure adhesives are silicone-based compositions that can be B-staged by exposure UV radiation to provide initial green strength, followed by a C-stage cure to give adhesives that can survive high temperature processes above 200° C., especially above 300° C., yet easy to debond afterwards to allow separation of the top and bottom substrates.

Claims (35)

1. A composition radiation curable to form a pressure sensitive adhesive, comprising:

at least one photoinitiator selected from an acyl phosphine oxide photoinitiator, an alpha-hydroxyl ketone photoinitiator and a phenylglyoxalate photoinitiator; and

a mixture of polysiloxane resins including:

a polysiloxane resin (a) having a vinylsiloxane unit, a molecular weight (Mw) of 2323 to 242352 and a structure represented by:

a polysiloxane resin (b) having at least two (meth)acrylate groups and a structure selected from at least one of:

wherein the composition is free of hydridosilane and hydridopolysiloxane; and the weight ratio of polysiloxane resin (a) to polysiloxane resin (b) in the composition is within the range of 97:3 to 40:60 and the vinyl functionality to acrylate functionality in the composition is within the range of 21:1 to 0.29:1; or the weight ratio of polysiloxane resin (a) to polysiloxane resin (b) in the composition is within the range of 99:1 to 90:10 and the vinyl functionality to acrylate functionality in the composition is within the range of 19:1 to 1.4:1.

2. The composition of claim 1 ; wherein the composition further comprises a thermal initiator.

3. The composition of claim 1 ; wherein the polysiloxane resins therein consist of polysiloxane resin (a) and polysiloxane resin (b).

4. The composition of claim 1 ; wherein:

1) the composition further comprises a thermal initiator; and

2) the polysiloxane resins therein consist of polysiloxane resin (a) and polysiloxane resin (b).

5. The composition of claim 1 wherein exposure in a photorheometer to UVA radiation at 230 mW/cm 2 for 5 minutes forms a pressure sensitive adhesive having a storage modulus (G′) of less than or equal to 3.0×10 5 Pa, at 25° C. and 1 Hz.

6. The composition of claim 1 , wherein the polysiloxane resin (a) has a mole % of vinylmethylsiloxane units in the range of 4.0-13.0%.

7. The composition of claim 1 , wherein

(i) the photoinitiator is a combination of

and further comprising 1,1-di-(t-amylperoxy)-cyclohexane as a thermal initiator, or

(ii) the photoinitiator is

and the composition further comprises 3,5-dimethyl-hexyn-3-ol.

8. The composition of claim 1 , wherein the polysiloxane resin (a) has

a mole % of vinylmethylsiloxane units in the range of 1-99%.

9. Cured reaction products of the composition of claim 1 .

10. An assembly comprising: a substrate,

a carrier, and the composition of claim 1 disposed between the carrier and the substrate.

11. A method for bonding a substrate to a carrier comprising:

(a) providing a substrate;

(b) providing a carrier;

(c) disposing the composition of claim 1 onto at least one of the substrate or the carrier;

(d) contacting the substrate and carrier so that the composition is disposed between the carrier and the substrate, forming an assembly; and

(e) radically curing the composition by

(i) exposing the assembly to radiation in the electromagnetic spectrum;

(ii) exposing the assembly to elevated temperature conditions, or

(iii) (i) followed by (ii).

12. A method for debonding a substrate from a carrier to which the substrate is adhesively bonded, comprising:

(a) providing an assembly comprising the substrate and the carrier with the composition of claim 1 therebetween; and

(b) separating the substrate from the carrier.

Assignments (7)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 14, 2025
From: HENKEL IRELAND OPERATIONS AND RESEARCH LIMITED
To: HENKEL AG & CO. KGAA
Reel/Frame 069892/0147 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 10, 2025
From: HENKEL (CHINA) CO. LTD.
To: HENKEL AG & CO. KGAA
Reel/Frame 069810/0911 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 8, 2025
From: SUN, CHUNYU
To: HENKEL (CHINA) CO. LTD.
Reel/Frame 069785/0825 →
CORRECTIVE ASSIGNMENT TO CORRECT THE CORRECT TO ADD AND INVENTOR PREVIOUSLY RECORDED AT REEL: 69562 FRAME: 416. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jan 8, 2025
From: ISSARI, BAHRAM
To: HENKEL IP & HOLDING GMBH
Reel/Frame 069849/0023 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 8, 2025
From: HYNES, STEPHEN
To: HENKEL IRELAND OPERATIONS AND RESEARCH LIMITED
Reel/Frame 069784/0730 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 12, 2024
From: KONG, SHENGQIAN; LIU, YAYUN; ZHANG, WENHUA; WOODS, JOHN G.; OUYANG, JIANGBO
To: HENKEL IP & HOLDING GMBH
Reel/Frame 069562/0416 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 22, 2022
From: HENKEL IP & HOLDING GMBH
To: HENKEL AG & CO. KGAA
Reel/Frame 059207/0627 →
Continuity (3)
Continuation PCTUS2016065713 · Dec 9, 2016
Provisional Application 62265188 · Dec 9, 2015
Related Publication 20190169478A1 · Jun 6, 2019
References Cited (36)
US 4585669A · Eckberg · 1986 [cited by examiner]
US 4908086A · Goodrich et al. · 1990 [cited by applicant]
US 5256717A · Stauffer et al. · 1993 [cited by applicant]
US 5278276A · Ohta et al. · 1994 [cited by applicant]
US 7842755B2 · Morita et al. · 2010 [cited by applicant]
US 8063143B2 · Morita et al. · 2011 [cited by applicant]
US 8092628B2 · Hong et al. · 2012 [cited by applicant]
US 9850409B2 · Zhang et al. · 2017 [cited by applicant]
US 20050089696A1 · Bosshammer · 2005 [cited by examiner]
US 20100316845A1 · Rule et al. · 2010 [cited by applicant]
US 20110318938A1 · Takeuchi et al. · 2011 [cited by applicant]
US 20130341671A1 · Ona · 2013 [cited by examiner]
US 20150137172A1 · Xing · 2015 [cited by examiner]
US 20160068720A1 · Zhang · 2016 [cited by examiner]
US 20170233514A1 · Yamamoto · 2017 [cited by examiner]
CN 1918256A · 2007 [cited by applicant]
CN 1993427A · 2007 [cited by applicant]
EP 235294A1 · 1987 [cited by applicant]
EP 2639277A1 · 2013 [cited by applicant]
JP H04136021A · 1992 [cited by applicant]
JP 2010229382A · 2010 [cited by applicant]
JP 2012140060 · 2012 [cited by examiner]
JP 2013038098A · 2013 [cited by applicant]
JP 2013203794A · 2013 [cited by applicant]
JP 2014005324A · 2014 [cited by applicant]
JP 5735446B2 · 2015 [cited by applicant]
JP 2016529342A · 2016 [cited by applicant]
JP 2016210861A · 2016 [cited by applicant]
TW 200621891A · 2006 [cited by applicant]
WO 0040648A1 · 2000 [cited by applicant]
WO WO2014019188 · 2014 [cited by examiner]
WO 2015000150A1 · 2015 [cited by applicant]
WO WO2015000150 · 2015 [cited by examiner]
WO 2015196345A1 · 2015 [cited by applicant]
Dahlquist, C. A., Creep. In Satas D., (1999), “ Handbook of Pressure Sensitive Adhesive Technology.” Warwick, RI. [cited by applicant]
Itabshi, T. et al. “High temperature resistant bonding solutions enabling thin wafer processing.” Published in Electronic Components and Technology Conference (ECTC), 2010 Proceedings 60th, 2010, pp. 1877-1880. Availabl… [cited by applicant]