IP Library Granted Patent US 12,258,495
Granted Patent B2
US 12,258,495 · App. 16/720,149 · Granted Mar 25, 2025

Adhesive composition and methods of forming the same

Inventors: Nicky Chan (Hudson, MA); Olivia Gady (Saint Martin de Jussac, FR); Choung-Houng Lai (Acton, MA); Yubo Cui (Shrewsbury, MA); James N. Gordon (Waban, MA)
Assignee: SAINT-GOBAIN PERFORMANCE PLASTICS CORPORATION
C09J151/003C08F2/50C08F220/06C08F220/1808C08F220/1811C08F236/20C08F236/22C08K5/0025C08K5/01C08K5/132C08K5/37C08K7/28C09J7/38C09J133/08C09J133/10G01R23/005G01R31/002G01R31/30G01R31/31709G01R31/31719H04L9/0866H04L9/3278C09J2203/00C09J2400/14C09J2400/22C09J2423/106C09J2423/166G01R31/31703
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,258,495
App. No.
16/720,149
Granted
Mar 25, 2025
Kind
B2
Abstract

An adhesive may include an adhesive structure and an adhesive composition. The adhesive structure may include a graft copolymer. The adhesive composition may include at least about 1 wt. % and not greater than 40 wt. % of a macromonomer component for a total weight of the adhesive composition, at least about 50 wt. % and not greater than about 98 wt. % of a (meth)acrylic based polymeric component A for a total weight of the adhesive composition, and at least about 0.1 wt. % and not greater than about 30 wt. % of a tackifier component for a total weight of the adhesive composition. The macromonomer component may have a weight-average molecular weight of at least 1000 g/mol and a glass transition temperature (Tg) of at least about 40° C. The (meth)acrylic based polymeric component A may have a glass transition temperature (Tg) of not greater than about 20° C.

Claims (24)

1. An adhesive comprising an adhesive structure and an adhesive composition, wherein the adhesive structure comprises a graft copolymer and wherein the adhesive composition comprises:

at least 1 wt. % and not greater than 40 wt. % of a macromonomer component for a total weight of the adhesive composition;

at least 50 wt. % and not greater than 90 wt. % of a (meth)acrylic based polymeric component A for a total weight of the adhesive composition; and

at least 0.1 wt. % and not greater than 30 wt. % of a tackifier component for a total weight of the adhesive composition,

wherein the macromonomer component has a weight-average molecular weight of at least 1000 g/mol,

wherein the macromonomer component has a glass transition temperature of at least 40° C., and

wherein the (meth)acrylic based polymeric component A has a glass transition temperature (Tg) of not greater than 20° C.

2. The adhesive of claim 1 , wherein the graft copolymer of the adhesive structure comprises a backbone portion and a grafted side chain portion, wherein the backbone portion comprises the (meth)acrylic based polymeric component A, and wherein the grafted side chain portion comprises the macromonomer component.

3. The adhesive of claim 1 , wherein the graft copolymer of the adhesive structure is formed via radiation initiated polymerization.

4. The adhesive of claim 1 , wherein the (meth)acrylic based polymeric component A comprises a reaction product of polymerizable material comprising:

at least 0.1 wt. % and not greater than 10 wt. % of a monomer component a1 for a total weight of the (meth)acrylic based polymeric component A, wherein the monomer component a1 comprises an ethylenically unsaturated functional monomer with a pendant hydrogen bonding group; and

at least 80 wt. % and not greater than 99 wt. % of a monomer component a2 for a total weight of the (meth)acrylic based polymeric component A, wherein the monomer component a2 comprises an ethylenically unsaturated monomer.

5. The adhesive of claim 4 , wherein the monomer component a1 comprises ethylenically unsaturated functional monomer selected from the group consisting of acid containing (meth)acrylic monomers, hydroxyl containing (meth)acrylic monomers (2-hydroxyethyl (meth) acrylate), a nitrogen containing monomer having a primary, secondary, or tertiary amino group, and a nitrogen containing monomer having a primary, secondary, or tertiary amido group.

6. The adhesive of claim 4 , wherein the monomer component a2 comprises an acrylic ester of the formula C═C(R 2 )(COOR 1 ) where R1 is a alkyl group containing 1 to 24 carbons, and R2 is H or methyl.

7. The adhesive of claim 1 , wherein the macromonomer component comprises a (meth)acrylic monomer having a pendant alicyclic functional group, wherein said macromonomer component is capable of being polymerized in a free radical polymerization process.

8. The adhesive of claim 1 , wherein the tackifier component comprises C5, C9, C5/C9, dicyclopentadiene, terpene, or their hydrogenated resins, or combinations thereof.

9. The adhesive of claim 2 , wherein the graft copolymer of the adhesive structure is formed via radiation initiated polymerization.

10. The adhesive of claim 2 , wherein the (meth)acrylic based polymeric component A comprises a reaction product of polymerizable material comprising:

at least 0.1 wt. % and not greater than 10 wt. % of a monomer component a1 for a total weight of the (meth)acrylic based polymeric component A, wherein the monomer component a1 comprises an ethylenically unsaturated functional monomer with a pendant hydrogen bonding group; and

at least 80 wt. % and not greater than 99 wt. % of a monomer component a2 for a total weight of the (meth)acrylic based polymeric component A, wherein the monomer component a2 comprises an ethylenically unsaturated monomer.

11. The adhesive of claim 2 , wherein the monomer component a1 comprises ethylenically unsaturated functional monomer selected from the group consisting of acid containing (meth)acrylic monomers, hydroxyl containing (meth)acrylic monomers, a nitrogen containing monomer having a primary, secondary, or tertiary amino group, and a nitrogen containing monomer having a primary, secondary, or tertiary amido group.

12. The adhesive of claim 11 , wherein the monomer component a2 comprises an acrylic ester of the formula C═C(R 2 )(COOR 1 ) where R1 is a alkyl group containing 1 to 24 carbons, and R2 is H or methyl.

13. The adhesive of claim 2 , wherein the macromonomer component comprises a (meth)acrylic monomer having a pendant alicyclic functional group, wherein said macromonomer component is capable of being polymerized in a free radical polymerization process.

14. The adhesive of claim 2 , wherein the tackifier component comprises C5, C9, C5/C9, dicyclopentadiene, terpene, or their hydrogenated resins, or combinations thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 23, 2020
From: CHAN, NICKY; GADY, OLIVIA; LAI, CHOUNG-HOUNG; CUI, YUBO; GORDON, JAMES N.
To: SAINT-GOBAIN PERFORMANCE PLASTICS CORPORATION
Reel/Frame 052196/0212 →
Continuity (2)
Provisional Application 62786016 · Dec 28, 2018
Related Publication 20200208027A1 · Jul 2, 2020
References Cited (338)
US 3492276A · Smith · 1970 [cited by applicant]
US 3806484A · Dargan · 1974 [cited by applicant]
US 4117235A · Taylor · 1978 [cited by applicant]
US 4414370A · Hamielec et al. · 1983 [cited by applicant]
US 4546160A · Brand et al. · 1985 [cited by applicant]
US 4726982A · Traynor et al. · 1988 [cited by applicant]
US 5006582A · Mancinelli · 1991 [cited by applicant]
US 5225470A · Mancinelli · 1993 [cited by applicant]
US 5410004A · Williams · 1995 [cited by applicant]
US 5434213A · Chen et al. · 1995 [cited by applicant]
US 5578683A · Koch et al. · 1996 [cited by applicant]
US 5602220A · Haddleston et al. · 1997 [cited by applicant]
US 5625005A · Mallya et al. · 1997 [cited by applicant]
US 5644007A · Davidson et al. · 1997 [cited by applicant]
US 5648425A · Everaerts et al. · 1997 [cited by applicant]
US 5679457A · Bergerson · 1997 [cited by applicant]
US 5686504A · Ang · 1997 [cited by applicant]
US 5691432A · Williams · 1997 [cited by applicant]
US 5703169A · Zajaczkowski et al. · 1997 [cited by applicant]
US 5710227A · Freeman et al. · 1998 [cited by applicant]
US 5731387A · Zajaczkowski · 1998 [cited by applicant]
US 5756605A · Moad et al. · 1998 [cited by applicant]
US 5804610A · Hamer et al. · 1998 [cited by applicant]
US 5804632A · Haddleton et al. · 1998 [cited by applicant]
US 5840783A · Momchilovich et al. · 1998 [cited by applicant]
US 5936026A · Huybrechts et al. · 1999 [cited by applicant]
US 5981666A · Zajaczkowski et al. · 1999 [cited by applicant]
US 6096420A · Wilhoit et al. · 2000 [cited by applicant]
US 6111027A · Wright et al. · 2000 [cited by applicant]
US 6172149B1 · Shah et al. · 2001 [cited by applicant]
US 6294591B1 · Blum et al. · 2001 [cited by applicant]
US 6329068B1 · Shah et al. · 2001 [cited by applicant]
US 6348249B2 · Meyer · 2002 [cited by applicant]
US 6376626B1 · Chiefari et al. · 2002 [cited by applicant]
US 6379791B1 · Cernohous et al. · 2002 [cited by applicant]
US 6388006B1 · Fujita et al. · 2002 [cited by applicant]
US 6388026B1 · Campbell et al. · 2002 [cited by applicant]
US 6407146B1 · Fujita et al. · 2002 [cited by applicant]
US 6417267B1 · Stockl et al. · 2002 [cited by applicant]
US 6437033B1 · Shah et al. · 2002 [cited by applicant]
US 6455634B1 · Khandpur et al. · 2002 [cited by applicant]
US 6489400B2 · Khandpur et al. · 2002 [cited by applicant]
US 6503621B1 · Ma et al. · 2003 [cited by applicant]
US 6552118B2 · Fujita et al. · 2003 [cited by applicant]
US 6552144B1 · Campbell et al. · 2003 [cited by applicant]
US 6589651B2 · Carlson et al. · 2003 [cited by applicant]
US 6605681B1 · Villalobos et al. · 2003 [cited by applicant]
US 6608143B1 · Fukuoka et al. · 2003 [cited by applicant]
US 6630239B2 · Cernohous et al. · 2003 [cited by applicant]
US 6652963B2 · Husemann et al. · 2003 [cited by applicant]
US 6657011B2 · Lau et al. · 2003 [cited by applicant]
US 6663958B2 · Husemann et al. · 2003 [cited by applicant]
US 6670417B2 · Foreman et al. · 2003 [cited by applicant]
US 6723786B2 · Husemann et al. · 2004 [cited by applicant]
US 6753079B2 · Husemann et al. · 2004 [cited by applicant]
US 6783850B2 · Takizawa et al. · 2004 [cited by applicant]
US 6784240B2 · Hasegawa et al. · 2004 [cited by applicant]
US 6828019B2 · Kong et al. · 2004 [cited by applicant]
US 6887917B2 · Yang et al. · 2005 [cited by applicant]
US 6939911B2 · Tosaki et al. · 2005 [cited by applicant]
US 6964999B1 · Nakagawa et al. · 2005 [cited by applicant]
US 6994904B2 · Joseph et al. · 2006 [cited by applicant]
US 7012114B2 · Bett et al. · 2006 [cited by applicant]
US 7129294B2 · Nakagawa et al. · 2006 [cited by applicant]
US 7262242B2 · Gielens et al. · 2007 [cited by applicant]
US 7348376B2 · Gelles · 2008 [cited by applicant]
US 7462663B2 · Kim et al. · 2008 [cited by applicant]
US 7465767B2 · Simal et al. · 2008 [cited by applicant]
US 7491758B2 · Amano et al. · 2009 [cited by applicant]
US 7649066B2 · Magnet et al. · 2010 [cited by applicant]
US 7655285B2 · Cho et al. · 2010 [cited by applicant]
US 7671134B2 · Casper · 2010 [cited by applicant]
US 7691925B2 · Amano et al. · 2010 [cited by applicant]
US 7696278B2 · Kim et al. · 2010 [cited by applicant]
US 7799853B2 · Ukei et al. · 2010 [cited by applicant]
US 7834104B2 · Nakamura et al. · 2010 [cited by applicant]
US 7927703B2 · Xia et al. · 2011 [cited by applicant]
US 7989525B2 · Amano et al. · 2011 [cited by applicant]
US 8013085B2 · Schmid et al. · 2011 [cited by applicant]
US 8034879B2 · Balk et al. · 2011 [cited by applicant]
US 8101276B2 · Paul et al. · 2012 [cited by applicant]
US 8163833B2 · Moeller et al. · 2012 [cited by applicant]
US 8318852B2 · Kim et al. · 2012 [cited by applicant]
US 8318859B2 · Amano et al. · 2012 [cited by applicant]
US 8333865B2 · Husemann et al. · 2012 [cited by applicant]
US 8404344B2 · Ukei et al. · 2013 [cited by applicant]
US 8410218B2 · Abe et al. · 2013 [cited by applicant]
US 8440304B2 · Paul et al. · 2013 [cited by applicant]
US 8557378B2 · Yamanaka et al. · 2013 [cited by applicant]
US 8710139B2 · Shigetomi · 2014 [cited by examiner]
US 8791207B2 · Steelman et al. · 2014 [cited by applicant]
US 8802785B2 · Kautz et al. · 2014 [cited by applicant]
US 8816011B2 · Kautz et al. · 2014 [cited by applicant]
US 8829117B2 · Balk et al. · 2014 [cited by applicant]
US 8846833B2 · Prenzel · 2014 [cited by applicant]
US 8895669B2 · Balk et al. · 2014 [cited by applicant]
US 8969495B2 · Hustad et al. · 2015 [cited by applicant]
US 9006362B2 · Zhu et al. · 2015 [cited by applicant]
US 9011995B2 · Park et al. · 2015 [cited by applicant]
US 9238762B2 · Schaffer et al. · 2016 [cited by applicant]
US 9290682B2 · Chen et al. · 2016 [cited by applicant]
US 9359531B2 · Sherman et al. · 2016 [cited by applicant]
US 9410028B2 · Prenzel et al. · 2016 [cited by applicant]
US 9540458B2 · Prenzel · 2017 [cited by applicant]
US 9605189B2 · Hirose et al. · 2017 [cited by applicant]
US 9701875B1 · Yarusso et al. · 2017 [cited by applicant]
US 9938433B2 · Kim et al. · 2018 [cited by applicant]
US 10144854B2 · Yoon et al. · 2018 [cited by applicant]
US 10544295B2 · Heemann et al. · 2020 [cited by applicant]
US 20010025083A1 · Stark et al. · 2001 [cited by applicant]
US 20020026020A1 · Campbell et al. · 2002 [cited by applicant]
US 20030114580A1 · Kim et al. · 2003 [cited by applicant]
US 20040010091A1 · Paquet, Jr. et al. · 2004 [cited by applicant]
US 20040022693A1 · Grady · 2004 [cited by applicant]
US 20040071919A1 · Sakurai et al. · 2004 [cited by applicant]
US 20040127638A1 · Mathew et al. · 2004 [cited by applicant]
US 20040210019A1 · Hasegawa et al. · 2004 [cited by applicant]
US 20050003094A1 · Grady et al. · 2005 [cited by applicant]
US 20050158475A1 · Bell et al. · 2005 [cited by applicant]
US 20050192394A1 · Jung et al. · 2005 [cited by applicant]
US 20050217789A1 · Eckstein et al. · 2005 [cited by applicant]
US 20050250887A1 · Yang et al. · 2005 [cited by applicant]
US 20060052563A1 · Nakagawa et al. · 2006 [cited by applicant]
US 20060057366A1 · Husemann et al. · 2006 [cited by applicant]
US 20060154097A1 · Amano et al. · 2006 [cited by applicant]
US 20070092733A1 · Yang et al. · 2007 [cited by applicant]
US 20070106011A1 · Husemann et al. · 2007 [cited by applicant]
US 20070128260A1 · Lau et al. · 2007 [cited by applicant]
US 20080176086A1 · Irifune · 2008 [cited by applicant]
US 20090082488A1 · Takeda et al. · 2009 [cited by applicant]
US 20090198016A1 · Sormani et al. · 2009 [cited by applicant]
US 20090234072A1 · Nakagawa et al. · 2009 [cited by applicant]
US 20100075129A1 · Nagasaki et al. · 2010 [cited by applicant]
US 20100101723A1 · Okamoto et al. · 2010 [cited by applicant]
US 20100120931A1 · Zajaczkowski et al. · 2010 [cited by applicant]
US 20100266837A1 · Srivatsan et al. · 2010 [cited by applicant]
US 20100285244A1 · Kho · 2010 [cited by applicant]
US 20110118372A1 · Lester et al. · 2011 [cited by applicant]
US 20110177329A1 · Xia et al. · 2011 [cited by applicant]
US 20110213091A1 · Balk et al. · 2011 [cited by applicant]
US 20110269913A1 · Balk et al. · 2011 [cited by applicant]
US 20130004768A1 · Yamagata et al. · 2013 [cited by applicant]
US 20130011672A1 · Okamoto et al. · 2013 [cited by applicant]
US 20130172511A1 · Moeller et al. · 2013 [cited by applicant]
US 20130177758A1 · Shigetomi et al. · 2013 [cited by applicant]
US 20130184383A1 · Cochran et al. · 2013 [cited by applicant]
US 20130197156A1 · Palasz et al. · 2013 [cited by applicant]
US 20140044959A1 · Joo et al. · 2014 [cited by applicant]
US 20140057091A1 · Krawinkel et al. · 2014 [cited by applicant]
US 20140323604A1 · Burmeister et al. · 2014 [cited by applicant]
US 20140329960A1 · Klots et al. · 2014 [cited by applicant]
US 20140329971A1 · Prenzel · 2014 [cited by applicant]
US 20150044457A1 · Chen et al. · 2015 [cited by applicant]
US 20150322296A1 · Keite-Telgenbuscher et al. · 2015 [cited by applicant]
US 20160083629A1 · Wang et al. · 2016 [cited by applicant]
US 20160319169A1 · Gower et al. · 2016 [cited by applicant]
US 20170002236A1 · Papenbroock et al. · 2017 [cited by applicant]
US 20170029548A1 · Kawai et al. · 2017 [cited by applicant]
US 20170198169A1 · Dimmer · 2017 [cited by applicant]
US 20170283670A1 · Yarusso et al. · 2017 [cited by applicant]
US 20190352544A1 · Lin et al. · 2019 [cited by applicant]
US 20200208024A1 · Chan et al. · 2020 [cited by applicant]
US 20200208025A1 · Cui et al. · 2020 [cited by applicant]
AU 472990B2 · 1973 [cited by applicant]
AU 2012322689A1 · 2014 [cited by applicant]
CA 1185399A · 1985 [cited by applicant]
CA 2321784A1 · 1999 [cited by applicant]
CN 1434844A · 2003 [cited by applicant]
CN 1141326C · 2004 [cited by applicant]
CN 1572852A · 2005 [cited by applicant]
CN 1260316C · 2006 [cited by applicant]
CN 101535436A · 2009 [cited by applicant]
CN 103097483A · 2013 [cited by applicant]
CN 103396741A · 2013 [cited by applicant]
CN 103524966B · 2014 [cited by applicant]
CN 104262948A · 2015 [cited by applicant]
CN 105229103A · 2016 [cited by applicant]
DE 10201220859700A1 · 2013 [cited by applicant]
EP 1433799A3 · 2004 [cited by applicant]
EP 1491604B1 · 2006 [cited by applicant]
EP 1686143A3 · 2006 [cited by applicant]
EP 1319053B1 · 2007 [cited by applicant]
EP 2268758B1 · 2013 [cited by applicant]
EP 02676975A2 · 2013 [cited by applicant]
JP S63072532A · 1988 [cited by applicant]
JP H02202571A · 1990 [cited by applicant]
JP H05017726A · 1993 [cited by applicant]
JP 2510627B2 · 1996 [cited by applicant]
JP H09505103A · 1997 [cited by applicant]
JP 3045673A · 2000 [cited by applicant]
JP 2000198853A · 2000 [cited by applicant]
JP 2002194175A · 2002 [cited by applicant]
JP 2002226590A · 2002 [cited by applicant]
JP 2002256045A · 2002 [cited by applicant]
JP 2002256226A · 2002 [cited by applicant]
JP 2008013770A · 2008 [cited by applicant]
JP 2008291071A · 2008 [cited by applicant]
JP 4215898B2 · 2009 [cited by applicant]
JP 2009249538A · 2009 [cited by applicant]
JP 2009249539A · 2009 [cited by applicant]
JP 2010150400A · 2010 [cited by applicant]
JP 2010254956A · 2010 [cited by applicant]
JP 2011026551A · 2011 [cited by applicant]
JP 2011052117A · 2011 [cited by applicant]
JP 2011184678A · 2011 [cited by applicant]
JP 201267280A · 2012 [cited by applicant]
JP 2012067279A · 2012 [cited by applicant]
JP 5021471B2 · 2012 [cited by applicant]
JP 2013018227A · 2013 [cited by applicant]
JP 2013018871A · 2013 [cited by applicant]
JP 2014162852A · 2014 [cited by applicant]
JP 2014214311A · 2014 [cited by applicant]
JP 2014533757A · 2014 [cited by applicant]
JP 2016041817A · 2016 [cited by applicant]
JP 2016523999A · 2016 [cited by applicant]
JP 2017014461A · 2017 [cited by applicant]
JP 2017025192A · 2017 [cited by applicant]
JP 2017095654A · 2017 [cited by applicant]
JP 2018123224A · 2018 [cited by applicant]
JP 2018159017A · 2018 [cited by applicant]
JP 2018193563A · 2018 [cited by applicant]
KR 20040030282A · 2004 [cited by applicant]
KR 100477938B1 · 2005 [cited by applicant]
KR 101148762B1 · 2012 [cited by applicant]
KR 101337122B1 · 2013 [cited by applicant]
KR 101348516B1 · 2014 [cited by applicant]
KR 1020170062369A · 2017 [cited by applicant]
WO 9513331A1 · 1995 [cited by applicant]
WO 9607522A1 · 1996 [cited by applicant]
WO 1999003905A1 · 1999 [cited by applicant]
WO 9964528A1 · 1999 [cited by applicant]
WO 2006033148A1 · 2006 [cited by applicant]
WO 2009117654A1 · 2009 [cited by applicant]
WO 2012128294A1 · 2012 [cited by applicant]
WO 2013059549A1 · 2013 [cited by applicant]
WO 2014163300A1 · 2014 [cited by applicant]
WO 2015041266A1 · 2015 [cited by applicant]
WO 2015175963A1 · 2015 [cited by applicant]
WO 2016000938A1 · 2016 [cited by applicant]
WO 2016109173A1 · 2016 [cited by applicant]
WO 2016109174A1 · 2016 [cited by applicant]
WO 2016109176A1 · 2016 [cited by applicant]
WO 2016109245A1 · 2016 [cited by applicant]
WO 2016130504A1 · 2016 [cited by applicant]
WO 2016142422A1 · 2016 [cited by applicant]
WO 2017123488A1 · 2017 [cited by applicant]
WO 2018101252A1 · 2018 [cited by applicant]
WO 2020139672A1 · 2020 [cited by applicant]
WO 2020139674A1 · 2020 [cited by applicant]
Heuts et al., Catalytic Chain Transfer Polymerization: an Overview, Australian Journal of Chemistry, 55, 6-7 Spec., 381-398, 2002. (Abstract only). [cited by applicant]
Gibson et al., Polymerization of Methyl Methacrylate Using Four-Coordinate (α-Diimine)Iron Catalysts: Atom Transfer Radical Polymerization vs Catalytic Chain Transfer, Macromolecules, 36, 8, 2591-2593, 2003. (1st page). [cited by applicant]
Allan et al., Organometallic Mediated Radical Polymerization, Progress in Polymer Science (Oxford), 37, 1, 127-156, 2012. (Abstract only). [cited by applicant]
Debuigne et al., Cobalt-Mediated Radical Polymerization of Acrylonitrile: Kinetics Investigations and DFT Calculations, Chemistry—A European Journal, 14, 25, 7623-7637, 2008. (Abstract only). [cited by applicant]
Heuts et al., Reversible Cobalt-Carbon Bond Formation in Catalytic Chain Transfer Polymerization, Macromolecules, 32, 8, 2511-2519, 1999. (Abstract only). [cited by applicant]
Suddaby et al., Catalytic Chain Transfer for Molecular Weight Control in the Emulsion Polymerization of Methyl Methacrylate and Methyl Methacrylate-Styrene, Macromolecules, 29, 25, 8083-8091, 1996. (Abstract only). [cited by applicant]
Sanayei et al., Catalytic Chain-Transfer in Polymerization of Methyl Methacrylate. I. Chain-Length Dependence of Chain-Transfer Coefficient, Journal of Macromolecular Science: Part A—Chemistry, 26, 8, 1137-1149, 1989. (… [cited by applicant]
Haddleton et al., Radical-Addition-Fragmentation and Co-Polymerization of Methyl Methacrylate Macromonomers From Catalytic Chain Transfer Polymerization (CCTP), Polymer, 38, 25, 6207-6217, 1997. (Abstract only). [cited by applicant]
Sherwood et al., Controlled Radical Polymerisation of Methyl Acrylate Initiated by a Well- Defined Cobalt Alkyl Complex, Chemical Communications, 46, 14, 2456-2458, 2010. (Abstract only). [cited by applicant]
Neugebauer et al., Atom Transfer Radical Copolymerization of Glycidyl Methacrylate and Methyl Methacrylate, Journal of Applied Polymer Science, 124, 3, 2209-2215, 2012. (Abstract only). [cited by applicant]
Pierik, Catalytic Chain Transfer Copolymerization of Methyl Methacrylate and Butyl Acrylate, Macromolecular Chemistry and Physics, 204, 11, 1406-1418, 2003. (Abstract only). [cited by applicant]
Pierik, Catalytic Chain Transfer Copolymerization of Methyl, Methacrylate and Methyl Acrylate, Macromolecular Symposia, 165, 19-27, 2001. (Abstract only). [cited by applicant]
Datta et al., Atom Transfer Radical Polymerization of Hexyl Aerylate and Preparation of Its “All-Acrylate” Block Copolymers, Journal of Polymer Science, Part A: Polymer Chemistry, 46, 11, 3499-3511, 2008. (Abstract only… [cited by applicant]
Martchenko et al., Catalytic Chain Transfer in Polymerization of Acrylamide, European Polymer Journal, 33, 5, 713-718, 1997. (Abstract only). [cited by applicant]
Suddaby et al., Catalytic Chain Transfer in Polymerization of Methyl Methacrylate. II. Continuous Synthesis and Purification of Macromer, Journal of Applied Polymer Science, 43, 8, 1565-1575, 1991. (Abstract only). [cited by applicant]
Buchmeiser et al., Co(ACAC) 2-Mediated Radical Polymerization of Acrylonitrile: Control Over Molecular Weights and Copolymerization With Methyl Methacrylate, Macromolecular Materials and Engineering, 297, 9, 894-901, 20… [cited by applicant]
Pierik et al., High-Conversion Catalytic Chain Transfer Polymerization of Methyl Methacrylate, Journal of Applied Polymer Science, 91, 3, 1375-1388, 2004. (Abstract only). [cited by applicant]
Slavin et al., Cobalt-Catalyzed Chain Transfer Polymerization: a Review, Polymer Science: A Comprehensive Reference, 10 Volume Set, 3, 249-275, 2012. (Abstract only). [cited by applicant]
Bao et al., New Cobalt-Mediated Radical Polymerization (CMRP) of Methyl Methacrylate Initiated by Two Single-Component Dinuclear Î [cited by applicant]
Nurumbetov et al., Methacrylic Block Copolymers by Sulfur Free Raft (SF Raft) Free Radical Emulsion Polymerisation, Polymer Chemistry, 8, 6, 1084-1094, 2017. (Abstract only). [cited by applicant]
Bakac et al., Characterization of the structure, properties, and reactivity of a cobalt(II) macrocyclic complex, Inorganic Chemistry, 1986, 25, 23, 4108-4114. (1st page). [cited by applicant]
Grady et al., Studies of Higher Temperature Polymerization of N-Butyl Methacrylate and N-Butyl Acrylate, Macromolecular Symposia, 182, 149-168, 2002. (Abstract only). [cited by applicant]
Zhang et al., Preparation of PMMA-Co-PMPS Copolymers via Catalytic Chain Transfer Polymerization Techniqueand Evaluation of Their Apparent Chain Transfer Constants, Acta Polymerica Sinica, 7, 651-659, 2009. (Abstract on… [cited by applicant]
Xu et al., Progress in Pressure Sensitive Adhesives, Huaxue Fanying Gongcheng Yu Gongyi/Chemical Reaction Engineering and Technology, 31, 6, 556-565, 2015. (Abstract only). [cited by applicant]
Dong et al., Effect of Segment Structure on Mechanical Properties and Drug Release Behavior of Copolymer Pressure Sensitive Adhesives, Tianjin Daxue Xuebao (Ziran Kexue yu Gongcheng Jishu Ban)/Journal of Tianjin Univers… [cited by applicant]
Czech et al., Photoreactive UV-Crosslinkable Hotmelts Acrylic Pressure-Sensitive Adhesives Coated At Temperatures Between 80 and 120° C, Coating International, 43, 3, 26-28, 2010. (Abstract only). [cited by applicant]
Chen et al., Study on the Environmental Friendly Acrylate Pressure Sensitive Adhesive, Gaofenzi Cailiao Kexue Yu Gongcheng, 21, 6, 247-250, 2005. (Abstract only). [cited by applicant]
Ishitobi, Advanced Polymer Materials Synthesized by New Living Radical Polymerization Method (TERP), Annual Technical Conference—ANTEC, Conference Proceedings, 2458-2461, 2015. [cited by applicant]
Yoshida et al., Performance Improvement of Solvent-Type PSA, Fain Kemikaru, 43, 9, 47-52, 2014. [cited by applicant]
Ouzineb et al., Designed Nanoscale Heterogeneities for Controlling Water-Borne Pressure-Sensitive Adhesive Performance (NSHAPE), FATIPEC Congress, 29th, Recent Innovations and Future Challenges for the Coatings and Ink … [cited by applicant]
Glotfelter et al., UV Curable Monomers and Oligomers in PSA Applications, Adhesives Age, 40, 3, 50, 53-55, 1997. [cited by applicant]
Herze et al., Pressure Sensitive Adhesives Obtained by Irradiation, RADCURE '86 [Eighty Six], Conf. Proc., 10th, Dec. 29-Dec. 44, 1986. [cited by applicant]
Waterson et al., New Cobalt Catalysts for Use in Acrylic Polymerisations, American Chemical Society, Polymer Preprints, Division of Polymer Chemistry, 39, 2, 457-458, 1998. [cited by applicant]
Haddleton et al., Aqueous Solution Cobalt Mediated Catalytic Chain Transfer Polymerization, American Chemical Society, Polymer Preprints, Division of Polymer Chemistry, 40, 1, 381-382, 1999. [cited by applicant]
Steward et al., Catalytic Chain Transfer Polymerisation of Functional Methacrylates, American Chemical Society, Polymer Preprints, Division of Polymer Chemistry, 39, 2, 459-460, 1998. [cited by applicant]
Eason et al., Multifunctional Architecturally Controlled Polymeric Materials From Catalytic Chain Transfer Polymerization, American Chemical Society, Polymer Preprints, Division of Polymer Chemistry, 39, 2, 455-456, 199… [cited by applicant]
Liu et al., Backbiting and Î [cited by applicant]
Pierik et al., Shining a Light on Catalytic Chain Transfer, Macromolecular Symposia, Chapters 1-3, 182, 43-52, 2002. [cited by applicant]
Pierik et al., Shining a Light on Catalytic Chain Transfer, Macromolecular Symposia, Chapters 4-8, 182, 43-52, 2002. [cited by applicant]
International Search Report and Written Opinion for PCT/US2019/067335, mailed May 1, 2020, 12 pages. [cited by applicant]
International Search Report and Written Opinion for PCT/US2019/067333, mailed May 1, 2020, 10 pages. [cited by applicant]
International Search Report and Written Opinion for PCT/US2019/067329, mailed May 1, 2020, 12 pages. [cited by applicant]
Hamzehlou et al., Analyzing the Discrepancies in the Activation Energies of the Backbiting and Î [cited by applicant]
Liu et al., Thermally Induced Aerobic Autopolymerization of Methyl Methacrylate in Amide-Type Solvents: Simultaneous Polymerization During Induction via Direct In Situ O2 Activation, Macromolecular Chemistry and Physics… [cited by applicant]
Liu et al., Modeling Spin-Forbidden Monomer Self-Initiation Reactions in Spontaneous Free-Radical Polymerization of Acrylates and Methacrylates, Journal of Physical Chemistry A, 118, 40, 9310-9318, 2014. (Abstract only). [cited by applicant]
Moghadam et al., Computational Study of Chain Transfer to Monomer Reactions in High-Temperature Polymerization of Alkyl Acrylates, Journal of Physical Chemistry A, 117, 12, 2605-2618, 2013. [cited by applicant]
Liu et al., Computational Study of Cyclohexanone-Monomer Co-Initiation Mechanism in Thermal Homo-Polymerization of Methyl Acrylate and Methyl Methacrylate, Journal of Physical Chemistry A, 116, 22, 5337-5348, 2012. (Abs… [cited by applicant]
Katzer et al., Thermal Polymerization of Styrene, Part 1—Bulk Polymerization, Macromolecular Reaction Engineering, 6, 5, 213-224, 2012. (Abstract only). [cited by applicant]
Rier et al., Macroscopic Mechanistic Modeling and Optimization of a Self-Initiated High-Temperature Polymerization Reactor, 5991445, 2011. [cited by applicant]
Srinivasan et al., Computational Evidence for Self-Initiation in Spontaneous High-Temperature Polymerization of Methyl Methacrylate, Journal of Physical Chemistry A, 115, 6, 1125-1132, 2011. (Abstract only). [cited by applicant]
Srinivasan et al., Self-Initiation Mechanism in Spontaneous Thermal Polymerization of Ethyl and N-Butyl Acrylate: A Theoretical Study, Journal of Physical Chemistry A, 114, 30, 7975-7983, 2010. (Abstract only). [cited by applicant]
Srinivasan et al., Understanding Kinetics of Spontaneous Thermal Polymerization of Alkyl Acrylates: an Experimental Study, 2008. (Abstract only). [cited by applicant]
Hart-Smith et al., Living Star Polymer Formation: Detailed Assessment of Poly(Acrylate) Radical Reaction Pathways via ESI-MS, Macromolecules, 41, 9, 3023-3041, 2008. (Abstract only). [cited by applicant]
Jachuck et al., Continuous Photopolymerization of N-Butyl Acrylate Using a Narrow Channel Reactor, Macromolecules, 41, 9, 3053-3062, 2008. (Abstract only). [cited by applicant]
Rantow et al., Global Parametric Identifiability of Mechanistic Models in Chain Polymerization, 2006, 1657188, 2006. (Abstract only). [cited by applicant]
Rantow et al., Spontaneous Polymerization and Chain Microstructure Evolution in High-Temperature Solution Polymerization of N-Butyl Acrylate, Polymer, 47, 4, 1423-1435, 2006. (Abstract only). [cited by applicant]
Quan et al., High-Temperature Homopolymerization of Ethyl Acrylate and N-Butyl Acrylate: Polymer Characterization, Macromolecules, 38, 18, 7619-7628, 2005. (Abstract only). [cited by applicant]
Rantow et al., Optimal Control of a High-Temperature Semi-Batch Solution Polymerization Reactor, 5, ThC08.2, 2005. (Abstract only). [cited by applicant]
Peck et al., Secondary Reactions in the High-Temperature Free Radical Polymerization of Butyl Acrylate, Macromolecules, 37, 16, 5944-5951, 2004. (Abstract only). [cited by applicant]
Barner-Kowollik et al., Probing Mechanistic Features of Conventional, Catalytic and Living Free Radical Polymerizations Using Soft Ionization Mass Spectrometric, Polymer, 45, 23, 7791-7805, 2004, Techniques. (Abstract o… [cited by applicant]
Gallagher et al., Acrylic Triblock Copolymers Incorporating Isosorbide for Pressure Sensitive Adhesives, ACS Sustainable Chemistry and Engineering, 4, 6, 3379-3387, 2016. (Abstract only). [cited by applicant]
Callies et al., Combined Effect of Chain Extension and Supramolecular Interactions on Rheological and Adhesive Properties of Acrylic Pressure-Sensitive Adhesives, ACS Applied Materials and Interfaces, 8, 48, 33307-33315… [cited by applicant]
Ingale et al., Effect of Molecular Weight on Performance Properties of Pressure-Sensitive Adhesive of Poly (2-Ethylhexyl Acrylate) Synthesized by Raft-Mediated Miniemulsion Polymerization, Journal of Adhesion, 92, 3, 23… [cited by applicant]
Saindane et al., Influence of Dioctyl Maleate Concentration on Performance Behavior of Water Based Pressure-Sensitive Adhesives via Reversible Addition†Fragmentation Chain Transfer Emulsion Polymerization, Journal of … [cited by applicant]
Nasiri et al., Sustainable Glucose-Based Block Copolymers Exhibit Elastomeric and Adhesive Behavior, Polymer Chemistry, 7, 33, 5233-5240, 2016. (Abstract only). [cited by applicant]
Gridnev et al., Catalytic Chain Transfer in Free-Radical Polymerizations, Chemical Reviews, 101, 12, 3611-3659, 2001. (1st page). [cited by applicant]
Li et al., In Situ Synthesis and Properties of Hydrogenated Rosin/Polyacrylate Composite Miniemulsions-Based Pressure Sensitive Adhesives, Journal of Adhesion Science and Technology, 29, 20, 2220-2232, 2015. (Abstract o… [cited by applicant]
Gurney et al., Mechanical Properties of a Waterborne Pressure-Sensitive Adhesive With a Percolating Poly(Acrylic Acid)-Based Diblock Copolymer Network: Effect of pH, Journal of Colloid and Interface Science, 448, 8-16, … [cited by applicant]
Debuigne, Overview of Cobalt-Mediated Radical Polymerization: Roots, State of the Art and Future Prospects, Progress in Polymer Science (Oxford), 34, 3, 211-239, 2009. (Abstract only). [cited by applicant]
Kajtna et al., Synthesis and Dynamic Mechanical Analysis of Nanocomposite UV Crosslinkable 100% Solid Acrylic Pressure Sensitive Adhesives, International Journal of Adhesion and Adhesives, 49, 18-25, 2014. (Abstract onl… [cited by applicant]
Khanjani et al., Emulsion Semi-Batch Terpolymerization Process Using Hybrid Emulsifiers for Synthesizing New Emulsion Pressure Sensitive Adhesives (EPSAS), Journal of Adhesion, 90, 2, 174-194, 2014. (Abstract only). [cited by applicant]
Davis et al., Cobalt-Mediated Free-Radical Polymerization of Acrylic Monomers, Trends in Polymer Science, 3, 11, 365-373, 1995. (Abstract only). [cited by applicant]
Bae et al., Adhesion Performance and Surface Characteristics of Low Surface Energy PSAS Fluorinated by UV Polymerization, Polymer Engineering and Science, 53, 9, 1968-1978, 2013. (Abstract only). [cited by applicant]
Kajtna et al., “Design of Experiments” Analysis in Study of Solventless UV Crosslinkable Acrylic Pressure Sensitive Adhesives, International Journal of Adhesion and Adhesives, 41, 152-159, 2013. (Abstract only). [cited by applicant]
Bae et al., Adhesion Performance and Thermal Stability of Fluorinated PSAS as a Crosslinking System, Journal of Adhesion Science and Technology, 26, 1-3, 361-379, 2012. (Abstract only). [cited by applicant]
Haddleton et al., “Identifying the Nature of the Active Species in the Polymerization of Methacrylates: Inhibition of Methyl Methacrylate Homopolymerizations and Reactivity Ratios for Copolymerization of Methyl Methacry… [cited by applicant]
Sato et al., Facile Synthesis of Main-Chain Degradable Block Copolymers for Performance Enhanced Dismantlable Adhesion, ACS Applied Materials and Interfaces, 4, 4, 2057-2064, 2012. (Abstract only). [cited by applicant]
Inui et al., Pressure-Sensitive Adhesion System Using Acrylate Block Copolymers in Response to Photoirradiation and Postbaking as the Dual External Stimuli for On-Demand Dismantling, ACS Applied Materials and Interfaces… [cited by applicant]
Kajtna et al., Solventless UV Crosslinkable Acrylic Pressure Sensitive Adhesives, International Journal of Adhesion and Adhesives, 31, 8, 822-831, 2011. (Abstract only). [cited by applicant]
Jullian et al., Structure and Rheology of Di- and Triblock Copolymers of Polystyrene and Poly(N-Butyl Acrylate), Journal of Rheology, 55, 2, 379-400, 2011. (Abstract only). [cited by applicant]
Kajtna et al., UV Crosslinkable Microsphere Pressure Sensitive Adhesives-Influence on Adhesive Properties, International Journal of Adhesion and Adhesives, 31, 1, 29-35, 2011. (Abstract only). [cited by applicant]
Jullian et al., Rheological Characterization and Molecular Modeling of Poly(N-Butyl Acrylate), Applied Rheology, 20, 3, 1-11, 2010. (Abstract only). [cited by applicant]
Czech et al., Getting on the Right Tack: How Photoinitiator Type, Amount and Curing Affect PSA Performance, European Coatings Journal, 11, 34, 36-38, 2010. (Abstract only). [cited by applicant]
Jeusette et al., Microscopic Morphology of Blends Between a New “All-Acrylate” Radial Block Copolymer and a Rosin Ester Resin for Pressure Sensitive Adhesives, European Polymer Journal, 44, 12, 3931-3940, 2008. (Abstrac… [cited by applicant]
Do et al., UV-Curing Behavior and Adhesion Performance of Polymeric Photoinitiators Blended With Hydrogenated Rosin Epoxy Methacrylate for UV-Crosslinkable Acrylic Pressure Sensitive Adhesives, European Polymer Journal,… [cited by applicant]
Simal et al., Adhesive Properties of a Radial Acrylic Block Co-Polymer With a Rosin Ester Resin, Journal of Adhesion Science and Technology, 21, 7, 559-574, 2007. (Abstract only). [cited by applicant]
Eslami et al., Morphological and Physical Properties of Triblock Copolymers of Methyl Methacrylate and 2-Ethylhexyl Methacrylate, Macromolecular Materials and Engineering, 291, 9, 1104-1118, 2006. (Abstract only). [cited by applicant]
Yamamoto et al., Synthesis and PSA Performance Study for Novel Acrylic and Butyl Acrylate Block Copolymers, International Journal of Adhesion and Adhesives, 22, 1, 37-40, 2002. (Abstract only). [cited by applicant]
Class et al., The Viscoelastic Properties of Rubber-Resin Blends. II. The Effect of Resin Molecular Weight, Journal of Applied Polymer Science, 30, 2, 815-24, 1985. (Abstract only). [cited by applicant]
Cited By (1)
US 12,522,756