IP Library › Granted Patent US 12,655,302
Granted Patent B2
US 12,655,302 · App. 18/412,781 · Granted Jun 16, 2026

Water-based compositions with long term gloss retention

Inventors: Robert W. Sandoval (Crystal Lake, IL); Matthew D. Andersson (Elgin, IL); T. Howard Killilea (North Oaks, MN); Mary Jane Hibben (Elburn, IL); Frank Cusimano (Marengo, IL); Tyler Bell (Naples, FL); Michael C. Wildman (Hoffman Estates, IL)
Assignee: SWIMC LLC
C09D4/06C08F12/08C08F18/08C08F20/06C08F20/18C09D7/48C08K5/132C08K5/3435C08K5/357C08L21/02
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 12,655,302
App. No.
18/412,781
Granted
Jun 16, 2026
Kind
B2
Abstract

Water-based coating compositions or paint having improved gloss retention, including a latex or water-dispersible polymer, a UV-VIS absorber comprising a substituted benzophenone capable of being a free radical generator, a hindered amine light stabilizer, and optionally a low-VOC coalescent provided in a preferably desired amount. A composition comprising a blend a UV-VIS absorber comprising a substituted benzophenone capable of being a free radical generator, a hindered amine light stabilizer, and a low-VOC coalescent, providing a thermally-stable coalescent that can be used in a paint formulation for gloss retention. Gloss retention of paints containing the UV-VIS absorber and hindered amine light stabilizer being markedly improved over paints that do not have both components present.

Claims (52)

1 . A method of preparing an aqueous coating composition, the method comprising:

providing a latex polymer dispersed in an aqueous medium, wherein the latex polymer comprises at least one ethylenically unsaturated monomer;

providing one or more UV-VIS absorbers, wherein the one or more UV-VIS absorbers comprises a substituted benzophenone that is capable of being a free radical generator, wherein the substituted benzophenone is phenylbis(2,4,6-trimethylbenzoyl) phosphine oxide, ethyl-2,4,6-trimethylbenzoylphenylphosphinate, 2,4,6-trimethylbenzophenone, 4-methylbenzophenone, 4-phenylbenzophenone, 2,2-dimethoxy-1,2-diphenylethanone, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-phenyl-1-propanone, isopropylthioxanthone, methyl-o-benzoyl-benzoate, methylbenzoylformate, benzoin ethyl ether, 4′-ethoxyacetophenone, 4,4-bis(diethylamino)benzophenone, 2,2-dimethoxy-2-phenylacetephenone, 2-hydroxy-2-methylpropiophenone, 2-benzyl-2-(dimethylamino)-4′-morpholinobutryophenone, 4-methylbenzophenone, benzophenone hydrazone, or a combination thereof;

providing one or more hindered amine light stabilizers;

optionally providing one or more low-VOC coalescents; and

combining the polymer, the one or more UV-VIS absorbers, the one or more hindered amine light stabilizers, and optionally the low-VOC coalescent;

wherein at least one of the following is true:

the one or more UV-VIS absorbers and the one or more hindered amine light stabilizers are present in the coating composition in a total combined weight of at least 0.5 wt-% based upon the total resin solids of the coating composition; or

the one or more UV-VIS absorbers and the one or more hindered amine light stabilizers are present in the coating composition in a weight ratio of about 1:9 to about 7:3 UV-VIS absorbers.

2 . The method of claim 1 , wherein the polymer is formed from at least two ethylenically unsaturated monomers comprising acrylic acid, C 1 -C 8 esters of acrylic acid, substituted C 1 -C 8 esters of acrylic acid, methacrylic acid, C 1 -C 8 esters of methacrylic acid, substituted C 1 -C 8 esters of methacrylic acid, styrene, α-methyl styrene, vinyl toluene, vinyl acetate, vinyl propionate, allyl methacrylate, or combination thereof.

3 . The method of claim 1 , wherein the polymer comprises a multistage latex polymer having a first stage with a Tg of about 25° C. to about 90° C. and a second stage with a Tg of about −15° C. to about 10° C., the Tg values calculated by the Fox Equation.

4 . The method of claim 1 , wherein the polymer comprises a multistage latex polymer having a first stage with a Tg that differs from a second stage with a Tg by at least about 35° C., the Tg values calculated by the Fox Equation.

5 . The method of claim 1 , wherein the polymer comprises a latex polymer having at least one Tg within a range of −20° C. to 70° C., the Tg value calculated by the Fox Equation.

6 . The method of claim 1 , wherein the polymer comprises a latex polymer having at least one Tg within a range of −15° C. to 60° C., the Tg value calculated by the Fox Equation.

7 . The method of claim 1 , wherein the polymer comprises a latex polymer having at least one Tg within a range of −10° C. to 30° C., the Tg value calculated by the Fox Equation.

8 . The method of claim 1 , wherein the polymer comprises a multistage latex polymer polymerized from a first mixture of monomers for a first stage and a second mixture of monomers for a second stage, the first mixture comprising methyl methacrylate, butyl acrylate, methacrylic acid, a ureido-functional monomer, and optionally diacetone acrylamide, and the second mixture comprising methyl methacrylate, butyl acrylate, an acid-functional ethylenically unsaturated monomer, optionally diacetone acrylamide, and a ureido-functional monomer.

9 . The method of claim 1 , wherein the polymer comprises a single stage latex polymer.

10 . The method of claim 1 , wherein the coating composition is substantially free of benzophenone.

11 . The method of claim 1 , wherein the one or more UV-VIS absorbers is capable of absorbing radiation within a range of 240-465 nm.

12 . The method of claim 1 , wherein the one or more hindered amine light stabilizers comprises a tetramethylpiperidine derivative.

13 . The method of claim 1 , wherein the coating composition is an architectural paint.

14 . The method of claim 1 , wherein the one or more UV-VIS absorbers comprises methyl-o-benzoyl-benzoate.

15 . The method of claim 1 , wherein the one or more UV-VIS absorbers comprises 2,2-dimethoxy-2-phenylacetephenone.

16 . The method of claim 1 , wherein the coating composition includes less than about 50 g/L of volatile organic compounds (VOC).

17 . The method of claim 1 , wherein the coating composition applied to a substrate and allowed to dry as a film has at least 80% gloss retention after at least 2000 hours measured by QUVA gloss retention at 60-degree gloss according to ASTM G154, cycle 1.

18 . A method of preparing an aqueous coating composition, the method comprising:

providing a latex polymer dispersed in an aqueous medium, wherein the latex polymer comprises at least one ethylenically unsaturated monomer;

providing one or more UV-VIS absorbers, wherein the one or more UV-VIS absorbers comprises a substituted benzophenone that is capable of being a free radical generator, wherein the substituted benzophenone comprises Formula (I):

wherein A is an oxygen atom or N—NH 2 ;

wherein n is 0 or 1, m is 0 or 1, and y is 0 to 5, with the proviso that n, m and y are each 0 when A is N—NH 2 ;

wherein R 1 and R 2 , if present, independently from each other comprise an organic linking group;

wherein R 3 comprises an alkanoyloxy group, C 1 -C 3 alkyl, diethylaminogroup, or a 6-membered nitrogen and oxygen-containing saturated heterocyclic group; and

wherein X is a phenyl group, hydroxy-2-methyl-propyl group, an alkanoyloxy group, or a phospine oxide group, with the proviso that when X comprises a phenyl group then the total of m, n and y is ≥1;

providing one or more hindered amine light stabilizers;

optionally providing one or more low-VOC coalescents; and

combining the polymer, the one or more UV-VIS absorbers, the one or more hindered amine light stabilizers, and optionally the low-VOC coalescent;

wherein at least one of the following is true:

the one or more UV-VIS absorbers and the one or more hindered amine light stabilizers are present in the coating composition in a total combined weight of at least 0.5 wt-% based upon the total resin solids of the coating composition; or

the one or more UV-VIS absorbers and the one or more hindered amine light stabilizers are present in the coating composition in a weight ratio of about 1:9 to about 7:3 UV-VIS absorbers.

19 . A method of preparing an aqueous coating composition, the method comprising:

providing a latex polymer dispersed in an aqueous medium, wherein the latex polymer comprises at least one ethylenically unsaturated monomer;

providing one or more UV-VIS absorbers, wherein the one or more UV-VIS absorbers comprises a substituted benzophenone that is capable of being a free radical generator, wherein the substituted benzophenone comprises Formula (II):

wherein A is an oxygen atom or N—NH 2 ;

wherein n is 0 or 1, m is 0 or 1, y is 0 to 5, and z is 0 to 5, with the proviso that n, m, y and z are each 0 when A is N—NH 2 and with the further proviso that the total of n, m, y and z is ≥1 when A is an oxygen atom;

wherein R 1 and R 2 , if present, independently from each other comprise an organic linking group;

wherein R 3 , and R 4 , if present, independently from each other an alkanoyloxy group, C 1 -C 3 alkyl, diethylaminogroup, a 6-membered nitrogen and oxygen-containing saturated heterocyclic group, or form a bridge comprising an S atom;

providing one or more hindered amine light stabilizers;

optionally providing one or more low-VOC coalescents; and

combining the polymer, the one or more UV-VIS absorbers, the one or more hindered amine light stabilizers, and optionally the low-VOC coalescent;

wherein at least one of the following is true:

the one or more UV-VIS absorbers and the one or more hindered amine light stabilizers are present in the coating composition in a total combined weight of at least 0.5 wt-% based upon the total resin solids of the coating composition; or

the one or more UV-VIS absorbers and the one or more hindered amine light stabilizers are present in the coating composition in a weight ratio of about 1:9 to about 7:3 UV-VIS absorbers.

Continuity (4)
Continuation 17111268 · Dec 3, 2020
Division 16425574 · May 29, 2019
Provisional Application 62677399 · May 29, 2018
Related Publication 20240376321A1 · Nov 14, 2024
References Cited (205)
US 3214492A · Tocker · 1965 [cited by applicant]
US 3303046A · Paul et al. · 1967 [cited by applicant]
US 3320198A · Hill · 1967 [cited by applicant]
US 3429852A · Skoultchi · 1969 [cited by applicant]
US 4064286A · Hahn · 1977 [cited by applicant]
US 4071645A · Kahn · 1978 [cited by applicant]
US 4080275A · Photis et al. · 1978 [cited by applicant]
US 4252852A · Goth · 1981 [cited by applicant]
US 4255308A · Brasen · 1981 [cited by applicant]
US 4314933A · Berner · 1982 [cited by applicant]
US 4344876A · Berner · 1982 [cited by applicant]
US 4426471A · Berner · 1984 [cited by applicant]
US 4654398A · McFadden · 1987 [cited by applicant]
US 4657832A · Pfeifer · 1987 [cited by applicant]
US 5106891A · Valet · 1992 [cited by applicant]
US 5162415A · Rehmer et al. · 1992 [cited by applicant]
US 5248805A · Boettcher et al. · 1993 [cited by applicant]
US 5385815A · Schofield et al. · 1995 [cited by applicant]
US 5609963A · Cai et al. · 1997 [cited by applicant]
US 5629365A · Razavi · 1997 [cited by applicant]
US 5705545A · Avar · 1998 [cited by applicant]
US 5780117A · Swartz · 1998 [cited by applicant]
US 5824716A · Coqueret et al. · 1998 [cited by applicant]
US 5861232A · Kanda · 1999 [cited by applicant]
US 5863998A · Cai · 1999 [cited by applicant]
US 5942368A · Akiyama et al. · 1999 [cited by applicant]
US 5990228A · Eichman et al. · 1999 [cited by applicant]
US 6258887B1 · Bardman et al. · 2001 [cited by applicant]
US 6303188B1 · Bors et al. · 2001 [cited by applicant]
US 6372340B1 · Tominaga et al. · 2002 [cited by applicant]
US 6376570B1 · Zhao et al. · 2002 [cited by applicant]
US 6488760B1 · Binns et al. · 2002 [cited by applicant]
US 6740692B2 · Weitzel et al. · 2004 [cited by applicant]
US 6762230B2 · Brandenburger et al. · 2004 [cited by applicant]
US 6843939B2 · Stretanski et al. · 2005 [cited by applicant]
US 6930141B2 · Gebhart et al. · 2005 [cited by applicant]
US 7101921B2 · Edwards et al. · 2006 [cited by applicant]
US 7138438B2 · Lauer et al. · 2006 [cited by applicant]
US 7659340B2 · Coward et al. · 2010 [cited by applicant]
US 7772318B2 · Fasano et al. · 2010 [cited by applicant]
US 7812079B2 · Brandenburger et al. · 2010 [cited by applicant]
US 7923503B2 · Takahashi et al. · 2011 [cited by applicant]
US 7923513B2 · Killilea et al. · 2011 [cited by applicant]
US 8106239B2 · Zhou et al. · 2012 [cited by applicant]
US 8110624B1 · Brandenburger et al. · 2012 [cited by applicant]
US 8378002B2 · Kyota · 2013 [cited by applicant]
US 8440751B2 · Kohnke et al. · 2013 [cited by applicant]
US 8440752B2 · Brandenburger et al. · 2013 [cited by applicant]
US 8507579B2 · Sheerin et al. · 2013 [cited by applicant]
US 8530595B2 · Hunt et al. · 2013 [cited by applicant]
US 8653180B2 · Koziski et al. · 2014 [cited by applicant]
US 8802765B2 · Yang et al. · 2014 [cited by applicant]
US 9023942B2 · Van Der Zande-De Maertelaere et al. · 2015 [cited by applicant]
US 9120936B2 · Hibben et al. · 2015 [cited by applicant]
US 9611393B2 · Hibben et al. · 2017 [cited by applicant]
US 9822275B2 · Hibben et al. · 2017 [cited by applicant]
US 10196537B2 · Sandoval et al. · 2019 [cited by applicant]
US 10221322B2 · Hibben et al. · 2019 [cited by applicant]
US 10221332B2 · Nimoto · 2019 [cited by applicant]
US 10301500B2 · Hibben et al. · 2019 [cited by applicant]
US 10421868B2 · Hibben et al. · 2019 [cited by applicant]
US 10723908B2 · Sandoval et al. · 2020 [cited by applicant]
US 10882999B2 · Hibben et al. · 2021 [cited by applicant]
US 10883012B2 · Hibben et al. · 2021 [cited by applicant]
US 10889721B2 · Sandoval et al. · 2021 [cited by applicant]
US 11312867B2 · Hibben · 2022 [cited by applicant]
US 11312879B2 · Hibben · 2022 [cited by applicant]
US 11377571B2 · Sandoval et al. · 2022 [cited by applicant]
US 11976207B2 · Hibben et al. · 2024 [cited by applicant]
US 20020026006A1 · Garcia · 2002 [cited by applicant]
US 20020151648A1 · Fasano · 2002 [cited by applicant]
US 20020156163A1 · Brandenburger et al. · 2002 [cited by applicant]
US 20020160205A1 · Garcia · 2002 [cited by applicant]
US 20030018121A1 · Weitzel et al. · 2003 [cited by applicant]
US 20030099831A1 · Fewkes et al. · 2003 [cited by applicant]
US 20040131787A1 · Fang · 2004 [cited by applicant]
US 20040192684A1 · Ravichandran · 2004 [cited by applicant]
US 20040242735A1 · McMan et al. · 2004 [cited by applicant]
US 20050009954A1 · Gebhard · 2005 [cited by applicant]
US 20050032954A1 · Brandenburger et al. · 2005 [cited by applicant]
US 20050203211A1 · Gebhard · 2005 [cited by applicant]
US 20050215678A1 · Ludtke et al. · 2005 [cited by applicant]
US 20060111503A1 · Killilea et al. · 2006 [cited by applicant]
US 20060135684A1 · Killilea et al. · 2006 [cited by applicant]
US 20070100074A1 · Devonport et al. · 2007 [cited by applicant]
US 20070110981A1 · Killilea et al. · 2007 [cited by applicant]
US 20070116866A1 · Mich · 2007 [cited by applicant]
US 20070238827A1 · Brady et al. · 2007 [cited by applicant]
US 20070248837A1 · Hsu et al. · 2007 [cited by applicant]
US 20070259986A1 · Elwakil · 2007 [cited by applicant]
US 20070282046A1 · Killilea · 2007 [cited by applicant]
US 20080058473A1 · Freidzon · 2008 [cited by applicant]
US 20080063965A1 · Lai et al. · 2008 [cited by applicant]
US 20080092776A1 · Stockl et al. · 2008 [cited by applicant]
US 20080200631A1 · Haring · 2008 [cited by applicant]
US 20090035587A1 · Killilea et al. · 2009 [cited by applicant]
US 20090149591A1 · Yang et al. · 2009 [cited by applicant]
US 20090312469A1 · Koziski et al. · 2009 [cited by applicant]
US 20090326121A1 · Stockl et al. · 2009 [cited by applicant]
US 20100015360A1 · Kyota · 2010 [cited by applicant]
US 20100178494A1 · Foster et al. · 2010 [cited by applicant]
US 20110112223A1 · Yang et al. · 2011 [cited by applicant]
US 20110245390A1 · Yang et al. · 2011 [cited by applicant]
US 20120041092A1 · Bohannon · 2012 [cited by applicant]
US 20120053260A1 · Balk et al. · 2012 [cited by applicant]
US 20120129974A1 · DeNotta et al. · 2012 [cited by applicant]
US 20120152459A1 · Avramidis · 2012 [cited by applicant]
US 20130116359A1 · Bohannon · 2013 [cited by applicant]
US 20130210985A1 · Brandenburger et al. · 2013 [cited by applicant]
US 20140256862A1 · Palmer et al. · 2014 [cited by applicant]
US 20140275315A1 · Hibben et al. · 2014 [cited by applicant]
US 20140275388A1 · Rokowski et al. · 2014 [cited by applicant]
US 20150175807A1 · Jing · 2015 [cited by applicant]
US 20150275388A1 · Yoshida et al. · 2015 [cited by applicant]
US 20160053127A1 · Hibben · 2016 [cited by applicant]
US 20160145460A1 · Bell et al. · 2016 [cited by applicant]
US 20170029654A1 · Hibben et al. · 2017 [cited by applicant]
US 20170073543A1 · Joecken et al. · 2017 [cited by applicant]
US 20170096567A1 · Brandenburger et al. · 2017 [cited by applicant]
US 20170174904A1 · Hibben et al. · 2017 [cited by applicant]
US 20170226373A1 · Reno · 2017 [cited by applicant]
US 20170247565A1 · Bell et al. · 2017 [cited by applicant]
US 20170327709A1 · Sandoval et al. · 2017 [cited by applicant]
US 20170335127A1 · Ewert et al. · 2017 [cited by applicant]
US 20180016376A1 · Belowich et al. · 2018 [cited by applicant]
US 20180148595A1 · Hibben et al. · 2018 [cited by applicant]
US 20190211224A1 · Sandoval et al. · 2019 [cited by applicant]
US 20190367740A1 · Sandoval et al. · 2019 [cited by applicant]
US 20190367765A1 · Hibben et al. · 2019 [cited by applicant]
US 20200190339A1 · Hibben et al. · 2020 [cited by applicant]
US 20200377751A1 · Sandoval et al. · 2020 [cited by applicant]
US 20210087408A1 · Sandoval et al. · 2021 [cited by applicant]
US 20210087409A1 · Hibben et al. · 2021 [cited by applicant]
US 20210108102A1 · Hibben · 2021 [cited by applicant]
US 20220340775A1 · Hibben et al. · 2022 [cited by applicant]
US 20220380621A1 · Sandoval et al. · 2022 [cited by applicant]
CA 2583718A1 · 2006 [cited by applicant]
CN 1288030A · 2001 [cited by applicant]
CN 1670096A · 2005 [cited by applicant]
CN 1833008A · 2006 [cited by applicant]
CN 1847320A · 2006 [cited by applicant]
CN 101149574A · 2008 [cited by applicant]
CN 101613514A · 2009 [cited by applicant]
CN 101952225A · 2011 [cited by applicant]
CN 102105541A · 2011 [cited by applicant]
CN 102206394A · 2011 [cited by applicant]
CN 102304262 · 2012 [cited by applicant]
CN 102307917A · 2012 [cited by applicant]
CN 103468126A · 2013 [cited by applicant]
CN 105315819 · 2016 [cited by applicant]
EP 0010000A1 · 1980 [cited by applicant]
EP 1574533A1 · 2005 [cited by applicant]
EP 1710284A1 · 2006 [cited by applicant]
EP 2133376A1 · 2009 [cited by applicant]
EP 2371913A1 · 2011 [cited by applicant]
FR 2786777A1 · 2000 [cited by applicant]
GB 1189560 · 1970 [cited by applicant]
JP 4117461A · 1992 [cited by applicant]
WO WO94000524A1 · 1994 [cited by applicant]
WO WO9958608A1 · 1999 [cited by applicant]
WO WO0006643A1 · 2000 [cited by applicant]
WO WO2002068547A1 · 2002 [cited by applicant]
WO WO2005097917A1 · 2005 [cited by applicant]
WO WO2006065914A1 · 2006 [cited by applicant]
WO WO2007087458A1 · 2007 [cited by applicant]
WO WO2010008713A1 · 2010 [cited by applicant]
WO WO2010027487 · 2010 [cited by applicant]
WO WO2011145024A2 · 2011 [cited by applicant]
WO WO2012028627A1 · 2012 [cited by applicant]
WO WO2013138209A1 · 2013 [cited by applicant]
WO WO2014149756A1 · 2014 [cited by applicant]
WO WO2016053595A1 · 2016 [cited by applicant]
WO WO2016069410A1 · 2016 [cited by applicant]
WO WO2018032410 · 2018 [cited by applicant]
“Innovative Acrylic Polymers for Architectural Coatings,” EPS® Science Simplified—Engineered Polymer Solutions, E-824387-12-BR; Apr. 2023; 8 pgs. [cited by applicant]
International Search Report and Written Opinion for PCT/US2019/034398, date mailed Sep. 16, 2019. [cited by applicant]
Koleski et al., “Additives Guide,” Paint & Coatings Industry, Apr. 2003, pp. 12-86, www.pcimag.com. [cited by applicant]
Lin, “Novel Light Stabilizers for Waterborne and Epoxy Coatings,” Dec. 31, 2013. Everlight Chemical Industrial Corporation. [cited by applicant]
Polymer Properties Database, “Hindered Amine Light Stabilizers (HALS),” https://polymerdatabase.com/polymer4AI20chemistry!HALS.html. (© 2015). [cited by applicant]
Anonymous: “Technical Data Sheet Eastman Texanol (TM) Alcohol Ester”, Dec. 1, 2017; 3 pages. [cited by applicant]
ASTM D2244-02. Standard Practice for Calculation of Color Tolerances and Color Differences from Instrumentally Measured color Coordinates. 1993. 10 pages. [cited by applicant]
ASTM D2369-90. Standard Test Method for Volatile Content of Coatings. 1990. 5 pages. [cited by applicant]
ASTM D3960-02. Standard Practice for Determining Volatile Organic Compound (VOC) Content of Paints and Related Coatings. 2002. 8 pages. [cited by applicant]
ASTM D6886-12. Standard Test Method for Determination of the Individual Volatile Organic Compounds (VOCs) in Air-Dry Coatings by Gas Chromatography. 2012. 7 pages. [cited by applicant]
Ding, [cited by applicant]
EPA, Technical Overview of Volatile Organic Compounds, 2009. [cited by applicant]
Gachter, et al., editors, [cited by applicant]
Green, W. Arthur; [cited by applicant]
“High Lights! Radiation curing with resins and photoinitiators for industrial coatings and graphic arts: Laromer®, Irgacure®, Lucirin®, Darocur®.” BASF SE, Lufwigshafen, Germany [retrieved on Aug 6, 2014]. Retrieved fro… [cited by applicant]
International Search Report (and Written Opinion (PCT/ISA/237), mailed Jun. 18, 2014, in connection with Patent Application No. PCT/US2014/020719, filed Mar. 5, 2014; 13 pgs. [cited by applicant]
International Search Report and Written Opinion mailed Jan. 6, 2016, in connection with Patent Application No. PCT/US2015/049659. 14 pages. [cited by applicant]
International Preliminary Report on Patentability, mailed Sep. 24, 2015, in connection with Patent Application No. PCT/US2014/020719, filed Mar. 5, 2014; 10 pgs. [cited by applicant]
International Preliminary Report on Patentability, mailed Mar. 23, 2017, in connection with Patent Application No. PCT/US2015/049659, filed Sep. 11, 2015; 8pgs. [cited by applicant]
International Preliminary Report on Patentability for Patent Application No. PCT/US2019/034398, mailed Dec. 10, 2020, 8pgs. [cited by applicant]
Li, Wenbin, Unknown Title, Jan. 31, 2014, China Central Television University Press, Cover, publication page, pp. 108-110. Translation not provided. See First Office Action for Chinese Patent Application No. 20158004845… [cited by applicant]
Liu, Lijun, Unknown title, Jul. 31, 2012 Heilongjiang University Press, Cover, publication page, pp. 61-62. Translation not provided. See First Office Action for Chinese Patent Application No. 201580048452.X, p. 6 of Su… [cited by applicant]
“Product Overview Additives for Architectural Coatings and Construction Chemicals”, Jun. 10, 2014 (Jun. 10, 2014), XP055122267, Retrieved from the Internet: <URL:http://www.basf.com/group/corporate/en/literature-documen… [cited by applicant]
Tang, Wanyou, “Post-press processing technology”, Oct. 31, 2001, China Light Industry Press, Cover, publication page, p. 60. Translation not provided. See Third Office Action for Chinese Patent Application No. 201580048… [cited by applicant]
Tceq, 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate, Texas Commission on Environmental Quality, 2013. [cited by applicant]
First Office Action and Search Report for Chinese Patent Application No. 201480014981.3, dated Sep. 5, 2016; 22 pages. English summary provided. [cited by applicant]
First Office Action and Search Report for Chinese Patent Application No. 201580048452.X, dated Nov. 29, 2019; 12 pages. English summary provided. [cited by applicant]
Second Office Action and Search Report for Chinese Patent Application No. 201580048452.X, dated Jul. 24, 2020; 21 pages. English summary provided. [cited by applicant]
Third Office Action and Search Report for Chinese Patent Application No. 201580048452.X, dated Dec. 10, 2020; 17 pages. English summary provided. [cited by applicant]
European Patent Application No. 15 84 7438.7, filed Mar. 9, 2017; Partial Supplementary European Search Report and Opinion issued Apr. 19, 2018; 10 pages. [cited by applicant]
First Office Action for Chinese Patent Application No. 201811032221.1, dated Aug. 21, 2020, 15 pages. [cited by applicant]