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AUTOMOTIVE CLEARCOAT AUTOMOTIVE CLEARCOAT -- ACID RESISTANCEACID RESISTANCE-- IMBRITTLEMENTIMBRITTLEMENT-- INTERCOAT ADHESIONINTERCOAT ADHESION
COIL COATING COIL COATING -- OVERBAKEOVERBAKE-- CURE WINDOWCURE WINDOW
LAMINATING LAMINATING -- FLEXIBILITYFLEXIBILITY
NETWORK STABILITYNETWORK STABILITY
NN
NN
NN
NN
NN NNCHCH22--OO--CHCH33
CHCH22--OO--CHCH33
CHCH22--OO--CHCH33
CHCH33--OO--CHCH22
CHCH33--OO--CHCH22
CHCH33--OO--CHCH22
HMMMHMMM
XX--LINK and SELFLINK and SELF--CONDENSATIONCONDENSATION
>N>N--CHCH22--OO--CHCH33 ROHROH >N>N--CHCH22--OO--RR CHCH3 3 --OHOH
>N>N--CHCH22--OO--RR HOHHOH >N>N--CHCH22--OO--HH
>N>N--CHCH22--OO--HH
>N>N--CHCH22--N<N<
CHOHCHOH>NH>NH
>N>N--CHCH22--OO--RR >NH>NH ROHROH
++
++ ROHROH
++
++
++
++ ++
HH++
HH++
HH++
XX--LINK and SELFLINK and SELF--CONDENSATIONCONDENSATION
SELFSELF--CONDENSATIONCONDENSATION
SELFSELF--CONDENSATIONCONDENSATION
SELFSELF--CONDENSATIONCONDENSATION
SELFSELF--CONDENSATIONCONDENSATION
IMPROVED NETWORKSIMPROVED NETWORKS
REDUCED MELAMINE LEVEL REDUCED MELAMINE LEVEL -- DUAL CUREDUAL CURE
BLOCKED ISOCYANATESBLOCKED ISOCYANATESKETOXIMEKETOXIMEMALONATEMALONATE
SILOXANESILOXANEEPOXYEPOXY
>N>N--CHCH22--OO--CHCH33
RR11//
>N>N--CHCH22--OO--N=CN=C\\RR22
O RO R11|| /|| /
RR--NHNH--COCO--N=CN=C\\RR22
RR11//
HOHO--N=CN=C\\RR22
RR--NCONCO ++
RR--NCONCO RR11OHOH++ RR--NHCOORNHCOOR11
RR11//
HOHO--N=CN=C\\RR22
++HH++
>N>N--CHCH22--OO--CHCH33 RR11OHOH++ >N>N--CHCH22--OO--RR11 CHCH33OHOH++HH++RR--NCONCO ++ CHCH3 3 OHOH RR--NHCOOCHNHCOOCH33
BLBL--NCO/HMMM/POLYOLNCO/HMMM/POLYOL
NCONCO NCONCO ++
HMMM
POLYOLPOLYOL
POLYOLPOLYOLHMMM
BLBL--NCO/HMMM/POLYOLNCO/HMMM/POLYOL
O COORO COOR|| /|| /
RR11--NHNH--CC--CC--HH\\COORCOOR
++ RR2 2 OHOH
O COORO COOR22|| /|| /
RR11--NHNH--CC--CC--HH\\COORCOOR22
ROHROH++
O COORO COOR|| /|| /
RR11--NHNH--CC--CC--HH\\COORCOOR
>N>N--CHCH22--OO--CHCH33
MALONATE BLOCKED NCOMALONATE BLOCKED NCO
O COORO COOR|| /|| /
RR11--NHNH--CC--CC--CHCH22--N<N<\\COORCOOR
++
CHCH33OHOH++>N>N--CHCH22--OO--CHCH33 ++ RR22OHOH
HH++
>N>N--CHCH22--OO--RR22
HMMMHMMM
ACRYLACRYL
MALONATEMALONATE
MALONATE BLOCKED NCOMALONATE BLOCKED NCO
HH++
HH++
OCHOCH33||
RR--CHCH22--SiSi--OCHOCH33||
OCHOCH33
OHOH||
RR--CHCH22--SiSi--OHOH||
OH OH
HOHHOH++ ++ CHCH3 3 OHOH
OHOH||
RR--CHCH22--SiSi--OHOH||
OH OH
OH OHOH OH| || |
RR--CHCH22--SiSi--OO--SiSi--CHCH22--RR| || |
OH OHOH OHOROR||
RR--CHCH22--SiSi--OO--CHCH22--N<N<||
OR OR
>N-CH2-O-CH3
OHOH||
RR--CHCH22--SiSi--OHOH||
OH OH
++
SILOXANESILOXANE
IMPROVED NETWORKSIMPROVED NETWORKS
MORE STABLE NETWORKMORE STABLE NETWORK
NH CROSSLINKSNH CROSSLINKSCARBAMATECARBAMATE pripri, sec, secAMIDEAMIDEUREAUREA
CH CROSSLINKSCH CROSSLINKSPHENOLPHENOLMALONATE BL. MALONATE BL.
MERCAPTOMERCAPTO
NHNH--CROSSLINKSCROSSLINKS
ALKYLALKYL--NHNH--CHCH22--(NR)(NR)22
TRIAZINETRIAZINE--NHNH--CHCH22--(NR)(NR)22
--COCO--NHNH--CHCH22--(NR)(NR)22
--COCO--NHNH--CHCH22--NHNH--CORCOR
TRIAZINETRIAZINE--NHNH--CHCH22--NHNH--TRIAZINETRIAZINE
TRIAZINETRIAZINE--NHNH--CHCH22--NHCOORNHCOOR
TRIAZINETRIAZINE--NHNH--CHCH22--NHNH--CORCOR
GLYCOLURILGLYCOLURIL--CHCH22--GLYCOLURILGLYCOLURIL
STABILITYSTABILITY pKapKa
OO||||
RR--OO--CC--NHNH22
OO||||
RR--OO--CC--NHNH--RR11
OO||||
RR--HNHN--CC--NHNH22
OO||||
RR--CC--NHNH22 CHCH33--OO--CHCH22--N<N<
HH++
NHNH--CROSSLINKSCROSSLINKS
OHOH
COORCOOR
>N>N--CHCH22--OO--CHCH33
CHCH--CROSSLINKSCROSSLINKS
COORCOOR
>N>N--CHCH22- --CHCH22--N<N<
OH
IMPROVED NETWORKSIMPROVED NETWORKS
HYDROPHOBIC BACKBONE OR HYDROLYTICALLY HYDROPHOBIC BACKBONE OR HYDROLYTICALLY STABLE BACKBONESSTABLE BACKBONES
ESTER FREE BACKBONEESTER FREE BACKBONEPOLYURETHANE WITH HYDROPHOBIC GROUPSPOLYURETHANE WITH HYDROPHOBIC GROUPSACRYLIC BACKBONEACRYLIC BACKBONE
HYDROPHOBIC & ESTER HYDROPHOBIC & ESTER FREE BACKBONEFREE BACKBONE
POLYURETHANES WITH HYDROPHOBIC GROUPSPOLYURETHANES WITH HYDROPHOBIC GROUPS
ACRYLIC POLYMERSACRYLIC POLYMERS
POLYURETHANE BACKBONES POLYURETHANE BACKBONES
POLYURETHANES WITH HYDROPHOBIC GROUPSPOLYURETHANES WITH HYDROPHOBIC GROUPS
50
60
70
80
90
0 6 12 18 24 30 36 EXPOSURE MONTH
XM-3305 COMP. B MODIF.
PU ACID ETCH/HMMMFLORIDA, 0°, GLOSS 20°,WASHED
SL2045
GLO
SS 2
0 °,
%
IMPROVED NETWORKSIMPROVED NETWORKS
OTHER POTENTIAL APPROACHESOTHER POTENTIAL APPROACHES
REDUCE SOLUBILITY OF MELAMINEREDUCE SOLUBILITY OF MELAMINEREDUCED BASICITY OF MELAMINEREDUCED BASICITY OF MELAMINECOMBINATION WITH OTHER AMINO RESINSCOMBINATION WITH OTHER AMINO RESINSCHANGE IN HYDROLYSIS EQUILIBRIUMCHANGE IN HYDROLYSIS EQUILIBRIUM
HMMM REDUCED BASICITYHMMM REDUCED BASICITY
NN
NN
NN
NN NN
OO||||CC--OO--CHCH33
CHCH22--OO--CHCH33
CHCH33--OO--CHCH22
RR--NHNH--CC||||O O
OO OONN
HN NH
ONH HN
O
HN NH
O
HN NH
O
OO
R R
>N>N--CHCH22-- OO--HH ROHROH >N>N--CHCH22--OO--RR HOHHOH++ ++HH++
REDUCED BASICITYREDUCED BASICITY
CUSTOMERCUSTOMER
CUSTOMERCUSTOMER
AcknowledgmentAcknowledgmentJ. C. Petropolous
J. N. KoralF. Hart
G. G. Parekh
L. Boldizar
P. J. Schirman
S. Cady
N. Albrecht
W. Jacobs
E. Standring
L. J. Calbo
I. UpdegraffR. Saxon
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