US 20060252856A1

(19) United States

(12) Patent Application Publication (10) Pub. No.: US 2006/0252856 A1
Anderson et al. (43) Pub. Date: Nov. 9, 2006
(54) ADDITIVES FOR EXTENDING POT LIFE OF Publication Classification
2-COMPONENT POLYURETHANE
COATINGS (51) Int. Cl.
CSK 3/34 (2006.01)
(75) Inventors: Janis Wylam Anderson, Danbury, CT (52) U.S. Cl. .............................................. 524/92: 524/431
(US); Michael Haraczy, Trafford, PA
(US) (57) ABSTRACT
Correspondence Address: The invention relates to an additive system for increasing the
Norris, McLaughlin & Marcus P.A. pot life of two-component, Solvent-borne polyurethane coat
18th Floor
875 Third Avenue ings; such polyurethane coatings in combination with the
New York, NY 10022 (US) additive; as well as a method for increasing pot life based on
using the additive in combination with Such coatings. The
additive is based on cobalt at from 0.01-0.10% and an
(73) Assignee: R. T. Vanderbilt Company, Inc., Now organic chelating agent at 0.03-0.5%, all percentages
alk, CT
expressed as mass percent of resin Solids. Preferred amounts
(21) Appl. No.: 11/393,243 of cobalt are about 0.02-0.04% and preferred amounts of
chelating agent are about 0.066-0.15%. As it is more pre
(22) Filed: Mar. 30, 2006 ferred to use the least amount of additive, a more preferred
additive composition contains about 0.02% cobalt and about
Related U.S. Application Data 0.06-0.08% chelating agent. It is also possible to express the
components in terms of a ratio, wherein a preferred com
(60) Provisional application No. 60/677,692, filed on May position is between about 1:5 to about 1:20 cobalt:chelating
4, 2005. agent, with a most preferred composition at about 1:3.8
US 2006/0252856 A1 Nov. 9, 2006

ADDITIVES FOR EXTENDING POT LIFE OF different type of coating, i.e. alkyd coatings, usually with
2-COMPONENT POLYURETHANE COATINGS cobalt or manganese as the metal catalyst. Alkyd coatings
dry by way of an oxidative process, in which oxygen from
BACKGROUND OF THE INVENTION the air cross-links the resin. In contrast, drying of polyure
thane coatings is by way of crosslinking of isocyanate with
0001) 1. Field of the Invention a polyol. Because of the starkly different drying mechanism,
0002 The invention relates to the field of 2-component there was no motivation to use 1,10 phenathroline for
(2K), Solvent-borne polyurethane coatings. Such coatings polyurethane coatings. Furthermore, it was believed that as
require a metal catalyst to accelerate the cure rate. The most 1,10 phenathroline is non-volatile, it would remain in a
frequently used catalyst metal is tin, usually in the form of polyurethane coating and adversely affect the cure rate.
dibutyltin dilaurate (DBTDL) and/or zinc. A chelating agent
Such as 2.4-pentanedione, is commonly used in conjunction SUMMARY OF THE INVENTION
with tin for polyurethane coatings for pot life extension and 0009. Therefore, it was quite surprising that when 1,10
viscosity stability. When preparing this type of polyurethane phenanthroline is used with a 2K polyurethane coating, with
coating, one must balance the properties of cure rate and pot a cobalt catalyst replacing tin, a striking improvement in pot
life, so as to give sufficient working time without unduly life was achieved. In fact, the pot life was increased from 4
extending the cure time. While tin is excellent for cure rate, hours up to 24 hours in some cases. This is Surprising not
it yields short pot life. Therefore, there is a desire to prepare only because 1,10 phenathroline has not heretofore been
an additive combination which will increase the pot life of known to be effective in coatings other than alkyds as a drier
2-component, solvent-borne polyurethane coatings, without accelerator, but more importantly, the issue of pot life
increasing the cure time beyond an acceptable level. extension is simply not an issue with respect to alkyd
0003 2. Discussion of the Prior Art coatings.
0004 2-component (2K), solvent-borne polyurethane 0010. In view of the above, it is also expected that other
coatings are well known in the prior art since at least the organic chelating agents which are effective as drier accel
1930s. The chemical reaction that results in the production erators for alkyd systems, will work as pot life extenders for
of polyurethanes is described in German Patent 728.981 2K polyurethane coatings when combined with cobalt as a
(1937), German Patent 913.474 (1941) and German Patent metal catalyst. Such agents include nitrogen-containing aro
851,851 (1948). 2K urethane coatings are based on reactions matic compounds, such as 2,2-dipyridil and 1,10-phenath
of polyols and isocyanates. The chemical reaction is as roline, and their substituted alkyl derivatives. In particular,
follows: it was found that 2.2-dipyridil (for example as Dri-RX(R) drier
R NCO-R' OH-eRHNCOOR accelerator from OMG Americas, a 30% solution of 2.2-
dipyridyl) was also effective in increasing pot life while
0005 The presence of certain metals, most often tin providing acceptable cure rate. Other organic chelating
and/or Zinc, has been found to increase the rate of reaction. agents which should work in the present invention, based on
The catalyzed reaction proceeds at a very fast rate. This is similar activity for paint drying as the exemplified com
good for the drying of the coating, but not for application of pounds, include diamine type chelating agents as forth in
the coating. The reaction can be so rapid that the coating is U.S. Pat. No. 2,961.331, which is incorporated herein by
fully reacted before it is even applied to the substrate. The reference, including 2-(2-pyridyl)-benzimidazole, 1-(2-py
Viscosity of the coating increases as the reaction proceeds to ridylazo)-2-naphthol. 2-picolylamine, 2.2'dipyridylamine,
a gel. Pot life or bench life is the term used to define how 2-pyridinemethaldoxime, 2-pyridinealdoxime, 2-(2-pry
long the coating is useful before the viscosity reaches a level idyl)-benzoxazole, 2-pyridinaldazine, bis-(2-pyridinal)-eth
at which the user can no longer apply the coating. ylenediamine.
0006. In order to increase pot life, it has been the practice 0011. As set out above, it was surprising to find that
to include 2.4-pentanedione, in combination with tin or Zinc, organic chelating agents such as 1,10 phenathroline and
or other metals such as Zirconium, manganese, Vanadium 2,2-dipyridyl when used with cobalt are effective in increas
and aluminum. Florio, J. J. and Miller, D. J., Handbook of ing pot life for 2K polyurethane coatings. However, it was
Coatings Additives, 2nd Ed. However, though pot life is additionally Surprising to find that cobalt, replacing tin in the
extended, it is still below the commercially acceptable life of standard 2K polyurethane formula including 2.4-pentanedi
6 hours or more.
one, also provides improved superior pot life. Therefore, it
0007 U.S. Pat. No. 5,447,968 teaches a polyurethane seems that cobalt in combination with an organic chelating
forming foundry binder system containing a nitrogen-con agent is the key to extending pot life for 2K polyurethane
taining aromatic compound. Such as 2.2-dipyridil and 1.10 coatings.
phenathroline, for extending bench life (also known as pot
life). The aromatic compounds are used in combination with 0012. The invention, therefore, relates to an additive
Zinc as a metal catalyst. However, it was found by the system for increasing the pot life of two-component, Sol
inventors that Zinc or tin, in combination with either of these vent-borne polyurethane coatings; Such polyurethane coat
compounds, did not increase the pot life for a 2K polyure ings in combination with the additive; as well as a method
thane floor coating. for increasing pot life based on using the additive in com
bination with such coatings. The additive is based on cobalt
0008 1,10 phenanthroline (for example as ACTIV-8(R) at 0.01-0.10% and an organic chelating agent at from about
drier accelerator available from R.T. Vanderbilt Company, 0.03-0.5%, all percentages throughout the specification
Inc., as 38% solution of 1,10 phenanthroline in n-butanol or expressed as mass percent of the resin solids. Preferred
hexylene glycol) is a known drier accelerator used for a amounts of cobalt are about 0.02-0.04%; and preferred
US 2006/0252856 A1 Nov. 9, 2006

amounts of chelating agent are about 0.05-0.16%. As it is

more preferred to use the least amount of additive, a more TABLE 2-continued
preferred additive composition contains about 0.02% cobalt Formula Sn Zn Co Chelating Agent
and about 0.06-0.08% chelating agent. It is also possible to
express the components in terms of a ratio, wherein a 2,2-dipyridil (2)
preferred composition is between about 1:1 to about 1:20 G O.O2 O.OO3 O.O6
cobalt.chelating agent, with a most preferred composition at H O.O2 O.O6
about 1:3.8 where chelating agent is 1,10 phenanthroline, I O.O2 O.O6
and 1:3.0 for 2,2-dipyridil; all on a dry basis. J O.04 O.12
K O.O2 O.O2 O.O6
2.4-pentanedione
DETAILED DISCUSSION OF THE INVENTION
L O.O2 O.OO3 O.2
0013 The following data demonstrate that cobalt plus a M
N
O.O2
O.O2
O.2
O.2
chelating agent in a 2K polyurethane coating, yields O O.04 0.4
extended pot life, slower cure rate and better film hardness P O.O2 O.O2 O.2
than control formulas based on tin and zinc.
(1) Provided as ACTIV-8 (R) containing 38%. 1,10-phenanthroline
0014. The 2K polyurethane floor coating was prepared (2) Provided as Dri-RX(R) containing 30% 2,2-dipyridil.
according to Table 1. The two components A and B were
blended and mixed at a slow speed for 10 minutes. The 0016. The results of the testing are set forth in Table 3
Brookfield 50 rpm viscosity was measured at 30 minute below. A pot life of 6 hours or below is considered to be
intervals until the viscosity was >20,000 cps. Drawdowns unacceptable. Pot life given as >7% is considered acceptable
were made at 8 mil clearance onto plain white cards at 30 for commercial purposes. The actual pot life for >7% is
minute intervals, for the length of the pot life. The coatings between 7% and 24 hours.
were cured at 75° F., 50% RH. The Sward Rocker hardness
was measured after 24, 48, 96 and 240 hours according to TABLE 3
ASTM D 2134. One hour after the two components were Pot Life Through Dry Sward Hardness
blended, drawdowns were made 8 mill clearance onto glass
panels, for Gardiner Circular Dry Time Recorder tests. Formula (hours) (hours) 24 hours 240 hours

TABLE 1. A. 4 3 4 26
B 51A, 3/3 6 27
Part A C 51A, 4/3 5 27
D 24 11 2 29
Desmophen (R) 650 A 65 PMA 30.9% (Bayer AG) E >71A, 8/3 3 27
Desmophen R221 O3.0 (Bayer AG) F 21A 3 3 27
Byk (R) P 104 OO.6 (Byk-Chemie America) G 4 3A 4 26
Lactimon (R) OO.6 (Byk-Chemie America) H 4 3 3 25
Arcosolv (R) PM Acetate O8.9 (Lyondell Chemical) I >71A, 11 1 27
Ti-Pure (R) R900 23.7 (E.I. duPont de J 6 8/3 1 24
Neumours) K 21A 3 3 25
Raven (R) Black 1255 OO.6 (Columbian Chemicals) L 4 3 3 25
Byk 354 OO.7 (Byk-Chemie America) M 5 3A 2 26
Metal catalyst per Table 2 N >71A, 10/3 1 28
Chelating Agent per Table 2 O 3 61/3 3 27
Part B P 21A 3 4 26

Desdomur (R) N 75 BAX 28.2 (Bayer AG)

0017. In conclusion, the longest pot life is consistently
achieved with cobalt plus a chelating agent. All of the tested
00.15 (amounts are approximate; totals may not equal chelating agents provided improved pot life and good cure
100% due to rounding; metal catalysts and chelating agent rate when combined with cobalt, as compared to tin and/or
are added as part of a blend, with total weight of blend Zinc, and are therefore considered as part of the invention.
counted towards total weight of coating in Table 1. In Table However, a preferred composition includes 1,10 phenan
2, percentage of metal or chelating agent alone is shown throline (ACTIV-8(R) drier accelator), as it provided superior
based on resin Solids) film hardness.

TABLE 2 What is claimed is:

1. A coating composition, comprising:
Formula Sn Zn Co Chelating Agent
1,10-phenanthroline (1)
a 2-component, Solvent-borne polyurethane composition,
cobalt, and
an organic chelating agent.
2. The composition of claim 1, wherein the chelating
agent is chosen as 1,10 phenanthroline or 2.2-dipyridil.
3. The composition of claim 2, wherein the chelating
agent comprises 1,10 phenanthroline.
US 2006/0252856 A1 Nov. 9, 2006

4. The composition of claim 1, wherein cobalt is present 12. The method of claim 11, wherein the chelating agent
at about 0.01-0.10% and the organic chelating agent is comprises 1,10 phenanthroline.
present at about 0.03-0.5%, based on mass percent of resin 13. The method of claim 10, wherein the additive com
Solids.
position is formulated to provide cobalt at about 0.01-0.10%
5. The composition of claim 4, wherein cobalt is present and the organic chelating agent at about 0.03-0.5%, as mass
at about 0.02-0.04% and the organic chelating agent is percent of resin Solids of the polyurethane composition and
present at about 0.05-0.16%. additive composition.
6. The composition of claim 5, wherein cobalt is present
at about 0.02% and the organic chelating agent is present at 14. The method of claim 13, wherein the additive com
about 0.06-0.08%. position is formulated to provide cobalt at about 0.02-0.04%
7. The composition of claim 1, wherein the ratio of cobalt and the organic chelating agent at about 0.05-0.16%.
to organic chelating agent is about 1:1 to 1:20. 15. The method of claim 14, wherein the additive com
8. The composition of claim 7, wherein the ratio is about position is formulated to provide cobalt at about 0.02% and
1:3.8 where the chelating agent is 1,10 phenanthroline and the organic chelating agent at about 0.06-0.08%.
about 1:3.0 where the chelating agent is 2,2-dipyridil. 16. The method of claim 10, wherein the ratio of cobalt to
9. The composition of claim 1, wherein cobalt is present organic chelating agent is about 1:1 to 1:20.
at about 0.02-0.04% and the organic chelating agent is 1,10
phenanthroline and is present at about 0.03-0.5%, based on 17. The method of claim 16, wherein the ratio is about
mass percent of resin Solids. 1:3.8 where the chelating agent is 1,10 phenanthroline and
10. A method of increasing the pot life in a 2-component, about 1:3.0 where the chelating agent is 2,2-dipyridil.
Solvent-borne polyurethane composition, comprising the 18. The method of claim 10, wherein the organic chelating
step of adding to said polyurethane composition an additive agent is 1,10 phenanthroline, and wherein the additive
composition comprising cobalt and an organic chelating composition is formulated to provide cobalt at about 0.02
agent. 0.04% and the organic chelating agent at about 0.05-0.16%.
11. The method of claim 10, wherein the chelating agent
is chosen as 1,10 phenanthroline or 2,2-dipyridil.