U.S. patent application number 13/837616 was filed with the patent office on 2013-08-15 for coating compositions containing low voc compounds.
This patent application is currently assigned to VALSPAR SOURCING, INC.. The applicant listed for this patent is VALSPAR SOURCING, INC.. Invention is credited to LARRY B. BRANDENBURGER, MARY JANE HIBBEN, BRUCE SICKLESTEEL.
Application Number | 20130210985 13/837616 |
Document ID | / |
Family ID | 46150416 |
Filed Date | 2013-08-15 |
United States Patent
Application |
20130210985 |
Kind Code |
A1 |
BRANDENBURGER; LARRY B. ; et
al. |
August 15, 2013 |
COATING COMPOSITIONS CONTAINING LOW VOC COMPOUNDS
Abstract
Coating compositions containing coalescents and a latex polymer,
wherein the coalescent has a volatile organic content of less than
about 50% and is dispersible in the coating composition.
Inventors: |
BRANDENBURGER; LARRY B.;
(LINO LAKES, MN) ; SICKLESTEEL; BRUCE;
(SCHAUMBURG, IL) ; HIBBEN; MARY JANE; (ELBURN,
IL) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
VALSPAR SOURCING, INC.; |
|
|
US |
|
|
Assignee: |
VALSPAR SOURCING, INC.
Minneapolis
MN
|
Family ID: |
46150416 |
Appl. No.: |
13/837616 |
Filed: |
March 15, 2013 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
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13366402 |
Feb 6, 2012 |
8440752 |
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13837616 |
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12862361 |
Aug 24, 2010 |
8110624 |
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13366402 |
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10855048 |
May 27, 2004 |
7812079 |
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12862361 |
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10081351 |
Feb 22, 2002 |
6762230 |
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10855048 |
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60270680 |
Feb 22, 2001 |
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Current U.S.
Class: |
524/315 |
Current CPC
Class: |
C08K 5/101 20130101;
C09D 133/06 20130101; C09D 5/024 20130101; C08K 2003/2241 20130101;
C09D 7/43 20180101; C09D 5/028 20130101 |
Class at
Publication: |
524/315 |
International
Class: |
C09D 133/06 20060101
C09D133/06 |
Claims
1-20. (canceled)
21. A low-VOC paint, comprising: a latex polymer comprising a
surfactant and polymer particles comprising a homopolymer or
copolymer including at least one of an acrylate or a methacrylate;
a pigment; and a coalescent having the formula:
R.sup.1--(C(O)--O)--R.sup.2 wherein: R.sup.1 is an aromatic group
having 3 to 24 carbon atoms:-and R.sup.2 is a hydrocarbyl moiety
having 3 to 24 carbon atoms; with the proviso that R.sup.1 and
R.sup.2 together do not include any aliphatic unsaturated
carbon-carbon bonds; wherein the coalescent has a volatile organic
content of no greater than 50 wt-%; and wherein the total VOC in
the paint is no greater than 15 grams per 100 grams polymer
solids.
22. The paint of claim 21 wherein the coalescent is nonreactive in
the paint, and is dispersible in the paint to form a uniform
mixture.
23. The paint of claim 21 wherein the paint forms a coalesced film
at a temperature of about 4.degree. C. to about 10.degree. C.
24. The paint of claim 21 wherein the coalescent has a volatile
organic content of no greater than about 30 wt-%.
25. The paint of claim 21 comprising a mixture of coalescents,
wherein the mixture has a volatile organic content of no greater
than about 50 wt-%, and wherein at least one of the coalescents is
nonreactive in the paint, has a volatile organic content of no
greater than 15 wt-%, is dispersible in the paint to form a uniform
mixture, and has the recited formula; wherein the mixture of
coalescents is selected to facilitate, and used in an amount that
facilitates, the formation of a polymer film of the latex polymer
at a temperature of less than about 25.degree. C.
26. The paint of claim 21 wherein the total VOC in the paint is no
greater than 10 grams per 100 grams polymer solids.
27. The paint of claim 26 wherein the total VOC in the paint is no
greater than 5 grams per 100 grams polymer solids.
28. The paint of claim 27 wherein the paint contains sufficient
TiO.sub.2 pigment to be substantially visually opaque when applied
at a thickness of 3 mils (0.0762 mm) and dried.
29. The paint of claim 21 wherein the coalescent is used in an
amount less than 2 wt-%, based on polymer solids, but which
facilitates the formation of a polymer film of the latex polymer at
a temperature of less than about 25.degree. C.
30. A low-VOC paint, comprising: a pigment; a latex polymer
comprising a surfactant and polymer particles emulsified or
suspended in an aqueous medium, wherein the polymer particles
comprise a homopolymer or copolymer including at least one of an
acrylate or a methacrylate; and a coalescent having the formula:
R.sup.1--(C(O)--X.sub.r--O).sub.n--R.sup.2 wherein: R.sup.1 is an
organic group having at least 3 and less than 100 carbon atoms: X
is a divalent organic group; r is 0 or 1; n is 1 to 10; and R.sup.2
is hydrogen or an organic group having at least 3 and less than 100
carbon atoms; wherein the total VOC in the paint is no greater than
15 grams per 100 grams polymer solids.
31. The paint of claim 30 wherein the coalescent has a volatile
organic content of no greater than 15 wt-%, is nonreactive in the
paint, and is dispersible in the paint to form a uniform
mixture.
32. The paint of claim 30 wherein the coalescent is selected to
facilitate, and used in an amount that facilitates, the formation
of a polymer film of the latex polymer at a temperature of less
than 25.degree. C.
33. The paint of claim 32 wherein the coalescent is selected to
facilitate, and used in an amount that facilitates, the formation
of a polymer film of the latex polymer at a temperature of
4.degree. C. to 10.degree. C.
34. The paint of claim 30 wherein the total VOC in the paint is no
greater than 10 grams per 100 grams polymer solids.
35. The paint of claim 34 wherein the total VOC in the paint is no
greater than 5 grams per 100 grams polymer solids.
36. The paint of claim 35 wherein the total VOC in the paint is no
greater than 2 grams per 100 grams polymer solids.
37. The paint of claim 30 wherein the coalescent is used in an
amount less than 2 wt-%, based on polymer solids, but which
facilitates the formation of a polymer film of the latex polymer at
a temperature of less than about 25.degree. C.
38. A low-VOC paint, comprising: a pigment; a latex polymer
comprising a surfactant and polymer particles emulsified or
suspended in an aqueous medium, wherein the polymer particles
comprise a homopolymer or copolymer including at least one of an
acrylate or a methacrylate; and a mixture of coalescents, wherein
the mixture has a volatile organic content of no greater than 15
wt-%, and wherein at least one of the coalescents is nonreactive in
the paint, is dispersible in the paint to form a uniform mixture,
and has the formula: R.sup.1--(C(O)--X.sub.r--O).sub.n--R.sup.2
wherein: R.sup.1 is an organic group having at least 3 and less
than 100 carbon atoms, wherein the organic group is an aliphatic
group, alicyclic group, heterocyclic group, or combinations
thereof: X is a divalent organic group; r is 1; n is 1; and R.sup.2
is hydrogen or an organic group having at least 3 and less than 100
carbon atoms; with the proviso that R.sup.1 and R.sup.2 together do
not include any aliphatic unsaturated carbon-carbon bonds; and
wherein the total VOC in the paint is no greater than 15 grams per
100 grams polymer solids.
39. The paint of claim 38 wherein the total VOC in the paint is no
greater than 10 grams per 100 grams polymer solids.
40. The paint of claim 38 wherein the coalescent is used in an
amount less than 2 wt-%, based on polymer solids, but which
facilitates the formation of a polymer film of the latex polymer at
a temperature of less than about 25.degree. C.
Description
RELATED APPLICATIONS
[0001] The present application is a Continuation of U.S. patent
application Ser. No. 12/862,361, filed Aug. 24, 2010, which is a
Continuation of U.S. patent application Ser. No. 10/855,048, filed
May 27, 2004 (now U.S. Pat. No. 7,812,079) which is a
Continuation-In-Part of U.S. patent application Ser. No.
10/081,351(now U.S. Pat. No. 6,762,230), which claims the benefit
of the U.S. Provisional Application No. 60/270,680, filed 22 Feb.
2001, all of which are incorporated by reference in their
entireties.
BACKGROUND
[0002] Coating compositions, such as paints, that include latex
polymer particles typically also include a coalescent (i.e.,
coalescing agent or film-forming agent) in addition to pigments and
fillers. The coalescent functions as a solvent as well as a
plasticizer for the polymer particles to soften the latex polymer
particles and assist in the formation of a continuous coating or
film after applying to a surface and allowing to dry.
[0003] Useful coalescents are generally stable in the presence of
water, compatible with other ingredients typically used in paint
formulations, particularly the latex polymers, such that the
stability of the latex-based composition is not compromised. They
are also typically sufficiently volatile to escape when the applied
coating composition is allowed to dry, but sufficiently nonvolatile
to evaporate more slowly than other ingredients (e.g., drying
retarders, antifreezes) that delay film formation. However, there
is a general desire in the industry to reduce volatile organic
emissions, thereby reducing the environmental and health
concerns.
[0004] Governments have established regulations setting forth
guidelines relating to volatile organic compounds that may be
released into the atmosphere. To reduce the level of volatile
organic compounds, new high solids coating compositions have been
developed as well as powder coating compositions that do not
include volatile compounds, have a reduced concentration of
volatile compounds, or incorporate compounds having a lower
volatility. Reducing the volatility of coalescents, solvents,
plasticizers, etc. can adversely affect the balance of properties
needed in a latex-based coating composition, however. Thus, there
is a need for coalescents, solvents, plasticizers, etc. that can be
used in coating compositions, such as paints, that do not
compromise stability, compatibility, film formation ability, or the
desirable properties of the applied coating, etc.
SUMMARY
[0005] The present invention provides a class of compounds that
have a relatively low volatile organic content. Such compounds can
be used in coating compositions, preferably paints, as coalescing
agents, solvents, plasticizers, etc. A suitable coalescent is
dispersible in the coating composition, which is preferably stable
over time. Preferably, the compound, when used as a coalescent,
facilitates the formation of polymer films of the latex polymer at
a temperature of less than about 25.degree. C. (more preferably, at
about 4.degree. C. to about 10.degree. C., and most preferably, at
about 4.degree. C. to about 5.degree. C.). Thus, there is provided
a coating composition that includes a latex polymer and a
coalescent (which can also function as a solvent or a plasticizer).
Such coating compositions can be coated onto a substrate and dried,
as with a paint, for example.
[0006] In one embodiment, a coating composition (preferably, a
paint) includes: a latex polymer; and a coalescent having the
formula: R.sup.1--(C(O)--X.sub.r--O).sub.n--R.sup.2 wherein:
R.sup.1 is an organic group (preferably, having less than 100
carbon atoms); X is a divalent organic group (preferably, having 2
to 8 carbon atoms, and more preferably, 3 to 5 carbon atoms); r is
0 to 1; n is 1 to 10 (preferably, n is 1 to 5, more preferably, n
is 1 to 3, and most preferably, n is 2 to 3); and R.sup.2 is
hydrogen or an organic group (preferably, having less than 100
carbon atoms); with the proviso that R.sup.1 includes at least
three carbon atoms when X is not --(CH.sub.2).sub.s-- wherein s is
2 to 8; with the proviso that the coalescent has less than two
aliphatic unsaturated carbon-carbon bonds when r is zero
(preferably, the coalescent does not include aliphatic unsaturated
carbon-carbon bonds when r is zero, and more preferably, the
coalescent does not include aliphatic unsaturated carbon-carbon
bonds); wherein the coalescent has a volatile organic content of
less than about 50% (preferably, less than about 30%, more
preferably, less than about 20%, and most preferably, less than
about 15%) and is dispersible in the coating composition.
Preferably, r is one.
[0007] In another embodiment, a coating composition includes: a
latex polymer; and a coalescent having the formula:
R.sup.1--(C(O)--X.sub.r--O).sub.n--R.sup.2 wherein: R.sup.1 is an
organic group; X is a divalent organic group; r is 0 to 1; n is 1
to 10; and R.sup.2 is hydrogen or an organic group; with the
proviso that R.sup.1 includes at least three carbon atoms when X is
not --(CH.sub.2).sub.s-- wherein s is 2 to 8; with the proviso that
the coalescent does not include aliphatic unsaturated carbon-carbon
bonds; with the proviso that r is one when R.sup.2 is H; wherein
the coalescent has a volatile organic content of less than about
50%, is dispersible in the coating composition, and facilitates the
formation of polymer films of the latex polymer at a temperature of
less than about 25.degree. C. (preferably, at a temperature of
about 4.degree. C. to about 10.degree. C., and more preferably, at
a temperature of about 4.degree. C. to about 5.degree. C.).
[0008] In another embodiment, a coating composition includes: a
latex polymer; and a coalescent having the formula:
R.sup.1--(C(O)--X.sub.r--O).sub.n--R.sup.2 wherein: R.sup.1 has the
formula R.sup.3--(CH.sub.2).sub.m--(O(CH.sub.2).sub.p).sub.q--
wherein R.sup.3 is an alkyl or aryl group, m is 0 to 24, p is 1 to
4, and q is 0 to 50; X has the formula --(CH.sub.2).sub.s--,
wherein s is 2 to 8; r is 0 to 1; n is 1 to 10; and R.sup.2 is
hydrogen or R.sup.1; wherein the coalescent has a volatile organic
content of less than about 50%, is dispersible in the coating
composition, and facilitates the formation of polymer films of the
latex polymer at a temperature of less than about 25.degree. C.
(preferably, at a temperature of about 4.degree. C. to about
10.degree. C., and more preferably, at a temperature of about
4.degree. C. to about 5.degree. C.).
[0009] In yet another embodiment, a coating composition includes: a
latex polymer; and a coalescent having the formula:
R.sup.1--(C(O)--X--O).sub.n--H wherein: R.sup.1 is a hydrocarbyl
moiety or an organic group containing substituents selected from
the group of nonperoxidic oxygen atoms, hydroxyl groups, and
combinations thereof; X is a divalent hydrocarbyl moiety or an
organic group containing nonperoxidic oxygen atoms and carbonyl
groups; and n is 1 to 10; wherein the coalescent has a volatile
organic content of less than about 50% (preferably, less than about
30%) and is dispersible in the coating composition.
[0010] In still another embodiment, a coating composition includes:
a latex polymer; and a coalescent having the formula:
R.sup.1--(C(O)--X--O).sub.n--H wherein: R.sup.1 is a hydrocarbyl
moiety or an organic group containing substituents selected from
the group of nonperoxidic oxygen atoms, hydroxyl groups, and
combinations thereof; X has the formula --(CH.sub.2).sub.s--,
wherein s is 2 to 8; and n is 1 to 10; wherein the coalescent has a
volatile organic content of less than about 50% (preferably, less
than about 30%) and is dispersible in the coating composition.
[0011] In another embodiment, a coating composition includes: a
latex polymer; and a coalescent having the formula:
R.sup.1--(C(O)--X--O).sub.n--H wherein: R.sup.1 is a hydrocarbyl
moiety or an organic group containing nonperoxidic oxygens; X is an
organic group containing nonperoxidic oxygens and carbonyl groups;
and n is 1 to 10; wherein the coalescent has a volatile organic
content of less than about 50% (preferably, less than about 30%)
and is dispersible in the coating composition.
[0012] The present invention also provides methods of coating that
include: providing a coating composition as described herein;
applying the coating composition to a substrate (e.g., wall); and
allowing the coating composition to dry.
Definitions
[0013] The term "dispersible" in the context of a dispersible
coalescent means that the coalescent can be mixed into the coating
composition to form a uniform mixture without the use of high shear
mixing.
[0014] The term "stable" in the context of a coating composition
containing a dispersible coalescent means that the coalescent does
not phase separate from the coating composition upon standing at
120.degree. F. (49.degree. C.) for four weeks.
[0015] The terms "volatile organic content" and "VOC" herein mean
the volatility of the compound as measured by ASTM method
D2369-90.
[0016] The term "organic group" means a hydrocarbon (i.e.,
hydrocarbyl) group with optional elements other than carbon and
hydrogen in the chain, such as oxygen, nitrogen, sulfur, and
silicon that is classified as an aliphatic group, cyclic group, or
combination of aliphatic and cyclic groups (e.g., alkaryl and
aralkyl groups). The term "aliphatic group" means a saturated or
unsaturated linear or branched hydrocarbon group. This term is used
to encompass alkyl, alkenyl, and alkynyl groups, for example. The
term "alkyl group" means a saturated linear or branched hydrocarbon
group including, for example, methyl, ethyl, isopropyl, t-butyl,
heptyl, dodecyl, octadecyl, amyl, 2-ethylhexyl, and the like. The
term "alkenyl group" means an unsaturated linear or branched
hydrocarbon group with one or more carbon-carbon double bonds, such
as a vinyl group. The term "alkynyl group" means an unsaturated
linear or branched hydrocarbon group with one or more carbon-carbon
triple bonds. The term "cyclic group" means a closed ring
hydrocarbon group that is classified as an alicyclic group,
aromatic group, or heterocyclic group. The term "alicyclic group"
means a cyclic hydrocarbon group having properties resembling those
of aliphatic groups. The term "aromatic group" or "aryl group"
means a mono- or polynuclear aromatic hydrocarbon group. The term
"heterocyclic group" means a closed ring hydrocarbon in which one
or more of the atoms in the ring is an element other than carbon
(e.g., nitrogen, oxygen, sulfur, etc.).
[0017] Substitution is anticipated on the organic groups of the
coalescents used in the coating compositions of the present
invention. As a means of simplifying the discussion and recitation
of certain terminology used throughout this application, the terms
"group" and "moiety" are used to differentiate between chemical
species that allow for substitution or that may be substituted and
those that do not allow or may not be so substituted. Thus, when
the term "group" is used to describe a chemical substituent, the
described chemical material includes the unsubstituted group and
that group with O, N, Si, or S atoms, for example, in the chain (as
in an alkoxy group) as well as carbonyl groups or other
conventional substitution. Where the term "moiety" is used to
describe a chemical compound or substituent, only an unsubstituted
chemical material is intended to be included. For example, the
phrase "alkyl group" is intended to include not only pure open
chain saturated hydrocarbon alkyl substituents, such as methyl,
ethyl, propyl, t-butyl, and the like, but also alkyl substituents
bearing further substituents known in the art, such as hydroxy,
alkoxy, alkylsulfonyl, halogen atoms, cyano, nitro, amino,
carboxyl, etc. Thus, "alkyl group" includes ether groups,
haloalkyls, nitroalkyls, carboxyalkyls, hydroxyalkyls, sulfoalkyls,
etc. On the other hand, the phrase "alkyl moiety" is limited to the
inclusion of only pure open chain saturated hydrocarbon alkyl
substituents, such as methyl, ethyl, propyl, t-butyl, and the like.
The term "hydrocarbyl moiety" refers to unsubstituted organic
moieties containing only hydrogen and carbon.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
[0018] The present invention is directed to coating compositions
that include coalescents, which can optionally also function as
plasticizers and/or solvents, and coatings prepared therefrom.
Preferably, the coating compositions are in the form of paints.
Preferably, such coating compositions include a polymer,
preferably, a latex polymer, in addition to one or more
coalescents. The coalescent is dispersible in the coating
composition which is preferably stable over time (i.e., the
coalescent does not phase separate from the coating composition
upon standing at 49.degree. C. for four weeks).
[0019] The coating compositions of the present invention are
advantageous in that they have a relatively low volatile organic
content without sacrificing the balance of properties desired for
an applied (i.e., dry) coating, such as a paint. For example, the
coating compositions of the present invention provide an applied
coating having a preferred scrub resistance, as determined by the
test set forth in the Examples Section herein below, of at least
about that of TEXANOL, which is an alcohol/ester made from
trimethylpentane diol and isobutyric acid
((H.sub.3C).sub.2--CH--C(O)--O--CH.sub.2--C(CH.sub.3).sub.2--CH.sub.2(OH)-
--CH(CH.sub.3).sub.2).
[0020] Preferably, the coating compositions include a compound
having a relatively low volatile organic content (VOC), and more
preferably, a relatively low molecular weight. Typically, the
volatile organic content, as determined by the test set forth in
the Examples Section herein below, is no greater than about 50%,
preferably, no greater than about 30%, more preferably, no greater
than about 20%, and most preferably, no greater than about 15%,
based on the original weight of the coalesent. Preferably, the
number average molecular weight of such compounds is no greater
than about 750, and more preferably, less than about 500.
[0021] Preferably, such compounds are good coalescents. That is,
they preferably and advantageously provide good film forming
properties for a latex polymer. More preferably, a particularly
desirable group of compounds are those that provide good film
forming properties at low temperatures (e.g., below room
temperature), as determined by the test set forth in the Examples
Section herein below. Preferably, such compounds facilitate the
formation of polymer films of a latex polymer at a temperature of
less than about 25.degree. C. (more preferably, at a temperature of
about 4.degree. C. to about 10.degree. C., and most preferably, at
a temperature of about 4.degree. C. to about 5.degree. C.).
[0022] Preferably, such low VOC compounds are of the formula
R.sup.1--(C(O)--X.sub.r--O).sub.n--R.sup.2 wherein: n is 1 to 10;
R.sup.1 is an organic group, preferably, having less than 100
carbon atoms, and more preferably, having 3 to 24 carbon atoms;
R.sup.2 is hydrogen or an organic group, preferably, having less
than 100 carbon atoms; and X is a divalent organic group,
preferably, having 2 to 8 carbon atoms, and more preferably, 3 to 5
carbon atoms; and r is 0 to 1. Preferably, n is 1 to 5, more
preferably, n is 1 to 3, and most preferably, n is 2 to 3.
[0023] Preferably, R.sup.1 is a hydrocarbyl moiety, although for
certain preferred embodiments R.sup.1 is an organic group that
includes substituents selected from the group of nonperoxidic
oxygen atoms, carbonyl groups, hydroxyl groups, and combinations
thereof, more preferably, substituents selected from the group of
nonperoxidic oxygen atoms, hydroxyl groups, and combinations
thereof, and most preferably, nonperoxidic oxygen atoms. For
certain embodiments, R.sup.1 has the formula
R.sup.3--(CH.sub.2).sub.m--(O(CH.sub.2).sub.p).sub.q-- wherein
R.sup.3 is an alkyl or aryl group, m is 0 to 24, p is 1 to 4
(preferably, p is 1 to 2), and q is 0 to 50. In this preferred
formulation for R.sup.1, m+pq is preferably less than about 23.
[0024] Preferably, X is a divalent hydrocarbyl moiety, although for
certain preferred embodiments, X is an organic group that includes
substituents selected from the group of nonperoxidic oxygen atoms,
carbonyl groups, and combinations thereof, and more preferably,
nonperoxidic oxygen atoms and carbonyl groups. For certain
embodiments, X has the formula --(CH.sub.2).sub.s-- wherein s is 2
to 8, and preferably, s is 3 to 5.
[0025] For certain embodiments, X includes unsaturation.
Preferably, X includes at least one carbon-carbon double bond. A
preferred example of such a compound is bis(2-ethylhexyl)maleate
(i.e., dioctyl maleate), which is available from commercial sources
such as Aldrich Chemical Co., Milwaukee, Wis.
[0026] Preferably, R.sup.2 is hydrogen, although for certain
preferred embodiments R.sup.2 is R.sup.1 as defined above. For
certain embodiments, r is one, preferably when R.sup.2 is
hydrogen.
[0027] For certain embodiments, R.sup.1 includes at least three
carbon atoms when X is not --(CH.sub.2).sub.s-- wherein s is 2 to
8; and R.sup.1 and R.sup.2 together (i.e., the coating composition)
include less than two aliphatic unsaturated carbon-carbon bonds
when r is zero, preferably, R.sup.1 and R.sup.2 together (i.e., the
coating composition) do not include any aliphatic unsaturated
carbon-carbon bonds when r is zero, and more preferably, R.sup.1
and R.sup.2 together (i.e., the coating composition) do not include
any aliphatic unsaturated carbon-carbon bonds.
[0028] For certain embodiments, R.sup.1 is an organic group having
3 to 24 carbon atoms and substituents selected from the group of
oxygen atoms, carbonyl groups, hydroxyl groups, and combinations
thereof; and R.sup.2 is hydrogen.
[0029] A preferred group of such compounds have the formula:
R.sup.1--(C(O)--X.sub.r--O).sub.n--R.sup.2 wherein: R.sup.1 is an
organic group; X is a divalent organic group; r is 0 to 1; n is 1
to 10; and R.sup.2 is hydrogen or an organic group; with the
proviso that R.sup.1 includes at least three carbon atoms when X is
not --(CH.sub.2).sub.s-- wherein s is 2 to 8; with the proviso that
the coalescent has less than two aliphatic unsaturated
carbon-carbon bonds when r is zero. Such compounds can be made from
caprolactone and an alcohol, for example.
[0030] Another preferred group of such compounds have the formula:
R.sup.1--(C(O)--X.sub.r--O).sub.n--R.sup.2 wherein: R.sup.1 is an
organic group; X is a divalent organic group; r is 0 to 1; n is 1
to 10; and R.sup.2 is hydrogen or an organic group; with the
proviso that R.sup.1 includes at least three carbon atoms when X is
not --(CH.sub.2).sub.s-- wherein s is 2 to 8; with the proviso that
the coalescent does not include aliphatic unsaturated carbon-carbon
bonds; with the proviso that r is one when R.sup.2 is hydrogen.
[0031] Another preferred group of such compounds have the formula:
R.sup.1--(C(O)--X.sub.r--O).sub.n--R.sup.2 wherein: R.sup.1 has the
formula R.sup.3--(CH.sub.2).sub.m--(O(CH.sub.2).sub.p).sub.q--
wherein R.sup.3 is an alkyl or aryl group, m is 0 to 24, p is 1 to
4, and q is 0 to 50; X has the formula --(CH.sub.2).sub.s--,
wherein s is 2 to 8; r is 0 to 1; n is 1 to 10; and R.sup.2 is
hydrogen or R.sup.1.
[0032] Another preferred group of such compounds have the formula:
R.sup.1--(C(O)--X--O).sub.n--H wherein: R.sup.1 is a hydrocarbyl
moiety or an organic group containing substituents selected from
the group of nonperoxidic oxygen atoms, hydroxyl groups, and
combinations thereof; X is a divalent hydrocarbyl moiety or an
organic group containing nonperoxidic oxygen atoms and carbonyl
groups; and n is 1 to 10. Such compounds can be made from a
glycidyl ester of neodecanoic acid (e.g. CARDURA E10) and a
carboxylic acid, for example. Another preferred group of such
compounds have the formula: R.sup.1--(C(O)--X--O).sub.n--H wherein:
R.sup.1 is a hydrocarbyl moiety or an organic group containing
substituents selected from the group of nonperoxidic oxygen atoms,
hydroxyl groups, and combinations thereof; X has the formula
--(CH.sub.2).sub.s--, wherein s is 2 to 8; and n is 1 to 10.
[0033] Another preferred group of such compounds have the formula:
R.sup.1--(C(O)--X--O).sub.n--H wherein: R.sup.1 is a hydrocarbyl
moiety or an organic group containing nonperoxidic oxygens; X is an
organic group containing nonperoxidic oxygens and carbonyl groups;
and n is 1 to 10.
[0034] These compounds can be formed using standard organic
synthesis techniques, which are well known to one of skill in the
art. Specific syntheses are set forth in the Examples Section
herein below.
[0035] The preferred polymers of the coating compositions of the
present invention include latex polymers (i.e., latices). These are
well known in the paint art and are typically particles emulsified
or suspended in an aqueous medium. They include, for example, the
polymerization products of ethylenically unsaturated monomers, such
as alkyl and alkoxy acrylates or methacrylates, vinyl esters of
saturated carboxylic acids, monoolefins, conjugated dienes,
optionally with one or more monomers, such as, for example,
styrene, methyl methacrylate, butyl acrylate, 2-ethylhexyl
acrylate, vinyl acetate, acrylonitrile, and vinyl chloride. The
latex polymers can have a wide range of glass transition
temperatures, depending on the desired properties of the resultant
coating.
[0036] The amount of polymers and the low VOC compounds (e.g.,
coalescents) present in the coating compositions of the present
invention include an amount that provides the desired result.
Preferably, one or more relatively low VOC compounds, which
preferably function as coalescents, are present in a coating
composition in an amount of at least about 1 percent by weight
(wt-%), more preferably, at least about 2 wt-%, and most
preferably, at least about 5 wt-%, based on polymer solids.
Preferably, one or more relatively low VOC compounds are present in
a coating composition in an amount of no greater than about 50
wt-%, and more preferably, no greater than about 25 wt-%, based on
polymer solids. When mixtures of such coalescents are used, the
numerical values of the variables in the formulas described herein
are averages.
[0037] Other components of the coating compositions of the present
invention include those typically used in paint formulations, such
as pigments, fillers, thickeners, biocides, mildewcides,
surfactants, dispersants, defoamers, and the like. The coating
compositions can be made using standard techniques known in the
paint industry.
EXAMPLES
[0038] The following examples are offered to aid in understanding
of the present invention and are not to be construed as limiting
the scope thereof. Unless otherwise indicated, all parts and
percentages are by weight.
VOC Testing:
[0039] Testing of coalescents were performed using ASTM method
D2369-90. Approximately 0.5 gram (g) of coalescent was weighed into
an aluminum weighing dish and placed in a forced air oven at
110.degree. C. for 1 hour. The dish was then reweighed and the mass
lost represents the percent (%) VOC of the coalescent.
Scrub Resistance:
[0040] The coating was drawn down on a black vinyl scrub test chart
(available from the Leneta Company) with a standard 3-mil (0.0762
millimeter (mm)) Bird film applicator (available from Byk Gardner).
The film was allowed to dry at room temperature for 7 days. Scrub
resistance was measured with a Gardner Abrasion Tester (available
from Byk Gardner) using 10 g of scrub media. The number of cycles
until the coating film was first removed was recorded.
Low Temperature Coalescence (LTC):
[0041] The coating was drawn down on a Penopac paper chart
(available from the Leneta Company) with a standard 3-mil Bird film
applicator. The chart was then put in the refrigerator at
40.degree. F. (4.4.degree. C.) until dry. Coating films that did
not exhibit any cracking were determined to pass. Any cracking of
the film was considered a failure.
EXAMPLE 1
Preparation of Coalescent Compounds
Run 1. Preparation of Coalescent
[0042] Epsilon-caprolactone (2-oxepanone) (174 g), 1-dodecanol (173
g), and
[0043] FASCAT 2003 (stannous octoate, available from Atofina
Chemicals) (0.2 g) were charged to a 4-neck 500-mL round bottom
flask fitted with mechanical stirring. The contents of the flask
was heated to 150.degree. C. and held until the free caprolactone
level was below 0.5% as measured by GC (approximately four hours),
then cooled to room temperature.
[0044] Runs 2-20. Preparation of Coalescents
[0045] A variety of coalescents were prepared following the
procedure of Example 1, Run 1, with the exception that the 174 g
caprolactone was varied according to the amount listed in Table 1A,
and the 173 g of 1-dodecanol used in Example 1, Run 1 was replaced
with the alcohol and amount listed in Table 1A.
TABLE-US-00001 TABLE 1A caprolactone (grams)/ alcohol Molar Ratio
Run Alcohol (grams) Caprolactone:Alcohol % VOC 1 1-dodecanol
174/173 1.64:1 7.0% 2 1-dodecanol 200/163 2:1 6.0% 3 1-dodecanol
225/147 2.5:1 4.0% 4 1-dodecanol 240/130.5 3:1 3.0% 5 1-dodecanol
265/108 4:1 2.0% 6 benzyl alcohol 228/108 2:1 9.0% 7
2,2,4-trimethyl-1, 196/140 1.7:1 15% 3-pentane diol (TMPD) 8
2-ethylhexanol, 157/200 1.5:1 10% 2 mol EO 9 2-amino-2- 228/71.2
2.5:1 3.0% methyl-1- propanol (AMP-95) 10 1-hexanol 228/81.8 2.5:1
5.0% 11 2-butoxyethanol 228/94.4 2.5:1 8.0% (butyl cellosolve) 12
1-butanol 228/74.1 2.5:1 7.0% 13 2(2- 228/129.8 2.5:1 9.0%
butoxyethoxy) ethanol (butyl carbitol) 14 1-octanol 228/104.2 2.5:1
5.0% 15 2-propxyethanol 228/83.2 2.5:1 9.0% (propyl cellosolve) 16
1-propanol 228/48 2.5:1 11.0% 17 2-butyl-2ethyl-1,3 174/98 2.5:1
3.5% propanediol 18 1,3-butanediol 228/72 2.5:1 3.0% 19
2-methoxyethanol 228/60.8 2.5:1 7.0% (methyl cellosolve) 20
2-ethoxyethanol 228/72.1 2.5:1 7.5% (cellosolve) *TEXANOL is 99.5%
VOC by this method
EXAMPLE 2
Preparation of Coalescent Compounds
[0046] Run 1. Preparation of Coalescent from Cardura E10
[0047] CARDURA E10 (glycidyl ester of neodecanoic acid, available
from Shell Chemical) (228 g) was charged to a 4-neck 500-mL round
bottom flask equipped with mechanical stirring. The flask was
heated to 140.degree. C. and 88 g isobutyric acid was fed into the
flask over 90 minutes. The contents of the flask were held at
140.degree. C. for 2 hours and cooled to room temperature.
Runs 2-3. Preparation of Coalescents
[0048] A variety of coalescents were prepared following the
procedure of Example 2, Run 1, with the exception that the 88 g of
isobutyric acid used in Example 2, Run 1 was replaced with the acid
listed in Table 2A.
TABLE-US-00002 TABLE 2A Amount Run Acid (Grams) % VOC 1 Isobutyric
acid 88 7.0% 2 Acetic acid 60 9.0% 3 Propionic acid 74 10.0%
EXAMPLE 3
Preparation of Coating Compositions
[0049] Various coating compositions were prepared by mixing the
ingredients listed in Table 3A. For each composition the coalescent
is as described in Examples 1 and 2.
TABLE-US-00003 TABLE 3A Material Description Grams Water 62.0
Ethylene glycol 35.0 AMP-95 Amine, Angus 1.0 TAMOL 731 Dispersant,
Rohm&Haas 10.0 DEHYDRAN 1620 Defoamer, Cognis 1.0 RCL-535
TiO.sub.2, Millennium 245.0 KATHON LX 1.5% Biocide, Rohm&Haas
1.7 Emulsion polymer 453 Ammonium 2.0 hydroxide Coalescent 26.3
Ethylene glycol 20.9 SURFYNOL 504 Surfactant, Air Products 1.0
ACRYSOL RM- Thickener, Rohm&Haas 4.0 2020NPR ACRYSOL RM-6
Thickener, Rohm&Haas 31.0 FOAMASTER SA-3 Defoamer, Cognis 3.5
Water 156.0
TABLE-US-00004 TABLE 3B Exam- Scrub ple 1, Molar Ratio (relative to
Run Alcohol Caprolactone:Alcohol TEXANOL) LTC 1 1-dodecanol 1.7:1
1.27 Pass 2 1-dodecanol 2:1 1.09 Pass 3 1-dodecanol 2.5:1 Pass 4
1-dodecanol 3:1 1.07 Pass 5 1-dodecanol 4:1 0.71 Pass 6 Benzyl
alcohol 2:1 Pass 7 2,2,4-Trimethyl- 1.7:1 0.81 Pass 1,3-pentane
diol (TMPD) 8 2-ethylhexanol, 1.5:1 0.96 Pass 2 mol EO 9 2-amino-2-
2.5:1 Fail methyl-1- propanol (AMP- 95) 10 1-hexanol 2.5:1 1.10
Pass 11 2-butoxyethanol 2.5:1 1.35 Pass (butyl cellosolve) 12
1-butanol 2.5:1 1.27 Pass 13 2(2- 2.5:1 Pass butoxyethoxy) ethanol
(butyl carbitol) 14 1-octanol 2.5:1 Pass 15 2-propxyethanol 2.5:1
Pass (propyl cellosolve) 16 1-propanol 2.5:1 Pass 17
2-butyl-2ethyl-1,3 2.5:1 Pass propanediol 18 1,3-butanediol 2.5:1
Fail 19 2-methoxyethanol 2.5:1 Pass (methyl cellosolve) 20
2-ethoxyethanol 2.5:1 Pass (cellosolve) TEXANOL LTC: Pass, Scrub =
1.0
TABLE-US-00005 TABLE 3C Example 2, Run Acid LTC 1 Isobutyric acid
Pass 2 Acetic acid Pass 3 Propionic acid Pass
TABLE-US-00006 TABLE 3D Example 3, Compound VOC LTC Isodecyl
benzoate 15% Pass Bis(2-ethylhexyl) 0.6% Pass adipate
Bis(2-ethylhexyl) 3% Pass maleate
[0050] Having thus described the preferred embodiments of the
present invention, those skilled in the art will readily appreciate
that the teachings found herein may be applied to yet other
embodiments within the scope of the claims hereto attached. The
complete disclosure of all patents, patent documents, and
publications are incorporated herein by reference as if
individually incorporated.
* * * * *