The present invention relates to a reactive, hydroxylated and/or 5 carboxylated, polyester resin, having a specific composition, characterized in particular by the specific selective choice of its polyol component and more particularly in combination with a specific choice of its polyacid component, with said polyol component comprising, as polyol, a hydroxylated and/or epoxidized fatty acid triglyceride (triglyceride). In particular, said polyol is free from monoalcohols and
10 more particularly the polyacid component is free from unsaturated or saturated fatty monoacids. Said resin is a resin in a solvent medium having a high solids content of at least 50%, preferably of at least 60%, more preferentially of 65% to 90% and more preferentially still of 65% to 85% by weight and with a viscosity suitable for coatings comprising a high solids content and in particular having in addition a high
15 covering power, more particularly for coatings of metal sheets (coil coatings) or coatings for metal packaging (packaging coatings).
WO2016/203136 already describes reactive, hydroxylated and/or carboxylated, polyester resins having a zero oil content, for coatings with a high solids content and a high covering power. No specific presence of hydroxylated
20 and/or epoxidized fatty acid triglyceride polyol is described or suggested, nor its effect on the improved performance qualities obtained.
The objective of the present invention is thus to improve, through the specific structure of the binding resin used, the solids content with a content by weight of at least 50% in organic solvent medium, as mentioned above, whiie maintaining a
25 viscosity of the coating composition suitable for the final application, in particular for application to metal sheets or for metal packaging. This "suitable" viscosity should be a Brookfield viscosity of less than 1000 mPa.s at the application temperature ranging from 15 to 35°C, said Brookfield viscosity being measured according to the ISO 3219 method. With regard to the targeted resin, it should have a viscosity of
30 less than 20 000 mPa.s in solution in an organic solvent at 25°C with a resin content (solids content) of 80% by weight. With regard to the high covering power of said coating comprising said resin, it is preferably greater than 400 m2 per kg of coating for a thickness of 1 urn. In particular, an increase (improvement or gain in coverage) of at least 8% and preferably of 9% to 20% in the covering power is obtained with
35 respect to a coating comprising a polyester resin which does not have the specific
2

resin composition as defined according to the present invention. The high covering
power of said coating according to the invention makes possible in particular a
significant improvement in the protection against corrosion of said metal sheets thus
coated or of said metal packaging thus coated.
5 The present invention relates first to a hydroxylated and/or carboxylated
polyester resin of specific structure obtained from a specific composition of polyol
component a) of said resin.
The invention also relates to a soiution of said resin in an organic solvent, in
particular at a resin content with respect to the weight of said solution of at least 10 50%, preferably of at least 60%, in particular ranging from 60% to 90%, more
preferentially from 65% to 90% and more preferentially still from 65% to 85%.
The invention also covers a crosslinkable composition comprising said resin,
in particular a coating composition and more particularly a coating composition for
metal sheets or for metal packagings.
15 Also covered is the use of said resin or of a solution of said resin as binder in
a coating composition in an organic solvent medium, in particular for crosslinkable
coatings and more particularly for increasing the covering power of said coating or
for protective coatings, in particular for protecting metal from corrosion.
Another subject matter of the invention is the finished product, which is a 20 coating which results from the use of said resin or of a solution of said resin or of a
crosslinkable composition containing it, in particular having an increased (improved)
covering power with respect to other common polyester resins.
The first subject matter of the invention relates to a hydroxylated and/or
carboxylated polyester resin, which comprises, in its structure, ester units formed 25 from a polyol component a) comprising at least one polyol a1) chosen from
hydroxylated and/or epoxidized fatty acid triglycerides of general formula (I):
R-C02-(H)C-(CH2-C02-R)2 (I)
with R being the residue radical without a carboxyl group of a hydroxylated and/or
epoxidized fatty acid RC02H with R comprising from 13 to 21, preferably from 13 to 30 19, carbon atoms and at least one hydroxyl and/or epoxy group.
The resin comprises units formed from a polyol component a). In other
words, this means that the resin is obtained from a composition comprising a polyol
component a).
Said polyol component a) according to the invention can comprise both 35 polyhydroxylated and/or epoxidized, including polyepoxidized, compounds (or
3

derivatives). In particular, the epoxidized compounds are categorized in the polyol component a) in so far as they react like a polyol component with respect to a polyacid by formation of ester bonds.
According to a specific option of said polyester resin, said triglyceride is
5 chosen from the triglycerides of 9- and/or 10-hydroxystearic acid, 12-hydroxystearic
acid, 14-hydroxyeicosanoic acid, 12-hydroxy-9-octadecenoic acid and/or its
epoxidized form, lesquerolic acid (14-hydroxy-cis-11-eicosenoic acid) and/or its
epoxidized form, or epoxidized soybean oil.
According to a particularly preferred option, said hydroxylated fatty acid is 10 12-hydroxystearic acid or 12-hydroxy-9-octadecenoic acid, which means that said triglyceride is hydrogenated castor oil or nonhydrogenated castor oil, preferably hydrogenated castor oil.
More particularly, the content by weight of said polyol triglyceride a1) with respect to the weight of said resin varies from 1% to 30%, preferably from 2% to 15 25%, more preferentially from 2% to 15%, more preferentially still from 3% to 12%, in a more preferred way from 4% to 10%.
Within the meaning of the present invention, the expression "the content by weight of the component Y with respect to the weight of the resin varies from 1 % to 30%" means that the units formed from component Y represent from 1% to 30% by 20 weight of the totai weight of the resin. In other words, this means that the resin is obtained from a composition comprising from 1% to 30% by weight of component Y with respect to the weight of the composition.
According to one embodiment, said polyol a1) represents from 5% to 20%, in
particular from 10% to 15%, by weight of said polyol component a).
25 According to a more specific option of the polyester resin according to the
invention, said polyol component a) comprises, in addition to said polyol a1):
a2) at least one C2 to C6 diol carrying at least one methyl side substituent, in
particular (carrying) two (VC4 side substituents, preferably said diol being a C2to C4
diol.
30 More particularly, the content by weight of the diol a2) with respect to the
weight of said resin varies from 0% to 50%, preferably from 20% to 40%, more preferentially from 25% to 35%.
According to one embodiment, said polyol a2) represents from 50% to 80%, in particular from 60% to 75%, by weight of said polyol component a).
4

According to a more specific option of said resin, said polyol component a) additionally comprises:
a3) at least one linear C2 to C6 aliphatic dioi, without any alkyl side substituent, and/or one C6 to C10 cycloaliphatic dioi and/or one C32 to C36 fatty diol, in particular 5 derived from a C32 to C36 fatty acid dimer diacid.
More particularly, the content by weight of the diol a3) with respect to the weight of said resin varies from 0% to 20%, preferably from 2% to 15%, more preferentially from 5% to 10%.
According to one embodiment, said polyol a3) represents from 10% to 30%, 10 in particular from 15% to 25%, by weight of said polyol component a).
According to a specific embodiment, the polyol component a) comprises the polyol a1), the diol a2) and the dioi a3).
The polyol component a) can in particular represent from 20% to 60%, in particular from 30% to 50%, more particularly from 35% to 45%, by weight of the 15 weight of the resin.
More particularly still in said resin, said polyol component a) additionally comprises:
a4) at least one polyol of functionality > 2 and preferably of functionality 3 or 4, more preferentially 3, 20 and (in this case) said resin has a branched structure.
A branched structure means that the structure of the chain of said resin comprises side polyester segments, related to the functionality of greater than 2 of the polyol a4).
Said triglyceride polyol a1) can be a triglyceride which results from the
25 hydrogenation of the corresponding unsaturated hydroxylated oil: the triglyceride of
12-hydroxystearic acid from the hydrogenation of castor oil (ricinoleic acid
triglyceride) or the triglyceride of 14-hydroxyeicosanoic acid from the hydrogenation
of the triglyceride of 14-hydroxy-cis-11-eicosenoic acid (the triglyceride of
lesquerolic acid).
30 Mention may be made, as suitable components a2), of: methylethylene
glycol, methylpropanedioi, neopentyl glycol (2,2-dimethyl-1,3-propanediol), dimethyl butanediol or 2-butyl-2-ethyl-1,3-propane diol, and preferably neopentyl glycol or 2-butyl-2-ethyl-1,3-propane diol.
Mention may be made, as suitable linear aliphatic diol components a3), of 35 ethylene glycol, diethyiene glycol, propylene glycol, dipropylene glycol, butanediol,
5

pentanediol or hexanediol, preferably ethylene glycol and hexanediol. Mention may be made, as cycloaliphatic diol a3), of cyclohexanedtol or cyclohexanedimethanol. Mention may be made, as fatty diol a3), of fatty diols derived from C32 to C36 fatty acid dimers with it being possible for said fatty diol to be hydrogenated or 5 nonhydrogenated. For example, said C32 to C36 fatty diols can be obtained by reduction of the carboxyl groups of C32 to C36 fatty acid dimers, more particularly by catalytic hydrogenation of said fatty acid dimers with replacement of the carboxyl groups by hydroxyl groups (reduced form of the carboxyl groups).
Mention may be made, as suitable components a4), of: glycerol and 10 trimethyloi propane.
The resin according to the invention comprises, in its structure, ester units
formed from a polyol component a) and from a polyacid component b). In other
words, this means that the resin is obtained from a composition comprising a polyol
component a) and a polyacid component b).
15 The polyacid component b) can in particular comprise diacids, diacid
derivatives or anhydrides.
More particularly still, said resin according to the invention has a polyacid component b) which comprises:
b1) at least one aromatic diacid or its anhydride, preferably representing from 20% 20 to 75% by weight of said resin,
b2) optionally, at least one linear C4 to Ci0l preferably C4 to C8, aliphatic diacid or its anhydride and/or at least one C32 to C3e fatty acid dimer diacid, b3) optionally, at least one cycloaliphatic diacid or its anhydride.
The diacids b1), b-2) and b3) can be diacid derivatives. Within the meaning of
25 the present invention, a diacid derivative is a compound which can be converted into
a diacid by hydrolysis or transesterification. The diacid derivatives include the
partially or completely esterified forms of the diacids defined above, in particular the
CrC6 alky! mono- and diesters of the diacids defined above.
The polyacid component b) can in particular represent from 40% to 80%, 30 especially from 50% to 70%, more particularly from 55% to 65%, by weight of the weight of the resin.
According to a specific composition of said resin, the polyacid component b) is constituted essentially of the diacid b1) or its anhydride.
6

According to a specific composition of said resin, the polyacid component b) of said resin comprises (in addition to the diacids b1) and b2)) at least one cycloaliphatic dicarboxylic acid b3) or its anhydride.
According to one embodiment, the content by weight of b1), with respect to 5 the weight of said resin, varies from 20% to 75%, in particular from 50% to 70%, more particularly from 55% to 65%.
Mention may be made, as aromatic diacid b1) or its anhydride, of isophthalic acid, terephthalic acid or phthalic anhydride.
Mention may be made, as linear aliphatic diacid b2) or its anhydride, of 10 malonic acid, adipic acid, succinic acid, azelaic acid or sebacic acid and, as C32 to C36 fatty acid dimer diacid, of a fatty acid dimer derived from tall oil or from rapeseed oil, which is hydrogenated or nonhydrogenated, and succinic anhydride.
Mention may be made, as cycloaliphatic diacid b3) or its anhydride, of cyclohexanedicarboxylic acid, hexahydrophthalic acid and hexahydrophthalic 15 anhydride.
A "substituted Cn diol" means that it has n carbon atoms linked together
(connected together in a chain) apart from the side substituents, which are not
counted in said number n. The term "Cn" is understood to mean the length of the
carbon chain (-C-C-) carrying the 2 hydroxyl groups, the substituents being carried
20 by these same n atoms.
The term "Cn polyacid" means that said polyacid has n carbons, including the carbons of the carboxyl (-C02H) groups.
Said diol a2) is preferably selected from: neopentyl glycol (2,2-dimethyl-1,3-
propanediol) or 2-butyl-2-ethyl-1,3-propanedio! and in particular neopentyi glycol.
25 Preferably, said polyol a2) represents less than 75% by weight of said polyol
component a).
According to a specific embodiment, the resin has a hydroxyl number of 0 to
200, of 10 to 120, of 15 to 100, of 20 to 80, of 25 to 75, of 30 to 60 or of 35 to 50 mg
KOH/g.
30 According to a specific embodiment, the resin has a carboxyl number of less
than or equal to 20, of less than or equal to 15, of less than or equal to 10, of less than or equal to 7 or of less than or equal to 5 mg KOH/g. The carboxyl number can in particular range from 0 to 20, from 0.1 to 15, from 0.5 to 10, from 1 to 7 or from 2 to 5 mg KOH/g.
7

Preferably, said resin has a hydroxyl number or a carboxyl number or an overall hydroxyl + carboxyl number ranging from 5 to 200, preferably from 10 to 175, mg KOH/g.
Said resin according to the invention has in particular a glass transition 5 temperature, measured by DSC, at 10°C/min, in two passes, of -10°C to 100°C, preferably of -10°C to 50°C and more preferentially of 0°C to 40°C.
According to a particularly preferred option of said resin, at least 50%, preferably at least 75%, by weight of said resin is biobased.
More particularly, said resin according to the invention is hydroxylated.
10 According to a more specific option, said resin has a number-average
molecular weight Mn (calculated, in particular from the OH and acid numbers and from the material balance, as explained in detail below before the experimental part) ranging from 500 to 20 000, preferably from 750 to 10 000.
According to a specific option, the two components a3) and a4) are present
15 as essential components with the other components a1) and a2) as defined above.
Said polyester resin can be prepared by a polycondensation reaction of the
polyol and polyacid components premixed and heated in the bulk molten state in a
single stage with removal of the water eliminated either under vacuum or in the
presence of a solvent forming an azeotrope with the water eliminated, such as
20 xylene. Such a process is already described in the description and examples of
WO2016/203136. Said resin can be prepared by a polycondensation reaction
between the polyol component a) and the polyacid component b) as are defined
above. The reaction can take place in a solvent medium or in the bulk molten state,
as already known to a person skilled in the art. When the reaction is carried out in
25 the presence of a solvent as azeotropic entrainer in order to remove the water, the
solvent preferentially chosen is xylene.
The reaction is advantageously carried out in the presence of a catalyst. Use may be made, as catalyst, of alkyl titanates, such as, for example, Isopropy! titanate, butyl titanate or 2-ethylhexyl titanate, or tin derivatives, such as, for example, tin 30 oxide, tin oxalate or monobutyltin oxide. The amounts of catalyst used are comprised between 100 and 5000 ppm, with respect to all of the monomers, and preferably from 500 to 1500 ppm, still with respect to all of the monomers.
A second subject matter of the invention relates to a solution of resin in an organic solvent, which solution comprises, in addition to said solvent, at least one 35 resin as defined above according to the invention.
8

In particular, as regards said solution, the content by weight of said resin with respect to the resin + solvent total weight is at least 50%, in particular at least 60%, and preferably varies from 60% to 90%, more preferentially from 65% to 90% and more preferentially still from 65% to 85%.
5 As organic solvent suitable for preparing said resin solution, said solvent can
be selected from methyl esters or ethyl esters of C2 to C4 monocarboxylic acids, or esters of said monocarboxylic acids with methoxy or ethoxy monoethers of C2 to C4 diols, in particular methoxypropyl acetate, or from dimethyl or diethyl esters of C4 to C6 dicarboxylic acids, terpenes, polyhydroxyalkanoates, methyl or ethyl esters of oils
10 of fatty acids or esters of lactic acid with C^ to C8 alcohols, aromatic solvents, such as xylene or other aromatic solvents which are distillation cuts of hydrocarbons comprising 9 carbon atoms with a boiling point (b.p.) ranging from 155 to 180°C of Solvarex® 9 type or distillation cuts of aromatic hydrocarbons comprising 10 carbon atoms with a b.p. ranging from 180 to 193°C of Solvesso® 150 ND type, optionally as
15 a mixture with glycol monoethers, such as butyl glycol (or butoxyethanol).
Preferably, said solvent is selected from aromatic solvents, as defined above, alone or as a mixture with glycol monoethers, such as, for example, the mixture of a C9 distillation cut with a b.p. ranging from 155 to 180°C, such as Solvarex® 9, with butyl glycol. Said solvent can be the solvent of preparation of said
20 resin if prepared by polycondensation in a solvent medium or a solvent of dissolution after preparation by bulk polycondensation. The solids content can be adjusted by extra addition of solvent if the resin is prepared at the start in a solvent. Said solvent can be a mixture of at least two solvents among those mentioned above.
Another subject matter of the invention relates to a coating composition,
25 preferably in an organic solvent medium, more particularly a crosslinkable composition, comprising at least one resin as defined above according to the invention or a resin solution as defined above.
More particularly, the coating composition according to the invention is crosslinkable and comprises, in addition to said resin, at least one crossiinking agent
30 carrying groups which react with the reactive groups of said resin.
Said crossiinking agent is preferably selected from melamine, benzoguanamine or a polyisocyanate, including and in particular blocked polyisocyanate, or a polyanhydride or a polysilane, in particular alkoxy-blocked polysilane, when said resin is hydroxylated, or said crossiinking agent is selected
35 from polyepoxides or polyols when said resin is carboxylated.
9

The composition according to the invention is in particular a coating
composition in an organic solvent medium. More particularly, it is a paint or varnish
composition and more particularly still a paint or varnish composition for metal
surfaces.
5 This coating composition can be applied for:
top coats (on primer) or monolayer (direct on metal),
primers,
backing coats. They are coatings for the internal part of the metal sheet not
exposed to bad weather or to light.
10 According to a particular preferred option, said composition comprises, in
addition to said resin and said crosslinking agent, at least one pigment.
Another subject matter of the invention relates to the use of a resin or of a resin solution as defined according to the invention in crosslinkable coating compositions in an organic solvent medium. More particularly, according to a first 15 option, it concerns coating compositions having a "one-component" behavior for metal, in particular for coating on metal sheet (coil coating) or for metal packaging (packaging coatings). According to a second alternative option, it concerns "two-component" coatings.
Said use according to the invention can also relate to powder coatings, in 20 particular for metal.
Preferably, in said use according to the invention, said coating is pigmented and said use is for coatings having a high covering power for a coating for protection against corrosion.
Finally, the invention relates to a coating which results from the use of at
25 least one resin or of a resin solution or of a coating composition as defined above
according to the invention. More particularly, said coating is a metal sheet coating
(coil coating) or protective coating, in particular for protecting metal against
corrosion. More particularly still, it can be a primer, top coat, monolayer or backing
coat.
30 The OH number is measured according to the ISO 2554 method and the acid
number is measured according to the ISO 2114 method.
The Mn value is calculated from the measured hydroxyl number and the measured acid number, which make it possible to calculate an equivalent mass M^ per functional group (OH or carboxyl or sum of the two if both are present) and
10

10

number-average functionality of the resin, this average functionality fm being
calculated from:
fra « Spci-f/Spd
with Xj being the number of moles of component i (acid or alcohol) and
fi being the functionality of said component i
the equivalent mass U^ is defined by Meq - 56 000/(IOH + 'add)
Thus, Mn ^10,,^ = Meq*fm
The following examples are set out below by way of illustration of the invention and of its performance qualities and do not in any way limit the scope of the invention.

Experimental part
1) Preparation of the resin for primer 1.1) Table of the starting materials used (see table 1) 15

Table 1]
Starting material Chemical name Supplier Technical function Nature of the
chemical
functionality Component according to the invention
PAN Phthalic anhydride Polynt Monomer Carboxyl/2 Diacidbl)
ISO Isophthalic acid Pen pet Monomer Carboxyl/2 Diacid b1)
EG Ethylene glycol Dow Monomer Hydroxyl/2 Diol a3
NPG Neopentyl glycol Perstorp Monomer Hydroxyl/2 Diol a2
HCO Hydrogen ate d castor oil Jayant Monomer Hydroxyl/3 Polyol triglyceride a1
Solvarex^ 9 Aromatic solvent Total Solvent of the resin Solvent of the resin
Fascaf 4100 Monobutyitin oxide PMC Organometaliix Catalyst Catalyst
Xylene Xylene Total Azeotropic
entraining
solvent Azeotropic solvent

1.2) Procedure for preparation of the resin: according to the invention (example 1)
and comparative test 1 without HCO (see table 2 for the proportions)
In a 1.5 I glass reactor equipped with:
20 a distillation column of the Vigreux type surmounted by a Dean and Stark
separator,
a dip pipe for introducing nitrogen,
a temperature probe,
11

the monomers are charged in amounts as described in table 2 below.
The synthesis takes place at 220°C maximum in the presence of a catalyst
(Fascat® 4100: 0.08 g) and of xylene as azeotropic entrainer (30 g) in order to
remove the water from the reaction.
5 The resin according to the invention and according to the comparative
example is diluted in Solvarex® 9 (as supplement in order to have the solids content presented in table 2).
The characteristics of the two resins are given in table 2. Compositions and characteristics of the resins (apart from solvent, catalyst 10 and azeotropic entrainer) according to the invention (example 1) and comparative
testl
[Table 2]

Comparative test 1 Test according to the invention (example 1)
Phthalic anhydride 203 184
Isophthalic acid 440 398
Ethylene glycol 150 69
Neopentyl glycol 207 299
HCO 0 50
TOTAL 1000 1000
Resin hydroxy! number (mg KOH/g) (ISO 2554 method) 42 45
Resin acid number (mg KOH/g) (ISO 2114 method) 3.1 3.5
Solids content (%) (ISO 3251 method) 64.7 64.5
Brookfield viscosity at 25°C (mPa.s) (ISO 3219 method) with the solids content indicated 11 200 4000
2) Preparation of the resin for top coat 15 2.1) Table of the starting materials used (see table 3)
Starting materials used vs resin for top coat
[Table 3]
12

Starting material Chemical name Supplier Technical function Nature of the
chemical
functionality Typical composition according to the invention
PAN Phthaiic anhydride Polynt Monomer Carboxyl/2 Diacid b1)
AA Adipic acid BASF Monomer Carboxyl/2 Diacid b2)
EG Ethylene glycol Dow Monomer Hydroxyl/2 Diol a3
NPG Neopentyl glycol Perstorp Monomer Hydroxyl/2 Diol a2
TMP Trimethylol propane Lanxess Monomer Hydroxyi/3 Diol a4
HCO Hydrogenat ed castor oil Jayant Monomer Hydroxyl/3 Polyol triglyceride a1
Solvarex®19 Aromatic solvent Total Solvent of the resin Solvent of the resin
Fascat" 4100 Monobutylti n oxide PMC Organometallix Catalyst Catalyst
Xylene Xylene Total Azeotropic
entraining
solvent Azeotropic entraining solvent
2.2) Procedure for preparation of the resin: according to the invention (example 2) and comparative test 2 without HCO
The procedure used is identical to that described in point 1.2) (the amounts 5 are given in table 4).
The resin according to the invention and according to the comparative example is diluted in pure Solvarex® 9.
The characteristics of the two resins are also given in table 4. Compositions and characteristics of the resins (apart from solvent, catalyst and 10 azeotropic entrainer) according to the invention (example 2) and comparative test 2
13

jTable 4]

Resin component/characteristics Comparative test 2 Test according to the invention (example 2)
Phthalic anhydride 450 570
Adipic acid 140 0
Ethylene glycol 70 95
Neopentyl glycol 300 280
HCO 55
Trimethyiolpropane 40 0
TOTAL 1000 1000
Resin hydroxy! number (mg KOH/g) (ISO 2554 Method) 45 35
Resin acid number (mg KOH/g) (ISO 2114 Method) 3.3 2.7
Solids content (%) (ISO 3251 method) 75.4 76
Brookfield viscosity at 25°C (mPa.s) (ISO 3219 method) at the solids content indicated 18 000 16 000
3) Application of the resins in paints for metal sheet 5 3.1) Metal sheet and conditions for application of the coating/packaging before
tests
The sheeting used for the tests is galvanized steel sheeting 0.5 millimeters thick, pretreated with a chromate solution.
The paint is applied using an applicator of bar coater type. Two types of 10 application are carried out:
primer,
top coat.
In the case of the primer, the paint is applied to a bare metal sheeting so as
to obtain a film with a dry thickness of 5 um.
15 In the case of the top coat, the paint is applied to a metal sheeting coated
with a primer with a dry thickness of 5 um and in such a way as to obtain a top coat with a dry thickness of 18 um.
The sheeting thus coated is introduced into a ventilated oven.
14

Crosslinking conditions [Table 5]

Coating type T (°C) of the oven Peak T(°C) of the metal/time to reach it (s)
Primer 385 232/45
Top coat 385 232/50
5 The primer, as primer and backing coat on the metal, is evaluated by virtue
of the performance tests mentioned in table 6, after conditioning of the test panels in a climate-controlied room at 23°C ± 2° where the humidity is controlled at 50% ± 5%.
The top coat is applied to the primer and the primer plus top coat system is 10 evaluated by virtue of the performance tests mentioned in table 6, after conditioning of the test panels in a climate-controlled room at 23°C ± 2° where the humidity is controlled at 50% ± 5%.
Tests of performance qualities of the coatings 15 [Table 6]

Tests of the performance qualities Method used
Resistance to methyl ethyl ketone (s) or to methyl isobutyl ketone (s) Visual method*
Load 1 kg (MEK) or 500 g (MIBK)/linearTaber*

Cupping test (mm) NF EN ISO 1520
Adhesion test NF EN ISO 2409
Adhesion + 8 mm indented NF EN 13523-6
Adhesion + 8 mm indented + 30 min at 90°C NF EN 13523-6
T-bend test NF EN 13523-7
Persoz hardness (s) NF EN ISO 1522
Condensation tester (QCT) with water at 40°C ISO 6270
Coverage (m2/kg/um)**
Gain in coverage (%)***
15

* This method consists in carrying out to-and-fro movements over the sheeting with a device (Taber abrasion tester) soaked in solvent and consists in recording the time from which a deterioration in the coating is observed.
** Coverage = surface area in ma of metal recoatable with 1 kg of paint having a dry 5 thickness of 1 urn.
The coverage is calculated according to the following formula from the dry paint density, the solids content and the coat thickness:
Coverage = (1 kg. Solids Content %)/(Dry Density kg/m3)/1(r9 m *** The gain in coverage is the excess percentage of coverage with respect to a standard 10 resin (% of improvement in the coverage).
3.2) Formulation and preparation of a paint for a primer (see table 7)
Formulation of the primer paint
[Table 7]

Component Amount weight Component reference Function Supplier Chemical name
Resin in solvent (invention example 1 or comparative example 1) 265 (1) Binder tested see tab 2 - Polyester
Solvarex* 9 30 (2) Solvent Total Aromatic hydrocarbon
Butyl Diglycol 30 (3) Solvent Brenntag Ether alcohol
Disperbyk^-mi 9 (4) Dispersing agent Byk Block polymer
Kronos^ 2360 83.1 (5) Pigment Kronos Titanium oxide
Shieldex*81 C 303 50.3 (6) Anticorrosio n pigment Grace Silica
Heucophos181 SRPP 50.3 (7) Anticorrosio n pigment
Aerosr R 972 6.5 (8) Rheological additive Evonik Silica
Resin in solvent
(invention example 1
and comparative
example 1) 264 (9) Binder tested see tab 2 - Polyester
Cymef 303 LF 48 (10) Crosslinking agent Allnex Melamine
PTSA (10%butanolw/w) 5.8 (11) Catalyst BASF para-
Toluenesulfoni
cacid
Epikote 828 10.1 (12) Binder Dow Epoxy resin
Solvarex^ 9 73.95 (13) Solvent Total Aromatic hydrocarbon
Butyl Diglycol 73.95 (14) Solvent Brenntag Ether alcohol
Total 1000
15
16

The components (1), (2), (3), (4), (5), (6), (7) and (8) are introduced, in this
order, into a 1 liter beaker thermostatically controlled at ambient temperature. This
mixture is stirred using a stirrer of Dispermat® type and then dispersed for 30
minutes at 3500 revolutions/minute in the presence of glass beads in order to
5 facilitate the dispersion of the pigments.
The remainder of the binder (9) and the components (10), (11) and (12) are added with stirring at 1000 revolutions/minute.
Still with stirring at 1000 revolutions/minute, the viscosity of the paint is adjusted by virtue of the addition of the components (13) and (14) in sufficient 10 amount to obtain a viscosity of between 300 mPa.s and 350 mPa.s at 25°C.
The primer paint thus obtained is filtered by sieving with removal of the glass beads.
The primer paint obtained exhibits the following characteristics (cf. table 8). Characteristics of the primer paint 15 [Table 8]

Characteristic Value
Dry density (g/cm3) 1.45
% Solids (by weight) 57 (comparative example 1) 62.8 (invention example 1)
PVC* (%) 16
Cone-plate viscosity at 25°C (mPa.s) 360 (comparative example 1)
350 (invention example 1)
* PVC: Pigment Volume Concentration
17

3.2.1) Application results and performance qualities (table 9) [Table 9]

Mechanical property Comparative
example 1 Invention example 1
Resistance to methyl isobutyl ketone (s) Load 500 g/linear Taber <10 <10
Adhesion test 0 0
Adhesion + 8 mm indented 0 0
Adhesion + 8 mm indented + 30 min at 90°C 0 0
T-bend test 1.5T 1T
Persoz hardness (s) 320 325
Condensation tester (QCT) with water at 40°C - 500 h 2S2 1S2
Coverage (mz/kg/um) 393 433
Gain in coverage (%) - = 10.1
5 3.3) Formulation and preparation of a paint for a top coat (table 10)
List of the ingredients for a binder with a solids content tested adjusted to a solids
content of 70% (with respective solvents described above, respectively for resins
according to invention example 2 and comparative example 2)
18

[Table 10]

Component Amount weight Componen t reference Function Supplier Chemical name
Resin invention example 2
or comparative example 2
(solids content 70%) 226 (1) Binder tested see tab. 4. Polyester
Solvarexw10LN 30 (2) Solvent Total Aromatic hydrocarbon
Butyl Diglycol 30 (3) Solvent Brenntag Ether alcohol
Disperbyk1* 161 7.9 (4) Dispersing agent Byk Block polymer
Kronos*12360 310 (5) Pigment Kronos Titanium oxide
Syloidw ED 40 26.8 (6) Filler Grace Silica
Aerosil" R 972 3.2 (7) Rheoiogical additive Evonik Silica
Resin (solids content 70%) 174 (8) Binder see tab. 4 Polyester
Cymer 303 LF 54.6 (9) Crosslinking agent Allnex Melamine
PTSA (10%butanolw/w) 11.1 (10) Catalyst BASF para-
Toluenesulfon
ic acid
Crayvallacw Flow 200 3 (11) Spreading agent Arkema Polyester
Butyl diglycol 61.7 (12) Solvent Brenntag Ether alcohol
Soivarex^lOLN 61.7 (13) Solvent Total Aromatic hydrocarbon
Total 1000
The components (1), (2), (3), (4), (5), (6) and (7) are introduced, in this order, 5 into a 1 liter beaker thermostatically controlled at ambient temperature. This mixture is stirred using a stirrer of Dispermat type and then dispersed for 40 minutes at 3500 revolutions/minute. The remainder of the binder (8) and the compound (9) are subsequently added. The dispersing is continued at 2500 revolutions/minute for 15 minutes. Still while stirring at 1000 revolutions/minute, the components (10) and (11) 10 are added and the viscosity of the paint is adjusted to between 500 and 550 mPa.s by virtue of the addition of solvent components (12) and (13).
The top coat is evaluated on a mechanical sheeting precoated with a primer described in 4.2).
The top coat (semi-gloss) exhibits the following characteristics (cf. table 11).
19

Characteristics of the top coat
[Table 11]

Dry density (g/cm3) PVC* (%) Solids content (%) Cone-plate viscosity at 25°C (mPa.s)
Comparative example 2 Invention example 2 Comparative example 2 invention example 2
1.75 23 63.5 71 510 500
* PVC: Pigment Volume Concentration
5
3.3.1) Application results and performance qualities (table 12)
[Table 12]

Characteristic/Test Value
Resistance to methyi ethyl ketone (s) Load 1 kg/linear Taber Comparative example 2 Invention example 2

>100 >100
Cupping test (mm) 0 0
Adhesion test 0 0
Adhesion + 8 mm indented 2 0
Adhesion + 8 mm indented + 30 min at 90°C 3 0
T-bend test 2T 2T
Persoz hardness (s) 240 243
Condensation tester (QCT) with water at 40qC - 500 h 2S2 1S2
Coverage (m2/kg/um) 362 406
Gain in coverage (%) 0 12.1

CLAIMS

1.A hydroxylated and/or carboxyiated polyester resin, characterized in that it
5 comprises, in its structure, ester units formed from a polyol component a)
comprising at least one polyol a1) chosen from fatty acid triglycerides: R-C02-(H)C-(CH2-C02-R)2 (I)
with R being the residue radical without a carboxyl group of a hydroxylated and/or epoxidized fatty acid RC02H with R comprising from 13 to 21, preferably from 13 to 10 19, carbon atoms and at least one hydroxyl and/or epoxy group.
2. The polyester resin as claimed in claim 1, characterized in that said
triglyceride is chosen from the triglycerides of 9- and/or 10-hydroxystearic acid, 12-
hydroxystearic acid, 14-hydroxyeicosanoic acid, 12-hydroxy-9-octadecenoic acid
and/or its epoxidized form, lesquerolic (14-hydroxy-cis-11-eicosenoic) acid and/or its
15 epoxidized form, or epoxidized soybean oil.
3. The polyester resin as claimed in claim 1 or 2, characterized in that said
hydroxylated fatty acid triglyceride is 12-hydroxystearic acid or 12-hydroxy-9-
octadecenoic acid, which means that said triglyceride is hydrogenated or
nonhydrogenated castor oil, preferably hydrogenated castor oil.
20 4. The polyester resin as claimed in one of claims 1 to 3, characterized in that the content by weight of said polyol triglyceride a1) with respect to the weight of said resin varies from 1% to 30%, preferably from 2% to 25%, more preferentially from 2% to 15%, more preferentially from 3% to 12%, in a more preferred way from 4% to 10%.
25 5. The polyester resin as claimed in one of claims 1 to 4, characterized in that said polyol component a) comprises, in addition to said polyol a1): a2) at least one C2 to C6 diol carrying at least one methyl side substituent, in particular two methyl side substituents, preferably said diol being a C2 to C4 diol.
6. The resin as claimed in one of claims 1 to 5, characterized in that said polyol
30 component a) additionally comprises:
a3) at least one linear C2 to C6 aliphatic diol, without any alkyl side substituent, and/or one C6to C10 cycloaliphatic diol and/or one C32 to C36 fatty diol, in particular a fatty diol derived from a C32 to C36 fatty acid dimer.
7. The resin as claimed in one of claims 1 to 6, characterized in that said polyol
35 component a) additionally comprises:
21

a4) at least one polyol of functionality > 2 and preferably of functionality 3 or 4, more
preferentially 3,
and that said resin has a branched structure.
8. The resin as claimed in one of claims 1 to 6, characterized in that it has a
5 polyacid component b) which comprises:
b1) at least one aromatic diacid or its anhydride, preferably representing from 20% to 75% by weight of said resin,
b2) optionally, at least one linear C4 to C10, preferably C4 to C8, aliphatic diacid and/or one C32 to C36 fatty acid dimer diacid, 10 b3) optionally, at least one cycloaliphatic diacid.
9. The resin as claimed in one of claims 1 to 8, characterized in that said polyo!
a2) is a diol selected from: methylethylene glycol, methylpropanediol, neopentyl
glycol (2,2-dimethy!-1,3-propanediol), dimethylbutanediol or 2-butyl-2-ethyl-1,3-
propanediol and preferably neopentyl glycol or 2-butyl-2-ethyM,3-propanediol.
15 10. The resin as claimed in one of claims 1 to 9, characterized in that said polyol a2) represents less than 75% by weight of said polyol component a). 11. The resin as claimed in one of claims 1 to 10, characterized in that said resin has a hydroxyl number of 10 to 120, of 15 to 100, of 20 to 80, of 25 to 75, of 30 to 60 or of 35 to 50 mg KOH/g.
20 12. The resin as claimed in one of claims 1 to 10, characterized in that said resin has a carboxyl number of less than or equal to 20, of less than or equal to 15, of less than or equal to 10, of less than or equal to 7 or of less than or equal to 5 mg KOH/g.
13. The resin as claimed in one of claims 1 to 11, characterized in that it has a
25 glass transition temperature, measured by DSC, at 10°C/min, of -10°C to 10Q°C,
preferably of -10°C to 50°C and more preferentially of 0°C to 40°C.
14. The resin as claimed in one of claims 1 to 12, characterized in that at least
50%, preferably at least 75%, by weight of said resin is biobased.
15. The resin as claimed in one of claims 1 to 13, characterized in that it is
30 hydroxylated.
16. The resin as claimed in one of claims 1 to 14, characterized in that it has a
number-average molecular weight Mn (calculated) ranging from 500 to 20 000,
preferably from 750 to 10 000.
22

17. A solution of resin in an organic solvent, characterized in that it comprises, in
addition to said solvent, at least one resin as defined in accordance with one of
claims 1 to 15.
18. The solution as claimed in claim 16, characterized in that the content by
5 weight of said resin with respect to the resin + solvent total weight is at least 50%, in
particular at least 60%, and preferably varies from 60% to 90%, more preferentially from 65% to 90% and more preferentially still from 65% to 85%.
19. A coating composition, preferably in an organic soivent medium, preferably a
crosslinkable composition, comprising at least one resin as defined in accordance
10 with one of claims 1 to 15 or a resin solution as defined in accordance with claim 16 or 17.
20. The composition as claimed in claim 18, characterized in that it is
crosslinkable and comprises, in addition to said resin, at least one crosslinking agent
carrying groups which react with the reactive groups of said resin.
15 21. The composition as claimed in claim 18 or 19, characterized in that said crosslinking agent is selected from melamine, benzoguanamine or a polyisocyanate, including and in particular blocked polyisocyanate, or a polyanhydride or a polysilane, in particular alkoxy-blocked polysilane, when said resin is hydroxylated, or said crosslinking agent is selected from polyepoxides or polyols when said resin
20 is carboxylated.
22. The composition as claimed in one of ciaims 18 to 20, characterized in that it is a coating composition in an organic solvent medium.
23. The composition as claimed in one of claims 18 to 21, characterized in that it is a paint or varnish composition.
25 24. The composition as claimed in one of claims 18 to 22, characterized in that it
is a paint or varnish composition for metal surfaces.
25. The composition as claimed in one of claims 18 to 23, characterized in that it
comprises, in addition to said resin and said crosslinking agent, at least one
pigment. 30 26. The use of a resin as defined in accordance with one of claims 1 to 15 or of a
resin solution as defined in accordance with claim 16 or 17 in crossiinkable coating
compositions in an organic solvent medium.
27. The use as claimed in claim 25, characterized in that it concerns coating
compositions having a "one-component" behavior for metal, in particular for coating
23

on metal sheet (coil coating) and internal or external coating of metal packaging (packaging coating).
28. TTie use as claimed in claim 25 or 26, characterized in that it concerns "two-component" coatings. 5 29. The use as claimed in claim 25 or 26, characterized in that it concerns powder coatings.
30. The use as claimed in ciaim 25 or 26, characterized in that said coating is pigmented and that said use is for coatings having a high covering power or for protective coatings, in particular for protecting meta! from corrosion.
10 31. A coating, characterized in that it results from the use of at least one resin as defined in accordance with one of claims 1 to 15 or of a resin solution as defined in accordance with claim 16 or 17 or of a coating composition as defined in accordance with one of claims 18 to 24. 32. The coating as claimed in claim 30, characterized in that it concerns a
15 coating of meta! sheet (coil coating) or internal or external coating of metal packaging (packaging coating).