# US 11,078,379 B2 · Method for the prevention of mist formation in a device comprising rolls during the coating of flexible media with a crosslinkable liquid silicone composition

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- Number: US 11,078,379 B2
- Document ID: US11078379B2
- Status: Granted
- Kind: B2
- Application number: 16/312,672
- Filed: 2017-06-20
- Published: 2019-08-15
- Granted: 2021-08-03
- Earliest claimed: 2016-06-21
- Assignees: Elkem Silicones France SAS
- Applicants: Elkem Silicones France SAS; Centre National De La Recherche Scientifique; Institut National Des Sciences AppliquéEs; Universite Claude Bernard Lyon 1; Université Jean Monnet
- Inventors: Guillaume Pibre; Aymeric Genest; Stéphanie Benitou; Jean-Marc Frances; Etienne Fleury; François Ganachaud; Daniel Portinha De Almeida
- Web page: https://patentgrep.com/patent/US11078379B2

## CPC

- C09D 183/08: containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
- B62B 3/02: involving parts being adjustable, collapsible, attachable, detachable or convertible
- C09D 5/00: Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced {(electrically insulating plastics, resins or waxes H01B3/30)}; Filling pastes
- C09D 7/65: macromolecular (C09D7/41-C09D7/48 take precedence)
- C09D 183/06: containing silicon bound to oxygen-containing groups (C09D183/12 takes precedence)
- B05D 1/28: performed by transfer from the surfaces of elements carrying the liquid or other fluent material, e.g. brushes, pads, rollers
- B62B 5/0033: {Electric motors}
- B62B 2202/404: Golf articles, e.g. golfbags
- C08G 77/20: containing silicon bound to unsaturated aliphatic groups
- C08G 77/26: nitrogen-containing groups
- C08G 77/388: containing nitrogen
- C08G 77/70: {Siloxanes defined by use of the MDTQ nomenclature}
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- B62B: HAND-PROPELLED VEHICLES, e.g. HAND CARTS OR PERAMBULATORS; SLEDGES (characterised by animal propulsion B62C; propulsion of sledges by driver or engine B62M)
- B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

Approaches are described for coating various flexible media, such as sheets of paper, synthetic polymer (polyolefin, polyester, etc.) sheets or fabric sheets, with a silicone on high-speed rolls. For example, an efficient method is described for minimizing and/or reducing mist formation when coating flexible supports with a liquid silicone composition precursor of crosslinked coatings. The coating process can be performed using a coating device that includes a roll operating at a high speed.

## Claims

### Claim 1

A method of minimizing mist formation during the coating of flexible media, the method comprising the following steps I) and II):
I) preparing a liquid silicone composition X that is a precursor of silicone coating(s), the liquid silicone composition X comprising:
at least one organopolysiloxane A crosslinkable by polyaddition, by dehydrocondensation, by polycondensation, cationically or radically,
optionally at least one crosslinking organosilicon compound B,
optionally at least one catalyst or photoinitiator C, the nature of which is chosen according to the type of reaction envisaged for said organopolysiloxane A,
optionally at least one adhesion-modulating system K, and
optionally at least one crosslinking inhibitor D; and
II) coating said liquid silicone composition X onto a flexible medium by means of a roll coating device,
wherein in step I) an anti-misting additive E is added to said liquid silicone composition X and wherein the anti-misting additive E is obtained by reacting, at a temperature of from 10° C. to 100° C., at least one compound F and at least one chemical compound comprising at least one primary or secondary amine function, wherein:
each compound F is an organic compound comprising at least one alkene or alkyne function of which at least one of the substituents is an acid function, and the organic compound comprises at least one acid function and at least one alkene or alkyne function of which at least one of the substituents is an electro-attractive group.

### Claim 2 (depends on 1)

The method according to claim 1,
wherein the anti-misting additive E is obtained by reacting, at a temperature of from 10° C. to 100° C., at least one compound F and at least one organopolysiloxane O, wherein:
each compound F is an organic compound comprising at least one alkene or alkyne function of which at least one of the substituents is an acid function, and the organic compound comprises at least one acid function and at least one alkene or alkyne function of which at least one of the substituents is an electro-attractive group; and
each organopolysiloxane O is an organopolysiloxane comprising siloxy units (I.1) and (I.2) of the following formulae:
Y
a
⁢
Z
b
1
⁢
SiO
4
-
(
a
+
b
)
2
;
(
I
⁢
.1
)
Z
c
2
⁢
SiO
4
-
c
2
(
I
⁢
.2
)
wherein:
a=1 or 2, b=0, 1 or 2 and a+b=1, 2 or 3;
c=1, 2 or 3;
each Y independently represents a functional group of formula (I.3):
-E1-(NH-G)h(NH2)i (I.3)
wherein:
h=0 or 1;
i=0 or 1;
h+i=1 or 2;
E1 represents a divalent aliphatic, cycloaliphatic or aromatic hydrocarbon radical containing from 1 to 30 carbon atoms;
G, when present, represents an aliphatic hydrocarbon radical containing from 1 to 10 carbon atoms, which is monovalent when i=0 or divalent when i=1; and
the symbols Z1 and Z2, which are identical or different, represent a monovalent hydrocarbon radical having from 1 to 30 carbon atoms and optionally containing one or more unsaturated bonds and/or one or more fluorine atoms, a hydroxyl group, or a radical —OR1 wherein R1 represents a linear, cyclic or branched C1-C10 hydrocarbon radical,
each organopolysiloxane O comprising, per molecule, at least one siloxy unit (I.1) carrying at least one functional group of formula (I.3).

### Claim 3 (depends on 1)

The method according to claim 1, wherein each compound F is an organic compound comprising at least one carbon-carbon double bond and at least one carboxylic acid function.

### Claim 4 (depends on 1)

The method according to claim 1, wherein each compound F is a compound of formula (II)
wherein:
R2, R3 and R4, which are identical or different, represent a hydrogen atom, a COOH group, or a C1 to C6 alkyl group; and
R5 represents a hydrogen atom, an alkyl group comprising at least one COOH group, or an aryl group comprising at least one COOH group.

### Claim 5 (depends on 1)

The method according to claim 1, wherein each compound F is selected from the group consisting of acrylic acid, methacrylic acid, itaconic acid, crotonic acid, 2-carboxyethyl acrylate, 3-carboxypropyl acrylate, maleic acid, fumaric acid, 2-(acryloyloxy)acetic acid, 2-(acryloyloxy)propanoic acid, 3-(acryloyloxy)propanoic acid, 2-(acryloyloxy)-2-phenylacetic acid, 4-(acryloyloxy)butanoic acid, 2-(acryloyloxy)-2-methylpropanoic acid, 5-(acryloyloxy)pentanoic acid, (E)-but-2-enoic acid, (Z)-prop-1-ene-1,2,3-tricarboxylic acid, cinnamic acid, sorbic acid, 2-hexenoic acid, 2-pentenoic acid, 2,4-pentadienoic acid, ethenesulfonic acid, vinylphosphonic acid, (1-phenylvinyl)phosphonic acid, 3-(vinylsulfonyl)propanoic acid, 2-(vinylsulfonyl)acetic acid, 2-(vinylsulfonyl)succinic acid, acetylenedicarboxylic acid and propiolic acid.

### Claim 6 (depends on 2)

The method according to claim 2, wherein each organopolysiloxane O is an organopolysiloxane comprising siloxy units (I.1) and (I.2) of the following formulae:
Y
a
⁢
Z
b
1
⁢
SiO
4
-
(
a
+
b
)
2
;
(
I
⁢
.1
)
Z
c
2
⁢
SiO
4
-
c
2
(
I
⁢
.2
)
wherein:
a=1 or 2, b=0, 1 or 2 and a+b=2 or 3; and
c=2 or 3.

### Claim 7 (depends on 1)

The method according to claim 1, wherein said liquid silicone composition X comprises:
at least one radically crosslinkable organopolysiloxane A1;
at least one radical photoinitiator C1; and
optionally at least one adhesion-modulating system K.

### Claim 8

A liquid silicone composition X that is a precursor of silicone coating(s), the liquid silicone composition X comprising:
at least one organopolysiloxane A crosslinkable by polyaddition, by dehydrocondensation, by polycondensation, cationically or radically,
at least one anti-misting additive E,
optionally at least one crosslinking organosilicon compound B,
optionally at least one catalyst or photoinitiator C, the nature of which is chosen according to the type of reaction envisaged for said organopolysiloxane A,
optionally at least one adhesion-modulating system K, and
optionally at least one crosslinking inhibitor D,
wherein the anti-misting additive E is obtained by reacting, at a temperature of from 10° C. to 100° C., at least one compound F and at least one chemical compound comprising at least one primary or secondary amine function, wherein:
each compound F is an organic compound comprising at least one alkene or alkyne function of which at least one of the substituents is an acid function, and the organic compound comprises at least one acid function and at least one alkene or alkyne function of which at least one of the substituents is an electro-attractive group.

### Claim 9 (depends on 8)

The liquid silicone composition X according to claim 8, wherein said silicone composition X comprises:
at least one radically crosslinkable organopolysiloxane A1,
optionally at least one radical photoinitiator C1, and
optionally at least one adhesion-modulating system K.

### Claim 10

A silicone coating exhibiting minimized misting, wherein the coating is formed with an anti-misting additive E in an amount effective to reduce mist formation when the coating is applied to a surface of a flexible medium, and wherein the coating is formed using a liquid silicone composition X that is a precursor of the silicone coating the liquid silicone composition X comprising:
at least one organopolysiloxane A crosslinkable by polyaddition, dehydrocondensation, by polycondensation, canonically or radically,
the anti-misting additive E,
optionally at least one crosslinking organosilicon compound B,
optionally at least one catalyst or photoinitiator C, the nature of which is chosen according to the type of reaction envisaged for said organopolysiloxane A,
optionally at least one adhesion-modulating system K, and
optionally at least one crosslinking inhibitor D;
wherein the anti-misting additive E is obtained by reacting, at a temperature of from 10° C. to 100° C., at least one compound F and at least one chemical compound comprising at least one primary or secondary amine function, wherein:
each compound F is an organic compound comprising at least one alkene or alkyne function of which at least one of the substituents is an acid function, and the organic compound comprises at least one acid function and at least one alkene or alkyne function of which at least one of the substituents is an electro-attractive group.

### Claim 11 (depends on 2)

The method according to claim 2, wherein E1 is aliphatic and contains 1 to 10 carbon atoms.

### Claim 12 (depends on 2)

The method according to claim 2, wherein Z1 and Z2 represent a monovalent hydrocarbon group selected from the group consisting of alkyl groups having from 1 to 8 carbon atoms, alkenyl groups having from 2 to 6 carbon atoms and aryl groups having from 6 to 12 carbon atoms optionally containing one or more fluorine atoms, a hydroxyl group, or a radical —OR1 wherein R1 represents a linear, cyclic or branched C1-C10 hydrocarbon radical.

### Claim 13 (depends on 12)

The method according to claim 12, wherein Z1 and Z2 are selected from the group consisting of methyl, ethyl, propyl, 3,3,3-trifluoropropyl, vinyl, hydroxyl, methoxyl, xylyl, tolyl and phenyl group.

### Claim 14 (depends on 4)

The method according to claim 4, wherein R2, R3 and R4 are identical or different and represent a C1 to C3 alkyl group.

### Claim 15 (depends on 14)

The method according to claim 14, wherein R2, R3 and R4 are methyl.