Compositions based on functionalised radiation-curable silicones and anti-adhesive coatings obtained from said compositions
AssigneeRhodia Chimie
InventorJean-Marc Frances
Life of this patent
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Abstract
The invention concerns a radiation-curable silicone coating, comprising (a) at least a liquid polyorganosiloxane having a viscosity of about 10 to 10000 mPa's at 25° C. and bearing a crosslinkable/polymerisable function Fa on at least a M and/or T unit, and/or at least a crosslinkable/polymerisable function on at least a D unit; (b) at least a liquid linear polyorganosiloxane B having a viscosity of about 10 to 10000 mPa's at 25° C. and bearing two crosslinkable/polymerisable functions Fb on at least a M unit; (c) a cationic photoinitiator of onium borate type.
Claims12
An irradiation-curable silicone-based coating composition, characterized in that it comprises:
- (a) at least one liquid polyorganosiloxane A having a viscosity of approximately 10 to 10 000 mPa·s at 25° C. and carrying a crosslinkable and/or polymerizable functional group Fa on at least one M and/or T unit and/or at least one crosslinkable and/or polymerizable functional group Fa on at least one D unit,
- (b) at least one liquid linear polyorganosiloxane B having a viscosity of approximately 10 to 10 000 mPa·s at 25° C. and carrying at least 2 crosslinkable and/or polymerizable functional groups Fb on at least one M unit,
- (c) and an effective amount of a cationic photoinitiator composed of at least one onium borate.
The composition as claimed in the preceding claim, characterized in that the polyorganosiloxane A comprises at least one crosslinkable and/or polymerizable functional group Fa on the units D and/or T.
The composition as claimed in either one of the preceding claims, characterized in that the functional group Fa is chosen from the group consisting of the epoxy and/or alkenyl ether and/or oxetane and/or dioxolane functional groups.
The composition as claimed in any one of the preceding claims, characterized in that the polyorganosiloxane A is linear and composed of units of formula (I) and terminated by units of formula (II) or is cyclic and composed of units of formula (I), which formulae are represented below:
- 10
- in which:
- (1) the symbols R, which are alike or different, represent:
- (i) a linear or branched alkyl radical comprising 1 to 8 carbon atoms which is optionally substituted by at least one halogen, preferably fluorine, the alkyl radicals preferably being methyl, ethyl, propyl, octyl and 3,3,3-trifluoropropyl,
- (ii) an optionally substituted cycloalkyl radical comprising between 5 and 8 cyclic carbon atoms,
- (iii) an aryl radical comprising between 6 and 12 carbon atoms which can be substituted, preferably phenyl or dichlorophenyl,
- (iv) an aralkyl part having an alkyl part comprising between 5 and 14 carbon atoms and an aryl part comprising between 6 and 12 carbon atoms which is optionally substituted on the aryl part by halogens, alkyls and/or alkoxyls comprising 1 to 3 carbon atoms,
- (v) a hydroxyl group OH or an alkoxyl group comprising from 1 to 8 carbon atoms,
- (vi) a hydrogen radical,
- (2) the symbols X are alike or different and represent:
- (i) a group R,
- (ii) and/or a crosslinkable and/or polymerizable organofunctional group Fa, preferably an epoxy functional, oxetane functional, dioxolane functional and/or alkenyl ether functional group, connected to the silicon of the polyorganosiloxane via a divalent radical which comprises from 2 to 20 carbon atoms and which can comprise at least one heteroatom, preferably oxygen,
- (iii) with at least one of the symbols Fa in one of the units (I).
The composition as claimed in any one of the preceding claims, characterized in that the functional group Fb is chosen from the group consisting of the epoxy and/or alkenyl ether and/or oxetane and/or dioxolane functional groups.
The composition as claimed in any one of the preceding claims, characterized in that the polyorganosiloxane B is composed of units of formula (III) and terminated by units of formula (IV), which formulae are represented below:
- 11
- in which:
- (1′) the symbols R, which are alike or different, represent:
- (i) a linear or branched alkyl radical comprising 1 to 8 carbon atoms which is optionally substituted by at least one halogen, preferably fluorine, the alkyl radicals preferably being methyl, ethyl, propyl, octyl and 3,3,3-trifluoropropyl,
- (ii) an optionally substituted cycloalkyl radical comprising between 5 and 8 cyclic carbon atoms,
- (iii) an aryl radical comprising between 6 and 12 carbon atoms which can be substituted, preferably phenyl or dichlorophenyl,
- (iv) an aralkyl part having an alkyl part comprising between 5 and 14 carbon atoms and an aryl part comprising between 6 and 12 carbon atoms which is optionally substituted on the aryl part by halogens, alkyls and/or alkoxyls comprising 1 to 3 carbon atoms,
- (v) a hydroxyl group OH or an alkoxyl group comprising from 1 to 8 carbon atoms,
- (vi) and a hydrogen radical,
- (2′) the symbols Y are alike or different and represent:
- (i) a group R,
- (ii) and/or a crosslinkable and/or polymerizable organofunctional group Go, preferably an epoxy functional, oxetane functional, dioxolane functional and/or alkenyl ether functional group, connected to the silicon of the polyorganosiloxane via a divalent radical which comprises from 2 to 20 carbon atoms and which can comprise at least one heteroatom, preferably oxygen,
- (iii) with at least one of the symbols Fb and preferably two symbols Fb in one of the units (IV).
The composition as claimed in any one of the preceding claims, characterized in that the polyorganosiloxane B carries at least 2 units M with at least two functional groups Fb.
The composition as claimed in any one of the preceding claims, characterized in that the onium borate is chosen from the onium borates where the onium is derived from an element from Groups 15 to 17 of the Periodic Table or borates of an organometallic complex of an element from Groups 4 to 10 of the Periodic Table, for which:
- the cationic entity of the borate is selected from:
- (1″) onium salts of formula (I):
- [(R1)n—A—(R2)m]+ (I)
- in which formula:
- A represents an element from Groups 15 to 17, such as, for example:
- I, S, Se, P or N,
- R1 represents a C6-C20 carbocyclic or heterocyclic aryl radical, it being possible for said heterocyclic radical to comprise nitrogen or sulfur as heteroelements,
- R2 represents R1 or a linear or branched C1-C30 alkyl or alkenyl radical;
- said R1 and R2 radicals optionally being substituted by a C1-C25 alkoxy, C1-C25 alkyl, nitro, chloro, bromo, cyano, carboxyl, ester or mercapto group,
- n is an integer ranging from 1 to v+1, v being the valency of the element A,
- m is an integer ranging from 0 to v−1, with n+m=v+1,
- (2″) oxoisothiochromanium salts and in particular the 2-ethyl-4-oxoisothiochromanium or 2-dodecyl-4-oxoisothiochromanium sulfonium salt,
- and the borate anionic entity has the formula [BX′aRb]− in which:
- a and b are integers ranging, for a, from 0 to 3 and, for b, from 1 to 4, with a+b=4,
- the symbols X′ represent:
- a halogen atom (chlorine, fluorine) with a=0 to 3,
- an OH functional group with a=0 to 2,
- the symbols R3 are identical or different and represent:
- a phenyl radical substituted by at least one electron-withdrawing group, such as, for example, OCF3, CF3, NO2 or CN, and/or by at least 2 halogen atoms (very particularly fluorine), this being the case when the cationic entity is an onium of an element from Groups 15 to 17,
- a phenyl radical substituted by at least one electron-withdrawing element or group, in particular a halogen atom (very particularly fluorine), CF3, OCF3, NO2 or CN, this being the case when the cationic entity is an organometallic complex of an element from Groups 4 to 10,
- an aryl radical comprising at least two aromatic nuclei, such as, for example, biphenyl or naphthyl, which is optionally substituted by at least one electron-withdrawing element or group, in particular a halogen atom (very particularly fluorine), OCF3, CF3, NO2 or CN, whatever the cationic entity.
A release coating capable of being obtained by crosslinking and/or polymerization from the composition as claimed in any one of the preceding claims.
Dependencies are inferred from the claim text.