Hardening composition for dental impression

Abstract

The present invention relates to a hardenable composition for dental impressions comprising a hardenable base composition, a surfactant system including a first surfactant that is at least one compound having formula (I), and a fluorotelomer having formula (II), which acts synergistically with the fluorotelomer to enable the composition to have surprisingly lower contact angles, and these results are achieved with relatively low concentrations of the biodegradable surfactant. [Formula 1] JPEG2023502467000019.jpg54159CF3-(CFX) n -(CH2) m -(CHOH) p -(CYOH) (II)

Description

[Technical Field]

[0001] The present invention relates to a hardenable composition for dental impressions and its use. The present invention also relates to a method for taking an impression. [Background technology]

[0002] Room temperature vulcanizing silicone rubbers (RTV) are known as dental impression materials, especially for their mechanical and elastic properties. Furthermore, addition silicones have good dimensional stability several days after the impression is taken.

[0003] Addition-type silicone impression materials are usually prepared in a chain form by a vinyl-terminated polysiloxane and a crosslinker having Si—H groups, i.e., they are reacted typically in the presence of a platinum catalyst (hydrosilylation reaction—see, for example, U.S. Pat. No. 7,592,377 B2, "Dental Materials and Their Selection," William J. O'Brien, Quintessence Publishing Co.—ISBN-13:978-0867154375).

[0004] Another class of impression materials are condensation type silicone impression materials, which are usually prepared with hydroxy-terminated polysiloxanes and alkoxysilane crosslinkers, i.e., they usually react in the presence of a tin catalyst (see, for example, "Dental Materials and Their Selection," William J. O'Brien, Quintessence Publishing Co. - ISBN-13:978-0867154375, U.S. Pat. No. 4,389,496A, U.S. Pat. No. 5,925,723A, U.S. Pat. No. 6,218,461B1).

[0005] Typically, fillers and additives are added to both addition-type and condensation-type silicones to improve their mechanical performance or to achieve specific organoleptic properties. The use of surfactants, in particular, is known to enhance the compatibility of impression materials with oral tissue. Fluid materials designated as extra-light, light, regular, or single-phase can therefore easily penetrate the gingival sulcus with good reproduction of marginal sulcus detail. The performance of surfactants on dental impression materials is evaluated by contact angle measurements, particularly the sessile drop method.

[0006] The following formula: [ka] The use of a modified trisiloxane polyalkylene oxide superspreading surfactant having the formula: was reported in US Pat. No. 4,657,959.

[0007] Modified trisiloxane polyalkylene oxides are a powerful class of surfactants because they simultaneously possess a fairly high surface tension reduction efficacy (approximately 20 mN / m) and a very high spreading area, especially relative to other surfactants with a more pronounced surface tension reduction effect (Kovalchuk et al., "Fluoro vs Hydrocarbon surfactants: why do they differ in wetting performance?" Advances in Colloid and Interface Science, Vol. 210 (2014), pp. 65-71). Their effectiveness as superspreaders is reduced when they are encased in a matrix, which is caused by their lower ability to migrate to the impression material surface.

[0008] The modified trisiloxane polyalkylene oxide cannot reach the critical wetting concentration (CWC) when dispersed in a mixture of complex components. The CWC is the concentration at which these surfactants become super spreaders and was determined by Svitova et al. (Langmuir 1998, 14, 5023 - 5031).

[0009] To help the modified trisiloxane polyalkylene oxide function properly and reach the impression material surface easily, several compositions containing one or more additional surfactants have been proposed (see, for example, European Patent No. 1976479 B1, U.S. Patent No. 7812065, German Patent No. 112007000073, European Patent No. 2231102 B1, and U.S. Patent No. 8466210).

[0010] US Patent No. 2008 / 319100A1 describes a curable polymer selected from the group consisting of organopolysiloxanes crosslinked by addition reactions, organopolysiloxanes crosslinked by condensation reactions, polyethers containing alkoxysilyl radicals crosslinked by condensation reactions, polyethers containing aziridino radicals crosslinked by addition reactions, polyethers containing alkenyl radicals crosslinked by addition reactions, polyethers containing ester radicals of ethylenically unsaturated carboxylic acids crosslinked by radical polymerization reactions, or polyethers crosslinked by ring-opening metathesis reactions, silicones, or rubbers, and containing at least one (poly)alkylene oxide radical. and one silicon-containing nonionic surfactant having a molecular weight of less than 6000 g / mol, and a nonionic fluorosurfactant having at least one partially fluorinated or perfluorohydrocarbon radical and at least one partially fluorinated or perfluorohydrocarbon radical bonded to a (poly)alkylene oxide radical, a hydrocarbon radical, an aliphatic polyhydroxy radical, or a nitrogen-containing heterocyclic radical by an oxygen atom, an amino group, a keto group, a carboxylic acid ester group, a phosphoric acid ester group, a carboxylic acid amide group, and / or a phosphoric acid amide group.

[0011] U.S. Patent No. 2019 / 240118A1 discloses an impression material including a catalyst part and a base part, wherein the catalyst part contains a curable organopolysiloxane polymer, a catalyst and at least one filler, and the base part contains a curable organopolysiloxane polymer, an organopolysiloxane compound capable of crosslinking the curable organopolysiloxane polymer, at least one filler and a combination of surfactants, and the combination of surfactants in the base part includes a fluoroaliphatic polyoxyethylene type surfactant and a monofunctional alcohol alkoxylate type surfactant. The fluoroaliphatic polyoxyethylene type surfactant is a C6 perfluoroaliphatic chain bonded to a polyoxyethylene fragment providing a total molecular weight range of 400 to 800, and the monofunctional alcohol alkoxylate type surfactant is of each of the formulas described in claim 1 of the said document.

[0012] U.S. Patent No. 2011 / 118378A1 discloses a composition containing a curable polymer selected from the group of polyethers, silicones or rubbers, which contains an organopolysiloxane crosslinked by an addition reaction, an organopolysiloxane crosslinked by a condensation reaction, a polyether containing an alkoxysilyl group and crosslinked by a condensation reaction, a polyether containing an aziridinyl group and crosslinked by an addition reaction, a polyether containing an alkenyl group and crosslinked by an addition reaction, a polyether containing an ester group of an ethylenically unsaturated carboxylic acid and crosslinked by a radical polymerization reaction, or crosslinked by a ring-opening metathesis reaction and also containing at least one nonionic and / or ionic fluoro surfactant described in claim 1 of the said document, and also containing at least one nonionic surfactant having a silicon-containing group with a molecular weight of less than 6000 g / mol.

[0013] However, the compositions proposed so far have several drawbacks, among which are the need to relatively highly concentrate the modified trisiloxane polyalkylene oxide (especially when it is used alone), the proposed additional surfactants having harmful environmental impacts, i.e., not being biodegradable, and the resulting contact angles not always being satisfactory.

Summary of the Invention

Problems to be Solved by the Invention

[0014] The object of the present invention is to provide a curable composition for dental impressions, the use of a dental composition, and a method of taking an impression, which are designed to at least partially overcome the above drawbacks and are particularly inexpensive and easy to produce and / or implement.

Means for Solving the Problems

[0015] According to the present invention, there is provided a curable composition for dental impressions, the use of a dental composition, and a method of taking an impression as described in any one of the following independent claims and preferably any claim that depends directly or indirectly on the independent claims. Unless otherwise explicitly specified, the following terms have the meanings indicated below.

[0016] As used herein, "aliphatic" means a saturated or unsaturated, straight-chain, branched-chain, and / or cyclic non-aromatic and unsubstituted (radical) hydrocarbon (unless otherwise indicated). Non-limiting examples of aliphatic groups are t-butyl, ethenyl, 1- or 2-propenyl, cyclohexyl.

[0017] As used herein, C x -C y refers to a group having x to y carbon atoms.

[0018] As used herein, "alkyl" refers to saturated aliphatic (i.e., an aliphatic group that does not contain double or triple carbon-carbon bonds). Non-limiting examples of alkyl are methyl, n-propyl, t-butyl, and cyclohexyl.

[0019] As used herein, "perfluoro" compounds (PFCs) (or "polyfluoroalkyl" chemicals) are organofluorine compounds (radicals) that contain only carbon-fluorine and C-C bonds (no C-H bonds).

[0020] By "alkoxy" herein is meant an alkyl containing an oxygen bonded to two carbons. DETAILED DESCRIPTION OF THE INVENTION

[0021] According to a first aspect of the present invention, a curable base composition; and Formula (I): [ka] (wherein R is each independently a C1-C4 aliphatic group, and (each) R 1 are (independently of each other) C1-C6 aliphatic, and (each) R 2 are (independently) selected from the group consisting of H and C1-C3 aliphatic, and (each) R 3 is (independently of the others) selected from the group consisting of H and C1-C4 aliphatic, x is an integer from 0 to 5, y is an integer from 1 to 10, a is an integer from 1 to 30, and b is an integer from 0 to 5. a surfactant system comprising a first surfactant having (at least one compound having) A hardenable composition for dental impressions is provided, comprising:

[0022] Advantageously, but not necessarily, R is methyl. Additionally or alternatively, (each) R 1 is -C3H6-. Additionally or alternatively, (each) R 2 is -H. Additionally or alternatively, (each) R 3is selected independently from the group consisting of -H and methyl, especially (each) R 3 is methyl. Additionally or alternatively, x is an integer from 0 to 1 (especially, x is zero). Additionally or alternatively, y is an integer from 1 to 5 (especially y is 1 or 2, more especially y is 1). Additionally or alternatively, a is an integer from 5 to 20 (especially a is 6 to 8, more especially a is 7). Additionally or alternatively, b is zero.

[0023] According to some non-limiting embodiments, the surfactant system is of the following formula (II): CF3-(CFX) n -(CH2) m -(CHOH) p -(CYOH) (II) (wherein (each) X is independently selected from the group consisting of -F and -CF3, Y is selected from the group consisting of -H and -OH, n is an integer from 2 (especially up to 20, more especially up to 9), m is an integer from (especially 0) up to 5, and p is an integer from 0 (especially up to 2)) further comprises a fluorotelomer having (being at least one compound having)

[0024] Regarding fluorotelomers, they have a hydrophobic fluorine effect that helps the first surfactant adhere to the surface of the composition. Fluorotelomers with longer chains show the best performance, but they are solid and also insoluble in water ("Effect of fluorotelomer chain length on aqueous solubility and sorption by soils", Jinxia Liu and linda S.lee, Environ.Sci.Technol., 2007, Vol. 41(15), pp. 5357 - 5362).

[0025] Long-chain fluorinated alcohols tend to spontaneously form highly organized aggregates at the water surface (Complex interfacial behaviour of mixtures of fluorinated and hydrogenated alcohols, Miguel Cabrita Teixeira, thesis (July 2014) - https: / / fenix.tecnico.ulisboa.pt / downloadFile / 281870113702050 / Resumo%20alargado%20-%20Miguel%20Teixeira.pdf), but fluorinated alcohols are not fluorosurfactants as reported by E. Kissa (Fluorinated Surfactant and Repellents, Marcel Dekker, N.Y.) because the hydrophilic part of the molecule is particularly short, resulting in weak polar interactions.

[0026] For this reason, fluorotelomers are raw materials used in the production of fluorotelomer-based products (In vitro metabolism of 8-2 fluorotelomer: interspecies comparisons and metabolic pathway refinement, Toxicological sciences, Vol. 100(2), 2007, pp. 333 - 344). Telomerization is now the most commonly used process for producing highly fluorinated substances.

[0027] Normally, in the first step, perfluoroalkyl iodide (C w F 2w+1 I) reacts with tetrafluoroethylene to form a mixture of perfluoroalkyl iodides with long perfluoro chains, C w F 2w+1 (CF2CF2) kIn the second step, the product of the first step is often reacted again with tetrafluoroethylene to give C w F 2w+1 (CF2CF2) k Produces CH2CH2I.

[0028] The products of the first and second steps are intermediates for preparing more "building blocks" that react to yield a broad range of fluorotelomer and polymer-based surfactants (Ghislain et al., "Use of Iodocompounds in Radical Polymerization," Chem. Rev. 2006, 106, 3936-3952).

[0029] The reactions involved are: 5F2C=CF2+ IF5+2I2→ 5CF3CF2-I CF3CF2-I + nnC2F4→ C2F5(C2F4) nn -I C2F5(C2F4) nn -I + CH2=CH2 → C2F5(C2F4) nn -CH2=CH2-I C2F5(C2F4) nn -CH2=CH2-I + H2O → C2F5(C2F4) nn -CH2=CH2-OH + HI is.

[0030] It has been experimentally observed that the first surfactant (I) functions synergistically with the fluorotelomer (II) to enable the composition to have a surprisingly low contact angle (see Examples below). Note that these results were achieved with relatively low concentrations of surfactant. In this regard, it was hypothesized that the fluorotelomer enhances the migration ability of the first surfactant toward the impression material surface.

[0031] Furthermore, it is important to point out that both the first surfactant and the fluorotelomer (especially if they have short fluorinated chains) are biodegradable, thus making the present compositions have a significantly more favorable environmental impact than state-of-the-art compositions. Referring again to the fluorotelomer of formula (II), p is zero, especially when Y is -OH.

[0032] Advantageously, but not necessarily, n is at least 3 (particularly at least 4, more particularly at least 5, and even more particularly at least 6). According to some non-limiting embodiments, n is at most 8 (particularly at most 7).

[0033] Advantageously, but not necessarily, m is an integer from 0 to 4 (particularly 3, more particularly 2). Advantageously, but not necessarily, m is at least 1. According to a particular, non-limiting embodiment, m is 1. According to another, non-limiting embodiment, m is zero.

[0034] Advantageously, but not necessarily, p is an integer from 0 to 1. According to specific, non-limiting embodiments, p is 1. Alternatively (according to some advantageous, but non-limiting, embodiments), p is zero. According to some non-limiting embodiments, up to two (or no more than two) X are (each) -CF3.

[0035] Advantageously, but not necessarily, when at least one X is —CF 3 , the fluorotelomer has the following formula (III): (CF3)2-(CF)-(CFX) n-1 -(CH2) m -(CHOH) p -(CYOH) (III) (It is at least one compound having)

[0036] According to some non-limiting embodiments (if such), the fluorotelomer has the following formula (IIIa): (CF3)2-(CF)-(CF2) n-1 -(CH2) m -(CHOH)p -(CYOH) (IIIa) (It is at least one compound having)

[0037] Advantageously, but not necessarily, when two X are —CF 3 , the fluorotelomer has the following formula (IV): (CF3)2-(CF)-(CFX) n-3 -(CFCF3)-(CF2)-(CH2) m -(CHOH) p -(CYOH) (IV) (It is at least one compound having)

[0038] According to some non-limiting embodiments (if such), the fluorotelomer has the following formula (IVa): (CF3)2-(CF)-(CF2) n-3 -(CFCF3)-(CF2)-(CH2) m -(CHOH) p -(CYOH) (IVa) (It is at least one compound having)

[0039] According to some non-limiting specific embodiments, the fluorotelomers are (V)-(XII): [ka] (At least one compound having) a formula selected from the group consisting of: (and mixtures thereof).

[0040] Although not necessarily but advantageously, the fluorotelomer is (is at least one compound having) a formula selected from the group consisting of (V), (VII), (IX), (XI) and (XII) (and mixtures thereof). In particular, the fluorotelomer is (is at least one compound having) a formula selected from the group consisting of (IX), (XI) and (XII) (and mixtures thereof). More particularly, the fluorotelomer is (is at least one compound having) a formula selected from the group consisting of (IX) and (XI) (and mixtures thereof). In some cases, the fluorotelomer is (is at least one compound having) formula (IX).

[0041] Although not necessarily but advantageously, the curable composition contains, by weight, about 0.1% (in particular about 1%, more particularly about 2%) to in particular about 7% (more particularly about 6%, more particularly about 5%) of a first surfactant, based on the total weight of the curable composition.

[0042] Although not necessarily but advantageously, the curable composition contains, by weight, about 0.1% (more particularly about 0.5%) to in particular about 7% (more particularly about 5%, even more particularly about 3%) of a fluorotelomer, based on the total weight of the curable composition.

[0043] Although not necessarily but advantageously, the curable base composition comprises a first component (in particular consisting of at least one kind) containing a curable organopolysiloxane polymer, a second component (in particular consisting of at least one kind) containing a crosslinking agent compound capable of crosslinking the organopolysiloxane polymer, and (optionally) a third component (in particular consisting of) containing a catalyst capable of catalyzing the crosslinking reaction of the first component and the second component (in particular consisting of these). According to some non-limiting embodiments, the third component is a catalyst containing platinum or tin.

[0044] Although not necessarily but advantageously, the curable composition contains, by weight, at least about 0.005% (more particularly about 0.01%), in particular at most about 5% (more particularly about 2%) of a catalyst, based on the total weight of the curable composition.

[0045] According to embodiments of the first category (in particular, when the third component contains platinum), the curable composition contains a catalyst in an amount of at least about 0.005% by weight (more specifically, about 0.08%) and particularly at most about 1% by weight (more specifically, about 0.1%) based on the total weight of the curable composition.

[0046] According to embodiments of the first category (in particular, when the third component contains tin), the curable composition contains a catalyst in an amount of at least about 0.5% by weight (more specifically, about 0.8%) and particularly at most about 3% by weight (more specifically, about 2%) based on the total weight of the curable composition.

[0047] According to some non-limiting embodiments, the curable base composition also contains one or more fillers (such as quartz and / or fumed silica and / or precipitated silica and / or zirconium oxide and / or aluminum silicate and / or aluminum hydroxide and / or calcium silicate and / or calcium carbonate). In some cases, the curable composition contains silicon dioxide (such as quartz and / or fumed silica).

[0048] In particular, the curable composition contains silicon dioxide in an amount of about 25% (especially about 30%, more particularly about 34%) to about 55% (especially about 50%) by weight based on the total weight of the curable composition.

[0049] According to some non-limiting embodiments, the curable base composition contains a first component (especially consisting of at least one) which is an organopolysiloxane having at least two ethylenically unsaturated groups, and a second component (crosslinking agent) which has (in its chain) Si-H groups (especially at least two, particularly at least three).

[0050] This kind of organopolysiloxane preferably (but not necessarily) has the following formula: CH2=CH-(-SiR A R B O) w -SiR AR B CH=CH2 (In the formula, R A and R B are each independently a substituted or unsubstituted monovalent hydrocarbon (especially aliphatic) radical. R A and R B R may contain a double bond. A and R B Examples of groups are methyl, ethyl, phenyl, vinyl or 3,3,3-trifluoropropyl radicals. Preferably, but not necessarily, R A and R B At least one of is methyl.

[0051] The value of the integer w is such that the viscosity of the polymer at 23°C is between 50 cP and 1,000,000 cP. The preferred viscosity is between 200 and 100,000 cP. Silicone oils of different viscosities that do not contain vinyl groups may be present as plasticizers.

[0052] In particular, the third component comprises a hydrosilylation catalyst, which may be chloroplatinic acid or a platinum siloxane complex, and other such catalysts may be metals such as Rh or Pd.

[0053] The total SiH content in the curable base composition must be such as to ensure complete reaction of all vinyl present in the curable base composition, and the second component (crosslinker) may be present in slight excess. Preferably, but not necessarily, the curable base composition contains a linear or cyclic organopolysiloxane containing a high concentration of vinyl. The presence of the linear or cyclic organopolysiloxane containing a high concentration of vinyl serves to modify the reactivity of the platinum present in the catalyst.

[0054] Other materials that may be present in the curable base composition are pigments and colorants, aromatic materials.

[0055] Another possible component is a filler that can be selected from among extender fillers that impart filling, slipping, and appearance properties and reinforcing fillers having a reinforcing function.

[0056] The former, i.e., the extender filler, is a mineral filler having a BET surface area of 50 m 2 / g or less, such as quartz, calcium carbonate, attapulgite, iron oxide, aluminum silicate, and alumina, etc. The latter, i.e., the reinforcing filler, has a considerably high BET surface area and generally consists of fumed silica or precipitated silica that has been silane-treated. In some specific and non-limiting cases, the first component (organopolysiloxane) has a viscosity of about 20 cP to about 50,000 cP (particularly about 500 cP to about 20,000 cP).

[0057] In particular, the second component (crosslinking agent) contains (particularly consists of) organohydrogen siloxane and / or organohydrogen polysiloxane. According to some non-limiting embodiments, the second component contains (particularly consists of) methylhydrogen siloxane. More specifically, the second component (particularly methylhydrogen siloxane) has a viscosity of 10 (particularly about 50) to about 200 (particularly about 70) cP (even more specifically about 60 cP). According to certain and non-limiting embodiments, methylhydrogen siloxane has an SiH content of 1 to 10 mmol / g.

[0058] In particular, the third component is a catalyst containing platinum. In these cases, although not necessarily, advantageously, the curable composition contains at least about 0.005% by weight (more specifically about 0.08%), particularly at most about 1% by weight (more specifically about 0.1%) of the catalyst based on the total weight of the curable composition.

[0059] According to some non-limiting embodiments, the catalyst containing platinum includes (is) a Karstedt catalyst.

[0060] Although not necessarily, advantageously, the curable composition contains at least about 35% by weight (more specifically at least about 40%), particularly at most about 70% by weight (more specifically at most about 65%) of the first component based on the total weight of the curable composition.

[0061] According to some non-limiting embodiments, the curable composition comprises, by weight, at least about 35% (more particularly at least about 40%), especially up to about 55% (more particularly up to about 50%) of a first component (an organopolysiloxane having at least two ethylenically unsaturated groups), based on the total weight of the curable composition.

[0062] Advantageously but not necessarily, the curable composition comprises, by weight, at least about 1% (more particularly at least about 5%), especially up to about 20% (more particularly up to about 15%) of a second component, based on the total weight of the curable composition.

[0063] According to some non-limiting embodiments, the curable composition comprises, by weight, at least about 3% (more particularly at least about 5%), especially up to about 15% (more particularly up to about 10%) of a second component (an organohydrogensiloxane and / or an organohydrogenpolysiloxane), based on the total weight of the curable composition.

[0064] The proportions of the different constituents / components / additives can be varied to achieve the best results.

[0065] According to some non-limiting embodiments, the curable base composition comprises (especially consists of) a first component comprising (especially consisting of) a hydroxy-terminated organopolysiloxane and a second component (a crosslinking agent) comprising (especially consisting of) an alkoxysilane.

[0066] Examples of hydroxy-terminated organopolysiloxanes (i.e., organopolysiloxanes that can be cured by a condensation reaction) are known, for example, from German Patent No. 4137698 A1.

[0067] Typically, the hydroxy-terminated organopolysiloxane (i.e., the organopolysiloxane that can be cured by a condensation reaction) has the following formula (XVI): HO-SiR *2-B1-SiR * 2-OH (XVI) (wherein, R * is independently of each other C1-C4 aliphatic (especially alkyl, more especially methyl), and B1 is of the formula -O-(SiR’2-O) m2 -(wherein, R’ is independently of each other (especially C1-C6, more especially C1-C4) alkyl, alkenyl, alkynyl, cycloalkyl, aryl and / or aralkyl (which may be substituted), and m2 is an integer of 10-6000, preferably 20-2000) is a compound having. According to some non-limiting examples, R’ is independently of each other (especially C1-C6, more especially C1-C4) alkyl (such as methyl, ethyl, n-propyl, isopropyl or n-butyl, etc.).

[0068] Typically, alkoxysilanes are of the following formulas (XVII), (XVIII) and (XIX): (R”O) m3 -SiR” 3-m3 -B2-SiR” 3-m3 -(OR”) m3 (XVII) SiR” m4 (OR ** ) 4-m4 (XVIII)

Chemical formula

[0069] According to some non-limiting examples, R ** are each independently of one another (especially C1-C6, more particularly C1-C4) alkyl (such as methyl, ethyl, n-propyl, isopropyl or n-butyl).

[0070] According to some non-limiting examples, each R’’ is independently of one another (especially C1-C6, more particularly C1-C4) alkyl (such as methyl, ethyl, n-propyl, isopropyl or n-butyl).

[0071] According to some non-limiting examples, R 1t are each independently of one another (especially C1-C6, more particularly C1-C4) alkyl (such as methyl, ethyl, n-propyl, isopropyl or n-butyl).

[0072] In particular, the third component is a tin-containing catalyst. In these cases, although not necessarily, advantageously, the curable composition contains at least about 0.5% by weight (more specifically about 0.8%), especially up to about 3% by weight (more specifically about 2%) of the catalyst, based on the total weight of the curable composition.

[0073] According to some non-limiting embodiments, the tin-containing catalyst comprises dibutyltin dilaurate (IUPAC name: [dibutyl(dodecanoyloxy)stannyl] dodecanoate), dibutyltin diacetate (IUPAC name: [acetyloxy(dibutyl)stannyl] acetate), dioctyltin oxide (IUPAC name: dioctyl(oxo)tin - CAS number 870 - 08 - 6) and / or tin(II) octanoate (IUPAC name: lead(II) octanoate). In some specific cases, the tin-containing catalyst comprises dioctyltin oxide.

[0074] Although not necessarily, advantageously, the first component (hydroxy-terminated organopolysiloxane) has a viscosity of about 500 cP to about 80000 cP (especially 1000 cP to about 20000 cP).

[0075] Although not necessarily, advantageously, the second component (alkoxysilane) comprises methyltrimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, n-propyltrimethoxysilane, tetrakis-(butoxy-ethoxy)silane ((CH3-(CH2)3-O-(CH2)2-O)4-Si), methyltriacetoxysilane (CAS number: 4253 - 34 - 3).

[0076] According to some non-limiting embodiments, the curable composition comprises, by weight, about 1% (especially about 2%) to about 5% (especially about 4%) of the second component (alkoxysilane) based on the total weight of the curable composition.

[0077] According to a second aspect of the present invention, there is provided the use of the curable composition according to the first aspect of the present invention for taking the form of at least a part of the mouth. In particular, the use includes bringing the curable composition into contact with at least a part of the mouth.

[0078] According to a third aspect of the present invention, there is provided a method of taking an impression including bringing the curable composition according to the first aspect of the present invention into contact with at least a part of the mouth. Viscosity measurement is considered to be performed as follows. Viscosity is measured (measured) using a Brookfield viscometer DVII. This measurement is performed with a spindle at 23°C and 20 rpm. The ULA spindle is used (used) for viscosities in the range of 20 to 200 cP. The spindle SC4-21 is used (used) for viscosities in the range of 500 to 1000 cP. The spindle SC4-29 is used (used) for viscosities in the range of 2000 to 20000 cP. The spindle SC4-29 is used (used) for viscosities in the range of 50000 to 100000 cP.

[0079] Viscosity measurement is performed (performed) according to the content provided by the DIN EN ISO 3219:1993 standard (in particular based on DIN53019-1). Unless there are express instructions to the contrary, all the content of the references (papers, books, patent applications, etc.) cited in this specification are incorporated by reference herein. In particular, the cited references are incorporated herein by reference.

[0080] Further characteristics of the present invention will become apparent from the following description of non-limiting examples by way of illustration only.

Examples

[0081] Example 1 This example discloses the procedure followed for the measurement of the contact angle (static drop method). A droplet of distilled water was placed on a silicone surface (50 μm thick) cured under the following environmental conditions: a temperature of 23 ± 1°C and a relative humidity of 50 ± 10%. A video was recorded using a Kruss DSA30 and the deposition of the droplet was photographed. This measurement was performed 5 seconds and 30 seconds after the deposition.

[0082] The compositions tested in Examples 2 to 12 below had the following components.

Table 1

[0083] The polyvinyl siloxane had the following viscosities: 200 cP (15% with respect to the base + catalyst, vinyl content of 0.28 mmol / g), 1000 cP (5% with respect to the base + catalyst, vinyl content of 0.127 mmol / g), 2000 cP (20% with respect to the base + catalyst, vinyl content of 0.097 mmol / g), 20000 cP (5% with respect to the base + catalyst, vinyl content of 0.04 mmol / g).

[0084] The methyl hydrogen siloxane had a viscosity of 60 cP and an SiH content of 1.7 mmol / g. The platinum catalyst was a Karstedt catalyst (CAS number 68478-92-2). The mixing of the components was carried out using the following work instructions.

[0085] First, the base was prepared using a vertical mixing device equipped with Cowles (knife blade impellers). That is, the pigment was dispersed in the polyvinyl siloxane for 5 minutes, then quartz and fumed silica were added and mixed for 20 minutes. During this last step, the perfume was also added and mixed for 10 minutes.

[0086] The catalyst was prepared using a vertical mixing device equipped with Cowles (knife blade impellers). That is, the pigment was dispersed in the methyl hydrogen siloxane for 5 minutes, then quartz and fumed silica were added and mixed for 20 minutes. The platinum catalyst was added during the last step and mixed for 10 minutes.

[0087] Subsequently, using a dispersant together with Cowles (knife blade impellers), a surfactant was added to the above mixture and mixed for a total of 15 minutes.

[0088] 3 phr by weight (percentage of rubber / resin by weight) to 6.4 phr by weight of surfactant was added to both mixtures (3 to 6.4 phr of s and t). Phr shall be considered with respect to the weight of all other components / constituents of the composition / mixture. For example, if the surfactant has 6.4 phr by weight, the total weight of the composition will be 106.4, and the ratio of the weight of the surfactant / total weight of the composition will be 6.4 / 106.4 (corresponding to approximately 6 wt%).

[0089] Thereafter, the base and catalyst obtained after the addition of the surfactant were introduced into a 50 ml cartridge (25 mL of base and 25 mL of catalyst, 1:1), and thus mixing was carried out using a dispenser and mixing tip for each example.

[0090] The compositions tested in Examples 13 to 15 had the following components.

Table 2

[0091] The hydroxy-terminated polysiloxane had the following viscosities: 2000 cP (25% with respect to the base), 5000 cP (35.5% with respect to the base). The silicon dioxide was quartz and fumed silica. The alkoxysilane was tetrakis-(butoxy-ethoxy)silane - (CH3-(CH2)3-O-(CH2)2-O)4-Si. The tin catalyst was dioctyltin oxide. The mixing of the components was carried out using the following work instructions.

[0092] First, the base was prepared using a vertical mixing device equipped with Cowles. That is, the pigment was dispersed in the hydroxy-terminated polysiloxane for 5 minutes, then quartz and fumed silica were added and mixed for 20 minutes. During this last step, the perfume was added and mixed for 10 minutes (the last 5 minutes under vacuum).

[0093] Next, the catalyst was prepared in the following manner. That is, the hydrocarbon was dissolved in a reactor at 90 °C, mixed with the pigment over a period of 3 hours, then alkoxysilane and perfume were added and mixed for 1 hour. Thereafter, a surfactant was added to the above mixture using a dispersant together with Cowles, and mixed for a total of 15 minutes. The surfactant was added at a ratio of 1 phr to 2.5 phr by weight (1 to 2.5 phr of s and t).

[0094] Finally, the base was introduced into a 140 ml tube for each example, and the catalyst was introduced into a 60 ml tube. Mixing was carried out by hand using a spatula and injecting the base and the catalyst at a weight ratio of 10:0.32 for each example.

[0095] Example 2 (Comparative Example) The surfactant had the following formula:

Chemical formula

[0096] Example 3a The surfactant was 3 phr of Silwet L77 and 1 phr of perfluoro-9-methyldecan-1-ol (its structure was as shown below)

Chemical formula

[0097] The contact angles were 6.1° at 5 seconds and 5.4° at 30 seconds. Its performance was significantly better than the reference even at 5 seconds.

[0098] Example 3b The surfactant was 3 phr by weight of Silwet L77 and 1 phr by weight of perfluoroheptan-1-ol (the structure of which was as shown below).

Chemical formula

[0099] The contact angle was 25.7° at 5 seconds and 5° at 30 seconds. Its performance was particularly better than the reference at 30 seconds.

[0100] Example 4 The surfactant was 3 phr by weight of Silwet L77 and 1 phr by weight of tridecafluorononan-1-ol (the structure of which was as shown below).

Chemical formula

[0101] The contact angle was 6.7° at 5 seconds and 4.8° at 30 seconds. Its performance was significantly better than the reference even at 5 seconds.

[0102] Example 5 The surfactant was 3 phr by weight of Silwet L77 and 1 phr by weight of pentadecafluorotetradecan-1-ol (the structure of which was as shown below).

Chemical formula

[0103] The contact angle was 7.2° at 5 seconds and 4.6° at 30 seconds. Its performance was significantly better than the reference even at 5 seconds.

[0104] Example 6 The surfactant was 3 phr by weight of Silwet L77 and 1 phr by weight of perfluoroundecane-1,2-diol (the structure of which was as shown below). [ka]

[0105] The contact angle was 5.5° at 5 seconds and 4.4° at 30 seconds, which was significantly better than the reference even at 5 seconds.

[0106] Example 7 The surfactants were 3 phr by weight of Silwet L77 and 1 phr by weight of perfluorohexane-1,1-diol (the structure of which was shown below). [ka]

[0107] The contact angle was 28.4° at 5 seconds and 4.1° at 30 seconds, and its performance was better than the reference, especially at 30 seconds.

[0108] Example 8 The surfactants were 3 phr by weight of Silwet L77 and 1 phr by weight of perfluorodecan-1-ol (the structure of which was shown below). [ka]

[0109] The contact angle was 4.7° at 5 seconds and 3.9° at 30 seconds, and its performance was significantly better than the reference even at 5 seconds.

[0110] Example 9 The surfactants were 3 phr by weight of Silwet L77 and 1 phr by weight of perfluoro(3,7-dimethyloctan-1-ol), the structure of which was shown below. [ka]

[0111] The contact angles were 6.1° at 5 seconds and 2.7° at 30 seconds. Its performance was significantly better than the reference even at 5 seconds.

[0112] Example 10 (Comparative Example) The surfactant was 3 phr by weight of Silwet L77 and 1 phr by weight of FluorN 561 (Cytonix (trademark)) (its structure includes 4 groups hanging from a polypropylene glycol-based matrix: 2 perfluoro and 2 polyethylene glycols). The contact angles were 46° at 5 seconds and 18.4° at 30 seconds. Its performance was worse than the reference (Example 2).

[0113] Example 11 (Comparative Example) The surfactant was 3 phr by weight of Silwet L77 and 1 phr by weight of FluorN 562 (Cytonix (trademark)) (its structure includes 4 groups hanging from a polypropylene glycol-based matrix: 1 perfluoro and 3 polyethylene glycols). The contact angles were 42.1° at 5 seconds and 16.4° at 30 seconds. Its performance was worse than the reference (Example 2).

[0114] Example 12 (Comparative Example) The surfactant was 3 phr by weight of Silwet L77 and 1 phr by weight of FluorN 2900 (Cytonix) (its structure was perfluoroethylene with high molecular weight and glycol end). The contact angles were 29.5° at 5 seconds and 13.1° at 30 seconds. Its performance was not better than the reference (Example 2).

[0115] Example 13 (Comparative Example) The surfactant was 1 phr by weight of Silwet L77 (Momentive), which has the following formula:

Chemical Formula

[0116] Example 14 The surfactant was 3 phr by weight of Silwet L77 and 1 phr by weight of perfluorodecane-1-ol (the structure of which was as shown above (Example 8)). The contact angle was 26.7° at 5 seconds and 19.1° at 30 seconds. Its performance was significantly better than the reference even at 5 seconds.

[0117] Example 15 The surfactant was 3 phr by weight of Silwet L77 and 1 phr by weight of pentadecafluorooctan-1-ol (the structure of which was as shown above (Example 5)). The contact angle was 28.1° at 5 seconds and 20.3° at 30 seconds. Its performance was significantly better than the reference even at 5 seconds.

[0118] Although the principles of the present invention have been described in connection with specific embodiments, it will be apparent to those skilled in the art upon reading this specification that various modifications will be obvious. Accordingly, it is of course intended that the invention disclosed herein include such modifications within the scope of the appended claims. The scope of the present invention is limited only by the appended claims.

Claims

1. A curable base composition, At least one surfactant system comprising a first surfactant which is at least one compound having the following formula (I): 【Chemical 1】 (wherein each R is independently C １ ~C ４ is aliphatic, and each R １ is independently C １ ~C ６ is aliphatic, and each R ２ is independently H and C １ ~C ３ selected from the group consisting of aliphatics, and each R ３ is independently H and C １ ~C ４ selected from the group consisting of aliphatics, x is an integer from 0 to 5, y is an integer from 1 to 10, a is an integer from 1 to 30, and b is an integer from 0 to 5). And a fluorotelomer which is at least one compound having the following formula (II): A curable composition for dental impressions. CF ３ -(CFX) ｎ -(CH ２ ) ｍ -(CHOH) ｐ -(CYOH) (II) (wherein each X is independently selected from the group consisting of -F and -CF ３ and is selected from the group consisting of -H and -OH, n is an integer from 2 to 20, m is an integer from 0 to 5, and p is an integer from 0 to 2)

2.

3. The curable composition according to claim 1 or 2, wherein y is an integer from 1 to 2, a is an integer from 5 to 10, n is an integer from 4 to 7, and m is an integer from 0 to 2. Each R is methyl, and each R １ is -C ３ H ６ -, each R ２ is H, each R ３ is independently selected from the group consisting of H and methyl, x is an integer from 0 to 1, y is an integer from 1 to 5, a is an integer from 5 to 20, b is zero, n is an integer from 3 to 8, m is an integer from 0 to 4, and p is an integer from 0 to 1. The curable composition according to claim 1.

4.

5. The curable composition according to claim 1 or 2, which is at least one compound having a is an integer of 6 to 8, m is at least 1, and the maximum two of X are -CF ３ The curable composition according to claim 1 or 2, which is

6. where at least one X is -CF ３ the fluorotelomer has the following formula (III): (CF ３ ) ２ -(CF)-(CFX) ｎ－１ -(CH ２ ) ｍ -(CHOH) ｐ -(CYOH) (III) The curable composition according to claim 1 or 2, which is at least one compound having

7. When two X's are -CF ３ the fluorotelomer has the following formula (IV): (CF ３ ) ２ -(CF)-(CFX) ｎ－３ -(CFCF ３ )-(CF ２ )-(CH ２ ) ｍ -(CHOH) ｐ -(CYOH) (IV) The curable base composition comprises a first component containing a curable organopolysiloxane polymer, a second component containing a crosslinking agent compound capable of crosslinking the organopolysiloxane polymer, and a third component containing a catalyst capable of catalyzing the crosslinking reaction of the first component and the second component, and the third component is a catalyst containing platinum or tin. The curable composition according to any one of claims 1 to 6.

8. The curable base composition according to claim 7, comprising a first component containing an organopolysiloxane having at least two ethylenically unsaturated groups and a second component containing an organohydrogensiloxane and / or an organopolysiloxane having an Si—H group in its chain, and the third component is a catalyst containing platinum.

9. The curable base composition according to claim 7, comprising a first component containing a hydroxy-terminated polysiloxane and a second component containing an alkoxysilane, and the third component is a catalyst containing tin.

10. The curable composition according to any one of claims 1 to 9, comprising the first surfactant in an amount of 0.1% to 7% by weight based on the total weight of the curable composition and the fluorotelomer in an amount of 0.1% to 7% by weight based on the total weight of the curable composition.

11. Use of the curable composition according to any one of claims 1 to 10 for taking a mold of at least a part of the mouth, the use comprising bringing the curable composition into contact with at least a part of the mouth.

12. A method of taking an impression, comprising bringing the curable composition according to any one of claims 1 to 10 into contact with at least a part of the mouth. ​ ​

Images