Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
  • C08K5/37—Thiols
  • C08K5/375—Thiols containing six-membered aromatic rings
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
  • C08K5/41—Compounds containing sulfur bound to oxygen
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
  • C08L81/04—Polysulfides

Definitions

• the present invention relates to the field of oligomers and sulfide polymers of phenols and more particularly that of alkylphenol polysulfides, grouped under the common denomination of phenolic polysulfides or poly (phenol sulfides), whose characteristic odor is hidden.
• Poly (phenol sulfides) are well known compounds and widely used in many fields of industry and especially as additives for various types of resins and other polymeric materials, and for example as a coupling agents, vulcanization accelerators for rubbers, flame retardants, preservatives, to name only the main uses.
• vulcanizing agents for EPDM type rubbers, as described for example in patent EP1675989 or in application WO2008074962 where they are incorporated in masterbatches, as coupling agents for elastomeric compositions.
• comprising a reinforcing filler as described, for example, in patent EP1633813, as vulcanization accelerators for butyl rubbers, as described, for example, in application US2008 / 0287623, or else as protective agents, in particular for wood, as described, for example, in EP0944460, to name a few references and uses of these poly (phenol sulfides).
• poly (phenol sulfides) are most often in the form of viscous liquids, powders, granules or formulated in polymeric matrices, for example in masterbatches of thermoplastic resins (see WO2008074962 discussed above), and some of their representatives are for example known under the generic name of Vultac ® marketed by Arkema.
• the Applicant has now discovered that it is possible to mask the odors, or to odorize, the poly (phenol sulfides) to allow their uses and uses of manufactured products from said poly (phenol sulfides). ), without being inconvenienced by the intrinsic odors of these poly (phenol sulfides), and without altering their properties, ie while preserving their properties.
• the Applicant has now discovered that it is possible to mask all or at least partly the odor of poly (phenol sulfides) by adding a very small amount of at least one masking agent d. 'odour.
• the addition of at least one odor-masking agent in at least one poly (phenol sulphide) makes it possible to obtain a composition comprising said at least one poly (phenol sulphide) or a product prepared from said at least one such poly (phenol sulphide), whose odor has disappeared, has been masked, or at least whose odor is much less disagreeable.
• This odor masking thus allows easier handling and less restrictive for the user, and also allows the preparation of finished products whose odors are less unpleasant and less troublesome for end users.
• the present invention relates to a composition
• a composition comprising:
• poly phenol sulfide
• R represents a hydrogen atom or a hydrocarbon group, linear, branched and / or cyclic, totally or partially saturated or unsaturated, containing from 1 to 20 carbon atoms;
• N and n ' which are identical or different, represent, independently of one another, an integer greater than or equal to 1, preferably between 1 and 8, more preferably between 1 and 6, more preferably between 1 and 4; , terminals included;
• P represents an integer between 0 and 100, preferably between 0 and 50, more preferably between 0 and 40 inclusive;
• A represents a hydrogen atom
• T represents a radical of formula (2):
• a and T may together form a single bond, so as to form a cyclic poly (phenol sulfide);
• R represents a linear or branched alkyl radical containing from 1 to 20 carbon atoms, preferably from 1 to 12 carbon atoms
• the radical R is selected from methyl, ethyl, n-propyl, / 'so-propyl, n-butyl, iso-butyl, ie / f-butyl, n-pentyl, amyl, / so-amyl, ie / f-amyl, hexyl, heptyl, octyl and nonyl.
• the radical R may also be substituted by one or more cyclic groups, for example by an aromatic group, and typically R may represent a phenylprop-2-yl radical, as described in application US2007 / 0093613.
• the compounds of formula (1) in which n and n 'each represents the number 1, when m represents 1 or 2 are preferred.
• the compounds of formula (1) ) are those in which m represents 0.
• the compounds of formula (1) for which p represents an integer between 1 and 40, preferably between 2 and 30, and more preferably between 3 and 25 inclusive, are preferred.
• composition according to the present invention may comprise more than one poly (phenol sulphide) of formula (1) and in particular several poly (phenol sulphides) for which n and n ', which are identical or different, are chosen independently of one another from 2, 3 and 4.
• poly (phenol sulphides) for which n and n ', which are identical or different, are chosen independently of one another from 2, 3 and 4.
• the average value of n and the average value of n ' are preferably each close to 2 .
• the p values of the poly (phenol sulfides) may be identical or different from each other, and the average value of p in such poly (phenol sulfide) blends, typically can be from about 5 to about 10 inclusive.
• composition according to the present invention may be formulated with one or more additives or fillers, among which may be mentioned fatty acids, for example stearic acid, silica, for example the silica gel, urea and urea derivatives.
• fatty acids for example stearic acid
• silica for example the silica gel
• urea and urea derivatives may be mentioned.
• poly (phenol sulfides) used in the compositions according to the present invention are well known to those skilled in the art and may be especially poly (phenol sulfides) sold by Arkema under the generic name Vultac. ® , including Vultac ® 2, Vultac ® 3, Vultac ® 5, Vultac ® TB7, Vultac ® 700, Vultac ® 710, Vultac ® TB710, and other Vultac ®
• the components a) of the composition according to the present invention are readily available commercially or can be prepared by any method known to those skilled in the art, and described in the scientific literature. and patents.
• the invention also relates to the compositions comprising the poly (phenol sulfide) derivatives of formula (1) described above and in particular the compounds of formula (1) in which the hydroxyl function of phenol has been modified (for example alkoxylated) and / or the R radicals of the phenolic groups have been modified (for example substituted, functionalized, and the like).
• the amount of masking agent (component b) can vary in large proportions in the range indicated above, depending on the desired effect, the intensity of the odor to be masked, the respective residual contents of various impurities can be present in component (s) a) previously defined, and others.
• Amounts of masking agent less than a few ppm may be too low to achieve the desired effect. Amounts of masking agent greater than 2% can be economically prohibitive, or have adverse effects depending on the intended applications for the poly (phenol sulfides) and will be described later in the description.
• the content of agent (s) masking odor b) is between 0.001% and 1% by weight, inclusive limits, relative to the total weight of the composition, preferably between 0.001% and 0.5% by weight, inclusive, for example about 0.1% by weight.
• the present invention has the advantage of masking the unpleasant odor of at least one poly (phenol sulfide), without chemically modifying the nature.
• the present invention provides a composition comprising a) a major amount of at least one poly (phenol sulfide) of formula (1), or at least one poly (phenol sulfide) derivative of formula (1), at which is added a minor amount of a composition b) masking the unpleasant odor of the component (s) a).
• the masked odor composition according to the present invention may be prepared by any method known per se by simply combining at least one component a) with at least one odor masking composition b).
• at least one composition b) can be added to at least one component a), or vice versa, optionally with stirring and / or possibly heating.
• any known method of mixing and / or heating may be used.
• the preparation of the composition according to the invention may for example be carried out under atmospheric pressure, at a temperature of between 0.degree. C., preferably between room temperature, and 250.degree. C. to 300.degree. C. of component a), when it is in solid form. It is particularly preferred to carry out the mixing at a temperature above the melting temperature of component a).
• the preparation may also be carried out under pressure or under vacuum, at temperatures within the ranges indicated above.
• component b) can be added during the synthesis of component a), and particularly at the end of synthesis of component a), when it is still present at the molten state, or in the reaction solvent, before recovering the component a) in solid form, when the component a) is in solid form at ambient temperature and pressure.
• the period of time required for the preparation of the masked odor composition according to the invention varies according to the nature and the amount of component (s) a) and composition (s) b), but also depending on the chosen temperature and pressure. As a rule, this duration corresponds to the time necessary to obtain a homogeneous mixture and producing the desired effect of odor masking of component (s) a); it is generally between a few seconds and a few minutes, or even one or more hours.
• the preparation process mentioned above can be carried out batchwise (batch process) or continuously.
• the odor masking agent b comprises one or more of the compounds chosen from:
• the odor masking agent thus comprises at least one alcohol b1) which can be of any type and advantageously chosen from monoalcohols, comprising from 1 to 40 carbon atoms, preferably from 6 to 35 carbon atoms, more preferably from 8 to 30 carbon atoms, said carbon atoms forming a linear or branched chain optionally comprising one or more unsaturation (s) in the form of double (s) ) bond (s), and optionally comprising a cyclic structure with 5 or 6 members, saturated, or totally or partially unsaturated.
• monoalcohols comprising from 1 to 40 carbon atoms, preferably from 6 to 35 carbon atoms, more preferably from 8 to 30 carbon atoms, said carbon atoms forming a linear or branched chain optionally comprising one or more unsaturation (s) in the form of double (s) ) bond (s), and optionally comprising a cyclic structure with 5 or 6 members, saturated, or totally or partially unsaturated.
• aryl radical is meant an aromatic hydrocarbon radical, preferably selected from phenyl and naphthyl, optionally substituted with one or more groups selected preferably from alkyl, alkenyl, alkoxy, carbonyl and alkoxycarboyle.
• the aryl radical is a phenyl radical.
• the component b1) is preferably an alcohol containing an aryl radical, more preferably a primary alcohol comprising an aryl radical, and very particularly preferably a hydroxy-alkylbenzene, for example chosen from, and in a manner not limiting, among benzyl alcohol, phenylethanol, propylethanol, butylethanol, and the like, as well as mixtures of two or more of them in all proportions.
• phenols substituted with one or more alkoxy groups can be used as alcohol b1).
• alkoxyphenols mention may be made, for example, and without limitation, of 2-methoxyphenols, and in particular 2-methoxyphenols substituted in the 4-position by an alkyl or alkenyl radical, where alkyl and alkenyl include methyl, ethyl and propyl radicals. , butyls, pentyles, hexyls, propenyls, butenyls, pentenyls and hexenyls, the plural mark on these radicals indicating that their isomers are included in this non-exhaustive list.
• esters b2) of the odor-masking agent b) present in the composition of the invention may in general be of any type known to those skilled in the art, but the esters of the alcohols b1 are particularly preferred. ) listed above, that is to say the esters of primary monoalcohol, preferably having an aromatic ring and more preferably the esters formed from hydroxy-alkylphenols.
• esters mentioned under b2) mention may be made of saturated or unsaturated C 2 -C 2 o acid esters, such as acetates, propionates, butyrates, methylbutyrates, pentanoates, hexanoates, heptanoates, benzoates, hydroxybenzoates, cyclopropylcarboxylates, cyclobutylcarboxylates, cyclopentylcarboxylates, cyclohexylcarboxylates, citrates, caproates, oleates, linoleates, linolenates, alkyl (linear or branched, for example ethyl, propyl , butyl, pentyl, 2-methylbutyl, ⁇ -amyl, hexyl), alkenyl (linear or branched having from 3 to 12 carbon atoms), aryl (for example benzyl), alkyl (linear or branched
• esters b2) there may also be mentioned cyclic esters or lactones, also called alkanolides.
• alkanolides having no double bond and alkanolides having a single intracyclic double bond are preferred.
• esters b2) are more particularly preferred, by way of non-limiting examples, benzyl acetate, phenylethyl acetate, methyl 2-hydroxybenzoate, benzyl 2-hydroxybenzoate, butyrolactones. and alkanolides having from 6 to 12 carbon atoms, for example decanolides, undecanolides, dodecanolides, cyclopentadecanolides, oxacyclohexadecenones, as well as pyranones, and benzopyranones, and mixtures of two or more of these compounds.
• the odor-masking agent b) may further comprise at least one aldehyde b3) and / or at least one ketone b4), and preferably at least one aldehyde and / or at least one ketone corresponding to the formula R a -CO-R b , wherein R a represents a linear, branched or cyclic, saturated or partially or totally unsaturated hydrocarbon-based chain containing 1 to 20 carbon atoms, optionally substituted with one or more radicals chosen from hydroxyl and alkoxy; aryl, and R b represents the hydrogen atom (in the case of aldehydes), or (in the case of ketones) a linear, branched or cyclic, saturated or partially or totally unsaturated hydrocarbon-based chain of 6 to 12 carbon atoms, optionally substituted with one or more radicals selected from hydroxy, alkoxy, cycloalkyl, cycloalkenyl, and aryl, aryl being as defined above.
• aldehydes b3) propanal, butanal, pentanal, hexanal, heptanal, octanal, nonanal, decanal, undecanal, docdecanal, benzaldehyde, geranial, neral, citronellal, as well as their substituted counterparts, for example hydroxydecanal phenylpropanals, phenylbutanals, phenylpentanals, phenylhexanals, hydroxybenzaldehydes, alkoxybenzaldehydes, and the like, as well as their substituted counterparts, and mixtures of two or more of these aldehydes, in all proportions.
• ketones b4) there may be mentioned preferably propanone, butanone, pentanone, hexanone, heptanone, octanone, nonanone, decanone, undecanone the dodecanone, and preferably their substituted counterparts, as well as cyclic ketones among which mention may be made menthone, ⁇ / 'so-menthone, ionones, the methylionones, the phényléthanones, the benzopyranones, 1, 8-cineole, ascaridole, flavonone, calone, galbascone, and others, as well as their substituted counterparts, and mixtures of two or more of these ketones, in all proportions.
• substituted homologues is meant the aforementioned aldehydes and ketones substituted with one or more radicals, which may be, for example, and without limitation, selected from alkyl, hydroxy, aryl, arylalkyl radicals.
• substituted homologs include, but are not limited to, 3- (4-ethylphenyl) -2,2-dimethylpropanal, 3- (2-ethylphenyl) -2,2-dimethylpropanal, 7-hydroxydecanal, 7 hydroxy-3,7-dimethyloctanal, 2-methoxybenzaldehyde, 4-methoxybenzaldehyde, 4- (4-hydroxyphenyl) butan-2-one, and the like, as well as mixtures thereof.
• the odor-masking agent b) may further comprise at least one ether b5), and preferably at least one ether having the formula R ' a -O-R' b , in which R ' a and R ' b , which may be identical or different, represent, independently of each other, a linear, branched or cyclic, saturated or partially or totally unsaturated hydrocarbon-based chain containing 1 to 20 carbon atoms, optionally substituted by one or more radicals chosen among hydroxy, alkoxy, cycloalkyl, cycloalkenyl and aryl, aryl being as defined above.
• ethers b5) which may be symmetrical or non-symmetrical, cyclic or non-cyclic, there may be mentioned, preferably, optionally substituted dialkyl ethers (for example bis-hydroxypropyl ethers), pyrans, furans, benzopyrans, benzofurans, naphthopyrans, naphthofurans, and others, as well as their substituted counterparts, and mixtures of two or more of these ethers in any proportion.
• dialkyl ethers for example bis-hydroxypropyl ethers
• the odor masking agent b) used in the context of the present invention may comprise, in minority amounts, other agents (fragrances) usually used in the field of perfumery, such as fatty acids. glycols, terpene compounds, and others well known to those skilled in the art.
• composition b) intended to mask the odor poly (phenol sulfides), and as described above may, if necessary, see if necessary, furthermore include one or more additives commonly used in the field.
• additives may for example be chosen from, and without limitation, solvents, pigments, dyes, preservatives, biocides, and others.
• the solvents very particularly preferred examples are alcohols, ethers, esters and glycols.
• the solvent is chosen from diethyl phthalate, ethylene glycol, propylene glycol, di-ethylene glycol, dipropylene glycol, polyethylene glycols, polypropylene glycols, and mixtures thereof, and even more advantageously among diethyl phthalate, dipropylene glycol, and mixtures thereof.
• the odor-masking agent used in the composition of the present invention is chosen from odor-masking agents comprising:
• the odor-masking agent used in the composition of the present invention is chosen from odor-masking agents which comprise:
• At least one component b2), at least one component b4), and at least one component b5) are at least one component b2), at least one component b4), and at least one component b5).
• the composition according to the present invention comprises at least one odor masking agent composition b).
• said agent comprises at least one component b1) and / or at least one component b2) and / or at least one component b3), each of the components b1), b2) and b3), when present, is present in an amount greater than or equal to 1%, preferably greater than or equal to 10% by weight relative to the total weight of odor masking agent b).
• the composition according to the present invention comprises at least one odor masking agent composition b) comprising at least one component b2) and / or at least one component b4) and / or at least one component b5), each of component b2), b4) and b5), when present, is present in an amount greater than or equal to 1%, preferably greater than or equal to 10% by weight relative to the total weight of the odor masking agent b).
• odor masking agents b which, when they comprise at least one ketone b4), comprise an amount of ketone (s) b4) of between 0.1% and 40% by weight, preferably between 0.1% and 10% by weight, inclusive, based on the total weight of the odor masking agent.
• the odor-masking agent b) may optionally also comprise up to 20%, preferably from 0.1% to 10%, more preferably from 0.1% to 1% by weight relative to the weight. total of the odor masking agent, at least one fragrance usually used in the field of perfumery.
• the odor masking agent b) comprises:
• the 100% supplement comprising at least one ketone b4) and / or at least one ether b5) and / or one or more other fragrances and / or additives, as indicated above.
• An odor masking agent b) typically adapted for poly (phenol sulfides) according to the present invention, comprises by weight:
• composition noted C1 in the remainder of this disclosure, is particularly suitable for the masking of the odor, for the improvement of the odor, poly (phenol sulfides) of formula (1) described above. (component a), and in particular poly (phenol sulfides) marketed by Arkema under the generic name of Vultac ® .
• the odor masking agent b) comprises:
• the 100% supplement comprising at least one alcohol b1) and / or at least one aldehyde b3) and / or one or more other fragrances and / or additives, as indicated above.
• An odor masking agent b) corresponding to this embodiment and also typically adapted for poly (phenol sulfides) according to the present invention, comprises by weight:
• ketone b4 • at least 1% by weight, and preferably at least 10% by weight of at least one ketone b4) selected from menthone, ⁇ / 'so-menthone, ionones, methylionones the the phényléthanones, the benzopyranones , 1,8-cineole, ascaridole, flavonone, calone, galbascone, and others, as well as their substituted counterparts, and mixtures of two or more of these ketones, in all proportions,
• At least 1% by weight, and preferably at least 10% by weight, of at least one ether b5) chosen from optionally substituted dialkyl ethers (for example bis-hydroxypropyl ethers), pyrans, furans, benzopyrans; benzofurans, naphthopyrans, naphthofurans, and the like, as well as their substituted counterparts, and mixtures of two or more of these ethers in any proportion, and The 100% supplement comprising at least one alcohol b1) and / or at least one aldehyde b3) and / or one or more other fragrances and / or additives, as indicated above.
• optionally substituted dialkyl ethers for example bis-hydroxypropyl ethers
• pyrans for example bis-hydroxypropyl ethers
• furans furans
• benzopyrans benzofurans
• naphthopyrans naphthofurans
• naphthofurans naphthofurans
• composition is also particularly suitable for the masking of the odor, for the improvement of the odor, poly (phenol sulfides) of formula (1) described previously (component a), and in particular poly (phenol sulfides) marketed by Arkema under the generic name of Vultac ® .
• compositions of poly (phenol sulfides) of formula (1) are given by way of examples and have nothing restrictive of the potential diversity of the compositions that the present invention provides as defined by the appended claims.
• a very particularly preferred composition according to the present invention comprises:
• the present invention relates to the use of at least one odor-masking agent b) as it has just been defined for attenuating, or else masking the odor of at least one poly (phenol sulphide), or a composition comprising at least one poly (phenol sulphide), in particular a poly (phenol sulphide) of formula (1) as defined above, and in particular a poly (sulphide phenol) family of Vultac ® marketed by Arkema.
• compositions according to the present invention comprising mainly at least one poly (phenol sulphide) a) and at least one odor-masking agent b) find quite advantageous uses in many fields, and in particular in all of them. known areas of use of poly (phenol sulfides).
• the masked odor compositions according to the invention may for example be used, by way of non-limiting examples, as antioxidant agents and / or thermal stabilizers for plastics or for oils, as flame retardants for plastics or for synthetic or vegetable fibers, as wood preservatives, as disproportionation and bleaching of plant resins, as charge control agents for toner, and others, to name but a few main uses.
• the various products obtained using a masked odor composition according to the invention also have an attenuated odor, or do not present any unpleasant or irritating odor.
• the odor-masking agent present in the composition according to the invention remains stable and makes it possible to obtain products, even when they are prepared at temperatures between 25 and 300 ° C., and do not themselves present an unpleasant odor for the end user, as felt when prepared with polyphenol sulfide compositions with unmasked odor.
• the present invention relates to a manufactured product prepared with at least one composition according to the present invention.
• examples of such products are, by way of non-limiting examples, elastomer-based products, such as tires or tire parts, for example tread, lining, and the like, resin-based products.
• thermoplastics including masterbatches comprising a polymer and at least a poly (phenol sulfide) according to the invention, such as for example the masterbatches sold by MLPC under the trade name Mixland ®, e.g. those in which is dispersed a mixture of poly (phenol sulfide) and urea and to which can be added at least one odor-masking agent b) according to the invention.
• products manufactured and prepared with at least one composition according to the present invention mention may also be made of products based on rosin, based on vegetable fibers, such as cotton or wool, products based on expanded polystyrene, toner components for printing, wood products treated with poly (phenol sulfides), and others.
• composition based on poly (phenol sulfide) with a masked odor Composition based on poly (phenol sulfide) with a masked odor
• PE polyethylene
• each of the drums is placed a crystallizer containing about 25 grams of test composition.
• the casks are kept closed for 24 hours at room temperature. The evaluation is then carried out blind.
• the panelists, 10 come in turn to test a few products per session (maximum 3 products per session). They begin to feel the barrel in which is the poly (phenol sulfide) reference (without odor masking agent), then one of the compositions to be tested.
• the reference poly (phenol sulphide) is Vultac ® 3 marketed by Arkema. This sample is named V.
• the panelists assign, according to their preference, a note to each of the compositions to be tested, compared to the reference which arbitrarily received the grade 5.
• the scores given by the panelists range from 1 (the most pleasant product) to 10 (the most unpleasant product).
• Vultac ® 3 A known amount of Vultac ® 3 (about 25 grams) is put in an oven at a temperature of 165 ° C in an aluminum cup. When the Vultac ® 3 is melted and perfectly stirrable, a given amount of odor masking agent is introduced with a pipette. Stirred with a glass rod for 1 min.
• Vultac ® 3 smell odor (mg,% by weight)
• Vultac ® 3 smell odor (mg,% by weight)
• the two samples are classified in the same group. If the averages are significantly different, the two samples constitute two separate groups (A and B in the illustrative examples of the invention). The same operation is performed to compare all the samples, which ultimately allows to arrive at 1, 2 or more groups, each consisting of samples whose average scores are not significantly different.

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