WO2016005149A1 - Systèmes de polyuréthane peu odorants - Google Patents

Systèmes de polyuréthane peu odorants Download PDF

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Publication number
WO2016005149A1
WO2016005149A1 PCT/EP2015/063385 EP2015063385W WO2016005149A1 WO 2016005149 A1 WO2016005149 A1 WO 2016005149A1 EP 2015063385 W EP2015063385 W EP 2015063385W WO 2016005149 A1 WO2016005149 A1 WO 2016005149A1
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Prior art keywords
foam
additive
polyurethane
fragrances
isocyanate
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PCT/EP2015/063385
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German (de)
English (en)
Inventor
Jörg DIENDORF
Ruediger Landers
Eva Emmrich-Smolczyk
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Evonik Degussa Gmbh
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Publication of WO2016005149A1 publication Critical patent/WO2016005149A1/fr

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/161—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22
    • C08G18/163—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22 covered by C08G18/18 and C08G18/22
    • C08G18/165—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22 covered by C08G18/18 and C08G18/22 covered by C08G18/18 and C08G18/24
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/1825—Catalysts containing secondary or tertiary amines or salts thereof having hydroxy or primary amino groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/1833—Catalysts containing secondary or tertiary amines or salts thereof having ether, acetal, or orthoester groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/20—Heterocyclic amines; Salts thereof
    • C08G18/2081—Heterocyclic amines; Salts thereof containing at least two non-condensed heterocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4804—Two or more polyethers of different physical or chemical nature
    • C08G18/4816—Two or more polyethers of different physical or chemical nature mixtures of two or more polyetherpolyols having at least three hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
    • C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00—Foam properties
    • C08G2110/0008—Foam properties flexible
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2110/00—Foam properties
    • C08G2110/0083—Foam properties prepared using water as the sole blowing agent
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2190/00—Compositions for sealing or packing joints
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2340/00—Filter material
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2350/00—Acoustic or vibration damping material
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2410/00—Soles
    • 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
    • C08K2201/00—Specific properties of additives
    • C08K2201/007—Fragrance additive

Definitions

  • the invention is in the field of polyurethanes and relates in particular to a perfume-containing additive for the production of polyurethane systems, a composition for the production of a polyurethane system, the use of perfume-containing additives in connection with polyurethane foams, a process for the preparation of a polyurethane system, a polyurethane system and the like Use.
  • Polyurethane systems in the context of this invention are, for. Polyurethane coatings, polyurethane adhesives, polyurethane sealants, polyurethane elastomers or, in particular, polyurethane foams / foams.
  • Polyurethane foams are used in a wide variety of applications due to their excellent mechanical and physical properties.
  • a particularly important market for various types of polyurethane foams such as conventional ether and ester polyol based flexible foams, cold foams (often referred to as HR foams), viscoelastic foams, rigid foams, integral foams and microcellular foams, as well as foams whose properties lie between these classifications , such as B. semi-rigid systems, e.g. the automotive and furniture industries.
  • polyurethane foams are also extremely popular with end users and are in high demand, e.g. in connection with mattresses.
  • the object of the present invention was therefore to provide as low-odor polyurethanes, in particular polyurethane foams.
  • perfume-containing additives wherein at least 5 wt .-% of the fragrances contained therein, wt .-% based on the total amount of all fragrance contained in the additive, a ClogP value> 4 and a boiling point> 275 ° C have , the provision of low odor to odorless polyurethanes, especially polyurethane foams allow.
  • the present invention thus provides a fragrance-containing additive for the production of polyurethane systems, in particular a polyurethane foam, wherein at least 5 wt .-% of the fragrance contained in the additive, based on the total amount of all the fragrances contained in the additive, a ClogP value> 4 and a Boiling point> 275 ° C have.
  • the subject invention makes it possible that the emanating from polyurethane systems odor nuisance can be reliably minimized or advantageously even completely prevented. This allows e.g. as a result, the provision of such mattresses that smell significantly less or not at all on the first day after unpacking.
  • the additive of the invention thus allows for the first time the provision of polyurethane systems (in particular polyurethane foam), in which the odor problem is overcome.
  • the intensity of the smell is reduced; the acceptance of the possibly remaining residual odor is increased, ie the odor of the conventional PU system, in particular foam is classified as unpleasant as the one in which the additive according to the invention with otherwise identical production method is used; the resulting PU system, in particular foam, is odorless; in the optimal case, even an odor extinction can take place.
  • fragment is well known to those skilled in the art. These are understood to mean chemical compounds with human-perceivable odor.
  • fragrances include geraniol (floral odor), citral (smell of citrus), hex-3-en-1-ol (smell of grass and green leaves), thujone (herbaceous odor), (-) - carvone (mint Smell), santalol (woody odor).
  • Fragrances preferred according to the invention are fragrances, ie fragrances with a pleasant odor effect for humans.
  • fragrances is known to those skilled in the art Fragrances are used, for example, in alcoholic solution for the production of perfumes, in order to produce a lasting fragrance
  • kakosmophoren groups such as 3-methyl-1 Butanthiol
  • the "ClogP value” is also well known to those skilled in the art, in particular from the patent literature. It is due to the octanol / water partition coefficient.
  • the octanol / water partition coefficient of a chemical compound, such as a fragrance is the ratio between its equilibrium concentration in octanol and in water. Since these distribution coefficients often have high values, eg 1000 or higher, they are more conveniently given in the form of their base 10 logarithm, one speaks of the so-called log P value.
  • logP values can most conveniently be calculated by the "CLOGP" program available from Daylight Chemical Information Systems, Inc., (Daylight CIS), Irvine, California.
  • the "calculated logP values” are also documented in the literature or accessible via the "CLOGP” program of the Daylight Chemical Information Systems. If only experimental logP is available, it is possible to use the experimental logP value instead of the ClogP value.
  • the "calculated logP” (this is the ClogP value) is determinable by the Harsch and Leo fragment approach (see A. Leo, Comprehensive Medicinal Chemistry, Vol. 4, C. Harsch, PG Sammens, JB Taylor and CA Ransden, Eds., P. 295, Pergamon Press, 1990, incorporated herein by reference). The fragment approach is based on the chemical structure of each of the Perfume ingredients and takes into account the numbers and types of atoms, the atomic bondability and chemical bonding.
  • boiling point values may be e.g. from various known chemical manuals and databases. If a boiling point is indicated only at a different pressure, typically a pressure lower than the normal pressure of 760 mm Hg, the boiling point at normal pressure can be determined approximately with the help of boiling point pressure nomographs such as those described in "The Chemist's Companion", AJ Gordon and RA Ford, John Wiley & Sons Publishers, 1972, pp. 30-36, are incorporated herein by reference.
  • the perfume-containing additive it is necessary for the perfume-containing additive to have at least 5% by weight, based on the sum of the fragrances contained in the additive, of perfumes having a ClogP value> 4 and a boiling point> 275 ° C.
  • the indicated indices may represent both absolute numbers and averages. In the case of polymeric compounds, the indices preferably represent average values. According to a preferred embodiment of the invention, at least 10% by weight, preferably at least 15% by weight, advantageously at least 20% by weight, more preferably at least 25% by weight and in particular at least 30 wt .-% of the odoriferous substances contained in the additive a ClogP value> 4 and a boiling point> 275 ° C, wherein a Upper limit, for example, at 70 wt .-%, 60 wt .-%, 50 wt .-% or 40 wt .-% may be, wt .-% in each case based on the sum of the fragrances contained in the additive.
  • Fragrances with a ClogP value> 4 and boiling point> 275 ° C are well known to the person skilled in the art, in particular according to a preferred embodiment of the invention they are selected from the group comprising ambrettolide, amyl cinnamic aldehyde, amyl cinnamaldehyde dimethyl acetal.
  • fragrances with a ClogP value> 4 and boiling point> 275 ° C can be used.
  • the aforesaid fragrances have proven to be particularly useful in accomplishing the objects of this invention and are particularly conducive to, for the purposes of this invention, e.g. reduce the intensity of the end product odor (e.g., a PU mattress), increase the acceptance of any residual odor, and render the resulting product more odorless overall.
  • the perfume-containing additive may in principle comprise, in addition to the perfume, other components, such as e.g. Solvents, emulsifiers and / or antioxidants. Other components may also be included in the perfume-containing additive, such as e.g. components typical of PU application, e.g. tertiary amines and / or silicone stabilizers.
  • dipropylene glycol is used for the perfume-containing additive.
  • Other solvents commonly used in perfumery such as, in particular, dimethyl phthalate, diethyl phthalate, propanol and isopropyl alcohol, may e.g. also be used.
  • Dipropylene glycol is odorless and not a fragrance in the sense of this invention. typical
  • Solvents such as, in particular, the said dimethyl phthalate, diethyl phthalate, propanol and isopropyl alcohol, and e.g. Ethanol, toluene, etc. are not fragrances in the sense of this invention.
  • Suitable antioxidants for the perfume-containing additive are e.g. Butylhydroxyanisole, tocopherol (e) and butylhydroxytoluene. Others, in particular in perfumery usual
  • Antioxidants can also be used.
  • Suitable emulsifiers for the perfume-containing additive are e.g. nonionic emulsifiers, ie surfactants which do not form ions in aqueous solution, e.g. Fatty alcohols (eg, lauryl, cetyl, stearyl or palmityl alcohol), partial fatty acid esters of polyhydric alcohols with saturated fatty acids (for example, glycerol monostearate, pentaerythritol monostearate, ethylene glycol monostearate, propylene glycol monostearate), partial fatty acid esters of polyhydric alcohols with unsaturated fatty acids (for example, glycerol monooleate, pentaerythritol monooleate); Polyoxyethylene esters of fatty acids (eg polyoxyethylene stearate), polymerization products of ethylene oxide and propylene oxide with fatty alcohols (fatty alcohol polyglycol ethers) or fatty acids
  • the odoriferous additive according to the invention contains> 50% by weight, preferably> 60% by weight, in particular> 70% by weight, of fragrances, based on the total additive.
  • the additive according to the invention can advantageously contain up to 50% by weight, preferably up to 40% by weight, in particular up to 30% by weight of solvent, in particular dipropylene glycol.
  • suitable antioxidants may be present in amounts ⁇ 2% by weight, based on the total additive, with a lower limit of 0.001% by weight.
  • suitable emulsifiers may be present in amounts of ⁇ 2% by weight, based on the total additive, a lower limit being 0.001% by weight.
  • an odiferous additive according to the invention may comprise 50-95% by weight of fragrances, 5-50% by weight of solvent, especially dipropylene glycol, optionally 0.001-2% by weight of antioxidant and optionally 0.001-2% by weight of emulsifier (s) ,
  • the fragrance-containing additive according to the invention may further comprise one or more, preferably tertiary amines, one or more silicone stabilizers.
  • a perfume-containing additive according to the invention may contain silicone stabilizers, e.g. in an amount of> 1 wt .-%, advantageously> 30 wt .-%, preferably> 40 wt .-%, in particular> 50 wt .-%.
  • the odoriferous additive according to the invention comprises at least 5% by weight, preferably at least 10% by weight, in particular at least 15% by weight of fragrances having a CbgP value ⁇ 3, an upper limit e.g. can be at 50 wt .-%, 40 wt .-%, 30 wt .-% or 20 wt .-%, wt .-% in each case based on the sum of the fragrances contained in the additive.
  • Fragrances with a ClogP value ⁇ 3 are known in principle to the person skilled in the art, in particular the fragrances having a ClogP value ⁇ 3 according to a further preferred embodiment of the
  • Invention selected from the group menthone, phenoxyethanol, Benzyldimethylcarbinolacetat. Piperonal, isobutyl salicylate, phenoxyethyl isobutyrate, anisaldehyde, fluoroacetate, rose oxide, Cyclal C. Fruten, ethyl 2-methyl butyrate.
  • fragrances have once again proven particularly useful to achieve the objectives of this invention and are particularly useful in the context of this invention, for example, to reduce the intensity of the end product odor (eg a PU mattress), the acceptance of possibly To increase remaining odor and make the resulting product odorless overall.
  • end product odor eg a PU mattress
  • the additive according to the invention contains fragrances having a boiling point ⁇ 250 ° C, advantageously in amounts of 5 to 40 wt .-%, for example 5 to 30 wt .-% or 5 to 20 Wt .-% or 5 to 15 wt .-%, wt .-% in each case based on the sum of the odoriferous substances contained in the additive, in particular selected from the group comprising linalool, anisaldehyde, rose oxide, Cyclal C, ethyl 2-methyl butyrate, Allo ocimene, allyl heptanoate, cis-3-hexenyltiglate, citronellol, carvacrol, camphene, benzyl butyrate, trans-anethole, citronellyl acetate, citronellylnitrile, cyclohexylethyl acetate, decyl aldehy
  • fragrances with a boiling point ⁇ 250 ° C can be used.
  • the aforesaid fragrances have proven to be particularly advantageous in achieving the objects of this invention and are particularly useful in the context of this invention e.g. reduce the intensity of the end product odor (e.g., a PU mattress), increase the acceptance of any residual odor, and render the resulting product more odorless overall.
  • an additive according to the invention may advantageously comprise the following components
  • fragrances having a ClogP value> 4 and a boiling point> 275 ° C, wherein an upper limit, for. may be 70% by weight, 60% by weight, 50% by weight or 40% by weight,
  • perfumes having a ClogP ⁇ 3 with an upper limit e.g. may be 50% by weight, 40% by weight, 30% by weight or 20% by weight,
  • fragrances having a boiling point ⁇ 250 ° C, advantageously in amounts of 5 to 40% by weight, wt .-% at a), b), c) each based on the sum of the fragrance contained in the additive include, wherein the inventive additive contains> 50 wt .-%, preferably> 60 wt .-%, in particular> 70 wt .-%, fragrances, based on the total additive, and wherein in the additive according to the invention at least 5 different, preferably at least 10 different and in particular at least 15 different fragrances are contained. It has also proven to be advantageous in the context of the invention to optionally use at least partially encapsulated fragrances.
  • encapsulated fragrances are preferably fragrances which are encapsulated in microcapsules.
  • Microcapsules and their preparation are known to those skilled in the art.
  • the microcapsules which can be used according to the invention may preferably be water-soluble and / or water-insoluble microcapsules. Preferably, however, they are water-insoluble microcapsules.
  • the release of active substance from the microcapsule can take place during and / or after PU foam production.
  • the microcapsules usable according to the invention are water-insoluble microcapsules
  • the wall material of the microcapsules being polyurethanes, polyolefins, polyamides, polyesters, polysaccharides, epoxy resins, silicone resins and / or polycondensation products of carbonyl compounds and compounds containing NH groups may include.
  • the water-insoluble microcapsules are drivable.
  • microcapsules means such microcapsules, which can be opened or wrenched by mechanical rubbing or by pressure, as it arises, for example, when the human body is lying on a mattress, so that a content release results only as a result of mechanical action.
  • Preferred microcapsules which can be used according to the invention have diameters in the range from 0.05 to 500 ⁇ m, preferably between 5 and 150 ⁇ m, in particular between 10 and 100 ⁇ m, for example. 10-80 [im.
  • the core or (filled) cavity enclosing shell of the microcapsules has a thickness in the range between advantageously about 0.01 and 50 ⁇ , preferably between about 0, 1 ⁇ and about 30 ⁇ , in particular between about 0.5 ⁇ and about 8 pm.
  • microcapsules, which have the aforementioned diameter and shell thickness are drivable in the context of the invention.
  • microcapsule preparation as such is well known to those skilled in the art. Suitable methods of microcapsule preparation are familiar to those skilled in the art and are e.g. in US 387052, in US Pat. No. 3,516,941, in US Pat. No. 3,415,758 or also in EP 0026914 A1.
  • the latter describes, for example, the production of microcapsules by acid-induced condensation of melamine-formaldehyde precondensates and / or their C1-C4-alkyl ethers in water, in which the hydrophobic material forming the capsule core is dispersed, in the presence of a protective colloid.
  • melamine-urea-formaldehyde microcapsules or melamine-formaldehyde microcapsules or urea-formaldehyde microcapsules e.g. available from 3M Corporation or BASF.
  • Suitable microcapsules are e.g. also described in WO 2001/049817 A2.
  • the water-insoluble microcapsules which can be used according to the invention in particular the aminoplast capsules for example, can be incorporated particularly well and homogeneously into the resulting body, for example a mattress, in the foaming process.
  • these capsules After the production of the body, for example the mattress, these capsules then usually have a certain brittleness, so that a targeted release of fragrance from the capsule can take place by the action of mechanical force. In this way, even after prolonged storage under the influence of mechanical force targeted a fragrance can be caused.
  • the additive according to the invention contains skin care ingredients such as almond oil, green tea extract or aloe vera preparations, D-panthenol, plankton extract, vitamin C, urea and / or glycine, in particular in microencapsulated form (preferably water-insoluble Microcapsules), so there is also a preferred embodiment of the invention.
  • skin care ingredients such as almond oil, green tea extract or aloe vera preparations, D-panthenol, plankton extract, vitamin C, urea and / or glycine, in particular in microencapsulated form (preferably water-insoluble Microcapsules), so there is also a preferred embodiment of the invention.
  • microencapsulated form preferably water-insoluble Microcapsules
  • microcapsulated form preferably water-insoluble Microcapsules
  • microcapsules which contain both fragrances and ingredients for the care of the skin.
  • skin-care active substances are preferably also essential oils, such as Angelica fine - Angelica archangelica, rosewood -
  • a targeted equipment of PU systems such as. PU foam, for example with skin care capsule systems.
  • a mattress can be provided in this way, which gives off skin-care substances during use.
  • the additive according to the invention contains fragrance precursor.
  • a fragrance precursor is a compound which releases a desired odor and / or perfume molecule by the breaking of a chemical bond, for example by hydrolysis.
  • a desired perfume raw material is chemically combined with a carrier, preferably a slightly volatile or moderately volatile carrier. The combination results in a less volatile and more hydrophobic perfume precursor with improved attachment to fabrics.
  • the fragrance is then released by disrupting the binding between the perfume raw material and the carrier, for example, by a change in pH (eg, by perspiration), humidity, heat, and / or sunlight.
  • the perfume raw material for use in perfume precursors are typically saturated or unsaturated volatile compounds containing an alcohol, an aldehyde and / or a ketone group. Fragrance raw materials useful herein include any fragrant substances or mixtures of substances.
  • fragrance precursor obey the following formula in which R is hydrogen, linear C 1 -C 8 -alkyl, branched C 3 -C 20 -alkyl, cyclic C 3 -C 20 -alkyl, branched cyclic C 6 -C 20 -alkyl, linear C 6 -C 20 -alkenyl, branched C 6 -C 20 -alkenyl, cyclic C6 -C 20 alkenyl, branched cyclic C 6 -C 20 alkenyl, substituted or unsubstituted C 6 -C 20 aryl, and mixtures thereof; R, R 2 and R 3 are independently linear, branched or substituted C 1 -C 20 alkyl; linear, branched or substituted C 2 -C 20 alkenyl; substituted or unsubstituted C3-C20 cyclic alkyl; substituted or unsubstituted C 6 -C 20 aryl, substitute
  • R - C - OR 1 in which R is hydrogen, methyl, ethyl, phenyl and mixtures thereof; R is selected from the group consisting of 4- (1-methylethyl) cyclohexanemethyl, 2,4-dimethyl-3-cyclohexen-1-ylmethyl, 2,4-dimethylcyclo-hex-1-ylmethyl, 2,4,6- Trimethyl 3-cyclohexen-1-ylmethyl, 2-phenylethyl, 1- (4-isopropylcyclohexyl) ethyl, 2,2-dimethyl-3- (3-methylphenyl) propan-1-yl, 3-phenyl-2-propene 1-yl, 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) -2-buten-1-yl, 3-methyl-5-phenyl-pentan-1-yl, 3-methyl-5- (2,2,3-trimethyl-3-cyclopenten-1-yl) -4-penten-2-yl,
  • R 1 is hydrogen or R
  • R 2 and R 3 are each independently selected from the group consisting of linear C 1 -C 20 -alkyl, branched C 3 -C 20 -alkyl, cyclic C 3 -C 20 -alkyl, branched cyclic C 6 -C 20 -alkyl, linear C 6 -alkyl C20-alkenyl.
  • inventively used bare fragrance precursor obey the following formula
  • R 1 , R 2 , R 3 and R 4 independently of one another are linear, branched or substituted C 1 -C 20 -alkyl; linear, branched or substituted C2-C20 alkenyl; substituted or unsubstituted cyclic C5-C20-alkyl; substituted or unsubstituted C 6 -C 20 aryl, substituted or unsubstituted C 2 -C 40 alkyleneoxy; substituted or unsubstituted C3-C40 alkyleneoxyalkyl; substituted or unsubstituted C6-C40 alkylenearyl; substituted or unsubstituted C6-C32 aryloxy; substituted or unsubstituted C6-C40 alkylene-oxyaryl; C 6 -C 40 oxyalkylene aryl; and mixtures thereof.
  • fragrances used comprise silicic acid ester mixtures which are silicic acid esters of the formulas (I) and (II) immediately following
  • the silicic acid esters of formulas (I) and (II) each contain at least one Riechstoffalkoholrest and / or Bizidalkoholrest.
  • the silicic acid ester mixtures can be used in particular in the invention (preferably water-insoluble) microcapsules used. It has surprisingly been found that the presence of the silicic acid ester mixtures results in that the purpose of the invention can be further improved.
  • Particularly suitable perfume precursors are reaction products of compounds comprising at least one primary and / or secondary amine group, for example an amino-functional polymer, especially an amino-functional silicone, and a perfume ingredient selected from ketone, aldehyde and mixtures thereof.
  • an amino-functional polymer especially an amino-functional silicone
  • a perfume ingredient selected from ketone, aldehyde and mixtures thereof preferably water-insoluble microcapsules.
  • the additive according to the invention is used, as described, for the preparation of polyurethane systems.
  • the preparation of the polyurethane systems using the additive according to the invention can advantageously be carried out in the usual way.
  • Another object of the present invention is a process for the preparation of a polyurethane system by reacting one or more polyol components with one or more isocyanate components in the presence of one or more catalysts, the Reactions are cyanate isocyanate-polyol and / or isocyanate-water and / or the isocyanate trimerization, wherein a fragrance-containing additive according to the invention, as described above, is used.
  • a fragrance-containing additive according to the invention as described above, is used.
  • the polyurethane system may in particular be polyurethane coatings, polyurethane adhesives, polyurethane sealants, polyurethane elastomers or in particular polyurethane foams / foams.
  • Another object of the present invention is a polyurethane system, in particular polyurethane foam / foam, prepared using an additive according to the invention as described above, in particular comprising 0.00001 to 5 wt .-% of the additive.
  • the Polyurethanschau m / foam is in particular polyurethane hard foam m, flexible polyurethane foam, viscoelastic foam, HR foam, semi-rigid polyurethane foam, thermoformable polyurethane foam or integral foam.
  • isocyanate component all isocyanates, in particular the aliphatic, cycloaliphatic, araliphatic and preferably aromatic polyfunctional isocyanates known per se, can be used in the process according to the invention.
  • Suitable isocyanates in the sense of this invention are preferably all polyfunctional organic isocyanates, such as 4,4'-diphenylmethane diisocyanate (MDI) and its isomers, toluene diisocyanate (TDI), hexamethylene diisocyanate (HMDI) and isophorone diisocyanate (IPDI).
  • MDI 4,4'-diphenylmethane diisocyanate
  • TDI toluene diisocyanate
  • HMDI hexamethylene diisocyanate
  • IPDI isophorone diisocyanate
  • Particularly suitable is the mixture known as "polymeric MDI"("crudeMDI") of MDI and higher condensed analogues having an average functionality of 2 to 4, and the various isomers of TDI in pure form or as a mixture of isomers.
  • Particularly preferred isocyanates are mixtures of TDI and MDI.
  • polyol suitable polyols in the context of this invention are preferably all organic substances having a plurality of isocyanate-reactive groups, and their preparations can be used.
  • Preferred polyols are all polyether polyols and polyester polyols customarily used for the preparation of polyurethane systems, in particular polyurethane foams.
  • Polyether polyols may, for. B. be obtained by reaction of polyhydric alcohols or amines with alkylene oxides.
  • Polyester polyols are preferably based on esters of polybasic carboxylic acids (which may be either aliphatic, for example adipic acid or aromatic, for example phthalic acid or terephthalic acid) with polyhydric alcohols (usually glycols).
  • polyhydric alcohols usually glycols.
  • natural oils based on natural oils natural oil based polyols, NOPs
  • These polyols are derived from natural oils such as soy or palm oil and can be used unmodified or modified.
  • polyols are those obtained as prepolymers by reacting polyol with isocyanate in a molar ratio of 100: 1 to 5: 1, preferably 50: 1 to 10: 1. Such prepolymers are preferably used dissolved in polyol, wherein the polyol preferably corresponds to the polyol used to prepare the prepolymers.
  • Yet another class of preferably usable polyols are the so-called Greet al. (polymer polyols). These are characterized by the fact that they contain solid organic fillers to a solids content of 40 wt .-% or more in disperse distribution.
  • SAN polyols These are highly reactive polyols containing a copolymer based on styrene / acrylonitrile (SAN) dispersed.
  • PHD polyols These are highly reactive polyols which also contain polyurea in dispersed form.
  • PIPA Polyols These are highly reactive polyols which contain a polyurethane in dispersed form, for example, by in situ reaction of an isocyanate with an alkanolamine in a conventional polyol.
  • the solids content which depending on the application may preferably be between 5 and 40% by weight, based on the polyol, is responsible for an improved cell opening, so that the polyol is particularly foamable controlled with TDI and no shrinkage of the foams occurs.
  • the solid acts as an essential process aid. Another function is to control the hardness via the solids content, because higher solids contribute to a higher hardness of the foam.
  • formulations containing solids-containing polyols are significantly less intrinsically stable and therefore, in addition to the chemical stabilization by the crosslinking reaction, rather require physical stabilization as well.
  • these may be e.g. alone or e.g. be used in admixture with the above unfilled polyols.
  • a ratio of isocyanate component to polyol component, expressed as an index, in the context of this invention is in the range from 10 to 1000, preferably 40 to 350. This index describes the ratio of actually used isocyanate to isocyanate (calculated for a stoichiometric reaction with polyol).
  • An index of 100 stands for a molar ratio of the reactive groups of 1 to 1.
  • Suitable catalysts which can be used in the process according to the invention are preferably substances which contain the gel reaction (isocyanate-polyol), the blowing reaction (isocyanate-polyol). Water) or catalyze the di- or trimerization of the isocyanate.
  • Typical examples are amines such as triethylamine, dimethylcyclohexylamine, tetramethylethylenediamine, tetramethylhexanediamine, pentamethyldiethylenetriamine, pentamethyldipropylenetriamine, triethylenediamine, dimethylpiperazine, 1, 2-dimethylimidazole, N-ethylmorpholine, tris (dimethylaminopropyl) hexahydro-1,3,5-triazine, dimethylaminoethanol, dimethylaminoethoxyethanol and bis (dimethylaminoethyl) ethers, tin salts of organic carboxylic acids, tin compounds such as dibutyltin dilaurate, and potassium salts such as potassium acetate.
  • reactive amines such as dimethylaminoethoxyethanol, which are chemically bonded in the polyurethane system, in particular foam, corresponds to a preferred embodiment of the invention.
  • Suitable water contents in the process according to the invention depend on whether or not physical blowing agents are used in addition to the water. In the case of pure water-driven foams, the values are typically preferably 1 to 20 pphp, if other blowing agents are used in addition, the amount of use is reduced to usually e.g. 0 or e.g. 0, 1 to 5 pphp. In order to obtain a high mah weight, preferably neither water nor other propellants are used.
  • Suitable physical blowing agents for the purposes of this invention are gases, for example liquefied C0 2 , and volatile liquids, for example hydrocarbons having 4 or 5 carbon atoms, preferably cyclo, iso and n-pentane, hydrofluorocarbons, preferably HFC 245fa, HFC 134a and HFC 365mfc, chlorofluorocarbons, preferably HCFC 141b, oxygen-containing compounds such as methyl formate and dimethoxymethane, or chlorinated hydrocarbons, preferably dichloromethane and 1, 2-dichloroethane.
  • ketones eg acetone
  • aldehydes eg methylal
  • compositions of the invention may contain one or more stabilizers.
  • stabilizers are, in particular, carbon atoms containing silicon compounds, preferably selected from the polysiloxanes, polydimethylsiloxanes, organomodified polysiloxanes, polyether-modified polysiloxanes and polyether-polysiloxane copolymers.
  • Si compounds As one or more carbon atoms having silicon compounds, the substances mentioned in the prior art can be used. Preferably, those Si compounds are used which are particularly suitable for the particular type of foam. Suitable siloxanes are described, for example, in the following documents: EP 0839852, EP 1544235, DE
  • Si compounds can be carried out as described in the prior art. Suitable examples are for. In US 4147847, EP 0493836 and US 4855379.
  • organically modified Si compounds can be used.
  • Particularly preferred, usable organically modified Si compounds are, for example, those according to the following formula (IV)
  • k 0 to 22, preferably 2 to 10, more preferably 2
  • m 0 to 400, preferably 0 to 200, particularly preferably 2 to 100
  • n 0 to 50, preferably 0.5 to 20, particularly preferably 0.7 to 9
  • o 0 to 10, preferably 0 to 5, particularly preferably 0
  • p 0 to 10, preferably 0 to 5, particularly preferably 0
  • R 2 R or R 3
  • R independently of one another alkyl or aryl radicals or H, preferably methyl, ethyl, propyl or phenyl, preferably methyl or phenyl
  • R 3 organic modifications, for example polyethers or a monovalent radical having 1 to 30 C atoms with at least one heteroatom selected from the group N. S, O, P, F, Cl, Br
  • R 3 in formula (IV) are preferably radicals from the group
  • R 5 alkyl, aryl, urethane, carboxyl, silyl or H, preferably H, -Me, or -C (0) Me
  • R 4 alkyl, aryl, which may optionally be interrupted by oxygen, particularly preferably H, Me,
  • a 0 to 100, preferably 0.5 to 70, particularly preferably 1 to 40
  • b 0 to 100, preferably 0.5 to 70, particularly preferably 0 to 40
  • c 0 to 50, preferably 0 to 15, particularly preferably 0
  • unmodified Si compounds can be used.
  • r 0 to 50, preferably 1 to 40, particularly preferably 2 to 30.
  • the abovementioned Si compounds in particular of the formula (IV) and / or (V), can be used individually or in combination with one another.
  • a compatibilizer may additionally be used. This may be selected from the group of aliphatic or aromatic hydrocarbons, particularly preferably aliphatic polyethers or polyesters.
  • the siloxane compounds of the formula (IV) may be advantageous if in the siloxane compounds of the formula (IV) at least 10 equivalents (and at most 50 equivalents) of the radicals R 2 are alkyl groups having 8 to 22 carbon atoms (based on the total number of radicals R 2 in the siloxane).
  • silicon compounds Preferably, from 0.05 to 10 parts by mass of silicon compounds can be used per 100 parts by mass of polyol components.
  • Suitable optional flame retardants in the context of the present invention are preferably liquid organic phosphorus compounds, such as halogen-free organic phosphates, e.g. Triethyl phosphate (TEP), halogenated phosphates, e.g. Tris (1-chloro-2-propyl) phosphate (TCPP) and tris (2-chloroethyl) phosphate (TCEP) and organic phosphonates, e.g. Dimethylmethanephosphonate (DMMP),
  • TEP Triethyl phosphate
  • TCPP Tris (1-chloro-2-propyl) phosphate
  • TCEP tris (2-chloroethyl) phosphate
  • organic phosphonates e.g. Dimethylmethanephosphonate (DMMP)
  • DMPP Dimethylpropane phosphonate
  • APP ammonium polyphosphate
  • red phosphorus e.g., sodium phosphate
  • halogenated compounds for example halogenated polyols, and solids such as expanded graphite and melamine are suitable as flame retardants.
  • polyurethane systems in particular polyurethane foams can be prepared, which are particularly odorless.
  • polyurethane is to be understood in the context of the invention in particular as a generic term for a polymer prepared from di- or polyisocyanates and other isocyanate-reactive species, such as amines, the urethane bond does not have to be exclusive or predominant type of bond. Also, polyisocyanurates and polyureas are expressly included.
  • the preparation according to the invention of polyurethane systems, in particular polyurethane foams or the preparation of the polyurethane systems / polyurethane foams can be carried out by all methods familiar to the person skilled in the art, for example by hand mixing or preferably by means of high pressure or low pressure foaming machines.
  • the process according to the invention can be carried out continuously or batchwise. A discontinuous implementation of the method is preferred in the production of molded foams, refrigerators or panels. Continuous process control is preferred in the manufacture of insulation boards, metal composite elements, blocks or spraying processes.
  • the perfume-containing additives used according to the invention can preferably be added directly before or else only during the reaction (to form the urethane bonds).
  • the combination / addition of the compound takes place in a mixing head, as well as in a batch process for finished polyol systems.
  • a subsequent addition of the additive to the otherwise finished product is also included in the invention.
  • the polyurethane systems according to the invention may preferably contain from 0.0001 to 10% by weight, advantageously from 0.005 to 5% by weight, in particular from 0.01 to 3% by weight, based on the total composition of the polyurethane system, of the additive according to the invention.
  • the polyurethane systems of the invention may preferably be a polyurethane foam, in particular z.
  • a polyurethane hardshell m a flexible polyurethane foam, a viscoelastic foam, an HR foam, a semi-rigid polyurethane foam, a thermoverform ble
  • the polyurethane systems of the invention preferably polyurethane foams, z.
  • 5-component foam foam (1 1, 5-component foam foam is a foam that is produced by destroying a container in the can), wood imitation, model foam , Foam packaging, mattress, furniture upholstery, automotive seat cushion, headrest, instrument panel, automotive interior trim, automotive headliner, sound absorbing material, steering wheel, shoe sole, carpet back foam, filter foam, caulk, sealant and adhesive, or used to make such products.
  • compositions for producing polyurethane foam comprising at least one urethane and / or isocyanurate catalyst, at least one blowing agent, at least one isocyanate component and an inventive additive.
  • composition in this sense also encompasses multicomponent compositions in which two or more components are to be mixed to produce a chemical reaction which results in the production of polyurethane foam.
  • composition in this sense comprises in particular the mixture (mixture) of at least one urethane and / or isocyanurate catalyst, at least one blowing agent, at least one isocyanate component and at least one polyol component and an additive according to the invention.
  • a preferred composition of the invention for producing polyurethane foam may include polyol e.g. in amounts of from 25 to 75% by weight, water e.g. in amounts of 1 to 7% by weight, catalyst e.g. in amounts of 0.05 to 3% by weight, physical blowing agent e.g. in amounts of 0 to 25% by weight (for example 0.1 to 25% by weight), stabilizers (such as, for example, Si-containing and non-Si-containing, in particular Si-containing, and non-Si-containing organic stabilizers and surfactants) eg in amounts of 0.3 to 5% by weight, isocyanate e.g. in amounts of from 20 to 50% by weight and the additive to be used according to the invention, e.g. in amounts of from 0.00001 to 5% by weight (preferably 0.00005 to 2.5% by weight).
  • polyol e.g. in amounts of from 25 to 75% by weight
  • water e.g. in amounts of 1 to 7% by weight
  • catalyst e.g.
  • Another object of the invention is the use of the additives according to the invention to improve the odor of polyurethane foams and / or to provide odorless polyurethane foams.
  • the addition of the additives according to the invention can, as described above, to the polyurethane system (in particular polyurethane foam), preferably in an amount of 0.00001 to 10 wt .-%, advantageously 0.005 to 5 wt .-%, in particular 0.01 to 3 % By weight, based on the total weight of the polyurethane system (in particular polyurethane foam), wherein the addition may be effected before, during or after the preparation of the polyurethane system (in particular the polyurethane foam).
  • Another object of the invention is a polyurethane system (in particular
  • Polyurethane foam containing additives as described above, in an amount of preferably 0.001 to 10 wt .-%, advantageously 0.005 to 5 wt .-%, in particular 0, 10 to 3 wt .-% based on the total weight of the polyurethane system (in particular Polyurethane foam), in particular obtainable by adding the additives before, during or after the preparation of the polyurethane system, in particular polyurethane foam.
  • odor absorbers include, on the one hand, silicates, such as, preferably, phyllosilicates, e.g. Montmorillonite, kaolinite, bentonite and talc.
  • phyllosilicates e.g. Montmorillonite, kaolinite, bentonite and talc.
  • supplementary odor absorbers are, for example, zeolites,
  • Zinc ricinoleate, cyclodextrins and chlorophyll It has become within the scope of the invention especially the complementary, but purely optional use of Zinkricinoleat and / or cyclodextrins proven.
  • the aforementioned optionally usable known odor absorbers can, if desired, be used in amounts of up to 5% by weight, for example if desired in amounts of from 0.001 to 3% by weight.
  • Another object of the invention is the use of the polyurethane systems according to the invention, in particular foams, as refrigerator insulation, insulation board, sandwich element, pipe insulation, spray foam, 1- & 1, 5-component can foam, wood imitation, model foam, packaging foam, mattress, furniture upholstery, material in Automotive interiors, automotive seat cushion, headrest, instrument panel, automotive interior trim, automotive headliner, sound absorbing material, steering wheel, shoe sole, carpet back foam, filter foam, sealing foam, sealant and adhesive or for the production of corresponding products, in particular as a material in motor vehicle interiors.
  • foams as refrigerator insulation, insulation board, sandwich element, pipe insulation, spray foam, 1- & 1
  • 5-component can foam, wood imitation, model foam, packaging foam, mattress, furniture upholstery, material in Automotive interiors, automotive seat cushion, headrest, instrument panel, automotive interior trim, automotive headliner, sound absorbing material, steering wheel, shoe sole, carpet back foam, filter foam, sealing foam, sealant and adhesive or for the production of corresponding products, in particular as a material in motor vehicle interiors.
  • a perfume-containing additive according to the invention was foamed in a flexible polyurethane foam (A).
  • the fragrance limonene (boiling point 177.6 ° C., clogP 4.35) was foamed in otherwise identical manner in a flexible polyurethane foam (B).
  • each case used fragrances was in each case 0, 1 parts by weight based on the specified recipe.
  • the two foams so mixed with fragrances were each compared with a foam (C) to which no fragrance was added at all.
  • the foams were produced according to the following specifications at 22 ° C. and 753 mm Hg air pressure in a wooden box mold with polyethylene film as release agent:
  • polyol CP 3322 (commercially available polyol from DOW)
  • polyol CP 755 (commercially available polyol from DOW)
  • polyol CP 1421 commercially available polyol from DOW
  • Tegoamin® BDE bis (dimethylaminoethyl) ether solution
  • Tegoamin® 33 triethylenediamine solution
  • Tegostab® BF 2470 silicone foam stabilizer
  • TDI 80 tolylene diisocyanate
  • the tin catalyst becomes tin (II) 2-ethylhexanoate, the three polyols, the
  • the finished foam was then kept airtight in odorless plastic bags.
  • For the odor evaluation of the foam cubes of the size 10-10 cm 3 were cut out and transferred into glasses with a volume of 1 L, from which the samples were smelled. The jars were closed with a screw cap. The odor test was carried out after 24 hours of storage of the glasses at 22 ° C.
  • the odor control was rated by a trained panel of 1 1 people. Here two parameters were requested:
  • the additive was able to reduce the intensity of the odor compared to the comparison sample.
  • the smell of the control sample was perceived as more unpleasant.

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Abstract

L'invention concerne des systèmes de polyuréthane peu odorants. L'invention consiste à préparer des systèmes de polyuréthane peu odorants, en particulier de la mousse, grâce à la mise en œuvre d'un additif contenant des substances odorantes lors de la production des systèmes de polyuréthane, au moins 5 % en poids des substances odorantes présentes ayant une valeur ClogP > 4 et un point d'ébullition > 275°C.
PCT/EP2015/063385 2014-07-09 2015-06-16 Systèmes de polyuréthane peu odorants WO2016005149A1 (fr)

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CN114350173A (zh) * 2021-11-25 2022-04-15 天津一汽丰田汽车有限公司 闭孔发泡层、气味遮盖复合层结构的制备方法及应用

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