EP4073218A1 - Wasch- und reinigungsmittel umfassend umweltverträgliche mikrokapseln - Google Patents
Wasch- und reinigungsmittel umfassend umweltverträgliche mikrokapselnInfo
- Publication number
- EP4073218A1 EP4073218A1 EP20820952.8A EP20820952A EP4073218A1 EP 4073218 A1 EP4073218 A1 EP 4073218A1 EP 20820952 A EP20820952 A EP 20820952A EP 4073218 A1 EP4073218 A1 EP 4073218A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- layer
- weight
- shell
- washing
- cleaning agent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
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- 125000000623 heterocyclic group Chemical group 0.000 description 1
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- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- LVECZGHBXXYWBO-UHFFFAOYSA-N pentadecanolide Natural products CC1CCCCCCCCCCCCC(=O)O1 LVECZGHBXXYWBO-UHFFFAOYSA-N 0.000 description 1
- HWGNBUXHKFFFIH-UHFFFAOYSA-I pentasodium;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O HWGNBUXHKFFFIH-UHFFFAOYSA-I 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000001622 pimenta officinalis fruit oil Substances 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000162 poly(ureaurethane) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 108010064470 polyaspartate Proteins 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920003226 polyurethane urea Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- PXGPLTODNUVGFL-JZFBHDEDSA-N prostaglandin F2beta Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H](O)[C@@H]1C\C=C/CCCC(O)=O PXGPLTODNUVGFL-JZFBHDEDSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- NJGBTKGETPDVIK-UHFFFAOYSA-N raspberry ketone Chemical compound CC(=O)CCC1=CC=C(O)C=C1 NJGBTKGETPDVIK-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
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- 239000012088 reference solution Substances 0.000 description 1
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- 239000010666 rose oil Substances 0.000 description 1
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- 239000010668 rosemary oil Substances 0.000 description 1
- 229940058206 rosemary oil Drugs 0.000 description 1
- ZMQAAUBTXCXRIC-UHFFFAOYSA-N safrole Chemical compound C=CCC1=CC=C2OCOC2=C1 ZMQAAUBTXCXRIC-UHFFFAOYSA-N 0.000 description 1
- 239000010670 sage oil Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
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- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- ZFRKQXVRDFCRJG-UHFFFAOYSA-N skatole Chemical compound C1=CC=C2C(C)=CNC2=C1 ZFRKQXVRDFCRJG-UHFFFAOYSA-N 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 239000013042 solid detergent Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019721 spearmint oil Nutrition 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000013097 stability assessment Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 108010038851 tannase Proteins 0.000 description 1
- 229920001864 tannin Polymers 0.000 description 1
- 239000001648 tannin Substances 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010678 thyme oil Substances 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- MBDOYVRWFFCFHM-UHFFFAOYSA-N trans-2-hexenal Natural products CCCC=CC=O MBDOYVRWFFCFHM-UHFFFAOYSA-N 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- DKZBBWMURDFHNE-UHFFFAOYSA-N trans-coniferylaldehyde Natural products COC1=CC(C=CC=O)=CC=C1O DKZBBWMURDFHNE-UHFFFAOYSA-N 0.000 description 1
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 102000003601 transglutaminase Human genes 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
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- 108010083879 xyloglucan endo(1-4)-beta-D-glucanase Proteins 0.000 description 1
- OJYLAHXKWMRDGS-UHFFFAOYSA-N zingerone Chemical compound COC1=CC(CCC(C)=O)=CC=C1O OJYLAHXKWMRDGS-UHFFFAOYSA-N 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
- UZFLPKAIBPNNCA-FPLPWBNLSA-N α-ionone Chemical compound CC(=O)\C=C/C1C(C)=CCCC1(C)C UZFLPKAIBPNNCA-FPLPWBNLSA-N 0.000 description 1
- 229930007850 β-damascenone Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
- C11D3/502—Protected perfumes
- C11D3/505—Protected perfumes encapsulated or adsorbed on a carrier, e.g. zeolite or clay
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/82—Compounds containing silicon
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/02—Inorganic compounds ; Elemental compounds
- C11D3/12—Water-insoluble compounds
- C11D3/1233—Carbonates, e.g. calcite or dolomite
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/30—Amines; Substituted amines ; Quaternized amines
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3753—Polyvinylalcohol; Ethers or esters thereof
Definitions
- the invention relates to washing and cleaning agents comprising stable microcapsules with environmentally compatible wall materials.
- Microencapsulation is a versatile technology. It offers solutions for numerous innovations - from the paper industry to household products, microencapsulation increases the functionality of a wide variety of active substances. Encapsulated active ingredients can be used more economically and improve the sustainability and environmental compatibility of many products.
- the polymeric wall materials of the microcapsules themselves are environmentally friendly to very different degrees.
- microcapsule walls based on the natural product gelatin and thus completely biodegradable have long been used.
- a method for gelatin encapsulation that was developed as early as the 1950s is disclosed in US Pat. No. 2,800,457. Since then, a large number of variations in terms of materials and process steps have been described.
- biodegradable or enzymatically degradable microcapsule walls are used in order to use enzymatic degradation as a method for releasing the core material.
- Such microcapsules are described, for example, in WO 2009/126742 A1 or WO 2015/014628 A1.
- microcapsules are not suitable for many industrial applications and household products. Because natural product-based microcapsules do not meet the diffusion tightness, chemical resistance and temperature resistance required for detergents and cleaning agents, adhesive systems, paints and dispersions, and also the required loading with core material.
- Classically organic polymers such as melamine-formaldehyde polymers (see e.g. EP 2 689 835 A1, WO 2018/114056 A1, WO 2014/016395 A1, WO 2011/075425 A1 or WO 2011/120772 A1); Polyacrylates (see e.g. WO 2014/032920 A1, WO 2010/79466 A2); Polyamides; Polyurethane or polyureas (see e.g.
- WO 2014/036082 A2 or WO 2017/143174 A1 are used.
- the capsules made of such organic polymers have the required diffusion tightness, stability and chemical resistance.
- these organic polymers are only enzymatically or biodegradable to a very small extent.
- WO 2014/044840 A1 describes a method for producing two-layer microcapsules with an inner polyurea layer and an outer gelatin-containing layer.
- the polyurea Layer produced by polyaddition on the inside of the gelatin layer obtained by coacervation.
- the capsules obtained in this way have, according to the description, due to the polyurea layer, the necessary stability and impermeability for use in detergents and cleaning agents and, due to the gelatin, are also sticky in order to adhere them to surfaces. Specific stabilities and resistances are not mentioned.
- a disadvantage of polyurea capsules is the inevitable side reaction of the core materials with the diisocyanates used to produce the urea, which have to be added to the oil-based core.
- WO 2010/003762 A1 describes particles with a core-shell-shell structure.
- the core of each particle is a poorly water-soluble or water-insoluble organic active ingredient.
- the shell directly enveloping the core contains a biodegradable polymer and the outer shell contains at least one metal or semi-metal oxide. With this structure, a biodegradable shell is obtained.
- the microcapsules are nevertheless used according to WO 2010/003762 A1 in foods, cosmetics or pharmaceutical agents, but cannot be used for the high-requirement areas according to the invention because of their lack of tightness.
- the present invention is based, inter alia, on the discovery that by means of a multi-layer structure of the shells, microcapsules can be produced which are essentially biodegradable and yet have sufficient stability and tightness to be used in detergents and cleaning agents.
- a first stability and structure-imparting layer makes up the main part of the capsule shell, which consists of naturally occurring and readily biodegradable materials, such as gelatine or alginate, or materials ubiquitous in nature.
- This first layer is combined with a second layer which provides airtightness and which can consist of known materials used for microencapsulation, such as melamine-formaldehyde or meth (acrylate).
- the second layer can be arranged both on the outside of the first layer and on the inside of the first layer.
- the second layer is preferably arranged on the inside of the first layer.
- the inventors have succeeded in designing the second layer, which provides airtightness, with a hitherto unimaginable low wall thickness and nevertheless ensuring sufficient impermeability, as shown in Example 5.
- the proportion of the total wall is thus kept very low, so that the microcapsule wall has a biodegradability, measured according to OECD 301 F, of at least 40%, as shown in Examples 6 and 7.
- the invention relates to washing and cleaning agents comprising: a) Microcapsules comprising a core material, wherein the core material comprises at least one fragrance, and a shell, wherein the shell consists of at least a first and a second layer, the chemical compositions of which are different, and wherein the shell has a biodegradability measured according to OECD 301 F of has at least 40%; and, optionally, b) at least one further component selected from surfactants, builders, enzymes and absorption-enhancing agents.
- the invention relates to the use of detergents and cleaning agents according to the first aspect in a method for conditioning textiles or for cleaning textiles and / or hard surfaces.
- FIG. 1 shows a light microscope image of the capsules MK 1 used according to the invention in a 50-fold and a 500-fold magnification, taken with an Olympus 5 BX 50 microscope.
- FIG. 2 shows a light microscope image of the reference microcapsule MK 2 (melamine-formaldehyde) in a 50-fold and a 500-fold magnification taken with an Olympus BX 50 microscope.
- FIG 3 shows a light microscope image of the reference microcapsule MK 3 (gelatin alginate) in a 50-fold and a 500-fold magnification, taken with an Olympus BX 50 microscope.
- FIG. 4 shows a diagram of the course of the biological degradation of the microcapsule MK 1 used according to the invention over 28 days (shown as a solid line)
- (a) shows the result according to OECD301 F.
- the breakdown of ethylene glycol is shown in the form of a dashed line
- ( b) shows the result according to OECD302C.
- the degradation of aniline is shown in the form of a dashed line.
- FIG. 5 shows a comparison of the course of the biological degradation over 28 days of the microcapsule MK 1 used according to the invention, the MF reference microcapsule MK 2 and the gelatin / alginate reference microcapsule MK 3.
- a measurement according to OECD301 F for the first 10 is shown Biodegradation Days.
- the time window is shown in which the microcapsule MK 1 according to the invention reaches a degree of degradation of 60%.
- FIG. 6 shows a light microscope image of the capsules MK 4 according to the invention in a 50-fold and a 500-fold magnification, taken with an Olympus BX 50 microscope.
- 7 shows a diagram of the course of the biological degradation according to OECD 301 F over 60 days after washing the microcapsule MK 1 according to the invention over time and the MF reference microcapsule MK 2 and the gelatin / alginate reference microcapsule MK 3.
- OECD 301 F shows a diagram of the course of the biological degradation according to OECD 301 F over 60 days after washing the microcapsule MK 1 according to the invention over time and the MF reference microcapsule MK 2 and the gelatin / alginate reference microcapsule MK 3.
- As a positive control both the degradation of ethylene glycol shown in the form of a dashed line, and the degradation of walnut shell flour in the form of a dotted line.
- Biodegradability describes the ability of organic chemicals to be decomposed biologically, i.e. by living beings or their enzymes. In the ideal case, this chemical metabolism runs completely up to mineralization, but can also remain with stable transformation products.
- the guidelines for the testing of chemicals of the OECD, which are also used in connection with the approval of chemicals, are generally recognized.
- the tests of the OECD test series 301 (A-F) demonstrate rapid and complete biodegradation under aerobic conditions. Different test methods are available for readily or poorly soluble as well as for volatile substances.
- the manometric respiration test (OECD 301 F) is used in the registration.
- the fundamental biodegradability inherent biodegradability
- OECD 302 C the measurement standard OECD 302 C.
- Biodegradable or “biodegradable” within the meaning of the present invention are microcapsule walls that have a biodegradability measured according to OECD 301 F of at least 40% or measured according to OECD 302 C (MITI-II test) of at least 20% and thus an inherent one or show fundamental degradability. This corresponds to the limit value for OECD 302 C according to "Revised Introduction to the OECD Guidlines for Testing of Chemicals, Section 3, Part 1, dated 23 March 2006". From a limit value of at least 60%, measured according to OECD 301 F, microcapsule walls are also referred to as rapidly biodegradable.
- Impermeability to a substance, gas, liquid, radiation or the like is a property of material structures.
- the terms “tightness” and “tightness” are used synonymously according to the invention. Leak tightness is a relative term and always refers to given framework conditions.
- (meth) acrylate denotes both methacrylates and acrylates.
- microcapsules is understood to mean particles which contain an inner space or core which is filled with a solid, gelled, liquid or gaseous medium and is enclosed (encapsulated) by a continuous shell (shell) made of film-forming polymers. These particles are preferably small in size.
- microcapsules core-shell capsules or simply “capsules” are used synonymously.
- Microencapsulation is a manufacturing process in which small and very small portions of solid, liquid or gaseous substances are surrounded by a shell made of polymeric or inorganic wall materials. The microcapsules obtained in this way can have a diameter of a few millimeters to less than 1 ⁇ m.
- the microcapsule according to the invention thus has a multilayer shell.
- the shell that surrounds the core material of the microcapsule is also regularly referred to as the “wall” or “shell”.
- microcapsules according to the invention with a multi-layer shell can also be referred to as multi-shell microcapsules or multi-shell microcapsule system, since the individual layers can also be viewed as individual shells. “Multi-layered” and “multi-layered” are therefore used synonymously.
- “Wall formers” are the components that build the microcapsule wall.
- microcapsules which are used in the detergents and cleaning agents according to a first aspect of the invention comprise a core material and a shell, the shell consisting of at least a first and a second layer, the chemical compositions of which differ and the shell being biodegradable measured according to OECD 301 F of at least 40%. Measured according to OECD 302 C, the microcapsules according to the invention have a biodegradability of at least 20%.
- microcapsule shells are biodegradable according to OECD due to the high proportion of natural components.
- the first layer of the microcapsules contains one or more biodegradable components as wall formers.
- This first layer forms the main component of the microcapsule shell that provides stability and thus guarantees the high biodegradability according to OECD 301 F of at least 40%.
- Biodegradable components suitable as wall formers for the first layer are proteins such as gelatin; Polysaccharides such as alginate, gum arabic, chitin, or starch; phenolic macromolecules such as lignin; Polyglucosamines such as chitosan, polyvinyl esters such as polyvinyl acetate and polyvinyl alcohols, in particular highly hydrolyzed and fully hydrolyzed polyvinyl alcohols; Phosphazenes and polyesters such as polylactide or polyhydroxyalkanoate.
- proteins such as gelatin
- Polysaccharides such as alginate, gum arabic, chitin, or starch
- phenolic macromolecules such as lignin
- Polyglucosamines such as chitosan
- polyvinyl esters such as polyvinyl acetate and polyvinyl alcohols, in particular highly hydrolyzed and fully hydrolyzed polyvinyl alcohols
- Phosphazenes and polyesters
- biodegradable components can be selected appropriately for the respective application in order to form a stable multi-layer shell with the material of the second layer.
- the second layer can be arranged both on the outside of the first layer and on the inside of the first layer.
- the second layer is preferably arranged on the inside of the first layer.
- the biodegradable components can be selected, for example - if arranged on the inside - to ensure compatibility with the core material or - if arranged on the outside - to achieve compatibility with the chemical conditions of the area of application.
- the biodegradable components can be combined as desired in order to influence the biodegradability or, for example, the stability and chemical resistance of the microcapsule.
- the shell of the microcapsules has a biodegradability of 50% according to OECD 301F. In a further embodiment, the shell of the microcapsule has a biodegradability of at least 60% (OECD 301 F). In a further embodiment, the biodegradability is at least 70% (OECD 301 F). According to OECD 5 302 C, the microcapsule according to the invention can have a biodegradability of at least 25%. According to one embodiment, the biodegradability is at least 30% (OECD 302 C). According to a further embodiment, the biodegradability is at least 40% (OECD 302 C). The biodegradability is measured over a period of 28 days.
- the biodegradability is measured over a period of 60 days (see Opinion on an Annex XV dossier proposing restrictions on intentionally-added microplastics of June 11, 2020 ECHA / RAC / RES-0-0000006790- 71-01 / F).
- the microcapsules are preferably freed from dissolved residues by washing before the biodegradability is determined.
- the capsule dispersion is washed after preparation by centrifuging and redispersing three times in water. To do this, the sample is centrifuged. After the clear supernatant has been filtered off with suction, it is made up with water and the sediment is redispersed by shaking.
- biodegradability such as the rapidly degradable ethylene glycol or nature-based walnut shell flour with the typical gradual degradation of a complex mixture of substances.
- the microcapsule according to the invention shows a similar, preferably better biodegradability over a period of 28 or 60 days than the walnut shell flour.
- a high biodegradability value according to the invention is achieved on the one hand by the wall formers used, but on the other hand by the structure of the shell according to the invention. Because the use of a certain percentage of natural, potentially biodegradable components does not automatically lead to a corresponding biodegradability value. This depends on how the potentially biodegradable components are present in the shell.
- the first layer contains gelatin.
- the first layer contains alginate.
- the first layer contains gelatin and alginate.
- both gelatin and alginate are suitable for the production of microcapsules according to the invention with high biodegradability and high stability. Further suitable combinations of natural components in the first layer are gelatin and gum arabic.
- the first layer contains one or more curing agents.
- Curing agents according to the invention are aldehydes, such as, for example, glutaraldehyde, glyoxal and formaldehyde, as well as tannins, enzymes such as transglutaminase and organic anhydrides such as maleic anhydride.
- the curing agent glutaraldehyde is preferred because of its very good crosslinking properties.
- the curing agent glyoxal is also preferred because of its good crosslinking properties and, compared to glutaraldehyde, its lower toxicological classification.
- the use of curing agents makes the first layer, which consists of natural murals, more impervious.
- the curing agents reduce the stickiness of the layer and thus the tendency to agglomeration.
- curing agents lead to a reduced biodegradability of the natural polymers. Due to the combination of the first layer with the second layer as a diffusion barrier, the amount of curing agent in the first layer can be kept low, which in turn contributes to the easy biodegradability of the layer. According to one embodiment, the proportion of the curing agent in the first layer is below 25% by weight.
- the proportions of the components of the layers relate to the total weight of the layer, i.e. the total dry weight of the components used for production, without taking into account the components used in production that are not or only slightly incorporated into the layer, such as surfactants and protective colloids. Above this value, the biodegradability according to the invention according to OECD 301 F cannot be guaranteed.
- the proportion of the hardening agent in the first layer is preferably in the range of 5-15% by weight. This proportion leads to effective crosslinking of the gelatin and, in a quantitative reaction, leads to the formation of as little residual monomer as possible.
- the range 9% by weight to 12% by weight is particularly preferred; it ensures the required degree of crosslinking and a stable covering of the second shell in order to buffer the otherwise sensitive diffusion barrier and to equip it with further barrier properties and has only a small amount of residual aldehyde in a downstream alkaline setting, the slurry is broken down via an aldol reaction.
- the first layer contains gelatin and glutaraldehyde. According to a further embodiment, the first layer contains gelatin, alginate and glutaraldehyde. In an additional embodiment, the first layer contains gelatin and glyoxal. According to Weiner's other embodiment, the first layer contains gelatine, alginate and glyoxal.
- the exact chemical composition of the first layer is not critical. It only has to ensure sufficient stability of the microcapsule wall and the release behavior required for the respective application. It is essential that they only contain small amounts or preferably no unnatural persistent ones Has components. Consequently, as an alternative to or in addition to the biodegradable components, the first layer can also contain one or more inorganic components as wall formers.
- Inorganic components as wall formers can in particular be calcium carbonates or polysilicates. These are particularly suitable because they are ubiquitous components that are environmentally friendly. Since there is no need to break down these inorganic components, they are regarded according to the invention as completely biodegradable, even if the criteria according to OECD 301 or OECD 302 are not applicable to these components.
- the second layer is also referred to as a layer which provides a seal or a diffusion barrier.
- the second layer has an average thickness in the range from 0.01 ⁇ m to 1 ⁇ m. A layer thickness greater than 1 ⁇ m would increase the proportion of the components of the second layer on the overall capsule wall too much and thus no longer ensure sufficient biodegradability. With a layer thickness of less than 0.01 ⁇ m, the second layer would no longer be a sufficient diffusion barrier. The microcapsules would therefore be unsuitable for high-demand areas.
- the second layer has sufficient tightness for most areas of application.
- the wall thickness of the second layer should be at most 0.5 ⁇ m.
- the wall thickness of the second layer is particularly preferably in the range from 0.05 ⁇ m to 0.30 ⁇ m. In this area an optimal density with easy biodegradability is achieved.
- the second layer preferably contains, as a wall former, one or more components selected from the group consisting of an aldehyde component, an aromatic alcohol, an amine component, and an acrylate component. Manufacturing processes for producing microcapsules with these wall materials are known to the person skilled in the art. A polymer selected from a polycondensation product of an aldehyde component with one or more aromatic alcohols and / or amine components can be used to produce the second layer.
- the thin wall thickness of the second layer according to the invention can be achieved in particular with a melamine-formaldehyde layer containing aromatic alcohols or m-aminophenol.
- the second layer preferably comprises an aldehyde component, an amine component and an aromatic alcohol.
- amine-aldehyde compounds in the second layer in particular melamine-formaldehyde, has the advantage that these compounds form a hydrophilic surface with a high proportion of hydroxyl functionality, which is excellent compatibility with the hydrogen-bonded components of the first layer such as biodegradable proteins, polysaccharides, chitosan, lignins and phosphazenes but also inorganic wall materials such as CaCO 3 and polysiloxanes.
- polyacrylates in particular from the Components styrene, vinyl compounds, methyl methacrylate, and 1,4-butanediol acrylate, methacrylic acid, by initiation e.g.
- t-butyl hydroperoxide in a radical-induced polymerization are produced as a microcapsule wall, which form a hydrophilic surface with a high proportion of hydroxyl functionality, which are therefore just as compatible with the components of the first layer according to the invention.
- a wall former of the second layer is thus an aldehydic component.
- the aldehyde component of the second layer is selected from the group consisting of formaldehyde, glutaraldehyde, succinaldehyde, furfural and glyoxal. Microcapsules have already been successfully produced with these aldehydes (see WO 2013 037 575 A1), so that it can be assumed that similarly dense capsules as with formaldehyde are obtained.
- the proportion of the aldehyde component for wall formation based on the total weight of the second shell should be in the range from 5 to 50% by weight. It is assumed that outside these limits, a sufficiently stable and dense thin layer cannot be obtained.
- the concentration of the aldehyde component in the second layer is preferably in the range from 10 to 30% by weight.
- the concentration of the aldehyde component in the second layer is particularly preferably in the range from 15 to 20% by weight.
- Particularly suitable amine components in the second layer are melamine, melamine derivatives and urea or combinations thereof.
- Suitable melamine derivatives are etherified melamine derivatives and methylolated melamine derivatives. Melamine in the methylolated form is preferred.
- the amine components can be used, for example, in the form of alkylated mono- and polymethylol urea precondensation products or partially methylolated mono- and polymethylol-1,3,5-triamono-2,4,6-triazine precondensation products such as Luracoll SD® (from BASF) become.
- the amine component is melamine.
- the amine component is a combination of melamine and urea.
- the aldehyde component and the amine component can be present in a molar ratio in the range from 1: 5 to 3: 1.
- the molar ratio can be 1: 5, 1: 4.5, 1: 4, 1: 3.5, 1: 3, 1: 2.5, 1: 2, 1: 1, 8, 1: 1, 6, 1: 1, 4, 1; 1, 3, 1: 1, 2, 1: 1, 1, 5: 1, 2: 1, 2.5: 1, or 3: 1.
- the molar ratio is preferably in the range from 1: 3 to 2: 1.
- the molar ratio of the aldehydic component and the amine component can particularly preferably be in the range from 1: 2 to 1: 1.
- the aldehydic component and the amine component are generally used in a ratio of about 1: 1.3.
- aldehyde-amine capsule walls with a molar ratio of 1: 2 are also known. These capsules have the advantage that the proportion of highly crosslinking aldehyde, in particular formaldehyde, is very low. However, these capsules have a lower tightness than the Capsules with a ratio of 1: 1, 3. Capsules with a ratio of 2: 1 have an increased tightness, but have the disadvantage that the aldehyde component is partially unreacted in the capsule wall and the slurry.
- the proportion of amine components (for example melamine and / or urea) in the second layer, based on the total weight of the second layer is in the range from 20% by weight to 85% by weight.
- the proportion of the amine component can be 20% by weight, 25% by weight, 30% by weight, 35% by weight, 40% by weight, 45% by weight, 50% by weight, 55% by weight %
- 60% by weight, 65% by weight, 70% by weight, 75% by weight, 80% by weight or 85% by weight are.
- the proportion of the amine component in the second layer, based on the total weight of the second layer is in the range from 40% by weight to 80% by weight.
- the proportion of the amine component is particularly preferably in the range from 55% by weight to 70% by weight.
- the aromatic alcohol it is possible to greatly reduce the wall thickness of the second layer made up of the amine component and the aldehyde component in order to still obtain a layer that has the necessary impermeability and is stable enough, at least in combination with the first layer .
- the aromatic alcohols give the wall an increased tightness, since their strongly hydrophobic aromatic structure makes it difficult for low-molecular substances to diffuse through.
- phloroglucinol, resorcinol or m-aminophenol are particularly suitable as aromatic alcohol.
- the aromatic alcohol is selected from the group consisting of phloroglucinol, resorcinol and aminophenol.
- the aromatic alcohol is used in a molar ratio to the aldehyde component in the range (alcohol: aldehyde) 1: 1 to 1:20, preferably in the range 1: 2 to 1:10.
- the proportion of aromatic alcohol in the second layer is in the range from 1.0% by weight to 20% by weight.
- the proportion of the aromatic alcohol can be 1.5% by weight, 2.0% by weight, 2.5% by weight, 3.0% by weight, 4.0% by weight, 5.0 % By weight, 6% by weight, 7% by weight, 8% by weight, 9% by weight, 10% by weight, 11% by weight, 12% by weight, 13% by weight %, 14% by weight, 15% by weight, 16% by weight, 17% by weight, 18% by weight, 19% by weight or 20% by weight are. Due to their aromatic structure, the aromatic alcohols give the capsule wall a color that increases with the proportion of aromatic alcohol.
- the aromatic alcohols are prone to oxidation, which is currently leading to a change in color.
- the undesired coloration of the microcapsules can hardly be balanced out with a dye.
- the aromatic alcohols should therefore not be used above 20.0% by weight. Below 1.0% by weight, no effect on the tightness can be detected.
- the proportion of aromatic alcohol in the second layer is in the range from 5.0 to 15.0% by weight. The coloration is tolerable in most applications up to a percentage of 15.0% by weight.
- the proportion of the aromatic alcohol in the second layer is in the range from 9.0% by weight to 13.0% by weight.
- the aldehyde component of the second layer can be used together with an aromatic alcohol such as resorcinol, phloroglucinol or m-aminophenol as wall-forming component (s), i.e. without the amine component (s).
- an aromatic alcohol such as resorcinol, phloroglucinol or m-aminophenol as wall-forming component (s), i.e. without the amine component (s).
- the second layer of the microcapsules contains melamine, formaldehyde and resorcinol. In one embodiment, the second layer of the microcapsules contains melamine, urea, formaldehyde and resorcinol. In a preferred embodiment, the second layer of the microcapsules contains melamine in the range from 25 to 40% by weight, formaldehyde in the range from 15 to 20% by weight and resorcinol in the range from 0.1 to 12% by weight and optionally Urea in the range from 15 to 20% by weight. The proportions relate to the amounts used to form the wall of the layer and are based on the total weight of the second layer without protective colloid.
- a protective colloid can also be used to produce the second layer from an aldehyde component, an amine component and an aromatic alcohol.
- a suitable protective colloid is 2-acrylamido-2-methyl-propanesulfonic acid (AMPS, commercially available as Lupasol®PA 140, BASF) or its salts.
- the proportion of the protective colloid in the components used to produce the second layer can be in the range from 10 to 30% by weight based on the total dry weight of the constituents used. According to one embodiment, the proportion of the protective colloid in the components used to produce the second layer is in the range from 15 to 25% by weight.
- a certain low percentage of the protective colloid can also be contained in the finished microcapsule shell. It is technically difficult to determine the proportion of protective colloid in the second layer. In addition, the proportion is only small. Consequently, the other proportions of the other constituents are represented as if the protective colloid were not included.
- the (meth) acrylate polymers optionally used to form the thin second layer (diffusion barrier) can be homopolymers or copolymers of methacrylate monomers and / or acrylate monomers.
- the (meth) acrylate polymers are, for example, homopolymers or copolymers, preferably copolymers, one or more polar functionalized (meth) acrylate monomers, such as sulfonic acid group-containing, carboxylic acid group-containing, phosphoric acid group-containing, nitrile group-containing, phosphonic acid-containing, (meth) acrylate monomers containing ammonium groups, amine groups or nitrate groups.
- the polar groups can also be present in salt form.
- (Meth) acrylate copolymers can consist, for example, of two or more (meth) acrylate monomers (e.g. acrylate + 2-acrylamido-2-methyl-propanesulfonic acid) or of one or more (meth) acrylate monomers and one or more of ( Meth) acrylate monomers different monomers (e.g. methacrylate + styrene).
- (meth) acrylate polymers are homopolymers of (meth) acrylates containing sulfonic acid groups (e.g.
- AMPS 2-acrylamido-2-methyl-propanesulfonic acid or its salts
- copolymers copolymers of acrylamide and (meth) acrylic acid
- Copolymers of alkyl (meth) acrylates and N-vinylpyrrolidone commercially available as Luviskol® K15, K30 or K90, BASF
- copolymers of (meth) acrylates with polycarboxylates or polystyrene sulfonates copolymers of (meth) acrylates with vinyl ethers and / or maleic anhydride
- copolymers of (meth) acrylates with isobutylene and / or maleic anhydride copolymers of (meth) acrylates with styrene-maleic anhydride.
- Preferred (meth) acrylate polymers are homo- or copolymers, preferably copolymers, of 2-acrylamido-2-methyl-propanesulfonic acid or its salts (AMPS). Copolymers of
- 2-acrylamido-2-methyl-propanesulfonic acid or its salts for example copolymers with one or more comonomers from the group of (meth) acrylates, vinyl compounds such as vinyl esters or styrenes, unsaturated di- or polycarboxylic acids such as maleic acid esters, or salts of amyl compounds or allyl compounds.
- the microcapsules according to the invention have a high level of impermeability.
- the microcapsules have a tightness which ensures an escape of at most 80% by weight of the core material used after storage for a period of 12 weeks at a temperature of 0 to 40.degree.
- the tightness also depends on the type of core material.
- the tightness of the microcapsules according to the invention was determined according to the invention for the Weiroclean scented oil from Kitzing, since this scented oil is representative of microencapsulated scented oils in terms of its chemical properties.
- Weiroclean has the following components (with proportion based on the total weight):
- At least one fragrance is used as the core material. It is particularly preferred that these are fragrant or perfume oils optimized for microencapsulation for the detergent and cleaning agent sector, such as, for example, the Weiroclean fragrance formulation (Kurt Kitzing GmbH).
- the fragrances can be used in the form of a solid or liquid formulation, but especially in liquid form.
- Fragrances that can be used as the core material are not subject to any particular restrictions.
- Individual fragrance compounds of natural or synthetic origin e.g. of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type, can be used.
- Perfume compounds of the ester type are, for example, benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate, dimethylbenzylcarbinylacetate (DMBCA), phenylethyl acetate, benzyl acetate, ethylmethylphenylglycinate, allylcyclohexylglycinate, allylcyclohexylpropionate, allylcyclohexylpropionate, allylcyclohexylpropionate, allylcyclohexylpropionate, allylcyclohexylpropionate,
- the ethers include, for example, benzyl ethyl ether and ambroxan
- the aldehydes include the abovementioned, for example, the linear alkanals with 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamenaldehyde (3- (4-propan-2-ylphenyl) butanal), lilial and bourgeonal
- the ketones for example, the ionones, [alpha] -lsomethylionone and methyl cedryl ketone
- the alcohols anethole, citronellol, eugenol, geraniol, linalool, phenylethyl alcohol and terpineol
- the hydrocarbons mainly include terpenes such as limonene and pinene.
- Suitable fragrance aldehydes can be selected from adoxal (2,6,10-trimethyl-9-undecenal), anisaldehyde (4-methoxybenzaldehyde), cymal or cyclamenaldehyde (3- (4-isopropylphenyl) -2-methylpropanal), nympheal (3- ( 4-isobutyl-2-methylphenyl) propanal), ethylvanillin, florhydral (3- (3- isopropylphenyl) butanal]), trifernal (3-phenylbutyraldehyde), helional (3- (3,4-methylenedioxyphenyl) -2-methylpropanal), Heliotropin, hydroxycitronellal, lauraldehyde, lyral (3- and 4- (4-hydroxy-4-methylpentyl) -3-cyclohexene-1-carboxaldehyde), methylnonylacetaldehyde, l
- Suitable fragrance ketones include, but are not limited to, methyl beta-naphthyl ketone, musk indanone (1, 2,3,5,6,7-hexahydro-1, 1, 2,3,3-pentamethyl-4H-indene-4- on), Calone
- the core materials can also contain natural fragrance mixtures, such as those obtainable from vegetable sources, e.g. pine, citrus, jasmine, patchouly, rose or ylang-ylang oil. Also suitable are muscatel sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, linden blossom oil, juniper oil, vetiver oil, olibanum oil, galbanum oil and labdanum oil as well as orange blossom oil, neroli oil, orange peel oil and sandalwood oil.
- natural fragrance mixtures such as those obtainable from vegetable sources, e.g. pine, citrus, jasmine, patchouly, rose or ylang-ylang oil.
- muscatel sage oil chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, linden blossom oil, juniper oil, vetiver oil, olibanum oil, galbanum oil and labdanum oil as well as orange blossom oil, neroli oil, orange peel oil and sandal
- fragrances that can be contained in the agents according to the invention within the scope of the present invention are, for example, the essential oils such as angelica root oil, anise oil, arnica flower oil, basil oil, bay oil, champaca flower oil, noble fir oil, noble fir cone oil, elemi oil, eucalyptus oil, fennel oil, spruce needle oil, galbanum oil, Geranium oil, ginger grass oil, guaiac wood oil, gurjun balsam oil, helichrysum oil, ho oil, ginger oil, iris oil, kajeput oil, calamus oil, chamomile oil, camphor oil, kanaga oil, cardamom oil, cassia oil, pine needle oil, copaiva oil balsam oil, coriander oil, cumin oil, lavender oil, lime oil, spearmint oil Mandarin oil, lemon balm oil, musk seed oil, myrrh oil, clove oil, neroli oil, niaouli oil, oli
- ethyl-n-nonyl ketone muskon, ß-naphthol ethyl ether, ß-naphthol methyl ether, nerol, n-nonyl aldehyde, nonyl alcohol, n-octyl aldehyde, p-oxy acetophenone, pentadecanolide, ß-phenylethyl alcohol, phenylacetic acid, pulegon, safrol, Salicylic acid isoamyl ester, salicylic acid methyl ester, salicylic acid hexyl ester,
- Salicylic acid cyclohexyl ester Santalol, Sandelice, Skatol, Terpineol, Thymen, Thymol, Troenan, y- Undelactone, vanillin, veratrumaldehyde, cinnamaldehyde, cinnamic alcohol, cinnamic acid, ethyl cinnamate, benzyl cinnamate, diphenyloxide, limonene, linalool, linalyl acetate and propionate, melusate, menthol, menthone, methyl-n-heptenon, methyl-n-heptenon from it.
- the tightness of the capsule wall can be influenced by the choice of shell components.
- the microcapsules have a tightness that allows an exit of at most 75% by weight, at most 70% by weight, at most 65% by weight, at most 60% by weight, at most 55% by weight, at most 50% by weight % By weight, at most 45% by weight, at most 40% by weight of the core material used when stored for a period of 12 weeks at a temperature of 0 to 40 ° C.
- the microcapsules are stored in a model formulation that corresponds to the target application.
- the microcapsules are also storage-stable in the product in which they are used. For example in detergents, cleaning agents, dishwashing detergents and fabric softeners as well as textile care products. The standard formulations of these products are known to the person skilled in the art.
- the pH in the vicinity of the microcapsules during storage is in the range from 2 to 11.
- the second layer can be arranged on the inside or the outside of the first layer. According to one embodiment, the second layer is arranged on the inside of the first layer.
- Such an arrangement has the advantage that the layer imparting impermeability can additionally serve as a chemical protective layer between the biodegradable first layer and the core material. This is especially important in cases in which the core material can chemically attack the biodegradable material of the first layer.
- the problem with this structure is that the very thin second layer must first be formed as a template during the encapsulation. In the present case, this was solved by selecting the appropriate murals and additives.
- An advantage of the template strategy i.e.
- the production of the capsule starting with the construction of the very thin second layer as a template is that in this production the components used as wall formers can be placed in the continuous water phase, which means that there is minimal contact with the core material during construction the shell is given.
- the components of the additional first layer can then be deposited as the first layer without interaction with the core material.
- microcapsule shells according to the invention have at least two layers, i.e. they can be, for example, two-layer, three-layer, four-layer, or five-layer.
- the microcapsules are preferably two- or three-layered.
- the microcapsule has a third layer which is arranged on the outside of the first layer.
- the third layer is arranged on the outside of the second layer.
- the second layer is preferably on the outside of the first layer.
- This third layer can be used to adapt the surface properties of the microcapsule for a specific application. To call this would be the improvement of the adhesion of the microcapsules to a wide variety of surfaces and a reduction in agglomeration.
- the third layer also binds residual amounts of aldehyde, thus reducing the content of free aldehydes in the capsule dispersion. Furthermore, it can provide additional (mechanical) stability or further increase the tightness.
- the third layer can contain a component selected from amines, organic salts, inorganic salts, alcohols, ethers, polyphosphazenes, and noble metals.
- Precious metals increase the tightness of the capsules and can give the microcapsule surface additional catalytic properties or the antibacterial effect of a silver layer.
- Organic salts especially ammonium salts, lead to a cationization of the microcapsule surface, which means that it adheres better to textiles, for example.
- alcohols When incorporated via free hydroxyl groups, alcohols also lead to the formation of hydrogen bonds, which likewise allow better adhesion to substrates.
- An additional polyphosphazene layer or coating with inorganic salts, e.g. silicates leads to an additional increase in impermeability without affecting biodegradability.
- the third layer contains activated melamine. On the one hand, the melamine catches any free aldehyde components of the second layer, increases the tightness and stability of the capsule and can also influence the surface properties of the microcapsules and thus the adhesion and agglomeration behavior.
- the proportion of the second layer in the shell is at most 30%.
- the proportion is at most 25% by weight based on the total weight of the shell.
- the proportion of the second layer is particularly preferably at most 20% by weight.
- the proportion of the first layer in the shell based on the total weight of the shell is at least 40% by weight, preferably at least 50% by weight, particularly preferably at least 60% by weight.
- the proportion of the third layer in the shell based on the total weight of the shell is at most 25%, preferably at most 20% by weight, particularly preferably at most 15% by weight.
- the size of the microcapsules according to the invention is in the range customary for microcapsules.
- the diameter can be in the range from 100 nm to 1 mm. The diameter depends on the exact capsule composition and the manufacturing process.
- the peak maximum of the particle size distribution is regularly used as the characteristic value for the size of the capsules.
- the peak maximum of the particle size distribution is preferably in the range from 1 ⁇ m to 500 ⁇ m.
- the peak maximum of the particle size distribution can be, for example, 1 pm, 2 pm, 3 pm, 4 pm, 5 pm, 10 pm, 15 pm, 20 pm, 30 pm, 40 pm, 50 pm, 60 pm, 70 pm, 80 pm , 90 pm, 100 pm, 120 pm, 140 pm, 160 pm, 180 pm 200 pm, 250 pm, 300 pm 350 pm, 400 pm, 450 pm or 500 pm.
- the microcapsules have a peak maximum of the particle size distribution of 10 ⁇ m to 100 ⁇ m. In particular, the peak maximum of the particle size distribution is in the range from 10 pm to 50 pm. Washing or cleaning agents containing microcapsules
- this biodegradable capsule Due to the robustness or tightness of this biodegradable capsule, it can be used advantageously in a washing and cleaning agent, these agents including fabric softeners, textile care agents, solid detergents, for example granules or powders, liquid detergents, household cleaners, bathroom cleaners, hand dishwashing detergents and machine dishwashing detergents.
- these agents including fabric softeners, textile care agents, solid detergents, for example granules or powders, liquid detergents, household cleaners, bathroom cleaners, hand dishwashing detergents and machine dishwashing detergents.
- the washing or cleaning agents of the invention preferably comprise at least one ingredient selected from the group of surfactants, enzymes, builders and absorption-enhancing agents.
- the washing and cleaning agents can also contain anionic, nonionic, cationic, amphoteric or zwitterionic surfactants or mixtures thereof. Furthermore, these agents can be in solid or liquid form.
- the surfactants include in particular at least one anionic surfactant and / or at least one nonionic surfactant.
- Suitable nonionic surfactants are in particular ethoxylation and / or propoxylation products of alkyl glycosides and / or linear or branched alcohols each with 12 to 18 carbon atoms in the alkyl part and 3 to 20, preferably 4 to 10, alkyl ether groups.
- Suitable anionic surfactants are in particular soaps and those which contain sulfate or sulfonate groups with preferably alkali ions as cations.
- Soaps that can be used are preferably the alkali salts of saturated or unsaturated fatty acids having 12 to 18 carbon atoms. Such fatty acids can also be used in a form that is not completely neutralized.
- the sulfate-type surfactants which can be used include the salts of the sulfuric acid half-esters of fatty alcohols with 12 to 18 carbon atoms and the sulfation products of the nonionic surfactants mentioned with a low degree of ethoxylation.
- the sulfonate-type surfactants that can be used include linear alkylbenzenesulfonates with 9 to 14 carbon atoms in the alkyl part, alkanesulfonates with 12 to 18 carbon atoms, and olefin sulfonates with 12 to 18 carbon atoms, which are formed when corresponding monoolefins are reacted with sulfur trioxide, and alpha-sulfo fatty acid esters, which are formed during the sulfonation of fatty acid methyl or ethyl esters.
- Cationic surfactants are preferably selected from the esterquats and / or the quaternary ammonium compounds (QAV) according to the general formula (R I ) (R ") (R III ) (R IV ) N + X-, in which R 'to R IV for the same or different Ci-22-alkyl, C7 28 arylalkyl radicals, or heterocyclic radicals, two or-in the case of an aromatic compound, such as pyridine-even together with the nitrogen atom forming the heterocycle, for example a pyridinium or imidazolinium form three radicals, and X ⁇ stands for halide ions, sulfate ions, hydroxide ions or similar anions.
- QAV quaternary ammonium compounds
- QAV can be produced by reacting tertiary amines with alkylating agents such as methyl chloride, benzyl chloride, dimethyl sulfate, dodecyl bromide, but also ethylene oxide Alkylation of tertiary amines with one long alkyl radical and two methyl groups is particularly easy; the quaternization of tertiary amines with two long radicals and one methyl group can also be carried out with the aid of methyl chloride under mild conditions. Amines that have three long alkyl radicals or hydroxy-substituted alkyl radicals are not very reactive and are quaternized with dimethyl sulfate, for example.
- alkylating agents such as methyl chloride, benzyl chloride, dimethyl sulfate, dodecyl bromide, but also ethylene oxide
- alkylating agents such as methyl chloride, benzyl chloride, dimethyl sulfate, dodecyl bromide
- Possible QAVs are, for example, benzalkonium chloride (N-alkyl-N, N-dimethylbenzylammonium chloride), benzalkon B (m, p-dichlorobenzyldimethyl-Ci2-alkylammonium chloride, benzoxonium chloride (benzyldodecyl bis (2-hydroxyethyl) ammonium chloride), cetrimonium bromide (n -Hexadecyl-N, N-trimethylammonium bromide), benzetonium chloride (N, N dimethyl-N [2- [2- [p- (1,1,3,3-tetramethylbutyl) phenoxy] ethoxy] ethyl] benzyl -.
- benzalkonium chloride N-alkyl-N, N-dimethylbenzylammonium chloride
- benzalkon B m, p-dichlorobenzyldimethyl-Ci2-al
- Preferred QUATS are the benzalkonium chlorides containing C8-C22 alkyl radicals, in particular C 2 -C 4- alkylbenzyl-dimethylammonium chloride.
- Preferred ester quats are methyl N- (2-hydroxyethyl) -N, N-di (tallow acyl-oxyethyl) ammonium methosulfate, bis (palmitoyl) -ethyl-hydroxyethyl-methyl-ammonium-methosulfate or methyl-N, N -bis (acyl-oxyethyl) -N- (2-hydroxyethyl) ammonium methosulfate.
- Commercial examples are sold by Stepan under the trade name Stepantex® ®
- Methylhydroxyalkyldialkoyloxyalkylammonium or those known under the trade name Dehyquart® ® products from BASF SE or the known under the name Rewoquat ® products by manufacturer Evonik.
- the amounts of the individual ingredients in the detergents and cleaning agents are based in each case on the intended use of the composition in question and the person skilled in the art is fundamentally familiar with the magnitudes of the amounts of the ingredients to be used or can take them from the associated specialist literature.
- the surfactant content will be chosen to be higher or lower.
- the surfactant content of detergents can be from 10 to 50% by weight, preferably from 12.5 to 30% by weight and more preferably from 15 to 25% by weight.
- the washing and cleaning agents can contain, for example, at least one water-soluble and / or water-insoluble, organic and / or inorganic builder.
- the water-soluble organic builder substances include polycarboxylic acids, in particular citric acid and sugar acids, monomeric and polymeric aminopolycarboxylic acids, in particular
- polyphosphonic acids especially amino-tris (methylenephosphonic acid), ethylenediaminetetrakis (methylenephosphonic acid) and 1-hydroxyethane-1, 1-diphosphonic acid
- polymeric hydroxy compounds such as dextrin as well as polymeric (poly) carboxylic acids, polymeric acrylic acids, methacrylic acids, maleic acids and Mixed poly
- Suitable, albeit less preferred, compounds of this class are copolymers of acrylic acid or methacrylic acid with vinyl ethers, such as vinyl methyl ethers, vinyl esters, ethylene, propylene and styrene, in which the acid makes up at least 50% by weight.
- the organic builder substances can be used, in particular for the production of liquid detergents and cleaning agents, in the form of aqueous solutions, preferably in the form of 30 to 50 percent by weight aqueous solutions. All of the acids mentioned are generally used in the form of their water-soluble salts, in particular their alkali salts.
- Organic builder substances can, if desired, be present in amounts of up to 40% by weight, in particular up to 25% by weight and preferably from 1% by weight to 8% by weight. Quantities close to the upper limit mentioned are preferably used in pasty or liquid, in particular water-containing, agents according to the invention. Laundry post-treatment agents, such as fabric softeners, can optionally also be free of organic builders.
- Particularly suitable water-soluble inorganic builder materials are alkali metal silicates and polyphosphates, preferably sodium triphosphate.
- water-insoluble, water-dispersible inorganic builder materials in particular crystalline or amorphous alkali metal alumosilicates, if desired, in amounts of up to 50% by weight, preferably not more than 40% by weight and, in liquid compositions, in particular from 1% by weight to 5% by weight. -%, are used.
- the crystalline sodium aluminosilicates in detergent quality in particular zeolite A, P and optionally X, are preferred. Quantities close to the upper limit mentioned are preferably used in solid, particulate compositions.
- Suitable aluminosilicates in particular have no particles with a particle size of more than 30 ⁇ m and preferably consist of at least 80% by weight of particles with a size of less than 10 ⁇ m.
- Suitable substitutes or partial substitutes for said aluminosilicate are crystalline alkali silicates, which can be present alone or in a mixture with amorphous silicates.
- the alkali silicates which can be used as builders in detergents or cleaning agents preferably have a molar ratio of alkali oxide to S1O2 below 0.95, in particular from 1: 1.1 to 1:12, and can be amorphous or crystalline.
- Preferred alkali silicates are the sodium silicates, in particular the amorphous sodium silicates, with a molar ratio Na 2 O: Si0 2 of 1: 2 to 1: 2.8.
- the crystalline silicates used alone or in a mixture with amorphous silicates are preferably crystalline sheet silicates of the general formula Na 2 Si x 0 2x + ryH 2 0, in which x, the so-called modulus, is a number from 1, 9 to 4 and y is a number from 0 to 20 and preferred values for x are 2, 3 or 4.
- Preferred crystalline sheet silicates are those in which x in the general formula mentioned assumes the values 2 or 3.
- both beta and delta sodium disilicates Na 2 Si 2 05-yH 2 0 are preferred.
- a crystalline layered sodium silicate with a module of 2 to 3 is used, as is the case with sand and soda can be produced.
- Crystalline sodium silicates with a modulus in the range from 1.9 to 3.5 are used in a further preferred embodiment of the textile treatment or cleaning agents.
- the weight ratio of aluminosilicate to silicate is preferably 1:10 to 10: 1.
- the weight ratio of amorphous alkali silicate to crystalline alkali silicate is preferably 1: 2 to 2: 1 and in particular 1: 1 to 2: 1.
- builder substances are preferably present in amounts of up to 60% by weight, in particular from 5% by weight to 40% by weight.
- Laundry post-treatment agents such as fabric softeners, are preferably free of inorganic builders.
- an agent according to the invention further comprises at least one enzyme.
- the enzyme can be a hydrolytic enzyme or another enzyme in a concentration suitable for the effectiveness of the agent.
- An embodiment of the invention thus represent agents which comprise one or more enzymes.
- Preferred enzymes that can be used are all enzymes that can develop a catalytic activity in the agent according to the invention, in particular a protease, amylase, cellulase, hemicellulase, mannanase, tannase, xylanase, xanthanase, xyloglucanase, ⁇ -glucosidase, pectinase, carrageenase, perhydrolase, oxidase , Oxidoreductase or a lipase, and mixtures thereof.
- Enzymes are advantageously contained in the agent in an amount of 1 ⁇ 10 8 to 5% by weight, based on active protein.
- Each enzyme is increasingly preferred in an amount of 1 ⁇ 10 -7 -3% by weight, from 0.00001-1% by weight, from 0.00005-0.5% by weight, from 0.0001 to 0 , 1% by weight and particularly preferably from 0.0001 to 0.05% by weight in agents according to the invention, based on active protein.
- the enzymes particularly preferably show synergistic cleaning performance with respect to certain soiling or stains, ie the enzymes contained in the agent composition mutually support one another in their cleaning performance. Synergistic effects can occur not only between different enzymes, but also between one or more enzymes and other ingredients of the agent according to the invention.
- the amylase (s) is preferably an ⁇ -amylase.
- the hemicellulase is preferably a pectinase, a pullulanase and / or a mannanase.
- the cellulase is preferably a cellulase mixture or a one-component cellulase, preferably or predominantly an endoglucanase and / or a cellobiohydrolase.
- the oxidoreductase is preferably an oxidase, in particular a choline oxidase, or a perhydrolase.
- the proteases used are preferably alkaline serine proteases.
- the enzyme contained in the agent according to the invention is a protease.
- the enzymes used in the present case can be naturally occurring enzymes or enzymes that have been modified on the basis of naturally occurring enzymes by one or more mutations in order to positively influence desired properties, such as catalytic activity, stability or disinfecting performance.
- the enzyme in the form of an enzyme product is contained in the agent according to the invention in an amount of 0.01 to 10% by weight, preferably 0.01 to 5% by weight, based on the total weight of the agent.
- the active protein content is preferably in the range from 0.00001 to 1% by weight, in particular 0.0001 to 0.2% by weight, based on the total weight of the agent.
- the protein concentration can be determined with the aid of known methods, for example the BCA method (bicinchoninic acid; 2,2'-bichinolyl-4,4'-dicarboxylic acid) or the biuret method.
- the active protein concentration is determined by titrating the active centers using a suitable irreversible inhibitor (for proteases, for example, phenylmethylsulfonyl fluoride (PMSF)) and determining the residual activity (cf. M. Bender et al., J. Am. Chem. Soc. 88 , 24 (1966), pp. 5890-5913).
- a suitable irreversible inhibitor for proteases, for example, phenylmethylsulfonyl fluoride (PMSF)
- the enzymes to be used can also be packaged together with accompanying substances, for example from fermentation.
- the enzymes are preferably used as liquid enzyme formulation (s).
- the enzymes are not provided in the form of the pure protein, but rather in the form of stabilized, storable and transportable preparations.
- These ready-made preparations include, for example, the solid preparations obtained by granulation, extrusion or lyophilization or, in particular in the case of liquid or gel-like agents, solutions of the enzymes, advantageously as concentrated as possible, with little water and / or with stabilizers or other auxiliaries.
- the enzymes can be encapsulated both for the solid and for the liquid dosage form, for example by spray drying or extrusion of the enzyme solution together with a preferably natural polymer or in the form of capsules, for example those in which the enzymes are enclosed as in a solidified gel or in those of the core-shell type, in which an enzyme-containing core is impermeable to water, air and / or chemicals Protective layer is coated. Additional active ingredients, for example stabilizers, emulsifiers, pigments, bleaches or dyes, can also be applied in superimposed layers.
- Such capsules are applied by methods known per se, for example by pouring or rolling granulation or in fluid-bed processes. Such granules are advantageously low in dust, for example due to the application of polymeric film formers, and due to the coating are stable in storage.
- the agent according to the invention can have one or more enzyme stabilizers.
- Absorption-enhancing agents are agents which improve the absorption of the microcapsules on surfaces, in particular textile surfaces.
- This category of agents includes, for example, the esterquats already mentioned above.
- SRPs soil repellent polymers
- PI polyethyleneimines
- ethoxylated variants thereof and polyesters, in particular esters of terephthalic acid, especially those of ethylene glycol and terephthalic acid or polyester / polyethers of polyethylene terephthalate and polyethylene glycol, may be mentioned.
- anionic and nonionic silicones also fall under this group.
- Exemplary compounds are also disclosed in patent specification EP 2638 139 A1.
- the detergents and cleaning agents can contain further ingredients which further improve the application-related and / or aesthetic properties of the composition depending on the intended use.
- they can use bleaches, bleach activators, bleach catalysts, esterquats, silicone oils, emulsifiers, thickeners, electrolytes, pH adjusters, fluorescent agents, dyes, hydrotopes, foam inhibitors, anti-redeposition agents, solvents, optical brighteners, graying inhibitors, antifouling agents, anti-crease agents, anti-crease agents Color protection agents, wetting improvers, antimicrobial agents, germicides, fungicides, antioxidants, corrosion inhibitors, rinse aids, preservatives, antistatic agents, ironing aids, repellent and impregnating agents, pearlescent agents, polymers, swell and slip agents and UV absorbers, without being limited to them.
- Suitable ingredients and frame compositions for washing and cleaning agent compositions are disclosed, for example, in EP 3 110 393 B1.
- Processes for producing core / shell microcapsules are known to the person skilled in the art.
- an oil-based non-water-soluble or slightly water-soluble core material is used in one of the wall formers containing aqueous phase emulsified or dispersed.
- a wide variety of units are used, from simple stirrers to high-performance dispersers, which distribute the core material into fine oil droplets.
- the wall formers separate from the continuous water phase on the oil droplet surface and can then be crosslinked. This mechanism is used in the in situ polymerization of amino and phenoplast microcapsules and in the coacervation of water-soluble hydrocolloids.
- oil-soluble acrylate monomers are used for wall formation in free-radical polymerization.
- processes are used in which water-soluble and oil-soluble starting materials are reacted at the phase boundary of the emulsion droplets that form the solid shell.
- Examples of this are the reaction of isocyanates and amines or alcohols to form polyurea or polyurethane walls (interfacial polymerization), but also the hydrolysis of silicate precursors with subsequent condensation with the formation of an inorganic capsule wall (sol-gel process).
- a method for producing microcapsules comprising a fragrance as core material and a shell consisting of three layers.
- the very thin second layer serving as a diffusion barrier is preferably presented as a template during production.
- Very small proportions of wall formers of the type mentioned are required to build up this second layer.
- the sensitive templates are preferably equipped with an electrically negative charge after the droplet formation at high stirring speeds by means of suitable protective colloids (e.g. AMPS) so that neither Ostwald ripening nor coalescence can occur.
- suitable protective colloids e.g. AMPS
- the wall former for example a suitable precondensate based on aminoplast resin, can form a much thinner shell (layer) compared to the prior art at a now greatly reduced stirring speed.
- the thickness of the shell can be reduced even further, in particular by adding an aromatic alcohol, e.g. m-aminophenol.
- an aromatic alcohol e.g. m-aminophenol.
- the method comprises at least the following steps: a) producing an oil-in-water emulsion by emulsifying a core material in an aqueous phase, optionally with the addition of protective colloids; b) adding the wall-forming component (s) of the inner shell layer, followed by deposition and curing, the wall-forming component (s) of the inner shell layer being in particular an aldehyde component, an amine component and an aromatic alcohol; c) adding the wall-forming component (s) of the middle shell layer, followed by deposition and curing, the wall-forming component (s) of the middle shell layer being in particular proteins and / or polysaccharides; and d) optionally adding the wall-forming component (s) of the outer shell layer, followed by deposition and curing, the wall-forming component (s) of the outer shell layer in particular being an amine component.
- steps a) and b) can be carried out as follows: a) Production of an oil-in-water emulsion by emulsifying a core material in an aqueous phase in the presence of the wall-forming component (s) of the inner shell layer, optionally with the addition of protective colloids ; b) Deposition and curing of the wall-forming component (s) of the inner shell layer, the wall-forming component (s) of the inner shell layer being in particular an aldehyde component, an amine component and an aromatic alcohol.
- This process can be carried out either sequentially or as a so-called one-pot process.
- sequential process in a first process, only steps a) and b) are carried out until microcapsules are obtained with only the inner layer as a shell (intermediate microcapsules). Subsequently, a portion or the total amount of these intermediate microcapsules is then transferred to a further reactor. The further reaction steps are then carried out in this.
- one-pot process all process steps are carried out in a batch reactor. Performing this without changing the reactor is particularly time-saving.
- the overall system should be tailored to the one-pot process.
- the correct choice of the solids content, the correct temperature control, the coordinated addition of formulation components and the sequential addition of the wall formers is possible in this way.
- the method comprises the production of a water phase by dissolving a protective colloid, in particular acrylamidosulfonate and a methylated prepolymer in water.
- the prepolymer is preferably produced by reacting an aldehyde with either melamine or urea.
- methanol can be used.
- the water phase can be mixed by means of stirring and setting a first temperature, the first temperature being in the range from 30.degree. C. to 40.degree.
- An aromatic alcohol in particular phloroglucinol, resorcinol or aminophenol, can then be added to the water phase and dissolved therein.
- an oil phase can be produced by mixing a fragrance composition or a phase change material (PCM) with aromatic alcohols, in particular phloroglucine, resorcinol or aminophenol.
- aromatic alcohols in particular phloroglucine, resorcinol or aminophenol.
- reactive monomers or diisocyanate derivatives can also be incorporated into the fragrance composition.
- the first temperature can then be set.
- Another step can be the production of a two-phase mixture by adding the oil phase to the water phase and then increasing the speed.
- the emulsification can then be started by adding formic acid. A regular determination of the particle size is recommended. Once the desired particle size has been reached, the two-phase mixture can be stirred further and a second temperature can be set to harden the capsule walls. The second temperature can be in the range from 55 ° C to 65 ° C.
- a melamine dispersion can then be added to the microcapsule dispersion and a third temperature can be set, the third temperature preferably being in the range from 75.degree. C. to 85.degree.
- Another suitable step is the addition of an aqueous urea solution to the microcapsule dispersion.
- the microcapsule dispersion is added to a solution of gelatin and alginate. In this case, this would be followed by cooling to 45 ° C. to 55 ° C. and adjusting the pH of the microcapsule dispersion to a value in the range from 3.8 to 4.3, in particular 3.9.
- the microcapsule dispersion can then be cooled to a fourth temperature, the fourth temperature being in the range from 20 ° C to 25 ° C. It can then be cooled to a fifth temperature, the fifth temperature being in a range from 4 ° C to 17 ° C, in particular 8 ° C.
- the pH of the microcapsule dispersion would then be adjusted to a value in the range from 4.3 to 5.1 and glutaraldehyde or glyoxal would be added.
- the reaction conditions in particular temperature and pH, can be chosen differently depending on the crosslinker.
- the person skilled in the art can derive the respectively suitable conditions from the reactivity of the crosslinker, for example.
- the added amount of glutaraldehyde or glyoxal influences the crosslinking density of the first layer and thus, for example, the tightness and degradability of the microcapsule shell.
- the person skilled in the art can accordingly vary the amount in a targeted manner in order to adapt the profile of properties of the microcapsule.
- a melamine slurry can be produced with melamine, formic acid and water.
- the melamine slurry is then added to the microcapsule dispersion.
- the pH of the microcapsule dispersion would be adjusted to a value in the range from 9 to 12, especially 10 to 11.
- Example 1 Production of the microcapsules according to the invention with a three-layer structure
- reaction mixture 1 Lupasol PA140 and Luracoll SD were weighed into a beaker with addition of water 1 and premixed with a 4 cm dissolver disk. The beaker was fixed in the water bath and stirred with the dissolver disk at 500 rpm at 30 ° C. until a clear solution was formed. As soon as the Luracoll / Lupasol solution was clear and had reached 30-40 ° C., the amount of perfume oil was slowly added and the speed was set (1100 rpm) so that the desired particle size was achieved. The pH of this mixture was then acidified by adding formic acid addition 1.
- the resorcinol solution was then stirred in and preformed for 30-40 minutes while gently stirring. After the preforming time had elapsed, the emulsion temperature was increased to 50 ° C. within 15 minutes. When this temperature was reached, the mixture was increased to 60 ° C over a period of 15 minutes and this temperature was maintained for a further 30 minutes.
- the melafin suspension addition 1 was then adjusted to a pH of 4.5 with the aid of 20% strength formic acid and metered into the reaction mixture over a period of 90 minutes. The temperature was then held for 30 minutes. After the 30 minutes had elapsed, the temperature was initially increased to 70 ° C. over the course of 15 minutes. The temperature was then increased to 80 ° C. over the course of 15 minutes and held for 120 minutes.
- reaction mixture 1 was cooled to room temperature.
- Sodium sulfate was dissolved in water in a separate beaker while stirring with a paddle stirrer at 40-50 ° C.
- Sodium alginate and pig skin gelatin are slowly sprinkled into the heated water.
- reaction mixture 1 was added to the prepared gelatin / sodium alginate solution with stirring.
- formic acid addition 2 was used to adjust the pH to 3.9 by slowly adding it dropwise, after which the heat source was removed.
- the batch was then cooled to room temperature. After reaching room temperature, the reaction mixture was cooled with ice. When a temperature of 8 ° C. was reached, the ice bath was removed and the pH was increased to 4.7 with sodium hydroxide solution addition 1.
- Relugan GT50 was then added. Care was taken to ensure that the temperature did not exceed 16-20 ° C before the Relugan GT50 was added.
- the melafin suspension additive 2 acidified to a pH of 4.5 by means of 20% formic acid, was then slowly metered in. The reaction mixture was then heated to 60 ° C. and held for 60 min when the temperature was reached. After this holding time, the heat source was removed and the microcapsule suspension was gently stirred for 14 hours. After the 14 hours had elapsed, the microcapsule suspension was adjusted to a pH of 10.5 by adding 2 sodium hydroxide solution.
- the resulting microcapsule MK 1 according to the invention was examined with a light microscope. Typical recordings are shown in FIG. To evaluate the MK 1, the pH value, the solids content, the viscosity, the particle size and the content of core material in the slurry are determined. The result is shown in Table 2.
- Example 2 Production of reference microcapsules not according to the invention - melamine-formaldehyde
- Luracoll SD was stirred into deionized water and then Lupasol PA140 was added and stirred until a clear solution was formed. The solution was warmed to 30-35 ° C. in a water bath. The perfume oil was added at 1100 rpm while stirring with a dissolver disk.
- the pH of the oil-in-water emulsion was adjusted to 3.3-3.8 with a 10% formic acid.
- the emulsion was then stirred for a further 30 min at 1100 rpm until a droplet size of 20-30 ⁇ m was reached or correspondingly lengthened until the desired particle size of 20-30 ⁇ m (peak max) was reached.
- the particle size was determined by means of a Beckmann-Coulter device (laser diffraction, Fraunhofer method). The speed was reduced depending on the viscosity so that thorough mixing was ensured.
- the mixture was stirred at 30-40 ° C. for a further 30 minutes at this speed.
- the emulsion was then heated to 60 ° C. and stirred further.
- the melamine suspension was adjusted to a pH of 4.5 with formic acid (10%) and metered into the reaction mixture.
- the batch was kept at 60.degree. C. for 60 minutes and then heated to 80.degree. After stirring for 60 min at 80 ° C., the urea solution was added.
- microcapsule dispersion was filtered through a 200 ⁇ m filter sieve.
- the MF reference microcapsule MK 2 obtained was examined with a light microscope. A typical recording of the MK 2 is shown in FIG. To evaluate the microcapsules obtained, the pH, the solids content, the viscosity, the particle size and the content of core material in the slurry were determined. The result is shown in Table 4.
- Table 5 List of the substances used for the production and the amount used for the reference microcapsules MK3 not according to the invention
- Sodium sulfate was weighed into an 800 ml beaker and dissolved by adding 1 water while stirring with a paddle stirrer.
- the perfume oil was weighed into a separate beaker and heated to 45 ° C. while stirring.
- the heated perfume oil was slowly added to the gelatin-alginate solution and the stirrer speed was increased to 1200 rpm.
- the droplet size was determined using a Beckmann-Coulter device (laser diffraction, Fraunhofer method). After a droplet size of 20-30 pm had been reached, the speed was reduced so that gentle mixing was ensured.
- the sodium sulfate addition 2 was dissolved in a further beaker by means of water addition 2. Concentrated acetic acid was then added to this solution and heated to 45 ° C. with stirring.
- the previously heated acetic acid / sodium sulfate solution was filled into a dropping funnel and metered into the emulsion over a period of 15 minutes.
- the stirring speed was chosen so that thorough mixing is ensured.
- the pH of the microcapsule suspension was then adjusted to 10.5 by slowly adding dropwise sodium hydroxide solution 3 (approx. 20-30 min) while stirring.
- the obtained gelatin reference microcapsules MK 3 were examined with a light microscope. A typical recording of the MK 3 is shown in FIG. 3. To evaluate the microcapsules obtained, the pH, the solids content, the viscosity, the particle size and the content of core material in the microcapsule suspension were determined. The result is shown in Table 8.
- Example 4 Production of a further microcapsule according to the invention with a three-layer structure
- Lupasol PA140 and Luracoll SD were weighed into a beaker with addition of water 1 and premixed with a 4 cm dissolver disk. The beaker was fixed in the water bath and stirred with the dissolver disk at 500 rpm at 30 ° C. until a clear solution was formed.
- the amount of perfume oil was slowly added and the speed was set (1100 rpm) so that the desired particle size was achieved.
- the pH of this mixture was then acidified by adding formic acid addition 1. It was emulsified for 20-30 min or extended accordingly until the desired particle size of 20-30 ⁇ m (peak max) was reached.
- the particle size was determined by means of a Beckmann-Coulter device (laser diffraction, Fraunhofer method). After the particle size had been reached, the speed was reduced in such a way that gentle mixing was ensured.
- the resorcinol solution was then stirred in and preformed for 30-40 minutes while gently stirring. After the preforming time had elapsed, the emulsion temperature was increased to 50 ° C. within 15 minutes. When this temperature was reached, the mixture was increased to 60 ° C over a period of 15 minutes and this temperature was maintained for a further 30 minutes.
- the melafin suspension addition 1 was then adjusted to a pH of 4.5 with the aid of 20% strength formic acid and metered into the reaction mixture over a period of 90 minutes. The temperature was then held for 30 minutes. After the 30 minutes had elapsed, the temperature was initially increased to 70 ° C. over the course of 15 minutes. The temperature was then increased to 80 ° C. over the course of 15 minutes and held for 120 minutes.
- reaction mixture 1 was cooled to room temperature.
- Sodium sulfate was dissolved in water in a separate beaker while stirring with a paddle stirrer at 40-50 ° C.
- Sodium alginate and pig skin gelatin are slowly sprinkled into the heated water.
- reaction mixture 1 was added to the prepared gelatin / sodium alginate solution with stirring.
- formic acid addition 2 was used to adjust the pH to 3.9 by slowly adding it dropwise, after which the heat source was removed.
- the batch was then cooled to room temperature. After reaching room temperature, the reaction mixture was cooled with ice. When a temperature of 8 ° C.
- the melafin suspension additive 2 acidified to a pH of 4.5 by means of 20% formic acid, was slowly metered in.
- the reaction mixture was then heated to 60 ° C. and held for 60 min when the temperature was reached. After this holding time, the heat source was removed and the microcapsule suspension was gently stirred for 14 hours. After the 14 hours had elapsed, the microcapsule suspension was adjusted to a pH of 10.5 by adding 2 sodium hydroxide solution.
- the resulting microcapsule MK 4 according to the invention was examined with a light microscope. Typical recordings are shown in FIG. To evaluate the MK 1 a, the pH, the solids content, the viscosity, the particle size and the content of core material in the slurry were determined. The result is shown in Table 8. Table 8: Analysis results of the microcapsule MK 1a according to the invention
- microcapsules To determine the stability of microcapsules, they were stored for a period of up to 12 weeks in a model fabric softener formulation at 40 ° C. and the concentration of the fragrances diffused from the interior of the capsule into the surrounding formulation was determined using HS-GC / MS. The residual proportion of the perfume oil still in the capsule was calculated based on the measured values.
- microcapsule suspension (slurry) was carefully homogenized and stored in a heating cabinet with a concentration of 1% by weight in the model formulation at 40 ° C., sealed airtight.
- the non-encapsulated odoriferous substance with an analogous odorant substance concentration in the model formulation serves as a comparison.
- the samples were removed from the heating cabinet and an aliquot was weighed into a 20 ml headspace vial. The vial was then closed immediately.
- microcapsules MK 1 and MK 4 according to the invention show a stability comparable to the MF reference microcapsule MK 2 after storage for 12 weeks in a model formulation.
- gelatine / alginate reference microcapsule MK 3 shows no capsule stability in the test medium under the selected test conditions (disintegration already during sample preparation), so that it was not possible to record measured values for stability assessment within the required time frame.
- This experiment is used to assess the rapid biodegradability of the microcapsules.
- the standard test concentration of the samples to be examined is 1000 mg / l O2.
- the measuring heads and the controller measure the oxygen consumption in a closed system. By the consumption of oxygen and the simultaneous binding of the resulting carbon dioxide to soda lye cookies creates a negative pressure in the system.
- the measuring heads register and save this pressure over the set measuring period.
- the stored values are read into the controller by means of infrared transmission. They can be transferred to a PC and evaluated using the Achat OC program.
- Wastewater treatment plant ethylene glycol z.A., Merck reference sample with COD 1000 mg / l 02 walnut shell flour, Senger natural raw materials
- microcapsules MK 1, MK 2, MK 3 and MK 4 were produced according to the descriptions of Examples 1 to 4, with the difference that the completely persistent perfluorooctane (degradation rate ⁇ 1%) was used as the core material instead of the perfume oil. This eliminates any influence of the core material on the test result.
- the capsule dispersion is washed after preparation by centrifuging and redispersing three times in water in order to separate off dissolved residues. For this purpose, a sample of 20-30 mL is centrifuged for 10 minutes at 12,000 revolutions per minute. After suctioning off the clear supernatant, it is made up with 20-30 mL water and the sediment is redispersed by shaking.
- the microcapsule slurries as received from the production were used.
- the microcapsule slurries were washed after production by centrifuging and redispersing three times in water in order to separate off dissolved residues.
- a sample of 20-30 ml is centrifuged for 10 minutes at 12,000 revolutions per minute. After the clear supernatant has been filtered off with suction, it is made up with 20-30 ml of water and the sediment is redispersed by shaking.
- ethylene glycol 711.6 mg were dissolved in a 1 l volumetric flask and made up to the mark. This corresponds to a COD of 1000 mg / l O2.
- Ethylene glycol is considered to be readily biodegradable and serves as a reference here.
- Walnut shell flour consists of a mixture of biopolymers, especially cellulose and lignin, and serves as a bio-based reference based on solids. Due to the slow degradation of walnut shell flour, the course of the test can be followed over the entire period of 60 days. For this purpose, 117.36 g of walnut shell flour were homogeneously dispersed in 1 liter of water with stirring. Aliquots of this mixture were taken with stirring for COD determination. Using the mean COD value of 1290 ⁇ 33 mg / l O2, the required amount was calculated and transferred to the OxiTop bottles with stirring.
- a 20 liter bucket was used to remove activated sludge from the outlet of the activated sludge basin of a factory or municipal wastewater treatment plant. After settling for 30 minutes, the supernatant water was discarded.
- the concentrated organic sludge in the bucket was then permanently aerated for 3 days with the help of the aquarium pump and an air stone.
- the COD value of the samples to be examined was determined using the COD LCK 514 cuvette test.
- the sample is diluted with water until the COD value of 1000 mg / l O2 is reached.
- the biodegradation diagram of the capsule MK 1 according to the invention according to OECD 301 F is shown in FIG. 4 (a).
- the capsule MK 1 according to the invention shows a biodegradability of 76 ⁇ 4% after 28 days.
- the capsule MK 1a according to the invention shows a biodegradability of 78 ⁇ 9% after 28 days.
- the capsule MK 1 according to the invention shows a biodegradability of 47 ⁇ 16% after 60 days.
- a comparison of the biodegradability measurement according to OECD 301 F is shown in FIG. This shows that the microcapsule MK1 according to the invention has a comparable biodegradability to the nature-based reference walnut shell flour with a biodegradability of 53% after 60 days.
- FIG. 5 shows a comparison of the biodegradability measurements according to OECD301 F between the microcapsule MK 1 according to the invention, the MF reference microcapsule MK 2 and the gelatin / alginate reference microcapsule MK 3.
- the specification for the OECD301 F stipulates that the substance to be tested must be tested within a 10-day time window (starting from a Degradation of 10%) must achieve a degree of biological degradation of 60%.
- Both the microcapsule MK 1 according to the invention and the gelatin / alginate reference microcapsule MK 3 show a very rapid biodegradation compared to the MF reference microcapsule MK 2.
- the required time span for a reduction of 60% is already reached after 7 days.
- the degree of degradation of the standard MF capsules MK 2 reaches the range of 10% within a short time and forms a plateau here that indicates no further degradation within the measurement time.
- the cross-linked gelatine-alginate microcapsules MK 3 have proven to be good in terms of biodegradability. They reach a value of 68 ⁇ 5% within 10 days.
- the microcapsule MK 1 according to the invention also shows a degree of degradation of 68 ⁇ 6% after 10 days.
- the poorly degradable reference MK 2 shows no biodegradability in the course of the measurement. Negative readings (especially those in the second half of the Measurement duration) were set to zero.
- the nature-based reference walnut shell flour shows the typical gradual breakdown of a complex mixture of substances. The maximum biodegradability is reached on the 40th day of the measurement, whereby this value remains constant within the range of fluctuation until the end of the measurement after 60 days. A similar degradation behavior can be observed for the microcapsule MK1 according to the invention. After 60 days, an average degree of degradation of 47% is achieved over a step-like course, with the absolute range between 30 and 65% biodegradability.
- This experiment is used to assess the fundamental biodegradability of the microcapsules.
- the inoculum used consists of activated sludge from the Taunusstein-Bleidenstadt wastewater treatment plant ( ⁇ 100 mg dry matter equivalent / L batch). Aniline was used as a control.
- TOC total organic carbon
- test batches were produced in a volume of 3500 ml each.
- the test item and the inoculum were incubated in this volume at room temperature in a mineral nutrient medium. Knowing the TOC of the microcapsule slurry was used to set a carbon concentration of approx. 25 mg C / L. Thus, only the carbon from the test item was available as an energy source for the microorganisms in the inoculum.
- the test batches were aerated with CO2-free compressed air and stirred using a magnetic stirrer. When the test item was broken down by microorganisms, the carbon it contained was converted into carbon dioxide. This gas development was absorbed by means of gas washing bottles mounted on the test attachment.
- the gas washing bottles were filled with a solution of barium hydroxide, which binds the resulting carbon dioxide.
- the carbon dioxide formed in the test batch can be quantified by titration with hydrochloric acid.
- the degree of degradation of the test substance was then calculated by comparing the theoretically formable carbon dioxide (from the TOC measurement) with the actually determined amount of carbon dioxide. Three batches were produced for each test substance, which enables an average degree of degradation to be determined.
- the amount of carbon dioxide produced in the test mixture can be quantified and the degree of degradation of the test substance can be calculated using the following formula:
- Table 11 Representation of the degradation values according to OECD 301 F and OCED 302 C (28 days)
- FIG. 4 (b) The biodegradation diagram according to OECD302C of the capsule MK1 according to the invention is shown in FIG. 4 (b).
- the capsules MK 1 according to the invention show a degradability value of 45 ⁇ 4% after 28 days.
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Abstract
Description
Claims
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PCT/EP2019/084841 WO2021115600A1 (de) | 2019-12-12 | 2019-12-12 | Wasch- und reinigungsmittel umfassend umweltverträgliche mikrokapseln |
PCT/EP2020/085679 WO2021116365A1 (de) | 2019-12-12 | 2020-12-11 | Wasch- und reinigungsmittel umfassend umweltverträgliche mikrokapseln |
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EP4073218A1 true EP4073218A1 (de) | 2022-10-19 |
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EP20820952.8A Pending EP4073218A1 (de) | 2019-12-12 | 2020-12-11 | Wasch- und reinigungsmittel umfassend umweltverträgliche mikrokapseln |
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US (1) | US20230021818A1 (de) |
EP (1) | EP4073218A1 (de) |
WO (2) | WO2021115600A1 (de) |
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EP4351774A1 (de) * | 2021-06-11 | 2024-04-17 | Henkel AG & Co. KGaA | Mittel enthaltend farbneutrale abbaubare mikrokapseln |
EP4101528A1 (de) * | 2021-06-11 | 2022-12-14 | Henkel AG & Co. KGaA | Mittel enthaltend farbneutrale abbaubare mikrokapseln |
US20230183620A1 (en) * | 2021-12-15 | 2023-06-15 | Henkel Ag & Co. Kgaa | Agent containing emulsifier and microcapsules |
EP4198115A1 (de) * | 2021-12-15 | 2023-06-21 | Henkel AG & Co. KGaA | Mittel enthaltend emulgator und mikrokapseln mit parfümzusammensetzung |
EP4198113A1 (de) * | 2021-12-15 | 2023-06-21 | Henkel AG & Co. KGaA | Mittel enthaltend emulgator und mikrokapseln |
EP4212239A1 (de) | 2022-01-14 | 2023-07-19 | International Flavors & Fragrances Inc. | Biologisch abbaubare prepolymermikrokapseln |
WO2024094318A1 (en) * | 2022-11-03 | 2024-05-10 | Symrise Ag | Microcapsules, process for the preparation of microcapsules and use of microcapsules for perfuming a consumer product |
Family Cites Families (21)
Publication number | Priority date | Publication date | Assignee | Title |
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US2800457A (en) | 1953-06-30 | 1957-07-23 | Ncr Co | Oil-containing microscopic capsules and method of making them |
JPS5128589B1 (de) * | 1967-12-28 | 1976-08-20 | ||
KR100523479B1 (ko) * | 2003-05-06 | 2005-10-25 | 주식회사 대하맨텍 | 키토산을 사용한 마이크로캡슐 및 이를 함유하는 조성물 |
US20070148459A1 (en) * | 2005-12-28 | 2007-06-28 | Kimberly-Clark Worldwide, Inc. | Microencapsulated delivery vehicles |
US20090269405A1 (en) | 2008-04-08 | 2009-10-29 | Appian Labs, Llc | Enzyme mediated delivery system |
WO2010003762A1 (de) | 2008-06-16 | 2010-01-14 | Basf Se | Wirkstoffhaltige partikel |
EP2336285B1 (de) | 2009-12-18 | 2013-09-04 | The Procter & Gamble Company | Zusammensetzung mit Mikrokapseln |
CN102858942B (zh) | 2010-03-31 | 2014-07-09 | 荷兰联合利华有限公司 | 在结构化的液体洗涤剂中引入微胶囊 |
US20110268778A1 (en) | 2010-04-28 | 2011-11-03 | Jiten Odhavji Dihora | Delivery particles |
MY162833A (en) | 2010-11-10 | 2017-07-31 | Colgate Palmolive Co | Fabric conditioners containing soil releasing polymer |
DE102011082496A1 (de) | 2011-09-12 | 2013-03-14 | Henkel Ag & Co. Kgaa | Mikrokapselhaltiges Mittel |
EP2689835B1 (de) | 2012-07-26 | 2019-05-08 | Papierfabrik August Koehler SE | Duftölverkapselung |
MX2015002649A (es) | 2012-08-28 | 2015-05-20 | Basf Se | Sistema portador para fragancias. |
US20140066357A1 (en) | 2012-08-30 | 2014-03-06 | P. H. Glatfelter Company | Heat-stable microencapsulated fragrance oils |
EP2897723B1 (de) | 2012-09-24 | 2019-08-28 | Firmenich SA | Mehrschichtige kern-/hüllenmikrokapseln |
WO2015014628A1 (en) | 2013-07-31 | 2015-02-05 | Unilever Plc | Composition comprising a triggered release system |
DE102014203252A1 (de) | 2014-02-24 | 2015-08-27 | Henkel Ag & Co. Kgaa | Photolabile Duftspeicherstoffe |
US11224569B2 (en) * | 2015-01-12 | 2022-01-18 | International Flavors & Fragrances Inc. | Hydrogel capsules and process for preparing the same |
WO2017108722A1 (en) * | 2015-12-21 | 2017-06-29 | Unilever Plc | Triggered release microcapsule |
EP3416610B1 (de) | 2016-02-18 | 2024-08-14 | International Flavors & Fragrances Inc. | Mikrokapselzusammensetzung |
EP3558508B1 (de) | 2016-12-22 | 2022-03-30 | Symrise AG | Mikrokapseln |
-
2019
- 2019-12-12 WO PCT/EP2019/084841 patent/WO2021115600A1/de active Application Filing
-
2020
- 2020-12-11 WO PCT/EP2020/085679 patent/WO2021116365A1/de unknown
- 2020-12-11 US US17/781,422 patent/US20230021818A1/en active Pending
- 2020-12-11 EP EP20820952.8A patent/EP4073218A1/de active Pending
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US20230021818A1 (en) | 2023-01-26 |
WO2021116365A1 (de) | 2021-06-17 |
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