AU2003291848A1 - A tannin, aldehyde, amino compound- based resin composition and its use as a binding agent for composite wood products - Google Patents
A tannin, aldehyde, amino compound- based resin composition and its use as a binding agent for composite wood products Download PDFInfo
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- AU2003291848A1 AU2003291848A1 AU2003291848A AU2003291848A AU2003291848A1 AU 2003291848 A1 AU2003291848 A1 AU 2003291848A1 AU 2003291848 A AU2003291848 A AU 2003291848A AU 2003291848 A AU2003291848 A AU 2003291848A AU 2003291848 A1 AU2003291848 A1 AU 2003291848A1
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- resin composition
- aldehyde
- preparing
- tannin
- amino compound
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- 239000011342 resin composition Substances 0.000 title claims description 56
- 229920001864 tannin Polymers 0.000 title claims description 33
- 239000001648 tannin Substances 0.000 title claims description 33
- 235000018553 tannin Nutrition 0.000 title claims description 33
- 239000002023 wood Substances 0.000 title claims description 19
- 239000011230 binding agent Substances 0.000 title claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title claims description 4
- 239000002131 composite material Substances 0.000 title description 10
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title 1
- 238000000034 method Methods 0.000 claims description 39
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 38
- 150000001299 aldehydes Chemical class 0.000 claims description 28
- -1 amino compound Chemical class 0.000 claims description 24
- 239000000243 solution Substances 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 21
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 20
- 229920005989 resin Polymers 0.000 claims description 18
- 239000011347 resin Substances 0.000 claims description 18
- 239000003381 stabilizer Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 15
- 229920001807 Urea-formaldehyde Polymers 0.000 claims description 11
- 239000004202 carbamide Substances 0.000 claims description 11
- 229920001577 copolymer Polymers 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- 229920002770 condensed tannin Polymers 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 8
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 8
- 229920000877 Melamine resin Polymers 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 239000012141 concentrate Substances 0.000 claims description 6
- 229930003935 flavonoid Natural products 0.000 claims description 6
- 150000002215 flavonoids Chemical class 0.000 claims description 6
- 235000017173 flavonoids Nutrition 0.000 claims description 6
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 claims description 6
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 claims description 4
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 235000010265 sodium sulphite Nutrition 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims description 3
- YZEZMSPGIPTEBA-UHFFFAOYSA-N 2-n-(4,6-diamino-1,3,5-triazin-2-yl)-1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(NC=2N=C(N)N=C(N)N=2)=N1 YZEZMSPGIPTEBA-UHFFFAOYSA-N 0.000 claims description 2
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 claims description 2
- 241000220479 Acacia Species 0.000 claims description 2
- 240000006409 Acacia auriculiformis Species 0.000 claims description 2
- 235000011468 Albizia julibrissin Nutrition 0.000 claims description 2
- 244000241257 Cucumis melo Species 0.000 claims description 2
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 claims description 2
- 240000005852 Mimosa quadrivalvis Species 0.000 claims description 2
- VGGLHLAESQEWCR-UHFFFAOYSA-N N-(hydroxymethyl)urea Chemical compound NC(=O)NCO VGGLHLAESQEWCR-UHFFFAOYSA-N 0.000 claims description 2
- 235000008331 Pinus X rigitaeda Nutrition 0.000 claims description 2
- 235000011613 Pinus brutia Nutrition 0.000 claims description 2
- 241000018646 Pinus brutia Species 0.000 claims description 2
- 235000017343 Quebracho blanco Nutrition 0.000 claims description 2
- 241000065615 Schinopsis balansae Species 0.000 claims description 2
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 claims description 2
- MASBWURJQFFLOO-UHFFFAOYSA-N ammeline Chemical compound NC1=NC(N)=NC(O)=N1 MASBWURJQFFLOO-UHFFFAOYSA-N 0.000 claims description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical group C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 2
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 claims description 2
- 229950005308 oxymethurea Drugs 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 241000894007 species Species 0.000 claims description 2
- 235000005205 Pinus Nutrition 0.000 claims 1
- 241000218602 Pinus <genus> Species 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- HANVTCGOAROXMV-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine;urea Chemical compound O=C.NC(N)=O.NC1=NC(N)=NC(N)=N1 HANVTCGOAROXMV-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- LRBQNJMCXXYXIU-QWKBTXIPSA-N gallotannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@H]2[C@@H]([C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-QWKBTXIPSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- HCITUYXHCZGFEO-UHFFFAOYSA-N 1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N)=N1.N=C1NC(=N)NC(=N)N1 HCITUYXHCZGFEO-UHFFFAOYSA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- 229920002522 Wood fibre Polymers 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- 238000007345 electrophilic aromatic substitution reaction Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 229930001119 polyketide Natural products 0.000 description 1
- 150000003881 polyketide derivatives Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
Landscapes
- Phenolic Resins Or Amino Resins (AREA)
Description
WO 2004/058843 PCT/AU2003/001712 A TANNIN, ALDEHYDE, AMINO COMPOUND-BASED RESIN COMPOSITION AND ITS USE AS A BINDING AGENT FOR COMPOSITE WOOD PRODUCTS Field of the invention This invention relates to resin compositions, methods of making them, and products made by using them. It has particular, although not exclusive application to resin compositions for use as binding agents to bind solid particles together so as to form useful products therefrom. The invention has particular application to the manufacture of wood composite products, such as particle boards and medium density fibreboard (MDF), for use in the construction industry. The background to the invention will therefore be described with specific reference to this application to which it is particularly suited. Background to the Invention The use of non-natural materials in building and construction is nowadays commonplace. In many instances, artificial or synthetic materials have advantages over their natural counterparts, when used in construction. For example, wood based composite materials can have aesthetic and structural advantages over natural timbers. It is therefore desirable to have efficient processes for manufacturing such items, as industry and consumer demand mandate that they be available for use in building projects. One particular kind of wood-based composite product is generically known as 'particle board'. 'Particle board' is made up from wood particulates (typically derived from saw milling and similar techniques for processing natural timbers), combined with a binding agent. Useful binding agents for this purpose are natural and synthetic resins. Synthetic resins have particular advantages in this area, because they can be made to impart desirable properties to the resultant wood composite product (eg: improved water resistance over those possessed by natural timbers). Resins that are made containing condensed tannins are particularly attractive for use in the manufacture of particle board, because tannins are known in particular, for their ability to impart a degree of water resistance to resins formed from them. The use of condensed tannins as binding agents in the manufacture of wood 1 WO 2004/058843 PCT/AU2003/001712 composite materials requires the addition of a cross-linking agent just before their application to the substrate to be bound. Usually, this cross-linking agent is para formaldehyde powder, or a Urea formaldehyde concentrate. Once added to the aqueous tannin solution, a chemical reaction between the two elements commences, which results in the stability (and thus the shelf life) of the resultant resin being compromised. In this context, stability is usually measured as the time taken for the resin system to become unstable, either physically and/or chemically. Tannins (and especially condensed tannins) are poly flavonoids of the general formula X depicted below: Formula X They are poly flavonoids based on a heterocyclic ring system derived from phenylalanine [B] and polyketide [A] biosynthesis. Condensed tannins are classified according to the hydroxylation patterns of the A and B rings. The most common reactions of the A ring are examples of the electrophilic aromatic substitution, including where an electrophile displaces the hydrogen atom at C6 and/or C8. For resorcinolic derivatives, the favoured site is C6. Basic conditions increase the reactivity of the system. The phenolic hydroxyl is a powerful electron donor, especially under basic conditions, increasing the electron density in the A Ring, thus making it a better nucleophile, as well as stabilising carbocation intermediates that result from nucleophilic attack. Condensed tannins contain repeating units of the formula X depicted above, linked to one another by an inter flavonoid bond. The A Ring of the constituent flavonoid units retains only one highly reactive nucleophilic centre, the remainder of each unit accommodating the inter 2 WO 2004/058843 PCT/AU2003/001712 flavonoid bond. In one particular condensed tannin, mimosa tannin, the flavonoid unit is repeated between 2 and 11 times, with an average degree of polymerisation of 4 to 5. An exemplary tannin polymer of the kind described is represented in the formula Y depicted below. H Formula Y Formaldehyde reacts with tannins to produce polymerisation through methylene bridge linkages at reactive sites on the flavonoid molecules, primarily on the A rings. The reactivity for mimosa tannin is comparable to resorcinol. The addition of formaldehyde to a tannin solution results in rapid polymerisation. Due to their size and shape, tannin molecules become immobile at low levels of concentration with formaldehyde, so that reactive sites are too far apart for further methylene bridge formation. The resulting cured resin is thus extremely water- and boil-resistant. The intermolecular distances can be overcome by using bridging agents. One way of achieving this would be to form a polymer with a Urea moiety. A similar approach is currently used for the synthesis of melamine-urea-formaldehyde (MUF) resins. MUF resins are extensively used to impart water resistance to particle board and fibreboard. However, melamine (a petrochemical based material) is subject to large cost fluctuations and is usually more expensive (and often much more expensive) than tannin. Tannin is a natural product, more cost stable, cheaper than Melamine and can potentially be sourced locally. Based on economic considerations, tannins are therefore a suitable candidate for this purpose. However, due to the relatively large size of many tannin molecules, only a relatively small degree of polymeric condensation is required, before the resin 3 WO 2004/058843 PCT/AU2003/001712 viscosity is such that the resin is commercially unusable as a binding agent for forming a composite wood product. In addition, tannin and formaldehyde react readily with one another. This high reactivity makes it very difficult to maintain stability in the final resin solution. Free formaldehyde in the resin solution continues to react with the tannin, thereby increasing its viscosity and at the same time, shortening its shelf life. Conversely, reducing the level of available formaldehyde in the resin does alleviate this problem, but this reduces the reactivity of the components, and thus, the ability of the resin to cure during the formation of wood composite or like products, during manufacture. The present invention aims to address one or more of the prior art problems mentioned above. General disclosure of the Invention The invention generally provides a resin composition, the composition comprising a co-polymer of: (a) a tannin; (b) an amino compound; (c) an aldehyde; and (d) a stabiliser. Preferably, the molar ratios of the elements of the composition (Tannin (molecular weight=1300): Amino compound : Aldehyde).are: 1:13 to 44:15 to 61. Tannins suitable for use in the invention may be obtained from wood and bark materials found throughout the world. Preferred tannins for use in the invention are those known as condensed tannins. These tannins are obtained from the bark of the black wattle (mimosa) and other Acacia species, various species of pine, and from the wood of the quebracho tree. A particularly preferred amino compound for use in the invention is urea. Urea 4 WO 2004/058843 PCT/AU2003/001712 can be used in the form of a powder, prill, in granular form or as an aqueous solution. Amino compounds suitable for this purpose also include the use of urea formaldehyde monomeric products, such as monomethylol urea and dimethylol urea. In order to be suitable for use in the invention, the stabiliser compound chosen must be such as to impart stability to the tannin-amino compound-aldehyde co-polymer. In this context, stability means that the co-polymer has a shelf life of: (a) at least 21 days, when the composition is stored at 124C; or (b) at least 8 days, at 25 0 C. The stabiliser compound may also be an amino-based heterocyclic compound. Suitable compounds in this category include melamine (2,4,6-triamino-1,3,5 triazine), melamine-formaldehyde monomeric products and melamine formaldehyde concentrate solutions. Other suitable triazine materials include benzoguanamine, melam, melon, ammeline and other melamine derivatives. Many aldehydes may be used in the invention. Aldehydes suitable for use in the invention include formaldehyde, acetaldehyde and propionaldehyde. In this specification, the term "Aldehydes" also includes aldehyde generating agents, such as hexamine. Preferably, the aldehyde used in the invention is formaldehyde. This can be used in the invention in many forms, including: *formaldehyde solutions stabilised with methanol; " non-stabilised formaldehyde solutions; e urea formaldehyde solutions (and particularly, concentrated urea formaldehyde solutions); and " paraformaldehyde. In a preferred embodiment, the composition according to the invention is a tannin-urea-formaldehyde co-polymer. The invention also provides a method of preparing a resin composition in 5 WO 2004/058843 PCT/AU2003/001712 which the resin composition comprises a tannin-amino compound-aldehyde co polymer, the method comprising the following steps: (a) reacting the aldehyde with the amino compound so as to derive an amino-aldehyde; and (b) reacting the amino-aldehyde with a tannin. Preferably, in the method aspect of the invention, step (a) is performed before step (b). It is further preferred that in step (a), the aldehyde is reacted with the stabiliser compound under alkaline conditions. A preferred pH range for this reaction is between 7.5 and 9.5. It is further preferred that the molar ratio of aldehyde to stabiliser compound is from 5:1 to 140:1. A particularly preferred molar ratio is about 40:1. It is further preferred that the temperature of the reactants is from 500C to 900C. Preferably, the resulting solution derived from the aldehyde-stabiliser compound reaction is then reacted further with an amino compound under falling pH conditions. Preferably, this further reaction step is performed at pH values from 9.5 to 6.5. Preferably, the reaction is also carried out at temperatures between 80 0 C and atmospheric reflux. Preferably, in step (b) of the method, an aqueous tannin solution containing between 30% and 60% tannin solids (by weight) is then added to the pre-existing reagents according to the preceding steps of the method. Preferably, at this point, the pH in the system is between 5.0 and 7.5. It is further preferred that the temperature of the reaction system is between 400C and 750C. It is further preferred that in step (b) after the tannin solution is added to the reaction system, a further quantity of the amino compound is added to give a molar ratio of aldehyde to amino compound of from 1.45 to 1.9. It is further preferred that the reaction system is then allowed to react until the 6 WO 2004/058843 PCT/AU2003/001712 desired condensation viscosity is achieved. Preferably, the condensation viscosity is between 60 and 200 cps. Preferably further, the reaction is terminated by: (a) rapid cooling to below 400C within 15 -20 minutes; (b) addition of a sulphite; and (c) a final quantity of the amino compound. Preferably, the sulphite comprises sodium sulphite. This can be used either in powder form, or as an aqueous solution. It is also further preferred that the molar ratio of aldehyde to amino compound in the reaction system is adjusted with a quantity of amino-aldehyde concentrate. It is further preferred that the pH is finally adjusted to between 6.5 and 8.0. The invention further comprises a resin composition produced in accordance with the method aspect of the invention. The invention yet further provides a method of using a resin composition containing a tannin-amino-aidehyde co-polymer as a binding agent in the production of a material which comprises solids mixed with the resin. Preferably, the resin composition is a tannin-urea-formaldehyde of the kind previously described. It is further preferred that the products produced by the use of the resin composition are products which contain particulates made from wood (such as wood shavings, wood fibre or other wood particulates) in combination with the resin composition. Particularly preferred wood composite products formed in accordance with the method aspect of the invention include: (a) particle boards; and (b) medium-density fibre boards. Detailed description of a preferred embodiment of the invention A preferred embodiment of the invention will now be described by way of 7 WO 2004/058843 PCT/AU2003/001712 example only, in the following commentary. Example To a reactor, 32.49 grams of 54% formaldehyde solution is charged. The pH of this solution is adjusted to between 8.5 and 9.5 with sodium hydroxide solution. Then, 2.66 grams of melamine powder are added to the reactor and stirred, and the mixture then heated to 80 0 C. To this mixture, a quantity of urea (10.42g) is added to yield a formaldehyde to urea molar ratio of 3.36:1 while mixing. The temperature is allowed to rise to 950C and held there for 10 minutes. After this hold time the pH of the reaction mixture is adjusted to 9.0 to 9.5 with sodium hydroxide solution. The mixture is allowed to cool to 900C at which time a solution of 50% tannin is charged. The temperature is allowed to drop to 700C. Immediately a quantity of urea is added to result in a formaldehyde:urea molar ratio of 1.79:1. The final temperature is maintained at 600C and pH between 5.9 and 6.4. The reacting mixture is then condensed to 140cps measured at 25*C or Gardner tube value F. Upon reaching this viscosity, the reacting mixture is cooled to below 301C while charging 1g of (20%) sodium sulphite solution and 11.25 g of urea. Finally, a quantity of urea formaldehyde concentrate is added to effect a final formaldehyde to urea molar ratio of 1.26:1. The pH of the product is then adjusted to between 7 and 7.5 with sodium hydroxide solution to achieve a final viscosity of between 70 and 90 cps and a solid content of 59.8%. It is to be understood that wherever used in this specification (including both the description and the claims), forms of the word 'comprise' are equivalent in meaning to the corresponding forms of the word 'include', and are thus not to be taken as excluding or implying the exclusion of a feature or integer. 8 WO 2004/058843 PCT/AU2003/001712 It will be also understood that the invention disclosed in this specification extends to all combinations of two or more of the individual features mentioned or evident from or implicit in the text of this specification (including the example given in it). All such different combinations constitute various alternative aspects of the invention. 9
Claims (42)
1. A resin composition comprising a co-polymer of: (a) a tannin; (e) an amino compound; (f) an aldehyde; and (g) a stabiliser.
2. A resin composition as claimed in claim 1, in which the molar ratios of the elements (a) to (c) in the composition are: (a) tannin: 1 (b) amino compound 13 to 44 (c) aldehyde:15 to 61.
3. A resin composition as claimed in claim 1 or claim 2 in which the tannin is derived from a natural source.
4. A resin composition as claimed in claim 3, in which the tannin is derived from wood or bark.
5. A resin composition as claimed in claim 4, in which the resin is a condensed resin.
6. A resin composition as claimed in claim 5, in which the condensed tannin is derived from one or more of the following sources: (a) black wattle (mimosa); (b) another acacia species; (c) a species of pine tree (pinus); and (d) the wood of the quebracho tree.
7. A resin composition as claimed in any of the preceding claims, in which the tannin comprises poly flavonoids of the general formula: 10 WO 2004/058843 PCT/AU2003/001712 r2'2 Ar
8. A resin composition as claimed in any of the preceding claims, in which the amino compound comprises either or both: (a) urea; and (b) a urea-formaldehyde monomeric product.
9. A resin composition as claimed in claim 8, in which the amino compound is urea.
10. A resin composition as claimed in claim 9, in which the urea is in one or more of the following forms: (a) a powder; (b) as prill (c) in granular form; and (d) an aqueous solution. 10 A resin composition as claimed in claim 8, in which the amino compound comprises either or both of: (a) monomethylol urea; and (b) dimethylol urea.
11. A resin composition as claimed in any of the preceding claims, in which the stabiliser imparts stability to the tannin-amino compound-aldehyde co-polymer.
12. A resin composition as claimed in claim 11, in which the composition has a shelf life of: (a) at least 21 days, when the composition is stored at 12 0 C; or (b) at least 8 days, when the composition is stored at 25 0 C. 11 WO 2004/058843 PCT/AU2003/001712
13. A resin composition as claimed in either of claims 11 or 12, in which the stabiliser is an amino-based heterocyclic compound.
14. A resin composition as claimed in claim 13, in which the stabiliser is selected from the group comprising: (a) melamine; (b) melamine-formaldehyde monomeric compounds; (c) melamine-formaldehyde concentrate solutions; (d) benzoguanamine; (e) melam; (f) melon; (g) ammeline; and (h) melamine derivative compounds.
15. A resin composition as claimed in any of the preceding claims, in which the aldehyde is selected from the group comprising: (a) formaldehyde; (b) acetaldehyde; (c) propionaldehyde; and (d) aldehyde generating agents.
16. A resin composition as claimed in claim 15, in which the aldehyde is hexamine.
17. A resin composition as claimed in any of the preceding claims, in which the composition is a tannin-urea-formaldehyde co-polymer.
18. A method of preparing a resin composition in which the composition comprises a tannin-amino compound-aldehyde co-polymer, the method comprising the following steps: (a) reacting the aldehyde with the amino compound so as to derive an amino-aldehyde; and (b) reacting the amino-aldehyde with a tannin. 12 WO 2004/058843 PCT/AU2003/001712
19. A method of preparing a resin composition as claimed in claim 18, in which step (a) is performed before step (b).
20. A method of preparing a resin composition as claimed in claims 18 or 19, in which the aldehyde is reacted with the stabiliser under alkaline conditions.
21, A method of preparing a resin composition as claimed in claim 20, in which the aldehyde is reacted with the stabiliser at a pH value between 7.5 and 9.5.
22. A method of preparing a resin composition as claimed in claim 21, in which the molar ratio of aldehyde to stabiliser is in the range of 5:1 to 40:1.
23. A method of preparing a resin composition as claimed in claim 22, in which the molar ratio of aldehyde to stabiliser is about 40:1.
24. A method of preparing a resin composition as claimed in claims 18 to 23, in which the temperature of the reactants is between 500C and 900C.
25. A method of preparing a resin composition as claimed in any of claims 20 to 24, in which a solution derived from reacting the aldehyde with the stabiliser is reacted with an amino compound.
26. A method of preparing a resin composition as claimed in claim 25, in which the reaction between the solution derived from reacting the aldehyde with the stabiliser and the amino compound is performed at a pH value of between 6.5 and 9.5.
27. A method of preparing a resin composition as claimed in claim 26, in which the reaction between the solution derived from reacting the aldehyde with the stabiliser and the amino compound is performed at a temperature between 800C and atmospheric reflux.
28. A method of preparing a resin composition as claimed in any one of claims 18 and 27, in which in step (b) of the method, an aqueous tannin solution containing between 30% and 60% tannin solids (by weight) is added to the pre-existing reagents. 13 WO 2004/058843 PCT/AU2003/001712
29. A method of preparing a resin composition as claimed in claim 28, in which the pH of the reagents is between 5.0 and 7.5.
30. A method of preparing a resin composition as claimed in claim 29, in which the reaction is conducted at a temperature of between 40 0 C and 75 0 C.
31. A method of preparing a resin composition as claimed in any one of claims 28 to 30, in which, in step (b) of the method, a further quantity of the amino compound is added to the reaction, in order to give a molar ratio of aldehyde to amino compound of between 1.45 and 1.8.
32. A method of preparing a resin composition as claimed in any one of claims 18 to 31, in which the reaction is allowed to progress until the solution achieves a viscosity between 60 and 200 cps.
33. A method of preparing a resin composition as claimed in claim 32, in which the reaction is terminated by: (a) cooling to below 40 0 C within 15 -20 minutes; (b) addition of a sulphite; and (c) addition of a final quantity of the amino compound.
34. A method of preparing a resin composition as claimed in claim 32, in which step (b) comprises adding sodium sulphite to the reaction.
35. A method of preparing a resin composition as claimed in claim 33, in which step (b) comprises adding sodium sulphite in either powdered form or as an aqueous solution, to the reaction.
36. A method of preparing a resin composition as claimed in any one of claims 18 to 35, in which the molar ration of aldehyde to amino compound in the reaction is adjusted with a quantity of amino-aldehyde concentrate.
37. A method of preparing a resin composition as claimed in claim 36, in which the 14 WO 2004/058843 PCT/AU2003/001712 pH of the reaction is finally adjusted to a value between 6.5 and 8.0.
38. A method of preparing a resin composition as claimed in any one of claims 18 to 37, in which the resin composition is a tannin-urea-formaldehyde co polymer.
39. A method of using a resin composition comprising a tannin-amino compound aldehyde co-polymer as claimed in any one of claims 1 to 17 as a binding agent in the production of a material which comprises solids mixed with the resin compound.
40. A method of using a resin composition as claimed in claim 39, in which the resin is a tannin-urea-formaldehyde co-polymer.
41. A method of using a resin composition as claimed in claim 40, in which the solids comprise particulates derived from wood.
42. A method of using a resin composition as claimed in either of claims 39 of 40, in which a material is derived, the material being selected from: (a) particle boards; and (b) medium-density fibre boards. 15
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2003291848A AU2003291848A1 (en) | 2002-12-24 | 2003-12-22 | A tannin, aldehyde, amino compound- based resin composition and its use as a binding agent for composite wood products |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2002953568A AU2002953568A0 (en) | 2002-12-24 | 2002-12-24 | Novel chemical composition, method of making same, and products made therefrom |
| AU2002953568 | 2002-12-24 | ||
| PCT/AU2003/001712 WO2004058843A1 (en) | 2002-12-24 | 2003-12-22 | A tannin, aldehyde, amino compound- based resin composition and its use as a binding agent for composite wood products |
| AU2003291848A AU2003291848A1 (en) | 2002-12-24 | 2003-12-22 | A tannin, aldehyde, amino compound- based resin composition and its use as a binding agent for composite wood products |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2003291848A1 true AU2003291848A1 (en) | 2004-07-22 |
Family
ID=34378322
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003291848A Abandoned AU2003291848A1 (en) | 2002-12-24 | 2003-12-22 | A tannin, aldehyde, amino compound- based resin composition and its use as a binding agent for composite wood products |
Country Status (1)
| Country | Link |
|---|---|
| AU (1) | AU2003291848A1 (en) |
-
2003
- 2003-12-22 AU AU2003291848A patent/AU2003291848A1/en not_active Abandoned
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| Date | Code | Title | Description |
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| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |