AU2001237802A1 - Adhesive composition with increased cure rate - Google Patents
Adhesive composition with increased cure rateInfo
- Publication number
- AU2001237802A1 AU2001237802A1 AU2001237802A AU2001237802A AU2001237802A1 AU 2001237802 A1 AU2001237802 A1 AU 2001237802A1 AU 2001237802 A AU2001237802 A AU 2001237802A AU 2001237802 A AU2001237802 A AU 2001237802A AU 2001237802 A1 AU2001237802 A1 AU 2001237802A1
- Authority
- AU
- Australia
- Prior art keywords
- formaldehyde
- adhesive composition
- adhesive
- compound
- resin
- 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.)
- Granted
Links
- 239000000853 adhesive Substances 0.000 title claims description 55
- 230000001070 adhesive effect Effects 0.000 title claims description 55
- 239000000203 mixture Substances 0.000 title claims description 34
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 91
- 229920005989 resin Polymers 0.000 claims description 28
- 239000011347 resin Substances 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 25
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 17
- 239000004202 carbamide Substances 0.000 claims description 17
- 229920003180 amino resin Polymers 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 11
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 11
- 229920000877 Melamine resin Polymers 0.000 claims description 10
- -1 amino compound Chemical class 0.000 claims description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000003825 pressing Methods 0.000 description 6
- 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 5
- 239000002245 particle Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002516 radical scavenger Substances 0.000 description 4
- 239000001993 wax Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- 229920001807 Urea-formaldehyde Polymers 0.000 description 3
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 239000001166 ammonium sulphate Substances 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004160 Ammonium persulphate Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- JHEXGENUDVZLKI-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]urea Chemical compound NC(=O)NNC1=NC(N)=NC(N)=N1 JHEXGENUDVZLKI-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000004411 aluminium Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000001164 aluminium sulphate Substances 0.000 description 1
- 235000011128 aluminium sulphate Nutrition 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- 235000019395 ammonium persulphate Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- BUACSMWVFUNQET-UHFFFAOYSA-H dialuminum;trisulfate;hydrate Chemical compound O.[Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O BUACSMWVFUNQET-UHFFFAOYSA-H 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000011777 magnesium Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- YSRVJVDFHZYRPA-UHFFFAOYSA-N melem Chemical compound NC1=NC(N23)=NC(N)=NC2=NC(N)=NC3=N1 YSRVJVDFHZYRPA-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011591 potassium Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 229910052725 zinc Chemical class 0.000 description 1
- 239000011701 zinc Chemical class 0.000 description 1
Description
ADHESIVE COMPOSITION WITH INCREASED CURE RATE
The invention relates to an adhesive composition on the basis of a formaldehyde-containing aminoplast resin with an increased cure speed and a method for the preparation thereof. Further the invention relates to a method for the preparation of board material with application of the adhesive composition obtained. An adhesive composition on the basis of a formaldehyde- containing aminoplast resin with an increased cure speed and a method for the preparation thereof is known from EP-A-436485. In this patent publication a method is described for accelerated curing of aminoplast adhesives and wood- based materials manufactured with application thereof. For the accelerated curing of aminoplast adhesives an accelerator-catcher system is used, wherein a urea- formaldehyde mixture as an accelerator and a formaldehyde scavenger are added to the adhesive. The addition of a formaldehyde scavenger prevents increasing of the formaldehyde emission. As formaldehyde scavenger urea is used in EP-A- 436485. In the urea formaldehyde accelerator the molar ratio urea: formaldehyde lies between 1 :3 and 1:6. The quantity of accelerator used is 0.1-5 wt.% relative to the quantity of adhesive. The quantity of formaldehyde scavenger can be up to 10 wt. % relative to the quantity of adhesive.
In practice, it is a disadvantage of subsequent addition of urea to bind formaldehyde that the method is unnecessarily complicated. Another disadvantage of the subsequent addition of urea is that the resin must be cured at a lower temperature to counter decomposition of urea and associated development of fumes during curing. The subsequent addition of urea also has an adverse effect on the resin stability.
It was found that the cure speed of an aminoplast adhesive can be increased considerably with an adhesive composition prepared from an aminoplast resin, with a free formaldehyde-like compound being also present and with the quantity of the free formaldehyde-like compound lying between 1 and 50 wt. % relative to the total quantity of formaldehyde added during the adhesive preparation. By 'formaldehyde-like compounds' are meant compounds which can react as formaldehyde. If formaldehyde is used as free formaldehyde-like compound, it is preferably used in a quantity of between 2 and 15 wt. % relative to the total quantity of formaldehyde added during the adhesive preparation.
It was found in particular that the cure speed of an adhesive can be increased considerably with an adhesive composition consisting of an aminoplast resin, with a free formaldehyde-like compound being also present and with the F/(NH2)2 ratio of the total adhesive composition lying between 0.8 and 1.6. The F/(NH2)2 ratio is the molar ratio of the formaldehyde equivalents and the NH2 groups present.
The F/(NH2)2 ratio of the total adhesive composition is preferably 0.9-1.5.
As aminoplast resin are used in the present invention condensation products of an amino compound with a free formaldehyde-like compound.
As amino compound urea, melamine, melam, melem, ureidomelamine and mixtures of these compounds can be used. Preferably urea and/or melamine are used, more in particular a mixture of urea and melamine with a melamine/urea molar ratio varying between 0.01 and 2, in particular between 0.02 and 1.
As formaldehyde-like compounds can be used which can react as formaldehyde. Examples are formaldehyde and paraformaldehyde. Paraformaldehyde is the polymer or oligomer form of formaldehyde which splits off formaldehyde at depolymerization. Paraformaldehyde with a degree of polymerization degree of n can generate n molecules of formaldehyde and thus n formaldehyde equivalents.
Surprisingly it was found that despite the addition of a formaldehyde-like compound during the adhesive preparation, the formaldehyde- emission of the ultimately manufactured board material remains within the internationally applicable standards.
The invention also relates to a method for the preparation of an aminoplast adhesive with an increased cure speed by: - reacting an amino compound with a formaldehyde-like compound to form a resin, which resin is converted into an aminoplast adhesive by addition of a formaldehyde-like compound and a catalyst until an F/(NH2)2 ratio of 0.8-1.6 is obtained.
Catalysts which together with the resin form the adhesive are metal salts, preferably salts of sodium, potassium, ammonium, aluminium, magnesium and zinc. Examples of suitable salts are sodium nitrate, aluminium sulphate, ammonium hydrogenphosphate, ammonium persulphate, ammonium
chloride, ammonium sulphate and ammonium nitrate. Preferably ammonium salts are used and in particular ammonium chloride or ammonium sulphate.
The invention furthermore relates to the manufacture of board material by combining cellulose-containing materials with an adhesive in a press and in this press process these to board material at an elevated temperature and pressure, using as adhesive an adhesive composition consisting of an aminoplast resin, with a free formaldehyde-like compound being also present so that the F/(NH2)2 ratio of the total adhesive composition is equal to 0.8-1.6.
Preferably the method is used in the production of multiplex, particle board, MDF board (medium-density fibreboard), HDF board (high-density fibre board) or OSB board (oriented-strand board).
Preparing the adhesive according to the invention by adding to the resin a formaldehyde-like compound and a catalyst takes place shortly before the board production. The order in which the two components are added to the resin is not critical. The catalyst and the formaldehyde-like compound can also be added at the same time to the resin. The resin has at room temperature sufficient stability to be able to be stored for a few days. After addition of the formaldehydelike compound and the catalyst the adhesive is used for 10 seconds to 1 hour for the preparation of board material, preferably for 30 seconds to 30 minutes. The pressing conditions during the preparation of board material depend on the kind of board material. Thus, for the production of multiplex a pressure of 1-2 MPa is applied, for particle board a pressure of 1-5 MPa, preferably 2-4 MPa, and for MDF a pressure of 2-7 MPa, preferably 3-6 MPa. The temperature at which the board material is manufactured is generally 100-140°C in the case of multiplex, 180-230°C for particle board and OSB and 170-230°C for MDF. In the case of multiplex the board is kept under said conditions for 5-10 minutes (pressing time). For particle board, MDF and OSB a pressing time is applied which is expressed in seconds per mm board thickness. For OSB board the pressing time is 4-12 sec/mm, preferably 6-10 sec/mm. For particle board a pressing time of 4-12 sec/mm, preferably 5-10 sec/mm is generally adopted. MDF boards are manufactured with a pressing time of 5-17 sec/mm, in particular 8-14 sec/mm.
It was found that an increase in cure speed up to 40% was obtained. During the adhesive preparation waxes are generally added to the adhesive composition to make the final board material more resistant to
moisture absorption. The waxes are generally emulsion waxes or solid waxes and originate for example from the petroleum industry.
The invention will be elucidated further by means of the following examples.
Example I
269.2 grams of a urea-formaldehyde precondensate with a formaldehyde/urea (F/U) molar ratio of 5.0 and a solid content of 80%, was introduced into a reactor at room temperature, after which 99.6 grams of water was added. The temperature was increased to 65°C, after which the solution was neutralized with 2 N NaOH until a pH of 7.3 was reached. Afterwards 91.5 grams of urea was added, so that a formaldehyde/urea (F/U) molar ratio of 2.0 was obtained. In the course of 10 minutes the temperature was gradually raised from 65°C to 100°C, after which methylolation was carried out for 5 minutes. Then 2 N acetic acid was added until a pH of 5.5 was reached. The mixture obtained was condensed at 100°C until a viscosity of 450 MPa.s was obtained. 2.5 ml 2 N NaOH was added to obtain a pH of 8. Then the temperature was lowered to 90°C, followed by the addition of 240 grams of melamine (m) and subsequently 166 grams of formalin (50 wt. % formaldehyde in water) was added to a F/(NH2)2 of 1.452. Hereafter the condensation reaction was carried out for 58 minutes, with every 10 minutes 1 ml 2 N NaOH being added. Subsequently the resin mixture obtained was cooled to 25°C. When a temperature of 60°C had been reached the addition of 120 grams of urea was started, 1 ,000 grams of melamine-urea- formaldehyde (MUF) resin being ultimately obtained with an F/(NH2)2 of 1.6. This MUF resin was converted into MUF adhesive by addition of 2 mol% of ammonium sulphate solution (20 wt. % in water) and 18 grams of formalin (50 wt. % formaldehyde in water), resulting ultimately in an F/(NH2)2 of 1.10. The adhesive obtained contained 24 wt. % melamine and 27 wt. % urea.
The gel time of the resulting MUF adhesive was measured. This gel time is a measure of the cure speed of the adhesive.
The gel time is measured as follows. The resin is diluted with water to a solid content of 50%, after which the catalyst is added at room temperature. 5 grams of the mixture of resin and catalyst is put in a test tube, which is then placed in a water bath with a temperature of 100°C. The gel time is the time that has expired between the introduction of the test tube into the water bath and the occurrence of a gel in the tube. The end point of the reaction is
unambiguous and reproducible.
In table 1 the quantity of applied melamine in the adhesive, the F/(NH2)2 ratio before and after the addition of the formaldehyde-like compound (FH), the quantity of catalyst and the gel time are stated.
Examples II - XVII
Analogously to example I adhesive compositions were prepared and gel times were measured, the quantity of melamine being varied as well as the quantities of extra formaldehyde added to the resin and the quantities of catalyst. In table 1 the compositions together with the measured gel times are shown.
Comparative examples IA - XVI IA
Analogously to example I an adhesive composition was prepared by adding to the resin a catalyst, but without extra formaldehyde being added to the resin during the adhesive preparation. The compositions and gel times are also shown in table 1.
Table 1
Claims (9)
1. Adhesive composition prepared from a formaldehyde-containing aminoplast resin, characterised in that a free formaldehyde-like compound is present and that the quantity of the free formaldehyde-like compound lies between 1 and 50 wt. % relative to the total quantity of formaldehyde added during the adhesive preparation.
2. Adhesive composition according to claim 1, characterised in that formaldehyde is used as free formaldehyde-like compound, in a quantity of between 2 and 15 wt. % relative to the total quantity of formaldehyde added during the adhesive preparation.
3. Adhesive composition according to claims 1-2, characterised in that a free formaldehyde-like compound is present so that the F/(NH2)2 of the total adhesive composition is equal to 0.8-1.6.
4. Adhesive composition according to claim 3, characterised in that the
F/(NH2)2 ratio of the adhesive composition is 0.9-1.5.
5. Adhesive composition according to claims 1-4, characterised in that a mixture of urea and melamine is used as amino compound in the aminoplast resin.
6. Adhesive composition according to claim 5, characterised in that the melamine/urea molar ratio is 0.01-2.
7. Method for the preparation of an aminoplast adhesive with an increased cure rate by reacting an amino compound with a formaldehyde-like compound to form a resin, characterised in that this resin is converted into an aminoplast adhesive by addition of a formaldehyde-like compound and a catalyst until an F/(NH2)2 ratio of 0.8-1.6 is achieved.
8. Method for the preparation of board material by combining cellulose- containing materials and an adhesive in a press and in this press process these to board material at an elevated temperature and pressure, characterised in that as adhesive an adhesive composition is used consisting of an aminoplast resin, a free formaldehyde-like compound being also present and the F/(NH2)2 ratio of the total adhesive composition being equal to 0.8-1.6.
9. Adhesive composition, process and board material as following from the description and the examples.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1014433 | 2000-02-18 | ||
| NL1014433A NL1014433C2 (en) | 2000-02-18 | 2000-02-18 | Glue composition with increased curing speed. |
| PCT/NL2001/000092 WO2001060937A1 (en) | 2000-02-18 | 2001-02-05 | Adhesive composition with increased cure rate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2001237802A1 true AU2001237802A1 (en) | 2001-11-08 |
| AU2001237802B2 AU2001237802B2 (en) | 2004-11-25 |
Family
ID=19770850
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU3780201A Pending AU3780201A (en) | 2000-02-18 | 2001-02-05 | Adhesive composition with increased cure rate |
| AU2001237802A Ceased AU2001237802B2 (en) | 2000-02-18 | 2001-02-05 | Adhesive composition with increased cure rate |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU3780201A Pending AU3780201A (en) | 2000-02-18 | 2001-02-05 | Adhesive composition with increased cure rate |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6881817B2 (en) |
| EP (1) | EP1263914B1 (en) |
| CN (1) | CN1202194C (en) |
| AR (1) | AR027413A1 (en) |
| AT (1) | ATE464363T1 (en) |
| AU (2) | AU3780201A (en) |
| BG (1) | BG107110A (en) |
| BR (1) | BR0108479B1 (en) |
| CO (1) | CO5231259A1 (en) |
| DE (1) | DE60141818D1 (en) |
| DK (1) | DK1263914T3 (en) |
| ES (1) | ES2342712T3 (en) |
| HU (1) | HUP0300021A2 (en) |
| MY (1) | MY140746A (en) |
| NL (1) | NL1014433C2 (en) |
| NZ (1) | NZ520843A (en) |
| PL (1) | PL207012B1 (en) |
| PT (1) | PT1263914E (en) |
| SK (1) | SK287450B6 (en) |
| TW (1) | TWI229118B (en) |
| WO (1) | WO2001060937A1 (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2004321917B2 (en) * | 2004-07-27 | 2011-08-25 | Duluxgroup (Australia) Pty Ltd | System for providing powder coated reconstituted cellulosic substrate |
| EP1681147A1 (en) * | 2005-01-13 | 2006-07-19 | DSM IP Assets B.V. | Oriented strand board |
| AU2006217208A1 (en) * | 2005-01-13 | 2006-08-31 | Dsm Ip Assets B.V. | Oriented Strand Board |
| US20080000581A1 (en) * | 2006-06-28 | 2008-01-03 | Gilles Leon Nison | Preparation of laminated composite substrates using coated oriented polymeric film |
| US8809477B2 (en) | 2010-02-01 | 2014-08-19 | Johns Manville | Formaldehyde-free protein-containing binder compositions |
| US8754185B2 (en) | 2010-11-10 | 2014-06-17 | Georgia-Pacific Chemicals Llc | Methods for making and using amino-aldehyde resins |
| US9346926B2 (en) | 2013-03-14 | 2016-05-24 | Georgia-Pacific Chemicals Llc | High flow urea-formaldehyde powders for particleboard and fiberboard manufacture |
| CN103832870B (en) * | 2014-03-19 | 2016-04-13 | 上海福耀客车玻璃有限公司 | A kind of Fast Installation and from dynamic circuit breaker adhesive tape device |
| US10059028B2 (en) * | 2014-11-13 | 2018-08-28 | Fpinnovations | Method for scavenging free formaldehyde using multifunctional scavenger for wooden composite products with urea-formaldehyde resin |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH188327A (en) * | 1934-07-02 | 1936-12-31 | Chem Ind Basel | Durable dry glue preparation. |
| DE2747830A1 (en) * | 1977-10-26 | 1979-05-10 | Basf Ag | PROCESS FOR THE PRODUCTION OF WOOD GLUE |
| FR2625207B1 (en) * | 1987-12-23 | 1991-12-06 | Charbonnages Ste Chimique | NEW PROCESS FOR THE PREPARATION OF AMINOPLAST RESINS WITH VERY LOW-FORMALGEN CLEARANCE |
| AT395014B (en) * | 1989-12-15 | 1992-08-25 | Krems Chemie Gmbh | METHOD FOR THE ACCELERATED CURING OF AMINOPLASTIC GLUE |
-
2000
- 2000-02-18 NL NL1014433A patent/NL1014433C2/en not_active IP Right Cessation
-
2001
- 2001-02-05 DE DE60141818T patent/DE60141818D1/en not_active Expired - Lifetime
- 2001-02-05 SK SK1184-2002A patent/SK287450B6/en not_active IP Right Cessation
- 2001-02-05 HU HU0300021A patent/HUP0300021A2/en unknown
- 2001-02-05 WO PCT/NL2001/000092 patent/WO2001060937A1/en not_active Ceased
- 2001-02-05 ES ES01910222T patent/ES2342712T3/en not_active Expired - Lifetime
- 2001-02-05 PL PL357439A patent/PL207012B1/en unknown
- 2001-02-05 CN CNB018052479A patent/CN1202194C/en not_active Expired - Fee Related
- 2001-02-05 EP EP20010910222 patent/EP1263914B1/en not_active Expired - Lifetime
- 2001-02-05 BR BRPI0108479-8A patent/BR0108479B1/en not_active IP Right Cessation
- 2001-02-05 NZ NZ520843A patent/NZ520843A/en not_active IP Right Cessation
- 2001-02-05 AT AT01910222T patent/ATE464363T1/en active
- 2001-02-05 AU AU3780201A patent/AU3780201A/en active Pending
- 2001-02-05 PT PT01910222T patent/PT1263914E/en unknown
- 2001-02-05 DK DK01910222T patent/DK1263914T3/en active
- 2001-02-05 AU AU2001237802A patent/AU2001237802B2/en not_active Ceased
- 2001-02-09 TW TW90102951A patent/TWI229118B/en active
- 2001-02-13 AR ARP010100633 patent/AR027413A1/en active IP Right Grant
- 2001-02-15 MY MYPI20010686A patent/MY140746A/en unknown
- 2001-02-16 CO CO01012483A patent/CO5231259A1/en not_active Application Discontinuation
-
2002
- 2002-08-19 US US10/222,963 patent/US6881817B2/en not_active Expired - Fee Related
- 2002-09-17 BG BG107110A patent/BG107110A/en unknown
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