CN101817825A - Bi-dihydroxy ethylene urea, derivatives, preparation method and application thereof - Google Patents
Bi-dihydroxy ethylene urea, derivatives, preparation method and application thereof Download PDFInfo
- Publication number
- CN101817825A CN101817825A CN 201010122529 CN201010122529A CN101817825A CN 101817825 A CN101817825 A CN 101817825A CN 201010122529 CN201010122529 CN 201010122529 CN 201010122529 A CN201010122529 A CN 201010122529A CN 101817825 A CN101817825 A CN 101817825A
- Authority
- CN
- China
- Prior art keywords
- ethylene urea
- dihydroxy ethylene
- derivative
- urea
- dihydroxy
- 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
- 238000002360 preparation method Methods 0.000 title abstract description 8
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 18
- 239000000835 fiber Substances 0.000 claims abstract description 13
- 239000004202 carbamide Substances 0.000 claims abstract description 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000004744 fabric Substances 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 8
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 7
- 238000000576 coating method Methods 0.000 claims abstract description 6
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000000694 effects Effects 0.000 claims description 13
- 150000002894 organic compounds Chemical class 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 7
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 3
- 239000004634 thermosetting polymer Substances 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims 3
- 239000003973 paint Substances 0.000 claims 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 33
- 238000006243 chemical reaction Methods 0.000 abstract description 21
- 239000000126 substance Substances 0.000 abstract description 17
- 239000011347 resin Substances 0.000 abstract description 13
- 229920005989 resin Polymers 0.000 abstract description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 9
- 238000004132 cross linking Methods 0.000 abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 7
- 239000001257 hydrogen Substances 0.000 abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 6
- -1 nitrogen methylol Chemical class 0.000 abstract description 6
- 229920000742 Cotton Polymers 0.000 abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 4
- 238000006297 dehydration reaction Methods 0.000 abstract description 4
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 238000009833 condensation Methods 0.000 abstract description 3
- 230000005494 condensation Effects 0.000 abstract description 3
- 239000003431 cross linking reagent Substances 0.000 abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 3
- ARZLUCYKIWYSHR-UHFFFAOYSA-N hydroxymethoxymethanol Chemical compound OCOCO ARZLUCYKIWYSHR-UHFFFAOYSA-N 0.000 abstract description 3
- JMHCCAYJTTWMCX-QWPJCUCISA-M sodium;(2s)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate;pentahydrate Chemical compound O.O.O.O.O.[Na+].IC1=CC(C[C@H](N)C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 JMHCCAYJTTWMCX-QWPJCUCISA-M 0.000 abstract description 3
- 238000010382 chemical cross-linking Methods 0.000 abstract description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract 1
- 244000025254 Cannabis sativa Species 0.000 abstract 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 abstract 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 abstract 1
- 229920000180 alkyd Polymers 0.000 abstract 1
- 230000001153 anti-wrinkle effect Effects 0.000 abstract 1
- 235000009120 camo Nutrition 0.000 abstract 1
- 235000005607 chanvre indien Nutrition 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 239000011487 hemp Substances 0.000 abstract 1
- 229920001568 phenolic resin Polymers 0.000 abstract 1
- 239000005011 phenolic resin Substances 0.000 abstract 1
- 239000002952 polymeric resin Substances 0.000 abstract 1
- 229920005749 polyurethane resin Polymers 0.000 abstract 1
- 229920003002 synthetic resin Polymers 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
- 239000007864 aqueous solution Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 8
- 239000003456 ion exchange resin Substances 0.000 description 8
- 229920003303 ion-exchange polymer Polymers 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- 238000010792 warming Methods 0.000 description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 239000003125 aqueous solvent Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 229920003987 resole Polymers 0.000 description 3
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 2
- 230000002939 deleterious effect Effects 0.000 description 2
- 229920002313 fluoropolymer Polymers 0.000 description 2
- 239000004811 fluoropolymer Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Landscapes
- Phenolic Resins Or Amino Resins (AREA)
Abstract
本发明提供了一种双二羟基乙烯脲及多种衍生物及其制备方法和用途，该类化合物分子结构中含有多个高活性羟基，这种活性羟基可与多种内含活泼氢的聚合物发生脱水缩合交联反应，从而可替代传统内含氮羟甲基或氮羟甲基醚活性官能团的脲/甲醛树脂，三聚氰胺/甲醛树脂、双氰胺/甲醛树脂、鸟粪胺/甲醛树脂等，广泛用作多种含活泼氢的聚合物树脂涂料(如丙烯酸酯树脂、醇酸树脂、聚氨酯树脂、酚醛树脂等)的热固性交联剂，和棉、麻、丝等天然织物纤维的抗皱处理剂及耐水性处理剂。本发明在交联固化使用过程中只释放出水，而不放出任何有害的小分子化合物(如甲醛、甲醇等)，属于环境友好型化学交联剂新品种。The invention provides a kind of bisdihydroxyethylene urea and various derivatives as well as their preparation method and application. The molecular structure of this type of compound contains a plurality of highly active hydroxyl groups, which can be polymerized with various active hydrogen containing The dehydration condensation crosslinking reaction of the substance can replace the traditional urea/formaldehyde resin containing nitrogen methylol or nitrogen methylol ether active functional groups, melamine/formaldehyde resin, dicyandiamide/formaldehyde resin, guanamine/formaldehyde resin etc., widely used as a thermosetting crosslinking agent for a variety of active hydrogen-containing polymer resin coatings (such as acrylate resins, alkyd resins, polyurethane resins, phenolic resins, etc.), and as an anti-wrinkle agent for natural fabric fibers such as cotton, hemp, and silk. Treatment agent and water resistance treatment agent. The present invention only releases water in the process of crosslinking and curing, and does not emit any harmful small molecule compounds (such as formaldehyde, methanol, etc.), and belongs to a new type of environment-friendly chemical crosslinking agent.
Description
Technical field
The present invention relates to a kind of novel organic compound and its multiple derivative molecular structure and synthetic method, more specifically, the present invention relates to the synthetic and method of purification of bi-dihydroxy ethylene urea and multiple derivative thereof,
Background technology
Contain a plurality of N-CH in the molecular structure
2OH (nitrogen methylol) or N-CH
2Urea/the formaldehyde resin of-OR (nitrogen hydroxymethyl ether) active group, melamine/formaldehyde resin, Dyhard RU 100/formaldehyde resin, guanamine/formaldehyde resin etc. are with characteristic such as inexpensive, that the curing cross-linked effect is good, have been widely used as the crease-resistant and water-fast treatment agents of washing of natural fabric fiber such as the linking agent of thermosetting acrylic resin, Synolac, urethane resin, resol, epoxypaint and cotton, fiber crops, silk.It is one of present most popular linking agent kind, the most representative as cyanogen spy (CYTEE) company and Monsanto Company's series trade mark product, but this class linking agent, many when synthetic is raw material with formaldehyde, with polymkeric substance generation chemical reaction the time, all can emit low molecule formaldehyde obnoxious flavour, cause environmental pollution or human body is damaged.Under the pressure of environmental protection pressure, the use of this class linking agent is very limited in recent years.Exploitation environmental protection or eco-friendly novel crosslinker are imperative to substitute this class linking agent product.
Summary of the invention
The objective of the invention is to overcome the deficiency of prior art, a kind of compliance with environmental protection requirements, harmless bi-dihydroxy ethylene urea and derivative thereof are provided;
Another object of the present invention also is to provide the preparation method and the application thereof of a kind of above-mentioned bi-dihydroxy ethylene urea and derivative thereof.
The present invention achieves the above object by following technical solution:
Bi-dihydroxy ethylene urea, its molecular formula and preparation method are:
This method may further comprise the steps:
1), be raw material with oxalic dialdehyde and urea, synthetic bi-dihydroxy ethylene urea under the basic catalyst effect; By strict control urea and oxalic dialdehyde mole proportioning and reaction conditions, can synthesize yield and be the bi-dihydroxy ethylene urea product more than 98% in the reaction process.
2), be raw material with phenol compounds such as bi-dihydroxy ethylene urea and amine, acid amides, under alkalescence or an acidic catalyst effect, synthetic bi-dihydroxy ethylene urea derivative.
3), bi-dihydroxy ethylene urea and derivative thereof are used as fabric fibre finishing composition and thermosetting polymer coating linking agent.
The organic derivative molecular formula and the synthesis preparation method of bi-dihydroxy ethylene urea of the present invention are as follows:
1, bi-dihydroxy ethylene urea derivative building-up reactions principle:
Bi-dihydroxy ethylene urea (chemical formula (1)), can with nearly all amine or amidess such as urea, trimeric cyanamide, Dyhard RU 100, guanamine, imidazoles, through the condensation dehydration reaction, make multiple derivative.By the control of feed molar proportioning, can prepare the derivative of different polymerization degree.Bi-dihydroxy ethylene urea and derivative thereof such as chemical formula (1), chemical formula (2), chemical formula (3), chemical formula (4), chemical formula (5), all have a plurality of activity hydroxies (NH-CH-OH) in the molecular structure, the condensation dehydration reaction can take place and play the crosslinking curing effect in this activity hydroxy with the multiple fluoropolymer resin (as thermosetting acrylate resin, Synolac, urethane resin, resol, Resins, epoxy etc.) that contains reactive hydrogen, or react with natural fabric fibers such as cotton, fiber crops, silks, play crease-resistant, the water-fast effect of washing.This cross-linking chemistry reaction belongs to the polycondensation dehydration reaction, and byproduct of reaction is a water, does not produce any deleterious low molecular compound (as formaldehyde, methyl alcohol etc.).Its crosslinking reaction mechanism is as follows:
Bi-dihydroxy ethylene urea that the present invention relates to and derivative thereof belong to the organic compound of a class new chemical structure, can with the multiple polymkeric substance generation chemical crosslink reaction that contains active hydrogen, thereby the linking agent of type described in alternative traditional background technology.And its specific molecule chemical structure, when having guaranteed it and having contained active hydrogen polymkeric substance generation chemical crosslink reaction, any objectionable impuritiess such as no small molecules formaldehyde are emitted.Satisfy the environmental friendliness requirement fully, its crosslinking curing effect is also quite satisfactory.
Urea/the formaldehyde resin of nitrogenous methylol or nitrogen hydroxymethyl ether active function groups in the alternative tradition of the present invention, melamine/formaldehyde resin, Dyhard RU 100/formaldehyde resin, guanamine/formaldehyde resin etc., be widely used as the crease-resistant treatment agent and the water tolerance treatment agent of natural fabric fibers such as thermoset cross-linked dose of the multiple fluoropolymer resin coating (as acrylate resin, Synolac, urethane resin, resol etc.) that contains reactive hydrogen and cotton, fiber crops, silk.This class novel organic compound specific molecule structure and cross-linking and curing reaction mechanism provided by the invention, determined them in the crosslinking curing use, only to discharge water outlet, and do not emit any deleterious micromolecular compound (as formaldehyde, methyl alcohol etc.), belong to environmentally friendly chemical cross-linking agent new variety.
Embodiment
Embodiment 1,
Bi-dihydroxy ethylene urea is synthetic
With 60g urea; 290g40% oxalic dialdehyde (mol ratio of oxalic dialdehyde and urea is 2: 1); 1.5gNaOH preface adds in the reaction three-necked bottle respectively, starts reaction stirrer, air in the inflated with nitrogen replacement(metathesis)reaction three-necked bottle; under nitrogen protection; be warming up to 60 ± 2 ℃, reaction 2hr is warming up to 80～90 ℃ again; reaction 4hr just makes solid content and is 50% the bi-dihydroxy ethylene urea aqueous solution.In the 50% bi-dihydroxy ethylene urea aqueous solution, add 50g sulfonic acid type polystyrene ion-exchange resin, behind the stirring 1hr, fall ion exchange resin with filter paper filtering, can remove minor N aOH in the product.Obtain the pure bi-dihydroxy ethylene urea aqueous solution, use vacuum rotary evaporator at last under 90 ± 2 ℃ of conditions, deviate from the aqueous solvent in the product, both can obtain the bi-dihydroxy ethylene urea compound of light yellow transparent liquid shape, transformation efficiency and yield are all 〉=99% in this chemical reaction process, product purity 〉=98% is essentially an irreversible chemical reaction process.
Embodiment 2
Synthesizing of bi-dihydroxy ethylene urea derivative I (chemical formula (2))
Add 15g urea among the 50% bi-dihydroxy ethylene urea aqueous solution 350g that includes the Naoh catalyzer of embodiment 1 preparation, at N
2Protection is warming up to 90 ± 2 ℃, stirring reaction 4hr down; promptly make the 52.3% derivative I aqueous solution, in this product water solution, add 50g sulfonic acid type polystyrene ion-exchange resin, behind the stirring at normal temperature 1hr; remove NaOH in the solution; fall ion exchange resin with filter paper filtering, promptly obtain the derivative I pure water solution, use vacuum rotary evaporator; under 90 ± 2 ℃ of conditions; deviate from aqueous solvent in the product, both can make light yellow transparent thick liquid nano derivative I, product yield is more than 98%.
Embodiment 3
Bi-dihydroxy ethylene urea derivative I I's (chemical formula (3)) is synthetic
Add trimeric cyanamide 21g among the 50% bi-dihydroxy ethylene urea aqueous solution 350g that includes NaOH of embodiment 1 preparation, at N
2Protection is warming up to 90 ± 2 ℃, stirring reaction 4hr down; promptly make the 53.3% derivative I I aqueous solution, in this aqueous solution, add 50g sulfonic acid type vinylbenzene ion exchange resin, behind the stirring at room 1hr; remove NaOH in the solution; fall ion exchange resin with filter paper filtering then, promptly obtain derivative I I pure water solution, use vacuum rotary evaporator; under 90 ± 2 ℃ of conditions; take off aqueous solvent in the product, can obtain yellow, transparent, thick liquid nano derivative I I, product yield is more than 97%.
Embodiment 4
Synthesizing of bi-dihydroxy ethylene urea derivative III (chemical formula (4))
The 50% bi-dihydroxy ethylene urea aqueous solution that includes NaOH of embodiment 1 preparation adds Dyhard RU 100 21g, at N among the 350g
2Protection down; be warming up to 90 ± 2 ℃; stirring reaction 5hr; promptly make the 53.3% derivative III aqueous solution; in this aqueous solution, add 50g sulfonic acid type polystyrene ion-exchange resin, behind the stirring at room 1hr, remove NaOH in the solution; fall ion exchange resin with filter paper filtering then, promptly make the derivative III pure water solution.
Claims (15)
1. bi-dihydroxy ethylene urea is characterized in that, this organic compound molecule formula is:
2. a method for preparing the described organic compound bi-dihydroxy ethylene urea of claim 1 is characterized in that, it is to be raw material with oxalic dialdehyde and urea, and its mol ratio is 2: 1,80-90 ℃ of synthetic bi-dihydroxy ethylene urea under the basic catalyst effect.
3. the described bi-dihydroxy ethylene urea of claim 1 is put in order at fabric fibre, in the thermosetting polymer paint field as the application of linking agent.
4. the organic derivative of bi-dihydroxy ethylene urea according to claim 1 is characterized in that, its bi-dihydroxy ethylene urea organic derivative molecular formula is:
5. method for preparing the described organic compound bi-dihydroxy ethylene urea of claim 4 organic derivative, it is characterized in that, it is to be 4: 1 with bi-dihydroxy ethylene urea and urea, mol ratio, and 80-90 ℃ of synthetic bi-dihydroxy ethylene urea promptly gets described bi-dihydroxy ethylene urea derivative under the basic catalyst effect.
6. the described bi-dihydroxy ethylene urea organic derivative of claim 4, in fabric fibre arrangement heat curing-type polymer coating field as the application of linking agent.
7. the organic derivative of bi-dihydroxy ethylene urea according to claim 1 is characterized in that, its bi-dihydroxy ethylene urea organic derivative molecular formula is:
8. method for preparing the described organic compound bi-dihydroxy ethylene urea of claim 7 organic derivative, it is characterized in that, it is to be 6: 1 with bi-dihydroxy ethylene urea and trimeric cyanamide, mol ratio, and 80-90 ℃ of synthetic bi-dihydroxy ethylene urea promptly gets described bi-dihydroxy ethylene urea derivative under the basic catalyst effect.
9. the described bi-dihydroxy ethylene urea organic derivative of claim 7, in fabric fibre arrangement heat curing-type polymer coating field as the application of linking agent.
10. the organic derivative of bi-dihydroxy ethylene urea according to claim 1 is characterized in that, its bi-dihydroxy ethylene urea organic derivative molecular formula is:
11. method for preparing the described organic compound bi-dihydroxy ethylene urea of claim 10 organic derivative, it is characterized in that, it is to be 4: 1 with bi-dihydroxy ethylene urea and Dyhard RU 100, mol ratio, and 80-90 ℃ of synthetic bi-dihydroxy ethylene urea promptly gets described bi-dihydroxy ethylene urea derivative under the basic catalyst effect.
12. the described bi-dihydroxy ethylene urea organic derivative of claim 10, in fabric fibre arrangement heat curing-type polymer coating field as the application of linking agent.
13. the organic derivative of bi-dihydroxy ethylene urea according to claim 4 is characterized in that, its bi-dihydroxy ethylene urea organic derivative molecular formula is:
14. the method for organic compound bi-dihydroxy ethylene urea derivative according to claim 13, it is characterized in that, it is to be 4: 1 with bi-dihydroxy ethylene urea and guanamine, mol ratio, and 80-90 ℃ of synthetic bi-dihydroxy ethylene urea promptly gets described bi-dihydroxy ethylene urea derivative under the basic catalyst effect.
15. the organic derivative of the described bi-dihydroxy ethylene urea of claim 13, in fabric fibre arrangement, in the thermosetting polymer paint field as the application of linking agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010101225292A CN101817825B (en) | 2010-03-08 | 2010-03-08 | Bi-dihydroxy ethylene urea, derivatives, preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010101225292A CN101817825B (en) | 2010-03-08 | 2010-03-08 | Bi-dihydroxy ethylene urea, derivatives, preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101817825A true CN101817825A (en) | 2010-09-01 |
| CN101817825B CN101817825B (en) | 2011-06-15 |
Family
ID=42653117
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010101225292A Active CN101817825B (en) | 2010-03-08 | 2010-03-08 | Bi-dihydroxy ethylene urea, derivatives, preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101817825B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105088764A (en) * | 2015-07-17 | 2015-11-25 | 安徽贵谷电子商务有限公司 | Finishing technology for garment materials |
| TWI718848B (en) * | 2020-01-17 | 2021-02-11 | 長春人造樹脂廠股份有限公司 | Amino resin composition and varnish, coating layer, and product comprising the same |
| CN114891468A (en) * | 2022-05-18 | 2022-08-12 | 西南林业大学 | ENF-grade artificial board adhesive and preparation method thereof |
| US12221525B1 (en) * | 2022-02-14 | 2025-02-11 | Johns Manville | Formaldehyde-free cyclic urea reactive additives for exotherm suppressant compositions |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009080697A1 (en) * | 2007-12-21 | 2009-07-02 | Akzo Nobel N.V. | Thermosetting polymers |
-
2010
- 2010-03-08 CN CN2010101225292A patent/CN101817825B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009080697A1 (en) * | 2007-12-21 | 2009-07-02 | Akzo Nobel N.V. | Thermosetting polymers |
Non-Patent Citations (1)
| Title |
|---|
| 《热固性树脂》 20070731 张伟等 甘脲的合成及其在水性涂料中的应用 29-31 1-15 第22卷, 第4期 2 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105088764A (en) * | 2015-07-17 | 2015-11-25 | 安徽贵谷电子商务有限公司 | Finishing technology for garment materials |
| TWI718848B (en) * | 2020-01-17 | 2021-02-11 | 長春人造樹脂廠股份有限公司 | Amino resin composition and varnish, coating layer, and product comprising the same |
| US12221525B1 (en) * | 2022-02-14 | 2025-02-11 | Johns Manville | Formaldehyde-free cyclic urea reactive additives for exotherm suppressant compositions |
| CN114891468A (en) * | 2022-05-18 | 2022-08-12 | 西南林业大学 | ENF-grade artificial board adhesive and preparation method thereof |
| CN114891468B (en) * | 2022-05-18 | 2023-08-04 | 西南林业大学 | ENF grade wood-based panel adhesive and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101817825B (en) | 2011-06-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101348558B (en) | Enzymatic hydrolysis lignin epoxide resin and preparation thereof | |
| CN101817825B (en) | Bi-dihydroxy ethylene urea, derivatives, preparation method and application thereof | |
| CN104755532B (en) | Multifunctional melamine epoxy resins, methylols and amines | |
| CN110951018A (en) | Apigenin-based bio-based benzoxazine resin and preparation method thereof | |
| CN102167788B (en) | Preparation method of urea formaldehyde resin rubber powder | |
| CN102336878A (en) | Low free phenol phenolic resin and preparation method thereof | |
| Yamini et al. | Cyclocarbonated lignosulfonate as a bio-resourced reactive reinforcing agent for epoxy biocomposite: From natural waste to value-added bio-additive | |
| CN113801523B (en) | Preparation process of environmentally-friendly long fiber composite board for bakelite box | |
| CN101665571B (en) | Polyphenyl methyl siloxane modified epoxy resin and preparation method of high-performance electronic packaging material thereof | |
| CN116948147A (en) | Soybean aglycone-based epoxy resin material and preparation method thereof | |
| CN1322012C (en) | Method for preparing cellulose carbamate by urea intercalation method | |
| CN102070758B (en) | A kind of resorcinol-formaldehyde resin-based solid acid and its preparation method and application | |
| CN101724136B (en) | Novel method for preparing lignosulphonate epoxy resin | |
| JP2009518362A (en) | Etherified melamine-formaldehyde condensate with high solids content and low viscosity | |
| CN110483805A (en) | A method of preparing lignosulphonates | |
| CN105705015A (en) | Etheramines and their use as curing agents or intermediates for polymer synthesis | |
| CN101962431A (en) | Urushiol phosphorous-series flame retardant resin and preparation method thereof | |
| CN102585210A (en) | Phenolphthalein polyaryletherketone and preparation method thereof | |
| CN103497358A (en) | Coated hypophosphite and preparation method thereof | |
| CN102344683A (en) | Flame retardant cyanate resin and its preparation method | |
| WO2024134449A1 (en) | Improved bonding resin | |
| CN101643799A (en) | Method for preparing formaldehyde-free retanning agent | |
| US9518035B2 (en) | Method for preparing glycidol using glycerol and glycidol obtained thereby | |
| El‐Zawawy et al. | Synthesis and characterization of cellulose resins | |
| CN117904899B (en) | Preparation method of modified melamine impregnated paper |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CP01 | Change in the name or title of a patent holder |
Address after: 528100 fan Lake Economic Development Zone, Leping Town, Sanshui District, Guangdong, Foshan Patentee after: GUANGDONG YINYANG ENVIRONMENT-FRIENDLY NEW MATERIALS Co.,Ltd. Address before: 528100 fan Lake Economic Development Zone, Leping Town, Sanshui District, Guangdong, Foshan Patentee before: GUANGDONG YINYANG RESIN Co.,Ltd. |
|
| CP01 | Change in the name or title of a patent holder | ||
| EE01 | Entry into force of recordation of patent licensing contract | ||
| EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20100901 Assignee: Guangdong Yaoda Financial Leasing Co.,Ltd. Assignor: GUANGDONG YINYANG ENVIRONMENT-FRIENDLY NEW MATERIALS Co.,Ltd. Contract record no.: X2021980003247 Denomination of invention: Dihydroxy vinyl urea and its derivatives, preparation method and application thereof Granted publication date: 20110615 License type: Exclusive License Record date: 20210506 |
|
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Dihydroxy vinyl urea and its derivatives, preparation method and application thereof Effective date of registration: 20210508 Granted publication date: 20110615 Pledgee: Guangdong Yaoda Financial Leasing Co.,Ltd. Pledgor: GUANGDONG YINYANG ENVIRONMENT-FRIENDLY NEW MATERIALS Co.,Ltd. Registration number: Y2021980003370 |
|
| PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
| PC01 | Cancellation of the registration of the contract for pledge of patent right |
Granted publication date: 20110615 Pledgee: Guangdong Yaoda Financial Leasing Co.,Ltd. Pledgor: GUANGDONG YINYANG ENVIRONMENT-FRIENDLY NEW MATERIALS Co.,Ltd. Registration number: Y2021980003370 |
|
| PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
| EC01 | Cancellation of recordation of patent licensing contract |
Assignee: Guangdong Yaoda Financial Leasing Co.,Ltd. Assignor: GUANGDONG YINYANG ENVIRONMENT-FRIENDLY NEW MATERIALS Co.,Ltd. Contract record no.: X2021980003247 Date of cancellation: 20240613 |
|
| EC01 | Cancellation of recordation of patent licensing contract | ||
| PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Dihydroxyethylurea and its derivatives, as well as their preparation methods and applications Granted publication date: 20110615 Pledgee: Guangdong Yaoda Financial Leasing Co.,Ltd. Pledgor: GUANGDONG YINYANG ENVIRONMENT-FRIENDLY NEW MATERIALS Co.,Ltd. Registration number: Y2024980043951 |
|
| PE01 | Entry into force of the registration of the contract for pledge of patent right |