CN1138823C - Water-dispersed polyisocyanic ester cross-linking agent - Google Patents
Water-dispersed polyisocyanic ester cross-linking agent Download PDFInfo
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- CN1138823C CN1138823C CNB001169912A CN00116991A CN1138823C CN 1138823 C CN1138823 C CN 1138823C CN B001169912 A CNB001169912 A CN B001169912A CN 00116991 A CN00116991 A CN 00116991A CN 1138823 C CN1138823 C CN 1138823C
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- Prior art keywords
- linking agent
- water
- dispersed
- polymeric polyisocyanate
- cross
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- Expired - Fee Related
Links
- 239000003431 cross linking reagent Substances 0.000 title claims abstract description 19
- 150000002148 esters Chemical class 0.000 title claims description 16
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 21
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 239000003085 diluting agent Substances 0.000 claims abstract description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 29
- -1 ethylene glycol monoalkyl ethers Chemical class 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 claims description 4
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000005516 engineering process Methods 0.000 claims description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 4
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000000539 dimer Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 15
- 239000011248 coating agent Substances 0.000 abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 5
- 239000011527 polyurethane coating Substances 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 4
- 150000001346 alkyl aryl ethers Chemical class 0.000 abstract description 3
- 238000001035 drying Methods 0.000 abstract description 3
- 238000005187 foaming Methods 0.000 abstract description 3
- 239000011347 resin Substances 0.000 abstract description 3
- 229920005989 resin Polymers 0.000 abstract description 3
- 239000004814 polyurethane Substances 0.000 abstract description 2
- 229920002635 polyurethane Polymers 0.000 abstract description 2
- 229920000151 polyglycol Polymers 0.000 abstract 2
- 239000010695 polyglycol Substances 0.000 abstract 2
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical group NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 238000004945 emulsification Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical class CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- HDONYZHVZVCMLR-UHFFFAOYSA-N N=C=O.N=C=O.CC1CCCCC1 Chemical class N=C=O.N=C=O.CC1CCCCC1 HDONYZHVZVCMLR-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229920003009 polyurethane dispersion Polymers 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
Abstract
The present invention relates to a cross-linking agent, particularly to a water-dispersible polyurethane cross-linking agent for aqueous double-component polyurethane coating, and a preparing method thereof. The cross-linking agent of the present invention is obtained by that polyisocyanate of which the average carbimide functionality is from 2.5 to 5 and polyglycol monoalkyl ether of which the molecular weight is from 300 to 800 carry out a chemical reaction under the condition of certain temperature, wherein the addition quantity of the polyglycol monoalkyl ether accounts for 10 to 25% of the weight of the polyisocyanate. The cross-linking agent contains a diluting agent of which the weight accounts for 10 to 50% of that of the cross-linking agent. Coating mixed with aqueous hydroxy resin components has the characteristics of difficult foaming of coated films, good glossiness, short surface drying time, etc.
Description
Water-dispersed polyisocyanic ester cross-linking agent of the present invention relates to a kind of linking agent, especially relates to a kind of water dispersible type polyurethane linking agent that is used for aqueous double-component polyurethane coating and preparation method thereof.
Traditional coating is based on solvent based coating, the discharging of the volatile organic compounds in the coating all is harmful to human body and environment, along with the enhancing of environmental consciousness and the foundation of environmental regulation, conventional solvent type coating more and more is restricted, therefore, the low water-borne coatings that pollutes environment-friendly type has become the direction of coating development; Simultaneously, oneself is applied water-borne coatings aspect a lot, but, only its film carry out crosslinking curing after, just can possess the film performance suitable with solvent based coating, as water tolerance, solvent resistance, chemical-resistant, wear resistance etc., so good and bad quality that directly influences coating of its linking agent crosslinking feature, the polyisocyanate crosslinking agent that uses in existing linking agent such as the solvent-borne type double-component polyurethane coating, no matter be that aromatic series or aliphatics and alicyclic isocyanate all are difficult to direct emulsification or are scattered in the water, in aqueous double-component polyurethane coating, to carry out chemical modification to it, by introducing the wetting ability that the hydrophilic functional group improves polymeric polyisocyanate, so that it is easy to emulsification or dispersion in water, thereby keep certain stability.U.S. Patent No. 4,433,095 has prepared aqueous dispersion type aromatic poly-isocyanate linking agent, U.S. Patent No. 4,633,377 have prepared aqueous dispersion type aliphatics alicyclic polymeric isocyanate linking agent, it all is to utilize the monoalky lether of isocyanate functional groups and many ethylene glycol monoalkyl ethers or many ethylene glycol and many propylene glycol copolymers to carry out chemical reaction and keep its wetting ability, above shortcoming one is that wetting ability is poor, unstable in water, often need to use relatively large organic solvent, dilute and to disperse as ethers and solvent of ether ester type; In addition, be solid owing to use many ethylene glycol monoalkyl ethers of higher molecular weight, also causing the polymeric polyisocyanate of modification is solid, causes the difficulty in the use.U.S. Patent No. 3,996,154 and English Patent No.1,417,618 and No.1,444,933 use many ethylene glycol monoalkyl ethers of lower molecular weight to be mainly used to modified aromatic adoption isocyanic ester, still, because the reaction of aromatic poly-isocyanate functional group and water is very fast, its carbonic acid gas of emitting very easily makes the foaming of filming, and it is unfavorable being used for aqueous polyurethane coating with bi component, can only be used for aqueous adhesive and use.U.S. Patent No. 5,200,489 and No.5,252, though 696 used low-molecular-weight many ethylene glycol monoalkyl ethers to come modified aliphatic and alicyclic polymeric isocyanate, because its viscosity is bigger, be scattered in the water difficult, poor with the water-based hydroxyl resin compatible, cause coating film gloss not high, and other film performance is not good.At above problem, the present invention has invented a kind of linking agent that is applicable to water-borne coatings in the influence factors such as suitable dispersion viscosity that take into full account the molecular weight size of many ethylene glycol monoalkyl ethers, add-on and gained modified polyisocyanate.
The objective of the invention is to: a kind of water-dispersed polyisocyanic ester cross-linking agent that is applicable to aqueous bi-component coating and preparation method thereof is provided, and this linking agent not only has good water dispersible, also has good film-forming properties in two-component coating.
Purpose of the present invention can be achieved through the following technical solutions: a kind of water-dispersed polyisocyanic ester cross-linking agent, comprise polymeric polyisocyanate, many ethylene glycol monoalkyl ethers, and characteristics are; The average isocyanate functionality of polymeric polyisocyanate is 2.5-5; The molecular weight of many ethylene glycol monoalkyl ethers is 300-800, and its add-on is the 10-25% of polymeric polyisocyanate weight, and wherein, alkyl can be methyl, ethyl, propyl group, butyl or its isomer; Organic thinner is aromatic hydrocarbon, ketone, ester, ether or ether-ether class organic solvent, or the mixture of above solvent different ratios, as toluene, dimethylbenzene, acetone, butanone, vinyl acetic monomer, N-BUTYL ACETATE, dipropylene glycol dme acetic ester, 1-Methoxy-2-propyl acetate etc., thinner accounts for the 10-50% of linking agent weight.It is suitable to make the present invention have viscosity, and dispersion effect is good in water, and is good with the water-based hydroxyl resin compatible, improves the characteristic of film performance.
On the technique scheme basis, polymeric polyisocyanate of the present invention comprises: the mixture of one or more in the biuret of di-isocyanate, isophorone diisocyanate, two cyclohexyl methane diisocyanates, tetramethylxylylene diisocyanate, dimer, tripolymer, the affixture.
On the technique scheme basis, water-dispersed polyisocyanic ester cross-linking agent preparation technology of the present invention is as follows: polymeric polyisocyanate and many ethylene glycol monoalkyl ethers two components are carried out chemical reaction to isocyanic acid content and are no longer changed under 30-100 ℃ of condition, in reaction, can add a little catalyzer, as dibutyl tin etc., question response is complete, adds thinner again and is mixed into the suitable linking agent of viscosity.
On the technique scheme basis, water-dispersed polyisocyanic ester cross-linking agent preparation technology of the present invention is as follows: after polymeric polyisocyanate, many ethylene glycol monoalkyl ethers and the mixing diluents, carry out under the 30-100 ℃ of condition till chemical reaction to isocyanic acid content no longer changes.
Superiority of the present invention is; Viscosity is suitable, and is good with water-compatible, and it is fast that the coating that product of the present invention and water-based hydroxyl resin Composition fit in has a difficult foaming of filming, high gloss, surface drying time, the easy characteristics of overcoating at short notice.
Describe in detail below by example.
Embodiment: the first step adds respectively in reactor: the polymeric polyisocyanate of 100 parts of weight, selecting 25 parts of weight molecular weights of IPDI tripolymer in the present embodiment for use is many ethylene glycol monobutyl ethers of 650 and a small amount of dibutyltin dilaurate catalyst.Second step stirred each component in the reactor, was warming up to 60 ℃, and reaction is about 4 hours under this temperature condition, add 75 parts of weight 1-Methoxy-2-propyl acetate dilution back discharging water-dispersed polyisocyanic ester cross-linking agent.
Application examples: be 35% at solid content, in the water-based hydroxyl polyurethane dispersion liquid of hydroxy radical content 1.5%, in NCO: OH=1.5: 1 ratio adds the water-dispersed polyisocyanic ester cross-linking agent for preparing in the foregoing description, manually stir, add entry and be diluted to the suitable viscosity of brushing, by the standard making sheet of People's Republic of China (PRC) man with carry out film performance and test, the result is as follows:
Appearance of film: smooth smooth
Gloss (60 °): 98 GB1743-79
Water-fast: 120 hours no change GB/T1733-93
Pencil hardness: 2H GB/T6739-1966
Wear-resisting (750g/500r): 10mg GB1768-79
Surface drying time 10min. GB6753.2-86
Claims (4)
1, a kind of water-dispersed polyisocyanic ester cross-linking agent comprises polymeric polyisocyanate, many ethylene glycol monoalkyl ethers, it is characterized in that: the average isocyanate functionality of polymeric polyisocyanate is 2.5-5; The molecular weight of many ethylene glycol monoalkyl ethers is 300-800, and its add-on is the 10-25% of polymeric polyisocyanate weight, and wherein, alkyl can be methyl, ethyl, propyl group, butyl or its isomer; Organic thinner has comprised aromatic hydrocarbon, ketone, ester, ether, ether-ether class organic solvent, and thinner accounts for the 10-50% of linking agent weight.
2, water-dispersed polyisocyanic ester cross-linking agent according to claim 1 is characterized in that: described polymeric polyisocyanate is one or more the mixture in the biuret, dimer, tripolymer, affixture of hexamethylene diisocyanate, isophorone diisocyanate, dicyclohexyl methane diisocyanate, tetramethylxylylene diisocyanate.
3, the preparation technology of water-dispersed polyisocyanic ester cross-linking agent according to claim 1 and 2, it is characterized in that: polymeric polyisocyanate and many ethylene glycol monoalkyl ethers two components are carried out chemical reaction to isocyanic acid content no longer change under 30-100 ℃ of condition, then, add thinner again.
4, the preparation technology of water-dispersed polyisocyanic ester cross-linking agent according to claim 1 and 2, it is characterized in that: after polymeric polyisocyanate, many ethylene glycol monoalkyl ethers and the mixing diluents, carrying out under the 30-100 ℃ of condition till chemical reaction to isocyanic acid content no longer changes.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB001169912A CN1138823C (en) | 2000-07-04 | 2000-07-04 | Water-dispersed polyisocyanic ester cross-linking agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB001169912A CN1138823C (en) | 2000-07-04 | 2000-07-04 | Water-dispersed polyisocyanic ester cross-linking agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1278537A CN1278537A (en) | 2001-01-03 |
| CN1138823C true CN1138823C (en) | 2004-02-18 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB001169912A Expired - Fee Related CN1138823C (en) | 2000-07-04 | 2000-07-04 | Water-dispersed polyisocyanic ester cross-linking agent |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1138823C (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101619128B (en) * | 2009-07-31 | 2011-12-21 | 中国科学院广州化学研究所 | Amido end-blocking non-ionic water-based isocyanate, preparation method and application thereof |
| CN106967229A (en) * | 2017-03-30 | 2017-07-21 | 广元瑞峰新材料有限公司 | A kind of preparation method of isocyanate-crosslinked accelerator |
| CN109467671B (en) * | 2017-09-08 | 2020-12-18 | 乐陵思盛聚合物材料有限公司 | Preparation of aqueous polyisocyanate curing agent |
| CN108587112A (en) * | 2018-04-13 | 2018-09-28 | 上海浩登材料股份有限公司 | A kind of aqueous aromatic polyisocyanate crosslinking agent and preparation method thereof |
-
2000
- 2000-07-04 CN CNB001169912A patent/CN1138823C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1278537A (en) | 2001-01-03 |
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