CN101628965B - Polyisocyanate blocked prepolymer, urethane foam and both preparation methods thereof - Google Patents
Polyisocyanate blocked prepolymer, urethane foam and both preparation methods thereof Download PDFInfo
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- CN101628965B CN101628965B CN 200910091446 CN200910091446A CN101628965B CN 101628965 B CN101628965 B CN 101628965B CN 200910091446 CN200910091446 CN 200910091446 CN 200910091446 A CN200910091446 A CN 200910091446A CN 101628965 B CN101628965 B CN 101628965B
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Abstract
The invention discloses a polyisocyanate blocked prepolymer, urethane soft foam containing the same and both preparation methods thereof, wherein the functionality degree of the prepolymer is 2.05-2.32, the dissociated NCO content is 24.0-37.9 percent by weight; and the soft foam prepared by using the prepolymer has favorable ball resilience and mechanical property as well as excellent damp-heat resistant performance and processing characteristics.
Description
Technical field
The present invention relates to a kind of polyisocyanate blocked prepolymer, and contain the urethane foam of described polyisocyanate blocked prepolymer and their preparation method.
Background technology
As everyone knows, tolylene diisocyanate belongs to the hazardous substance compound, and vapour pressure is lower, and irritating smell is arranged, and easily human body and surrounding environment is polluted and destroys.Country is to the production of tolylene diisocyanate, and transportation and storage all have very strict security regulations.This has brought inconvenience also for the production and the use of tolylene diisocyanate.And the molecular weight of two phenyl ring and higher phenyl ring isocyanic ester is relatively large, and the harm of the higher environment to human body of vapour pressure is less, produces and uses also comparatively conveniently, so the isocyanate prepolymer of MDI and MT system obtains the attention of each enterprise and research and development institution.
Based on the mixture of diphenylmethanediisocyanate, poly methylene poly phenyl poly isocyanate and tolylene diisocyanate, and known and describe in the prior art based on the prepolymer of these mixtures.Use these based on the vulcabond of MDI and the mixture of polymeric MDI or PMDI in the prior art, and also be known based on the method that the prepolymer of middle mixture is made flexible polyurethane foam.
For example United States Patent (USP) 5132334, and the isocyanate mixture of employing prepares polyurethane foam, and its isocyanic ester is formed and comprised: the tolylene diisocyanate of 21-95wt%; The diphenylmethanediisocyanate of 5-79%, wherein the content of 2,4 ' body is 8-30wt% among the MDI, the content of 4,4 ' body is 45-87wt%, and contains 2,2 ' body less than 4wt%; The content of poly methylene poly phenyl poly isocyanate is 5-35%.The content of the tolylene diisocyanate of this mixture is higher, reach as high as 95wt%, and in the general defined MT system content of tolylene diisocyanate all less than 50wt%, this technology only is the mixing of several isocyanic ester, do not carry out prepolymerization reaction with multicomponent alcoholics compound, and the pre-polymerization of polyvalent alcohol and part isocyanic ester helps improving the low-temperature storage of isocyanic ester, improves the process tolerance when using, and can also obviously improve every physicals of the polyurethane products of making.
US4256849 has described a kind of miscellany of isocyanic ester, wherein contains 4,4 of 60-90wt% '-MDI, 2,4 of 3-30wt% '-MDI, and the content of tolylene diisocyanate is less than 20wt%.
Chinese patent ZL01813351.7,4,4 of use 66-99wt% '-; 2,4 '-; With 2,2 '-diphenylmethanediisocyanate and more the poly methylene poly phenyl poly isocyanate of high functionality be a component and other two components (TDI and combined polyether) prepared in reaction polyurethane flexible foam; In the MDI series isocyanates composition 4,4 '-MDI content is 51-87wt%, 2,4 '-MDI content is less than 16wt%, 2,2 '-MDI content is less than 5wt%.
And US4256849 and Chinese patent ZL01813351.7 do not relate to the pre-polymerization of polyvalent alcohol and isocyanic ester yet.
United States Patent (USP) 5436277 uses polyvalent alcohol and isocyanic ester to carry out pre-polymerization, and the TDI that consists of 7-13wt% of its performed polymer, 2.4 of 17-27wt% '-MDI, 4,4 of 55-75wt% '-MDI, three rings reach more that epipodium isocyanate compound content is 1-25wt%.With the molecular weight 500-10000 of the polyvalent alcohol of isocyanic ester pre-polymerization, functionality 1.5-4, hydroxyl value 25-85mgK0H/g, finally obtain with polymers NCO% be 20-40%.But with the oxygen ethylidene of the polyvalent alcohol of isocyanic ester pre-polymerization and the different performances to process tolerance and final foam article of oxygen propylidene content very significantly influence is arranged, this is that United States Patent (USP) 5436277 is ignored.
China Patent No. ZL95121757.7 discloses a kind of employing low-unsaturation-degree polyether and modified isocyanate component, and preparation has the polyurethane foam of good rebound resilience and tension set.Its modified isocyanate partly comprises the TDI of 3-20%; 80-97%MDI series isocyanates (two ring content 60-80%); And generate semi-prepolymer: functionality 2-4, molecular weight 2000-10000, EO/PO ratio 50/50-80/20 with following polyether reactant.But single polyethers of high EO content that uses makes the special perforate of foam easily in this polyisocyanates performed polymer, the foam wild effects such as the numb skin of bubble that occur easily collapsing; The polyethers of high in addition EO content also has considerable influence to the foam mechanical property.
Summary of the invention
At above technological deficiency, the invention provides a kind of polyisocyanate blocked prepolymer, and contain the urethane foam of described polyisocyanate blocked prepolymer and their preparation method.
Polyisocyanate blocked prepolymer of the present invention, its functionality are 2.05-2.32, and free NCO content is 24.0-37.9wt%,
And described prepolymer in prepolymer quality percentage composition, is mainly generated by following component reaction:
The tolylene diisocyanate of 3-30%;
The diphenylmethanediisocyanate of 42.2-87%;
The tricyclic antidepressants isocyanic ester of 3.8-17%;
The above kind isocyanate of three rings of 3.7-12.5%; With
The polyvalent alcohol of 1-20%; Selectively and
The carbodiimide of 0.5-20%/urine ketoimine modified isocyanate.
In the polyisocyanate blocked prepolymer of the present invention, in the described diphenylmethanediisocyanate, in mass, contain 2 of 0-5%, 2 '-diphenylmethanediisocyanate, 4 of 22.5-79.6%, 4 '-diphenylmethanediisocyanate, 2 of 0-39.6%, 4 '-diphenylmethanediisocyanate.
In the further preferred described diphenylmethanediisocyanate of the present invention, 2,4 '-diphenylmethanediisocyanate and 4, the mass ratio 2 of 4 '-diphenylmethanediisocyanate: 98-50: 50.
As embodiment preferred, in the described diphenylmethanediisocyanate, in mass, contain 2 of 0-1%, 2 '-diphenylmethanediisocyanate, 4 of 35.8-63.5%, 4 '-diphenylmethanediisocyanate, 2 of 1-25.2%, 4 '-diphenylmethanediisocyanate.
In the polyisocyanate blocked prepolymer of the present invention, contain 2,4 toluene diisocyanate and 2 in the described tolylene diisocyanate, the 6-tolylene diisocyanate, and 2,4 toluene diisocyanate and 2, the weight ratio of 6-tolylene diisocyanate are 98: 2-70: 30.
In the polyisocyanate blocked prepolymer of the present invention, as embodiment preferred, the weight ratio of described tricyclic antidepressants isocyanic ester and the above kind isocyanate of three rings is 1.2-18: 1.
Tricyclic antidepressants isocyanic ester described in the present invention mainly is meant dimethylene trimethylphenyl triisocyanate; The above kind isocyanate of three rings mainly is meant four phenyl ring and above isocyanic ester, and it does not comprise the tricyclic antidepressants isocyanic ester.
In the polyisocyanate blocked prepolymer of the present invention, described polyvalent alcohol can be for the polyvalent alcohol of this area routine, and as embodiment preferred, described polyvalent alcohol is polyvalent alcohol A, or the combination of polyvalent alcohol A and polyvalent alcohol B, wherein,
Polyvalent alcohol A: containing the initiator functionality is 2-5, and oxygen ethylidene amount is 60-100wt%, and molecular-weight average is 2000-10000, and equivalent is 450-5000, and hydroxyl value is 10-189mgKOH/g;
Polyvalent alcohol B: the initiator functionality that contains is 2-5, and oxygen ethylidene amount is 0-30wt%, and molecular-weight average is 2000-10000, and equivalent is 450-5000, and hydroxyl value is 10-189mgKOH/g.
Among the present invention, but when the raw material of carbodiimide/urine ketoimine modified isocyanate was used in the preparation of the polyisocyanate blocked prepolymer of the present invention, preferably containing carbodiimide/urine ketoimine functional group content in the polyisocyanate blocked prepolymer that makes at last was 0.5-10wt%.
When invention adopts above-mentioned raw materials to prepare polyisocyanate blocked prepolymer, described method comprises: diphenylmethanediisocyanate and polyvalent alcohol were expected 80 ℃ of temperature stirring reaction 1-2 hour in reactor, add tolylene diisocyanate, tricyclic antidepressants isocyanic ester and the above kind isocyanate of three rings then, selectively and carbodiimide/urine ketoimine modified isocyanate, restir mixing 0.5-1 hour gets polyisocyanate blocked prepolymer.
The invention still further relates to a kind of flexible foam body that contains described polyisocyanate blocked prepolymer, wherein, described foams are made by following raw material:
The polyisocyanate blocked prepolymer of 30-75 weight part;
The polyvalent alcohol C of part of 100 weight, molecular-weight average is 4800, and functionality is 3 oxyethane propylene oxide based polyether polyol, and wherein the EO/P0 ratio is 15/85, hydroxyl value 35mgKOH/g;
0.1-3.0 parts by weight of cross-linking agent;
2.0-15 the chemical foaming agent of weight part or pneumatogen;
0.1-2.0 the tensio-active agent of weight part; With
0.1-2.0 the catalyzer of weight part.
Wherein, described linking agent can be linking agent, tensio-active agent, the catalyzer of this area routine, and described linking agent includes but not limited to alcamines linking agent for example diethanolamine, trolamine, amine linking agent Wannate 6200 etc.; Whipping agent is preferably water; Described tensio-active agent comprises but is not limited to silicone tensio-active agent such as dimethyl silicone oil; Described catalyzer comprises but is not limited to amine catalyst, as triethylenediamine, and containing metal class catalyzer such as dibutyl tin laurate, stannous octoate etc.
Foam software of the present invention can adopt the method for this area routine to be prepared, for example include but not limited to adopt the moulding technology of cold-curing, wherein die temperature is 40-80 ℃, preferred 50-60 ℃ temperature, foam solidified 2-10 minute therein, foams slaking at normal temperatures 1 hour to 2 days usually promptly gets foam software of the present invention after the demoulding.
TDI content is 3-30wt% in the polyisocyanate blocked prepolymer of the present invention, meets the standard of MT, therefore has the feature of environmental protection preferably.Simultaneously, the existing good perforate of foams of the present invention, ball resilience and mechanical property, excellent wet-hot aging performance and processes characteristic; Avoided foamy in the technological process to shrink and the roll extrusion process in cracking; Guaranteed foamy stability again, the foam phenomenons such as the numb skin of bubble that are not easy to occur collapsing; Also can not have influence on the foamy physicals, guarantee the foamy quality.
The polyisocyanate blocked prepolymer of the present invention, and the urethane foam that contains described polyisocyanate blocked prepolymer is specially adapted to have in automobile, the furniture the high rebound foam body of certain supporting capacity.
Embodiment
Now further the present invention will be described by following examples, but the present invention is not limited to therewith.
The raw material that following examples 1-10 adopted is specific as follows:
Polyol A: molecular-weight average is 5000, and functionality is 3 oxyethane propylene oxide based polyether polyol, and wherein the EO/P0 ratio is 75/25, hydroxyl value 34mgKOH/g;
Polyol B: molecular-weight average is 6000, and functionality is 3 oxyethane propylene oxide based polyether polyol, and wherein the EO/P0 ratio is 15/85, hydroxyl value 28mgKOH/g;
Polyol C: molecular-weight average is 4800, and functionality is 3 oxyethane propylene oxide based polyether polyol, and wherein the EO/P0 ratio is 15/85, hydroxyl value 35mgKOH/g;
Linking agent: diethanolamine (DEOA);
Whipping agent: deionized water;
Tensio-active agent: the silicone tensio-active agent that L3002 Mai Tu company produces;
Catalyzer: compound Ammonia catalyzer, autogamy is two (2-dimethylamino ethyl) ether of 0.3 weight part triethylene diamine and 0.15 weight part,
The preparation of the prepolymer that embodiment 1-5 is isocyanate-terminated
Embodiment 1-5 adopts following method to be prepared isocyanate-terminated prepolymer: when carrying out about 2 hours reaction end according to the represented adding tolylene diisocyanate of table 1, polyethers A, polyethers B under 80 ℃, the isocyanic ester and the tolylene diisocyanate that add dimethylene trimethylphenyl triisocyanate, four phenyl ring and above isocyanic ester, carbodiimide/urine ketoimine modification react promptly again, and it is specifically formed and NCO% sees the following form 1.
The prepolymer that table 1 is isocyanate-terminated
| Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 | Embodiment 5 | |
| Numbering | Prepolymer 1 | Prepolymer 2 | Prepolymer 3 | Prepolymer 4 | Prepolymer 5 |
| 4,4 ' diphenylmethanediisocyanate | 31.9 | 48.5 | 23.7 | ?60.5 | 41.2 |
| 2,4 ' diphenylmethanediisocyanate | 23.3 | 25.6 | 11.5 | ?0.6 | 15.2 |
| Dimethylene trimethylphenyl triisocyanate | 5.6 | 4.2 | 11.4 | ?3.9 | 5.2 |
| Four phenyl ring and above isocyanic ester | 5.0 | 3.8 | 7.2 | ?4.0 | 4.4 |
| Carbodiimide/urine ketoimine functional group content | 1.2 | 0.9 | 2.2 | ?1.1 | 6.0 |
| Tolylene diisocyanate (2, the 4-body: 2,6-body=80: 20) | 25.0 | 5.0 | 30.0 | ?15.0 | 18.0 |
| Polyol?A | 8.0 | 3.0 | 1.0 | ?3.0 | 5.0 |
| Polyol?B | 0 | 9.0 | 14.0 | ?9.0 | 5.0 |
| NCO％ | 33.83 | 29.54 | 31.82 | ?31.01 | 31.04 |
The preparation of embodiment 5-10 flexible foam body
Embodiment 5-10 adopts as the material in the table 2 and adopt following method to prepare, the moulding technology of cold-curing, and wherein die temperature is at 55 ℃, and foam solidified 4 minutes therein, slaking 2 days under the foams normal temperature after the demoulding.The performance of gained soft mould foamed plastic sees Table 2, and the detection method of its various performance index is as shown in table 3.
The foaming properties that table 2 isocyanate prepolymer makes
| Numbering | Embodiment-6 | Embodiment-7 | Embodiment-8 | Embodiment-9 | Embodiment-10 |
| Polyol?C | 100 | 100 | 100 | 100 | 100 |
| Deionized water | 3.5 | 3.5 | 3.5 | 3.5 | 3.5 |
| DEOA | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 |
| L3002 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 |
| Triethylene diamine | 0.3 | 0.3 | 0.3 | 0.3 | 0.3 |
| Two (2-dimethylamino ethyl) ether | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 |
| ISO | Prepolymer-1 | Prepolymer-2 | Prepolymer-3 | Prepolymer-4 | Prepolymer-5 |
| Index | 100 | 100 | 100 | 100 | 100 |
| The ratio of all the other components in prepolymer and the raw material | 0.55 | 0.62 | 0.59 | 0.59 | 0.60 |
| Tensile strength, KPa | 104 | 147 | 126 | 118 | 113 |
| Tear strength, N/cm | 2.15 | 2.86 | 1.62 | 3.20 | 1.98 |
| Elongation at break, % | 97.6 | 121.9 | 100.4 | 101.5 | 95.2 |
| Core density, kg/m 3 | 49.4 | 52.0 | 47.4 | 51.0 | 48.7 |
| CLD40％，KPa | 4.0 | 5.5 | 4.1 | 5.5 | 4.0 |
| Ball resilience (25 ℃), % | 65 | 60 | 67 | 60 | 64 |
| Dry compression deformation, % | 2.69％ | 5.24％ | 3.00％ | 4.26％ | 3.73％ |
| Wet compression deformation, % | 7.80％ | 9.48％ | 11.69％ | 5.62％ | 11.76％ |
As can be seen from Table 2, the foam that uses prepolymer of the present invention to make has good ball resilience and mechanical property, excellent wet-hot aging performance and processes characteristic.
Table 3 foam physics performance test methods
| Physicals | Unit | Testing standard |
| Density | kg/m3 | ISO?845 |
| CLD?40％ | kPa | ISO?3386 |
| Ball resilience (25 ℃) | ％ | ISO?8307 |
| Tensile strength | KPa | ISO?1798 |
| Elongation at break | ％ | ISO?1798 |
| Tear strength | N/cm | ISO?8067 |
| Dry compression deformation | ％ | ASTM?3574 |
| Wet compression deformation | ％ | ASTM?3574 |
Claims (9)
1. a polyisocyanate blocked prepolymer is characterized in that, the functionality of described prepolymer is 2.05-2.32, and free NCO content is 24.0-37.9wt%, and described prepolymer in the quality percentage composition of prepolymer, is mainly generated by following component reaction:
The tolylene diisocyanate of 3-30%;
The diphenylmethanediisocyanate of 42.2-87%;
The tricyclic antidepressants isocyanic ester of 3.8-17%;
The above isocyanic ester of four phenyl ring of 3.7-12.5%; With
The polyvalent alcohol of 1-20%; Selectively and
The carbodiimide of 0.5-20%/urine ketoimine modified isocyanate,
Described polyvalent alcohol is the combination of polyvalent alcohol A and polyvalent alcohol B, wherein,
Polyvalent alcohol A: containing the initiator functionality is 2-5, and oxygen ethylidene amount is 60-100wt%, and molecular-weight average is 2000-10000, and equivalent is 450-5000, and hydroxyl value is 10-189mgKOH/g;
Polyvalent alcohol B: the initiator functionality that contains is 2-5, and oxygen ethylidene amount is 0-30wt%, and molecular-weight average is 2000-10000, and equivalent is 450-5000, and hydroxyl value is 10-189mgKOH/g.
2. polyisocyanate blocked prepolymer according to claim 1, it is characterized in that, in the described diphenylmethanediisocyanate, in mass, contain 2 of 0-5%, 2 '-diphenylmethanediisocyanate, 4 of 22.5-79.6%, 4 '-diphenylmethanediisocyanate, 2 of 0-39.6%, 4 '-diphenylmethanediisocyanate.
3. polyisocyanate blocked prepolymer according to claim 2 is characterized in that, in the described diphenylmethanediisocyanate, and 2,4 '-diphenylmethanediisocyanate and 4, the weight ratio 2 of 4 '-diphenylmethanediisocyanate: 98-50: 50.
4. polyisocyanate blocked prepolymer according to claim 3, it is characterized in that, in the described diphenylmethanediisocyanate, in mass, contain 2 of 0-1%, 2 '-diphenylmethanediisocyanate, 4 of 35.8-63.5%, 4 '-diphenylmethanediisocyanate, 2 of 1-25.2%, 4 '-diphenylmethanediisocyanate.
5. polyisocyanate blocked prepolymer according to claim 4 is characterized in that, contains 2 in the described tolylene diisocyanate, 4-tolylene diisocyanate and 2, the 6-tolylene diisocyanate, and 2,4-tolylene diisocyanate and 2, the mass ratio of 6-tolylene diisocyanate are 98/2-70/30.
6. polyisocyanate blocked prepolymer according to claim 5 is characterized in that, the weight ratio of described tricyclic antidepressants isocyanic ester and the above isocyanic ester of four phenyl ring is 1.2-18: 1.
7. the preparation method of the arbitrary described polyisocyanate blocked prepolymer of claim 1-6, it is characterized in that, described method comprises: diphenylmethanediisocyanate and polyvalent alcohol were expected 80 ℃ of temperature stirring reaction 1-2 hour in reactor, add tolylene diisocyanate, tricyclic antidepressants isocyanic ester and the above isocyanic ester of four phenyl ring then, selectively and carbodiimide/urine ketoimine modified isocyanate, restir mixing 0.5-1 hour promptly gets polyisocyanate blocked prepolymer.
8. flexible foam body that contains the arbitrary described polyisocyanate blocked prepolymer of claim 1-6 is characterized in that described foams are made by following raw material:
The polyisocyanate blocked prepolymer of 30-75 weight part;
The polyvalent alcohol C of part of 100 weight, its molecular-weight average is 4800, and functionality is 3 oxyethane propylene oxide based polyether polyol, and wherein the EO/P0 ratio is 15/85, hydroxyl value 35mgKOH/g;
0.1-3.0 parts by weight of cross-linking agent;
2.0-15 the chemical foaming agent of weight part or pneumatogen;
0.1-2.0 the tensio-active agent of weight part; With
0.1-2.0 the catalyzer of weight part.
9. flexible foam body according to claim 8 is characterized in that, described linking agent is diethanolamine, trolamine or other amine linking agents; Tensio-active agent is the silicone tensio-active agent; Catalyzer is amine, metallic tin catalyst or bismuth metal class catalyzer.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102618019B (en) * | 2012-03-22 | 2014-04-16 | 万华化学（北京）有限公司 | Polyurethane reaction ball and preparing method thereof |
| CN105968311A (en) * | 2016-07-21 | 2016-09-28 | 淄博德信联邦化学工业有限公司 | Polyurethane flower mud and preparation method thereof |
| CN115044014A (en) * | 2022-05-16 | 2022-09-13 | 上海抚佳精细化工有限公司 | Toluene diisocyanate prepolymer and preparation method and application thereof |
| CN115558081A (en) * | 2022-10-31 | 2023-01-03 | 惠州永兴泰服装配件有限公司 | Production process of MDI sponge |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5436277A (en) * | 1994-07-28 | 1995-07-25 | Basf Corporation | Polyisocyanate compositions for the preparation of flexible polyurethane foams |
| CN1132759A (en) * | 1994-12-08 | 1996-10-09 | 三井东压化学株式会社 | Flexible high resilience polyurethane foam |
| CN1444611A (en) * | 2000-08-01 | 2003-09-24 | 亨茨曼国际有限公司 | Manufacture of MDI-TDI based flexible polyurethane foams |
-
2009
- 2009-08-21 CN CN 200910091446 patent/CN101628965B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5436277A (en) * | 1994-07-28 | 1995-07-25 | Basf Corporation | Polyisocyanate compositions for the preparation of flexible polyurethane foams |
| CN1132759A (en) * | 1994-12-08 | 1996-10-09 | 三井东压化学株式会社 | Flexible high resilience polyurethane foam |
| CN1444611A (en) * | 2000-08-01 | 2003-09-24 | 亨茨曼国际有限公司 | Manufacture of MDI-TDI based flexible polyurethane foams |
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Address after: 102200 No. 5 Spark Street, Changping science and Technology Park, Beijing Patentee after: Wanhua chemical (Beijing) Co., Ltd. Patentee after: wanhua Synthetic Leather Group Co., Ltd., Yantai Patentee after: Wanhua Chemical Group Co., Ltd. Address before: 102200, Beijing, Changping science and Technology Park Spark Street, No. 5, Beijing poly chemical new material Co., Ltd. Patentee before: Keju Chemical New Material Co., Ltd., Beijing Patentee before: wanhua Synthetic Leather Group Co., Ltd., Yantai Patentee before: Wanhua Chemical Group Co., Ltd. |
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| C41 | Transfer of patent application or patent right or utility model | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20160520 Address after: 102200, Beijing, Changping science and Technology Park Spark Street, No. 5, Beijing poly chemical new material Co., Ltd. Patentee after: Wanhua chemical (Beijing) Co., Ltd. Patentee after: Wanhua Chemical Group Co., Ltd. Address before: 102200, Beijing, Changping science and Technology Park Spark Street, No. 5, Beijing poly chemical new material Co., Ltd. Patentee before: Wanhua chemical (Beijing) Co., Ltd. Patentee before: wanhua Synthetic Leather Group Co., Ltd., Yantai Patentee before: Wanhua Chemical Group Co., Ltd. |