CN101844091B - Catalyst composite and application thereof in preparation of abietate - Google Patents
Catalyst composite and application thereof in preparation of abietate Download PDFInfo
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Abstract
The invention relates to a catalyst composite for preparing abietate and application thereof in the preparation of abietate. The catalyst composite comprises the following components in percentage by weight: first component: 0.01 to 2 percent of iodine and compound thereof; second component: 0.01 and 1 percent of iron powder and iron-contained compound and zinc powder and zinc-contained compound; third component: 97 to 99.98 percent of micromolecule organic compound for providing acitive hydrogen. When in use, the catalyst composite is reacted with rosin under the heating condition, and then distillation, esterification and the like are undertaken on the processed rosin. The color of the prepared abietate can reach water white, and the color and the heat stability of the prepared abietate are excellent.
Description
Technical field
The present invention relates to a kind of carbon monoxide-olefin polymeric and uses thereof, relate in particular to a kind of carbon monoxide-olefin polymeric that is used for preparing rosin ester and in the purposes of preparation rosin ester.
Background technology
Rosin be the inner rosin that flows out of pine tree trunk after steam distillation steams turpentine oil, the blocks of solid that obtains, its color is sallow dark red, is a kind of important chemical material.Rosin is by the mixture of various kinds of resin acid and the complicacy that little fat is sour, neutral substance is formed; It (mainly is the isomer of resin acid that acidic materials wherein account for about 90%; Also has little fat acid); Neutral substance accounts for 5%～10%, and it is formed also along with the place of production of rosin raw material is different with method for processing and different.Shortcomings such as but rosin has easy oxidation, is prone to crystallization, and color is dark are not generally directly used, and must be carried out deep processing.
Rosin ester is a kind of rosin deep processed product that is obtained with the alcohol reaction by rosin.It is of many uses, can be used as the tackifier of packaging material, pressure sensitive adhesive, PUR etc., the modifier of rubber and plastics, the setting agent of cosmetics etc.The color of rosin ester is the important technology index that determines its commercial survival ability with stability; The huge market demand of the high-quality rosin ester of of light color, good stability; At present domestic also difficulty meet the need of market; And such high-quality rosin ester product is many, and price is higher by Japan, U.S.'s import, the rosin ester of domestic production mostly can not color with stable two aspect take into account.
Summary of the invention
In order to overcome above-mentioned defective, the present invention provides a kind of carbon monoxide-olefin polymeric, comprises the component of following percetage by weight: first component: be selected from iodine and compound 0.01～2% thereof; Second component: chosen from Fe and compound thereof and zinc and compound 0.01～1% thereof; The 3rd component: be selected from the little molecular organic compound 97～99.98% that reactive hydrogen is provided.
Preferably, in first component be iodine.
Preferably, second component is iron powder or zinc powder.
First component is preferably iodine, and second component is preferably iron powder or zinc powder, and the adding of iron powder or zinc powder and iodine can promote the transfer of reactive hydrogen between little molecular organic compound that reactive hydrogen is provided and rosin acid synergistically.
Preferably, the granularity of iron powder or zinc powder is 50～200 orders in second component.
Preferably, the compound that contains iodine in first component is selected from KI, sodium iodide, ferric iodide and iodomethane.
Preferably, the iron containing compounds in second component is selected from ferric trichloride, triiodide iron, ferric bromide, and zinc compound is selected from zinc chloride, zinc iodide.
It is said that the little molecular organic compound of reactive hydrogen is provided is to contain the little molecular organic compound that adjoins the reactive hydrogen atom that one or more pairs of keys are arranged; Preferably be selected from acrylic acid, methacrylic acid, maleic acid, fumaric acid, rosin acid, citrene, 1, one or more in 4-cyclohexadiene and the terpinene.
Carbon monoxide-olefin polymeric of the present invention is used to prepare rosin ester, during use, and can be earlier with carbon monoxide-olefin polymeric of the present invention and the reaction down of rosin heating condition, steps such as the rosin after will handling then distills, esterification.The rosin ester color of preparing like this can reach water white; Through detecting its color (breathing out gloomy value) in 70～200 scopes; Softening point also is stabilized in about 100 ℃～104 ℃, and the rosin ester for preparing was worn out 8 as a child at 180 ℃ in ageing oven, and color (breathing out gloomy value) is also in 120～250 scopes; 400w ultraviolet ageing 15 hours, color (adding nanofarad) is between 1.5～2.It is thus clear that the rosin ester of carbon monoxide-olefin polymeric of the present invention preparation color and thermally-stabilised on excellent performance.
To combine embodiment to introduce carbon monoxide-olefin polymeric of the present invention and method for using thereof in detail below.
The specific embodiment
Embodiment 1
The four-hole boiling flask of 250ml is installed to electrical heating put, load onto agitating device, connect nitrogen ingress pipe, load onto thermometer and water knockout drum condenser pipe; Add 200 gram rosin, wait rosin to be warmed up to 200 ℃ after, add 0.02 gram iodine, 0.004 gram, 100 purpose iron powders; 10 gram citrenes stir, and are warmed up to 240 ℃; Insulation is 6 hours under this temperature, this treated rosin is distilled refiningly again, collects 190 ℃～245 ℃ cut.
The cut of collecting 150 grams are poured in another 250ml four-hole boiling flask, installed to electrical heating and put, load onto agitating device, connect nitrogen ingress pipe; Load onto thermometer and water knockout drum, wait rosin to be warmed up to 200 ℃ after, add 15 gram pentaerythrites, 0.45 gram, 300 (chemical names: 4; 4 '-thiobis (5-methyl-2-tert-butyl phenol), Guangzhou synthetic material research institute), stir; Be warmed up to 275 ℃, insulation is 6 hours under this temperature, stops reaction; Be cooled to 230 ℃ and add antioxidant 1010 (chemical name: four [β-(3, the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester), stir and pour out.Survey 106 ℃ of softening points, acid number 23, color (breathing out gloomy value) 100.180 ℃ were worn out color (breathing out gloomy value) 160 8 hours in ageing oven.400W ultraviolet ageing 15 hours, resin weightening finish 0.3%, No. 2 looks of color (adding nanofarad).
Embodiment 2
The four-hole boiling flask of 250ml is installed to electrical heating put, load onto agitating device, connect nitrogen ingress pipe, load onto thermometer and water knockout drum condenser pipe; Add 200 gram rosin, wait rosin to be warmed up to 200 ℃ after, add 0.02 gram KI, 0.02 gram ferric trichloride; 10 gram citrenes stir, and are warmed up to 240 ℃; Insulation is 6 hours under this temperature, this treated rosin is distilled refiningly again, collects 190 ℃～245 ℃ cut.
The cut of collecting 150 grams are poured in another 250ml four-hole boiling flask, installed to electrical heating and put, load onto agitating device, connect nitrogen ingress pipe; Load onto thermometer and water knockout drum, wait rosin to be warmed up to 200 ℃ after, add 15 gram pentaerythrites, 0.45 gram, 300 (chemical names: 4; 4 '-thiobis (5-methyl-2-tert-butyl phenol), Guangzhou synthetic material research institute), stir; Be warmed up to 275 ℃, insulation is 6 hours under this temperature, stops reaction; Be cooled to 230 ℃ and add antioxidant 1010 (chemical name: four [β-(3, the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester), stir and pour out.Survey 105 ℃ of softening points, acid number 22, color (breathing out gloomy value) 70.180 ℃ were worn out color (breathing out gloomy value) 120 8 hours in ageing oven.400W ultraviolet ageing 15 hours, resin weightening finish 0.25%, No. 1.8 looks of color (adding nanofarad).
Embodiment 3
The four-hole boiling flask of 250ml is installed to electrical heating put, load onto agitating device, connect nitrogen ingress pipe, load onto thermometer and water knockout drum condenser pipe; Add 200 gram rosin, wait rosin to be warmed up to 200 ℃ after, add 0.02 gram ferric iodide, 0.04 gram ferric bromide; 10 gram citrenes stir, and are warmed up to 240 ℃; Insulation is 6 hours under this temperature, this treated rosin is distilled refiningly again, collects 190 ℃～245 ℃ cut.
The cut of collecting 150 grams are poured in another 250ml four-hole boiling flask, installed to electrical heating and put, load onto agitating device, connect nitrogen ingress pipe; Load onto thermometer and water knockout drum, wait rosin to be warmed up to 200 ℃ after, add 15 gram pentaerythrites, 0.45 gram, 300 (chemical names: 4; 4 '-thiobis (5-methyl-2-tert-butyl phenol), Guangzhou synthetic material research institute), stir; Be warmed up to 275 ℃, insulation is 6 hours under this temperature, stops reaction; Be cooled to 230 ℃ and add antioxidant 1010 (chemical name: four [β-(3, the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester), stir and pour out.Survey 103 ℃ of softening points, acid number 20, color (breathing out gloomy value) 125.180 ℃ were worn out color (breathing out gloomy value) 200 8 hours in ageing oven.400W ultraviolet ageing 15 hours, resin weightening finish 0.35%, No. 2 looks of color (adding nanofarad).
Embodiment 4
The four-hole boiling flask of 250ml is installed to electrical heating put, load onto agitating device, connect nitrogen ingress pipe, load onto thermometer and water knockout drum condenser pipe; Add 200 gram rosin, wait rosin to be warmed up to 200 ℃ after, add 0.2 gram sodium iodide, 0.02 gram, 100 purpose zinc powders; 10 gram citrenes stir, and are warmed up to 240 ℃; Insulation is 6 hours under this temperature, this treated rosin is distilled refiningly again, collects 190 ℃～245 ℃ cut.
The cut of collecting 150 grams are poured in another 250ml four-hole boiling flask, installed to electrical heating and put, load onto agitating device, connect nitrogen ingress pipe; Load onto thermometer and water knockout drum, wait rosin to be warmed up to 200 ℃ after, add 15 gram pentaerythrites, 0.45 gram, 300 (chemical names: 4; 4 '-thiobis (5-methyl-2-tert-butyl phenol), Guangzhou synthetic material research institute), stir; Be warmed up to 275 ℃, insulation is 6 hours under this temperature, stops reaction; Be cooled to 230 ℃ and add antioxidant 1010 (chemical name: four [β-(3, the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester), stir and pour out.Survey 103 ℃ of softening points, acid number 23, color (breathing out gloomy value) 200.180 ℃ were worn out color (breathing out gloomy value) 250 8 hours in ageing oven.400W ultraviolet ageing 15 hours, resin weightening finish 0.38%, No. 2.5 looks of color (adding nanofarad).
Embodiment 5
The four-hole boiling flask of 250ml is installed to electrical heating put, load onto agitating device, connect nitrogen ingress pipe, load onto thermometer and water knockout drum condenser pipe; Add 200 gram rosin, wait rosin to be warmed up to 200 ℃ after, add 0.02 gram iodine, 0.02 gram, 100 purpose iron powders; 10 grams 1, the 4-cyclohexadiene stirs, and is warmed up to 240 ℃; Insulation is 6 hours under this temperature, this treated rosin is distilled refiningly again, collects 190 ℃～245 ℃ cut.
The cut of collecting 150 grams are poured in another 250ml four-hole boiling flask, installed to electrical heating and put, load onto agitating device, connect nitrogen ingress pipe; Load onto thermometer and water knockout drum, wait rosin to be warmed up to 200 ℃ after, add 15 gram pentaerythrites, 0.45 gram, 300 (chemical names: 4; 4 '-thiobis (5-methyl-2-tert-butyl phenol), Guangzhou synthetic material research institute), stir; Be warmed up to 275 ℃, insulation is 6 hours under this temperature, stops reaction; Be cooled to 230 ℃ and add antioxidant 1010 (chemical name: four [β-(3, the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester), stir and pour out.Survey 103 ℃ of softening points, acid number 23, color (breathing out gloomy value) 75.180 ℃ were worn out color (breathing out gloomy value) 120 8 hours in ageing oven.400W ultraviolet ageing 15 hours, resin weightening finish 0.24%, No. 1.5 looks of color (adding nanofarad).
Embodiment 6
The four-hole boiling flask of 250ml is installed to electrical heating put, load onto agitating device, connect nitrogen ingress pipe, load onto thermometer and water knockout drum condenser pipe; Add 200 gram rosin, wait rosin to be warmed up to 200 ℃ after, add 0.02 gram iodomethane, 0.02 gram zinc chloride; 5 grams 1, the 4-cyclohexadiene stirs, and is warmed up to 240 ℃; Insulation is 6 hours under this temperature, this treated rosin is distilled refiningly again, collects 190 ℃～245 ℃ cut.
The cut of collecting 150 grams are poured in another 250ml four-hole boiling flask, installed to electrical heating and put, load onto agitating device, connect nitrogen ingress pipe; Load onto thermometer and water knockout drum, wait rosin to be warmed up to 200 ℃ after, add 15 gram pentaerythrites, 0.45 gram, 300 (chemical names: 4; 4 '-thiobis (5-methyl-2-tert-butyl phenol), Guangzhou synthetic material research institute), stir; Be warmed up to 275 ℃, insulation is 6 hours under this temperature, stops reaction; Be cooled to 230 ℃ and add antioxidant 1010 (chemical name: four [β-(3, the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester), stir and pour out.Survey 103 ℃ of softening points, acid number 23, color (breathing out gloomy value) 90.180 ℃ were worn out color (breathing out gloomy value) 150 8 hours in ageing oven.400W ultraviolet ageing 15 hours, resin weightening finish 0.32%, No. 2 looks of color (adding nanofarad).
Embodiment 7
The four-hole boiling flask of 250ml is installed to electrical heating put, load onto agitating device, connect nitrogen ingress pipe, load onto thermometer and water knockout drum condenser pipe; Add 200 gram rosin, wait rosin to be warmed up to 200 ℃ after, add 0.0012 gram hydrogen iodide, 0.12 gram, 80 purpose zinc powders; 11.88 the gram fumaric acid stirs, and is warmed up to 240 ℃; Insulation is 6 hours under this temperature, this treated rosin is distilled refiningly again, collects 190 ℃～245 ℃ cut.
The cut of collecting 150 grams are poured in another 250ml four-hole boiling flask, installed to electrical heating and put, load onto agitating device, connect nitrogen ingress pipe; Load onto thermometer and water knockout drum, wait rosin to be warmed up to 200 ℃ after, add 15 gram pentaerythrites, 0.45 gram, 300 (chemical names: 4; 4 '-thiobis (5-methyl-2-tert-butyl phenol), Guangzhou synthetic material research institute), stir; Be warmed up to 275 ℃, insulation is 6 hours under this temperature, stops reaction; Be cooled to 230 ℃ and add antioxidant 1010 (chemical name: four [β-(3, the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester), stir and pour out.Survey 105 ℃ of softening points, acid number 22, color (breathing out gloomy value) 70.180 ℃ were worn out color (breathing out gloomy value) 125 8 hours in ageing oven.400W ultraviolet ageing 15 hours, resin weightening finish 0.26%, No. 1.9 looks of color (adding nanofarad).
Embodiment 8
The four-hole boiling flask of 250ml is installed to electrical heating put, load onto agitating device, connect nitrogen ingress pipe, load onto thermometer and water knockout drum condenser pipe; Add 200 gram rosin, wait rosin to be warmed up to 200 ℃ after, add 0.08 gram sodium iodide, 0.04 gram KI, 0.06 gram zinc iodide; 5 gram acrylic acid, 6.82 gram methacrylic acids stir, and are warmed up to 240 ℃; Insulation is 6 hours under this temperature, this treated rosin is distilled refiningly again, collects 190 ℃～245 ℃ cut.
The cut of collecting 150 grams are poured in another 250ml four-hole boiling flask, installed to electrical heating and put, load onto agitating device, connect nitrogen ingress pipe; Load onto thermometer and water knockout drum, wait rosin to be warmed up to 200 ℃ after, add 15 gram pentaerythrites, 0.45 gram, 300 (chemical names: 4; 4 '-thiobis (5-methyl-2-tert-butyl phenol), Guangzhou synthetic material research institute), stir; Be warmed up to 275 ℃, insulation is 6 hours under this temperature, stops reaction; Be cooled to 230 ℃ and add antioxidant 1010 (chemical name: four [β-(3, the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester), stir and pour out.Survey 103 ℃ of softening points, acid number 23, color (breathing out gloomy value) 75.180 ℃ were worn out color (breathing out gloomy value) 130 8 hours in ageing oven.400W ultraviolet ageing 15 hours, resin weightening finish 0.26%, No. 1.8 looks of color (adding nanofarad).
Embodiment 9
The four-hole boiling flask of 250ml is installed to electrical heating put, load onto agitating device, connect nitrogen ingress pipe; Load onto thermometer and water knockout drum condenser pipe, add 200 gram rosin, wait rosin to be warmed up to 200 ℃ after; Add 0.14 gram ferric iodide, 0.1 gram iodomethane, 0.002 gram, 80 purpose iron powders, 0.002 gram ferric bromide, 0.002 gram zinc chloride, 9.754 gram maleic acids, 2 gram terpinenes; Stir, be warmed up to 240 ℃, insulation is 6 hours under this temperature; Again this treated rosin is distilled refiningly, collect 190 ℃～245 ℃ cut.
The cut of collecting 150 grams are poured in another 250ml four-hole boiling flask, installed to electrical heating and put, load onto agitating device, connect nitrogen ingress pipe; Load onto thermometer and water knockout drum, wait rosin to be warmed up to 200 ℃ after, add 15 gram pentaerythrites, 0.45 gram, 300 (chemical names: 4; 4 '-thiobis (5-methyl-2-tert-butyl phenol), Guangzhou synthetic material research institute), stir; Be warmed up to 275 ℃, insulation is 6 hours under this temperature, stops reaction; Be cooled to 230 ℃ and add antioxidant 1010 (chemical name: four [β-(3, the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester), stir and pour out.Survey 103 ℃ of softening points, acid number 23, color (breathing out gloomy value) 150.180 ℃ were worn out color (breathing out gloomy value) 150 8 hours in ageing oven.400W ultraviolet ageing 15 hours, resin weightening finish 0.32%, No. 2.2 looks of color (adding nanofarad).
Comparing embodiment
The four-hole boiling flask of 250ml is installed to electrical heating put, load onto agitating device, connect nitrogen ingress pipe, load onto thermometer and water knockout drum condenser pipe, add 200 gram rosin, then rosin is distilled refiningly, collect 190 ℃～245 ℃ cut.
The cut of collecting 150 grams are poured in another 250ml four-hole boiling flask, installed to electrical heating and put, load onto agitating device, connect nitrogen ingress pipe; Load onto thermometer and water knockout drum, wait rosin to be warmed up to 200 ℃ after, add 15 gram pentaerythrites, 0.45 gram, 300 (chemical names: 4; 4 '-thiobis (5-methyl-2-tert-butyl phenol), Guangzhou synthetic material research institute), stir; Be warmed up to 275 ℃, insulation is 6 hours under this temperature, stops reaction; Be cooled to 230 ℃ and add antioxidant 1010 (chemical name: four [β-(3, the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester), stir and pour out.Survey 103 ℃ of softening points, acid number 23, color (breathing out gloomy value) 200.180 ℃ were worn out No. 2 looks of color (adding nanofarad) 8 hours in ageing oven.400W ultraviolet ageing 15 hours, resin weightening finish 0.8%, No. 4 looks of color (adding nanofarad).
Analyze: can find out from the foregoing description, adopt the rosin ester color of preparing after the catalyst combination processing of invention can reach water white, through detecting its color (breathing out gloomy value) in 70～200 scopes; Softening point also is stabilized in about 100 ℃～104 ℃; With the rosin ester of preparation 180 ℃ in ageing oven aging 8 as a child, color (breathing out gloomy value) also in 120～250 scopes, 400w ultraviolet ageing 15 hours; Color (adding nanofarad) is between 1.5～2, between the resin weightening finish 0.25～0.38%.It is thus clear that the rosin ester of carbon monoxide-olefin polymeric of the present invention preparation color and thermally-stabilised on excellent performance.And in the comparative example, rosin is without the processing of carbon monoxide-olefin polymeric of the present invention, and according to the one-tenth rosin ester of similar preparation method's preparation, its color dark (breathing out gloomy value) 200,180 ℃ wore out 8 hours in ageing oven, and color (adding nanofarad) is No. 2 looks.400W ultraviolet ageing 15 hours, resin weightening finish 0.8%, color (adding nanofarad) reaches look No. 4, and visible its heat endurance is relatively poor, the requirement that does not reach high-quality water-white rosin ester fully.Rosin ester through the rosin after the carbon monoxide-olefin polymeric processing of the present invention is prepared is all more excellent on color and thermal stability.
The above is merely preferred embodiment of the present invention, and is in order to restriction the present invention, not all within spirit of the present invention and principle, any modification of being done, is equal to replacement, improvement etc., all should be included within protection scope of the present invention.
Claims (1)
1. method for preparing rosin ester is characterized in that concrete preparation process is following: the four-hole boiling flask of 250ml is installed to electrical heating put, load onto agitating device; Connect nitrogen ingress pipe, load onto thermometer and water knockout drum condenser pipe, add 200 gram rosin; After rosin is warmed up to 200 ℃, add 0.02 gram iodine, 0.004 gram, 100 purpose iron powders; 10 gram citrenes stir, and are warmed up to 240 ℃; Insulation is 6 hours under this temperature, this treated rosin is distilled refiningly again, collects 190 ℃～245 ℃ cut;
The cut of collecting 150 grams are poured in another 250ml four-hole boiling flask, installed to electrical heating and put, load onto agitating device, connect nitrogen ingress pipe; Load onto thermometer and water knockout drum, wait rosin to be warmed up to 200 ℃ after, add 15 gram pentaerythrites, 0.45 gram Guangzhou synthetic material research institute produce 4; 4 '-thiobis (5-methyl-2-tert-butyl phenol) stirs, and is warmed up to 275 ℃, and insulation is 6 hours under this temperature; Stop reaction, be cooled to 230 ℃ and add antioxidant four [β-(3, the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester, stir and pour out; Survey 106 ℃ of softening points, acid number 23, color is breathed out gloomy value and in ageing oven, was worn out 8 hours for 100,180 ℃; Color is breathed out gloomy value 160,400W ultraviolet ageing 15 hours, and resin weightening finish 0.3%, adding the nanofarad color is No. 2 looks.
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| CN111393996B (en) * | 2020-04-21 | 2022-02-15 | 广东科茂林产化工股份有限公司 | Polymerized rosin mixed ester and preparation method and application thereof |
| CN113292927B (en) * | 2021-05-31 | 2022-08-30 | 江西金安林产实业有限公司 | Rosin resin for moisture-curing reactive hot melt adhesive and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4481145A (en) * | 1982-02-01 | 1984-11-06 | Enichem Elastomers Limited | Disproportionation of unsaturated acids |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4481145A (en) * | 1982-02-01 | 1984-11-06 | Enichem Elastomers Limited | Disproportionation of unsaturated acids |
Non-Patent Citations (1)
| Title |
|---|
| 夏建陵等."丙烯酸改性松香基环氧树脂的合成研究".《林产化学与工业》.2002,第22卷(第3期),第15页第1段. |
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Effective date of registration: 20190903 Address after: 510650 Room 2806, 89 Yanling Road, Tianhe District, Guangzhou City, Guangdong Province Patentee after: Guangzhou Yingke New Material Co., Ltd. Address before: High tech Zone 526238 in Guangdong province Zhaoqing City Yingbin Avenue south side of the bridge is gang Co-patentee before: Jiangxi Jin'an Forestry Industrial Co., Ltd. Patentee before: Guangdong Komo Co., Ltd. Co-patentee before: Guangzhou Yingke New Material Co., Ltd. |