CN102443108A - Preparation method of low-density polyethylene with epoxy functional group on branched chain - Google Patents
Preparation method of low-density polyethylene with epoxy functional group on branched chain Download PDFInfo
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- CN102443108A CN102443108A CN2011102781971A CN201110278197A CN102443108A CN 102443108 A CN102443108 A CN 102443108A CN 2011102781971 A CN2011102781971 A CN 2011102781971A CN 201110278197 A CN201110278197 A CN 201110278197A CN 102443108 A CN102443108 A CN 102443108A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 27
- 229920001684 low density polyethylene Polymers 0.000 title claims abstract 14
- 239000004702 low-density polyethylene Substances 0.000 title claims abstract 14
- 239000004593 Epoxy Substances 0.000 title abstract description 5
- 125000000524 functional group Chemical group 0.000 title abstract 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 16
- 230000008961 swelling Effects 0.000 claims abstract description 12
- 239000000843 powder Substances 0.000 claims abstract description 10
- 238000003756 stirring Methods 0.000 claims abstract description 8
- 238000001035 drying Methods 0.000 claims abstract description 6
- 238000000967 suction filtration Methods 0.000 claims abstract description 6
- 239000000725 suspension Substances 0.000 claims abstract description 6
- 238000005406 washing Methods 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000004132 cross linking Methods 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 7
- 238000001556 precipitation Methods 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims description 5
- 238000010792 warming Methods 0.000 claims description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 10
- 238000010438 heat treatment Methods 0.000 abstract description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract description 3
- -1 polyethylene Polymers 0.000 abstract description 3
- CUGZWHZWSVUSBE-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxy)ethanol Chemical compound OCCOCC1CO1 CUGZWHZWSVUSBE-UHFFFAOYSA-N 0.000 abstract 3
- 239000004698 Polyethylene Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 229920000573 polyethylene Polymers 0.000 abstract 1
- 239000012716 precipitator Substances 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 13
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 150000002924 oxiranes Chemical group 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- YLLIGHVCTUPGEH-UHFFFAOYSA-M potassium;ethanol;hydroxide Chemical compound [OH-].[K+].CCO YLLIGHVCTUPGEH-UHFFFAOYSA-M 0.000 description 2
- 238000004513 sizing Methods 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 239000004634 thermosetting polymer Substances 0.000 description 2
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- HPOKESDSMZRZLC-UHFFFAOYSA-N propan-2-one;hydrochloride Chemical compound Cl.CC(C)=O HPOKESDSMZRZLC-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Abstract
The invention discloses a preparation method of low density polyethylene with epoxy functional groups on branched chains, which uses polyethylene grafted maleic anhydride (LDPE-g-MAH) and ethylene glycol glycidyl ether (EGDE) to prepare the low density polyethylene with epoxy functional groups on the branched chains. The preparation method comprises the following steps: A) adding a swelling agent of LDPE-g-MAH, EGDE and LDPE-g-MAH into a reaction kettle; B) stirring and heating to the swelling temperature to swell the LDPE-g-MAH for one hour, continuing heating and dissolving to the reaction temperature, adding a catalyst, and reacting for 3-5 hours; C) and taking out the reaction solution from the reaction kettle, adding a precipitator, carrying out suction filtration on the suspension, washing and drying to obtain the low-density polyethylene powder with the epoxy functional group on the branched chain.
Description
Technical field
The present invention relates to a kind of method of ldpe copolymer preparation, a kind of side chain of more specifically saying so has the preparation method of epoxy-functional new LDPE (film grade), the invention belongs to Polymer Synthesizing modification field.
Background technology
Vilaterm (PE) is a kind of universal thermoplastics, but its low-pole and unreactiveness have limited its application in more areas.Consider that epoxide group has very high reactive behavior; Can react and open loop with plurality of reagents such as hydrogen halide, water, alcohol, amine, Grignard reagents; Therefore; The new LDPE (film grade) (LDPE) that has an epoxy-functional can be given LDPE and have many reactive functions, and expansion LDPE uses in more field.For example, a chain end has the reactive compatibilizers that epoxide group LDPE can do the blend of LDPE and epoxy resin, makes various high polymer alloys of coupling hardness with softness.Again for example, generate reticulated structure as the linking agent that side chain has epoxide group LDPE, obtain having the thermosetting polymer compound of special performance with polyamine.This thermosetting polymer compound can be made the tamanori and the corrosion protection coating of high surface energy materials such as metal, pottery, glass.Purified polycthylene grafted maleic anhydride (PE-g-MAH) also has cohesive force and sticking power preferably to metal; Can improve the nonpolar of LDPE; As metal anti-corrosive paint or sizing agent; But it is slightly acidic metallic surface and oxide compound thereof there are certain corrodibility, influence the interface bonding of coating or sizing agent and metal.
" New Chemical Materials " 2010 the 5th phases disclose a kind ofly carries out the resin of epoxidation modification with epoxy chloropropane to LDPE, but its technology is complicated, and performance also remains further to be improved.
Summary of the invention
The present invention is directed to the technological deficiency and the problem of above-mentioned existing synthesis technique; A kind of preparation method that side chain has the epoxy-functional new LDPE (film grade) for preparing is provided; This method has the epoxy-functional new LDPE (film grade) with polycthylene grafted maleic anhydride (LDPE-g-MAH) and DGEEG (EGDE) preparation side chain, and equipment and technology are simple, and it is low that the product that makes has an acid number; Cross-linking agent content is few, the characteristics that adhesive property is high.
The present invention realizes through following technical scheme:
Side chain of the present invention has the preparation method of epoxy-functional new LDPE (film grade), and it may further comprise the steps:
A) in reaction kettle, add the swelling agent of LDPE-g-MAH, EGDE and LDPE-g-MAH;
B) stirring is warming up to swelling temperature, makes the LDPE-g-MAH swelling one hour, continues to heat up, be dissolved to temperature of reaction, adds catalyzer, reacts after 3～5 hours and finishes;
C) from reaction kettle, take out reaction soln, add precipitation agent, with the suspension liquid suction filtration, washing, drying obtains the new LDPE (film grade) powder that side chain has epoxy-functional.
Side chain of the present invention has the preparation method of epoxy-functional new LDPE (film grade), and its further technical scheme is said steps A) in melt flow rate >=10g/10min of LDPE-g-MAH, percentage of grafting 1.38～1.40%, degree of crosslinking is 0.
Side chain of the present invention has the preparation method of epoxy-functional new LDPE (film grade), and its further technical scheme can also be said steps A) in the swelling agent of LDPE-g-MAH be toluene or YLENE, consumption is 8～16 times of LDPE-g-MAH quality.
Side chain of the present invention has the preparation method of epoxy-functional new LDPE (film grade), and its further technical scheme can also be said steps A) in the consumption of EGDE be LDPE-g-MAH quality 10%～50%.
Side chain of the present invention has the preparation method of epoxy-functional new LDPE (film grade), and its further technical scheme can also be said step B) in swelling temperature be 80～110 ℃, stir speed (S.S.) is controlled at 100～500rpm.
Side chain of the present invention has the preparation method of epoxy-functional new LDPE (film grade), and its further technical scheme can also be said step B) in temperature of reaction be 111～150 ℃.
Side chain of the present invention has the preparation method of epoxy-functional new LDPE (film grade), and its further technical scheme can also be said step B) in catalyzer be Methylimidazole, consumption is 0.1%～5% of a LDPE-g-MAH quality.
Side chain of the present invention has the preparation method of epoxy-functional new LDPE (film grade), and its further technical scheme can also be said step C) in precipitation agent be water or acetone, consumption is 4～10 times of LDPE-g-MAH quality.
Side chain of the present invention has the preparation method of epoxy-functional new LDPE (film grade), and its further technical scheme can also be said step C) in washing be that the exsiccant temperature is 60～80 ℃ with 80 ℃ of hot water wash 3～5 times, the exsiccant time is 10 hours.
Compared with prior art the present invention has following beneficial effect:
1, present device is simple, and is easy to operate, and in short 3～5 hours of reaction times, the LDPE-g-MAH-g-EGDE that makes is a kind of white to a light brown powder, oxirane value 0.010～0.020mol100g
-1, degree of crosslinking is 0～2.0%, acid number 0.2～0.6mgg
-1
2, product is that a kind of side chain has the epoxy-functional new LDPE (film grade); Epoxy-functional has very high activity; Can give LDPE many reactive functions, can make the reactive compatibilizers of LDPE and epoxy blend modification, make various high polymer alloys of coupling hardness with softness; Can make the tamanori and the corrosion protection coating of materials such as metal, pottery, glass; Compare with PE-g-MAH acidity more a little less than, when making metal-to-metal adhesive and corrosion protection coating, erode metallic surfaces not, with the oxide compound reaction of metallic surface, thereby short-term is all stronger with long-term adhesive power.
Description of drawings
Fig. 1 is the product infrared spectrogram of embodiment 1 preparation
Embodiment
Melt flow rate >=10g/10min of used LDPE-g-MAH among the embodiment, percentage of grafting 1.38～1.40%, degree of crosslinking is 0.
Embodiment 1:
A) YLENE of adding 2.5kgLDPE-g-MAH, 1kgEGDE, 35L stirs and is warmed up to 90 ℃ in reaction kettle adds, and keeps temperature 1 hour.
B) continue to be warming up to 120 ℃ and in the reaction kettle constant pressure funnel, add the 50g Methylimidazole, reacted 4 hours.
C) from reaction kettle, take out reaction soln; Add precipitation agent water 15kg, with the suspension liquid suction filtration, 4 after drying of 80 ℃ of hot water wash; The exsiccant temperature is 70 ℃; The exsiccant time is 10 hours, and obtaining the new LDPE (film grade) powder that side chain has epoxy-functional is light brown LDPE-g-MAH-g-EGDE powder, through detecting its oxirane value 0.011～0.014mol100g
-1, acid number is 0.4mgg
-1, degree of crosslinking is 0.7%.
Product detects as shown in Figure 1 through ir spectra: 1739cm
-1Be the stretching vibration absorption peak of ester carbonyl group, the 1785cm in 1
-1, 1856cm
-1The acid anhydrides characteristic peak that place's absorption peak is, 1720cm
-1The absorption peak at place is the carboxylic carbonyl characteristic peak after the anhydride moiety hydrolysis, and contrast 2 can see that above absorption peak all disappears, at 1733cm
-1New absorption peak has appearred in the place, and this peak is the characteristic peak at ester carbonyl group peak, show after acid anhydrides is hydrolyzed into carboxylic acid with EGDE ring-opening reaction to have taken place, and reaction is more complete
Embodiment 2:
A) YLENE that in the reaction kettle charging opening, adds 2.5kgLDPE-g-MAH, 1kgEGDE, 40L stirs and to be warmed up to 90 ℃, keeps temperature 1 hour.
B) continue to be warming up to 150 ℃ and in the reaction kettle constant pressure funnel, add the 25g Methylimidazole, reacted 3 hours.
C) from reaction kettle, take out reaction soln; Add precipitation agent acetone 10kg, with the suspension liquid suction filtration, 3 after drying of 80 ℃ of hot water wash; The exsiccant temperature is 60 ℃; The exsiccant time is 10 hours, and obtaining the new LDPE (film grade) powder that side chain has epoxy-functional is light brown LDPE-g-MAH-g-EGDE powder, through detecting its oxirane value 0.010～0.013mol100g
-1, acid number is 0.5mgg
-1, degree of crosslinking is 0%.
Embodiment 3:
A) YLENE that in the reaction kettle charging opening, adds 2.5kgLDPE-g-MAH, 1kgEGDE, 40L stirs and to be warmed up to 90 ℃, keeps temperature 1 hour.
B) continue to be warming up to 115 ℃ and in the reaction kettle constant pressure funnel, add the 50g Methylimidazole, reacted 5 hours.
C) from reaction kettle, take out reaction soln; Add precipitation agent water 25kg, with the suspension liquid suction filtration, 5 after drying of 80 ℃ of hot water wash; The exsiccant temperature is 80 ℃; The exsiccant time is 10 hours, and obtaining the new LDPE (film grade) powder that side chain has epoxy-functional is light brown LDPE-g-MAH-g-EGDE powder, through detecting its oxirane value 0.012～0.015mol100g
-1, acid number is 0.3mgg
-1, degree of crosslinking is 1.5%.
Following among the present invention to the performance of products testing method:
One, the mensuration of oxirane value
The sample that accurately takes by weighing about 0.5g is put into flask, in flask, adds 80.0mL xylene solution, heating for dissolving.Hydrochloric acid-acetone soln the 5mL that draws 0.1mol/L adds in the flask, and reflux 1.0h adds two phenolphthalein indicators then, and with standard alkali solution titration to the red terminal point of 0.1mol/L, the consumption volume is V
2Pipette 5ml hydrochloric acid-acetone soln, add 3 phenolphthalein indicators, carry out blank titration (30s in accomplish), keep that 5s is colour-fast to be red terminal point, the volume that consumes the 0.1mol/L standard alkali solution is V
1
Be calculated as follows oxirane value:
In the formula: E-oxirane value (mol/100g); M-sample quality (g); C
NaOHConcentration (mol/L) for the NaOH standardized solution; V
1For controlled trial consumes NaOH volume (mL); V
2NaOH volume (mL) for sample consumption.
Two, the mensuration of acid number
Taking by weighing the heating of 0.2～0.3g sample and be dissolved in the 20mL YLENE, is indicator with phenolphthalein, to red, notes the volume V (mL) of the potassium hydroxide-ethanol solution of consumption with the titration of 0.05mol/L potassium hydroxide-ethanol solution
In the formula: 56-KOH relative molecular mass amount; The m-sample quality, g; c
KOH-KOH concentration (mol/L); V-consumes the volume (mL) of KOH.
Three, the mensuration of degree of crosslinking
Taking by weighing the sample of purifying about 2g, to put into apparatus,Soxhlet's behind the 200 order copper mesh parcel, is that extraction agent extracts after 24 hours continuously with YLENE, and the taking-up copper mesh is put into vacuum drying oven and is dried to constant weight.
Degree of crosslinking is calculated by following formula:
The m-sample quality, W
0-former copper mesh quality, W
1The quality of-last copper mesh.
Claims (9)
1. a side chain has the preparation method of epoxy-functional new LDPE (film grade), it is characterized in that may further comprise the steps:
A) in reaction kettle, add the swelling agent of LDPE-g-MAH, EGDE and LDPE-g-MAH;
B) stirring is warming up to swelling temperature, makes the LDPE-g-MAH swelling one hour, continues to heat up, be dissolved to temperature of reaction, adds catalyzer, reacts after 3～5 hours and finishes;
C) from reaction kettle, take out reaction soln, add precipitation agent, with the suspension liquid suction filtration, washing, drying obtains the new LDPE (film grade) powder that side chain has epoxy-functional.
2. have the preparation method of epoxy-functional new LDPE (film grade) according to claims 1 described side chain, it is characterized in that said steps A) in melt flow rate >=10g/10min of LDPE-g-MAH, percentage of grafting 1.38～1.40%, degree of crosslinking is 0.
3. have the preparation method of epoxy-functional new LDPE (film grade) according to claims 1 described side chain, it is characterized in that said steps A) in the swelling agent of LDPE-g-MAH be toluene or YLENE, consumption is 8～16 times of LDPE-g-MAH quality.
4. have the preparation method of epoxy-functional new LDPE (film grade) according to claims 1 described side chain, it is characterized in that said steps A) in the consumption of EGDE be LDPE-g-MAH quality 10%～50%.
5. have the preparation method of epoxy-functional new LDPE (film grade) according to claims 1 described side chain, it is characterized in that said step B) in swelling temperature be 80～110 ℃, stir speed (S.S.) is controlled at 100～500rpm.
6. have the preparation method of epoxy-functional new LDPE (film grade) according to claims 1 described side chain, it is characterized in that said step B) in temperature of reaction be 111～150 ℃.
7. have the preparation method of epoxy-functional new LDPE (film grade) according to claims 1 described side chain, it is characterized in that said step B) in catalyzer be Methylimidazole, consumption is 0.1%～5% of a LDPE-g-MAH quality.
8. have the preparation method of epoxy-functional new LDPE (film grade) according to claims 1 described side chain, it is characterized in that said step C) in precipitation agent be water or acetone, consumption is 4～10 times of LDPE-g-MAH quality.
9. have the preparation method of epoxy-functional new LDPE (film grade) according to claims 1 described side chain, it is characterized in that said step C) in washing be that the exsiccant temperature is 60～80 ℃ with 80 ℃ of hot water wash 3～5 times, the exsiccant time is 10 hours.
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| CN111333991A (en) * | 2020-04-09 | 2020-06-26 | 安徽松泰包装材料有限公司 | High-temperature-resistant composite packaging film and preparation method thereof |
| CN113045267A (en) * | 2021-02-20 | 2021-06-29 | 江苏金海宁新型建材科技有限公司 | Low-shrinkage waterproof concrete for underground engineering and preparation process thereof |
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| CN111333991A (en) * | 2020-04-09 | 2020-06-26 | 安徽松泰包装材料有限公司 | High-temperature-resistant composite packaging film and preparation method thereof |
| CN111333991B (en) * | 2020-04-09 | 2023-01-13 | 安徽松泰包装材料有限公司 | High-temperature-resistant composite packaging film and preparation method thereof |
| CN113045267A (en) * | 2021-02-20 | 2021-06-29 | 江苏金海宁新型建材科技有限公司 | Low-shrinkage waterproof concrete for underground engineering and preparation process thereof |
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Application publication date: 20120509 |