CN109293696A - One-step synthesis method cotton N- methylol -3-(dimethoxyphosphoryl) propionamide fire retardant method - Google Patents
One-step synthesis method cotton N- methylol -3-(dimethoxyphosphoryl) propionamide fire retardant method Download PDFInfo
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- CN109293696A CN109293696A CN201811381089.5A CN201811381089A CN109293696A CN 109293696 A CN109293696 A CN 109293696A CN 201811381089 A CN201811381089 A CN 201811381089A CN 109293696 A CN109293696 A CN 109293696A
- Authority
- CN
- China
- Prior art keywords
- fire retardant
- propionamide
- methylol
- dimethoxyphosphoryl
- cotton
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 239000003063 flame retardant Substances 0.000 title claims abstract description 44
- 238000000034 method Methods 0.000 title claims abstract description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 229920000742 Cotton Polymers 0.000 title claims abstract description 15
- 238000001308 synthesis method Methods 0.000 title claims abstract description 8
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 title abstract description 4
- 229940080818 propionamide Drugs 0.000 title abstract description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims abstract description 8
- CCJAYIGMMRQRAO-UHFFFAOYSA-N 2-[4-[(2-hydroxyphenyl)methylideneamino]butyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCCCN=CC1=CC=CC=C1O CCJAYIGMMRQRAO-UHFFFAOYSA-N 0.000 claims abstract description 7
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 claims abstract description 7
- 230000009471 action Effects 0.000 claims abstract description 3
- 239000003054 catalyst Substances 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- -1 sodium alkoxide Chemical class 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 27
- 238000002360 preparation method Methods 0.000 abstract description 4
- 238000006555 catalytic reaction Methods 0.000 abstract 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 9
- 239000013256 coordination polymer Substances 0.000 description 9
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- DLQDGVZAEYZNTG-UHFFFAOYSA-N dimethyl hydrogen phosphite Chemical class COP(O)OC DLQDGVZAEYZNTG-UHFFFAOYSA-N 0.000 description 4
- 238000007599 discharging Methods 0.000 description 4
- 238000009413 insulation Methods 0.000 description 4
- SUBJHSREKVAVAR-UHFFFAOYSA-N sodium;methanol;methanolate Chemical compound [Na+].OC.[O-]C SUBJHSREKVAVAR-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- HZYXVJSIPKQSHO-UHFFFAOYSA-N n-dimethoxyphosphorylpropanamide Chemical compound CCC(=O)NP(=O)(OC)OC HZYXVJSIPKQSHO-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000662429 Fenerbahce Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/44—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen containing nitrogen and phosphorus
- D06M13/447—Phosphonates or phosphinates containing nitrogen atoms
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/02—Natural fibres, other than mineral fibres
- D06M2101/04—Vegetal fibres
- D06M2101/06—Vegetal fibres cellulosic
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/30—Flame or heat resistance, fire retardancy properties
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Fireproofing Substances (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
The invention discloses a kind of one-step synthesis method cotton N- methylol -3-(dimethoxyphosphoryls) method of propionamide fire retardant.The present invention mixes N hydroxymethyl acrylamide with dimethylphosphite in proportion, reacts 1-4h at 40-80 DEG C under the action of the catalysis of sodium methoxide, and N- methylol -3- (dimethoxyphosphoryl) propionamide fire retardant can be made.Preparation method of the invention is simple, and the content of formaldehyde in product is low, function admirable, has the value promoted.
Description
Technical field
The invention belongs to function additive synthesis technical fields, specifically, being related to a kind of one-step synthesis method cotton N- hydroxyl first
The method of base -3- (dimethoxyphosphoryl) propionamide fire retardant.
Background technique
Cotton flame retardant N- methylol -3- (dimethoxyphosphoryl) propionamide fire retardant (abbreviation fire retardant CP), be by
Ciba's invention, be always the head of cotton durable flame-retardant finishing with good flame retardant property and water resistance performance
Select auxiliary agent, this auxiliary agent is synthesized by two-step method, the first step be by dimethylphosphite under alkaline condition with acrylamide
Reaction generates dimethoxyphosphoryl propionamide.Second step is to carry out methylolation to dimethoxyphosphoryl propionamide with formaldehyde
Reaction, can be prepared by target product.Due to excessive formaldehyde having been used, so that in product during fire retardant CP synthesis
Content of formaldehyde it is higher, ultimately cause with its arrange cotton fabric in content of formaldehyde it is exceeded, environment and consumer are brought in this way
It influences.For this purpose, researcher continually develops low aldehyde or the fire retardant without aldehyde, but there are no a mature products by market so far
Receive.There is in good flame retardant property and synthesis process the problem of using more formaldehyde based on fire retardant CP, the present invention is special
Benefit discloses the preparation method of one-step synthesis method fire retardant CP a kind of.
Summary of the invention
For overcome the deficiencies in the prior art, the purpose of the present invention is to provide a kind of one-step synthesis method N- methylol -3-
The method of (dimethoxyphosphoryl) propionamide fire retardant.The processing step of the method for the present invention is simple, first in fire retardant obtained
Aldehyde is few, excellent fireproof performance.
Technical solution of the present invention is specifically described as follows.
The present invention provides a kind of one-step synthesis method cotton N- methylol -3- (dimethoxyphosphoryl) propionamide fire retardant
Method, by after N hydroxymethyl acrylamide is mixed with dimethylphosphite under the action of catalyst in 40-80 DEG C of temperature
The lower reaction of degree, is made N- methylol -3- (dimethoxyphosphoryl) propionamide fire retardant；Wherein: catalyst is alcohol sodium solution.
In the present invention, catalyst is sodium methoxide.
In the present invention, the molar ratio of catalyst and N hydroxymethyl acrylamide is 0.1:1-0.4:1.
In the present invention, the molar ratio of N hydroxymethyl acrylamide and dimethylphosphite is 1:1-1:1.4.
In the present invention, reaction time 1-4h.
The present invention is by evaluating the flame retardant performance of this method preparation in terms of following two:
The content of formaldehyde is measured by national standard GB5544 analysis method；
Flame retardant property according to GB/T 5455-1997 " textile combustion performance test normal beam technique " measurement fabric.
Compared to the prior art, the beneficial effects of the present invention are:
Compared with the present invention and two-step method synthesis fire retardant CP, preparation method is simple, and a step can be completed, product yield compared with
Height, the content of formaldehyde in product is low, and properties of product are stablized, which has promotional value.
Specific embodiment
Combined with specific embodiments below, to technical solution of the present invention into being described further.Raw material N- in embodiment
Hydroxymethyl acrylamide, dimethylphosphite derive from Adamas Reagent company, methanol solution of sodium methylate (30%) source
In Shanghai Da Rui fine chemicals Co., Ltd.
Embodiment 1
51 grams of N hydroxymethyl acrylamides and 56 grams of dimethylphosphites are mixed, catalyst sodium methoxide methanol solution is added
2.7 grams, at 65 DEG C after insulation reaction 2 hours, vacuum distillation, cooling, discharging obtain N- methylol -3- (dimethoxyphosphoryl
Base) propionamide fire retardant.
Embodiment 2
61 grams of N hydroxymethyl acrylamides and 79 grams of dimethylphosphites are mixed, catalyst sodium methoxide methanol solution is added
6.48 grams, at 70 DEG C after insulation reaction 1.5 hours, vacuum distillation, cooling, discharging obtain N- methylol -3- (dimethoxy
Phosphoryl) propionamide fire retardant.
Embodiment 3
81 grams of N hydroxymethyl acrylamides and 106 grams of dimethylphosphites are mixed, it is molten that catalyst sodium methoxide methanol is added
4.32 grams of liquid, at 75 DEG C after insulation reaction 2 hours, vacuum distillation, cooling, discharging obtain N- methylol -3- (dimethoxy
Phosphoryl) propionamide fire retardant.
Embodiment 4
101 grams of N hydroxymethyl acrylamides and 154 grams of dimethylphosphites are mixed, it is molten that catalyst sodium methoxide methanol is added
8.1 grams of liquid, at 75 DEG C after insulation reaction 2 hours, vacuum distillation, cooling, discharging obtain N- methylol -3- (dimethoxy phosphorus
Acyl group) propionamide fire retardant.
By N- methylol -3- (dimethoxyphosphoryl) propionamide fire retardant made from embodiment 1,2,3,4, from following two
A aspect evaluates it, and the interpretation of result (table 1) of fire retardant is made in (1) one-step method；(2) one-step method is made fire retardant and arranges
The flame retardant property of cotton fabric evaluates (table 2).
Fire retardant CP is made using bibliography (Liu Zhiming, Gansu chemical industry, 1995, (3): 31-36) two-step method.
The analysis result of fire retardant is made in 1 one-step method of table
As it can be seen from table 1 N- methylol -3- (dimethoxyphosphoryl) propionamide fire retardant is made in the process of the present invention
With two-step method made from compared with fire retardant CP, in terms of appearance, viscosity, solid content, molecular structure, they are almost the same, but
The fire retardant as made from one-step method will embody the excellent of one-step method lower than fire retardant made from two-step method in terms of content of formaldehyde
Gesture.
The flame retardance results of fire retardant finishing of cotton textiles made from 2 one-step method of table
| Project | Analysis method | The cotton fabric that one-step method product arranges | The cotton fabric that fire retardant CP is arranged |
| Carbon is long (cm) | GB5455 | 8.3 | 8.1 |
| After flame time (s) | GB5455 | 0 | 0 |
| After flame time (s) | GB5455 | 0 | 0 |
Note: finishing technique: with liquid (50%) → second dipping and rolling (pick-up 70-80%) → preliminary drying (105 DEG C × 3min) →
Bake (165-170 DEG C × 2-3min) → alkali cleaning (sodium carbonate: 20g/L, 40 DEG C × 20min) → washing → drying
From table 2 it can be seen that the fire retardant as made from one-step method, with the flame retardant property and fire retardant of its finishing of cotton textiles
The flame retardant property of CP finishing of cotton textiles is suitable, has all reached B1 rank.
The foregoing descriptions are merely preferred embodiments of the present invention.According to the technical essence of the invention to the above reality
Any simple modification, equivalent change and modification made by example are applied, are fallen within the protection scope of the present invention.
Claims (5)
1. a kind of one-step synthesis method cotton method of N- methylol -3- (dimethoxyphosphoryl) propionamide fire retardant, feature
Be, by after N hydroxymethyl acrylamide is mixed with dimethylphosphite under the action of catalyst in 40-80 DEG C of temperature
The lower reaction of degree, is made N- methylol -3- (dimethoxyphosphoryl) propionamide fire retardant；Wherein: catalyst is sodium alkoxide.
2. the method according to claim 1, wherein catalyst is sodium methoxide.
3. method according to claim 1 or 2, which is characterized in that the molar ratio of catalyst and N hydroxymethyl acrylamide
For 0.1:1-0.4:1.
4. the method according to claim 1, wherein mole of N hydroxymethyl acrylamide and dimethylphosphite
Than for 1:1-1:1.4.
5. the method according to claim 1, wherein the reaction time is 1~4h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811381089.5A CN109293696A (en) | 2018-11-20 | 2018-11-20 | One-step synthesis method cotton N- methylol -3-(dimethoxyphosphoryl) propionamide fire retardant method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811381089.5A CN109293696A (en) | 2018-11-20 | 2018-11-20 | One-step synthesis method cotton N- methylol -3-(dimethoxyphosphoryl) propionamide fire retardant method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109293696A true CN109293696A (en) | 2019-02-01 |
Family
ID=65143249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811381089.5A Pending CN109293696A (en) | 2018-11-20 | 2018-11-20 | One-step synthesis method cotton N- methylol -3-(dimethoxyphosphoryl) propionamide fire retardant method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109293696A (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102060873A (en) * | 2010-09-16 | 2011-05-18 | 中国科学技术大学 | Method for preparing N-hydroxymethyl-3-(dimethoxyphosphoryl) propionamide |
| CN102851944A (en) * | 2012-08-29 | 2013-01-02 | 昆山铁牛衬衫厂 | Fire-retardant finishing method of terylene fabric |
| CN103130832A (en) * | 2011-11-24 | 2013-06-05 | 上海雅运纺织助剂有限公司 | Improved preparation method of (methyl)acrylamido N-hydroxymethyldialkyl phosphonate as flame retardant |
| WO2017006295A1 (en) * | 2015-07-08 | 2017-01-12 | Glaxosmithkline Intellectual Property (No.2) Limited | Hydroxy formamide derivatives and their use |
| CN106939511A (en) * | 2017-04-21 | 2017-07-11 | 齐齐哈尔大学 | A kind of phosphorus nitrogen chlorine-resistant fire retardant and its synthetic method |
-
2018
- 2018-11-20 CN CN201811381089.5A patent/CN109293696A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102060873A (en) * | 2010-09-16 | 2011-05-18 | 中国科学技术大学 | Method for preparing N-hydroxymethyl-3-(dimethoxyphosphoryl) propionamide |
| CN103130832A (en) * | 2011-11-24 | 2013-06-05 | 上海雅运纺织助剂有限公司 | Improved preparation method of (methyl)acrylamido N-hydroxymethyldialkyl phosphonate as flame retardant |
| CN102851944A (en) * | 2012-08-29 | 2013-01-02 | 昆山铁牛衬衫厂 | Fire-retardant finishing method of terylene fabric |
| WO2017006295A1 (en) * | 2015-07-08 | 2017-01-12 | Glaxosmithkline Intellectual Property (No.2) Limited | Hydroxy formamide derivatives and their use |
| CN106939511A (en) * | 2017-04-21 | 2017-07-11 | 齐齐哈尔大学 | A kind of phosphorus nitrogen chlorine-resistant fire retardant and its synthetic method |
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Application publication date: 20190201 |