JP2018507286A - 臭素化及びハロ水和化ポリマーを生成するための方法 - Google Patents
臭素化及びハロ水和化ポリマーを生成するための方法 Download PDFInfo
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- JP2018507286A JP2018507286A JP2017538950A JP2017538950A JP2018507286A JP 2018507286 A JP2018507286 A JP 2018507286A JP 2017538950 A JP2017538950 A JP 2017538950A JP 2017538950 A JP2017538950 A JP 2017538950A JP 2018507286 A JP2018507286 A JP 2018507286A
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- Prior art keywords
- brominated
- polymer
- halohydrated
- conjugated diene
- polymers
- 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.)
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- 229920000642 polymer Polymers 0.000 title claims abstract description 209
- 238000000034 method Methods 0.000 title claims description 43
- 230000008569 process Effects 0.000 title claims description 13
- 150000001993 dienes Chemical class 0.000 claims abstract description 59
- -1 phosphonium tribromides Chemical group 0.000 claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
- 239000002904 solvent Substances 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 28
- 238000005893 bromination reaction Methods 0.000 claims description 25
- 239000006260 foam Substances 0.000 claims description 24
- 230000031709 bromination Effects 0.000 claims description 23
- 239000000463 material Substances 0.000 claims description 22
- 239000002245 particle Substances 0.000 claims description 21
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 17
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 16
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 15
- 239000004604 Blowing Agent Substances 0.000 claims description 12
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 12
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- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 6
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- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
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- 238000006243 chemical reaction Methods 0.000 abstract description 30
- 239000003063 flame retardant Substances 0.000 abstract description 13
- 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 abstract description 7
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
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- GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 description 5
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical class C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 5
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 5
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- SGXVTRUKGXCZQB-UHFFFAOYSA-N Br[Br-]Br.CC[N+](CC)(CC)CC Chemical compound Br[Br-]Br.CC[N+](CC)(CC)CC SGXVTRUKGXCZQB-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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- 239000004593 Epoxy Substances 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
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- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
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- 125000003118 aryl group Chemical group 0.000 description 2
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- 239000007810 chemical reaction solvent Substances 0.000 description 2
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- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 2
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- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
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- 150000002738 metalloids Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004597 plastic additive Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- HWLDNSXPUQTBOD-UHFFFAOYSA-N platinum-iridium alloy Chemical group [Ir].[Pt] HWLDNSXPUQTBOD-UHFFFAOYSA-N 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000582 polyisocyanurate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- JQRYUMGHOUYJFW-UHFFFAOYSA-N pyridine;trihydrobromide Chemical compound [Br-].[Br-].[Br-].C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1 JQRYUMGHOUYJFW-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- 125000005497 tetraalkylphosphonium group Chemical group 0.000 description 1
- XXSLZJZUSYNITM-UHFFFAOYSA-N tetrabutylammonium tribromide Chemical compound Br[Br-]Br.CCCC[N+](CCCC)(CCCC)CCCC XXSLZJZUSYNITM-UHFFFAOYSA-N 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000002937 thermal insulation foam Substances 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- 229920000428 triblock copolymer Polymers 0.000 description 1
- PRXNKYBFWAWBNZ-UHFFFAOYSA-N trimethylphenylammonium tribromide Chemical compound Br[Br-]Br.C[N+](C)(C)C1=CC=CC=C1 PRXNKYBFWAWBNZ-UHFFFAOYSA-N 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/12—Incorporating halogen atoms into the molecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/18—Introducing halogen atoms or halogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/18—Introducing halogen atoms or halogen-containing groups
- C08F8/20—Halogenation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/18—Introducing halogen atoms or halogen-containing groups
- C08F8/20—Halogenation
- C08F8/22—Halogenation by reaction with free halogens
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2309/00—Characterised by the use of homopolymers or copolymers of conjugated diene hydrocarbons
- C08J2309/06—Copolymers with styrene
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Inorganic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Abstract
Description
Claims (25)
- 少なくとも1つの共役ジエンの臭素化及びハロ水和化(halohydrated)ポリマーを調製するための方法であって、(a)少なくとも1つの共役ジエンの開始ポリマーを四級アンモニウムトリブロミド、四級ホスホニウムトリブロミド化合物、または四級アンモニウムトリブロミド及び四級ホスホニウムトリブロミドの両方と反応させ、前記開始ポリマー中の前記共役ジエンの繰り返し単位の50%〜98%を臭素化して、部分的に臭素化されたポリマーを形成することと、次いで、(b)水及び前記部分的に臭素化されたポリマーのための水混和性溶媒系の存在下で、前記部分的に臭素化されたポリマーをN−ハロイミド化合物と反応させて、前記共役ジエンの繰り返し単位の残りの少なくとも一部をハロ水和化し、臭素化及びハロ水和化ポリマーを生成することと、を含む、方法。
- 前記N−ハロイミドが、N−ハロスクシンイミドである、請求項1に記載の方法。
- 前記N−ハロイミドが、N−ブロモイミドである、請求項1または2に記載の方法。
- 前記共役ジエンの単位の65〜95%がステップ(a)で臭素化され、前記共役ジエンの単位の5〜35%がステップ(b)でハロ水和化され、前記共役ジエンの単位の0〜5%が反応しない、請求項1〜3のいずれかに記載の方法。
- 前記共役ジエンの単位の75〜98%がステップ(a)で臭素化され、前記共役ジエンの単位の2〜25%がステップ(b)でハロ水和化され、前記共役ジエンの単位の0〜5%が反応しない、請求項1〜3のいずれかに記載の方法。
- 前記共役ジエンの単位の80〜95%がステップ(a)で臭素化され、前記共役ジエンの単位の5〜20%がステップ(b)でハロ水和化され、前記共役ジエンの単位の0〜5%が反応しない、請求項5に記載の方法。
- ステップ(b)において、前記水混和性溶媒系中の前記部分的に臭素化されたポリマーの濃度が、部分的に臭素化されたポリマーと溶媒系とを組み合わせた重量に基づいて、2〜25重量パーセントである、請求項1〜6のいずれかに記載の方法。
- ステップ(b)において、水が、前記溶媒系の1重量部当たり0.25〜1重量部の量で存在する、請求項1〜7のいずれかに記載の方法。
- 前記開始ポリマーが、ポリスチレン標準物に対するゲル浸透クロマトグラフィーによって、少なくとも20,000の重量平均分子量を有するスチレン及びブタジエンのコポリマーである、請求項1〜8のいずれかに記載の方法。
- 前記方法から得られた前記臭素化及びハロ水和化ポリマーが、3重量パーセント以下のゲル材料を含有する熱可塑性材料である、請求項1〜9のいずれかに記載の方法。
- 前記臭素化及びハロ水和化が、ステップ(b)または後のステップで架橋している、請求項1〜9のいずれかに記載の方法。
- 前記臭素化及びハロ水和化ポリマーが、粒子に形成される、請求項1〜11のいずれかに記載の方法。
- 請求項1〜12のいずれかに記載の方法に従って作製される、臭素化及びハロ水和化ポリマー。
- 少なくとも1つの共役ジエンの臭素化及びハロ水和化ポリマーであって、前記ポリマーの前記共役ジエンの単位の2〜50%がハロ水和化され、前記共役ジエンの単位の50〜98%が臭素化され、前記共役ジエンの単位の0〜10%が反応せず、臭素化及びハロ水和化ポリマーが、少なくとも250℃の5%重量減少温度を有する、臭素化及びハロ水和化ポリマー。
- 前記共役ジエンの単位の5〜35%がハロ水和化され、前記共役ジエンの単位の65〜95%が臭素化され、前記共役ジエンの単位の0〜5%が反応しない、請求項13に記載の臭素化及びハロ水和化ポリマー。
- 前記共役ジエンの単位の2〜25%がハロ水和化され、前記共役ジエンの単位の75〜98%が臭素化され、前記共役ジエンの単位の0〜5%が反応しない、請求項13に記載の臭素化及びハロ水和化ポリマー。
- 前記共役ジエンの単位の5〜20%がハロ水和化され、前記共役ジエンの単位の80〜95%が臭素化され、前記共役ジエンの単位の0〜5%が反応しない、請求項16に記載の臭素化及びハロ水和化ポリマー。
- 3重量パーセント以下、及びより好ましくは1重量パーセント以下のゲル材料を含有する熱可塑性材料である、請求項14〜17のいずれかに記載の臭素化及びハロ水和化ポリマー。
- 架橋している、請求項14〜17のいずれかに記載の臭素化及びハロ水和化ポリマー。
- 500nm〜25μmの直径を有する粒子の形態である、請求項14〜19のいずれかに記載の臭素化及びハロ水和化ポリマー。
- 少なくとも1つのポリオールと、請求項14〜20のいずれかに記載の臭素化及びハロ水和化ポリマーと、を含む、ポリオール組成物。
- 請求項14〜20のいずれかに記載の臭素化及びハロ水和化ポリマーを含有する、イソシアネート系ポリマー。
- バルクポリマーと、請求項14〜20のいずれかに記載の臭素化及びハロ水和化ポリマーと、を含有する、押出成形されたポリマー発泡体。
- 前記バルクポリマーと、前記臭素化及びハロ水和化ポリマーと、二酸化炭素、水、及びアルコールのうちの少なくとも1つを含有する発泡剤とを含有する加圧溶融体を形成することと、前記溶融体を、開口部を通してより低圧の区域に押し込み、そこで前記発泡剤が膨張し、前記バルクポリマーが凝固して発泡体を形成することと、を含む、請求項23に記載の押出成形されたポリマー発泡体を作製するための方法。
- スチレンの1つ以上のポリマーもしくはコポリマー、ポリアクリレートもしくはポリメタクリレートポリマー、またはそれらの任意の2つ以上の混合物であるバルクポリマーと、請求項1〜20のいずれかに記載の臭素化及びハロ水和化ポリマーと、を含む、ポリマーブレンド。
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PCT/US2016/015216 WO2016123263A1 (en) | 2015-01-30 | 2016-01-27 | Method for producing brominated and halohydrated polymers |
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JP2022515800A (ja) * | 2018-12-27 | 2022-02-22 | パブリック・ジョイント・ストック・カンパニー・“シブール・ホールディング” | 変性(コ)ポリマー、それを調製する方法及びその使用 |
JP2022516723A (ja) * | 2018-12-27 | 2022-03-02 | パブリック・ジョイント・ストック・カンパニー・“シブール・ホールディング” | 変性ジエン含有(コ)ポリマー、その調製方法及び難燃剤としての使用 |
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WO2018210961A1 (de) | 2017-05-17 | 2018-11-22 | Basf Se | Bromierte flammschutzmittel |
US11248080B2 (en) | 2017-05-17 | 2022-02-15 | Basf Se | Brominated flame retardant |
WO2020139111A1 (en) | 2018-12-27 | 2020-07-02 | Public Joint Stock Company "Sibur Holding" | Modified diene-containing (co)polymer, method for producing the same and use of the same as a flame retardant |
WO2020139113A1 (en) | 2018-12-27 | 2020-07-02 | Public Joint Stock Company "Sibur Holding" | Modified diene-containing (co)polymer, method for preparing thereof and use of the same as flame retardant |
WO2020139114A1 (en) | 2018-12-27 | 2020-07-02 | Public Joint Stock Company "Sibur Holding" | Modified diene-containing (co)polymer, method for preparing thereof and use of the same as flame retardant |
RU2741967C1 (ru) * | 2019-12-26 | 2021-02-01 | Публичное акционерное общество «СИБУР Холдинг» | Способ получения модифицированного диенсодержащего (со)полимера и его применение в качестве антипирена |
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JP2022515800A (ja) * | 2018-12-27 | 2022-02-22 | パブリック・ジョイント・ストック・カンパニー・“シブール・ホールディング” | 変性(コ)ポリマー、それを調製する方法及びその使用 |
JP2022516723A (ja) * | 2018-12-27 | 2022-03-02 | パブリック・ジョイント・ストック・カンパニー・“シブール・ホールディング” | 変性ジエン含有(コ)ポリマー、その調製方法及び難燃剤としての使用 |
JP7142786B2 (ja) | 2018-12-27 | 2022-09-27 | パブリック・ジョイント・ストック・カンパニー・“シブール・ホールディング” | 変性(コ)ポリマー、それを調製する方法及びその使用 |
JP7186883B2 (ja) | 2018-12-27 | 2022-12-09 | パブリック・ジョイント・ストック・カンパニー・“シブール・ホールディング” | 変性ジエン含有(コ)ポリマー、その調製方法及び難燃剤としての使用 |
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US10781271B2 (en) | 2020-09-22 |
WO2016123263A8 (en) | 2017-08-03 |
JP6502510B2 (ja) | 2019-04-17 |
US10457751B2 (en) | 2019-10-29 |
CN107207631B (zh) | 2019-04-12 |
EP3250613A1 (en) | 2017-12-06 |
CN107207631A (zh) | 2017-09-26 |
CA2975380A1 (en) | 2016-08-04 |
US20180002455A1 (en) | 2018-01-04 |
EP3250613B1 (en) | 2019-06-19 |
US20200002442A1 (en) | 2020-01-02 |
ES2743445T3 (es) | 2020-02-19 |
WO2016123263A1 (en) | 2016-08-04 |
CA2975380C (en) | 2023-08-22 |
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