JP2019521233A - Pbs樹脂組成物及びその製造方法 - Google Patents
Pbs樹脂組成物及びその製造方法 Download PDFInfo
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- JP2019521233A JP2019521233A JP2019502633A JP2019502633A JP2019521233A JP 2019521233 A JP2019521233 A JP 2019521233A JP 2019502633 A JP2019502633 A JP 2019502633A JP 2019502633 A JP2019502633 A JP 2019502633A JP 2019521233 A JP2019521233 A JP 2019521233A
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- pbs resin
- titanium
- phosphorus
- pbs
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- 239000011342 resin composition Substances 0.000 title claims abstract description 54
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 40
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 40
- 239000011574 phosphorus Substances 0.000 claims abstract description 40
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 17
- 239000010936 titanium Substances 0.000 claims abstract description 17
- 229920005989 resin Polymers 0.000 claims abstract description 12
- 239000011347 resin Substances 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000012153 distilled water Substances 0.000 claims abstract description 10
- 230000008859 change Effects 0.000 claims abstract description 8
- 239000000155 melt Substances 0.000 claims abstract description 4
- 238000002844 melting Methods 0.000 claims description 11
- 230000008018 melting Effects 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 claims description 6
- 238000000354 decomposition reaction Methods 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 238000004458 analytical method Methods 0.000 claims description 3
- 229910001873 dinitrogen Inorganic materials 0.000 claims description 3
- 238000004710 electron pair approximation Methods 0.000 claims description 3
- 239000012528 membrane Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 3
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 claims description 3
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 claims description 3
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 claims description 3
- 239000008187 granular material Substances 0.000 claims description 2
- 238000000227 grinding Methods 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 claims description 2
- 229920002961 polybutylene succinate Polymers 0.000 description 37
- 239000004631 polybutylene succinate Substances 0.000 description 37
- 230000000052 comparative effect Effects 0.000 description 5
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- UVCJGUGAGLDPAA-UHFFFAOYSA-N ensulizole Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 description 2
- 229920009537 polybutylene succinate adipate Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229920006167 biodegradable resin Polymers 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- JSKZWIGBDHYSGI-UCSXVCBISA-L disodium;(6r,7r)-7-[[(2e)-2-(2-amino-1,3-thiazol-4-yl)-2-[1-[2-(3,4-dihydroxybenzoyl)hydrazinyl]-2-methyl-1-oxopropan-2-yl]oxyiminoacetyl]amino]-3-[(2-carboxylato-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2. Chemical group [Na+].[Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)CSC1=CC(=NC2=NC(=NN21)C([O-])=O)C)C([O-])=O)C(=O)C(\C=1N=C(N)SC=1)=N\OC(C)(C)C(=O)NNC(=O)C1=CC=C(O)C(O)=C1 JSKZWIGBDHYSGI-UCSXVCBISA-L 0.000 description 1
- 239000010791 domestic waste Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 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
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012785 packaging film Substances 0.000 description 1
- 229920006280 packaging film Polymers 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000013502 plastic waste Substances 0.000 description 1
- -1 polybutylene succinate Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0091—Complexes with metal-heteroatom-bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Biological Depolymerization Polymers (AREA)
Abstract
Description
(a)PBS樹脂と、
(b)チタン元素と、
(c)リン元素とを含む。
1,4−コハク酸、1,4−ブタンジオール、チタン含有化合物を混合して、圧力50−100kPa、温度180−250℃で、1−5時間保持するステップ1と、
CO2を導入して、リン含有化合物を加えて、10−30min保持するステップ2と、
ステップ2で得られた混合物の圧力を100Pa未満に下げて、230−250℃に加熱し、3−6時間保持して、窒素ガスを導入して造粒するステップ3とを含む。
Claims (10)
- PBS樹脂組成物であって、
成分として、a.PBS樹脂と、b.チタン元素と、c.リン元素とを含むことを特徴とするPBS樹脂組成物。 - PBS樹脂組成物において、チタン元素とリン元素の重量比率の範囲は0.6−10:1であることを特徴とする請求項1に記載のPBS樹脂組成物。
- 前記PBS樹脂組成物において、チタン元素とリン元素の重量比率の範囲は0.7−4:1、好ましくは1.25−1.5:1であることを特徴とする請求項2に記載のPBS樹脂組成物。
- 前記PBS樹脂組成物において、チタン元素の重量含有量は20−200ppmであり、リン元素の重量含有量は15−70ppmであることを特徴とする請求項1に記載のPBS樹脂組成物。
- PBS樹脂組成物において、リン元素とチタン元素の重量含有量については、US EPA方法3052:1996を参照して、ICP−OES分析を用いて、前記PBS樹脂組成物0.1gを秤量して、粉砕後、硝酸5mLを前記PBS樹脂組成物を超えるまで加えて、次に過酸化水素1.0mLを滴下して2min反応させ、マイクロ波分解缶に密封して210℃で3時間分解し、室温に冷却させた後、0.45μm濾過膜を用いて濾過した後、蒸留水で50mLになるまで希釈して、ICP−OESによりテストする手順に従い測定されることを特徴とする請求項1に記載のPBS樹脂組成物。
- 190℃、2.16kgの重りの条件でテストしたとき、溶融指数は3.0−10.0g/10minであることを特徴とする請求項1に記載のPBS樹脂組成物。
- 前記チタン元素はチタン含有化合物に由来し、チタン含有化合物はチタン酸n−ブチル又はチタン酸イソプロピルから選ばれる1種又は2種の混合物であることを特徴とする請求項1に記載のPBS樹脂組成物。
- 前記リン元素はリン含有化合物に由来し、リン含有化合物はリン酸トリエチル、リン酸トリメチル、リン酸トリブチル又はリン酸トリフェニルから選ばれる1種又は複数種の混合物であることを特徴とする請求項1に記載のPBS樹脂組成物。
- 95℃の蒸留水水浴で12時間処理した後、90℃の環境で3時間乾燥させたところ、溶融指数変化は50.0g/10minより小さいことを特徴とする請求項1に記載のPBS樹脂組成物。
- 1,4−コハク酸、1,4−ブタンジオール、チタン含有化合物を混合して、圧力50−100kPa、温度180−250℃で、1−5時間保持するステップ1と、
CO2を導入して、リン含有化合物を加えて、10−30min保持するステップ2と、
ステップ2で得られた混合物の圧力を100Pa未満に下げて、230−250℃に加熱し、3−6時間保持して、窒素ガスを導入して造粒するステップ3とを含む請求項1−8のいずれかに記載のPBS樹脂の製造方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201611182854.1A CN107459785B (zh) | 2016-12-20 | 2016-12-20 | 一种pbs树脂组合物及其制备方法 |
CN201611182854.1 | 2016-12-20 | ||
PCT/CN2017/113750 WO2018113496A1 (zh) | 2016-12-20 | 2017-11-30 | 一种pbs树脂组合物及其制备方法 |
Publications (2)
Publication Number | Publication Date |
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JP2019521233A true JP2019521233A (ja) | 2019-07-25 |
JP6905300B2 JP6905300B2 (ja) | 2021-07-21 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2019502633A Active JP6905300B2 (ja) | 2016-12-20 | 2017-11-30 | Pbs樹脂組成物及びその製造方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US10815332B2 (ja) |
EP (1) | EP3560995A4 (ja) |
JP (1) | JP6905300B2 (ja) |
KR (1) | KR20190016096A (ja) |
CN (1) | CN107459785B (ja) |
WO (1) | WO2018113496A1 (ja) |
Families Citing this family (2)
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CN108414502A (zh) * | 2018-01-26 | 2018-08-17 | 昆明理工大学 | 一种测定血管中微量元素含量的方法 |
CN113512182A (zh) * | 2021-07-09 | 2021-10-19 | 万华化学集团股份有限公司 | 一种pbs树脂组合物及其制备方法 |
Citations (3)
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JP2012012578A (ja) * | 2010-06-04 | 2012-01-19 | Fujifilm Corp | ポリエステル樹脂組成物及びその製造方法、ポリエステルフィルム、並びに太陽電池発電モジュール |
JP2014193985A (ja) * | 2012-06-05 | 2014-10-09 | Mitsubishi Chemicals Corp | ポリエステル及びポリウレタンの製造方法 |
JP2015505576A (ja) * | 2012-02-06 | 2015-02-23 | 三星精密化学株式会社Samsung Fine Chemicals Co., Ltd. | ポリエステル樹脂合成用触媒及びこれを用いたポリエステル樹脂の製造方法 |
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KR100366484B1 (ko) | 1999-12-11 | 2003-01-14 | 주식회사 이래화학 | 코폴리에스테르 수지 조성물 및 그 제조방법 |
JP2006274253A (ja) | 2005-03-02 | 2006-10-12 | Daicel Chem Ind Ltd | 低分岐度高分子量脂肪族ポリエステル、その製造方法、成形品及びフィルム |
CN101671435B (zh) * | 2008-09-08 | 2011-12-28 | 上海华明高技术(集团)有限公司 | 制备聚丁二酸丁二醇酯及其共聚酯的催化剂及其制备方法 |
JP5575680B2 (ja) | 2010-03-09 | 2014-08-20 | 富士フイルム株式会社 | ポリエステル樹脂組成物及びその製造方法、ポリエステルフィルム、並びに太陽電池発電モジュール |
CN102617842B (zh) * | 2012-03-29 | 2014-06-11 | 金发科技股份有限公司 | 一种锑/钛复合催化剂及其用于制备pet共聚酯的方法 |
CN102775590B (zh) * | 2012-08-15 | 2014-11-12 | 金发科技股份有限公司 | 一种聚丁二酸丁二醇酯及其制备方法 |
CN103435794B (zh) * | 2013-07-26 | 2015-08-12 | 旭阳化学技术研究院有限公司 | 一种缩聚催化剂的制备方法、由其制备的催化剂以及以该催化剂制备pbs及其共聚物的方法 |
JP2017500380A (ja) * | 2013-12-30 | 2017-01-05 | ロッテ精密化學株式会社LOTTE Fine Chemical Co.,Ltd. | 生分解性ポリエステル樹脂製造用組成物、及び生分解性ポリエステル樹脂の製造方法 |
CN105131269B (zh) | 2015-08-17 | 2018-03-23 | 中国石油天然气集团公司 | 环保型钛‑磷配位复合催化剂的制备方法及采用该催化剂的pbs生产方法 |
CN105061744B (zh) | 2015-08-17 | 2019-04-26 | 中国石油天然气集团公司 | 聚丁二酸丁二醇酯的制备方法 |
CN106832235A (zh) | 2017-02-08 | 2017-06-13 | 新疆蓝山屯河化工股份有限公司 | 纺丝用聚丁二酸丁二醇酯及其制备方法 |
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2016
- 2016-12-20 CN CN201611182854.1A patent/CN107459785B/zh active Active
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2017
- 2017-11-30 KR KR1020197000698A patent/KR20190016096A/ko not_active IP Right Cessation
- 2017-11-30 WO PCT/CN2017/113750 patent/WO2018113496A1/zh unknown
- 2017-11-30 JP JP2019502633A patent/JP6905300B2/ja active Active
- 2017-11-30 EP EP17884479.1A patent/EP3560995A4/en active Pending
- 2017-11-30 US US16/317,648 patent/US10815332B2/en active Active
Patent Citations (3)
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JP2012012578A (ja) * | 2010-06-04 | 2012-01-19 | Fujifilm Corp | ポリエステル樹脂組成物及びその製造方法、ポリエステルフィルム、並びに太陽電池発電モジュール |
JP2015505576A (ja) * | 2012-02-06 | 2015-02-23 | 三星精密化学株式会社Samsung Fine Chemicals Co., Ltd. | ポリエステル樹脂合成用触媒及びこれを用いたポリエステル樹脂の製造方法 |
JP2014193985A (ja) * | 2012-06-05 | 2014-10-09 | Mitsubishi Chemicals Corp | ポリエステル及びポリウレタンの製造方法 |
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Publication number | Publication date |
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US20190292314A1 (en) | 2019-09-26 |
CN107459785A (zh) | 2017-12-12 |
JP6905300B2 (ja) | 2021-07-21 |
WO2018113496A1 (zh) | 2018-06-28 |
EP3560995A1 (en) | 2019-10-30 |
US10815332B2 (en) | 2020-10-27 |
EP3560995A4 (en) | 2020-10-07 |
KR20190016096A (ko) | 2019-02-15 |
CN107459785B (zh) | 2018-09-28 |
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