DK2671912T3 - Process for stabilizing polymers containing ester groups - Google Patents
Process for stabilizing polymers containing ester groups Download PDFInfo
- Publication number
- DK2671912T3 DK2671912T3 DK12170771.5T DK12170771T DK2671912T3 DK 2671912 T3 DK2671912 T3 DK 2671912T3 DK 12170771 T DK12170771 T DK 12170771T DK 2671912 T3 DK2671912 T3 DK 2671912T3
- Authority
- DK
- Denmark
- Prior art keywords
- liquid
- carbodiimides
- process according
- ester groups
- containing ester
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 20
- 229920000642 polymer Polymers 0.000 title claims description 13
- 125000004185 ester group Chemical group 0.000 title claims description 8
- 230000000087 stabilizing effect Effects 0.000 title claims description 5
- 150000001718 carbodiimides Chemical class 0.000 claims description 32
- 239000007788 liquid Substances 0.000 claims description 22
- -1 polyethylene terephthalate Polymers 0.000 claims description 12
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 10
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 10
- 239000004433 Thermoplastic polyurethane Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims description 9
- 239000004952 Polyamide Substances 0.000 claims description 7
- 239000005014 poly(hydroxyalkanoate) Substances 0.000 claims description 7
- 229920002647 polyamide Polymers 0.000 claims description 7
- 229920000903 polyhydroxyalkanoate Polymers 0.000 claims description 7
- 239000004626 polylactic acid Substances 0.000 claims description 7
- 229920001707 polybutylene terephthalate Polymers 0.000 claims description 6
- 229920002215 polytrimethylene terephthalate Polymers 0.000 claims description 6
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 4
- 229920001634 Copolyester Polymers 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 229920002725 thermoplastic elastomer Polymers 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 229920002472 Starch Polymers 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229920003023 plastic Polymers 0.000 claims 1
- 239000004033 plastic Substances 0.000 claims 1
- 235000019698 starch Nutrition 0.000 claims 1
- 239000008107 starch Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 229920005906 polyester polyol Polymers 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000013329 compounding Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- OADNRFNXACMWMJ-UHFFFAOYSA-N benzene;isocyanic acid Chemical class N=C=O.C1=CC=CC=C1 OADNRFNXACMWMJ-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 2
- BOAYBOINRWNWJC-UHFFFAOYSA-N 2-isocyanato-1,3,5-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC(C(C)C)=C(N=C=O)C(C(C)C)=C1 BOAYBOINRWNWJC-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZBVOEVQTNYNNMY-UHFFFAOYSA-N O=P1=CCCC1 Chemical class O=P1=CCCC1 ZBVOEVQTNYNNMY-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 229920003179 starch-based polymer Polymers 0.000 description 2
- 239000004628 starch-based polymer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- 229920006346 thermoplastic polyester elastomer Polymers 0.000 description 2
- IUUONVQOMMQAEH-UHFFFAOYSA-N 1-methyl-2,3-dihydro-1$l^{5}-phosphole 1-oxide Chemical compound CP1(=O)CCC=C1 IUUONVQOMMQAEH-UHFFFAOYSA-N 0.000 description 1
- JFYGXQRUYCQEFD-UHFFFAOYSA-N 2-isocyanato-5-methyl-1,3-di(propan-2-yl)benzene Chemical compound CC(C)c1cc(C)cc(C(C)C)c1N=C=O JFYGXQRUYCQEFD-UHFFFAOYSA-N 0.000 description 1
- RCSYAUOIQWIQJG-UHFFFAOYSA-N 5-ethyl-2-isocyanato-1,3-di(propan-2-yl)benzene Chemical compound CCc1cc(C(C)C)c(N=C=O)c(c1)C(C)C RCSYAUOIQWIQJG-UHFFFAOYSA-N 0.000 description 1
- 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000003819 basic metal compounds Chemical class 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- KMBWMZQYDLDUQQ-UHFFFAOYSA-N n'-[2,6-di(propan-2-yl)phenyl]methanediimine Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N=C=N KMBWMZQYDLDUQQ-UHFFFAOYSA-N 0.000 description 1
- XLDBGFGREOMWSL-UHFFFAOYSA-N n,n'-bis[2,6-di(propan-2-yl)phenyl]methanediimine Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N=C=NC1=C(C(C)C)C=CC=C1C(C)C XLDBGFGREOMWSL-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- GWLJTAJEHRYMCA-UHFFFAOYSA-N phospholane Chemical class C1CCPC1 GWLJTAJEHRYMCA-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 238000010094 polymer processing Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/82—Post-polymerisation treatment
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
- C08L75/06—Polyurethanes from polyesters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyurethanes Or Polyureas (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Polyethers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12170771.5A EP2671912B1 (de) | 2012-06-05 | 2012-06-05 | Verfahren zur Stabilisierung von Estergruppen-enthaltenden Polymeren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2671912T3 true DK2671912T3 (en) | 2015-07-27 |
Family
ID=47915278
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK12170771.5T DK2671912T3 (en) | 2012-06-05 | 2012-06-05 | Process for stabilizing polymers containing ester groups |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US20150175776A1 (https=) |
| EP (1) | EP2671912B1 (https=) |
| JP (1) | JP6174688B2 (https=) |
| KR (1) | KR102019532B1 (https=) |
| CN (1) | CN104364306A (https=) |
| BR (1) | BR112014030444B1 (https=) |
| CA (1) | CA2875157C (https=) |
| DK (1) | DK2671912T3 (https=) |
| ES (1) | ES2541410T3 (https=) |
| HU (1) | HUE026635T2 (https=) |
| IN (1) | IN2014DN10258A (https=) |
| MX (1) | MX2014014974A (https=) |
| PL (1) | PL2671912T3 (https=) |
| PT (1) | PT2671912E (https=) |
| RU (1) | RU2624299C2 (https=) |
| WO (1) | WO2013182330A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LT6658B (lt) * | 2017-12-08 | 2019-09-25 | Douglas Craig | Pet apdorojimo būdas |
| CN108912014A (zh) * | 2018-06-22 | 2018-11-30 | 上海朗亿功能材料有限公司 | 一种液体型碳化二亚胺化合物制备方法与应用 |
| EP3686239A1 (de) | 2019-01-23 | 2020-07-29 | LANXESS Deutschland GmbH | Hydrolysestabilisierte polyethylenterephthalat (pet) - haltige zusammensetzungen |
| EP4361209A1 (de) * | 2022-10-27 | 2024-05-01 | LANXESS Deutschland GmbH | Hydrolysestabilisierte polyester-haltige zusammensetzungen |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1130594B (de) | 1956-07-30 | 1962-05-30 | Du Pont | Verfahren zur Herstellung von gegebenenfalls modifizierten Polykondensationsprodukten mití¬N?C?N-Brueckengliedern |
| NL273087A (https=) * | 1960-12-31 | |||
| US3798198A (en) * | 1969-12-19 | 1974-03-19 | Shoe & Allied Trades Res Ass | Hydrolytically stabilized polyurethanes |
| US3711439A (en) * | 1970-11-27 | 1973-01-16 | Inmont Corp | Stabilized polyurethane compositions |
| DE3930845A1 (de) * | 1989-09-15 | 1991-03-28 | Hoechst Ag | Mit carbodiimiden modifizierte polyesterfasern und verfahren zu ihrer herstellung |
| DE4238046A1 (de) * | 1992-11-11 | 1994-05-19 | Basf Ag | Neue Bis-(4-substituierte-2,6-diisopropyl-phenyl)-carbodiimide, ein Verfahren zu ihrer Herstellung und ihre Verwendung sowie die zu ihrer Herstellung verwendbaren 4-substituierten 2,6-Diisopropyl-phenylisocyanate |
| US6013340A (en) * | 1995-06-07 | 2000-01-11 | Nike, Inc. | Membranes of polyurethane based materials including polyester polyols |
| DE19920276A1 (de) * | 1999-05-04 | 2000-11-09 | Basf Ag | Thermoplastische Formmassen |
| DE10161863A1 (de) | 2001-12-14 | 2003-07-03 | Basf Ag | Stabilisatorzusammensetzung II |
| JP3894846B2 (ja) * | 2002-06-19 | 2007-03-22 | 平岡織染株式会社 | 難燃メッシュシート |
| KR20050004379A (ko) * | 2003-07-02 | 2005-01-12 | 삼성전자주식회사 | 원자층 증착용 가스 공급 장치 |
| US8247156B2 (en) * | 2010-09-09 | 2012-08-21 | Xerox Corporation | Processes for producing polyester latexes with improved hydrolytic stability |
| CN102816087A (zh) * | 2011-06-10 | 2012-12-12 | 上海朗亿功能材料有限公司 | 一种胶黏剂用水解稳定剂的制备方法 |
-
2012
- 2012-06-05 DK DK12170771.5T patent/DK2671912T3/en active
- 2012-06-05 EP EP12170771.5A patent/EP2671912B1/de active Active
- 2012-06-05 HU HUE12170771A patent/HUE026635T2/en unknown
- 2012-06-05 PT PT121707715T patent/PT2671912E/pt unknown
- 2012-06-05 ES ES12170771.5T patent/ES2541410T3/es active Active
- 2012-06-05 PL PL12170771T patent/PL2671912T3/pl unknown
-
2013
- 2013-03-22 US US14/405,573 patent/US20150175776A1/en not_active Abandoned
- 2013-03-22 CA CA2875157A patent/CA2875157C/en active Active
- 2013-03-22 CN CN201380029611.2A patent/CN104364306A/zh active Pending
- 2013-03-22 BR BR112014030444-0A patent/BR112014030444B1/pt active IP Right Grant
- 2013-03-22 RU RU2014153978A patent/RU2624299C2/ru active
- 2013-03-22 WO PCT/EP2013/056158 patent/WO2013182330A1/de not_active Ceased
- 2013-03-22 KR KR1020147036864A patent/KR102019532B1/ko active Active
- 2013-03-22 IN IN10258DEN2014 patent/IN2014DN10258A/en unknown
- 2013-03-22 JP JP2015515427A patent/JP6174688B2/ja active Active
- 2013-03-22 MX MX2014014974A patent/MX2014014974A/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| EP2671912B1 (de) | 2015-04-22 |
| ES2541410T3 (es) | 2015-07-20 |
| KR20150024868A (ko) | 2015-03-09 |
| KR102019532B1 (ko) | 2019-09-06 |
| EP2671912A1 (de) | 2013-12-11 |
| PL2671912T3 (pl) | 2015-10-30 |
| CA2875157C (en) | 2020-07-14 |
| JP6174688B2 (ja) | 2017-08-02 |
| HUE026635T2 (en) | 2016-07-28 |
| RU2624299C2 (ru) | 2017-07-03 |
| CN104364306A (zh) | 2015-02-18 |
| RU2014153978A (ru) | 2016-07-27 |
| BR112014030444A2 (pt) | 2017-06-27 |
| US20150175776A1 (en) | 2015-06-25 |
| MX2014014974A (es) | 2015-03-13 |
| JP2015518911A (ja) | 2015-07-06 |
| CA2875157A1 (en) | 2013-12-12 |
| WO2013182330A1 (de) | 2013-12-12 |
| BR112014030444B1 (pt) | 2021-02-17 |
| IN2014DN10258A (https=) | 2015-08-07 |
| PT2671912E (pt) | 2015-08-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DK2997010T3 (en) | NEW CARBODIIMIDES WITH END-TENDED CARBAMID AND / OR INCORRECT GROUPS, METHOD OF PRODUCING IT AND USING IT | |
| DK2671912T3 (en) | Process for stabilizing polymers containing ester groups | |
| US9199925B2 (en) | Carbodiimides from trisubstituted aromatic isocyanates, a method for producing same, and the use of same | |
| KR102859380B1 (ko) | 폴리에스테르 수지 개질제 및 그 제조 방법, 및 폴리에스테르 수지 조성물 | |
| CA2875737C (en) | Novel carbodiimide-containing compositions, a process for preparation thereof and use thereof | |
| CN111471282B (zh) | 包含聚对苯二甲酸乙二醇酯和至少一种单体碳二亚胺的组合物及其生产方法和用途 | |
| KR102834191B1 (ko) | 폴리카르보디이미드 화합물, 및, 이것을 이용한 폴리에스테르 수지 조성물 및 폴리에스테르 수지 개질제 | |
| KR20240117160A (ko) | 중합체 카보다이이미드, 이의 제조 방법 및 이의 용도 |