KR100840997B1 - 폴리우레탄폼 제조용 폴리에테르폴리올의 제조방법 - Google Patents
폴리우레탄폼 제조용 폴리에테르폴리올의 제조방법 Download PDFInfo
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- KR100840997B1 KR100840997B1 KR1020060096996A KR20060096996A KR100840997B1 KR 100840997 B1 KR100840997 B1 KR 100840997B1 KR 1020060096996 A KR1020060096996 A KR 1020060096996A KR 20060096996 A KR20060096996 A KR 20060096996A KR 100840997 B1 KR100840997 B1 KR 100840997B1
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- amine
- catalyst
- polyol
- polyurethane foam
- reaction
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- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
-
- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4244—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups
- C08G18/4247—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups derived from polyols containing at least one ether group and polycarboxylic acids
- C08G18/4252—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups derived from polyols containing at least one ether group and polycarboxylic acids derived from polyols containing polyether groups and polycarboxylic acids
-
- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
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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)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
<아미노 알콜의 합성예>
CH2CH20 - CH2Cl + CH3·CH3NH →
(에피클로로히드린) (디메틸아민)
CH3CH3NCH2 - CH(OH)-CH2Cl
(디메틸아민-3클로로-2프로판올)
여기에 디에탄올아민 88g을 넣고 질소 치환한 후 반응기의 반응온도를 120℃ 까지 승온한 후 2시간동안 반응시키면 1-디메틸아민-3-아미노디에탄올-2-프로판올[CH3CH3N-CH2-CH(OH)-CH2-N-(CH2CH2OH)2] 198g이 얻어진다. 반응기에 48% 수용액 KOH 104.2g을 넣은 후 반응온도를 112℃까지 감온하고 3시간 동안 진공펌프로 반응기에 있는 수분을 1000ppm이하가 될 때까지 제거한다. 염화칼륨을 압력 필터를 이용하여 제거한다.
CH3CH3N-CH2-CH(OH) - CH2Cl + (HOCH2CH2)NH →
(디메틸아민-3클로로-2프로판올) (모노에탄올아민)
(CH3CH3N-CH2-CH(OH)-CH2)2-NCH2CH2OH
[디(1-디메틸아민-프로판올)-에탄올아민]
반응기에 48% 수용액 KOH 104.2g을 넣은 후 반응온도를 112℃까지 감온하고 3시간 동안 진공펌프로 반응기에 있는 수분을 1000ppm이하가 될 때까지 제거한다. 염화칼륨을 압력 필터를 사용하여 제거한다.
<폴리올 제조예>
실시예 2는 출발물질로 1-디메틸아민-3-아미노디에탄올-2-프로판올 대신에 디(1-디메틸아민-2-프로판올)-에탄올아민을 사용하는 것과 PO의 사용량을 변경한 것을 제외하고는 실시예 1과 같은 방법으로 실시하였다.
상기 실시예 1~4 및 비교예 1,2에서 얻어진 폴리에테르폴리올의 물성값은 아래 [표 1]에 나타낸 바와 같다.
[표 1]
실시예1 | 실시예2 | 실시예3 | 실시예4 | 비교예 1 | 비교예 2 | |
OHV | 56.3 | 55.8 | 28.4 | 28.3 | 56.1 | 27.9 |
Mw | 2973 | 2016 | 5926 | 5946 | 3000 | 6032 |
EO,% | 8.6% | 8.5% | 16.4% | 16.5% | 8.5% | 16.6% |
아민값, (MgKOH/g) | 36.5 | 37.7 | 18.1 | 18.5 | 0 | 0 |
<폴리우레탄폼 제조예>
[표 2]
실시예5 | 실시예6 | 비교예3 | |
원부재료 | |||
Polyol, , H2O T-9(촉매) A-1(발포조제) BF-2730 메틸렌클로라이드 TDI | 실시예1/비교예1 20/80 3.7 0.26 - 1.2 5 115 | 실시예2/비교예1 10/90 3.7 0.26 - 1.2 5 115 | 비교예1 100 3.7 0.26 0.1 1.2 5 115 |
Foam 반응성 | |||
Crime time,(sec) Rise Time,(sec) | 13 80 | 12 83 | 12 81 |
Foam 물성 | |||
밀도, (kg/m3) ILD 25%, (kg/314cm2) 65%, (kg/314cm2) 인열, (kg/cm) 인장, (kg/cm2) 신율, (%) 통기성,(Ft3/min) 반발탄성,(%) Amine함량(ppm) | 26.3 22.3 45.3 0.69 0.99 117 1.48 31 - | 27.2 21.9 45.2 0.68 0.94 112 1.42 32 - | 27 21.7 44.9 0.64 0.94 105 1.85 41 2 |
T-9 : 옥틸산주석
A-1 : 아민촉매(비스(디메틸아미노에틸)에테르)
BF-2730 : 실리콘 오일
TDI : 톨루엔디이소시아네이트
[표 3]
실시예7 | 실시예8 | 비교예4 | |
원부재료 | |||
Polyol, Y-7325N H2O 트리에틸렌디아민 EF-600 T-12 DEOA 실리콘오일(소포제) MDI | 실시예5/비교예2 50/30 20 3.5 - 0.03 0.1 MC50 | 실시예6/비교예2 30/50 20 3.5 - 0.03 0.1 MC50 | 비교예2 80 20 3.5 0.3/0.14/0.2 - - 0.7 0.8 MC50 |
Foam 물성 | |||
밀도,(kg/m3) ILD 25%, (kg/314cm2) ILD 65%,(kg/314cm2) 인열, (kg/cm) 인장, (kg/cm2) 신율, (%) 반발탄성, (%) 압축영구줄음율, (%, Dry) 반복압축변형율,(%) 25% Loss 50% Loss 65% Loss 두께 Loss Amine함량(ppm) | 34.5 19.3 61.5 0.93 1.18 131 53 68.0 33.6 27.4 18.8 8.6 - | 35.0 19.5 62.3 0.96 1.29 128 53 65.8 33.7 27.2 17.5 9.8 - | 34.6 19.6 61.4 0.96 1.22 129 52 67.2 33.7 27.4 18.2 9.3 7 |
T-12 : 디부틸틴라우레이트 (dibutyl tindilaurate)
Y-7325N : 폴리올(SKC사 제품 상품명)
EF-600 : 실리콘오일
DEOA : 디에탄올아민
Claims (3)
- 폴리우레탄 폼 제조용 폴리에테르폴리올의 제조방법에 있어서, 2차아민을 할로겐화 에폭시화합물과 반응시켜 2~3개의 아미노기를 갖는 아미노알콜을 얻고 이를 중합개시제로 하여 촉매하에서 에폭시 화합물을 에폭사이드 중합반응시켜 얻어지는 분자내에 2~3개의 아민기를 갖는 폴리우레탄폼 제조용 폴리에테르폴리올의 제조방법.
- 제 1항에 있어서,2차아민이 디메틸아민, 디에틸아민, 디이소프로필아민, 디부틸아민, 디이소부틸아민, 디-sec-부틸아민, 디페닐아민, 디사이클로헥실아민, 3-메틸디페닐아민 중에서 선택되는 것이고, 할로겐화 에폭시 화합물이 에피클로로히드린, 에피브로모히드린, 에피플루오로히드린 중에서 선택되는 것이고, 아미노알콜이 메타놀아민, 에탄올아민, 프로판올아민, 이소프로판올아민, 부탄올아민, 이소부탄올아민, sec-부탄올아민, t-부탄올아민, 펜타놀아민, 2-아미노-1-페닐에탄올, 디메탄올아민, 디에탄올아민, 디이소프로판올아민, 디이소부탄올아민, 디-sec-부탄올아민, 디부탄올아민, 디펜타놀아민, N-메틸에탄올아민 중에서 선택되는 것이고, 촉매가 KOH이고, 에폭시 화합물이 산화에틸렌 또는 산화프로필렌중에서 선택되는 폴리우레탄폼 제조용 폴리에테르폴리올의 제조방법.
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Cited By (1)
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KR101922549B1 (ko) * | 2017-06-15 | 2018-11-28 | 순천대학교 산학협력단 | 폴리에테르 폴리올의 제조방법 |
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CN103113872A (zh) * | 2013-02-05 | 2013-05-22 | 南充市巨星化工有限责任公司 | 采油用高效降压增注剂及其生产方法 |
CN109180897A (zh) * | 2018-07-19 | 2019-01-11 | 中国林业科学研究院林产化学工业研究所 | 自催化型环氧树脂基多元醇水分散体及其制备方法 |
CN114044869B (zh) * | 2021-12-02 | 2023-03-24 | 万华化学集团股份有限公司 | 一种仲胺类扩链交联剂及一种聚氨酯弹性材料 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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KR900000408A (ko) * | 1988-06-28 | 1990-01-30 | 쥬르퀸 루시엔 | 유연한 폴리우레탄 폼의 제조방법 |
US5889068A (en) | 1997-07-24 | 1999-03-30 | Bayer Corporation | Water blown polyurethane soling systems |
US6562880B1 (en) | 2002-04-17 | 2003-05-13 | Bayer Corporation | Polyurethane or polyisocyanurate foams blown with hydrofluorocarbons and carbon atoms |
KR20050078969A (ko) * | 2004-02-03 | 2005-08-08 | 에스케이씨 주식회사 | 광학 입체 규칙성을 갖는 폴리에테르폴리올 및 그의제조방법 |
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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KR900000408A (ko) * | 1988-06-28 | 1990-01-30 | 쥬르퀸 루시엔 | 유연한 폴리우레탄 폼의 제조방법 |
US5889068A (en) | 1997-07-24 | 1999-03-30 | Bayer Corporation | Water blown polyurethane soling systems |
US6562880B1 (en) | 2002-04-17 | 2003-05-13 | Bayer Corporation | Polyurethane or polyisocyanurate foams blown with hydrofluorocarbons and carbon atoms |
KR20050078969A (ko) * | 2004-02-03 | 2005-08-08 | 에스케이씨 주식회사 | 광학 입체 규칙성을 갖는 폴리에테르폴리올 및 그의제조방법 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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KR101922549B1 (ko) * | 2017-06-15 | 2018-11-28 | 순천대학교 산학협력단 | 폴리에테르 폴리올의 제조방법 |
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