KR20020063212A - 폴리트리메틸렌 에테르 글리콜의 연속 제조 방법 - Google Patents
폴리트리메틸렌 에테르 글리콜의 연속 제조 방법 Download PDFInfo
- Publication number
- KR20020063212A KR20020063212A KR1020027007493A KR20027007493A KR20020063212A KR 20020063212 A KR20020063212 A KR 20020063212A KR 1020027007493 A KR1020027007493 A KR 1020027007493A KR 20027007493 A KR20027007493 A KR 20027007493A KR 20020063212 A KR20020063212 A KR 20020063212A
- Authority
- KR
- South Korea
- Prior art keywords
- propanediol
- reactor
- column
- polycondensation
- reactant
- Prior art date
Links
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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/009—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping in combination with chemical reactions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J10/00—Chemical processes in general for reacting liquid with gaseous media other than in the presence of solid particles, or apparatus specially adapted therefor
- B01J10/002—Chemical processes in general for reacting liquid with gaseous media other than in the presence of solid particles, or apparatus specially adapted therefor carried out in foam, aerosol or bubbles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J10/00—Chemical processes in general for reacting liquid with gaseous media other than in the presence of solid particles, or apparatus specially adapted therefor
- B01J10/007—Chemical processes in general for reacting liquid with gaseous media other than in the presence of solid particles, or apparatus specially adapted therefor in the presence of catalytically active bodies, e.g. porous plates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/245—Stationary reactors without moving elements inside placed in series
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
- B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
- B01J8/04—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds the fluid passing successively through two or more beds
- B01J8/0446—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds the fluid passing successively through two or more beds the flow within the beds being predominantly vertical
- B01J8/0449—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds the fluid passing successively through two or more beds the flow within the beds being predominantly vertical in two or more cylindrical beds
- B01J8/0453—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds the fluid passing successively through two or more beds the flow within the beds being predominantly vertical in two or more cylindrical beds the beds being superimposed one above the other
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00017—Controlling the temperature
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
- B01J2208/00008—Controlling the process
- B01J2208/00017—Controlling the temperature
- B01J2208/00106—Controlling the temperature by indirect heat exchange
- B01J2208/00115—Controlling the temperature by indirect heat exchange with heat exchange elements inside the bed of solid particles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00002—Chemical plants
- B01J2219/00027—Process aspects
- B01J2219/00033—Continuous processes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00164—Controlling or regulating processes controlling the flow
- B01J2219/00166—Controlling or regulating processes controlling the flow controlling the residence time inside the reactor vessel
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00182—Controlling or regulating processes controlling the level of reactants in the reactor vessel
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/18—Details relating to the spatial orientation of the reactor
- B01J2219/185—Details relating to the spatial orientation of the reactor vertical
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Vigreux 컬럼에서의 3G 연속 중합 | |||||||
운전 | 공급 물질 | 공급 속도(㎖/분) | 컬럼 온도(℃) | 축합물 질량(g) | R.I.* | 수율 | 체류 시간(분) |
1 | 3G+H2SO4(1%) | 1.24 | 200 | 0.90 | 1.3400 | 2.1% | 0.75 |
2 | 3G+H2SO4(1%) | 1.20 | 212 | 2.21 | 1.3397 | 6.0% | 1.13 |
3 | 3G+H2SO4(1%) | 1.08 | 217 | 2.60 | 1.3394 | 8.0% | 1.00 |
4 | 3G+H2SO4(1%) | 0.99 | 216 | 3.24 | 1.3423 | 10.9% | 1.17 |
*R.I.은 25℃에서의 축합물의 굴절 지수이다. 물의 R.I.는 25℃에서 1.3327이다. |
유리 비드 충전 컬럼에서의 3G 연속 중합 | |||||||
운전 | 공급 물질 | 공급 속도(㎖/분) | 컬럼 온도(℃) | 축합물 질량(g) | R.I.(a) | 수율 | 체류 시간(분) |
5 | 3G+H2SO4(1%) | 1.32 | 200 | 6.43 | 1.3365 | 16.2% | 1.42 |
6 | 3G+H2SO4(1%) | 1.32 | 208 | 10.10 | 1.3383 | 25.5% | 1.25 |
7 | 3G+H2SO4(1%) | 1.20 | 219 | 7.71 | 1.3395 | 21.4% | 1.72 |
8 | 3G+H2SO4(1%) | 1.13 | 214 | 7.16 | 1.3388 | 21.1% | 1.72 |
9 | 3G+H2SO4(1%) | 1.13 | 208 | 7.00 | 1.3385 | 20.7% | 1.93 |
(a)R.I.은 25℃에서의 축합물의 굴절 지수이다. 물의 R.I.는 25℃에서 1.3327이다. |
3G 폴리올 연속 중합 - 1단 컬럼/다중 통과 실험(a) | ||||||
중합 운전 | 공급 물질 | 공급 속도(㎖/분) | 컬럼 온도(℃) | 축합물 질량(g) | 누적 수율 | 체류 시간(분) |
10 | 3G+H2SO4(1%) | 1.07 | 210 | 4.36 | 10.9% | 1.63 |
11 | 운전 10의 생성물 | 1.06 | 211 | 5.07 | 23.5% | 1.33 |
12 | 운전 11의 생성물 | 1.12 | 210 | 4.98 | 35.9% | 1.53 |
13 | 운전 12의 생성물 | 1.08 | 212 | 4.60 | 47.4% | 1.40 |
14 | 운전 13의 생성물 | 0.99 | 216 | 1.87 | 52.0% | 1.28 |
(a): 사용된 1단 컬럼은 실시예 2에서 설명한 바와 같은 유리 비드 충전 컬럼이다. |
3G 폴리올 연속 중합 - 다단 컬럼 실험(a) | ||||||
중합 운전 | 공급 물질 | 공급 속도(㎖/분) | 설정 온도(℃) | 축합물 질량(g) | 수율 | 체류 시간(분) |
15 | 3G+H2SO4(1%) | 1.12 | 210 | 15.66 | 46.9% | 12.00 |
16 | 3G+H2SO4(1%) | 0.98 | 210 | 18.37 | 63.0% | 12.45 |
17 | 3G+H2SO4(2.5%) | 1.06 | 210 | 30.37 | 96.3% | 11.13 |
18 | 3G+H2SO4(4.0%) | 1.06 | 210 | 37.98 | 109% | 10.00 |
올리고머 | n | MWig/mol | 시료-운전 6 | 시료-운전 12 | 시료-운전 13 | 시료-운전 14 | 시료-운전 15 | |||||
ni(%)(b) | ni *MWi | ni(%)(b) | ni *MWi | ni(%)(b) | ni *MWi | ni(%)(b) | ni *MWi | ni(%)(b) | ni *MWi | |||
3G | -- | 76.095 | 60.600 | 46.114 | 42.000 | 31.960 | 23.900 | 18.187 | 15.200 | 11.566 | 27.800 | 21.154 |
이량체 | 2 | 134.175 | 17.400 | 23.346 | 25.500 | 34.215 | 24.400 | 32.739 | 22.000 | 29.519 | 24.000 | 32.202 |
삼량체 | 3 | 192.255 | 4.440 | 8.536 | 10.200 | 19.610 | 14.100 | 27.108 | 15.200 | 29.223 | 12.800 | 24.609 |
사량체 | 4 | 250.335 | 1.790 | 4.481 | 4.160 | 10.414 | 7.960 | 19.927 | 9.500 | 23.782 | 6.610 | 16.547 |
오량체 | 5 | 308.415 | 0.724 | 2.233 | 1.660 | 5.120 | 4.060 | 12.522 | 5.200 | 16.038 | 3.240 | 9.993 |
육량체 | 6 | 366.495 | 0.401 | 1.470 | 0.752 | 2.756 | 1.990 | 7.293 | 2.910 | 10.665 | 1.720 | 6.304 |
칠량체 | 7 | 424.575 | 0.320 | 1.359 | 0.393 | 1.669 | 1.070 | 4.543 | 1.580 | 6.708 | 1.110 | 4.713 |
팔량체 | 8 | 482.655 | 0.150 | 0.724 | 0.160 | 0.772 | 0.410 | 1.979 | 0.700 | 3.379 | 0.500 | 2.413 |
3G제외 총합 | 25.225 | 42.149 | 42.825 | 74.555 | 53.990 | 106.110 | 57.090 | 119.313 | 49.980 | |||
3G포함 총합 | 85.825 | 88.262 | 84.825 | 106.515 | 77.890 | 124.297 | 72.290 | 130.879 | 77.780 | 117.935 | ||
3G제외 Mn | (g/mol) | 167.091 | 174.093 | 196.537 | 208.990 | 193.638 | ||||||
3G포함 Mn | (g/mol) | 102.840 | 125.570 | 159.580 | 181.047 | 151.626 |
3G 폴리올 중합배치식 대 연속식 컬럼 공정 | ||||
중합 | 촉매 퍼센트(a) | 체류 시간(분) | 중합체 점도(cPoise) | 중합체 분자량(Mn) |
배치식 실험 a | 1.0% | 240.00 | 226.3 | 417(a) |
배치식 실험 b | 1.0% | 240.00 | 352.3 | 680(a) |
연속식 (운전 15) | 1.0% | 12.00 | 79.4 | 193.6(b), 179(a) |
연속식 (운전 17) | 2.5% | 11.13 | 341.0 | 500(a) |
연속식 (운전 18) | 4.0% | 10.00 | 599.3 | 690(a) |
(a) 핵 자기 공명 분석(b) 기체 크로마토그래피 분석 |
3G 폴리올 연속 중합 - 다단 컬럼/병류 상향류식 | ||||
중합 운전 | 산 농도 | 중합 속도(㎏/hr) | 컬럼 온도(℃) | 중합체의 수평균 분자량 |
1 | 1% H2SO4 | 3.82 | 180 | 252 |
2 | 1% H2SO4 | 3.05 | 180 | 546 |
3 | 1% H2SO4 | 2.29 | 180 | 792 |
4 | 1% H2SO4 | 3.82 | 190 | 852 |
5 | 1% H2SO4 | 0.8 | 175, 190, 180 | 1680 |
6 | 1% H2SO4 | 0.8 | 180 | 1801 |
7 | 1% H2SO4 | 0.8 | 180, 180, 190 | 1898 |
Claims (18)
- (a) 1,3-프로판디올 반응물 및 중축합 촉매를 제공하는 단계; 및(b) 1,3-프로판디올 반응물을 폴리트리메틸렌 에테르 글리콜로 연속적으로 중축합시키는 단계를 포함하는 폴리트리메틸렌 에테르 글리콜의 제조 방법.
- 제1항에 있어서, 중축합이 150 내지 250℃의 온도에서 수행되는 방법.
- 제1항에 있어서, 온도가 160 내지 210℃인 방법.
- 제1항 내지 제3항 중 어느 한 항에 있어서, 중축합이 500 mmHg 미만의 압력에서 수행되는 방법.
- 제4항에 있어서, 압력이 250 mmHg 미만인 방법.
- 제1항 내지 제5항 중 어느 한 항에 있어서, 1,3-프로판디올 반응물이 1,3-프로판디올 및(또는) 1,3-프로판디올의 이량체 및 삼량체와 이들의 혼합물로 이루어진 군 중에서 선택되는 것인 방법.
- 제1항 내지 제5항 중 어느 한 항에 있어서, 1,3-프로판디올 반응물이 1,3-프로판디올 및 적어도 90 중량%의 1,3-프로판디올을 함유하는 혼합물로 이루어진 군 중에서 선택되는 것인 방법.
- 제1항 내지 제5항 중 어느 한 항에 있어서, 1,3-프로판디올 반응물이 1,3-프로판디올인 방법.
- 제1항 내지 제8항 중 어느 한 항에 있어서, 반응기가 3 내지 30단을 갖는 것인 방법.
- 제1항 내지 제9항 중 어느 한 항에 있어서, 반응기가 8 내지 15단을 갖는 것인 방법.
- 제1항 내지 제10항 중 어느 한 항에 있어서, 중축합이 상향 병류 (up-flow co-current) 컬럼 반응기에서 수행되고, 1,3-프로판디올 반응물 및 폴리트리메틸렌 에테르 글리콜이 기체 및 증기의 유동과 상향 병류로 유동하는 방법.
- 제11항에 있어서, 1,3-프로판디올 반응물이 다수 위치에서 반응기에 공급되는 방법.
- 제11항 또는 제12항에 있어서, 반응의 부산물로서 생성되는 스팀 (수증기)의 적어도 일부가 하나 이상의 중간단에서 반응기로부터 제거되는 방법.
- 제1항 내지 제10항 중 어느 한 항에 있어서, 중축합이, 1,3-프로판디올 반응물 및 폴리트리메틸렌 에테르 글리콜이 기체 및 증기의 유동에 대해 반대 방향으로 유동하는 역류 (counter current) 수직형 반응기에서 수행되는 방법.
- 제1항 내지 제14항 중 어느 한 항에 있어서, 1,3-프로판디올 반응물이 다수 위치에서 반응기에 공급되는 방법.
- 제1항 내지 제15항 중 어느 한 항에 있어서, 중축합이 먼저 하나 이상의 예비중합 반응기에서 수행된 후 컬럼 반응기에서 계속 수행되고, 1,3-프로판디올 반응물이 90 중량% 이상의 1,3-프로판디올을 포함하며, 예비중합 반응기에서 1,3-프로판디올이 촉매를 사용하여 5 이상의 중합도로 중합되는 방법.
- 제16항에 있어서, 하나 이상의 예비중합 반응기에서 1,3-프로판디올이 촉매를 사용하여 10 이상의 중합도로 중합되고, 컬럼 반응기가 3 내지 30단을 포함하는 것인 방법.
- 액체 상태의 1종 이상의 반응물을 상향류 컬럼 반응기에서 반응시키는 단계,및 기체 또는 증기상 부산물을 형성시키고, 이 기체 또는 증기상 부산물을 상단 및 하나 이상의 중간단으로부터 연속적으로 제거하는 단계를 포함하는 연속식 다단 방법.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US17212699P | 1999-12-17 | 1999-12-17 | |
US60/172,126 | 1999-12-17 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20020063212A true KR20020063212A (ko) | 2002-08-01 |
KR100677808B1 KR100677808B1 (ko) | 2007-02-05 |
Family
ID=22626474
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020027007493A KR100677808B1 (ko) | 1999-12-17 | 2000-12-15 | 폴리트리메틸렌 에테르 글리콜의 연속 제조 방법 |
Country Status (11)
Country | Link |
---|---|
US (2) | US6720459B2 (ko) |
EP (1) | EP1237835B1 (ko) |
JP (1) | JP4638646B2 (ko) |
KR (1) | KR100677808B1 (ko) |
CN (1) | CN1238317C (ko) |
AT (1) | ATE340154T1 (ko) |
AU (1) | AU2270901A (ko) |
CA (1) | CA2389800C (ko) |
DE (1) | DE60030880T2 (ko) |
MX (1) | MXPA02005949A (ko) |
WO (1) | WO2001044150A2 (ko) |
Families Citing this family (114)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2795735B1 (fr) | 1999-07-01 | 2001-09-07 | Univ Toulouse | Derives citrullines de la fibrine et leur utilisation pour le diagnostic ou le traitement de la polyarthrite rhumatoide |
US6949617B2 (en) * | 2003-05-09 | 2005-09-27 | Acushnet Company | Golf balls comprising chiral diols or chiral cyclic ethers |
AU2581401A (en) | 1999-12-17 | 2001-06-25 | E.I. Du Pont De Nemours And Company | Production of polytrimethylene ether glycol and copolymers thereof |
WO2001044150A2 (en) * | 1999-12-17 | 2001-06-21 | E.I. Du Pont De Nemours And Company | Continuous process for the preparation of polytrimethylene ether glycol |
US6599625B2 (en) | 2001-10-31 | 2003-07-29 | E. I. Du Pont De Nemours And Company | Polyether ester elastomer comprising polytrimethylene ether ester soft segment and trimethylene ester hard segment |
US6562457B1 (en) | 2001-10-31 | 2003-05-13 | E. I. Du Pont De Nemours And Company | Polyether ester elastomer comprising polytrimethylene ether ester soft segment and tetramethylene ester hard segment |
US6590065B1 (en) | 2001-12-10 | 2003-07-08 | E. I. Du Pont De Nemours And Company | Polytrimethylene ether ester amide and use thereof |
US6946539B2 (en) * | 2002-08-09 | 2005-09-20 | E. I. Du Pont De Nemours And Company | Polyurethane and polyurethane-urea comprised of poly(trimethylene-ethylene ether) glycol soft segment |
US6852823B2 (en) | 2002-08-09 | 2005-02-08 | E. I. Du Pont De Nemours And Company | Polyurethane and polyurethane-urea elastomers from polytrimethylene ether glycol |
US20040030095A1 (en) * | 2002-08-09 | 2004-02-12 | Sunkara Hari B. | Poly(trimethylene-ethylene ether) glycols |
US6608168B1 (en) | 2002-08-09 | 2003-08-19 | E. I. Du Pont De Nemours And Company | Polytrimethylene ether esters |
US6979492B2 (en) * | 2002-08-09 | 2005-12-27 | E. I. Du Pont De Nemours And Company | Thermoplastic elastomer comprising poly(trimethylene-ethylene ether) soft segment and polyamide hard segment |
US6905765B2 (en) * | 2002-08-09 | 2005-06-14 | E.I. Du Pont De Nemours And Company | Polyether ester elastomers comprising poly(trimethylene-ethylene ether) ester soft segment and alkylene ester hard segment |
US6875514B2 (en) | 2003-03-21 | 2005-04-05 | E. I. Du Pont De Nemours And Company | Coating composition containing polytrimethylene ether diol useful as a primer composition |
KR20050120654A (ko) * | 2003-03-21 | 2005-12-22 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 폴리트리메틸렌 에테르 디올 함유 피복 조성물 |
US7323539B2 (en) * | 2003-05-06 | 2008-01-29 | E. I. Du Pont De Nemours And Company | Polytrimethylene ether glycol and polytrimethylene ether ester with excellent quality |
US7342142B2 (en) * | 2003-05-06 | 2008-03-11 | E.I. Du Pont De Nemours And Company | Hydrogenation of polytrimethylene ether glycol |
US20040225107A1 (en) * | 2003-05-06 | 2004-11-11 | Sunkara Hari Babu | Polytrimethylene ether glycol with excellent quality from biochemically-derived 1,3-propanediol |
US7745668B2 (en) * | 2003-05-06 | 2010-06-29 | E. I. Du Pont De Nemours And Company | Processes for reducing color in polytrimethylene ether glycol polymers |
BRPI0410686A (pt) | 2003-05-06 | 2006-06-20 | Du Pont | processo e composição |
JP4814794B2 (ja) * | 2003-05-06 | 2011-11-16 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 生物学的に生産された1,3−プロパンジオールの精製 |
US7009082B2 (en) * | 2003-05-06 | 2006-03-07 | E.I. Du Pont De Nemours And Company | Removal of color bodies from polytrimethylene ether glycol polymers |
US7084311B2 (en) * | 2003-05-06 | 2006-08-01 | E. I. Du Pont De Nemours And Company | Hydrogenation of chemically derived 1,3-propanediol |
CN1816509A (zh) * | 2003-05-08 | 2006-08-09 | 三菱化学株式会社 | 1,3-丙二醇的制备方法 |
US7144958B2 (en) * | 2003-05-21 | 2006-12-05 | E. I. Du Pont De Nemours And Company | Articles prepared from compositions modified with organic fiber micropulp |
US7179769B2 (en) * | 2003-07-17 | 2007-02-20 | E. I. Du Pont De Nemours And Company | Poly (trimethylene-ethylene ether) glycol lube oils |
US20080103217A1 (en) * | 2006-10-31 | 2008-05-01 | Hari Babu Sunkara | Polyether ester elastomer composition |
US7074969B2 (en) * | 2004-06-18 | 2006-07-11 | E.I. Du Pont De Nemours And Company | Process for preparation of polytrimethylene ether glycols |
US7422795B2 (en) * | 2004-06-21 | 2008-09-09 | E.I. Du Pont De Nemours And Company | Polytrimethylene ether ester elastomer flexible films |
WO2006001482A1 (ja) * | 2004-06-29 | 2006-01-05 | Mitsubishi Chemical Corporation | ポリエーテルポリオールの製造方法 |
US7629396B2 (en) * | 2005-02-23 | 2009-12-08 | E.I. Du Pont De Nemours And Company | Silicon-containing polytrimethylene homo- for copolyether composition |
US20060189711A1 (en) * | 2005-02-23 | 2006-08-24 | Ng Howard C | Silicon-containing polytrimethylene homo- or copolyether composition |
US7282159B2 (en) * | 2005-02-25 | 2007-10-16 | E.I. Dupont De Nemours And Company | Process for heat transfer utilizing a polytrimethylene ether glycol or polytrimethylene ether ester glycol based heat transfer fluid |
US7476344B2 (en) * | 2005-02-25 | 2009-01-13 | E.I. Du Pont De Nemours | Electrical apparatuses containing polytrimethylene homo- or copolyether glycol based electrical insulation fluids |
US7413677B2 (en) * | 2005-02-25 | 2008-08-19 | E. I. Du Pont De Nemours And Company | Process for heat transfer utilizing a polytrimethylene homo- or copolyether glycol based heat transfer fluid |
US7638591B2 (en) * | 2005-04-08 | 2009-12-29 | E. I. Du Pont De Nemours And Company | Polyester elastomer and compositions thereof |
US7244790B2 (en) * | 2005-05-02 | 2007-07-17 | E.I. Du Pont De Nemours And Company | Thermoplastic elastomer blend, method of manufacture and use thereof |
WO2006121111A1 (ja) * | 2005-05-13 | 2006-11-16 | Mitsubishi Chemical Corporation | ポリエーテルポリオールの製造方法 |
US7161045B1 (en) | 2005-08-16 | 2007-01-09 | E. I. Du Pont De Nemours And Company | Process for manufacture of polytrimethylene ether glycol |
US7157607B1 (en) * | 2005-08-16 | 2007-01-02 | E. I. Du Pont De Nemours And Company | Manufacture of polytrimethylene ether glycol |
US8271682B2 (en) * | 2005-09-16 | 2012-09-18 | Sendori, Inc. | Enhancements for domain name leasing marketplace |
US7357985B2 (en) * | 2005-09-19 | 2008-04-15 | E.I. Du Pont De Nemours And Company | High crimp bicomponent fibers |
US7405330B2 (en) * | 2005-09-22 | 2008-07-29 | E.I. Du Pont De Nemours And Company | Preparation of polytrimethylene ether glycol and copolymers thereof |
US7625941B2 (en) * | 2005-09-22 | 2009-12-01 | E.I. Du Pont De Nemours And Company | Ionic liquids |
US7544813B2 (en) * | 2005-09-22 | 2009-06-09 | E.I. Du Pont De Nemours And Company | Ionic liquids |
EP1940914B1 (en) * | 2005-09-22 | 2009-05-13 | E.I. Du Pont De Nemours And Company | Preparation of polytrimethylene ether glycol and copolymers thereof |
WO2007052697A1 (ja) * | 2005-11-02 | 2007-05-10 | Mitsubishi Chemical Corporation | ポリアルキレンエーテルグリコール及びその製造方法 |
US20070129524A1 (en) * | 2005-12-06 | 2007-06-07 | Sunkara Hari B | Thermoplastic polyurethanes comprising polytrimethylene ether soft segments |
US7388115B2 (en) * | 2006-01-20 | 2008-06-17 | E. I. Du Pont De Nemours And Company | Manufacture of polytrimethylene ether glycol |
US7164046B1 (en) | 2006-01-20 | 2007-01-16 | E. I. Du Pont De Nemours And Company | Manufacture of polytrimethylene ether glycol |
US20070203371A1 (en) * | 2006-01-23 | 2007-08-30 | Sunkara Hari B | Process for producing polytrimethylene ether glycol |
US7888431B2 (en) * | 2006-02-10 | 2011-02-15 | E.I. Du Pont De Nemours & Co. | Coating compositions having improved early hardness |
JP5258756B2 (ja) * | 2006-05-17 | 2013-08-07 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | パーソナルケア組成物 |
US20080039582A1 (en) * | 2006-07-28 | 2008-02-14 | Hari Babu Sunkara | Polytrimethylene ether-based polyurethane ionomers |
US20080175875A1 (en) * | 2006-09-25 | 2008-07-24 | Hari Babu Sunkara | Cosmetic compositions |
US7531593B2 (en) | 2006-10-31 | 2009-05-12 | E.I. Du Pont De Nemours And Company | Thermoplastic elastomer blend composition |
US20080108845A1 (en) * | 2006-11-07 | 2008-05-08 | Hari Babu Sunkara | Polytrimethylene ether glycol esters |
US20080135662A1 (en) * | 2006-12-06 | 2008-06-12 | Chang Jing C | Melt-spun elastoester multifilament yarns |
US20090131625A1 (en) * | 2007-11-21 | 2009-05-21 | Kurian Joseph V | Processes for making elastomeric polyester esters from post-consumer polyester |
US20080242831A1 (en) * | 2007-03-27 | 2008-10-02 | Yanhui Niu | Lower-color polytrimethylene ether glycol using zero-valent metals |
US7714174B2 (en) * | 2007-03-27 | 2010-05-11 | E. I. Du Pont De Nemours And Company | Lower-color polytrimethylene ether glycol using hydride compounds |
US8703681B2 (en) | 2007-08-24 | 2014-04-22 | E I Du Pont De Nemours And Company | Lubrication oil compositions |
KR20100061813A (ko) * | 2007-08-24 | 2010-06-09 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 윤활유 조성물 |
MX2010002153A (es) * | 2007-08-24 | 2010-03-18 | Du Pont | Composiciones de aceite de lubricacion. |
WO2009029470A1 (en) * | 2007-08-24 | 2009-03-05 | E. I. Du Pont De Nemours And Company | Lubrication oil compositions |
BRPI0815315A2 (pt) * | 2007-08-24 | 2017-05-09 | Du Pont | composição de oleo lubrificante |
WO2009059148A2 (en) * | 2007-11-01 | 2009-05-07 | E. I. Du Pont De Nemours And Company | Preparation of polytrimethylene ether glycol or copolymers thereof |
CN101842412A (zh) * | 2007-11-01 | 2010-09-22 | 纳幕尔杜邦公司 | 聚三亚甲基醚二醇的制备 |
US7919017B2 (en) * | 2007-11-12 | 2011-04-05 | E. I. Du Pont De Nemours And Company | Electrical insulation fluids for use in electrical apparatus |
WO2009064821A1 (en) | 2007-11-13 | 2009-05-22 | E. I. Du Pont De Nemours And Company | Isocyanate terminated polytrimethylene ether polyol and process for making same |
US20090197779A1 (en) * | 2008-01-31 | 2009-08-06 | Scott Christopher Jackson | Method for enhanced recovery of oil from oil reservoirs |
US20110052919A1 (en) * | 2008-04-22 | 2011-03-03 | E.I. Du Pont De Nemours And Company | Coating composition containing polytrimethylene ether diol |
WO2009155409A1 (en) * | 2008-06-18 | 2009-12-23 | E. I. Du Pont De Nemours And Company | Polyester and polytrimethylene ether diol based coating composition |
US7910644B2 (en) * | 2008-07-02 | 2011-03-22 | E.I. Du Pont De Nemours & Company | High film build coating composition containing polytrimethylene ether diol |
US8349407B2 (en) | 2008-07-02 | 2013-01-08 | E I Du Pont De Nemours And Company | High film build coating composition containing polytrimethylene ether diol |
IL200995A0 (en) * | 2008-10-01 | 2010-06-30 | Bayer Materialscience Ag | Polyether-based polyurethane formulations for the production of holographic media |
EP2352585B1 (en) | 2008-10-06 | 2020-06-17 | Union Carbide Corporation | Low metal loaded, alumina supported, catalyst compositions and amination process |
ES2433422T3 (es) | 2008-10-06 | 2013-12-11 | Union Carbide Chemicals & Plastics Technology Llc | Métodos para preparar triaminas N-aminofuncionales cíclicas |
EP2340113B1 (en) | 2008-10-06 | 2020-06-03 | Union Carbide Corporation | Low metal (nickel and rhenium) catalyst compositions including acidic mixed metal oxide as support |
CN102171179B (zh) * | 2008-10-06 | 2014-04-30 | 联合碳化化学品及塑料技术公司 | 亲核化合物的烷氧基转移 |
CN101412798B (zh) * | 2008-11-21 | 2011-08-10 | 优洁(亚洲)有限公司 | 软质聚氨酯低回弹泡沫及其制备方法 |
CN102264781A (zh) * | 2008-12-23 | 2011-11-30 | 纳幕尔杜邦公司 | 聚(三亚甲基醚)二醇的(甲基)丙烯酸酯及其用途 |
CN102264797A (zh) * | 2008-12-23 | 2011-11-30 | 纳幕尔杜邦公司 | 聚(三亚甲基醚)二醇的丙烯酸酯和甲基丙烯酸酯的制备方法 |
MX2011006734A (es) * | 2008-12-23 | 2011-07-13 | Du Pont | Esteres acrilicos y metacrilicos de glicol de eter de politrimetileno. |
US20110257330A1 (en) | 2008-12-30 | 2011-10-20 | E.I. Du Pont De Nemours And Company | Waterborne coating composition containing polytrimethylene ether diol |
US20100267994A1 (en) * | 2009-04-16 | 2010-10-21 | E. I. Du Pont De Nemours And Company | Processes for preparing polytrimethylene glycol using ion exchange resins |
IN2012DN00349A (ko) * | 2009-07-22 | 2015-08-21 | Du Pont | |
WO2011011279A2 (en) * | 2009-07-22 | 2011-01-27 | E. I. Du Pont De Nemours And Company | Methods for synthesizing polytrimethylene ether glycol and copolymers thereof |
US8771784B2 (en) * | 2009-07-30 | 2014-07-08 | Axalta Coating Systems Ip Co., Llc | Method for producing coating having desired gloss value |
FR2950823B1 (fr) * | 2009-10-06 | 2011-12-09 | Inst Francais Du Petrole | Reacteur a cocourant ascendant de gaz et de liquide faisant appel a un generateur de micro bulles |
US20110112331A1 (en) * | 2009-11-09 | 2011-05-12 | E.I. Du Pont De Nemours And Company | Method for phase separation of polytrimethylene ether glycol in salt solution |
EP2513627B1 (en) | 2009-12-18 | 2021-06-30 | Coatings Foreign IP Co. LLC | Method for coating measurement |
CN102666651B (zh) * | 2009-12-21 | 2014-09-10 | 纳幕尔杜邦公司 | 用于制备聚三亚甲基醚二醇及其共聚物的方法 |
EP2542612B1 (de) | 2010-03-02 | 2014-04-30 | Basf Se | Verfahren zur herstellung von polyetheralkoholen |
US9018263B2 (en) * | 2010-03-15 | 2015-04-28 | E I Du Pont De Nemours And Company | Antimicrobial compositions comprising trimethylene glycol oligomer and methods of using the compositions |
US8436081B2 (en) | 2010-08-31 | 2013-05-07 | U.S. Coatings IP Co. LLC. | High film build coating composition containing low molecular weight polytrimethylene ether glycol |
US8410205B2 (en) | 2010-08-31 | 2013-04-02 | E I Du Pont De Nemours And Company | Matting agent composition containing low molecular weight polytrimethylene ether glycol |
US8372905B2 (en) | 2010-08-31 | 2013-02-12 | E I Du Pont De Nemours And Company | Coating compositions containing low molecular weight polytrimethylene ether glycol |
EP2638098A1 (en) | 2010-11-10 | 2013-09-18 | Coatings Foreign IP Co. LLC | Radiation curable coating composition containing low molecular weight polytrimethylene ether glycol |
WO2012067691A1 (en) | 2010-11-19 | 2012-05-24 | E. I. Du Pont De Nemours And Company | Blends comprising branched poly(trimethylene ether) polyols |
US8247526B2 (en) | 2010-12-20 | 2012-08-21 | E I Du Pont De Nemours And Company | Process for the preparation of polyalkylene ether glycol |
CN103370125B (zh) * | 2010-12-21 | 2015-11-25 | 花王株式会社 | 塔型接触装置和其运转方法 |
CN102620400B (zh) | 2011-01-30 | 2013-12-11 | 昌硕科技(上海)有限公司 | 空调装置 |
EP2702089B1 (en) | 2011-04-26 | 2017-04-05 | E. I. du Pont de Nemours and Company | Processes for preparing polytrimethylene ether glycol |
DE112012005181B4 (de) | 2011-12-12 | 2019-07-04 | Coatings Foreign Ip Co. Llc | Wasserbasierende Beschichtungszusammensetzung, die Polytrimethylenetherpolyol aus Bioressourcen enthält, Mehrschichtlackierung und Verfahren zum Bilden einer Mehrschichtlackierung |
WO2013126432A1 (en) | 2012-02-21 | 2013-08-29 | California Institute Of Technology | Axially-integrated epitaxially-grown tandem wire arrays |
WO2013152132A1 (en) | 2012-04-03 | 2013-10-10 | The California Institute Of Technology | Semiconductor structures for fuel generation |
US8759559B2 (en) | 2012-04-18 | 2014-06-24 | E I Du Pont De Nemours And Company | Processes for preparing polytrimethylene ether glycol esters |
US9553223B2 (en) | 2013-01-24 | 2017-01-24 | California Institute Of Technology | Method for alignment of microwires |
EP3077444B1 (en) | 2013-12-02 | 2018-04-25 | Dow Global Technologies LLC | Preparation of high molecular weight, branched, acyclic polyalkyleneamines and mixtures thereof |
EP3083637A4 (en) * | 2013-12-19 | 2017-05-31 | Archer Daniels Midland Co. | An improved glycol acylation process |
EP3663383B1 (en) | 2018-12-05 | 2021-01-20 | The Procter & Gamble Company | Liquid hand dishwashing cleaning composition |
WO2022076208A1 (en) * | 2020-10-06 | 2022-04-14 | Dow Global Technologies Llc | Method of making an amphiphilic oxetane oligomer |
JP6912681B1 (ja) * | 2021-02-01 | 2021-08-04 | 株式会社日本触媒 | 第2級アルコールアルコキシレートの製造方法 |
Family Cites Families (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2520733A (en) * | 1946-08-26 | 1950-08-29 | Shell Dev | Polymers of trimethylene glycol |
US2492955A (en) | 1946-08-31 | 1950-01-03 | Shell Dev | Polyoxyalkylene compounds |
US3027352A (en) | 1958-02-28 | 1962-03-27 | Celanese Corp | Copolymers |
US3023192A (en) | 1958-05-29 | 1962-02-27 | Du Pont | Segmented copolyetherester elastomers |
US3192184A (en) * | 1959-03-19 | 1965-06-29 | Du Pont | Prepolymerization process |
US3384623A (en) | 1964-01-11 | 1968-05-21 | Toyo Spinning Co Ltd | Production of polyurethane elastomers |
US3326985A (en) * | 1964-12-29 | 1967-06-20 | Shell Oil Co | Polytrimethylene glycol |
US3526484A (en) * | 1968-05-17 | 1970-09-01 | Du Pont | Polymer finishing apparatus |
US3651014A (en) | 1969-07-18 | 1972-03-21 | Du Pont | Segmented thermoplastic copolyester elastomers |
US3626484A (en) * | 1969-09-22 | 1971-12-07 | Acf Ind Inc | Brake rigging for railway freight cars |
US3763109A (en) | 1971-08-19 | 1973-10-02 | Du Pont | Segmented thermoplastic copolyesters |
DE2818240A1 (de) | 1978-04-26 | 1979-11-08 | Hoechst Ag | Thermoplastische formmassen auf basis von polyoxymethylenen |
DE3016113A1 (de) | 1980-04-25 | 1981-10-29 | Bayer Ag, 5090 Leverkusen | Verfahren zur aufarbeitung von polyetherpolyolen |
US4970296A (en) * | 1984-03-01 | 1990-11-13 | Massachusetts Institute Of Technology | Heterodimeric T lymphocyte receptor |
JP2608939B2 (ja) | 1988-10-26 | 1997-05-14 | 帝人株式会社 | ポリエーテルエステルブロック共重合体 |
US4970295A (en) | 1989-02-27 | 1990-11-13 | Arco Chemical Technology, Inc. | Preparation of oxetane polyether polyols using a bleaching earth catalyst |
US4937314A (en) | 1989-02-28 | 1990-06-26 | E. I. Du Pont De Nemours And Company | Copolyetherester elastomer with poly(1,3-propylene terephthalate) hard segment |
ATE164176T1 (de) * | 1990-11-27 | 1998-04-15 | Commw Scient Ind Res Org | A process for the production of polyalkylenoxide |
US5128185A (en) | 1991-08-29 | 1992-07-07 | E. I. Du Pont De Nemours And Company | Copolyetherester elastomer with poly(1,3-propylenebibenzoate) hard segment |
ES2166765T3 (es) | 1992-10-21 | 2002-05-01 | Du Pont | Polimerizacion de eteres ciclicos usando catalizadores de compuestos metalicos seleccionados. |
DE4236039A1 (de) | 1992-10-24 | 1994-04-28 | Basf Ag | Verfahren und Vorrichtung zur Herstellung von Polykondensaten |
EP0614877B1 (de) | 1993-03-12 | 1997-08-20 | Bayer Ag | Verfahren zur kontinuierlichen Herstellung von Arylcarbonaten |
DE69531072T2 (de) | 1994-10-28 | 2004-05-06 | E.I. Du Pont De Nemours And Co., Wilmington | Polymerisation von cyclischen Ethern und unter Anwendung der Katalysatoren ausgewählten Metallverbindungen |
US5674974A (en) | 1994-11-23 | 1997-10-07 | E. I. Du Pont De Nemours And Company | Continuous polymerization process for polyamides |
US5731453A (en) * | 1996-03-12 | 1998-03-24 | Ube Industries, Ltd. | Process for producing a diaryl carbonate |
US5677415A (en) * | 1996-03-28 | 1997-10-14 | E. I. Du Pont De Nemours And Company | Apparatus and process for a polycondensation reaction |
US5659089A (en) | 1996-05-22 | 1997-08-19 | Arco Chemical Technology, L.P. | Process for making poly(2-methyl-1,3-propanediol) |
US5814282A (en) * | 1997-01-15 | 1998-09-29 | Lohe; Hans | High surface intermeshing profile reactor |
DE19706901A1 (de) * | 1997-02-21 | 1998-08-27 | Bayer Ag | Verfahren zur Durchführung von Polykondensationsreaktionen |
AUPO761697A0 (en) | 1997-06-30 | 1997-07-24 | Cardiac Crc Nominees Pty Limited | Process for the purification of polyethers |
US6235948B1 (en) | 1998-08-18 | 2001-05-22 | E. I. Du Pont De Nemours And Company | Process for the purification of 1,3-propanediol |
WO2001044150A2 (en) * | 1999-12-17 | 2001-06-21 | E.I. Du Pont De Nemours And Company | Continuous process for the preparation of polytrimethylene ether glycol |
AU2581401A (en) * | 1999-12-17 | 2001-06-25 | E.I. Du Pont De Nemours And Company | Production of polytrimethylene ether glycol and copolymers thereof |
-
2000
- 2000-12-15 WO PCT/US2000/034203 patent/WO2001044150A2/en active IP Right Grant
- 2000-12-15 MX MXPA02005949A patent/MXPA02005949A/es active IP Right Grant
- 2000-12-15 AU AU22709/01A patent/AU2270901A/en not_active Abandoned
- 2000-12-15 JP JP2001545240A patent/JP4638646B2/ja not_active Expired - Lifetime
- 2000-12-15 AT AT00986476T patent/ATE340154T1/de not_active IP Right Cessation
- 2000-12-15 EP EP00986476A patent/EP1237835B1/en not_active Expired - Lifetime
- 2000-12-15 DE DE60030880T patent/DE60030880T2/de not_active Expired - Lifetime
- 2000-12-15 US US09/738,689 patent/US6720459B2/en not_active Expired - Lifetime
- 2000-12-15 CA CA2389800A patent/CA2389800C/en not_active Expired - Fee Related
- 2000-12-15 CN CNB00817315XA patent/CN1238317C/zh not_active Expired - Lifetime
- 2000-12-15 KR KR1020027007493A patent/KR100677808B1/ko active IP Right Grant
-
2004
- 2004-01-20 US US10/760,339 patent/US7074968B2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
US20020010374A1 (en) | 2002-01-24 |
CN1411431A (zh) | 2003-04-16 |
MXPA02005949A (es) | 2003-01-28 |
WO2001044150A2 (en) | 2001-06-21 |
AU2270901A (en) | 2001-06-25 |
US6720459B2 (en) | 2004-04-13 |
US20040152925A1 (en) | 2004-08-05 |
DE60030880T2 (de) | 2007-04-26 |
JP2003517082A (ja) | 2003-05-20 |
KR100677808B1 (ko) | 2007-02-05 |
JP4638646B2 (ja) | 2011-02-23 |
EP1237835A2 (en) | 2002-09-11 |
ATE340154T1 (de) | 2006-10-15 |
US7074968B2 (en) | 2006-07-11 |
EP1237835B1 (en) | 2006-09-20 |
CN1238317C (zh) | 2006-01-25 |
CA2389800A1 (en) | 2001-06-21 |
DE60030880D1 (de) | 2006-11-02 |
WO2001044150A3 (en) | 2002-01-03 |
CA2389800C (en) | 2011-12-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR100677808B1 (ko) | 폴리트리메틸렌 에테르 글리콜의 연속 제조 방법 | |
KR100677809B1 (ko) | 폴리트리메틸렌 에테르 글리콜 및 그의 공중합체의 제조방법 | |
KR100443389B1 (ko) | 폴리에스테르 예비중합체의 제조 방법 | |
KR20080038211A (ko) | 폴리에테르 알코올의 제조 방법 | |
US5364973A (en) | Productive process for making conventional and low-unsaturation polyether polyols | |
CN103224621B (zh) | 改进的醇解方法和装置 | |
EP2419471B1 (en) | Improved copolyether glycol manufacturing process | |
KR101874474B1 (ko) | 코폴리에테르 에스테르 폴리올 공정 | |
JP3849360B2 (ja) | ポリテトラメチレンエーテルグリコールの製造方法 | |
KR20120005034A (ko) | 이온 교환 수지를 사용하여 폴리트라이메틸렌 글리콜을 제조하는 방법 | |
KR20120017040A (ko) | 코폴리에테르 글리콜 제조 방법 | |
US20100267905A1 (en) | Copolyether glycol manufacturing process | |
US20140142272A1 (en) | Continuous preparation for polyester |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A201 | Request for examination | ||
E902 | Notification of reason for refusal | ||
E701 | Decision to grant or registration of patent right | ||
GRNT | Written decision to grant | ||
FPAY | Annual fee payment |
Payment date: 20121220 Year of fee payment: 7 |
|
FPAY | Annual fee payment |
Payment date: 20131219 Year of fee payment: 8 |
|
FPAY | Annual fee payment |
Payment date: 20141230 Year of fee payment: 9 |
|
FPAY | Annual fee payment |
Payment date: 20160104 Year of fee payment: 10 |
|
FPAY | Annual fee payment |
Payment date: 20170102 Year of fee payment: 11 |
|
FPAY | Annual fee payment |
Payment date: 20180103 Year of fee payment: 12 |
|
FPAY | Annual fee payment |
Payment date: 20190103 Year of fee payment: 13 |
|
FPAY | Annual fee payment |
Payment date: 20200103 Year of fee payment: 14 |