KR100697162B1 - 아디프산 또는 프탈산의 이성질체 노난올 디에스테르의혼합물 - Google Patents
아디프산 또는 프탈산의 이성질체 노난올 디에스테르의혼합물 Download PDFInfo
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- 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
- C08K5/11—Esters; Ether-esters of acyclic polycarboxylic acids
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C69/44—Adipic acid esters
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/80—Phthalic acid esters
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- 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
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- C08K5/05—Alcohols; Metal alcoholates
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- 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
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- C08K5/12—Esters; Ether-esters of cyclic polycarboxylic acids
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Abstract
Description
디이소노닐 아디페이트 | 실시예 1 | 비교 실시예 1 "엑손 제이플렉스 DINA" |
1H NMR 스펙트럼에서의 1.0 - 2.0 ppm (CH2 및 CH기) 및 0.5 - 1.0 ppm (CH3기)에서의 신호기의 강도 비율 | 1.75 | 1.14 |
가소화 PVC 배합물의 냉각 균열 온도 (℃) | -64 | -56 |
가소화 PVC 배합물의 비틀림 강도 (℃) | -55 | -49 |
70℃ 및 100% 상대 습도에서의 혼화성 시험 가소화 PVC 배합물의 중량 손실 (중량%) 1일 후 3일 후 7일 후 14일 후 28일 후 | 0.11 0.27 0.57 0.80 1.00 | 0.22 0.33 0.69 0.88 1.07 |
디이소노닐 프탈레이트 | 실시예 2 | 엑손 제이플렉스 DINP를 사용한 비교 실시예 2 | BASF 팔라티놀 DN을 사용한 비교 실시예 3 |
1H NMR 스펙트럼에서 1.1-3.0 ppm (CH2 및 CH기) 및 0.5-1.1 ppm (CH3기)에서의 신호기의 강도 비율 | 1.66 | 0.90 | 0.53 |
1H NMR 스펙트럼에서 0.8-1.1 ppm에서의 신호기 및 0.7-0.8 ppm의 신호기(삼중선)의 강도 비율 | 25.3 | - | - |
가소화 PVC 배합물의 균열 균열 온도 (℃) | -42 | -31 | -23 |
가소화 PVC 배합물의 200℃에서의 HCl 잔류 안정성(분) | 18 | 13.8 | 14.4 |
Claims (10)
- CDCl3에서 관찰한 1H NMR 스펙트럼에서 TMS에 대해 0.5 내지 1.0 ppm 범위의 화학 이동에서의 공명 신호하의 면적에 대한 TMS에 대해 1.0 내지 2.0 ppm 범위의 화학 이동에서의 공명 신호하의 면적의 비율이 1.70 내지 2.00인 아디프산의 디에스테르의 혼합물, 및CDCl3에서 관찰한 1H NMR 스펙트럼에서 TMS에 대해 0.5 내지 1.1 ppm 범위의 화학 이동에서의 공명 신호하의 면적에 대한 TMS에 대해 1.1 내지 3.0 ppm 범위의 화학 이동에서의 공명 신호하의 면적의 비율이 1.50 내지 2.00인 프탈산의 디에스테르의 혼합물로 이루어지는 군으로부터 선택되는 디카르복실산의 이성질체 노난올 디에스테르의 혼합물.
- 제1항에 있어서, 부텐 함유 탄화수소 혼합물을 니켈 옥사이드를 포함하는 불균일 촉매와 접촉시켜서 얻은 이성질체 옥텐 혼합물을 히드로포르밀화 및 수소화하여 얻은 이성질체 노난올 혼합물을, 아디프산 및 프탈산으로부터 선택되는 디카르복실산 또는 그 유도체로 에스테르화함으로써 얻어진 혼합물.
- 제2항에 있어서, 탄화수소 혼합물이 총 부텐 함량에 기초하여 5 중량% 이하의 이소부텐을 포함하는 혼합물.
- 제3항에 있어서, 탄화수소 혼합물이 총 부텐 함량에 기초하여 3 중량% 이하의 이소부텐을 포함하는 혼합물.
- 제2항 내지 제4항 중 어느 한 항에 있어서, 촉매가 중요 활성 성분으로서 10 내지 70 중량%의 니켈 옥사이드, 5 내지 30 중량%의 티타늄 디옥사이드 및(또는) 지르코늄 디옥사이드, 0 내지 20 중량%의 알루미늄 옥사이드, 및 그 나머지 실리콘 디옥사이드를 포함하는 혼합물.
- 제2항 내지 제4항 중 어느 한 항에 있어서, 히드로포르밀화가 코발트 촉매 존재하에서 일어나는 것인 혼합물.
- 제1항 내지 제4항 중 어느 한 항의 혼합물을 포함하는 성형 조성물용 가소제.
- 아디프산에 의한 에스테르화에 의해 CDCl3에서 관찰한 1H NMR 스펙트럼에서 TMS에 대해 0.5 내지 1.0 ppm 범위의 화학 이동에서의 공명 신호하의 면적에 대한, TMS에 대해 1.0 내지 2.0 ppm 범위의 화학 이동에서의 공명 신호하의 면적의 비율이 1.70 내지 2.00인 아디프산의 디에스테르의 혼합물을 생성하고(생성하거나),프탈산에 의한 에스테르화에 의해 CDCl3에서 관찰한 1H NMR 스펙트럼에서 TMS에 대해 0.5 내지 1.1 ppm 범위의 화학 이동에서의 공명 신호하의 면적에 대한, TMS에 대해 1.1 내지 3.0 ppm 범위의 화학 이동에서의 공명 신호하의 면적의 비율이 1.50 내지 2.00인 프탈산의 디에스테르의 혼합물을 생성하는 이성질체 노난올의 혼합물.
- 총 부텐 함량에 기초하여 5 중량% 이하의 이소부텐을 포함하는 부텐 함유 탄화수소 혼합물을 니켈 옥사이드를 포함하는 불균일 촉매와 접촉시켜서 얻은 이성질체 옥텐 혼합물을 코발트 촉매 존재하에서 히드로포르밀화하고, 히드로포르밀화 생성물을 수소화함으로써 얻어진 이성질체 노난올의 혼합물.
- 제9항에 있어서, 불균일 촉매가 중요 활성 성분으로서 10 내지 70 중량%의 니켈 옥사이드, 5 내지 30 중량%의 티타늄 디옥사이드 및(또는) 지르코늄 디옥사이드, 0 내지 20 중량%의 알루미늄 옥사이드, 및 그 나머지의 실리콘 디옥사이드를 포함하는 이성질체 노난올의 혼합물.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19918051.2 | 1999-04-21 | ||
DE1999118051 DE19918051A1 (de) | 1999-04-21 | 1999-04-21 | Gemische von Diestern der Phthalsäure mit isomeren Nonanolen |
DE19924339.5 | 1999-05-27 | ||
DE1999124339 DE19924339A1 (de) | 1999-05-27 | 1999-05-27 | Gemische von Diestern der Adipinsäure mit isomeren Nonanolen |
Publications (2)
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KR20020010899A KR20020010899A (ko) | 2002-02-06 |
KR100697162B1 true KR100697162B1 (ko) | 2007-03-21 |
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KR1020017013328A KR100697162B1 (ko) | 1999-04-21 | 1999-11-26 | 아디프산 또는 프탈산의 이성질체 노난올 디에스테르의혼합물 |
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US (1) | US6437170B1 (ko) |
EP (1) | EP1171413B1 (ko) |
JP (1) | JP5237513B2 (ko) |
KR (1) | KR100697162B1 (ko) |
CN (1) | CN1160305C (ko) |
AT (1) | ATE261929T1 (ko) |
AU (1) | AU778207B2 (ko) |
BR (1) | BR9917230A (ko) |
CA (1) | CA2367358C (ko) |
DE (1) | DE59908919D1 (ko) |
DK (1) | DK1171413T3 (ko) |
ES (1) | ES2217891T3 (ko) |
MY (1) | MY129459A (ko) |
TW (1) | TWI274052B (ko) |
WO (1) | WO2000063151A1 (ko) |
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KR102496349B1 (ko) * | 2017-11-29 | 2023-02-03 | 한화솔루션 주식회사 | 프탈레이트 화합물의 수소화 방법 |
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- 1999-11-26 CA CA002367358A patent/CA2367358C/en not_active Expired - Lifetime
- 1999-11-26 KR KR1020017013328A patent/KR100697162B1/ko active IP Right Grant
- 1999-11-26 CN CNB998166502A patent/CN1160305C/zh not_active Expired - Lifetime
- 1999-11-26 DK DK99973824T patent/DK1171413T3/da active
- 1999-11-26 US US09/449,395 patent/US6437170B1/en not_active Expired - Lifetime
- 1999-11-26 AU AU13872/00A patent/AU778207B2/en not_active Expired
- 1999-11-26 BR BR9917230-5A patent/BR9917230A/pt not_active Application Discontinuation
- 1999-11-26 WO PCT/EP1999/009208 patent/WO2000063151A1/de active IP Right Grant
- 1999-11-26 EP EP99973824A patent/EP1171413B1/de not_active Revoked
- 1999-11-26 JP JP2000612248A patent/JP5237513B2/ja not_active Expired - Lifetime
- 1999-11-26 ES ES99973824T patent/ES2217891T3/es not_active Expired - Lifetime
- 1999-11-26 AT AT99973824T patent/ATE261929T1/de active
- 1999-11-26 DE DE59908919T patent/DE59908919D1/de not_active Expired - Lifetime
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2000
- 2000-02-01 TW TW089101732A patent/TWI274052B/zh not_active IP Right Cessation
- 2000-02-03 MY MYPI20000391A patent/MY129459A/en unknown
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Also Published As
Publication number | Publication date |
---|---|
EP1171413A1 (de) | 2002-01-16 |
CN1160305C (zh) | 2004-08-04 |
WO2000063151A1 (de) | 2000-10-26 |
CA2367358A1 (en) | 2000-10-26 |
DE59908919D1 (de) | 2004-04-22 |
DK1171413T3 (da) | 2004-07-19 |
ES2217891T3 (es) | 2004-11-01 |
US6437170B1 (en) | 2002-08-20 |
KR20020010899A (ko) | 2002-02-06 |
AU778207B2 (en) | 2004-11-25 |
ATE261929T1 (de) | 2004-04-15 |
BR9917230A (pt) | 2002-01-08 |
JP5237513B2 (ja) | 2013-07-17 |
AU1387200A (en) | 2000-11-02 |
CA2367358C (en) | 2010-02-02 |
EP1171413B1 (de) | 2004-03-17 |
JP2002542217A (ja) | 2002-12-10 |
TWI274052B (en) | 2007-02-21 |
CN1350515A (zh) | 2002-05-22 |
MY129459A (en) | 2007-04-30 |
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