KR20200088430A - 안정화 효과를 갖는 화합물, 상기 화합물의 제조 방법, 상기 안정화 화합물을 함유하는 조성물, 유기 성분의 안정화 방법 및 안정화 화합물의 용도 - Google Patents
안정화 효과를 갖는 화합물, 상기 화합물의 제조 방법, 상기 안정화 화합물을 함유하는 조성물, 유기 성분의 안정화 방법 및 안정화 화합물의 용도 Download PDFInfo
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- KR20200088430A KR20200088430A KR1020207017551A KR20207017551A KR20200088430A KR 20200088430 A KR20200088430 A KR 20200088430A KR 1020207017551 A KR1020207017551 A KR 1020207017551A KR 20207017551 A KR20207017551 A KR 20207017551A KR 20200088430 A KR20200088430 A KR 20200088430A
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- Prior art keywords
- tert
- compound
- butyl
- agents
- bis
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- WMXBGWKUWMQWAL-UHFFFAOYSA-H trizinc 1,3,5-triazine-2,4,6-triamine diphosphate Chemical compound N1=C(N)N=C(N)N=C1N.P(=O)([O-])([O-])[O-].[Zn+2].P(=O)([O-])([O-])[O-].[Zn+2].[Zn+2] WMXBGWKUWMQWAL-UHFFFAOYSA-H 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
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- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
- 239000002446 δ-tocopherol Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
- C07D251/32—Cyanuric acid; Isocyanuric acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/18—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by addition of thiols to unsaturated compounds
-
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/12—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/13—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated and containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/16—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
- C07D251/34—Cyanuric or isocyanuric esters
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/372—Sulfides, e.g. R-(S)x-R'
- C08K5/3725—Sulfides, e.g. R-(S)x-R' containing nitrogen
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- C08K5/00—Use of organic ingredients
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- C08K5/00—Use of organic ingredients
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- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/12—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing sulfur and oxygen
- C09K15/14—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing sulfur and oxygen containing a phenol or quinone moiety
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- Polymers & Plastics (AREA)
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- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
본 발명은 안정화 효과를 가지며 특히 유기 물질의 산화적 열적 및 / 또는 광화학선 분해 또는 손상과 관련하여 안정화를 제공하는 새로운 유형의 화합물에 관한 것이다. 화합물은 특정 화학식 I로 표시된다. 본 발명은 또한 이러한 화합물의 제조 방법, 상기 화합물을 함유하는 조성물, 안정화 화합물에 의한 유기 화합물의 안정화 방법, 및 안정화 화합물의 유기 물질의 안정화의 용도에 관한 것이다.
Description
본 발명은 안정화 효과, 특히 유기 물질의 산화적 열적 및 / 또는 광화학선 분해 또는 손상과 관련하여 안정화를 갖는 신규 한 화합물에 관한 것이다. 화합물은 하기에 나타낸 화학식 I로 표시된다. 본 발명은 추가로 이러한 화합물의 제조 방법, 상기 화합물을 함유하는 조성물, 안정화 화합물의 도움으로 유기 성분을 안정화시키는 방법, 및 유기 물질의 안정화를위한 상기 안정화 화합물의 용도에 관한 것이다.
플라스틱과 같은 유기 물질은 에이징 과정을 거쳐 궁극적으로 기계적 특성 값과 같은 원하는 특성을 잃게된다. 자동 산화라고 불리는이 과정은 라디칼 사슬 가위로부터 출발하여 기계 화학적 공정 또는 산소 존재 하의 UV 방사선으로 인해 분자량 또는 새로운 화학기의 형성과 같은 중합체 사슬에 변화를 일으킨다. 그러므로 안정화제는 이러한 에이징을 방지하거나 적어도 지연시키기 위해 사용된다. 안정화제의 중요한 대표물은 자동산화에서 형성된 라디칼을 방해하여 분해 과정을 방해하는 산화 방지제를 포함한다. 일반적으로 산소를 함유한 자유 라디칼 또는 C 라디칼과 직접 반응 할 수있는 1 차 산화 방지제와 중간에 형성된 하이드 로 퍼옥사이드와 반응하는 2 차 산화 방지제를 구분한다 (C. Krφhnke et al. Antioxidants in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH Verlag, Weinheim 2015 참조). 일차 산화 방지제의 전형적인 대표는 예를 들어 페놀계 산화 방지제, 아민뿐만 아니라 락톤을 포함한다. 이차 산화 방지제의 부류는 포스파이트 및 포스포나이트와 같은 인 화합물 뿐만 아니라 황화물 및 이황화물과 같은 티오 화합물도 포함한다. 일차 및 이차 산화 방지제의 상호 사용은 여기서 시너지 효과를 초래할 수 있다. 페놀계 산화 방지제와 포스파이트 / 포스포니트의 조합뿐만 아니라 페놀계 산화 방지제와 티오 화합물의 조합. (예를 들어, I. Vulic et al. Pol. Degr. Stab. 2002, 78, 27-34 참조). 따라서, 상승 효과의 배경에 대하여, 하나의 분자에서 두 가지 기능, 즉 일차 및 이차 산화방지 효과의 기능을 모두 갖는 안정 화제를 개발하는 것이 또한 바람직하다.
한 분자 내에 입체 장애 페놀 그룹 및 티오 그룹 둘 다를 함유하는 황, 즉 안정화제를 함유하는 산화 방지제는 일반적으로 공지되어 있으며 부분적으로 시판되고있다. 여기서 상용 제품은 예를들어 다음과 같은 구조를 갖는다 (상품명, 예 : Songnox 4150, Irganox 1081, Irganox 1035, Irganox 1520, Irganox 565, Hostanox OSP 1) :
이들 안정화제의 합성 및 사용은 다수의 특허에 기술되어있다; 예로서, DE 23641126, DD 251128, EP 275832, EP 428973, US 3245992 및 US 3257354가 언급된다.
또한 지방족 티오 그룹은 방향족 티오 그룹 (예를 들어, US 2,981,717)보다 더 작은 변색 경향을 갖는 것으로 알려져 있으며, 이는 일반적으로 유기 물질의 장기 안정성에 바람직한 특성이다.
페놀성 및 티오기를 모두 포함하는 추가의 안정화제는 특허 명세서 US 4,727,103, US 4,633,008 및 US 4,694,102에 이소시아누레이트를 함유하는 분자 형태로 기술되어 있다. 이들 특허에 언급된 화학 구조는 본 발명 및 다른 공정에 따른 구조와 다르게 제조된다.
고농도의 입체 장애 페놀 및 고농도의 지방족 티오기를 동시에 갖는 시판 제품이 없다는 것은 황을 함유 한 상기 언급 된 상업용 산화 방지제의 관찰에 주목되고 있다.
따라서, 본 발명의 목적은 유기 물질, 특히 플라스틱에 대해 우수한 안정화 효과를 갖는 황 및 신규 화합물을 함유하는 산화 방지제를 제조하는 새로운 방법을 제공하는 것이다.
이 목적은 청구항 1에 따른 화학식 I에 따른 신규 화합물에 의해 달성된다. 상응하는 화합물의 제조는 청구항 7에 제공된다. 본 발명의 주제는 추가로 안정화 될 유기 성분 및 청구항 11에 따른 본 발명에 따른 화합물 중의 하나를 함유하는 조성물이다. 본 발명은 추가로 청구항 16에 따른 안정화 유기 성분을 안정화시키는 방법 및 청구항 17에 따른 본 발명에 따른 안정화 화합물의 용도에 관한 것이다.각각의 종속 항은 유리한 실시 예에 관한 것이다.
따라서 본 발명은 화학식 I에 따른 화합물에 관한 것이다
<화학식 I>
변수 A, B, D, R, b, x, y, z는 각각 서로 독립적으로 다음과 같은 정의를 갖는다:
A: 방향족, 불포화 또는 포화 잔기;
B: O 또는 NH;
D: 1 내지 12 개의 탄소 원자를 갖는 선형 또는 분지형 지방족 잔기;
R: 하나 이상의 입체 장애 기(group) 및 하나 이상의 히드록실기를 갖는 잔기;
b: 0 또는 1;
x: 0 내지 12;
y: 1 내지 4; 및
z: 1 내지 6.
복잡한 안정화제 구조에 대한 간단한 접근성을 허용하고 높은 효율을 갖는, 예를 들면 중합체에서, 새로운 안정 화제 및 안정 화제를 제조하는 새로운 방법이 제안되어 있다. 동시에 많은 수의 입체 장애 페놀기를 갖는 본 발명에 따른 방법으로 인한 높은 비율의 지방족 황 기(group)는 특히 특별한 장기적 안정화와 함께 새로운 화합물의 낮은 변색 경향을 나타낸다.
놀랍게도, 상기 화합물은 높은 안정화 가능성, 특히 열적 및 / 또는 광화학선(actinic) 분해에 대한 유기 물질의 안정화를 갖는 것으로 밝혀졌다.
바람직한 실시예는 변수 A가 각각의 z가 시아누르산 잔기, 여기서 z는 제 1 항에 제공된 의미를 가지며; 트리아진 잔기; 5 내지 36 개의 탄소 원자를 갖는 시클릭 지방족 탄화수소 잔기, 특히 시클로 헥실; 방향족 탄화수소 잔기, 특히 페닐; 및 2 내지 36 개의 탄소 원자를 갖는 선형 또는 분지형 지방족 탄화수소 잔기를 포함하는 군으로부터 선택되는 것을 제공한다.
여기서 변수R이 하나 이상의 입체 장애 히드록시페닐 잔기를 갖는기를 나타내고 특히 다음의 의미를 갖는 것이 더욱 유리하다.
E는 각각의 경우에 동일하거나 상이하고, 1 내지 18 개의 탄소 원자를 갖는 선형 지방족, 분지형 지방족 또는 시클로 지방족 알킬 잔기 또는 6 내지 36 개의 탄소 원자를 갖는 방향족 잔기 또는 수소, 특히 tert-부틸기 또는 메틸기를 나타낸다;
a는 1 또는 0; 및
c는 0, 1, 2, 3 또는 4.
두 잔기 E는 동일한 잔기 인 것이 바람직하다. 그러나, 잔기 E가 상이 할 수 있으며; 예를 들어 하나의 잔기 E는 수소 일 수 있고 다른 잔기 E는 메틸기 또는 t- 부틸기를 나타낼 수있다.
변수 x, y 및 z는 특히 서로 독립적으로 하기 의미를 갖는다:
X: 0 또는 1;
Y: 1 또는 2; 및
z: 1, 2, 3 또는 4.
화학식 I의 본 발명에 따른 화합물은 바람직하게는하기 화합물을 포함하는 군에서 선택된다 :
상기 z는 다음 의미를 갖고;
변수 B, D, R, b, x, y 및 z는 청구항 1과 같이 정의된다.
변수 D는 특히 -CH2- 또는 1,2,3- 프로피닐 잔기를 포함하는 군에서 선택된다.
본 발명의 특히 바람직한 구체 예는 본 발명에 따른 화합물이 하기 화합물의 군으로부터 선택되는 것을 제공한다:
여기서 잔기 Y는 서로 독립적으로 각각의 경우에 다음의 의미를 갖는다:
또는
상기 잔기에서, tBu 잔기는 또한 메틸 기 및 / 또는 수소로 전체적으로 또는 부분적으로 치환 될 수있다.
또한, 본 발명은 상기 정의 된 화학식 I에 따른 화합물의 제조 방법에 관한 것으로, 화학식 II에 따른 화합물이
<화학식 II>
화학식 IIIa 또는 IIIb 중 하나에 따른 티올과 반응하고, 및
<화학식 IIIa> <화학식 IIIb>
화학식 IIIa의 티올이 사용 된 경우, 이어서, 화학식 II 및 IIIa의 화합물의 반응에 의해 획득된 반응 생성물이 화학식 IV의 화합물과 반응한다
<화학식 IV>
여기서X는 이탈 기; 및
변수 A, B, D, R, b, x, y 및 z의 의미는 제 1 항에 나타낸 화학식 IIa, IIb 및 III의 화합물에서 정의된 바와 같다.
반복을 피하기 위해 앞서 명명 된 화학식 II, IIIa 및 IIIb에서 변수 A, B, D, R, b, x, y 및 z의 특정 변형에 대한 상기 설명을 참조한다. 본 발명에 따른 화합물 I에 대한 모든 바람직한 실시예는 화학식 II, IIIa, IIIb 및 IV에 동일하게 적용된다.
상기 언급 된 이탈 기는 여기에서 특히 알콜레이트, 할라이드, 트리플루오로메탄 설포네이트, 토실레이트, 메실레이트, 플루오로설포네이트 또는 노나플레이트이다.
따라서 본 발명에 따른 화합물의 제조는 티올-엔 반응 또는 커플링에 의해 수행된다.
티올과 반응성 C-C 이중 결합의 반응이 여기서 일어난다.
티올-엔 커플링은 코팅의 합성, 필름의 제조 및 중합체의 개질에 사용되는 반응이다 (예를 들어 CE Hoyle, CN Bowman, Angew. Chem. Int. Ed. 2010, 49, 1540-1573; AB Lowe, Polym. Chem. 2010, 1, 17-36 참조). 본 발명에 따른 안정화제에서 전구체로서 사용되는 트리알릴 시아누레이트의 사용은 Z. ltintas et al. Chinese Journal of Polymer Science 2015, 6, 850-856에 의해 티올-엔 커플 링을 위한 출발 생성물로서 기재되어 있다. 이는 열가소성 폴리 우레탄에서 티오에테르-작용기화된 사슬 연장 제(thioether-functionalized chain extender)로서 작용하고; 안정화제 또는 안정화제를 위한 중간체로서의 용도는 여기에 기술되지 않았거나 그로부터 유도될 수 없다. 본 발명에 따른 안정 화제에서 전구체로서 특히 사용되는 디알릴 프탈레이트의 사용은 (방향족) 아민-유도된 황변에 대한 억제제로서 Herweh et al.(US 4,035,337)에 의해 티올-엔 커플링을 위한 출발 생성물로서 기재되어 있다. 입체 장애 페놀과의 분자 조합 및 사용은 그 안에 기재되어 있지 않거나 그로부터 유도 될 수 없다. 티올-엔 커플링을 위한 출발 생성물로서, 특히 본 발명에 따른 안정화제에서 전구체로서 사용되는 스티렌의 사용은 특히 Dazzi (US 2,642,373)에 의한 살 진균제 또는 Gluesenkamp (US 2,617,778 A)에 의한 비닐 클로라이드 중합체를 위한 가소제로서 기술되고, 특히 Limnios et. al. Adv. Synth. Catal. 2017, 359, 323- 328에 의해 가능한 펩티드 및 글루코시드 변형에서 유기 분해 티올-올레핀 첨가에 대한 광 개시된 대안으로서 기술된다. 안정화제 또는 산화 방지제를 위한 중간체로서의 용도는 또한 그 안에 기재되어 있지 않거나 그로부터 유도될 수 없다.
티올-엔 반응은 H. Li et al. Polymer Composites 2015 및W. Wu J. Macromol. Sci. B 2014, 53, 1244-1257에서 안정화제 / 안정화와 관련하여 언급된다. 본 발명의 목적에 또한 적용되는 반응 원리와 관련하여 이들 문헌을 참조한다. 첫 번째 경우, 실란의 합성은 페놀계 안정화제 기능을 갖는 아크릴레이트에 마이클 (Michael) 첨가를 통해 일어난다. 두 번째 경우에, 폴리히드록시화된 폴리부타디엔의 반응이 먼저 수행되고, 이어서 디이소시아네이트 및 입체 장애 페놀과의 반응이 수행된다. 설명된 두 반응은 본 발명에 따른 안정 화제와 상이한 화학 생성물을 초래한다.
화학식 II에 따른 화합물과 화학식 IIIa 또는 IIIb 중 하나에 따른 티올의 전환은 바람직하게는 화학식 II 에 따른 화합물의 불포화 작용과 관련하여 과량의 티올로 수행된다.
본 발명은 추가로 안정화될 하나 이상의 유기 성분 및 상기 기재된 화학식 I에 따른 본 발명에 따른 하나 이상의 화합물을 포함하거나 이로 이루어진 조성물에 관한 것이다.
열가소성 수지, 엘라스토머 및 듀로머 플라스틱 용 안정화제는 특히 사출 성형 부품, 포일 또는 필름, 코팅 또는 래커(lacquer), 폼, 섬유 및 케이블, 튜브, 프로파일, 중공 체, 리본, 막, 예를 들어 지오멤브레인(geomembrane)의 형태로 형성될 수 있거나, 또는 예를 들어 압출, 사출 성형, 블로우 성형, 캘린더링, 프레싱 공정, 스피닝 공정, 로토몰딩 또는 스프레딩 및 코팅 공정을 통해 제조되는 접착제 형태로 형성될 수 있다. 본 발명에 따른 조성물은 예를 들어 전기 및 전자 산업, 건설 산업, 운송 산업 (자동차, 비행기, 선박, 철도), 의료 응용 분야, 가정 및 전기 제품, 자동차 부품, 소비재, 포장, 가구 또는 섬유에 사용된다. 추가 사용 영역에는 래커(lacquer), 페인트 및 코팅은 물론 헤비 듀티 윤활유와 같은 오일 및 지방이 포함된다.
본 조성물의 유리한 실시 양태는 안정화 될 성분이 플라스틱, 오일, 윤활제 및 지방을 포함하는 군에서 선택되는 것을 제공한다.
본 발명에 따른 조성물에 포함될 수있는 적합한 플라스틱 또는 중합체는 여기서 특히
a)
폴리에틸렌 (LDPE, LLDPE, VLDPE. ULDPE, MDE, HDPE 및 UHMWPE), 메탈로센(metallocene) PE (m-PE), 폴리 프로필렌(polypropylene), 폴리이소부틸렌, 폴리-4-메틸-펜텐-1, 폴리 부타디엔, 폴리이소프렌, 폴리시클로옥텐, 폴리알킬렌-일산화탄소 공중합체와 같은 올레핀 또는 디올레핀의 중합체, 및 폴리 프로필렌-폴리에틸렌 (EP), EPM 또는 EPDM, 에틸렌-비닐 아세테이트 (EVA), 에틸렌 부틸 아크릴레이트, 에틸렌-아크릴산 및 이들의 염 (이오노머)과 같은 에틸렌-아크릴 에스테르와 같은 통계 또는 블록 구조 형태의 공중 합체, 및 에틸렌 아크릴산 글리시딜 아크릴 레이트와 같은 터폴리머(terpolymer), 폴리 프로필렌 g- 말레 산 무수물, 폴리 프로필렌 g- 아크릴산 및 폴리에틸렌 g- 아크릴산과 같은 그라프트 중합체,
b) 폴리스티렌, 폴리메틸스티렌, 폴리비닐나프탈렌, 스티렌 부타디엔 (SB), 스티렌 부타디엔 스티렌 (SBS), 스티렌 에틸렌 부틸렌 스티렌 (SEBS), 스티렌 에틸렌 프로필렌 스티렌, 스티렌 이소프렌, 스티렌 이소프렌 스티렌 (SIS), 아크릴로 니트릴 부타디엔 스티렌 (ABS), 아크릴로니트릴 스티렌 아크릴레이트 (ASA), 메타크릴레이트 부타디엔 스티렌 (MBS), 메타크릴 레이트 아크릴로니트릴 부타디엔 스티렌 (MABS), 스티렌 에틸렌, 부타디엔의 스티렌, SBS 또는 SEBS의 말레 산 무수물과 같은 해당 그래프트 공중 합체를 포함하는 스티렌 말레산 무수물 폴리머,
c) 폴리 염화 비닐 (PVC), 폴리 클로로프렌 및 폴리 염화 비닐 리덴 (PVDC)과 같은 할로겐화물을 함유하는 중합체, 염화 비닐과 염화 비닐 리덴 또는 염화 비닐과 비닐 아세테이트의 공중 합체, 염화 폴리에틸렌, 폴리 비닐 리덴 플루오라이드,
d) 폴리아크릴레이트와 같은 불포화 에스테르의 중합체 및 폴리 메틸 메타 크릴레이트 (PMMA), 폴리부틸 아크릴레이트, 폴리라우릴 아크릴 레이트, 폴리 스테아릴 아크릴 레이트, 폴리 아크릴로 니트릴, 폴리 아크릴 아미드와 같은 폴리 메타 크릴 레이트, 폴리 아크릴로 니트릴-폴리 알킬 아크릴 레이트와 같은 공중 합체,
e) 불포화 알콜 및 폴리 비닐 알콜, 폴리 비닐 아세테이트, 폴리 비닐 부티 랄과 같은 유도체의 중합체,
f) 폴리 옥시 메틸렌 (POM)과 같은 폴리 아세테이트 또는 예를 들어 부탄알과의 공중합체,
g) 폴리 페닐렌 옥사이드 및 폴리스티렌 또는 폴리 아미드와의 블렌드,
h) 폴리에틸렌 글리콜, 폴리 프로필렌 글리콜, 폴리에틸렌 옥사이드, 폴리 프로필렌 옥사이드와 같은 사이클릭 에테르의 중합체,
i) 히드록시 말단 폴리 에테르 또는 폴리 에스테르 및 방향족 또는 지방족 이소시아네이트의 폴리 우레탄, 특히 선형 폴리 우레탄, 폴리 우레아,
j) 폴리 아미드 -6, 6.6, 6.10, 4.6, 4.10, 6.12, 12.12, 폴리 아미드 11, 폴리 아미드 12 및 (부분) 방향족 폴리 아미드, 예컨대 폴리 프탈 아미드, 예를 들어 테레프탈산 및 / 또는 이소 프탈산 및 지방족 디아민 또는 지방족 디카르복실산, 예컨대 아디프 산 또는 세바 스산 및 방향족 디아민, 예컨대 1,4- 또는 1,3-디아미노 벤졸로부터 제조되고,
k) 폴리이 미드, 폴리아미드 이미드, 폴리에테르 이미드, 폴리 에스테르 이미 드, 폴리 (에테르) 케톤, 폴리 설폰, 폴리 에테르 설폰, 폴리 아릴 설폰, 폴리 페닐렌 설파이드, 폴리벤지미다졸, 폴리히단토인,
l) 지방족 또는 방향족 디카 르 복실 산 및 디올 또는 히드 록시 카르 복실 산, 예컨데 폴리에틸렌 테레 프탈레이트 (PET), 폴리 부틸 렌 테레 프탈레이트 (PBT), 폴리 프로필렌 테레 프탈레이트, 폴리-1,4-디메틸올 시클로헥산 테레프탈레이트, 폴리히드록시 벤조에이트, 폴리히드록시 나프탈레이트, 폴리 락트산, 의 폴리 에스테르,
m) 폴리 카보네이트, 폴리 에스테르 카보네이트 및 PC / ABS, PC / PBT, PC / PET / PBT와 같은 블렌드,
n) 셀룰로오스 니트 레이트, 셀룰로오스 아세테이트, 셀룰로오스 프로 피오 네이트, 셀룰로오스 부티레이트와 같은 셀룰로오스 유도체,
o) 비 열가소성 플라스틱 또는 듀로 플라스틱
상기 언급 된 중합체가 공중합 체인 경우, 이들은 통계적 (무작위) 블록 구조 또는 테이퍼 구조 또는 입체 블록 공중 합체의 형태로 존재할 수있다.
이들이 입체 규칙적 중합체 인 경우; 그것들은 이소택틱 (isotactic), 정위적 (stereotactic)의 형태로 존재할 수 있지만, 또한 어택틱(atactic) 형태로 존재할 수있다.
중합체는 또한 가교 된 형태로 존재할 수있다. 여기서 가교는 예를 들어 라디칼 형성 제의 첨가에 의해 또는 처리 동안 또는 후속 단계에서 전자선, 베타선 또는 감마선과 같은 방사선에 의해 발생한다.
상기 중합체는 여기서 새로운 제품으로 존재할뿐만 아니라 재활용 된 제품의 형태로 존재할 수있다. 예를 들어 생산 폐기물 또는 재활용품 수거 (소비자 재활용 제품).
본 발명의 화합물은 또한 고무 및 엘라스토머의 안정화에 사용될 수있다. 여기서는 천연 고무 (NR) 또는 합성 고무 재료의 경우 일 수 있다.
화학식 I에 따른 화합물의 함유 된 양과 관련하여, 조성물이 95.00 내지 99.99 중량 %, 바람직하게는 97.00 내지 99.95 중량 %, 특히 바람직하게는 98.00 내지 99.90 중량 %의 하나 이상의 안정화될 성분을 포함하거나 이로 구성되고, 0.01 내지 5.00 중량 %, 바람직하게는 0.05 내지 3.00 중량 %, 특히 바람직하게는 0.10 내지 2.00 중량 %의 화학식 I에 따라 본 발명에 따른 하나 이상의 화합물을 포함하거나 이로 구성되는 경우, 바람직하다.
본 발명에 따른 조성물, 예를 들어 플라스틱에 기초하여, 하나 이상의 첨가제를 추가로 포함 할 수있다. 이 하나 이상의 첨가제는 특히 UV 흡수제, 광 안정 화제, 안정 화제, 산화 방지제, 히드록실아민, 벤조푸란, 금속 불활성화제, 충전제 불활성화제, 오존분해방지제(antiozonant), 핵형성제, 충격 강도 개선제, 가소제, 윤활제, 레올로지 개질제, 요 변제(thixotropic agent), 사슬 연장 제, 가공 보조제, 탈형 보조제, 난연제, 안료, 염료, 형광 증백제(optical brightener), 항균제, 대전 방지제, 슬립제, 블로킹방지제(antiblocking agent), 커플링제, 가교제, 가교방지제, 친수화제, 소수성 화제, 결합제, 분산제, 분해 첨가제, 소포 보조제, 냄새 트랩(odor traps), 마킹 제, 김서림 방지제, 충전제 및 강화제를 포함하는 군으로부터 선택된다.
적합한 광 안정화제는 예를 들어 2-(2'-hydroxyphenyl) benzotriazoles, 2-hydroxy benzophenones, benzoic acids의 esters, acrylates, oxamides, 및 2-(2-hydroxyphenyl)-1,3,-5-triazines에 기초한 화합물이다.
적합한 2-(2´-hydroxyphenyl) benzotriazoles은 예를 들어, 2-(2'-hydroxy-5'methylphenyl) benzotriazole, 2-(3',5'-di-tert-butyl-2'-hydroxyphenyl) benzo-triazole, 2-(5'-tert-butyl-2'-hydroxy-phenyl) benzotriazole, 2-(2'-hydroxy-5'-(1,1,3,3-tetramethylbutyl) phenyl) benzotriazole, 2-(3',5'-di-tert-butyl-2'-hydroxyphenyl)-5-chlorobenzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-methyl-phenyl-5-chlorobenzotriazole, 2-(3'-sec-butyl-5'-ter-butyl-2'-hydroxy-phenyl) benzotriazole, 2-(2'-hydroxy-4'-octyloxyphenyl) benzotriazole, 2-(3',5'-di-tert-amyl-2'-hydroxyphenyl) benzotriazole, 2-(3',5'-bis(α,α-dimethyl-benzyl)-2'-hydroxy-phenyl) benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-octyl-oxy-carbonyl-ethyl)phenyl)-5-chlorobenzotriazole, 2-(3'-tert-butyl-5'-[2-(2-ethylhexyloxy)carbonylethyl]-2'-hydroxyphenyl)-5-chlorobenzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl)-5-chloro-benzo-tri-azole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)phenyl)-5-benzo-triazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-octyloxycarbonylethyl)phenyl) benzo-triazole, 2-(3'-tert-butyl-5'-[2-(2-ethylhexyloxy) carbonylethyl]-2'-hydroxyphenyl) benzotriazole, 2-(3'-dodecyl-2'-hydroxy-5'-methylphenyl) benzotriazole, 2-(3'-tert-butyl-2'-hydroxy-5'-(2-isooctyloxycarbonylethyl) phenylbenzotriazole, 2,2'-methylenebis[4-(1,1,3,3-tetramethylbutyl)-6-benzo-triazole-2-ylphenol]; poly-ethylene glycole 300과 2-[3'-tert-butyl-5'-(2-methoxycarbonylethyl)-2'-hydroxyphenyl]-2H-benzotriazole의 에스테르 교환반응의 생성물; [R―CH2CH2―COO―CH2CH2-]-2이다, 여기서R은 3'-tert-butyl-4'-hydroxy-5'-2H-benzotriazole-2-ylphenyl, 2-[2'-hydroxy-3'-(α,α-dimethyl-benzyl)-5'-(1,1,3,3-tetramethylbutyl)phenyl] benzotriazole, 2-[2'-hydroxy-3'-(1,1,3,3-tetramethylbutyl)-5'-(α,α-dimethylbenzyl)phenyl] benzotriazole.
적합한 2-hydroxybenzophenones는 예를 들어4-hydroxy-, 4-methoxy-, 4-octyloxy-, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2',4'-trihydroxy- 및 2-hydroxy benzophenones의 2'-hydroxy-4,4'-dimethyoxy 유도체이다.β
적합한 아크릴레이트는 예를 들어ethyl-α-cyano-β,β-diphenylacrylate, isooctyl-α-cyano-β,β-diphenylacrylate, methyl-α-carbomethoxycinnamate, methyl-α-cyano-β-methyl-p-methoxycinnamate, butyl-α-cyano-β-methyl-p-methoxycinnamate, methyl-α-carbomethoxy-p-methoxycinnamate 및 N-(β-carbomethoxy-β-cyanovinyl)-2-methylindoline이다.
벤조산의 적합한 에스테르는 예를 들어, 4-tert-butylphenyl salicylate, phenylsalicylate, octylphenylsalicylate, dibenzoyl resorcinol, bis(4-tert-butylbenzoyl)resorcinol, benzoyl resorcinol, 2,4-di-tert-butylphenyl-3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl-3,5-di-tert-butyl-4-hydroxybenzoate, octadecyl-3,5-di-tert-butyl-4-hydroxybenzoate, 2-methyl-4,6-di-tert-butyl-phenyl-3,5-di-tert-butyl-4-hydroxybenzoate이다.
적합한 옥사미드(oxamide)는 예를들어 4,4'-dioctyloxyoxanilide, 2,2'-di-ethoxy-oxanilide, 2,2'-dioctyloxy-5,5'-di-tert-butoxanilide, 2,2'-didodecyloxy-5,5'-di-tert-butoxanilide, 2-ethoxy-2'-ethyloxanilide, N,N'-bis(3-dimethylaminopropyl) oxamide, 2-ethoxy-5-tert-butyl-2'-ethoxanilide 및 2-ethoxy-2'-ethyl-5,4'-di-tert-butoxanilide와의 혼합물, o-and p-methoxy- disubstituted oxanilides 의 혼합물 및 o-and p-ethoxy-disubstituted oxanilides 의 혼합물이다.
적합한 2-(2-hydroxyphenyl)-1,3,5-triazines은, 예를 들어, 2,4,6-tris(2-hydroxy-4-octyloxyphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2,4-dihydroxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2,4-bis(2-hydroxy-4-propyloxyphenyl)-6-(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-octyloxyphenyl)-4,6-bis(4-methyl-phenyl-1,3,5-triazine, 2-(2-hydroxy-4-dodecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-(2-hydroxy-4-tridecyloxyphenyl)-4,6-bis(2,4-dimethylphenyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3-butyl-oxy-pro-poxy)-phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3-octyloxypropyloxy)phenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazine, 2-[4-(do-decyl-oxy/tridecyloxy-2-hydroxypropoxy)-2-hydroxyphenyl]-4,6-bis-(2,4-di-methyl-phenyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3-do-decyl-oxy-propoxy)-phenyl]-4,6-bis(2,4-dimethylphenyl-1,3,5-triazine, 2-(2-hydroxy-4-hexyloxy)-phenyl-4,6-diphenyl-1,3,5-triazine, 2-(2-hydroxy-4-methoxyphenyl)-4,6-diphenyl-1,3,5-triazine, 2,4,6-tris[2-hydroxy-4-(3-butoxy-2-hydroxypro-poxy)-phenyl]-1,3,5-triazine, 2-(2-hydroxyphenyl)-4-(4-methoxyphenyl)-6-phenyl-1,3,5-triazine, 2-{2-hydroxy-4-[3-(2-ethylhexyl-1-oxy)-2-hydroxy-propyl-oxy]-phenyl}-4,6-bis(2,4-dimethylphenyl-1,3,5-triazine이다.
적합한 금속 불활성화제는, 예를 들어, N,N'-diphenyloxamide, N-salicylal-N'-salicyloylhydrazine, N,N'-bis(salicyloyl)hydrazine, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazine, 3-salicyloylamino-1,2,4-triazole, bis(benzylidene)oxalyldihydrazide, oxanilide, isophthaloyldihydrazide, sebacoyl-bis-phenylhydrazide, N,N'-diacetyladipoyldihydrazide, N,N'-bis-(salicyl-oyl)oxylyldihydrazide, N,N'-bis(salicyloyl)thiopropionyldihydrazide이다.
적합한 페놀계 산화 방지제는, 예를 들어:
2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methyl-phenol, 2-(α-methylcyclohexyl)-4,6-dimethylphenol, 2,6-dioctadecyl-4-methyl-phenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxy-methylphenol와 같은 알킬화 모노페놀, 2,6-dinonyl-4-methylphenol, 2,4-dimethyl-6-(1'-methylundec-1'-yl)phenol, 2,4-dimethyl-6-(1'-methylheptadec-1'-yl)phenol, 2,4-dimethyl-6-(1'-methyltridec-1'-yl)phenol 과 같은 선형 또는 분지형 노닐페놀 및 이들의 혼합물;
2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-didodecylthiomethyl-4-nonylphenol와 같은 alkylthio methylphenols;
2,6-di-tert-butyl-4-methyoxyphenol, 2,5-di-tert-butylhydrocquinone, 2,5-di-tert-amyl-hydro-quinone, 2,6-diphenyl-4-octadecyloxyphenol, 2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyphenylstearate, bis(3,5-di-tert-butyl-4-hydroxyl-phenyl)-adipate과 같은 hydroquinones 및 alklyated hydroquinones;
α-, β-, γ-, δ-토코페롤 및 이들의 혼합물 (비타민 E)과 같은 토코페롤;
2,2'-thiobis(6-tert-butyl-4-methylphenol), 2,2'-thiobis(4-octylphenol), 4,4'-thiobis(6-tert-butyl-3-methylphenol), 4,4'-thiobis(6-tert-butyl-2-methylphenol), 4,4'-thiobis(3,6-di-sec-amylphenol), 4,4'-bis(2,6-dimethyl-4-hydroxyphenyl)disulfide와 같은 hydroxylated thiodiphenylether;
2,2'methylenebis(6-tert-butyl-4-methylphenol), 2,2'-methylenebis(6-tert-butyl-4-ethylphenol), 2,2'-methylenebis[4-methyl-6-(α-methylcyclohexyl)phenol], 2,2'-methylenebis(4-methyl-6-cyclhexylphenol), 2,2'-methylenebis(6-nonyl-4-methylphenol), 2,2'-methylenebis(4,6-di-tert-butylphenol), 2,2'-ethylidenebis(4,6-di-tert-butylphenol), 2,2'-ethylidenebis(6-tert-butyl-4-isobutylphenol), 2,2'-methylenebis[6-(α-methylbenzyl)-4-nonyl-phenol], 2,2'-methylenebis[6-(α,α-dimethylbenzyl)-4-nonylphenol], 4,4'-methylene-bis(2,6-di-tert-butylphenol, 4,4'-methylenebis(6-tert-butyl-2-methyl-phenol), 1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butane, 2,6-bis-(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol, 1,1,3-tris(5-tert-butyl-4-hydroxy-2-methylphenyl)butane, 1,1-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)-3-n-dodecylmercaptobutane, ethyleneglycol-bis[3,3-bis(3'-tert-butyl-4'-hydroxyphenyl)butyrate], bis(3-tert-butyl-4-hydroxy-5-methylphenyl)-di-cyclopentadiene, bis[2-(3'-tert-butyl-2'-hydroxy-5'-methylbenzyl)-6-tert-butyl-4-methylphenyl]terephthalate, 1,1-bis-(3,5-dimethyl-2-hydroxy-phenyl)-butane, 2,2-bis(3,5-di-tert-butyl-4-hydroxyphenyl)propane, 2,2-bis-(5-tert-butyl-4-hydroxy-2-methylphenyl)-4-n-dodecylmercaptobutane, 1,1,5,5-tetra(5-tert-butyl-4-hydroxy-2-methylphenyl)pentane와 같은 alkylide bisphenols;
3,5,3',5'-tetra-tert-butyl-4,4'-dihydroxydibenzylether, octadecyl-4-hydroxy-3,5-dimethylbenzyl-mercapto-acetate, tridecyl-4-hydroxy-3,5-di-tert-butylbenzylmercaptoacetate, tris(3,5-di-tert-butyl-4-hydroxybenzyl)amine, bis(4-tert-butyl-3-hydroxy-2,6-di-methyl-benzyl)di-thioterephthalate, bis(3,5-di-tert-butyl-4-hydroxybenzyl)sulfide, iso-octyl-3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetate와 같은 O-, N- 및 S-벤질 화합물;
dioctadecyl-2,2-bis(3,5-di-tert-butyl-2-hydroxybenzyl)malonate, dioctadecyl-2-(3-tert-butyl-4-hydroxy-5-methyl-benzyl)-malonate, didodecylmercaptoethyl-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate, bis[4-(1,1,3,3-tetramethylbutyl)phenyl]-2,2-bis(3,5-di-tert-butyl-4-hydroxybenzyl)malonate와 같은 hydroxybenzylated malonates;
1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene, 1,4-bis(3,5-di-tert-butyl-4-hydroxy-benzyl)-2,3,5,6-tetramethylbenzene, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxy-benzyl)-phenol와 같은 방향족 히드록시벤질 화합물;
2,4-bis(octylmercapto)-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hy-droxy-anilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis(3,5-di-tert-butyl-4-hydroxy-phenoxy)-1,3,5-triazine, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxy-phenoxy)-1,2,3-triazine, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-iso-cyanurate, 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate, 2,4,6-tris(3,5-di-tert-butyl-4-hydroxphenylethyl)-1,3,5-triazine, 1,3,5-tris(3,5-di-tert-butyl-4-hydroyphenylpropionyl)hexahydro-1,3,5-triazine, 1,3,5-tris(3,5-dicyclohexyl-4-hydroxybenzyl)isocyanurate와 같은 triazine 화합물;
dimethyl-2,5-di-tert-butyl-4-hydroxy-benzyl-phos-phonate, dietyhl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl-5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate, 3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid의 모노에틸 에스테르의 칼슘염과 같은 benzylphosphonates;
4-hydroxylauranilide, 4-hydroxystearanilide, octyl-N-(3,5-di-tert-butyl-4-hydroxyphenyl)carbamate와 같은 acylaminophenols;
β-(3,5-Di-tert-butyl-4-hydroxyphenyl)propionic acid와 1가 또는 다가 알코올, 예를들어 methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethyleneglycol, 1,2-propanediol, neopentylglycol, thiodiethyleneglycol, diethyleneglycol, tri-ethylene-glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamied, 3-thiaundecanol, 3-thiapentadecanol, tri-methyl-hexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-tri-oxa-bi-cyclo-[2.2.2]octane의 에스테르;
β-(5-tert-butyl-4-hydroxy-3-methylphenyl)propionic acid와, methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethyleneglycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxyethyl)oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethyl-hexane-diol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-tri-oxa-bicyclo[2.2.2]octane, 3,9-bis[2-{3-(3-tert-butyl-4-hydroxy-5-methyl-phenyl)-propionyloxy}-1,1-dimethylethyl]-2,4,8,10-tetraoxaspiro[5.5]undecane와 같은 1가 또는 다가 알코올의 에스테르;
β-(3,5-dicyclohexyl-4-hydroxyphenyl)propionic acid와 methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethyleneglycol, 1,2-propanediol, neopentylglycol, thiodiethyleneglycol, diethyleneglycol, triethyleneglycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis(hydroxy-ethyl)-oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo-[2.2.2]-octane와 같은 1가 또는 다가 알코올의 에스테르;
(3,5-di-tert-butyl-4-hydroxyphenyl)acetic acid와 1가 또는 다가 알코올, 예를 들어 methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris(hydroxyethyl)isocyanurate, N,N'-bis-(hydroxy-ethyl)-oxamide, 3-thiaundecanol, 3-Thiapentadecanol, trimethylhexanediol, tri-methylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabi-cyclo-[2.2.2]-octane의 에스테르;
N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylene diamide, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylene diamide, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hexamethylene diamide, N,N'-bis(3,5-di-tert-butyl-4-hydroxyphenylpropionyl)hydrazide, N,N'-bis[2-(3-[3,5-di-tert-butyl-4-hydroxyphenyl]propionyloxy)ethyl]oxamide (Naugard®XL-1, marketed by Uniroyal)와 같은 β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid 의 아미드;
아스코르브산(비타민 C)이다.
특히 바람직한 페놀 계 산화 방지제는 다음을 포함한다 :
octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, pentaerythritol-tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, tris(3,5-di-tert-butyl-4-hydroxyphenyl)isocyanurate, 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxyphenyl)isocyanurate, 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxy-benzyl)benzol, triethylene glycol-bis[3-(3-tert-butyl-4-hydroxy-5-methyl-phenyl)propionate, N,N'-hexane-1,6-diyl-bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid amide.
적합한 포스파이트 / 포스포나이트는 예를 들어:
triphenylphosphite, diphenylalkylphosphites, phenyldialkylphosphites, tri(nonylphenyl)phosphite, trilaurylphosphites, trioctadecylphosphite, distearylpentaerythritoldiphosphite, tris-(2,4-di-tert-butylphenyl phosphite, diisodecylpentaerythritoldiphosphite, bis(2,4-di-tert-butylphenyl)-penta-erythritoldiphosphite, bis(2,4-di-cumylphenyl)pentaerythritoldiphosphite, bis(2,6-di-tert-butyl-4-methylphenyl)pentaerythritoldiphosphite, diisodecyloxypentaerythritoldiphosphite, bis(2,4-di-tert-butyl-6-methyl-phenyl)-pentaerythritoldiphosphite, bis(2,4,6-tris(tert-butylphenyl)-penta-erythritoldiphosphite, tristearylsorbitoltriphosphite, tetrakis(2,4-di-tert-butylphenyl)-4,4'-biphenylene diphosphonite, 6-isooctyloxy-2,4,8,10-tetra-tert-butyl-12H-dibenz[d,g]-1,3,2-dioxaphosphocine, bis(2,4-di-tert-butyl-6-methylphenyl)methylphosphite, bis(2,4-di-tert-butyl-6-methylphenyl)-ethyl-phos-phite, 6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-dibenz[d,g]-1,3,2-di-oxa-phosphocine, 2,2'2''-nitrilo[triethyltris(3,3'',5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl)phosphite], 2-ethylhexyl(3,3',5,5'-tetra-tert-butyl-1,1'-bi-phenyl-2,2'-diyl))phosphite, 5-butyl-5-ethyl-2-(2,4,6-tri-tert-butylphenoxy)-1,3,2-dioxaphosphirane이다.
특히 바람직한 포스파이트/포스포나이트는:
여기서 n은 1과 100 사이 일 수 있다.
추가로 적합한 안정화제는 아민계 산화방지제이다.
적합한 아민계 산화방지제는, 예를 들어:
N,N'-di-isopropyl-p-phenylene diamine, N,N'-di-sec-butyl-p-phenylene di-amine, N,N'-bis(1,4-dimethylpentyl)-p-phenylene diamine, N,N'-bis(1-ethyl-3-methylpentyl)-p-phenylene diamine, N,N'-bis(1-methylheptyl)-p-phenylene diamine, N,N'-dicyclohexyl-p-phenylene diamine, N,N'-diphenyl-p-phenylene diamine, N,N'-bis(2-naphthyl)-p-phenylene diamine, N-isopropyl-N'-phenyl-p-phenylene diamine, N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylene-diamine, N-(1-methylheptyl)-N'-phenyl-p-phenylene diamin, N-cyclohexyl-N'-phenyl-p-phenylene diamine, 4-(p-toluene-sulfamoyl)-di-phenyl-amine, N,N'-dimethyl-N,N'-di-sec-butyl-p-phenylene diamine, Diphenyl-amine, N-allyldiphenylamine, 4-isopropoxydiphenylamine, N-phenyl-1-naph-thyl-amine, N-(4-tert-octylphenyl)-1-naphthylamine, N-phenyl-2-naphthyl-amine, octylated diphenylamine, 예를 들어 p,p'-di-tert-octyldiphenylamine, 4-n-butylaminophenol, 4-butyrylaminophenol, 4-nonanoylaminophenol, 4-do-decanoyl-aminophenol, 4-octadecanoylamino-phenol, bis(4-methoxy-phenyl)-amine, 2,6-di-tert-butyl-4-dimethylaminomethyl-phenol, 2,4'-diamino-di-phenyl-methane, 4,4'-diaminodiphenylmethane, N,N,N',N'-tetra-methyl-4,4'-diaminodiphenylmethane, 1,2-bis[(2-methyl-phenyl)amino]ethane, 1,2-bis-(phenyl-amino)propane, (o-tolyl)biguanide, bis[4-(1',3'-dimethyl-butyl)-phenyl]amine, tert-octylated N-phenyl-1-naphthylamine, mono-alkylated 및 dialkylated tert-butyl/tert-octyldiphenylamines의 혼합물, monoalkylated 및 dialkylated nonyldiphenylamines의 혼합물, monoalkylated 및 dialkylated dodecyldiphenylamines의 혼합물, monoalkylated 및 dialkylated isopropyl/isohexyl-diphenylamines의 혼합물, monoalkylated 및 dialkylated tert-butyldiphenylamines의 혼합물, 2,3-dihydro-3,3-dimethyl-4H-1,4-benzothiazine, phenothiazine, monoalkylated 및 dialkylatedvtert-butyl/tert-octylphenothiazines의 혼합물, mono-alkylated 및 dialkylated tert-octylphenothiazines의 혼합물, N-allylphenothiazine, N,N,N',N'-tetraphenyl-1,4-diaminobut-2-ene 및 이들의 혼합물 또는 조합.
바람직한 아민계 산화 방지제는 다음을 포함한다: N,N'-di-isopropyl-p-phenylene diamine, N,N'-di-sec-butyl-p-phenylene diamine, N,N'-bis(1,4-dimethylpentyl)-p-phenylene diamine, N,N'-bis(1-ethyl-3-methylpentyl)-p-phenylene diamine, N,N'-bis(1-methylheptyl)-p-phenylene diamine, N,N'-dicyclohexyl-p-phenylene diamine, N,N'-diphenyl-p-phenylene diamine, N,N'-bis(2-naphthyl)-p-phenylene diamine, N-isopropyl-N'-phenyl-p-phenylene diamine, N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylene-diamine, N-(1-methylheptyl)-N'-phenyl-p-phenylene diamine, N-cyclohexyl-N'-phenyl-p-phenylene diamine.
추가의 바람직한 아민계 산화방지제는 N,N-dialkylhydroxylamines, N,N-dibenzylhydroxylamine, N,N-dilaurylhydroxylamine, N,N-distearylhydroxylamine, N-benzyl-α-phenylnitron, N-octadecyl-α-hexadecylnitron과 같은 hydroxylamines 또는 N-oxides (nitrons), 및 하기 화학식에 따른 Genox EP (Addivant)이다:
추가로 적합한 안정 화제는 티오시너지트(thiosynergist)이다.
적합한 티오시너지스트는 예를 들어, distearylthiodipropionate, di-lauryl-thiodipropionate; ditridecyldithiopropionate, ditetradecylthiodipropionate, 3-(dodecylthio)-, 1,1'-[2,2-bis[[3-(dodecylthio)-1-oxopropoxy]methyl]-1,3-pro-pane-diyl]propanoic acid ester이다.
특히 폴리아미드에 대한 추가의 안정화제는, copper-(1)-iodide, copper-(I) bromide와 같은 구리염, 또는 triphenylphosphine copper-(I) complexes와 같은 구리 착물이다.
추가로 적합한 안정화제는 3-(4-(2-acetoxyethoxy)phenyl]-5,7-di-tert-butyl-benzofuran-2-one, 5,7-di-tert-butyl-3-[4-(2-stearoyloxyethoxy)phenyl]benzofuran-2-one, 3,3'-bis[5,7-di-tert-butyl-3-(4-(2-hydroxyethoxy]phenyl)benzofuran-2-one), 5,7-di-tert-butyl-3-(4-ethoxyphenyl)benzofuran-2-one, 3-(4-acetoxy-3,5-dimethyl-phenyl)-5,7-di-tert-butyl-benzofuran-2-one, 3-(3,5-dimethyl-4-pivaloyl-oxy-phenyl)-5,7-di-tert-butyl-benzofuran-2-one, 3-(3,4-dimethylphenyl)-5,7-di-tert-butyl-benzofuran-2-one, 3-(2,3-dimethylphenyl)-5,7-di-tert-butyl-benzo-furan-2-one와 같은 벤조푸라논(benzofuranone) 및 인돌리논(indolinone)이다 .
적합한 장애 아민은, 예를 들어 1,1-bis(2,2,6,6-tetramethyl-4-piperidyl)succinate, bis(1,2,2,6,6-pentamethyl-4-piperidyl)sebacate, bis(1-octyloxy-2,2,6,6-tetramethyl-4-piperidyl)sebacate, bis(1,2,2,6,6-penta-methyl-4-piperidyl)-n-butyl-3,5-di-tert-butyl-4-hydroxybenzylmalonaet, 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine 및 succinic acid의 축합생성물, N,N'-bis(2 ,2,6,6-tetramethyl-4-piperidyl )hexamethylene diamine 및4-tert-octylamino-2,6-dichloro-1,3,5-triazine의 선형 또는 환형 축합생성물, tris(2,2,6,6-tetramethyl-4-piperidyl)-nitrilo-triacetate, tetrakis(2,2,6,6-tetramethyl-4-piperidyl)-1,2,3,4-butane tetracarboxylate, 1,1'-(1,2-ethandiyl)-bis(3,3,5,5-tetramethylpiperazinone), 4-benzoyl-2,2,6,6-tetramethylpiperidine, 4-stearyloxy-2,2,6,6-tetramethyl-piperidine, N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylene diamine 및 4-morpholino-2,6-dichloro-1,3,5-triazine의 선형 또는 환형 축합생성물, 7,7,9,9-tetramethyl-2-cycloundecyl-1-oxa-3,8-diaza-4-oxospiro-[4,5]decane 및 epichlorhydrine의 반응 생성물이다.
하기 구조의 올리고머 및 폴리머 장애 아민이 바람직하다:
상기 화합물에서, n은 각각 3 내지 100을 의미한다.
적합한 분산제는, 예를 들어:
polyacrylates, 예를 들어 장쇄 측기를 갖는 공중합체, polyacrylate block copolymers, alkylamides: 예를 들어 N,N'-1,2-ethanediylbisoctadecanamide sorbitan ester, 예를 들어 monostearylsorbitan esters, titanates 및 zirconates, 관능기를 갖는 반응성 공중합체, 예를 들어 polypropylene-co-acrylic acid, polypropylene-co-maleic acid anhydride, polyethylene-co-glycidyl-meth-acrylate, polystyrene-alt-maleic acid anhydride-polysiloxanes: 예를 들어 dimethyl-silanodiole-ethylene-oxide copolymers, polyphenylsiloxane copolymers, amphiphilic copolymers: 예를 들어 polyethylene-block-polyethylene oxide, dendrimers, 예를 들어 히드록실기를 함유하는 dendrimers 이다.
적합한 핵 형성제는, 예를 들어, 벤조산, 숙신산, 아디프산과 같은 일작용성 및 다 작용성 카르복실산의 활석, 알칼리 또는 알칼리 토류 염이고, 예를 들어 sodium benzoate, zink glycerolate, aluminum hydroxy-bis(4-tert- butyl)benzoate, 1,3:2,4-bis(4-methylbenzylidene)sorbitol와 같은 benzylidene sorbitols, 2,2'-methylene-bis-(4,6-di-tert-butyl-phenyl)phosphate, 및 trimesic acid tricyclohexylamide, trimesic acid tri(4-methylcyclo-hexylamide), trimesic acid tri(tert-butylamide), N,N´,N´´-1,3,5-benzoltriyltris(2,2-dimethyl-propanamide) 또는 2,6-naphthalindicarboxylic acid-cyclohexylamide 와 같은 trisamides 및 diamides이다.
적합한 핵형성 방지제는 니그로신과 같은 아진 염료이다.
적합한 난연제는 예를 들어:
a) AI(OH)3, Mg(OH)2, AIO(OH), MgCO3와 같은 무기 난연제, 몬모릴로나이트(montmorillonite) 또는 세피올라이트(sepiolite)와 같은 시트 실리케이트(sheet silicates), Mg-Al-실리케이트, POSS (polyhedral oligomeric silsesquioxanes) 화합물, 헌타이트 하이드로마그네사이트(huntite hydromagnesite) 또는 할로이사이트(halloysite) 및 Sb2O3, Sb2O5, MoO3, 아연 스타네이트(zinc stannate), 아연 히드록시스타 네이트(zinc hydroxystannate),
b) 질소를 함유 한 방염제, 예컨대 멜라민, 멜렘, 멜람, 멜론, 멜라민 유도체, 멜라민 축합 생성물 또는 멜라민 염, 벤조구아 나민, 폴리이소시아누레이트, 알란토인, 포스파젠, 특히 멜라민 시아누레이트, 멜라민 포스페이트, 디멜라민 포스페이트, 멜라민 파이로포스페이트, 멜라민 폴리포스페이트, 멜라민 메탈 포스페이트, 예컨대 멜라민 알루미늄 포스페이트, 멜라민 아연 포스페이트, 멜라민 마그네슘 포스페이트 및 상응하는 파이로포스페이트 및 폴리포스페이트, poly-[2,4-(piperazine-1,4-yl)-6-(morpholine-4-yl)-1,3,5-triazine], 암모늄 폴리포스페이트, 멜라민 보레이트, 멜라민 하이드로 브로마이드,
c) 라디칼 형성제 예를 들어 알콕시 아민, 히드록실 아민 에스테르, 아조 화합물, 디쿠밀 또는 폴리쿠밀, 히드록시이미드 및 이들의 유도체, 예컨대 히드록시이미드 에스테르 또는 히드록시이미드 에테르,
d) 인을 함유한 난연제 예를 들면, 적색 인, 레조르신 디포스페이트(resorcin diphosphte)와 같은 포스페이트, 비스페놀-A-디포스페이트 및 이들의 올리고머, 트리페닐포스페이트, 에틸렌 디아민 디포스페이트, 차아인산의 염과 같은 포스피네이트 및 알킬포스피네이트 염과 같은 이들의 유도체, 예를 들어 디에틸포스피네이트 알루미늄 또는 디에틸포스피네이트 아연 또는 알루미늄 포스 피네이트, 알루미늄 포스파이트, 알루미늄 포스포네이트, 포스포네이트 에스테르, 올리고머 및 메탄 포스폰산의 중합체 유도체, 9,10-dihydro-9-oxa-10-phosphorylphenanthrene-10-oxide (DOPO) 및 이들의 치환된 화합물,
e) 폴리브롬화 디페닐 옥사이드와 같은 염소 및 브롬에 기초한 할로겐화 방염제, 예를 들어 데카브로모디페닐옥사이드, tris(3-bromo-2,2-bis (bromo-methyl)-propyl-phosphate, tris(tribromoneopentyl)-phosphate, 테트라브로모프탈산, 1,2-bis(tribromophenoxy)ethane, 헥사브로모시클로도데칸, 브롬화 디페닐에탄, tris-(2,3-dibrompropyl)isocyanurate, ethylene-bis-(tetrabromo-phthal-imide), 테트라브로모-비스페놀 A, 브롬화 폴리스티렌, 브롬화 폴리부타디엔 또는 폴리스티렌 브롬화 폴리부타디엔 공중 합체, 브롬화 폴리페닐렌 에테르, 브롬화 에폭시 수지, 폴리펜타브로모벤질아크릴레이트, 선택적으로 Sb2O3 및 / 또는 Sb2O5와 조합,
f) 선택적으로 실리카와 같은 담체 물질 상에 아연 붕산염 또는 칼슘 붕산염과 같은 붕산염.
g) 원소 황, 디설파이드 및 폴리설파이드, 티우람 설파이드, 디티오카바메이트, 머캅토벤조티아졸 및 설펜아미드와 같은 황을 함유하는 화합물,
h) 폴리테트라플루오르에틸렌과 같은 적하 방지제(antidrip agent),
i) 폴리페닐실록산과 같은 규소 함유 화합물,
j) 탄소 나노 튜브 (CNT), 팽창 흑연 또는 그래핀과 같은 탄소 변형
및 이들의 조합 또는 혼합물이다.
적합한 충전제 및 보강제는 예를 들어 칼슘 카보네이트, 실리케이트, 유리 섬유, 유리 구체 (고체 또는 중공), 활석, 미크라(micra), 카올린, 바륨 설페이트, 금속 산화물 및 금속 수산화물, 블랙 카본, 흑연, 탄소 나노 튜브, 그래핀, 목재 가루 또는 셀룰로오스 또는 합성 섬유와 같은 천연 제품의 섬유와 같은 합성 또는 천연 재료이다. 추가의 적합한 충전제는 몬트모릴로나이트, 벤토나이트, 바이델라이트, 운모, 헥토라이트, 사포나이트, 질석, 레디카이트(ledikite), 마가다이트, 일라이트, 카올리나이트, 규회석, 아타풀자이트와 같은 하이드로탈사이트 또는 제올라이트 또는 필로실리케이트를 포함한다.
적합한 안료는 무기 또는 유기 성질 일 수있다. 무기 안료는 예를 들어 이산화 티타늄, 산화 아연, 황화 아연, 산화철, 울트라마린, 블랙 카본이다; 유기 안료는 예를 들어 안트라퀴논, 안트라트론, 벤즈이미다졸론(benzimidazolone), chinacridone, 디케토피롤로피롤(di-keto-pyrrolopyrrol), 디옥사진, 인단트론, 이소인돌린, 아조화합물, 페릴렌, 프탈로시아닌 또는 피란트론이다. 추가로 적합한 안료는 금속 기재상의 효과 안료 또는 금속 산화물 기재상의 진주 광택 안료를 포함한다.
폴리에스테르 또는 폴리아미드와 같은 중축합 중합체의 선형 분자량 구조에 적합한 사슬 연장제는 예를 들어 디에폭사이드, 비스-옥사졸린, 비스-옥사졸론, 비스-옥사진, 디이소시아네이트, 디안하이드라이드(dianhydride), 비스-아실락탐, 비스-말레이미드, 디시아네이트, 카보디이미드이다. 추가로 적합한 사슬 연장제는 폴리스티렌 폴리아크릴레이트 폴리글리시딜(메트)아크릴레이트 공중 합체, 폴리스티렌 말레산 무수물 공중 합체 및 폴리에틸렌 말레산 무수물 공중 합체와 같은 중합체 화합물을 포함한다.
적합한 형광 증백제는 예를 들어 비스-벤즈옥사졸, 페닐 쿠마린 또는 비스 (스티릴) 비페닐 및 특히 하기 화학식의 형광 증백제이다 :
적합한 충전제 불활성화제는 예를 들어 에폭사이드, 예컨대 비스-페놀-A-디글리시딜에테르, 폴리실록산, 폴리아크릴레이트, 특히 폴리메타크릴산 폴리알킬렌 옥사이드와 같은 블록 공중합체이다.
적합한 정전기 방지제는 예를 들어 에톡실화 알킬아민, 지방산 에스테르, 알킬설포네이트 및 폴리에테르아미드와 같은 중합체이다.
적합한 오존분해방지제는 상기 언급된 아민, 예컨대 N,N'-di-isopropyl-p-phenylene diamine, N,N'-di-sec-butyl-p-phenylene diamine, N,N'-bis(1,4-dimethylpentyl)-p-phenylene diamine, N,N'-dicyclohexyl-p-phenylene di-amine, N-isopropyl-N'-phenyl-p-phenylene diamine, N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylene diamine, N-(1-methylheptyl)-N'-phenyl-p-phenylene diamine, N-cyclohexyl-N'-phenyl-p-phenylene diamine이다.
적합한 탈형 보조제는 예를 들어 몬탄 왁스이다.
포스 파이트, 포스포나이트, 히드록시라민 또는 니트론을 포함하는 군으로부터 선택된하기 첨가제는 본 발명에 따른 조성물에 매우 특히 바람직하게 포함된다.
또한, 본 발명은 특히 산화적, 열적 또는 광화학선 분해 또는 손상과 관련하여 안정화 될 유기 성분을 안정화시키는 방법에 관한 것으로, 여기서 하나 이상의 화합물이 안정화 될 유기 성분과 혼합되거나 또는 그것으로 가공된다.
이러한 안정화 방법의 바람직한 실시예는 예를 들어 본 발명에 따른 화합물이 분말, 펠릿, 용액, 액체, 현탁액, 에멀젼 또는 플레이크로 존재할 수 있거나 및 안정화 될 유기 성분, 특히 안정화 될 중합체 또는 플라스틱 혼합물과의 용융물로 이송되고, 이어서 냉각되는 것을 제공한다. 이에 대한 대안으로, 화학식 I의 화합물을 용융된 상태의 중합체 용융물에 도입하는 것도 동일하게 가능하다.
추가 성분이 중합체 조성물에 첨가되는 경우, 이들은 액체, 분말, 분산액, 유제, 펠렛 또는 압축된 제품의 형태로, 또는 본 발명에 따른 첨가제 조성물과 함께 상기 기재된 바와 같이 중합체에 별도로 첨가 될 수있다.
화학식 I에 따른 본 발명에 따른 상기 기재된 화합물 및 임의로 플라스틱에의 추가 첨가제의 가공은 통상적 인 가공 방법에 의해 수행되며, 여기서 중합체는 용융되고 화학식 I에 따른 본 발명에 따른 화합물 및 임의의 추가 첨가제, 바람직하게는 믹서, 혼련 기 및 압출기에 의해 혼합된다. 바람직하게 진공 탈기 장치가 장착 된 단축 압출기, 이축 압출기, 유성 기어 압출기, 링 압출기 및 코-니더(co-kneader)와 같은 압출기가 가공 기계로서 바람직하다. 처리는 여기서 공기 중에서 또는 임의로 질소와 같은 불활성 기체 조건 하에서 수행 될 수있다.
또한, 화학식 I에 따른 본 발명에 따른 화합물은 예를 들어 중합체에서 본 발명에 따른 조성물의 10-90 %를 포함하는 소위 마스터 배치 또는 농축 물의 형태로 제조 및 도입 될 수있다.
또한, 본 발명은 산화 분해 또는 산화 손상에 대해 유기 물질을 안정화시키기위한 화학식 I에 따른 본 발명에 따른 화합물의 용도에 관한 것이다.
본 발명은 본 발명을 제한하지 않고 다음의 설명을 참조하여 보다 상세하게 설명 될 것이다.
바람직한 실시예:
방법:
알릴 화합물 또는 비닐 화합물 또는 마이클 수용체의 전환은 바람직하게는 촉매의 도움으로 알코올 그룹을 추가로 포함하는 티올 화합물과의 제 1 반응 단계에서 발생하고, 제 2 반응 단계에서, 알콜 기의 에스테르 교환은 입체 장애 페놀기를 포함하는 에스테르 화합물과 일어난다. 티올 화합물로서 메르캅토 에탄올, 3- 메르 캅토 프로판올, 2- 메르 캅토 프로판올 및 1- 메르 캅토 부탄올 및 티오 글리세롤이 특히 바람직하다. 추가로 바람직한 방법은 아래와 같은 입체 장애 페놀기를 포함하는 티오 프로필 화합물의 전환이다.
반응은 바람직하게는 촉매의 존재하에 수행되고; 바람직한 촉매는 광개시제, 아조-스타터 또는 과산화물과 같은 라디칼 발생 화합물이고, 마이클 수용체의 경우, sodium methanolate, tritheylamine과 같은 염기 또는 1-methylimide azole과 같은 친핵체 또는 dimethylphenylphosphine과 같은 alkylphosphine이다.
반응은 물질 및 용매 모두에서 수행 될 수 있으며; 바람직한 용매는 toluol, N-methyl-2-pyrrolidone 또는 N,N-dimethylformamide와 같은 불활성 용매이다. 용매로서 메탄올이 더 사용된다. 물질에서 특히 바람직한 반응은 바람직하게는 용매 / 시너(thinner)로서 티올 성분의 잉여에서 수행된다.
필요한 경우, 제 2 반응 단계는 바람직하게는 입체 장애 페놀기를 보유하는 에스테르로 중간에 형성된 알코올기를 에스테르 교환함으로써 수행된다. 에스테르 교환을 위한 상응하는 방법 및 촉매는 당업자에게 친숙하며, 예를 들어 문헌 J. Otera, Chem. Rev. 1993, 93, 1449-1470 (인클로저 참조) 또는 WO 86/00301 (인클로저 참조) 또는 WO2004 / 033699 (인클로저 참조)에 기술된다. 주석 오르가닐 또는 티타네이트의 군으로부터의 금속 화합물이 바람직한 촉매이다.
용도:
플라스틱 및 오일 및 지방은 본 발명에 따른 안정 화제에 의해 안정화 될 수있는 바람직한 유기 물질이다.
유기 물질이 오일 및 지방 인 경우, 이들은 미네랄 오일, 식물성 지방 또는 동물성 지방, 또는 예를 들어 합성 에스테르를 기준으로 한 오일, 지방 또는 왁스를 기초로 할 수있다. 식물성 유지는 예를 들어 팜유, 올리브유, 유채유, 아마 인유, 대두유, 해바라기 유, 피마 자유; 동물성 지방은 예를 들어 어유 또는 양의 지방이다.
본 발명에 따른 화합물은 또한 윤활제, 유압 오일, 엔진 오일, 터빈 오일, 트랜스미션 오일, 금속 가공 유체의 안정 화제 또는 윤활 그리스로서 사용될 수있다. 이러한 미네랄 또는 합성 윤활제는 주로 탄화수소를 기본으로 한다.
실시예
I.일반 합성 규칙
본 발명에 따른 안정 화제는, 먼저 알릴 / 비닐 화합물이 알콜 그룹을 운반하는 티올 화합물과 함께 실온에서 또는 승온에서 교반 장치를 사용하여 적합한 반응 용기에서 약간 과량으로, 하기 반응식에 따라, 바람직하게는 UV 조명 하에서 광촉매를 첨가하면서(방법 A), 가열하는 동안 라디칼 스타터를 첨가하면서 (방법 B), 또는 전자 흡인기 (EWG, electron withdrawing group)를 위해, 바람직하게는 염기를 첨가하면서(방법 C) 전환되도록 제조된다:
반응물의 불안정화 또는 탈기(degassing)는 바람직하게는 반응 시작 전에 일어난다. 방법 A의 반응 및 노출 시간은 30 내지 60 분이다. 방법 B에 대한 반응 시간은 4 내지 35 시간이다. 불활성 기체 조건 하에서의 반응이 방법 B에 바람직하다. 방법 C의 반응 시간은 몇 분에 달한다. 여과는 60-100 ℃에서 수성 또는 고진공을 통해 수행된다. 두 번째 단계에서, 에스테르 교환 반응은 하기 반응식에 따라 금속 촉매 하에서 130-180 ℃의 온도에서 입체 장애 페놀기를 약간 과량으로 갖는 에스테르로 수행된다:
생성 된 알콜은 800-20 mbar 범위의 진공을가함으로써 반응 혼합물로부터 제거된다. 여과는 고진공 또는 수성 하에서 일어난다. 용매로 섭취 한 후 금속성 촉매 잔류 물을 흡착 적으로 제거하기 위해 표백 토 또는 다른 흡착제의 첨가가 바람직하다.
II. 본 발명에 따른 실시 예의 합성
a) 본 발명에 따른 실시 예 A의 합성 :
반응식1에 따라,
<반응식1>
15.0 g (0.06 mol, 1 당량) triallylisocyanurate 를 RT에서 자기 교반기를 사용하여 둥근 구 플라스크에서 14.2 g (0.182 몰, 3.02 당량) 2-mercaptoethanol 과 균질화시켰다. 0.1 중량 % phenyl-bis(2,4,-6-trimethylbenzoyl)-phosphinoxide (isocyanurate 에 대한 광개시제)를 혼합물에 첨가하고 λ = 366 nm에서의 UV 조명하에 30 내지 40분 동안 RT에서 교반을 수행한다. 반응 모니터링은 1H NMR 분석을 통해 수행된다. 투명한 저점도 용액을 150 ml 에틸 아세테이트에 수용하고, 각 경우에 50 ml 증류수로 2 회 세척하고, 유기상을 분리하고, 용매를 60 ℃에서 고진공하에 제거 하였다. 투명한 고점도 겔 27.6 g (95 %)을 수득 하였다.
반응식2에 따라,
<반응식2>
10 g (0.021 mol, 1 당량)의 티오에테르를 80 ℃에서 질소하에서 18.26 g (0.62 mol, 3.02 당량) 3-(3,5-di-tert. butyl -4-hydroxyphenyl)propionic acid methyl ester와 마그네틱 교반기, 응축 브리지 및 콜드 트랩을 사용하여 Schlenk 플라스크 내에서 용융시킨다. 0.15 몰 %의 n- Bu2SnO (티오 에테르에 대하여)를 투명한 용융물에 첨가하고, 반응 혼합물을 150 ℃까지 가열하고 ~ 4 시간 동안 ~ 50mbar에서 교반한다. 반응 모니터링은 1H NMR 분석을 통해 수행된다. 전환이 수행 된 후, 진공을 <5 mbar로 증가시키고 나머지 3-(3,5-di-tert. butyl-4-hydroxyphenyl)propionic acid methyl ester를 응축시켰다. 진공을 N2 로 취소하고 반응 혼합물을 RT로 냉각시키고, 용융물을 단단한 유리 같은 덩어리로 응고시켰다. 에스테르 교환 반응 생성물은 톨 루올에 수용되고, 이어서 50 몰 농도 NaHCO3 용액으로 2 회 세척되고, 이어서 증류수를 사용하여 pH 중성까지 2회 세척된다. 유기상을 Na2SO4상에서 건조시키고, 유리 필터 깔때기를 통해 여과하고, 용매를 진공하에 제거 하였다. 19.6g (75 %)의 딱딱한 유리 같은 고형물이 남아있다. 구조는 1H NMR 스펙트럼에 의해 확인되었다.
1 H NMR (300 MHz, CDCl3) δ = 6.91 (s, 6H, -Carom.- H ), 5.00 (s, 3H, -Carom.-O H ), 4.15 (t, 6H, -COOC H 2 -), 3.92 (t, 6H, -N-C H 2 -), 2.79 (t, 6H, -Carom.-C H 2 -), 2.65 (t, 6H, -S-C H 2 -CH2O-), 2.59 - 2.44 (m, 12H, -N-(CH2)2-C H 2 -, O=C-C H 2-), 1.87 (p, 6H, -N-CH2-C H 2 -CH2-), 1.35 (s, 54H, -C H 3 ).
13 C NMR (76 MHz, CDCl3) δ = 173.08, 152.31, 149.09, 136.08, 131.10, 124.91, 63.41, 42.32, 36.50, 34.45, 31.08, 30.47, 29.64, 27.61.
반응식3에 따라,
<반응식3>
5.20g (20.86mmol, 1 당량) triallylisocyanurate 를 교반하면서 격막을 사용하여 50m Schlen 플라스크에서 11.08g (141.85mmol, 6.8 당량) 2-mercaptoethanol 와 용해시키고 균질화한다. 투명한 용액을 N2로 1 시간 동안 탈기시켰다. 격막을 N2 하에서 버블 카운터를 갖는 환류 응축기로 교체하고 용액을 105 ℃로 가열한다. 일단 온도에 도달하면, 16 mg dicumyl peroxide 를 첨가하고 반응 혼합물을 105 ℃에서 8 시간 동안 교반 하였다. 반응 모니터링은 C = C 이중 결합의 감소에 의한 1H NMR 분석을 통해 일어난다. 투명한 용액은 과량의 티올로부터 유리되고 80 ℃에서 진공 (10-2 mbar) 하에서 여과된다. 9.97g의 투명 겔 (이론치의 97 %)이 남아있다.
반응식4에 따라,
<반응식4>
7.65 g (15.82 mmol, 1 당량)의 티오에테르 전구체를 15.51 g (53.04 mol, 3.35 당량)의 3-(3,5-di-tert. butyl -4-hydroxyphenyl)propionic acid methyl ester (Metilox) 와 N2 하에 80 ℃에서 축합 브릿지 및 진공 연결부를 갖는 콜드 트랩을 사용하여 100 ml Schlenk 플라스크에서 용융시키고 균질화한다. 156.83 mg (4.98 mmol, 0.31 당량) DBTO를 N2 하에서 투명한 용융물에 첨가하고 온도를 140 ℃로 올렸다. ~ 200 mbar의 약간의 진공이 적용되고 반응 혼합물이 5 시간 동안 교반된다. 반응 기간 종료 후, 압력을 10-3 mbar로 감소시키고, 온도를 160 ℃로 상승시키고, 과량의 Metilox를 응축시킨다. N2 로 가스 처리 한 후, 투명한 반응 용융물을 RT로 냉각시키고 이어서 디클로로 메탄에 수용한다. 1.4 g의 산 활성화 된 표백 토 (Optimum 210 FF, Clariant)를 교반하면서 첨가하고 현탁액을 30 분 동안 환류시켰다. 여과는 짧은 실리카 패드를 통해 이루어지고 용매는 진공 하에서 제거된다. 16.86g (이론치의 83 %)의 유리 같은 투명한 고체가 남아있다. 구조는 1H NMR 스펙트럼에 의해 확인되었다.
1 H NMR (300 MHz, Chloroform-d) δ = 6.91 (s, 6H, -Carom.-H), 5.00 (s, 3H, -Carom.-OH), 4.15 (t, 6H, -COOCH2-), 3.92 (t, 6H, -N-C H 2 -), 2.79 (t, 6H, -Carom.-C H 2 -), 2.65 (t, 6H, -S-C H 2 -CH2O-), 2.60 - 2.37 (m, 12H, -N-(CH2)2-C H 2 -, O=C-C H 2-), 1.87 (p, 6H, -N-CH2-C H 2 -CH2-), 1.35 (s, 54H, -C H 3 ).
13 C NMR (76 MHz, Chloroform-d) δ = 172.98, 152.20, 148.98, 135.97, 130.99, 124.80, 63.29, 42.20, 36.38, 34.33, 30.95, 30.34, 29.52, 27.49 ppm.
b) 본 발명에 따른 실시예B의 합성 :
<figure 1>
실시 예 A 반응식 1과 유사하게, 5.00g (0.020mol, 1 당량) triallylcyanurate 를 50 분의 노출 시간에서 4.78g (0.061 몰, 3.05 당량) 2-mercaptoethanol 로 전환시켰다. 여과는 60 ℃에서 고진공하에 수행된다. 투명한 담황색 및 중간 점도 겔 9.1 g (이론치의 94 %)을 수득 하였다.
실시 예 A 반응식 2와 유사하게, 4 g (0.080 mol, 1 당량)의 티오에테르를 ~ 100 mbar 에서 7.74 g (0.02 g 몰, 3.25 당량) 3-(3,5 di-tert-butyl-4-hydroxyphenyl) propionic acid methyl ester 로 전환시켜 수성으로 마무리한다. 단단하고 황색을 띠는 투명한 고체가 남는다. 수율은 9.20 g (이론치의 88 %)이다. Figure 1에 따른 구조는 1H NMR 스펙트럼에 의해 확인되었다.
1 H NMR (300 MHz, CDCl3) δ = 6.91 (s, 6H, -Carom.- H ), 5.00 (s, 3H, -Carom.-O H ), 4.14 (t, 6H, -COOC H 2 -), 3.91 (t, 6H, -OC H 2 -), 2.79 (t, 6H, -Carom.-C H 2 -), 2.65 (t, 6H, -S-C H 2 -CH2O-), 2.58 - 2.47 (m, 12H, -S-C H 2 -(CH2)2O-, O=C-C H 2-), 1.87 (p, 6H, -O-CH2-C H 2 -CH2-), 1.35 (s, 54H, -C H 3 ).
13 C NMR (76 MHz, CDCl3) δ = 172.97, 152.20, 135.97, 130.99, 124.80, 63.30, 42.21, 36.39, 34.34, 30.97, 30.36, 29.52, 27.50.
실시 예 A 및 방응식3과 유사하게, triallylcyanurate 5.21 g (20.90 mmol, 1 당량)을 31 시간의 반응 시간 내에 110 ℃에서 7.97 g (102.01 mmol, 4.88 당량) 2-mercaptoethanol 로 전환시켰다. 여과는 100 ℃에서 고진공하에 수행된다. 9.01 g (이론치의 89 %)의 투명 겔이 남아있다.
실시 예 A 반응식 4와 유사하게, 9.00 g (18.61 mmol, 1 당량)의 티오에테르를 22.40 g (76.60 mmol, 4.12 당량) 3-(3,5-di-tert. butyl-4-hydroxyphenyl)propionic acid methylester로 50-200 mbar에서 전환시키고 설명된 것처럼 2.8 g 표백토로 여과 하였다. 유리 같은 투명 고점도 수지의 수율은 14.27 g (이론치의 61 %)에 이른다. figure 1에 따른 구조는 1H NMR 스펙트럼에 의해 확인되었다.
1 H NMR (300 MHz, Chloroform-d) δ = 6.91 (s, 6H, -Carom.- H ), 5.00 (s, 3H, -Carom.-O H ), 4.40 (t, 6H, -Carom.-O-C H 2 - ), 4.16 (t, 6H, -COOC H 2 -), 2.79 (t, 6H-Carom.-C H 2 -), 2.65 (td, 12H, -C H 2 -S-C H 2 ), 2.57 - 2.50 (m, 6H, O=C-C H 2-), 1.99 (p, 6H, -O-CH2-C H 2 -CH2-), 1.35 (s, 54H, -C H 3 ) ppm.
13 C NMR (76 MHz, Chloroform-d) δ = 173.01, 172.98, 152.20, 135.97, 130.98, 124.80, 66.73, 63.33, 36.37, 34.33, 30.96, 30.50, 30.34, 28.64 ppm.
c) 본 발명에 따른 실시 예 C의 합성 :
<Figure 2>
실시 예 A 반응식 1과 유사하게, 7.0 g (0.028 mol, 1 당량) tetraallyloxyethane 을 8.8 g (0.113 mol, 4.1 당량) 2-mercaptoethanol 로 전환시켰다. 노출 시간은 60 분이다. 실시 예 A와 유사하게 수성 마무리 후, 80 ℃에서 고진공하에 여과를 계속하고 용매를 제거한다. 저점도의 투명한 호박색 겔 13.6 g (이론치의 87 %)을 수득 하였다.
실시 예 A 반응식 2와 유사하게, 티오에테르의 3.52 g (0.006 mol, 1 당량)을 7.72 g (0.025 mol, 4.0 당량)의 3-(3,5-di-tert. - butyl-4-hydroxyphenyl)propionic acid methyl ester 로 140 ℃ 및 ~ 80 mbar에서 전환시켰다. 미가공 생성물을 대략 200 ml의 에틸 아세테이트에 용해시키고 실시 예 A와 유사하게 수성으로 마무리 하였다. 고점도의 투명한 호박색 겔 9.25 g (이론치의 92 %)을 수득 하였다. Figure 2에 따른 구조는 1H NMR 스펙트럼에 의해 확인되었다.
1 H NMR (300 MHz, CDCl3) δ = 6.91 (s, 8H, -Carom.- H ), 5.00 (s, 4H, -Carom.-O H ), 4.25 (s, 2H,-C H -C H -), 4.15 (t, 8H, -COOC H 2 -), 3.76 - 3.46 (m, 8H, -CH-O-C H 2), 2.79 (t, 8H, -Carom.-C H 2 -), 2.64 (t, 8H, O=C-C H 2-)2.70 - 2.42 (m, 16H, -C H 2 -S-C H 2 -), 1.79 (p, 8H, -S-CH2-C H 2 -CH2-O-), 1.35 (s, 72H, -C H 3 ).
13 C NMR (76 MHz, CDCl3) δ = 172.97, 152.19, 135.94, 130.99, 124.79, 102.37, 66.01, 63.36, 36.38, 34.33, 30.96, 30.34, 29.84, 28.92.
실시 예 A 반응식3과 유사하게, 5.00 g (19.66 mmol, 1 당량) tetraallyloxyethane 을 7.37 g (94.33 mmol, 4.8 당량) 2-mercaptoethanol 및 216 mg (0.80 mmol, 0.04 당량) dicumyl peroxide 와 함께 100 °에서 2 시간 동안 교반 하였다. 1.34 g (17.15 mmol, 1.15 당량) 2-mercaptoethanol 을 다시 첨가하고 추가로 2.5 시간 동안 교반 하였다. 여과는 100 ℃에서 고진공하에 수행된다. 10.07g (이론치의 90 %)의 투명한 연 황색 겔이 남아있다.
실시 예 A 반응식 4와 유사하게, 8.59 g (15.15 mmol, 1 당량)의 티오에테르를 19.50 g (66.68 mmol, 4.12 당량) 3-(3,5-di-tert. butyl-4-hydroxyphenyl)propionic acid methylester로 50-200 mbar 에서 전환시키고, 설명된 바와 같이 2.8g 표백 토로 여과하였다. 유리 같은 투명하고 담황색 고점도 수지의 수율은 14.27 g (이론치의 61 %)에 이른다. Figure 2에 따른 구조는 1H NMR 스펙트럼에 의해 확인되었다.
1 H NMR (300 MHz, Chloroform-d) δ = 6.91 (s, 8H, -Carom.- H ), 5.00 (s, 4H, -Carom.-O H ), 4.25 (s, 2H,-C H -C H -), 4.15 (t, 8H, -COOC H 2 -), 3.75 - 3.43 (m, 8H, -CH-O-C H 2), 2.80 (t, 8H, -Carom.-C H 2 -), 2.64 (t, 8H, O=C-C H 2-), 2.61 - 2.48 (m, 16H, -C H 2 -S-C H 2 -), 1.79 (p, 8H, -S-CH2-C H 2 -CH2-O-), 1.35 (s, 72H, -C H 3 ) ppm.
13 C NMR (76 MHz, chloroform-d) δ = 172.97, 152.20, 135.95, 131.00, 124.80, 102.38, 66.02, 63.36, 36.38, 34.33, 30.96, 30.35, 29.85, 28.92.
d) 본 발명에 따른 실시 예 D의 합성 :
<Figure 3>
실시 예 A 반응식 1과 유사하게, 5.71 g (0.055 mol, 1 당량) 스티렌을 4.71 g (0.060 몰, 1.1 당량) mercaptoethanol 및 0.2 중량 % phenyl-bis(2,4,6-trimethylbenzoyl)-phosphine oxide (스티렌에 대한 광개시제)로 전환시켰다. 투명한 저점도 원료 생성물은 대략 100 ml 디클로로 메탄에 수용되고 실시 예 A와 유사하게 수성으로 마무리된다. 저점도의 투명한 겔 7.48 g (이론치의 75 %)을 수득 하였다.
실시 예 A 반응식 2와 유사하게, 티오에테르 4.12 g (0.023 mol, 1 당량)을 7.72 g (0.025 mol, 1.1 당량) 3-(3,5-di-tert. - butyl-4-hydroxyphenyl)propionic acid methyl ester로 140 ℃ 및 ~ 800 mbar에서 전환시켰다. 원료 생성물은 대략 150 ml의 톨루올에 수용되고 실시 예 A와 유사하게 수성으로 마무리된다. 고점도의 투명한 황색 겔 9.27g (이론치의 93 %)을 수득 하였다. figure 3에 따른 구조는 1H NMR 스펙트럼에 의해 확인되었다.
1 H NMR (300 MHz, CDCl3) δ = 7.29 - 7.05 (m, 5H, -Carom., Styrol- H ), 6.91 (s, 2H, -Carom., Metilox- H ), 4.99 (s, 1H, -Carom., Metilox-O H ), 4.15 (t, 2H, COOC H 2 -), 2.86 - 2.68 (m, 6H, -C H 2 -S-C H 2 -C H 2 -), 2.65 (t, 2H, Carom., Metilox-C H 2 -), 2.59 - 2.46 (m, 2H, O=C-C H 2-), 1.35 (s, 18H, -C H 3 ).
13 C NMR (76 MHz, CDCl3) δ = 140.23 , 128.63 , 128.54 , 128.50 , 128.35 , 126.49 , 125.85 , 60.30 , 36.37 , 35.50 , 33.22.
e) 본 발명에 따른 실시 예 E의 합성 :
<Figure 4>
실시 예 A 반응식 1과 유사하게, 6.00 g (0.037 mol, 1 당량) trivinylcyclohexane 을 0.2 중량 %의 phenyl-bis(2,4,6-trimethylbenzoyl)-phosphine oxide(트리 비닐 시클로 헥산에 대한 광개시제)와 함께 8.81 g (0.113 mol, 3.05 당량) 2-mercaptoethanol로 전환시켰다. 투명한 중간 점도 및 담황색 원료는 대략 100 ml 디에틸에테르에 수용되고 실시 예 A와 유사하게 수성으로 마무리된다. 80 ℃에서 고진공 하에서 추가로 여과 한 후, 13.8g (이론치의 94 %)의 투명한 담황색 및 중간 점도 겔이 수득되었다.
실시 예 A 반응식 2와 유사하게, 티오에테르 4.00 g (0.010 mol, 1 당량)을 8.99 g (0.031 mol, 3:05 당량) 3-(3,5-di-tert. - butyl-4-hydroxyphenyl)propionic acid methyl ester 로 150 ° C 및 ~ 100 mbar에서 전환시켰다. 여과는 실시 예 A와 유사하게 수성으로 수행된다. 거칠고 황색을 띠는 투명한 수지는 10.21g (이론치의 86 %)의 수율로 남는다. figure 4에 따른 구조는 1H NMR 스펙트럼에 의해 확인되었다.
1 H NMR (300 MHz, CDCl3) δ = 6.91 (s, 6H, Carom.- H ), 5.00 (s, 3H, -Carom.-O H ), 4.15 (t, 6H, -COOC H 2 -), 2.90 - 2.73 (t, 6H, -Carom.-C H 2 ), 2.64 (t, 6H, O=C-C H 2-), 2.60 - 2.31 (m, 12H, -C H 2 -S-C H 2 -), 1.35 (s, 54H, -C H 3 ), 1.99 - 0.38 (m, 15H, -C H 2 -C H Ring, aliph., C H 2 ,Ring, aliph.).
13 C NMR (76 MHz, CDCl3) δ = 173.00, 152.20, 135.97, 131.01, 124.81, 63.45, 40.71, 38.44, 37.07, 36.61, 36.42, 34.35, 33.28, 32.39, 31.00, 30.61, 30.38, 29.91, 29.54.
f) 본 발명에 따른 실시 예 F의 합성 :
<Figure 5>
실시 예 A 반응식 1과 유사하게, 6.12 g (0.025 mol, 1 당량) diallylphthalate 를 4.08 g (0.052 mol, 2.1 당량) 2-mercaptoethanol 및 0.2 중량 %의 phenyl-bis(2,4,6-trimethylbenzoyl)-phosphine oxide (diallylphthalate에 대한 광개시제)로 전환시킨다. 여과는 60 ℃에서 고진공하에 수행된다. 투명한 담황색 및 저점도 겔 9.91g (이론치의 99 %)을 수득 하였다.
실시 예 A 반응식 2와 유사하게, 티오에테르 3.50 g (0.009 mol, 1 당량)을 140°C 및 ~ 800mbar 에서 5.09 g (0.174 mol, 2.0 당량) 3-(3,5-di-tert. - butyl-4-hydroxyphenyl)propionic acid methyl ester 로 전환시켰다. 140 ℃에서 고진공하에 여과가 수행된다.투명한 담황색 및 저점도 겔 7.38g (이론치의 74 %)을 수득 하였다. figure 5에 따른 구조는 1H NMR 스펙트럼에 의해 확인되었다.
1 H NMR (300 MHz, CDCl3) δ = 7.64 (m, 2H,-C-Carom., Phthalat- H ), 7.55 - 7.37 (m, 2H, -Carom., Phthalat- H ), 6.91 (s, 4H, -Carom., Metilox- H ), 5.00 (s, 2H, -Carom.-O H ), 4.44 - 4.28 (m, 4H, -Carom., Phthalat-COOC H 2 -), 4.22 - 4.04 (m, 4H, -CH2COOC H 2 -), 2.79 (t, 6H, -Carom.-C H 2 -), 2.70 - 2.48 (m, 12H), 1.96 (p, 4H, -S-CH2-C H 2 -CH2-), 1.35 (s, 36H, -C H 3 ).
13 C NMR (76 MHz, CDCl3) δ = 172.97 , 167.40 , 152.19 , 135.95 , 131.99 , 131.14 , 130.97 , 128.91 , 124.79 , 64.12 , 63.33 , 62.83 , 36.37 , 34.32 , 30.95 , 30.48 , 30.34 , 28.74 , 28.67.
실시 예 A 반응식 3과 유사하게, 9.18 g (37.28 mmol, 1 당량) diallylphthalate 를 6.99 g (89.47 mmol, 2.4 당량) 2-mercaptoethanol 및 180 mg (1.1 mmol, 0.02 당량) azobis(2-methylpropionitrile)과 반응 온도 70° C 에서 1 시간 동안 교반시켰다. 0.04 g (0.24 mmol, 0.006 당량) 2-2'-azobis(2-methylpropionitrile)을 다시 첨가하고 80 ℃에서 추가 9 시간 동안 혼합한다. 여과는 80 ℃에서 고진공하에 일어난다. 13.68 g (이론치의 91 %)의 투명한 연 황색 저점도 겔이 남아있다.
실시 예 A 반응식 4와 유사하게, 티오 에테르 8.72 g (21.66 mmol, 1 당량)을 50-200 mbar 에서 12.99 g (44.42 mmol, 2.05 당량) 3-(3,5-di-tert. butyl-4-hydroxyphenyl)propionic acid methylester 로 전환시켰고 설명 된 바와 같이, 1.4 g 표백토 여과하였다. 투명하고 연한 황색 고점도 수지의 수율은 8.77 g (이론치의 87 %)에 이른다. figure 5에 따른 구조는 1H NMR 스펙트럼에 의해 확인되었다.
1 H NMR (300 MHz, Chloroform-d) δ = 7.72 - 7.60 (m, 2H, -C-Carom., Phthalat- H ), 7.53 - 7.39 (m, 2H, -Carom., Phthalat- H ), 6.92 (s, 4H, -Carom., Metilox- H ), 5.00 (s, 2H, -Carom.-O H ), 4.35 (t, 4H, -Carom., Phthalat-COOC H 2 -), 3.66 (t, 4H, -CH2COOC H 2 -), 2.80 (t, 4H, Carom.-C H 2 -), 2.64 - 2.49 (m, 8H, -C H 2 -S-C H 2 ), 1.97 (p, 4H, -S-CH2-C H 2 -CH2-), 1.36 (s, 36H, -C H 3 ).
g) 본 발명에 따른 실시 예 G의 합성 :
반응식5에 따르면,
<반응식5>
5.40 g (35.03 mmol, 1 당량) N,N'-methylene-bis-acrylamide 를 12.21 g (156.28 mmol, 4.5 당량) 2-mercaptoethanol 및 370 mg (3.6 mmol, 0.1 당량) Triethylamin과 20 ml 메탄올에서 교반하고 현탁시켰다. 현탁액은 가열될 때 수 분 후에 백색 고체가 침전되면서 균질하고 투명하게 정화된다. 고체를 여과 제거하고, 증류수 15ml 및 메탄올 15ml로 3 회 세척 한 후 건조 캐비닛에서 건조시킨다. 7.40g (이론치의 68 %)의 백색 고체가 남아있다.
<Figure 6>
실시 예 A 반응식 4와 유사하게, 티오 에테르 6.95 g (22.38 mol, 1 당량)을 160°C 및 50-200 mbar에서 8 시간 이내에31.30 g (107.04 mol, 4.8 당량) 3-(3,5-di-tert. - butyl-4-hydroxyphenyl)propionic acid methyl ester로 전환시켰다. 1.4 g 표백토로 설명된대로 여과가 수행된다. 유리 같은 연갈색 고체의 16.72g (이론치의 90 %)이 얻어졌다. figure 6에 따른 구조는 1H NMR 스펙트럼에 의해 확인되었다.
1 H NMR (300 MHz, Chloroform-d) δ = 6.91 (s, 4H, -Carom.- H ), 6.87 (t, 2H, -N H -CH2-N H -), 5.02 (s, 2H, -Carom.-O H ), 4.54 (t, 2H, -NH-C H 2 -NH-), 4.15 (t, 4H, -Carom.-COOC H 2 -), 2.86 - 2.73 (m, 8H, -NH-CO-C H 2 -, -Carom.-CH2-C H 2 -), 2.54 (t, 4H, -Carom.-C H 2 ) 2.39 (t, 4H, Carom.-C H 2 -), 1.35 (s, 36H, -C H 3 ).
13 C NMR (76 MHz, Chloroform-d) δ = 173.06, 172.06, 152.21, 136.01, 130.96, 124.80, 63.37, 44.67, 36.42, 36.37, 34.33, 30.94, 30.74, 30.35, 27.67 ppm.
h) 본 발명에 따른 실시 예 H의 합성 :
<Figure 7>
실시 예 A 반응식 1과 유사하게, 6.64 g (21.53 mol, 1 당량) o,o' diallylbisphenol A 를 0.1 중량 % phenyl-bis(2,4,6-trimethylbenzoyl)-phosphine oxide (diallyl 에 대한 광개시제)와 함께 3.45 g (44.16 mol, 2.05 당량) 2-mercaptoethanol 로 전환시켰다. 여과는 60 ℃에서 고진공하에 수행된다. 투명하고, 황색을 띠며, 점도가 낮은 겔 9.04 g (이론치의 90 %)을 수득 하였다.
실시 예 A 반응식 2와 유사하게, 티오 에테르 3.25g (6.99mol, 2.1 당량)을 145°C 및 50-200 mbar 에서 5 시간 내에 4.29g (14.69 몰, 2.1 당량) 3-(3,5-di-tert. - butyl-4-hydroxyphenyl) propionic acid methyl ester 로 전환시켰다. 여과는 150 ℃에서 고진공하에 수행된다. 투명한 황색을 띠는 고점도 수지 6.07g (이론치의 88 %)을 수득 하였다. figure 7에 따른 구조는 1H NMR 스펙트럼에 의해 확인되었다.
1 H NMR (300 MHz, Chloroform-d) δ = 6.91 (s, 4H, -Carom.-C H ), 6.87 - 6.70 (m, 4H, -C H 2 -CBisphenol-CH 2 ), 6.57 (s, 2H, -CBisphenolOH-C H 2 - ), 5.15 (s, 2H, -CBisphenol-O H ), 5.00 (s, 2H, -Carom.-O H ), 4.14 (t, 4H, -COO-C H 2 -CH2-S-), 2.80 (t, 4H, -Carom.-C H 2 -CH2-COO-), 2.68 - 2.50 (m, 12H), 2.46 (t, 4H, -Carom.-CH2-C H 2 -COO-), 1.80 (p, 4H, , -S-CH2-C H 2 -CH2-), 1.52 (s, 6H, -CBisphenol H 3 ), 1.35 (s, 36H, -C H 3 ).
13 C NMR (76 MHz, Chloroform-d) δ = 173.29, 152.22, 151.57, 143.31, 135.98, 130.97, 128.84, 126.45, 125.64, 114.97, 63.53, 41.66, 36.40, 34.33, 31.69, 30.95, 28.93.
i) 본 발명에 따른 실시 예 I의 합성 :
<Figure 8>
실시 예 A 반응식 3과 유사하게, 5.56 g (19.08 mmol, 1 당량) trimethylallylisocyanurate를 9.63g (123.26 mmol, 6.46 당량) 2-mercaptoethano 및 160 mg (0.60 mmol, 0.03 당량) dicumyl peroxide 와 115 ℃의 반응 온도에서 8시간 동안 교반하였다. 여과는 80 ℃에서 고진공하에 일어난다. 7.14g (이론치의 71 %)의 투명한 연 황색 겔이 남아있다.
실시 예 A 반응식 4와 유사하게, 7.00 g (13.31 mmol, 1 당량)의 티오 에테르를 50-200 mbar 에서 16.24 g (55.54 mmol, 4.12 당량) 3-(3,5-di-tert. butyl-4-hydroxyphenyl)propionic acid methyl ester 로 전환시키고 설명된 바와 같이, 2.8 g 표백토로 여과시킨다. 유리 같은 투명하고 밝은 주황색 유리 형 수지의 수율은 16.29g (이론치의 94 %)에 이른다. figure 8에 따른 구조는 1H NMR 스펙트럼에 의해 확인되었다.
1 H NMR (300 MHz, Chloroform-d) δ = 6.91 (s, 6H, -Carom.-C H ), 5.00 (s, 3H, -Carom.-O H ), 4.12 (t, 6H, -COO-C H 2 -CH2-S-), 3.89 (dd, 3H, -N-CH 2 ´-), 3.73 (dd, 3H, -N-CH 2 ´´-), 2.79 (t, 6H, -Carom.-C H 2 -), 2.63 (t, 6H, -COO-CH2-C H 2 -S-), 2.53 (m, 9H, -Carom.-CH2-C H 2 -, -S-C H 2 ´ -CH-), 2.41 (dd, 3H, -S-C H 2 ´´ -CH-), 2.18 (p, 3H, -N-CH2- C H -), 1.35 (s, 54H, -C H 3 ), 0.95 (d, 9H, -CH-C H 3 ).
j) 본 발명에 따른 중합체 실시 예 J의 합성 :
20.88 g (83.76 mmol, 1 당량) triallylisocyanurate 를 가열 된 100 mL Schlenk 플라스크에서 6.66 g (85.24 mmol, 0.98 당량) 2-mercaptoethanol 에 용해시킨다. 반응 혼합물은 동결-펌프-해동 방법을 사용하여 2 회 탈기된다. phenyl-bis(2,4,6-trimethylbenzoyl)-phosphine oxide (광개시제)의 주걱 팁을 첨가 한 후, 반응 혼합물에 1 시간 동안 파장 366 nm의 UV 광을 조사한다. 이 공정에서, 반 시간 후에 반응 혼합물의 점도의 명백한 증가가 관찰 될 수있다. 이어서, 반응 혼합물을 110 ℃로 가열하고, 0.1 ml, 2,5-dimethyl-2,5-di(tert-butylperoxy)-hexane(라디칼 스타터)을 첨가 하였다. 2 시간의 반응 시간 후, 1 ml의 2,5-dimethyl-2,5-di(tert-butylperoxy)-hexane 을 다시 첨가 하였다. 점성의 담황색 반응 혼합물을 17 시간의 반응 시간 후에 250 ml의 차가운 메탄올에 침전시켰다. 고진공하에 건조시킨 후, 무색의 분말 생성물 3.80 g을 수득 하였다.
중합체 티오 에테르 2.76 g 및 3-(3,5-di-tert. butyl-4-hydroxyphenyl)propionic acid methylester 16.16 g을 100 m Schlenk 플라스크에서 40 ml 클로로포름에 용해시킨다. 용액을 환류에서 100 ℃로 가열하고 100mg의 dibutyl tin oxide 를 첨가 하였다. 반응 혼합물을 실온으로 냉각시키고 26 시간 후에 300 ml의 차가운 메탄올로 진탕시켰다. 침전 된 생성물을 여과 제거하고, 메탄올로 세척 한 후, 고진공하에 건조시켰다. 백색의 분말 생성물 2.02 g을 수득하였다. 중합체 화합물은 FTIR 스펙트럼에 의해 확인되었다.
IR: 3521 v(-OH), 2953 v(-CH2), 1670 v(-CEster=O), 1155 v (para subst. aromat), 1450 v(-C-N), 931 v(=CH), 762 v(-C-S-), 697 v(=C-H mono-subst. benzol) cm-1.
III. 본 발명에 따른 실시 예의 적용 시험
a) 본 발명에 따른 실시 예 A의 적용 시험
본 발명에 따른 실시 예 A는 황을 함유하는 상업적인 페놀 계 산화 방지제 (비교 예 2, Songnox 1035, Songwon)와 비교하여 표 1로부터 볼 수 있는 중량퍼센트에서 폴리 프로필렌 (Moplen HP 500N, Lyondell Basell Industries)으로 작업되었다. 본 발명에 따른 실시 예 1은 비교예에 대한 비교 가능한 중량 농도를 나타내고; 본 발명에 따른 실시 예 2는 페놀 계 산화 방지계 군에서의 몰 당량에 따라 계산되었다.
표 1 : 본 발명에 따른 실시 예 및 비교 예의 조성물
비교예1 | 첨가제 없이 |
비교예 2 | 0.3 % Songnox 1035 |
비교예 3 | 0.1% Irganox 1010 / 0.2 % DSTDP |
비교예 4 | 0.1% Irganox 1076 / 0.2 % DLTDP |
본 발명에 따른 실시예 1 | 0.3% 실시예A |
본 발명에 따른 실시예 2 | 0.39 % 실시예A |
다음 구조는 Songnox 1035에 의해 이해된다: 2,2'-thiodiethylene bis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate]
DSTDP: Distearylthiodipropionate
DLDTP: Dilauryldithiopropionate
화합물 혼합물의 압출은 표 2에 도시 된 온도 프로파일 하에서 유형 프로세스 11(Fisher Scientific)의 이축 압출기에서 수행되었다. 중합체 용융물은 200 r.p.m에서 방출되고 수조에서 냉각되고 이어서 펠렛화된다.
표2 압출시험의 온도 프로파일
펠렛을 DIN EN ISO 4577.1999에 따라 80 일 동안 150 ℃ 및 50 % 공기 순환에서 대류로에서 에이징시키고 샘플을 5, 10 및 50 일 후에 채취 하였다. 잔류 안정성의 평가는 후속 적으로 퍼지 가스로서 합성 공기를 사용하여 230 ℃ 또는 230 ℃에서 DIN EN ISO 11357-6 : 2013에 따른 정적 OIT (oxidative induction time) 측정에 의해 수행되었다. 표 3은 결정된 유도 시간을 포함한다. 중합체의 잔류 안정성은 여기서 더 높을수록 유도 시간이 길어진다.
표 3 : 150 ° C에서 에이징 후 OIT 값
에이징 후 OIT [min] | ||||
230 °C | 210 °C | |||
0 days | 5 days | 10 days | 50 days | |
비교예 1 | 3 | 0 | 0 | 0 |
비교예 2 | 45 | 21 | 17 | 37 |
비교예 3 | 22 | 11 | 9 | 51 |
비교예 4 | 9 | # | 6 | 17 |
본 발명에 따른 실시예 1 | 62 | 28 | 17 | 82 |
본 발명에 따른 실시예 2 | 88 | 37 | 25 | 119 |
불안정한 폴리 프로필렌 (비교 예 1)에서, 산화의 시작은 매우 짧은 시간에 일어난다; 에이징 후 잔류 안정성은 전혀 없다. 혼합 된 산화방지제를 함유 한 화합물은 산화 시작을 지연시켰다. 본 발명에 따른 실시 예는 놀랍게도 비교 예와 관련하여 본 발명에 따른 안정화제의 우수한 안정성을 보여준다.
에이징 된 샘플 및 에이징되지 않은 샘플의 황색도 지수 (백색 표준, BYK 첨가제 및 기구를 갖는 스펙트로-가이드 구형 광택)의 측정은 표 4에 따라 에이징 과정 동안 비교 예와 대조적으로 본 발명에 따른 실시 예의 훨씬 더 작은 변색 경향을 나타냈다.
표 4 : 150 °C에서 에이징 후 황색도 지수
에이징 후 황색도 지수 증가 | |||
5 days | 10 days | 80 days | |
비교예 1 | 11.6 | 86.4 | 저하 |
비교예 2 | 8.6 | 16.2 | 82.91 |
본 발명에 따른 실시예 1 | 1.3 | 8.7 | 33.57 |
본 발명에 따른 실시예 2 | 2.2 | 11.6 | 42.05 |
b) 본 발명에 따른 실시 예 C의 적용 시험
에이징 된 펠릿의 용융 부피 유량은 DIN EN ISO 1133-2 : 2011 (2.16 kg, 230 ℃)에 따라 결정되었다.
표 5 : 본 발명에 따른 실시 예 및 비교 예의 조성
비교예 1 | 첨가제 없이 |
비교예 2 | 0.3 % Songnox 1035 |
비교예 4 | 0.1% Irganox 1076 / 0.2 % DLTDP |
본 발명에 따른 실시예 3 | 0.3% 실시예C |
표 6은 측정 된 용융 부피 유량을 포함한다. 중합체의 잔류 안정성은 여기서 높을수록 용융 부피 유량은 낮아진다.
표 6 : 150 ° C에서 에이징 후 용융 부피 유량
에이징 후 MVR [cm3 / 10 min ] | ||||
30 days | 60 days | 70 days | 80 days | |
비교예 1 | 측정불가 | 측정 불가 |
측정 불가 |
측정 불가 |
비교예 2 | 18.7 | 25.4 | 측정불가 | 측정 불가 |
비교예 4 | 19.4 | 20.9 | 22.7 | 측정불가 |
본 발명에 따른 실시예 3 | 17.9 | 19.4 | 21.3 | 22.7 |
불안정한 폴리 프로필렌 (비교 예 1)에서, 폴리 프로필렌의 사슬 분해는 매우 짧은 시간에 일어난다; 에이징 후 잔류 안정성은 전혀 없다. 이에 의해, 측정 된 MVR 값은 더 높은 분해 및 따라서 매우 높은 MVR 값 (> 500)에 도달하기 때문에 더 이상 측정 될 수 없다. 혼합 된 산화방지제를 함유한 화합물은 사슬 분해의 시작을 지연시켰다. 본 발명에 따른 예는 놀랍게도 비교 예에 대하여 에이징 과정에서 본 발명에 따른 안정화제의 우수한 안정성을 보여준다.
c) 활석으로 충전 된 폴리 프로필렌에서의 본 발명에 따른 실시 예의 적용 시험
본 발명에 따른 실시 예 A의 적용 시험과 유사하게, 안정성 평가는 에이징없이 230 ℃에서 충전제로서 활석을 첨가 한 본 발명에 따른 실시 예 및 표 7의 비교 예에 대한 OIT 측정에 의해 수행되었다. 여기서 혼합 된 안정 화제의 함량 백분율은 폴리 프로필렌의 함량과 관련이있다.
표 7 : 본 발명에 따른 실시 예의 및 Finntalc M15로 충전 된 폴리 프로필렌에서의 비교 예 조성 (모든 수치는 중량 %).
비교예 5 | 첨가제 없음 | 20 % Finntalc M15 |
비교예 6 | 0.1 % Irganox 1076 / 0.2 % DLTDP | 20 % Finntalc M15 |
본 발명에 따른 실시예 4 | 0.3% 실시예 A | 20 % Finntalc M15 |
본 발명에 따른 실시예 5 | 0.3% 실시예 C | 20 % Finntalc M15 |
본 발명에 따른 실시예 6 | 0.3% 실시예 F | 20 % Finntalc M15 |
본 발명에 따른 실시예 7 | 0.3% 실시예 G | 20 % Finntalc M15 |
표 8 : 230 ℃에서 에이징하기 전에 20 중량 % Finntalc M15를 갖는 PP의 OIT 값
OIT [min] | |
230 °C | |
비교예 5 | 0 |
비교예 6 | 11 |
본 발명에 따른 실시예 4 | 47 |
본 발명에 따른 실시예 5 | 14 |
본 발명에 따른 실시예 6 | 17 |
본 발명에 따른 실시예 7 | 29 |
Finntalc M15 필러와 함께 안정화되지 않은 폴리 프로필렌 (비교 예 5)에서, 산화의 시작은 불활성 대기에서 산소 함유 대기로 전환 한 직후에 이미 일어나서 더 이상 잔류 안정성이 전혀 없다. 본 발명에 따른 실시 예는 놀랍게도 비교예에 대하여 본 발명에 따른 안정화제의 훨씬 우수한 안정성을 보여준다.
본 발명에 따른 안정화제는 표 9에 따라 유형 Luzenac 1445의 10 % 활석으로 유사하게 작업되었고 OIT가 결정되었다 (표 10).
표 9 본 발명에 따른 실시 예 및 Luzenac 1445 로 충전 된 폴리 프로필렌에서의 비교예의 조성 (모든 수치는 중량 %).
비교예7 | 첨가제 없음 | 10 % Luzenac 1445 |
비교예 8 | 0.1 % Irganox 1076 / 0.2 % DLTDP | 10 % Luzenac 1445 |
본 발명에 따른 실시예 8 | 0.3% 실시예A | 10 % Luzenac 1445 |
본 발명에 따른 실시예 9 | 0.2 % 실시예A | 10 % Luzenac 1445 |
본 발명에 따른 실시예 10 | 0.3% 실시예B | 10 % Luzenac 1445 |
본 발명에 따른 실시예 11 | 0.3% 실시예C | 10 % Luzenac 1445 |
본 발명에 따른 실시예 12 | 0.1 % 실시예C | 10 % Luzenac 1445 |
본 발명에 따른 실시예 13 | 0.3% 실시예F | 10 % Luzenac 1445 |
본 발명에 따른 실시예 14 | 0.1 % 실시예F | 10 % Luzenac 1445 |
본 발명에 따른 실시예 15 | 0.3% 실시예G | 10 % Luzenac 1445 |
본 발명에 따른 실시예 16 | 0.3% 실시예I | 10 % Luzenac 1445 |
표 10 : 에이징 전에 10 중량 %의 Luzenac 1445를 갖는 PP의 OIT 값.
에이징 전 OIT [min] | |
230 °C | |
비교예7 | 5 |
비교예8 | 8 |
본 발명에 따른 실시예 8 | 85 |
본 발명에 따른 실시예 9 | 62 |
본 발명에 따른 실시예 10 | 60 |
본 발명에 따른 실시예 11 | 35 |
본 발명에 따른 실시예 12 | 12 |
본 발명에 따른 실시예 13 | 46 |
본 발명에 따른 실시예 14 | 12 |
본 발명에 따른 실시예 15 | 43 |
본 발명에 따른 실시예 16 | 41 |
Luzenac 1445 필러를 사용한 불안정한 폴리 프로필렌 (비교 예 7)에서, 산화의 시작은 이미 매우 일찍 시작되었다. 본 발명에 따른 실시 예는 비교 예에 대하여 심지어 비교적 낮은 농도에서도 (본 발명에 따른 실시예 9, 12 및 14) 본 발명에 따른 안정화제의 훨씬 우수한 안정성을 나타낸다.
d) 추가 시스템에서 본 발명에 따른 실시 예의 적용 시험
본 발명에 따른 화합물 A는 또한 0.3 %의 농도로하기 중합체에 작용 하였다.
D1: ABS (Acrylonitrile butadinee styrene)
D2: Polyamide-6
D3: Polyamide-6 with 30% glass fibers유리섬유 30%인 폴리아미드-6
D4: Polybutylene terephthalate
모든 경우에, 개선 된 장기 안정성, 즉 기계적 특성의 유지는 첨가제가없는 중합체에 대해 입증 될 수있다.
Claims (17)
- 제 1 항에있어서,
상기 변수 A는 각각의 z가 시아 누르산 잔기, 여기서 z는 제 1 항에 제공된 의미를 가지며; 트리아진 잔기; 5 내지 36 개의 탄소 원자를 갖는시 클릭 지방족 탄화수소 잔기, 특히 시클로 헥실; 방향족 탄화수소 잔기, 특히 페닐; 및 2 내지 36 개의 탄소 원자를 갖는 선형 또는 분 지형 지방족 탄화수소 잔기를 포함하는 군으로부터 선택되는 것을 특징으로 하는 화합물.
- 제 1 항 내지 제 3 항 중 어느 한 항에 있어서,
변수 x, y 및 z는 각각 서로 독립적으로하기 의미를 갖는 것을 특징으로하는 화합물:
X: 0 또는 1;
Y: 1 또는 2; 및
z: 1, 2, 3 또는 4.
- 제 1 항 내지 제 5 항 중 어느 한 항에 있어서,
D는 -CH2- 또는 1,2,3- 프로피닐 잔기를 포함하는 군에서 선택되는 것을 특징으로하는 화합물.
- 제 1 항 내지 제 7 항 중 어느 한 항에 따른 화학식 I 에 따른 화합물의 제조방법에 있어서,
화학식 II에 따른 화합물이
<화학식 II>
화학식 IIIa 또는 IIIb 중 하나에 따른 티올과 반응하고, 및
<화학식 IIIa> <화학식 IIIb>
화학식 IIIa의 티올이 사용 된 경우, 이어서, 화학식 II 및 IIIa의 화합물의 반응에 의해 획득된 반응 생성물이 화학식 IV의 화합물과 반응하는 방법.
<화학식 IV>
여기서X는 이탈 기; 및
변수 A, B, D, R, b, x, y 및 z의 의미는 제 1 항에 나타낸 화학식 IIa, IIb 및 III의 화합물에서 정의된 바와 같다.
- 제 8 항에 있어서,
상기 X는 알콜레이트, 할라이드, 트리플루오로메탄 설포네이트, 토실레이트, 메실레이트, 플루오로설포네이트, 또는 노나플레이트 인 것을 특징으로하는 방법.
- 제 8 항 또는 제 9 항에있어서,
화학식 IIIa 또는 IIIb 중 하나에 따른 티올과 화학식 III에 따른 화합물의 반응이 화학식 II에 따른 화합물의 불포화 작용과 관련하여 과량의 티올로 수행되는 것을 특징으로하는 방법.
- 안정화될 하나 이상의 유기 성분; 및 제 1 항 내지 제 7 항 중 어느 한 항에 따른 하나 이상의 화합물;을 포함하거나 이로 이루어진 조성물.
- 제 11 항에있어서, 안정화 될 성분은 플라스틱, 오일, 윤활제 및 지방을 포함하는 군에서 선택되는 것을 특징으로하는 조성물.
- 제 11 항 또는 제12항에 있어서,
안정화 될 하나 이상의 성분 95.00 내지 99.99 중량 %, 바람직하게는 97.00 내지 99.95 중량 %, 특히 바람직하게는 98.00 내지 99.90 중량 %; 및
제 1 항 내지 제 7 항 중 어느 한 항에 따른 하나 이상의 화합물 0.01 내지 5.00 중량 %, 바람직하게는 0.05 내지 3.00 중량 %, 특히 바람직하게는 0.10 내지 2.00 중량 %;를 포함하거나 이로 이루어진 조성물.
- 제 11 항 내지 제 13 항 중 어느 한 항에 있어서,
추가로 적어도 하나의 첨가제는 UV 흡수제, 광 안정 화제, 안정 화제, 산화 방지제, 히드록실아민, 벤조푸란, 금속 불활성화제, 충전제 불활성화제, 오존분해방지제(antiozonant), 핵형성제, 충격 강도 개선제, 가소제, 윤활제, 레올로지 개질제, 요 변제(thixotropic agent), 사슬 연장 제, 가공 보조제, 탈형 보조제, 난연제, 안료, 염료, 형광 증백제(optical brightener), 항균제, 대전 방지제, 슬립제, 블로킹방지제(antiblocking agent), 커플링제, 가교제, 가교방지제, 친수화제, 소수성 화제, 결합제, 분산제, 분해 첨가제, 소포 보조제, 냄새 트랩(odor traps), 마킹 제, 김서림 방지제, 충전제 및 강화제를 포함하는 군으로부터 선택되는 조성물.
- 제 11 항 내지 제 14 항 중 어느 한 항에 있어서,
포스파이트, 포스포니트, 히드록시라민 또는 니트론을 포함하는 군으로부터 선택된 하나 이상의 첨가제가 추가로 포함되는 것을 특징으로하는 조성물.
- 안정화될 유기성분의 안정화 방법에 있어서,
특히 산화적, 열적 또는 광화학선 분해 또는 손상과 관련하여, 제 1 항 내지 제 7 항 중 어느 한 항에 따른 하나 이상의 화합물이 안정화 될 유기 성분과 혼합되거나 또는 그 안에서 가공되는 방법.
- 산화적, 열적 또는 광화학선 분해 또는 손상과 관련하여 유기 물질을 안정화시키기위한 제 1 항 내지 제 7 항 중 어느 한 항에 따른 화합물의 용도.
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DE102017220555.5 | 2017-11-17 | ||
PCT/EP2018/081270 WO2019096868A1 (de) | 2017-11-17 | 2018-11-14 | Verbindungen mit stabilisierender wirkung, verfahren zu deren herstellung, zusammensetzung enthaltend diese stabilisierenden verbindungen, verfahren zur stabilisierung einer organischen komponente sowie verwendung von stabilisierenden verbindungen |
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DE102017217312A1 (de) | 2017-09-28 | 2019-03-28 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verfahren zur Stabilisierung von halogenfreien thermoplastischen Kunststoff-Rezyklaten sowie stabilisierte Kunststoffzusammensetzungen und hieraus hergestellte Formmassen und Formteile |
DE102017220555A1 (de) | 2017-11-17 | 2019-05-23 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verbindungen mit stabilisierender Wirkung, Verfahren zu deren Herstellung, Zusammensetzung enthaltend diese stabilisierenden Verbindungen, Verfahren zur Stabilisierung einer organischen Komponente sowie Verwendung von stabilisierenden Verbindungen |
DE102020128803A1 (de) | 2020-11-02 | 2022-05-05 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein | Verwendung von Eugenol-Derivaten als Stabilisatoren, organisches Material sowie Eugenol-Derivate |
CN114805260B (zh) * | 2022-04-20 | 2023-04-25 | 四川大学 | 一种长碳链生物基聚氨酯用二元伯醇的制备方法 |
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US11407720B2 (en) | 2022-08-09 |
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US20200361879A1 (en) | 2020-11-19 |
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