KR950032242A - Monomeric and oligomeric bisphenyl-HALS phosphites, compositions comprising them and their use as stabilizers - Google Patents

Monomeric and oligomeric bisphenyl-HALS phosphites, compositions comprising them and their use as stabilizers Download PDF

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KR950032242A
KR950032242A KR1019950008880A KR19950008880A KR950032242A KR 950032242 A KR950032242 A KR 950032242A KR 1019950008880 A KR1019950008880 A KR 1019950008880A KR 19950008880 A KR19950008880 A KR 19950008880A KR 950032242 A KR950032242 A KR 950032242A
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피텔로우드 리타
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베르너 발데크
시바-가이기 아게
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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
    • C08K5/49—Phosphorus-containing compounds
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    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
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    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/04—Homopolymers or copolymers of ethene
    • C08L23/06—Polyethene
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    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/10—Homopolymers or copolymers of propene
    • C08L23/12—Polypropene

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Abstract

산화적, 열적 또는 광 유도 분해로 부터 유기물질을 안정화시키기 위한 안정화제인 일반식(I)의 단량체화합물 및 일반식(II)의 올리고머성 화합물이 기재되어 있다:Monomeric compounds of formula (I) and oligomeric compounds of formula (II) are described which are stabilizers for stabilizing organic substances from oxidative, thermal or photoinduced decomposition:

식중에서, R1및 R2는 서로 독립해서 수소, C1-C25알킬, C2-C24알켄일, 비치환 또는 C1-C4알킬-치환된C5-C8시클로알킬; 비치환 또는C1-C4알킬-치환된 페닐; 비치환 또는 C1-C4알킬-치환된C5-C8시클로알켄일;또는 C7-C9페닐알킬이고, R3은 수소 또는 메틸이며, R4는 수소, C1-C8알킬, O, OH, NO, -CH2CN, C1-C18알콕시, C5-C12시클로알콕시, C3-C6알켄일, C3-C6알킨일, C1-C8아실 또는 비치환되거나 또는 페닐고리에서 C1-C4알킬에 의해 치환된 C7-C9페닐알킬이거나; 또는 R5및 R6은 서로 독립해서 수소, CF3, C1-C12알킬 또는 페닐이거나, 또는 R5및 R6은 이들이 연결된 탄소원자와 합쳐져서 비치환 또는 C1-C4알킬-치환된 C5-C12시클로알킬리덴 고리를 형성하며, 단 R5및 R6이 동시에 수소이면, R4는 수소가 아니며: 및 단 R1, R2및 R3이 동시에 수소이고 또 R5및 R6이 동시에 메틸이면, R4는 수소가 아니며, R7은 수소, C1-C8알킬 또는 하기 일반식(III)Wherein R 1 and R 2 independently of one another are hydrogen, C 1 -C 25 alkyl, C 2 -C 24 alkenyl, unsubstituted or C 1 -C 4 alkyl-substituted C 5 -C 8 cycloalkyl; Unsubstituted or C 1 -C 4 alkyl-substituted phenyl; Unsubstituted or C 1 -C 4 alkyl-substituted C 5 -C 8 cycloalkenyl; or C 7 -C 9 phenylalkyl, R 3 is hydrogen or methyl, R 4 is hydrogen, C 1 -C 8 alkyl , O, OH, NO, -CH 2 CN, C 1 -C 18 alkoxy, C 5 -C 12 cycloalkoxy, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1 -C 8 acyl or C 7 -C 9 phenylalkyl unsubstituted or substituted by C 1 -C 4 alkyl in the phenyl ring; Or R 5 and R 6 independently of one another are hydrogen, CF 3 , C 1 -C 12 alkyl or phenyl, or R 5 and R 6 are combined with the carbon atom to which they are attached to thereby be unsubstituted or C 1 -C 4 alkyl-substituted Forms a C 5 -C 12 cycloalkylidene ring, provided that if R 5 and R 6 are simultaneously hydrogen, then R 4 is not hydrogen: and provided that R 1 , R 2 and R 3 are simultaneously hydrogen and R 5 and R If 6 is methyl at the same time then R 4 is not hydrogen and R 7 is hydrogen, C 1 -C 8 alkyl or the following general formula (III)

의 기이며, R8은 수소 또는 C1-C8알킬이며, A는 산소, 황,또는이고, X는 산소 또는 N-R7이며, Y 및 Z는 서로 독립해서 C2-C18알킬렌, 중간에 산소, 황 또는를 포함하는 C4-C18알킬렌; C4-C8알켄일렌 또는 페닐에틸렌이며, m은 2 내지 8의 정수이고, 또 n은 2 내지 25의 수임.R 8 is hydrogen or C 1 -C 8 alkyl, A is oxygen, sulfur, or X is oxygen or NR 7 , and Y and Z are independently of each other C 2 -C 18 alkylene, intermediate oxygen, sulfur or C 4 -C 18 alkylene comprising a; C 4 -C 8 alkenylene or phenylethylene, m is an integer from 2 to 8 and n is a number from 2 to 25.

Description

단량체성 및 올리고머성 비스페닐-HALS포스파이트, 이들을 함유하는 조성물 및 안정화재로서의 이들의 용도Monomeric and oligomeric bisphenyl-HALS phosphites, compositions containing them and their use as stabilizers

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음As this is a public information case, the full text was not included.

Claims (18)

하기 일반식(I)의 단량체성 화합물 또는 일반식(II)의 올리고머성 화합물:Monomer compound of formula (I) or oligomeric compound of formula (II) 식중에서, R1및 R2는 서로 독립해서 수소, C1-C25알킬, C2-C24알켄일, 비치환 또는 C1-C4알킬-치환된C5-C8시클로알킬; 비치환 또는C1-C4알킬-치환된 페닐; 비치환 또는 C1-C4알킬-치횐된C5-C8시클로알켄일;또는 C7-C|9페닐알킬이고, R3은 수소 또는 메틸이며, R4는 수소, C1-C8알킬, O, OH, NO, -CH2CN, C1-C18알콕시, C5-C12시클로알콕시, C3-C6알켄일, C3-C6알킨일, C1-C8아실 또는 비치환되거나 또는 페닐고리에서 C1-C4알킬에 의해 치환된 C7-C9페닐알킬이거나; 또는 R5및 R6은 서로 독립해서 수소, CF3, C1-C12알킬 또는 페닐이거나, 또는 R5및 R6은 이들이 연결된 탄소원자와 합쳐져서 비치환 또는 C1-C4알킬-치환된 C5-C12시클로알킬리덴 고리를 형성하며, 단 R5및 R6이 동시에 수소이면, R4는 수소가 아니며: 및 단 R1, R2및 R3이 동시에 수소이고 또 R5및 R6이 동시에 메틸이면, R4는 수소가 아니며, R7은 수소, C1-C8알킬 또는 하기 일반식(III)Wherein R 1 and R 2 independently of one another are hydrogen, C 1 -C 25 alkyl, C 2 -C 24 alkenyl, unsubstituted or C 1 -C 4 alkyl-substituted C 5 -C 8 cycloalkyl; Unsubstituted or C 1 -C 4 alkyl-substituted phenyl; Unsubstituted or C 1 -C 4 alkyl-substituted C 5 -C 8 cycloalkenyl; or C 7 -C | 9 phenylalkyl, R 3 is hydrogen or methyl, R 4 is hydrogen, C 1 -C 8 alkyl, O, OH, NO, —CH 2 CN, C 1 -C 18 alkoxy, C 5 -C 12 cycloalkoxy , C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1 -C 8 acyl or C 7 -C 9 phenylalkyl unsubstituted or substituted by C 1 -C 4 alkyl in the phenyl ring; Or R 5 and R 6 independently of one another are hydrogen, CF 3 , C 1 -C 12 alkyl or phenyl, or R 5 and R 6 are combined with the carbon atom to which they are attached to thereby be unsubstituted or C 1 -C 4 alkyl-substituted Forms a C 5 -C 12 cycloalkylidene ring, provided that if R 5 and R 6 are simultaneously hydrogen, then R 4 is not hydrogen: and provided that R 1 , R 2 and R 3 are simultaneously hydrogen and R 5 and R If 6 is methyl at the same time then R 4 is not hydrogen and R 7 is hydrogen, C 1 -C 8 alkyl or the following general formula (III) 의 기이며, R8은 수소 또는 C1-C8알킬이며, A는 산소, 황,또는이고, X는 산소 또는 N-R7이며, Y 및 Z는 서로 독립해서 C2-C18알킬렌, 중간에 산소, 황 또는를 포함하는 C4-C18알킬렌; C4-C8알켄일렌 또는 페닐에틸렌이며, m은 2 내지 8의 정수이고, 또 n은 2 내지 25의 수임.R 8 is hydrogen or C 1 -C 8 alkyl, A is oxygen, sulfur, or X is oxygen or NR 7 , and Y and Z are independently of each other C 2 -C 18 alkylene, intermediate oxygen, sulfur or C 4 -C 18 alkylene comprising a; C 4 -C 8 alkenylene or phenylethylene, m is an integer from 2 to 8 and n is a number from 2 to 25. 제1항에 있어서, R1및 R2는 서로 독립해서 수소, C1-C18알킬, C2-C18알켄일, C5-C8시클로알킬, 비치환 또는C1-C4알킬-치환된 페닐; C5-C8시클로알켄일 또는 C7-C9페닐알킬이고, R4는 수소, C1-C4알킬, OH, -CH2CN, C|4-C18알콕시, C5-C12시클로알콕시, 알릴, 프로파르길, 아세틸 또는 C7-C9페닐알킬이고, R5및 R6은 서로 독립해서 수소, CF3, C1-C8알킬 또는 페닐이거나, 또는 R5및 R6은 이들이 연결된 탄소원자와 합쳐져서 C5-C8시클로알킬리덴 고리를 형성하며, R7은 수소 또는 C1-C8알킬이고, R8은 수소 또는 C1-C8알킬이며 A는 산소,또는이고, X는 산소 또는이며, Y 및 Z는 서로 독립해서 C2-C12알킬렌, 중간에 산소 또는를 포함하는 C4-C12알킬렌; C4-C8알켄일렌 또는 페닐에틸렌이며, m은 2 내지 6의 정수이고, 또 n은 2 내지 15의 수인 일반식(I)의 단량체성 화합물 및 일반식(II)이 올리고머성 화합물.The compound of claim 1, wherein R 1 and R 2 independently of one another are hydrogen, C 1 -C 18 alkyl, C 2 -C 18 alkenyl, C 5 -C 8 cycloalkyl, unsubstituted or C 1 -C 4 alkyl- Substituted phenyl; C 5 -C 8 cycloalkenyl or C 7 -C 9 phenylalkyl, R 4 is hydrogen, C 1 -C 4 alkyl, OH, —CH 2 CN, C | 4 -C 18 alkoxy, C 5 -C 12 cycloalkoxy, allyl, propargyl, acetyl or C 7 -C 9 phenylalkyl, R 5 and R 6 are independently of each other hydrogen, CF 3 , C 1 -C 8 Alkyl or phenyl, or R 5 and R 6 combine with the carbon atoms to which they are linked to form a C 5 -C 8 cycloalkylidene ring, R 7 is hydrogen or C 1 -C 8 alkyl, and R 8 is hydrogen or C 1 -C 8 alkyl and A is oxygen, or X is oxygen or And Y and Z are independently of each other C 2 -C 12 alkylene, with oxygen or C 4 -C 12 alkylene comprising a; A monomeric compound of formula (I) and a formula (II) are oligomeric compounds wherein C 4 -C 8 alkenylene or phenylethylene, m is an integer from 2 to 6, and n is a number from 2 to 15. 제1항에 있어서, R1, 및 R2가 서로 독립해서 수소, C1-C8알킬, 시클로헥실 또는 페닐인 일반식(I)의 단량체성 화합물 및 일반식(II)의 올리고머성 화합물.The monomeric compound of formula (I) and the oligomeric compound of formula (II) according to claim 1 , wherein R 1 and R 2 independently of each other are hydrogen, C 1 -C 8 alkyl, cyclohexyl or phenyl. 제1항에 있어서, R4가 수소, C1-C4알킬, C4-C16알콕시, C5-C8시클로알콕시, 알릴, 프로파르길, 아세틸 또는 벤질인 일반식(I)의 단량체성 화합물 및 일반식(II)의 올리고머성 화합물.The monomer of formula (I) according to claim 1, wherein R 4 is hydrogen, C 1 -C 4 alkyl, C 4 -C 16 alkoxy, C 5 -C 8 cycloalkoxy, allyl, propargyl, acetyl or benzyl Sex compounds and oligomeric compounds of formula (II). 제1항에 있어서, R1및 R2가 서로 독립해서 수소, C1-C18알킬, C2-C18알켄일, C5-C8시클로알킬, 페닐 또는 벤질이고, R4는 수소, C1-C4알킬, C4-C16알콕시, C5-C8시클로알콕시, 알릴, 프로파르길, 아세틸 또는 벤질이며, R5및 R6은 이들이 연결된 탄소원자와 합쳐져서 C5-C8시클로알킬리덴 고리를 형성하며, R7은 수소 또는 C1-C4알킬이며, A는또는이고 X는 소 또는이며, Y 및 Z는 서로 독립해서 C2-C8알킬렌, 중간에 산소를 포함하는 C4-C12알킬렌 또는 C4-C8알켄일렌이며 ,m은 2 내지 6의 정수이고, 또 n은 2 내지 10의 수인 일반식(I)의 단량체성 화합물 및 일반식(II)의 올리고머성 화합물.The compound of claim 1, wherein R 1 and R 2 independently of one another are hydrogen, C 1 -C 18 alkyl, C 2 -C 18 alkenyl, C 5 -C 8 cycloalkyl, phenyl or benzyl, and R 4 is hydrogen, C 1 -C 4 alkyl, C 4 -C 16 alkoxy, C 5 -C 8 cycloalkoxy, allyl, propargyl, acetyl or benzyl, R 5 and R 6 are combined with the carbon atom to which they are linked to C 5 -C 8 Forms a cycloalkylidene ring, R 7 is hydrogen or C 1 -C 4 alkyl, and A is or And X is cow or Y and Z are independently of each other C 2 -C 8 alkylene, C 4 -C 12 alkylene or C 4 -C 8 alkenylene containing oxygen in the middle, m is an integer from 2 to 6, and n is a monomeric compound of formula (I) and an oligomeric compound of formula (II) wherein the number is from 2 to 10. 제1항에 있어서, R1및 R2가 서로 독립해서 수소, C1-C8알킬, 시클로헥실 또는 페닐 또는 벤질이고, R4는 수소, C1-C4알킬, C6-C12알콕시, 아세틸 또는 벤질이며, R5및 R6은 서로 독립해서 수소, C1-C8알킬이거나 또는 R5및 R6은 이들이 연결된 탄소원자와 합쳐져서 C5-C8시클로알킬리덴 고리를 형성하며, A는또는이고 X는 산소이며, Y는 C2-C8알킬렌 또는 중간에 산소를 포함하는 C4-C12알킬렌이며, 또 n은 2 내지 10의 수인 일반식(I)의 단량체성 화합물 및 일반식(II)의 올리고머성 화합물.The compound of claim 1, wherein R 1 and R 2 are independently of each other hydrogen, C 1 -C 8 alkyl, cyclohexyl or phenyl or benzyl, and R 4 is hydrogen, C 1 -C 4 alkyl, C 6 -C 12 alkoxy , Acetyl or benzyl, R 5 and R 6 independently of one another are hydrogen, C 1 -C 8 alkyl or R 5 and R 6 combine with the carbon atom to which they are linked to form a C 5 -C 8 cycloalkylidene ring, A is or And X is oxygen, Y is C 2 -C 8 alkylene or C 4 -C 12 alkylene with oxygen in the middle, and n is a monomeric compound of formula (I) and a general Oligomeric Compounds of Formula (II). 제1항에 있어서, R1이 수소이고, R2가 수소, C1-C4알킬 또는 시클로헥실이며, R3은 수소이고, R4는 수소 또는 C1-C4알킬이며, R5및 R6은 서로 독립해서 수소 또는 C1-C4알킬이거나, 또는 R5및 R6은 이들이 연결된 탄소원자와 합쳐져서 C5-C8시클로헥실리덴 고리를 형성하며, A는이고 X는 산소이며, 또 n은 2 내지 10의 수인 일반식(I)의 단량체성 화합물 및 일반식(II)의 올리고머성 화합물.The compound of claim 1, wherein R 1 is hydrogen, R 2 is hydrogen, C 1 -C 4 alkyl or cyclohexyl, R 3 is hydrogen, R 4 is hydrogen or C 1 -C 4 alkyl, R 5 and R 6 independently of one another is hydrogen or C 1 -C 4 alkyl, or R 5 and R 6 combine with the carbon atom to which they are linked to form a C 5 -C 8 cyclohexylidene ring, and A is And X is oxygen, and n is a number from 2 to 10 and a monomeric compound of formula (I) and an oligomeric compound of formula (II). 하기 일반식(VI)의 비스페놀 또는 그의 혼합물을 먼저 삼연화인과 반응시켜 하기 일반식(VII)의 화합물을 생성한 다음 일반식(VII)의 화합물을 하기 일반식(V)의 HALS 화합물 또는 그의 혼합물과 반응시켜 제1항에 따른 일반식(II)의 올리고YN머성 화합물을 제조하는 방법:The bisphenol of the general formula (VI) or a mixture thereof is first reacted with phosphorus tritide to give a compound of the general formula (VII), and then the compound of the general formula (VII) is a HALS compound of the general formula (V) or a mixture thereof A process for preparing an oligoYNmeric compound of formula (II) according to claim 1 with 식중에서, R1, R2, R3, R4, A 및 X는 상기 정의한 바와 같다.Wherein R 1 , R 2 , R 3 , R 4 , A and X are as defined above. 하기 일반식(VI)의 비스페놀 또는 그이 혼합물을 삼연화인 및 하기 일반식(V)의 HALS 화합물 또는 그의 혼합물과 반응시켜 수득할 수 있는 올리고머성 생성물:Oligomeric products obtainable by reacting bisphenols of formula (VI) or mixtures thereof with phosphorus trichloride and HALS compounds of formula (V) or mixtures thereof: 식중에서, R1, R2, R3, R4, A 및 X는 상기 정의한 바와 같다.Wherein R 1 , R 2 , R 3 , R 4 , A and X are as defined above. a) 산화적, 열적 또는 광 유도 분해되기 쉬운 물질 및 b) 제1항에 따른 한개 이상의 일반식(I) 또는 (II)의 화합물 또는 제9항에 따른 한개 이상의 올리고머성 생성물을 포함하는 조성물.A composition comprising a) a material prone to oxidative, thermal or photoinductive degradation, and b) at least one compound of formula (I) or (II) according to claim 1 or at least one oligomeric product according to claim 9. 제10항에 있어서, 상기 성분 a) 및 b)이외에 추가의 첨가제를 더 포함하는 조성물.The composition of claim 10 further comprising additional additives in addition to components a) and b). 제11항에 있어서, 상기 추가의 첨가제가 페놀성 산화방지제, 광 안정화제 및/또는 가공 안정화제인 조성물.The composition of claim 11 wherein said additional additive is a phenolic antioxidant, light stabilizer and / or process stabilizer. 제11항에 있어서, 상기 추가의 첨가제가 한개 이상의 벤조푸란-2-온 유형의 화합물인 조성물.The composition of claim 11, wherein said additional additive is one or more benzofuran-2-one type compounds. 제10항에 있어서, 상기 성분 a)가 천연, 반합성 또는 합성 중합체인 조성물.The composition of claim 10 wherein component a) is a natural, semisynthetic or synthetic polymer. 제10항에 있어서, 상기 성분 a)가 열가소성 중합체인 조성물.The composition of claim 10 wherein component a) is a thermoplastic polymer. 제10항에 있어서, 상기 성분 a)가 폴리올레핀인 조성물.The composition of claim 10, wherein component a) is a polyolefin. 제10항에 있어서, 상기 성분 a)가 폴리에틸렌 또는 폴리프로필렌인 조성물.The composition of claim 10 wherein component a) is polyethylene or polypropylene. 제1항에서 정의된 한개 이상의 일반식(I) 또는 (II)의 화합물 또는 제9항에 따른 한개 이상의 올리고머성 생성물을 유기물질에 혼입 또는 도포하는 것을 포함하는 산화적, 열적 또는 광 유도 분해로 부터 유기물질을 안정화시키는 방법.An oxidative, thermal or photo-induced decomposition comprising incorporating or applying one or more compounds of formula (I) or (II) as defined in claim 1 or one or more oligomeric products according to claim 9 into an organic material. To stabilize organic materials. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
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