公开(公告)号：CA2068317C

公开(公告)日：1995-10-24

申请号：CA2068317

申请日：1990-11-03

Applicant: HOECHST AG

Inventor： BOEHSHAR MANFRED ,  KLEINER HANS-JERG

IPC: C07F9/146

Abstract: The invention relates to a process for obtaining phosphorous acid-bis-(2,4-di-tert-butyl-phenyl) ester halides of formula (1), in which a phosphorous acid-2,4-di-tert-butyl-phenyl ester dihalide of formula (II) is heated in the presence of a compound containing nitrogen and/or phosphorus and acting as a catalyst to 130 280.degree.C and removing the phosphorus trihalide produced by disproportionation from the reaction mixture.

公开(公告)号：AT111915T

公开(公告)日：1994-10-15

申请号：AT90907020

申请日：1990-05-16

Applicant: HOECHST AG

Inventor： BOEHSHAR MANFRED ,  KLEINER HANS-JERG ,  PFAHLER GERHARD

IPC: C07F9/48 ,  C07F9/6571 ,  C07F9/6574 ,  C08K5/53 ,  C08K5/5393 ,  C08L23/02 ,  C09K15/32

Abstract: Process for preparing aryl esters of phosphonous acid of formula (V), where A is non-existent or a direct bond or a divalent hydrocarbon bridge with 1 to 6 carbon atoms, which can be substituted by the groups mentioned below, or a heteroatom, cycloalkylidene with 4 to 8 carbon atoms or phenylalkylidene with 7 to 12 carbon atoms, n is equal to 1 or 2, R as a monovalent residue denotes certain non-aromatic or aromatic hydrocarbon residues, the aromatic residues denoting substituents such as alkyl, alkoxy, alkylthio, dialkylamino, aryl, aryloxy or halogen, and as a divalent residue denotes a phenylene or naththylene residue, which can carry non-aromatic hydrocarbon residues as substituents, R is a non-aromatic hydrocarbon residue with 1 to 18 carbon atoms, aryl, arylmethyl, arylethyl or arylisopropyl, each aryl containing 6 to 10 carbon atoms, and R denotes hydrogen or one of the groups mentioned under R . In a first stage a halogenated hydrocarbon R (-Hal)n, in which R has the above-mentioned meaning, n = 1 or 2, and the halogen has an atomic weight of at least 35, is converted under Grignard conditions with at least molar quantities of magnesium to the corresponding organomagnesium compounds R (MgHal)n. These are reacted in a second stage with phosphoric acid-bis-arylester halides of formula (VI), where R , R and Hal have the above-mentioned meanings, to form the phosphonous acid arylester (V). The invention also relates to a plastics moulding material, in particular a polyolefin moulding material, containing the phosphonous acid arylester of formula (V). The properties of the moulding material are superior to those of materials which contain phosphonites produced by prior art techniques.

公开(公告)号：DE59102579D1

公开(公告)日：1994-09-22

申请号：DE59102579

申请日：1991-06-22

Applicant: HOECHST AG

Inventor： BOEHSHAR MANFRED ,  KLEINER HANS-JERG ,  PFAHLER GERHARD

IPC: C09K15/32 ,  C07F9/6571 ,  C07F9/6574 ,  C08K5/53 ,  C08K5/5377 ,  C08L101/00

Abstract: PCT No. PCT/EP91/01158 Sec. 371 Date Dec. 23, 1992 Sec. 102(e) Date Dec. 23, 1992 PCT Filed Jun. 22, 1991 PCT Pub. No. WO92/00306 PCT Pub. Date Jan. 9, 1992.A dibenzo-[c,e] [1,2] oxaphosphorine of the formula I and process of making said compound (I) wherein n=1 or 2 and in which R1 is a monovalent or divalent aromatic radical wherein a Grignard compound R1(MgHal)n is reacted with 6-chloro-6H-dibenzo[c,e][1,2] oxaphosphorine. This compound optionally with phenolic antioxidants, provides stabilization in polymers.

公开(公告)号：AT110082T

公开(公告)日：1994-09-15

申请号：AT91911955

申请日：1991-06-22

Applicant: HOECHST AG

Inventor： BOEHSHAR MANFRED ,  KLEINER HANS-JERG ,  PFAHLER GERHARD

IPC: C09K15/32 ,  C07F9/6571 ,  C07F9/6574 ,  C08K5/53 ,  C08K5/5377 ,  C08L101/00

Abstract: PCT No. PCT/EP91/01158 Sec. 371 Date Dec. 23, 1992 Sec. 102(e) Date Dec. 23, 1992 PCT Filed Jun. 22, 1991 PCT Pub. No. WO92/00306 PCT Pub. Date Jan. 9, 1992.A dibenzo-[c,e] [1,2] oxaphosphorine of the formula I and process of making said compound (I) wherein n=1 or 2 and in which R1 is a monovalent or divalent aromatic radical wherein a Grignard compound R1(MgHal)n is reacted with 6-chloro-6H-dibenzo[c,e][1,2] oxaphosphorine. This compound optionally with phenolic antioxidants, provides stabilization in polymers.

公开(公告)号：NO174103B

公开(公告)日：1993-12-06

申请号：NO895141

申请日：1989-12-20

Applicant: HOECHST AG

Inventor： BOEHSHAR MANFRED ,  KLEINER HANS-JERG ,  WALDMANN KARL ,  PFAHLER GERHARD

IPC: C09K15/32 ,  C07F3/02 ,  C07F9/40 ,  C07F9/48 ,  C08K5/53 ,  C08K5/5393 ,  C08L23/00 ,  C08L23/02

Abstract: Process for the preparation of organophosphorus derivatives of 2,4-di-t-butylphenol having a high content of organophosphorus derivatives of biphenyl, characterised in that, in the first step, a 4,4'-dihalobiphenyl whose halogen has an atomic weight of at least 35 is reacted under Grignard conditions with magnesium to give the corresponding Grignard compound, which is further reacted, in a second step, with bis(2,4-di-t-butylphenyl) chlorophosphite of the formula IV … … to form a mixture in which at least 50% by weight of the phosphorus is bound in the form of tetrakis(2,4-di-t-butylphenyl)-4,4'-biphenylene diphosphonite of the formula I … … the bonding of the phosphorus being determined by P-NMR analysis. … The invention furthermore relates to a polyolefin moulding composition which contains tetrakis(2,4-di-t-butylphenyl)- 4,4'-biphenylene diphosphonite of the formula I prepared by reacting a 4,4'-dihalobiphenyl whose halogen has an atomic weight of at least 35, with magnesium to give the Grignard compound and subsequent reaction thereof with bis(2,4-di-t-butylphenyl) chlorophosphite. … The moulding composition has improved properties compared with moulding compositions which contain said phosphonite prepared in accordance with the prior art. … The invention also relates to a process for the preparation of 4,4'-dihalomagnesium compounds of biphenyl by reacting a 4,4'-dihalobiphenyl whose halogen has an atomic weight of at least 35 with magnesium in the absence of an entrainer, in which process a 4,4'-dihalobiphenyl whose halogen has an atomic weight of at least 35 is reacted with finely divided magnesium kept in suspension.

公开(公告)号：CA2065406A1

公开(公告)日：1991-02-27

申请号：CA2065406

申请日：1990-08-18

Applicant: HOECHST AG

Inventor： BOEHSHAR MANFRED ,  KLEINER HANS-JERG ,  PFAHLER GERHARD

IPC: C07F9/146 ,  C07F9/26 ,  C07F9/48 ,  C07F9/553 ,  C07F9/59 ,  C07F9/6533 ,  C07F9/6553 ,  C08K5/53 ,  C08K5/5399 ,  C08L23/02 ,  C08L101/00 ,  C08K5/51

Abstract: HOE 89/F 282 K of the disclosure: Aryl halophosphoramidites, aryl phosphonamidites, processes for their preparation and their use for the stabilization of plastics A process for the preparation of aryl phosphonamidites of the formula (I) (I) in which R1, as a univalent radical, is certain aromatic hydrocarbon radicals which can carry substituents, in particular a non-aromatic hydrocarbon radical, alkoxy, alkylthio, aryl, aryloxy or halogen, and R1, as a divalent radical, is a phenylene, naphthylene or biphenylene radical which can carry non-aromatic hydrocarbon radicals as substituents, R2 is a non-aromatic hydrocarbon radical, aryl or an optionally substituted arylmethyl radical, R3 is hydrogen, alkoxy or alkylthio or a group mentioned under R2, R4 and R5 are in each case C1-C22-alkyl, C2-C21-oxaalkyl or -thiaalkyl, C3-C18-alkenyl or -alkynyl, C3-C24-alkoxycar-bonylalkyl, C5-C12-cycloalkyl, C6-C14-aryl, C7-C15-arylalkyl or an optionally substituted C5-C17,-piperidin-4-yl qroup, or, together with the nitrogen atom, form a ring system having 5 to 7 ring atoms which can still additionally contain an oxygen, nitrogen or sulfur atom bonded via at least one carbon atom, and n = 1 or 2, in which initially a halide R1(-X)n, in which R1 and n have the abovementioned meaning and X is a halogen having an atomic weight of at least 35, is reacted with magnesium to give the corresponding Grignard compounds R1(MgX)n and these are reacted further with aryl halophosphoramidites of the formula (II) (II) in which R2 to R5 have the meaning mentioned and X is chlorine or bromine, to give the phosphonamidites (I). The invention further relates to certain compounds of the formulae (I) and (II), to a process for the preparation of compounds of the formula (II), to the use of compounds of the formula (I) alone or in combination with a phenolic antioxidant for the stabilization of plastics and to the plastic molding compositions stabilized in this way. These molding compositions are distinguished by improved properties compared to those molding compositions which contain phosphonites prepared according to the prior art.

公开(公告)号：CA2058762A1

公开(公告)日：1990-11-21

申请号：CA2058762

申请日：1990-05-16

Applicant: HOECHST AG

Inventor： BOEHSHAR MANFRED ,  KLEINER HANS-JERG ,  PFAHLER GERHARD

IPC: C07F9/48 ,  C07F9/6571 ,  C07F9/6574 ,  C08K5/53 ,  C08K5/5393 ,  C08L23/02 ,  C09K15/32 ,  C08L101/00

Abstract: A process for the preparation of aryl phosphonites of the formula V (see formula I) in which A is non-existent or a direct bond or a divalent hydrocarbon bridge having 1 to 6 carbon atoms which may be substituted by groups mentioned further below under R1, or is a hetero atom, cycloalkylidene having 4 to 8 carbon atoms or phenylalkylidene having 7 to 12 carbon atoms, n is 1 or 2, R1 as monovalent radical is certain non-aromatic or aromatic hydrocarbon radicals, in which the aromatic radicals are substituents such as alkyl, alkoxy, alkylthio, dialkylamino, aryl, aryloxy or halogen, and as divalent radical a phenylene or naphthylene radical, which may carry non-aromatic hydrocarbon radicals as substituents, R2 is a non-aromatic hydrocarbon radical having 1 to 18 carbon atoms, aryl, arylmethyl, arylethyl or arylisopropyl, in which the aryl in each case contains 6 to carbon atoms, and R3 is hydrogen or a group mentioned under R2, in which process in a first step a hydrocarbon halide R1(-Hal)n, in which R1 has the abovementioned meaning, n is = 1 or 2 and the halogen has an atomic weight of at least 35, is reacted under Grignard conditions with at least molar amounts of magnesium to give the corresponding Grignard compounds R1(MgHal)n and these compounds are reacted in a second step with bisaryl halophosphonites of the formula VI (see formula I) , in which R2, R3 and Hal ha,e the abovementioned meaning, with the formation of the aryl phosphonites V. The invention further relates to a plastic molding composition, in particular a polyolefin molding composition containing aryl phosphonites of the formula V. The molding composition is distinguished by improved properties compared with those molding compositions containing phosphonites prepared by the prior art.

公开(公告)号：FI896086A0

公开(公告)日：1989-12-19

申请号：FI896086

申请日：1989-12-19

Applicant: HOECHST AG

Inventor： BOEHSHAR MANFRED ,  KLEINER HANS-JERG ,  WALDMANN KARL ,  PFAHLER GERHARD

IPC: C09K15/32 ,  C07F3/02 ,  C07F9/40 ,  C07F9/48 ,  C08K5/53 ,  C08K5/5393 ,  C08L23/00 ,  C08L23/02 ,  C07F

Abstract: Process for the preparation of organophosphorus derivatives of 2,4-di-t-butylphenol having a high content of organophosphorus derivatives of biphenyl, characterised in that, in the first step, a 4,4'-dihalobiphenyl whose halogen has an atomic weight of at least 35 is reacted under Grignard conditions with magnesium to give the corresponding Grignard compound, which is further reacted, in a second step, with bis(2,4-di-t-butylphenyl) chlorophosphite of the formula IV … … to form a mixture in which at least 50% by weight of the phosphorus is bound in the form of tetrakis(2,4-di-t-butylphenyl)-4,4'-biphenylene diphosphonite of the formula I … … the bonding of the phosphorus being determined by P-NMR analysis. … The invention furthermore relates to a polyolefin moulding composition which contains tetrakis(2,4-di-t-butylphenyl)- 4,4'-biphenylene diphosphonite of the formula I prepared by reacting a 4,4'-dihalobiphenyl whose halogen has an atomic weight of at least 35, with magnesium to give the Grignard compound and subsequent reaction thereof with bis(2,4-di-t-butylphenyl) chlorophosphite. … The moulding composition has improved properties compared with moulding compositions which contain said phosphonite prepared in accordance with the prior art. … The invention also relates to a process for the preparation of 4,4'-dihalomagnesium compounds of biphenyl by reacting a 4,4'-dihalobiphenyl whose halogen has an atomic weight of at least 35 with magnesium in the absence of an entrainer, in which process a 4,4'-dihalobiphenyl whose halogen has an atomic weight of at least 35 is reacted with finely divided magnesium kept in suspension.