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    4.
    发明专利
    未知

    公开(公告)号：SE308354B

    公开(公告)日：1969-02-10

    申请号：SE1501564

    申请日：1964-12-11

    Applicant: UNIVERSAL OIL PROD CO

    Inventor： LATOS E ,  HAYES C

    IPC: C07D209/70 ,  C08K5/3417 ,  C09K15/04 ,  C09K15/06 ,  C10G73/00 ,  C10L1/22 ,  C10L1/222 ,  C10M133/02 ,  C10M1/24

    Abstract: An additive for stabilizing organic substances such as oils, fuels, waxes, greases, synthetic resins and rubber comprises the reaction product of an amine and either a polyhalopolyhydroalkanonaphthalene dicarboxylic acid of formula where X and Y are halogen, hydrogen, or an alkyl radical having 1 to 10 carbon atoms, at least two X's being halogen, m is 1 to 4 and n is 0 to 4, or the anhydride or an ester of such an acid. The acid may be prepared by condensing a cyclohexenedicarboxylic acid, prepared by a Diels-Alder reaction, with a halocycloalkadiene. For example 1,3-butadiene is condensed with maleic acid to form 1,2,3,5-tetrahydrophthalic acid, which is then condensed with hexachlorocyclopentadiene to form 5,6,7,8,9,9 - hexachloro - 1,2,3,4,4a,5,8,8a - octahydro - 5,8 - methano - 2,3 - naphthalene dicarboxylic acid. The anhydride is formed by starting with maleic anhydride. The ester is formed by reaction of the product with an alcohol having 1 to 25 carbon atoms. The amine may be a mono- or polyamine and may have 2 to 50 carbon atoms. Amines mentioned include the series from octyl to eicosyl amine, tallow amine, stearyl amine, coconut amine, N-alkyldiaminoalkanes, particularly N-alkyl-1,3-diaminopropane, alkylene diamines and polyalkylene polyamines, the latter preferably being N-alkyl substituted, aromatic amines, amino phenyl ethers, sulphides and substituted methanes and other alkanes, and cycloalkyl amines. A sulphur-containing amine, which may be desirable when the eventual additive is to be incorporated in a lubricating oil, may also be formed by reacting an N-alkylated or N,N-dialkylated alkylene polyamine with carbon disulphide. The reaction product of the acid, anhydride or ester with the amine may be a salt, including the half salt, or a condensation product. To form the salt, the reactants preferably dissolved in a solvent, are mixed and left at up to 66 DEG C. under up to 34 atmospheres for up to 12 hours. To form the condensation product, the reactants are refluxed in a solvent at a temperature at which water is eliminated, suitably azeotropically. The product may be an imide, or imide-amine, but is ill-defined and mixtures, possibly including heterocyclic rings, are thought to be formed. The additive may be used in the reaction solvent, or this may be removed and the additive redissolved in an alkyl or polyalkylphenol. Lubricating oils stabilized by the additive include mineral oils, oils of animal, marine or vegetable origin and synthetic oils, e.g. aliphatic esters, polyalkylene oxides, silicones, phosphoric and silicic acid esters, fluorinated hydrocarbons, neopentyl glycol esters and trimethylol alkanes. Greases stabilized may be whale grease, wool grease, those made from inedible fats, tallow, butcher's waste and synthetic greases. The additive is used in proportions of 0.01 to 25%.ALSO:Additives for stabilizing organic compounds (see Division C5) are made by reacting an amine with an acid of formula wherein X = Cl, m = 1 and either n = 0 (I) or n = 1, Y = H (II), or with an anhydride of such acid. In examples, (a) salts are made from I and oleylamine, N-alkyl (C12- 20)-1,3,-diamino-propane (III), or NH(CH2CH2NHCHEtCH2CHMeEt)2/CS2 reaction product; (b) cyclic imides are made from I-anhydride with NH(CH2CH2NH2)2, and II-anhydride with III; (c) a product, apparently an amidic acid, is made by reacting in a 1:1 molar ratio, II anhydride with N,N1-di-secoctyl-p-phenylenediamine.

    5.
    发明专利
    未知

    公开(公告)号：SE344337B

    公开(公告)日：1972-04-10

    申请号：SE1747668

    申请日：1968-12-19

    Applicant: UNIVERSAL OIL PROD CO

    Inventor： LATOS E ,  HAYES C

    IPC: C07C23/20 ,  C07C61/28 ,  C07C61/29 ,  C07C233/00 ,  C07D209/76 ,  C07F9/02 ,  C07F9/06 ,  C07F9/11 ,  C07F9/17 ,  C08G69/48 ,  C09K15/06 ,  C09K15/32 ,  C10M137/14 ,  C10M159/12 ,  C10M169/00 ,  F02B3/06 ,  C10M1/44

    Abstract: 1,199,747. Halogen-containing dicarboxylic acid-amine-phosphate reaction products. UNIVERSAL OIL PRODUCTS CO. 3 Oct., 1967 [5 Oct., 1966], No. 44987/67. Addition to 1,084,036. Heading C2C. [Also in Division C5] An acid-amine-phosphate reaction product is prepared by reacting (1) a polyhalopolyhydropolycyclicdicarboxylic acid of general formula in which X and Y are halogen, hydrogen or C 1 -C 10 alkyl, at least two X's being halogen, and n and p are 0, 1, or 2, or (2) an anhydride of such an acid, with a polyamine, and reacting the resultant intermediate product with an alkyl acid phosphate, pyrophosphate or acid thiophosphate using from 3 to 30 mol. of intermediate product per mol. of phosphate. The acid phosphate or thiophosphate is a mono- or di-alkyl ester or mixture thereof, preferably containing at least one C 6 -C 20 alkyl group, or is an acid phosphate or thiophosphate of an oxyalkylenated alcohol or phenol. The acid or anhydride may be reacted with the polyamine in the presence of a solvent and the reaction may either be carried out at 80-250‹ C., in which range water is eliminated from the product, or at less than 80‹ C. under mild conditions to avoid the elimination of water. Suitable polyamines include alkylene polyamines, N- alkyl-diaminoalkanes (especially those in which the N-alkyl group is C 8 -C 25 ), aromatic diamines and beta-alkylpolyamines. The products are used as stabilizing additives in lubricating oils and greases.

    6.
    发明专利
    未知

    公开(公告)号：DK117516B

    公开(公告)日：1970-05-04

    申请号：DK584166

    申请日：1966-11-10

    Applicant: UNIVERSAL OIL PROD CO

    Inventor： LATOS E ,  HAYES C

    IPC: C07C23/20 ,  C07C61/28 ,  C07C61/29 ,  C07C233/00 ,  C07D209/76 ,  C07F9/02 ,  C07F9/06 ,  C07F9/11 ,  C07F9/17 ,  C08G69/48 ,  C09K15/06 ,  C09K15/32 ,  C10M137/14 ,  C10M159/12 ,  C10M169/00 ,  F02B3/06 ,  C10M1/44 ,  C10M3/38 ,  C10M5/24 ,  C10M7/42

    Abstract: 1,199,747. Halogen-containing dicarboxylic acid-amine-phosphate reaction products. UNIVERSAL OIL PRODUCTS CO. 3 Oct., 1967 [5 Oct., 1966], No. 44987/67. Addition to 1,084,036. Heading C2C. [Also in Division C5] An acid-amine-phosphate reaction product is prepared by reacting (1) a polyhalopolyhydropolycyclicdicarboxylic acid of general formula in which X and Y are halogen, hydrogen or C 1 -C 10 alkyl, at least two X's being halogen, and n and p are 0, 1, or 2, or (2) an anhydride of such an acid, with a polyamine, and reacting the resultant intermediate product with an alkyl acid phosphate, pyrophosphate or acid thiophosphate using from 3 to 30 mol. of intermediate product per mol. of phosphate. The acid phosphate or thiophosphate is a mono- or di-alkyl ester or mixture thereof, preferably containing at least one C 6 -C 20 alkyl group, or is an acid phosphate or thiophosphate of an oxyalkylenated alcohol or phenol. The acid or anhydride may be reacted with the polyamine in the presence of a solvent and the reaction may either be carried out at 80-250‹ C., in which range water is eliminated from the product, or at less than 80‹ C. under mild conditions to avoid the elimination of water. Suitable polyamines include alkylene polyamines, N- alkyl-diaminoalkanes (especially those in which the N-alkyl group is C 8 -C 25 ), aromatic diamines and beta-alkylpolyamines. The products are used as stabilizing additives in lubricating oils and greases.

    9.
    发明专利
    未知

    公开(公告)号：DK116953B

    公开(公告)日：1970-03-02

    申请号：DK609464

    申请日：1964-12-11

    Applicant: UNIVERSAL OIL PROD CO

    Inventor： LATOS E ,  HAYES C

    IPC: C07D209/70 ,  C08K5/3417 ,  C09K15/04 ,  C09K15/06 ,  C10G73/00 ,  C10L1/22 ,  C10L1/222 ,  C10M133/02 ,  C10M1/32 ,  C10M3/26 ,  C10M5/20 ,  C10M7/30

    Abstract: An additive for stabilizing organic substances such as oils, fuels, waxes, greases, synthetic resins and rubber comprises the reaction product of an amine and either a polyhalopolyhydroalkanonaphthalene dicarboxylic acid of formula where X and Y are halogen, hydrogen, or an alkyl radical having 1 to 10 carbon atoms, at least two X's being halogen, m is 1 to 4 and n is 0 to 4, or the anhydride or an ester of such an acid. The acid may be prepared by condensing a cyclohexenedicarboxylic acid, prepared by a Diels-Alder reaction, with a halocycloalkadiene. For example 1,3-butadiene is condensed with maleic acid to form 1,2,3,5-tetrahydrophthalic acid, which is then condensed with hexachlorocyclopentadiene to form 5,6,7,8,9,9 - hexachloro - 1,2,3,4,4a,5,8,8a - octahydro - 5,8 - methano - 2,3 - naphthalene dicarboxylic acid. The anhydride is formed by starting with maleic anhydride. The ester is formed by reaction of the product with an alcohol having 1 to 25 carbon atoms. The amine may be a mono- or polyamine and may have 2 to 50 carbon atoms. Amines mentioned include the series from octyl to eicosyl amine, tallow amine, stearyl amine, coconut amine, N-alkyldiaminoalkanes, particularly N-alkyl-1,3-diaminopropane, alkylene diamines and polyalkylene polyamines, the latter preferably being N-alkyl substituted, aromatic amines, amino phenyl ethers, sulphides and substituted methanes and other alkanes, and cycloalkyl amines. A sulphur-containing amine, which may be desirable when the eventual additive is to be incorporated in a lubricating oil, may also be formed by reacting an N-alkylated or N,N-dialkylated alkylene polyamine with carbon disulphide. The reaction product of the acid, anhydride or ester with the amine may be a salt, including the half salt, or a condensation product. To form the salt, the reactants preferably dissolved in a solvent, are mixed and left at up to 66 DEG C. under up to 34 atmospheres for up to 12 hours. To form the condensation product, the reactants are refluxed in a solvent at a temperature at which water is eliminated, suitably azeotropically. The product may be an imide, or imide-amine, but is ill-defined and mixtures, possibly including heterocyclic rings, are thought to be formed. The additive may be used in the reaction solvent, or this may be removed and the additive redissolved in an alkyl or polyalkylphenol. Lubricating oils stabilized by the additive include mineral oils, oils of animal, marine or vegetable origin and synthetic oils, e.g. aliphatic esters, polyalkylene oxides, silicones, phosphoric and silicic acid esters, fluorinated hydrocarbons, neopentyl glycol esters and trimethylol alkanes. Greases stabilized may be whale grease, wool grease, those made from inedible fats, tallow, butcher's waste and synthetic greases. The additive is used in proportions of 0.01 to 25%.ALSO:Additives for stabilizing organic compounds (see Division C5) are made by reacting an amine with an acid of formula wherein X = Cl, m = 1 and either n = 0 (I) or n = 1, Y = H (II), or with an anhydride of such acid. In examples, (a) salts are made from I and oleylamine, N-alkyl (C12- 20)-1,3,-diamino-propane (III), or NH(CH2CH2NHCHEtCH2CHMeEt)2/CS2 reaction product; (b) cyclic imides are made from I-anhydride with NH(CH2CH2NH2)2, and II-anhydride with III; (c) a product, apparently an amidic acid, is made by reacting in a 1:1 molar ratio, II anhydride with N,N1-di-secoctyl-p-phenylenediamine.

    10.
    发明专利
    未知

    公开(公告)号：SE356743B

    公开(公告)日：1973-06-04

    申请号：SE1361867

    申请日：1967-10-04

    Applicant: UNIVERSAL OIL PROD CO

    Inventor： LATOS E

    IPC: C07C23/20 ,  C07C61/28 ,  C07C61/29 ,  C07C233/00 ,  C07D209/76 ,  C07F9/02 ,  C07F9/06 ,  C07F9/11 ,  C07F9/17 ,  C08G69/48 ,  C09K15/06 ,  C09K15/32 ,  C10M137/14 ,  C10M159/12 ,  C10M169/00 ,  F02B3/06 ,  C07C135/00 ,  C10M1/44

    Abstract: 1,199,747. Halogen-containing dicarboxylic acid-amine-phosphate reaction products. UNIVERSAL OIL PRODUCTS CO. 3 Oct., 1967 [5 Oct., 1966], No. 44987/67. Addition to 1,084,036. Heading C2C. [Also in Division C5] An acid-amine-phosphate reaction product is prepared by reacting (1) a polyhalopolyhydropolycyclicdicarboxylic acid of general formula in which X and Y are halogen, hydrogen or C 1 -C 10 alkyl, at least two X's being halogen, and n and p are 0, 1, or 2, or (2) an anhydride of such an acid, with a polyamine, and reacting the resultant intermediate product with an alkyl acid phosphate, pyrophosphate or acid thiophosphate using from 3 to 30 mol. of intermediate product per mol. of phosphate. The acid phosphate or thiophosphate is a mono- or di-alkyl ester or mixture thereof, preferably containing at least one C 6 -C 20 alkyl group, or is an acid phosphate or thiophosphate of an oxyalkylenated alcohol or phenol. The acid or anhydride may be reacted with the polyamine in the presence of a solvent and the reaction may either be carried out at 80-250‹ C., in which range water is eliminated from the product, or at less than 80‹ C. under mild conditions to avoid the elimination of water. Suitable polyamines include alkylene polyamines, N- alkyl-diaminoalkanes (especially those in which the N-alkyl group is C 8 -C 25 ), aromatic diamines and beta-alkylpolyamines. The products are used as stabilizing additives in lubricating oils and greases.

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