Patents Assigned to Cincinnati Milacron Chemicals, Inc.
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Patent number: 4205176Abstract: Oxazolines having at least one 3,5-dialkyl-4-hydroxypheny l alkanoic acid ester substituent are provided. Such oxazolines are found to be useful an antioxidants in organic substances normally susceptible to oxidative deterioration.Type: GrantFiled: October 18, 1978Date of Patent: May 27, 1980Assignee: Cincinnati Milacron Chemicals Inc.Inventors: Mary J. Zestermann, John F. Hussar
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Patent number: 4179432Abstract: Polymers of olefins are stabilized against ultraviolet light by a synergistic combination of stabilizers including (1) a hydroxybenzophenone and (2) an organotin compound of the formula:(a) RnSn--SR.sup.1 COOR.sup.2) 4-n,(b) RnSn--S--R.sup.2) 4-n,(c) RnSn--S R.sup.1 OOCR.sup.2) 4-n,(d) ((R).sub.3 Sn-S).sub.x R.sup.4 --Z).sub.y, or ##STR1## where R is alkyl, alkenyl, aryl, aralkyl, alkaryl or cycloalkyl, R.sup.1 is alkylene, arylene, cycloalkylene, aralkylene or alkarylene, R.sup.2 is an alkyl, aryl, aralkyl, alkenyl, alkaryl or cycloalkyl, R.sup.5 is alkylene, R.sup.4 is aliphatic, aromatic, araliphatic, alkyl substituted aromatic or cycloaliphatic radical of at least 2 carbon atoms and having a free valence of x+y, Z is --OH, --COOH, --COOR.sup.2 or --OOCR.sup.2 or Z can be a mixture of these radicals if y is greater than 1, x is 1 to 4, y is 0 to 3, x+y is 1 to 4 and n is 1 to 3. Preferably the olefin is polyethylene or polypropylene. Preferably the hydroxybenzophenone also has at least one alkoxy group.Type: GrantFiled: September 2, 1975Date of Patent: December 18, 1979Assignee: Cincinnati Milacron Chemicals, Inc.Inventor: Kenneth R. Molt
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Patent number: 4173541Abstract: Novel polynuclear hindered phenols having three hindered phenol groups each bonded through a methylene group to a substituted aromatic nucleus and methods of making same are provided which have stabilizing activity in organic substances normally susceptible to oxidative degradation.Type: GrantFiled: June 5, 1978Date of Patent: November 6, 1979Assignee: Cincinnati Milacron Chemicals Inc.Inventor: Kenneth R. Molt
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Patent number: 4120845Abstract: A polyvinyl chloride resin stabilizer is provided having a high concentration of tin, in the range from about 10% to about 42% by weight, and a high concentration of sulfur, within the range from about 8% to about 42% sulfur, comprising at least one monoorganotin or diorganotin mercapto alkanol carboxylic ester (or mercapto alkyl carboxylate), mono or poly sulfide and preferably mixed monoorganotin and diorganotin mercaptoalkyl carboxylic acid ester sulfides, especially having 4 to 50% of the diorganotin compound. Polyvinyl chloride resin compositions are also provided, containing these compounds.Type: GrantFiled: August 22, 1977Date of Patent: October 17, 1978Assignee: Cincinnati Milacron Chemicals, Inc.Inventor: Thomas G. Kugele
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Patent number: 4118371Abstract: Halogen containing polymers are stabilized against deterioration by novel organotin mercaptoalkanol ester sulfides or polysulfides characterized by having at least one sulfide or polysulfide bridged tin to tin group and at least one oxygen containing organic group bonded to tin through a carbon atom.Type: GrantFiled: April 29, 1977Date of Patent: October 3, 1978Assignee: Cincinnati Milacron Chemicals Inc.Inventor: Thomas Gordon Kugele
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Patent number: 4062881Abstract: A polyvinyl chloride resin stabilizer is provided having a high concentration of tin, in the range from about 10% to about 42% by weight, and a high concentration of sulfur, within the range from about 8% to about 42% sulfur, comprising at least one monoorganotin or diorganotin mercapto alkanol carboxylic ester (or mercapto alkyl carboxylate), mono or poly sulfide and preferably mixed monoorganotin and diorganotin mercaptoalkyl carboxylic acid ester sulfides, especially having 4 to 50% of the diorganotin compound. Polyvinyl chloride resin compositions are also provided, containing these compounds.Type: GrantFiled: July 26, 1974Date of Patent: December 13, 1977Assignee: Cincinnati Milacron Chemicals, Inc.Inventor: Thomas G. Kugele
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Patent number: 4012399Abstract: Ultraviolet light absorbers and stabilizers, particularly for monolefin polymers, are provided from metal complexes of trivalent phosphorus compounds of the formulaeMe (L).sub.n (A).sub.m (L').sub.owhere Me is preferably nickel but can be manganese, iron, copper, molybdenum or tungsten, L is P(X)(Y)(Z) where any one or all of X, Y and Z can be O hydrocarbyl, ##STR1## where R.sub.31 and R.sub.32 are hydrocarbyl or hydrogen, S hydrocarbyl, hydrocarbyl, 2 or 3 of X, Y and Z can form one or more heterocyclic rings with P, A is an anion such as halogen, e.g. Cl, Br, I or F, NO.sub.3, C104, R.sub.33 COO- where R.sub.33 is hydrocarbyl, any hydrocarbyl group can have 1 or 2 halogen substituents, m is 0 or a small whole number, e.g. 1,2,3,4, L' is CO, NO, CN, halogen, o is zero or a small whole number, e.g. 1,2,3,4, n is 1 or another small whole number, e.g. 2,3,4, o+m+n is not greater than the highest coordination number of the metal.Type: GrantFiled: November 4, 1975Date of Patent: March 15, 1977Assignee: Cincinnati Milacron Chemicals, Inc.Inventors: Ingenuin Hechenbleikner, Thomas G. Kugele, John F. Hussar
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Patent number: 3979359Abstract: Organotin compounds are prepared having (1) at least two tin atoms linked by a bridge through sulfur, carboxylate or both and containing at least two carbon atoms in the bridge, (2) directly attached to the tin atoms one to two alkyl groups containing one to eight carbon atoms and (3) a mercaptoalkanol or derivative thereof. The compounds are useful to stabilize halogen containing vinyl and vinylidene polymers, e.g. polyvinyl chloride.Type: GrantFiled: November 15, 1974Date of Patent: September 7, 1976Assignee: Cincinnati Milacron Chemicals, Inc.Inventors: Thomas G. Kugele, Arthur F. Koeniger
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Patent number: 3970678Abstract: The following reactions are carried out in the presence of aprotic solvents as catalysts: ##EQU1## WHERE R, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are alkyl, cycloalkyl, alkenyl, aryl or aralkyl, R.sub.1 is ##EQU2## allyl, methallyl or benzyl, R.sub.7 is alkyl, cycloalkyl, alkenyl or aralkyl, R.sub.12 is alkyl or alkenyl, X is chlorine or bromine and n is 1 or 2. The aprotic solvents are ##EQU3## WHERE R.sub.8 is H or CH.sub.3 and R.sub.9 and R.sub.10 are CH3 or C.sub.2 H.sub.5.Type: GrantFiled: March 8, 1974Date of Patent: July 20, 1976Assignee: Cincinnati Milacron Chemicals, Inc.Inventor: Kenneth R. Molt
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Patent number: 3959220Abstract: Ultraviolet light absorbers and stabilizers, particularly for monolefin polymers, are provided from metal complexes of trivalent phosphorus compounds of the formulaeMe (L).sub.n (A).sub.m (L').sub.owhere Me is preferably nickel but can be manganese, iron, copper, molybdenum or tungsten, L is P(X)(Y)(Z) where any one or all of X, Y and Z can be O hydrocarbyl, ##EQU1## where R.sub.31 and R.sub.32 are hydrocarbyl oro hydrogen, S hydrocarbyl, hydrocarbyl, 2 or 3 of X, Y and Z can form one or more heterocyclic rings with P, A is an anion such as halogen, e.g. Cl, Br, I or F, NO.sub.3, ClO.sub.4, R.sub.33 COO.sup.- where R.sub.33 is hydrocarbyl, any hydrocarbyl group can have 1 or 2 halogen substituents, m is 0 or a small whole number, e.g. 1,2,3,4, L' is CO, NO, CN, halogen, o is zero or a small whole number, e.g. 1,2,3,4, n is 1 or another small whole number, e.g. 2,3,4, o+m+n is not greater than the highest coordination number of the metal.Type: GrantFiled: December 16, 1971Date of Patent: May 25, 1976Assignee: Cincinnati Milacron Chemicals, Inc.Inventors: Ingenuin Hechenbleikner, Thomas G. Kugele, John F. Hussar
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Patent number: RE30032Abstract: Organotin compounds are prepared having (1) at least two tin atoms linked by a bridge through sulfur, carboxylate or both and containing at least two carbon atoms in the bridge, (2) directly attached to the tin atoms one to two alkyl groups containing one to eight carbon atoms and (3) a mercaptoalkanol or derivative thereof. The compounds are useful to stabilize halogen containing vinyl and vinylidene polymers, e.g. polyvinyl chloride.Type: GrantFiled: September 7, 1978Date of Patent: June 12, 1979Assignee: Cincinnati Milacron Chemicals, Inc.Inventors: Thomas G. Kugele, Arthur F. Koeniger