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US4404302A Expired / Lapsed US ⏱️ 0.0 years remaining

Acylated hindered hexahydropyrimidines and their use as light stabilizing agents

Assignee: Vibrantz Corp
•
Filing: 1982-05-27
•
Granted: 1983-09-13
•
Expires: 2002-05-27
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Abstract

Abstract An acylated, hindered hexahydropyrimidine of the formula ##STR1## wherein R 1 , R 2 , R 3 and R 4 may be the same or different independently of each other and are alkyl having 1 to 6 carbon atoms, when unsubstituted, or alkyl or aryl substituted; R 5 and R 6 may be the same or different and are hydrogen, or alkyl; R 7 is selected from the group consisting of: alkyl having 1 to 20 carbon atoms, substituted alkyl where the alkyl without substitution has 1 to 20 carbon atoms and where substituents may be up to five lower alkyl groups, arylalkyl, cycloalkyl having 3 to 12 carbon atoms, aryl aryl substituted with 1 to 3 substituents seleted from the group consisting of: lower alkyl, lower alkoxy, and hydroxyl; ##STR2## wherein R 9 is unsubstituted or substituted with alkyl, R 10 is hydroxyl, lower alkoxy, phenoxy and the group ##STR3## and R 8 is hydrogen, alkyl, substituted alkyl, arylalkyl, hydroxyl, oxyl and ##STR4## wherein R 11 is unsubstituted or substituted alkyl.

Inventors

  • 👤 Goutam Gupta
  • 👤 Chester E. Ramey

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 23:45
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/06; C07D239/04; C07D239/70; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08K5/3442; C08K5/3462

Claims Analysis

Total Claims: 48
Claim 1
Independent Claim 509 words
An acylated, hindered hexahydropyrimidine of the formula ##STR25## wherein R 1 , R 2 , R 3 and R 4 may be the same or different independently of each other and are selected from the group consisting of: alkyl having 1 to 6 carbon atoms, when unsubstituted, or substituted with one methyl, ethyl, or phenyl group, aryl, and aryl substituted with 1 to 3 substituents selected from the group consisting of lower alkyl, lower alkoxy, and hydroxyl, and wherein R 1 together with R 2 , and R 3 together with R 4 , each taken together with the respective ring carbon to which they are attached, may form respectively a cycloalkyl of ring size from 4 to 7 carbons; R 5 and R 6 may be the same or different and are selected from the group consisting of hydrogen, and alkyl having 1 to 6 carbon atoms, and arylalkyl, and R 5 together with R 6 and the two ring carbons to which they are attached respectively may form a cycloalkyl group of ring size from 5 to 7 carbon atoms; R 7 is selected from the group consisting of: alkyl having 1 to 20 carbon atoms, substituted alkyl where the alkyl without substitution has 1 to 20 carbon atoms and where substituents may be up to five lower alkyl groups, arylalkyl, cycloalkyl having 3 to 12 carbon atoms, aryl, aryl substituted with 1 to 3 substituents selected from the group consisting of: lower alkyl, lower alkoxy, and hydroxyl; ##STR26## wherein R 9 is selected from the group consisting of alkyl having 1 to 20 carbon atoms unsubstituted, or substituted with up to 5 lower alkyl groups, and cycloalkyl having 5 to 11 carbons and phenyl; wherein A is: alkylene of 1 to 12 carbons; alkylene substituted with alkyl or alkenyl to have a total of up to 18 carbons; alkenylene of 2 to 4 carbons; cycloalkylene of up to 12 carbon atoms; cycloalkenylene of up to 12 carbon atoms; bicycloalkylene up to 8 carbon atoms; bicycloalkenylene up to 8 carbon atoms; or phenylene, and wherein R 10 is selected from the group consisting of hydroxyl, lower alkoxy, phenoxy and the group ##STR27## wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined above, and R 8 is selected from the group consisting of hydrogen, alkyl having 1 to 10 carbon atoms, substituted alkyl having 1 to 10 carbon atoms, arylalkyl, hydroxyl, oxyl and ##STR28## wherein R 11 is selected from the group consisting of alkyl having 1 to 20 carbon atoms unsubstituted, or substituted with up to five lower alkyl groups wherein the substitution in substituted alkyl consists of from 1 to 3 substituent alkyl groups of up to 18 carbons each, which substituent groups may be the same or different, and wherein the substitution in substituted aryl consists of from 1 to 3 substituent groups that may be the same or different and that are selected from the group consisting of hydroxyl and lower alkyl.
Claim 2
Dependent Claim 509 words
An acylated, hindered hexahydropyrimidine of the formula ##STR25## wherein R 1 , R 2 , R 3 and R 4 may be the same or different independently of each other and are selected from the group consisting of: alkyl having 1 to 6 carbon atoms, when unsubstituted, or substituted with one methyl, ethyl, or phenyl group, aryl, and aryl substituted with 1 to 3 substituents selected from the group consisting of lower alkyl, lower alkoxy, and hydroxyl, and wherein R 1 together with R 2 , and R 3 together with R 4 , each taken together with the respective ring carbon to which they are attached, may form respectively a cycloalkyl of ring size from 4 to 7 carbons; R 5 and R 6 may be the same or different and are selected from the group consisting of hydrogen, and alkyl having 1 to 6 carbon atoms, and arylalkyl, and R 5 together with R 6 and the two ring carbons to which they are attached respectively may form a cycloalkyl group of ring size from 5 to 7 carbon atoms; R 7 is selected from the group consisting of: alkyl having 1 to 20 carbon atoms, substituted alkyl where the alkyl without substitution has 1 to 20 carbon atoms and where substituents may be up to five lower alkyl groups, arylalkyl, cycloalkyl having 3 to 12 carbon atoms, aryl, aryl substituted with 1 to 3 substituents selected from the group consisting of: lower alkyl, lower alkoxy, and hydroxyl; ##STR26## wherein R 9 is selected from the group consisting of alkyl having 1 to 20 carbon atoms unsubstituted, or substituted with up to 5 lower alkyl groups, and cycloalkyl having 5 to 11 carbons and phenyl; wherein A is: alkylene of 1 to 12 carbons; alkylene substituted with alkyl or alkenyl to have a total of up to 18 carbons; alkenylene of 2 to 4 carbons; cycloalkylene of up to 12 carbon atoms; cycloalkenylene of up to 12 carbon atoms; bicycloalkylene up to 8 carbon atoms; bicycloalkenylene up to 8 carbon atoms; or phenylene, and wherein R 10 is selected from the group consisting of hydroxyl, lower alkoxy, phenoxy and the group ##STR27## wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined above, and R 8 is selected from the group consisting of hydrogen, alkyl having 1 to 10 carbon atoms, substituted alkyl having 1 to 10 carbon atoms, arylalkyl, hydroxyl, oxyl and ##STR28## wherein R 11 is selected from the group consisting of alkyl having 1 to 20 carbon atoms unsubstituted, or substituted with up to five lower alkyl groups wherein the substitution in substituted alkyl consists of from 1 to 3 substituent alkyl groups of up to 18 carbons each, which substituent groups may be the same or different, and wherein the substitution in substituted aryl consists of from 1 to 3 substituent groups that may be the same or different and that are selected from the group consisting of hydroxyl and lower alkyl.
Claim 3
Dependent Claim 30 words
An acylated, hindered hexahydropyrimidine salt according to claim 1 comprising a nickel, cobalt, or barium salt of the acylated hexahydropyrimidine where R 10 is hydroxyl before formation of the salt.
Claim 4
Dependent Claim 285 words
An acylated, hindered hexahydropyrimidine according to claim 1 wherein R 1 , R 2 , R 3 , and R 4 may be the same or different and are selected from the group consisting of alkyl having 1 to 6 carbon atoms, and R 1 together with R 2 , and R 3 together with R 4 , each taken together with the respective ring carbon to which they are attached, may form respectively a cycloalkyl group of 5 to 6 carbons; R 5 and R 6 may be the same or different and are selected from the group consisting of hydrogen and alkyl having 1 to 6 carbon atoms, and R 5 together with R 6 and the two ring carbons to which they are attached respectively may form a cycloalkyl group having 5 to 6 carbons; R 7 is selected from the group consisting of alkyl having 1 to 20 carbon atoms, substituted alkyl where the alkyl without substitution has 1 to 20 carbon atoms and where the substituents may be up to five lower alkyl groups, arylalkyl, aryl, aryl substituted with 1 to 3 substituents selected from the group consisting of lower alkyl; lower alkoxy, and hydroxyl; --OR 9 , --NHR 9 , the group --(CH 2 ) n COR 10 where n is 1 to 20, and ##STR29## wherein R 9 is selected from the group consisting of alkyl having 1 to 20 carbon atoms and phenyl, and R 8 is selected from the group consisting of hydrogen, lower alkyl, hydroxyl, oxyl and ##STR30## wherein R 11 is selected from the group consisting of alkyl having 1 to 20 carbon atoms unsubstituted, or substituted with up to five lower alkyl groups.
Claim 5
Dependent Claim 132 words
An acylated hindered hexahydropyrimidine according to claim 1 wherein each of R 1 , R 2 , R 3 , R 4 and R 6 is methyl, R 5 is hydrogen, R 7 is selected from the group consisting of: alkyl having 1 to 20 carbon atoms unsubstituted, or substituted with up to five lower alkyl groups, aryl, aryl substituted with 1 to 3 substituents selected from the group consisting of lower alkyl, lower alkoxy, and hydroxyl, --OR 9 , --NHR 9 and the group --CH 2 COR 10 , wherein R 9 is selected from the group consisting of alkyl having 1 to 20 carbon atoms and phenyl, and R 10 is the group ##STR31## wherein R 12 is selected from the group consisting of hydrogen, lower alkyl, hydroxyl and oxyl.
Claim 6
Dependent Claim 15 words
An acylated hindered hexahydropyrimidine according to claim 1 wherein the compound has the formula ##STR32##
Claim 7
Dependent Claim 15 words
An acylated hindered hexahydropyrimidine according to claim 1 wherein the compound has the formula ##STR33##
Claim 8
Dependent Claim 15 words
An acylated hindered hexahydropyrimidine according to claim 1 wherein the compound has the formula ##STR34##
Claim 9
Dependent Claim 15 words
An acylated hindered hexahydropyrimidine according to claim 1 wherein the compound has the formula ##STR35##
Claim 10
Dependent Claim 15 words
An acylated hindered hexahydropyrimidine according to claim 1 wherein the compound has the formula ##STR36##
Claim 11
Dependent Claim 29 words
A synthetic polymeric composition comprising an amount effective as a light stabilizer of an acylated, hindered hexahydropyrimidine according to claim 1, 2, 3, 4, 5, 6, 7, or 8.
Claim 12
Dependent Claim 78 words
A polymeric composition containing a light stabilizing amount of an acylated hindered hexahydropyrimidine according to claim 9 wherein the polymer comprises a homopolymer of a vinyl halide, a copolymer of a vinyl halide with at least one other polymerizable unsaturated compound, a homopolymer of an alpha olefin, a copolymer of alpha olefins, a polydiene, a polyurethane, a polyamide, a polycarbonate, a polyacetal, polystyrene, acrylonitrile-butadiene-styrene, a copolymer of a vinyl halide with an olefin, or copolymers or mixtures thereof.
Claim 13
Dependent Claim 23 words
A polymeric composition containing a light stabilizing amount of an acylated hindered hexahydropyrimidine according to claim 11 wherein the polymer is a polyα-olefin.
Claim 14
Dependent Claim 37 words
A polymeric composition containing a light stabilizing amount of an acylated hindered hexahydropyrimidine according to claim 3 wherein the polymer is selected from the group consisting of polymers and copolymers of ethylene, propylene, butene, and mixtures thereof.
Claim 15
Dependent Claim 23 words
A polymeric composition containing a light stabilizing effective amount of an acylated hindered hexahydropyrimidine according to claim 13 wherein the polymer is polypropylene.
Claim 16
Dependent Claim 30 words
A method of light stabilizing polymeric compositions by incorporating therein an effective amount of an acylated hindered hexahydropyrimidine according to claim 1, 2, 3, 4, 5, 6, 7, or 8.
Claim 17
Dependent Claim 54 words
A method of light stabilizing a polymeric composition selected from the group consisting of polyvinyl chloride, polyα-olefins, polydienes, polyurethanes, polyamides, polycarbonates, polyacetals, polystyrene, acrylonitrile-butadiene-styrene and copolymers of vinyl halides with olefins, by incorporating therein an effective amount of an acylated hindered hexahydropyrimidine according to claim 1, 2, 3, 4, 5, 6, 7, or 8.
Claim 18
Dependent Claim 19 words
A method of light stabilizing a polymeric composition in accordance with claim 15 wherein the polymer is a polyα-olefin.
Claim 19
Dependent Claim 30 words
A method of light stabilizing a polymeric composition in accordance with claim 17 wherein the polymer is selected from the group consisting of polymers and copolymers of propylene and butene.
Claim 20
Dependent Claim 21 words
A method of light stabilizing a polymeric composition in accordance with claim 17 wherein the polymer is a polymer of propylene.
Claim 21
Dependent Claim 2 words
1-(alkanoyl)2,2,4,4,6-pentamethyl hyexahydropyrimidine.
Claim 22
Dependent Claim 2 words
1-(alkanoyl)2,2,4,4,6-pentamethyl hyexahydropyrimidine.
Claim 23
Dependent Claim 2 words
1-(stearoyl)2,2,4,4,6-pentamethyl hexahydropyrimidine.
Claim 24
Dependent Claim 2 words
1-(stearoyl)2,2,4,4,6-pentamethyl hexahydropyrimidine.
Claim 25
Dependent Claim 2 words
1-(propionyl)2,2,4,4,6-pentamethyl hexahydropyrimidine.
Claim 26
Dependent Claim 2 words
1-(propionyl)2,2,4,4,6-pentamethyl hexahydropyrimidine.
Claim 27
Dependent Claim 3 words
1-(cyclohexane carbonyl)2,2,4,4,6-pentamethyl hexahydropyrimidine.
Claim 28
Dependent Claim 3 words
1-(cyclohexane carbonyl)2,2,4,4,6-pentamethyl hexahydropyrimidine.
Claim 29
Dependent Claim 3 words
1,1'-alkanoyl bis(2,2,4,4,6-pentamethyl hexahydropyrimidine).
Claim 30
Dependent Claim 3 words
1,1'-alkanoyl bis(2,2,4,4,6-pentamethyl hexahydropyrimidine).
Claim 31
Dependent Claim 3 words
1,1'-sebacoyl bis(2,2,4,4,6-pentamethyl hexahydropyrimidine).
Claim 32
Dependent Claim 3 words
1,1'-sebacoyl bis(2,2,4,4,6-pentamethyl hexahydropyrimidine).
Claim 33
Dependent Claim 1 words
14-n-alkanoyl-15,16-tetramethylene-7,14-diazaspiro[5.1.5.3]hexadecane.
Claim 34
Dependent Claim 1 words
14-n-alkanoyl-15,16-tetramethylene-7,14-diazaspiro[5.1.5.3]hexadecane.
Claim 35
Dependent Claim 3 words
3-carboxy[2,2,4,4,6-pentamethylhexahydropyrimidin-1-yl]amino methyl-1-carboxy[2,2,4,4,6-pentamethylhexahydropyrimidin-1-yl]amino-3,3,5-trimethyl cyclohexane.
Claim 36
Dependent Claim 3 words
3-carboxy[2,2,4,4,6-pentamethylhexahydropyrimidin-1-yl]amino methyl-1-carboxy[2,2,4,4,6-pentamethylhexahydropyrimidin-1-yl]amino-3,3,5-trimethyl cyclohexane.
Claim 37
Dependent Claim 3 words
A 1-(3,5-benzyl)-2,2,4,4,6-pentamethyl hexahydropyrimidine.
Claim 38
Dependent Claim 3 words
A 1-(3,5-benzyl)-2,2,4,4,6-pentamethyl hexahydropyrimidine.
Claim 39
Dependent Claim 12 words
A compound of claim 28 wherein the benzoyl is a di-t-butyl-4-hydroxy benzoyl.
Claim 40
Dependent Claim 17 words
The reaction product of a dibasic carboxylic acid or dibasic carboxylic acid anhydride with a hindered hexahydropyrimidine.
Claim 41
Dependent Claim 17 words
The reaction product of a dibasic carboxylic acid or dibasic carboxylic acid anhydride with a hindered hexahydropyrimidine.
Claim 42
Dependent Claim 12 words
A product of claim 30 wherein the acid anhydride is succinic anhydride.
Claim 43
Dependent Claim 12 words
A product of claim 31 wherein the hindered hexahydropyrimidine is 2,2,4,4,6-pentamethyl hexahydropyrimidine.
Claim 44
Dependent Claim 15 words
The nickel, cobalt or barium salt of the product of claim 30, 31 or 32.
Claim 45
Dependent Claim 3 words
1-(alkylamino carbonyl)2,2,4,4,6-pentamethyl hexahydropyrimidine.
Claim 46
Dependent Claim 3 words
1-(alkylamino carbonyl)2,2,4,4,6-pentamethyl hexahydropyrimidine.
Claim 47
Dependent Claim 3 words
1-(octadecylamino carbonyl)2,2,4,4,6-pentamethyl hexahydropyrimidine.
Claim 48
Dependent Claim 3 words
1-(octadecylamino carbonyl)2,2,4,4,6-pentamethyl hexahydropyrimidine.

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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-09-12 1987-03-14 1987-09-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-09-12 1991-03-14 1991-09-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-09-12 1995-03-14 1995-09-13 $7700.00 Window Closed / Lapsed

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