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US4740322A
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Sulfur-containing compositions, and additive concentrates, lubricating oils, metal working lubricants and asphalt compositions containing same
Assignee: Lubrizol Corp
•
Filing: 1986-01-31
•
Granted: 1988-04-26
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Expires: 2006-01-31
Abstract
Abstract Sulfur-containing compositions are described which are prepared by sulfurizing (A) at least one fatty acid ester of a polyhydric alcohol, or (B) at least one fatty acid, fatty acid ester of a monohydric alcohol, or a mixture thereof, or (C) at least one other olefin, or (D) mixtures of any two or more of (A), (B) and (C), in the presence of a catalytic amount of (E) at least one salt of at least one dithiocarbamic acid of the formula R.sub.1 (R.sub.2)N--CSSH wherein R 1 and R 2 are each independently hydrocarbyl groups, or (F) at least one mercapto benzothiazole, or (G) mixtures of (E) and (F). Preferably, various mixtures of (A), (B) and (C) are sulfurized in accordance with the invention. The incorporation of a catalytic amount of salt of at least one dithiocarbamic acid of Formula I or at least one mercapto benzothiazole (or mixtures thereof) results in the preparation of sulfurized compositions which are characterized by excellent oil solubility and higher sulfur contents, and the compositions generally are lighter in color when compared to sulfurized compositions prepared in the absence of such catalysts. The sulfurized compositions prepared in accordance with the present invention are useful as general purpose antioxidants and friction modifiers for lubricating compositions and automatic transmission fluids and in particular, as additives in metal working lubricants. The above-described sulfurized compositions as well as sulfurized compositions prepared in the absence of catalysts (E) and/or (F) are useful in asphalt compositions.
Inventors
- 👤 Stephen A. DiBiase
- 👤 Roger L. Sowerby
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 22:29
CPC Classifications
C; C10; C10M; C10M135/00; C10M135/02; C07; C07G; C07G99/00; C07G99/002; C08; C08K; C08K5/00; C08K5/36; C10M2219/00; C10M2219/02; C10M2219/022; C10M2219/024; C10N; C10N2040/00; C10N2040/04; C10N2040/042; C10N2040/044; C10N2040/046; C10N2040/08; C10N2040/20; C10N2040/22; C10N2040/24; C10N2040/241; C10N2040/242; C10N2040/243; C10N2040/244; C10N2040/245; C10N2040/246; C10N2040/247
Claims Analysis
Total Claims: 133
Claim 1
Independent Claim
136 words
A sulfurized composition prepared by reacting in two stages, a first stage at temperatures from about 50 to about 130° C., then a second stage at temperatures from about 150 to about 350° C., a sulfurizing agent with (A) at least one fatty acid ester of a polyhydric alcohol, or (B) at least one fatty acid, fatty acid ester of a monohydric alcohol, or a mixture thereof, or (C) at least one other olefin, or (D) mixtures of any two or more of (A), (B) and (C), in the presence of a catalytic amount of (E) at least one salt of at least one dithiocarbamic acid of the formula R.sub.1 (R.sub.2)N--CSSH wherein R 1 and R 2 are each independently hydrocarbyl groups, or (F) at least one mercapto benzothiazole, or (G) mixtures of (E) and (F).
Claim 2
Dependent Claim
136 words
A sulfurized composition prepared by reacting in two stages, a first stage at temperatures from about 50 to about 130° C., then a second stage at temperatures from about 150 to about 350° C., a sulfurizing agent with (A) at least one fatty acid ester of a polyhydric alcohol, or (B) at least one fatty acid, fatty acid ester of a monohydric alcohol, or a mixture thereof, or (C) at least one other olefin, or (D) mixtures of any two or more of (A), (B) and (C), in the presence of a catalytic amount of (E) at least one salt of at least one dithiocarbamic acid of the formula R.sub.1 (R.sub.2)N--CSSH wherein R 1 and R 2 are each independently hydrocarbyl groups, or (F) at least one mercapto benzothiazole, or (G) mixtures of (E) and (F).
Claim 3
Dependent Claim
16 words
The sulfurized composition of claim 1 wherein the salt of dithiocarbamic acid (E) is metal salt.
Claim 4
Dependent Claim
15 words
The sulfurized composition of claim 1 wherein the mercapto benzothiazole (F) is a metal salt.
Claim 5
Dependent Claim
16 words
The sulfurized composition of claim 2 wherein the metal salt is a Group II metal salt.
Claim 6
Dependent Claim
22 words
The sulfurized composition of claim 1 wherein the catalyst is (F) at least one Group II metal salt of a mercapto benzothiazole.
Claim 7
Dependent Claim
12 words
The sulfurized composition of claim 1 wherein the sulfurizing agent is sulfur.
Claim 8
Dependent Claim
39 words
The sulfurized composition according to claim 1 wherein the catalyst is (E) at least one metal salt of at least one dithiocarbamic acid of the formula R.sub.1 (R.sub.2)N--CSSH wherein R 1 and R 2 are each independently hydrocarbyl groups.
Claim 9
Dependent Claim
25 words
The sulfurized composition of claim 4 wherein R 1 and R 2 are each independently alkyl groups containing from 1 to about 20 carbon atoms.
Claim 10
Dependent Claim
28 words
The sulfurized composition of claim 1 wherein the other olefin (C) is at least one aliphatic, aryl aliphatic or alicyclic olefinic hydrocarbon containing at least 3 carbon atoms.
Claim 11
Dependent Claim
32 words
The sulfurized composition of claim 1 wherein the other olefin (C) is an aliphatic olefin which may be propylene, butylene or isobutylene, and dimers, trimers, tetramers and low molecular weight polymers thereof.
Claim 12
Dependent Claim
23 words
The sulfurized composition of claim 1 wherein (C) is at least one aliphatic olefin containing from about 8 to about 36 carbon atoms.
Claim 13
Dependent Claim
14 words
The sulfurized composition of claim 1 wherein the aliphatic olefin is an aliphatic alphaolefin.
Claim 14
Dependent Claim
15 words
The sulfurized composition of claim 12 wherein the olefin is an isomerized aliphatic alpha olefin.
Claim 15
Dependent Claim
28 words
The sulfurized composition of claim 1 wherein the olefin (C) is at least one Diels-Alder adduct of at least one dienophile with at least one aliphatic conjugated diene.
Claim 16
Dependent Claim
17 words
The sulfurized composition of claim 1 wherein the other olefin (C) is at least one terpene compound.
Claim 17
Dependent Claim
45 words
The sulfurized composition of claim 1 prepared from a mixture comprising (A) about 100 parts by weight of at least one fatty acid ester of a polyhydric alcohol, and (C) from about 25 to about 400 parts by weight of at least one other olefin.
Claim 18
Dependent Claim
24 words
The sulfurized composition of claim 16 wherein the olefin is at least one aliphatic olefin containing from about 3 to about 36 carbon atoms.
Claim 19
Dependent Claim
21 words
The sulfurized composition of claim 16 wherein the mixture contains from about 25 to 100 parts by weight of olefin (C).
Claim 20
Dependent Claim
159 words
A sulfurized composition prepared by reacting in two stages, a first stage at temperatures from about 50° to about 130° C., then a second stage at temperatures from about 150° to about 350° C., a sulfurizing agent with a mixture comprising (A) about 100 parts by weight of at least one fatty acid ester of a polyhydric alcohol, (B) from about 2 to about 200 parts by weight of at least one fatty acid, fatty acid ester of a monohydric alcohol, or a mixture thereof, and optionally (C) from about 2 to about 400 parts by weight of at least one other olefin in the presence of a catalytic amount of (E) at least one salt of at least one dithiocarbamic of the formula R.sub.1 (R.sub.2)N--CSSH wherein R 1 and R 2 are each independently hydrocarbyl groups containing from 1 to about 20 carbon atoms, or (F) at least one mercapto benzothiazole, or (G) mixtures of (E) and (F).
Claim 21
Dependent Claim
159 words
A sulfurized composition prepared by reacting in two stages, a first stage at temperatures from about 50° to about 130° C., then a second stage at temperatures from about 150° to about 350° C., a sulfurizing agent with a mixture comprising (A) about 100 parts by weight of at least one fatty acid ester of a polyhydric alcohol, (B) from about 2 to about 200 parts by weight of at least one fatty acid, fatty acid ester of a monohydric alcohol, or a mixture thereof, and optionally (C) from about 2 to about 400 parts by weight of at least one other olefin in the presence of a catalytic amount of (E) at least one salt of at least one dithiocarbamic of the formula R.sub.1 (R.sub.2)N--CSSH wherein R 1 and R 2 are each independently hydrocarbyl groups containing from 1 to about 20 carbon atoms, or (F) at least one mercapto benzothiazole, or (G) mixtures of (E) and (F).
Claim 22
Dependent Claim
14 words
The sulfurized composition of claim 19 wherein the salt (E) is a metal salt.
Claim 23
Dependent Claim
14 words
The sulfurized composition of claim 19 wherein the salt (F) is a metal salt.
Claim 24
Dependent Claim
12 words
The sulfurized composition of claim 19 wherein the sulfurizing agent is sulfur.
Claim 25
Dependent Claim
36 words
The sulfurized composition of claim 19 wherein the reaction is conducted in two stages, a first stage at from about 50° to about 130° C., then a second stage at about 150° to about 200° C.
Claim 26
Dependent Claim
24 words
The sulfurized composition of claim 19 wherein the mixture contains from about 2 to about 200 parts of at least one other olefin (C).
Claim 27
Dependent Claim
21 words
The sulfurized composition of claim 19 wherein the mixture contains from about 25 to about 100 parts of the olefin (C).
Claim 28
Dependent Claim
26 words
The sulfurized composition of claim 19 wherein the other olefin (C) is at least one aliphatic olefin containing from about 3 to about 36 carbon atoms.
Claim 29
Dependent Claim
12 words
The sulfurized composition of claim 26 wherein the olefin is an alpha-olefin.
Claim 30
Dependent Claim
14 words
The sulfurized composition of claim 26 wherein the olefin (C) is an isomerized alpha-olefin.
Claim 31
Dependent Claim
17 words
The sulfurized composition of claim 26 wherein the other olefin (C) is at least one terpene compound.
Claim 32
Dependent Claim
23 words
The sulfurized composition of claim 19 wherein the mixture contains a catalytic amount of a Group II metal salt of the dithiocarbamic acid.
Claim 33
Dependent Claim
23 words
The sulfurized composition of claim 19 wherein the mixture contains a catalytic amount of a Group II metal salt of the mercapto benzothiazole.
Claim 34
Dependent Claim
16 words
The sulfurized composition of claim 19 wherein the fatty acid ester (A) is a fatty oil.
Claim 35
Dependent Claim
22 words
The sulfurized composition of claim 19 wherein the olefin (C) is an olefin containing from about 10 to about 20 carbon atoms.
Claim 36
Dependent Claim
26 words
An additive concentrate comprising a substantially inert, normally liquid diluent and from about 20 to about 90% by weight of the sulfurized composition of claim 1.
Claim 37
Dependent Claim
25 words
An additive concentrate comprising a substantially inert, normally liquid diluent and from about 20 to about 90% by weight of the composition of claim 10.
Claim 38
Dependent Claim
25 words
An additive concentrate comprising a substantially inert, normally liquid diluent and from about 20 to about 90% by weight of the composition of claim 13.
Claim 39
Dependent Claim
25 words
An additive concentrate comprising a substantially inert, normally liquid diluent and from about 20 to about 90% by weight of the composition of claim 24.
Claim 40
Dependent Claim
26 words
A lubricating oil composition comprising a major amount of an oil of lubricating viscosity and a minor, property improving amount of the composition of claim 1.
Claim 41
Dependent Claim
26 words
A lubricating oil composition comprising a major amount of an oil of lubricating viscosity and a minor, property improving amount of the composition of claim 16.
Claim 42
Dependent Claim
26 words
A lubricating oil composition comprising a major amount of an oil of lubricating viscosity and a minor, property improving amount of the composition of claim 19.
Claim 43
Dependent Claim
35 words
A method for lubricating metal during working thereof which comprises applying to said metal, a composition comprising a major amount of a lubricating oil and a minor amount of the sulfurized composition of claim 1.
Claim 44
Dependent Claim
35 words
A method for lubricating metal during working thereof which comprises applying to said metal, a composition comprising a major amount of a lubricating oil and a minor amount of the sulfurized composition of claim 16.
Claim 45
Dependent Claim
35 words
A method for lubricating metal during working thereof which comprises applying to said metal, a composition comprising a major amount of a lubricating oil and a minor amount of the sulfurized composition of claim 19.
Claim 46
Dependent Claim
19 words
The method of claim 41 wherein the composition also contains a minor amount of at least one chlorinated wax.
Claim 47
Dependent Claim
19 words
The method of claim 43 wherein the composition also contains a minor amount of at least one chlorinated wax.
Claim 48
Dependent Claim
33 words
The composition of claim 1 wherein the reaction is conducted for about 6 to about 12 hours during the first stage and for about 3 to about 6 hours during the second stage.
Claim 49
Dependent Claim
38 words
The composition of claim 46 wherein the reaction is conducted at about 130° C. during the first stage, at about 150° C. during the second stage, then is further reacted for about 3 hours at about 180° C.
Claim 50
Dependent Claim
33 words
The composition of claim 19 wherein the reaction is conducted for about 6 to about 12 hours during the first stage and for about 3 to about 6 hours during the second stage.
Claim 51
Dependent Claim
163 words
A sulfurized composition prepared by reacting in two stages, a first stage at temperatures from about 50° to about 130° C., then a second stage at temperatures from about 150° to about 350° C., a sulfurizing agent with a mixture comprising (C) about 100 parts by weight of at least one other olefin, and (B) from about 2 to about 200 parts by weight of at least one fatty acid, fatty acid ester of a monohydric alcohol, or a mixture thereof, and optionally (A) about 100 parts by weight of at least one fatty acid ester of a polyhydric alcohol, in the presence of a catalytic amount of (E) at least one salt of at least one dithiocarbamic acid of the formula R.sub.1 (R.sub.2)N--CSSH wherein R 1 and R 2 are each independently hydrocarbyl groups containing from 1 to about 20 carbon atoms, or (F) at least one metal salt of at least one mercapto benzothiazole, or (G) mixtures of (F) and (G).
Claim 52
Dependent Claim
163 words
A sulfurized composition prepared by reacting in two stages, a first stage at temperatures from about 50° to about 130° C., then a second stage at temperatures from about 150° to about 350° C., a sulfurizing agent with a mixture comprising (C) about 100 parts by weight of at least one other olefin, and (B) from about 2 to about 200 parts by weight of at least one fatty acid, fatty acid ester of a monohydric alcohol, or a mixture thereof, and optionally (A) about 100 parts by weight of at least one fatty acid ester of a polyhydric alcohol, in the presence of a catalytic amount of (E) at least one salt of at least one dithiocarbamic acid of the formula R.sub.1 (R.sub.2)N--CSSH wherein R 1 and R 2 are each independently hydrocarbyl groups containing from 1 to about 20 carbon atoms, or (F) at least one metal salt of at least one mercapto benzothiazole, or (G) mixtures of (F) and (G).
Claim 53
Dependent Claim
33 words
The composition of claim 49 wherein the reaction is conducted for about 6 to about 12 hours during the first stage and for about 3 to about 6 hours during the second stage.
Claim 54
Dependent Claim
12 words
The sulfurized composition of claim 49 wherein the sulfurizing agent is sulfur.
Claim 55
Dependent Claim
23 words
The sulfurized composition of claim 49 wherein the olefin (C) is an aliphatic olefin containing from about 8 to about 36 carbon atoms.
Claim 56
Dependent Claim
29 words
The sulfurized composition of claim 49 wherein the olefin (C) is at least one sulfurized Diels-Alder adduct of at least one dienophile with at least one aliphatic conjugated diene.
Claim 57
Dependent Claim
27 words
The composition of claim 53 wherein the dienophile comprises an alpha, beta-ethylenically unsaturated aliphatic carboxylic acid ester, carboxylic acid amide, halide, nitrile, aldehyde, ketone, or mixtures thereof.
Claim 58
Dependent Claim
85 words
The composition of claim 53 wherein the aliphatic conjugated diene corresponds to the formula ##STR7## wherein R through R 5 are each independently selected from the group consisting of hydrogen, alkyl, halo, alkoxy, alkenyl, alkenyloxy, carboxy, cyano, amino, alkylamino, dialkylamino, phenyl, and phenyl substituted with one to three substituents corresponding to R through R 5 , or R, R 2 , R 3 and R 5 are as described and R 1 and R 4 are alkylene groups joined together to form a cyclic diene.
Claim 59
Dependent Claim
31 words
The composition of claim 55 wherein R 2 and R 3 are hydrogen, and R, R 1 , R 4 and R 5 are each independently hydrogen, halo, or lower alkyl.
Claim 60
Dependent Claim
43 words
The composition of claim 54 wherein the dienophile is further characterized in that it contains at least one, but not more than two --C(O)OR 0 groups wherein R 0 is residue of a saturated aliphatic alcohol of up to about 40 carbon atoms.
Claim 61
Dependent Claim
18 words
The composition according to claim 55 wherein the diene is piperylene, isoprene, methylisoprene, chloroprene, 1,3-butadiene, or mixtures thereof.
Claim 62
Dependent Claim
11 words
The composition according to claim 58 wherein the diene is 1,3-butadiene.
Claim 63
Dependent Claim
18 words
The composition according to claim 55 wherein said dienophile is an ester of acrylic acid or methacrylic acid.
Claim 64
Dependent Claim
19 words
The sulfurized composition of claim 49 wherein the catalyst is a Group II metal salt of the dithiocarbamic acid.
Claim 65
Dependent Claim
18 words
The sulfurized composition of claim 49 wherein the catalyst is a Group II metal salt of a mercaptobenzothiazole.
Claim 66
Dependent Claim
22 words
The sulfurized composition of claim 49 wherein the fatty acid (B) is tall oil or other fatty acid mixture containing oleic acid.
Claim 67
Dependent Claim
34 words
The sulfurized composition of claim 49 wherein the amount of catalyst present is from about 0.0001 to about 5 parts by weight per 100 parts of the combined weight of (A), (B) and (C).
Claim 68
Dependent Claim
26 words
A lubricating oil composition comprising a major amount of an oil of lubricating viscosity and a minor, property improving amount of the composition of claim 49.
Claim 69
Dependent Claim
35 words
A method for lubricating metal during working thereof which comprises applying to said metal, a composition comprising a major amount of a lubricating oil and a minor amount of the sulfurized composition of claim 49.
Claim 70
Dependent Claim
19 words
The method of claim 66 wherein the composition also contains a minor amount of at least one chlorinated wax.
Claim 71
Dependent Claim
14 words
The sulfurized composition of claim 49 wherein the olefin (C) is an aliphatic alpha-olefin.
Claim 72
Dependent Claim
15 words
The sulfurized composition of claim 49 wherein the olefin (C) is an isomerized aliphatic alipha-olefin.
Claim 73
Dependent Claim
16 words
The sulfurized composition of claim 49 wherein the olefin (C) is at least one terpene compound.
Claim 74
Dependent Claim
132 words
An asphalt composition comprising a major amount of asphalt and a minor, stability improving amount of a sulfurized composition prepared by reacting at an elevated temperature, a sulfurizing agent with (A) at least one fatty acid ester of a polyhydric alcohol, or (B) at least one fatty acid ester of a monohydric alcohol, or (C) at least one other olefin selected from the group consisting of monoolefins and terpenes, or (D) mixtures of any two or more of (A), (B) and (C) optionally in the presence of a catalytic amount of (E) at least one salt of at least one dithiocarbamic acid of the formula R.sub.1 (R.sub.2)N--CSSH wherein R 1 and R 2 are each independently hydrocarbyl groups, or (F) at least one mercapto benzothiazole, or (G) mixture of (E) and (F).
Claim 75
Dependent Claim
132 words
An asphalt composition comprising a major amount of asphalt and a minor, stability improving amount of a sulfurized composition prepared by reacting at an elevated temperature, a sulfurizing agent with (A) at least one fatty acid ester of a polyhydric alcohol, or (B) at least one fatty acid ester of a monohydric alcohol, or (C) at least one other olefin selected from the group consisting of monoolefins and terpenes, or (D) mixtures of any two or more of (A), (B) and (C) optionally in the presence of a catalytic amount of (E) at least one salt of at least one dithiocarbamic acid of the formula R.sub.1 (R.sub.2)N--CSSH wherein R 1 and R 2 are each independently hydrocarbyl groups, or (F) at least one mercapto benzothiazole, or (G) mixture of (E) and (F).
Claim 76
Dependent Claim
27 words
An asphalt concrete comprising a major amount of at least one aggregate and a minor amount of asphalt cement containing a stabilized asphalt composition of claim 71.
Claim 77
Dependent Claim
17 words
The asphalt composition of claim 71 wherein the salt of dithiocarbamic acid (E) is a metal salt.
Claim 78
Dependent Claim
15 words
The asphalt composition of claim 71 wherein the mercapto benzothiazole (F) is a metal salt.
Claim 79
Dependent Claim
16 words
The asphalt composition of claim 73 wherein the metal salt is a Group II metal salt.
Claim 80
Dependent Claim
21 words
The asphalt composition of claim 71 wherein the catalyst is (F) at least one Group II metal salt of mercapto benzothiazole.
Claim 81
Dependent Claim
38 words
The asphalt composition of claim 71 wherein the sulfurizing agent comprises at least one member of the group consisting of elemental sulfur, hydrogen sulfide, sulfur halide and sodium sulfide, and a mixture of hydrogen sulfide and sulfur dioxide.
Claim 82
Dependent Claim
12 words
The asphalt composition of claim 71 wherein the sulfurizing agent comprises sulfur.
Claim 83
Dependent Claim
22 words
The asphalt composition of claim 71 wherein the reaction is conducted at a temperature of from about 50° to about 350° C.
Claim 84
Dependent Claim
14 words
The asphalt composition of claim 78 wherein the sulfurizing agent further comprises hydrogen sulfide.
Claim 85
Dependent Claim
26 words
The asphalt composition of claim 71 wherein the (C) is at least one aliphatic, aryl aliphatic or alicyclic olefinic hydrocarbon containing at least 3 carbon atoms.
Claim 86
Dependent Claim
30 words
The asphalt composition of claim 71 wherein the (C) is an aliphatic olefin which may be propylene, butylene or isobutylene, and dimers, trimers, tetramers and low molecular weight polymers thereof.
Claim 87
Dependent Claim
23 words
The asphalt composition of claim 71 wherein (C) is at least one aliphatic olefin containing from about 8 to about 36 carbon atoms.
Claim 88
Dependent Claim
13 words
The asphalt composition of claim 71 wherein the monoolefin is an aliphatic alpha-olefin.
Claim 89
Dependent Claim
15 words
The asphalt composition of claim 79 wherein the monoolefin is an isomerized aliphatic alpha olefin.
Claim 90
Dependent Claim
27 words
The asphalt composition of claim 71 wherein the (C) is at least one Diels-Alder adduct of at least one dienophile with at least one aliphatic conjugated diene.
Claim 91
Dependent Claim
15 words
The asphalt composition of claim 71 wherein the (C) is at least one terpene compound.
Claim 92
Dependent Claim
50 words
The asphalt composition of claim 71 wherein the sulfurized composition is prepared from a mixture comprising (A) about 100 parts by weight of at least one fatty acid ester of a polyhydric alcohol, and (C) from about 0 to about 400 parts by weight of at least one other olefin.
Claim 93
Dependent Claim
23 words
The composition of claim 83 wherein the olefin is at least one aliphatic olefin containing from about 3 to about 36 carbon atoms.
Claim 94
Dependent Claim
21 words
The asphalt composition of claim 83 wherein the mixture contains from about 25 to 100 parts by weight of olefin (C).
Claim 95
Dependent Claim
152 words
An asphalt composition comprising a major amount of an asphalt and a minor, stability improving amount of a sulfurized composition prepared by reacting at an elevated temperature, a sulfurizing agent with a mixture comprising (A) about 100 parts by weight of at least one fatty acid ester of a polyhydric alcohol, (B) from about 0 to about 200 parts by weight of at least one fatty acid, fatty acid ester of a monohydric alcohol, or a mixture thereof, and (C) from about 0 to about 400 parts by weight of at least one other olefin in the presence of a catalytic amount of (E) at least one salt of at least one dithiocarbamic acid of the formula R.sub.1 (R.sub.2)N--CSSH wherein R 1 and R 2 are each independently hydrocarbyl groups containing from 1 to about 20 carbon atoms, or (F) at least one mercapto benzothiazole, or (G) mixtures of (E) and (F).
Claim 96
Dependent Claim
152 words
An asphalt composition comprising a major amount of an asphalt and a minor, stability improving amount of a sulfurized composition prepared by reacting at an elevated temperature, a sulfurizing agent with a mixture comprising (A) about 100 parts by weight of at least one fatty acid ester of a polyhydric alcohol, (B) from about 0 to about 200 parts by weight of at least one fatty acid, fatty acid ester of a monohydric alcohol, or a mixture thereof, and (C) from about 0 to about 400 parts by weight of at least one other olefin in the presence of a catalytic amount of (E) at least one salt of at least one dithiocarbamic acid of the formula R.sub.1 (R.sub.2)N--CSSH wherein R 1 and R 2 are each independently hydrocarbyl groups containing from 1 to about 20 carbon atoms, or (F) at least one mercapto benzothiazole, or (G) mixtures of (E) and (F).
Claim 97
Dependent Claim
27 words
An asphalt concrete comprising a major amount of at least one aggregate and a minor amount of asphalt cement containing a stabilized asphalt composition of claim 91.
Claim 98
Dependent Claim
13 words
The composition of claim 91 wherein the salt (E) is a metal salt.
Claim 99
Dependent Claim
14 words
The asphalt composition of claim 91 wherein the salt (F) is a metal salt.
Claim 100
Dependent Claim
12 words
The asphalt composition of claim 91 wherein the sulfurizing agent is sulfur.
Claim 101
Dependent Claim
23 words
The asphalt composition according to claim 90 wherein the reaction is conducted at a temperature of from about 50° to about 350° C.
Claim 102
Dependent Claim
22 words
The asphalt composition of claim 91 wherein the reaction is conducted at a temperature of from aboout 50° to about 200° C.
Claim 103
Dependent Claim
24 words
The asphalt composition of claim 91 wherein the mixture contains from about 2 to about 200 parts of at least one other olefin (C).
Claim 104
Dependent Claim
21 words
The asphalt composition of claim 91 wherein the mixture contains from about 25 to about 100 parts of the olefin (C).
Claim 105
Dependent Claim
26 words
The asphalt composition of claim 91 wherein the other olefin (C) is at least one aliphatic olefin containing from about 3 to about 36 carbon atoms.
Claim 106
Dependent Claim
12 words
The asphalt composition of claim 100 wherein the olefin is an alpha-olefin.
Claim 107
Dependent Claim
14 words
The asphalt composition of claim 100 wherein the olefin (C) is an isomerized alpha-olefin.
Claim 108
Dependent Claim
17 words
The asphalt composition of claim 100 wherein the other olefin (C) is at least one terpene compound.
Claim 109
Dependent Claim
31 words
The asphalt composition of claim 91 wherein the mixture contains a sulfurized composition prepared in the presence of a catalytic amount of a Group II metal salt of the dithiocarbamic acid.
Claim 110
Dependent Claim
31 words
The asphalt composition of claim 91 wherein the mixture contains a sulfurized composition prepared in the presence of a catalytic amount of a Group II metal salt of the mercapto benzothiazole.
Claim 111
Dependent Claim
16 words
The asphalt composition of claim 91 wherein the fatty acid ester (A) is a fatty oil.
Claim 112
Dependent Claim
22 words
The asphalt composition of claim 91 wherein the olefin (C) is an olefin containing from about 10 to about 20 carbon atoms.
Claim 113
Dependent Claim
156 words
An asphalt composition comprising a major amount of asphalt and a minor, stability improving amount of a sulfurized composition prepared by reacting at an elevated temperature, a sulfurizing agent with a mixture comprising (A) from about 0 to 100 parts by weight of at least one fatty acid ester of a polyhydric alcohol, (B) from about 0 to about 200 parts by weight of at least one fatty acid, fatty acid ester of a monohydric alcohol, or a mixture thereof, and (C) about 100 parts by weight of at least one other olefin, in the presence of a catalytic amount of (E) at least one salt of at least one dithiocarbamic acid of the formula R.sub.1 (R.sub.2)N--CSSH wherein R 1 and R 2 are each independently hydrocarbyl groups containing from 1 to about 20 carbon atoms, or (F) at least one metal salt of at least one mercapto benzothiazole, or (G) mixtures of (E) and (F).
Claim 114
Dependent Claim
156 words
An asphalt composition comprising a major amount of asphalt and a minor, stability improving amount of a sulfurized composition prepared by reacting at an elevated temperature, a sulfurizing agent with a mixture comprising (A) from about 0 to 100 parts by weight of at least one fatty acid ester of a polyhydric alcohol, (B) from about 0 to about 200 parts by weight of at least one fatty acid, fatty acid ester of a monohydric alcohol, or a mixture thereof, and (C) about 100 parts by weight of at least one other olefin, in the presence of a catalytic amount of (E) at least one salt of at least one dithiocarbamic acid of the formula R.sub.1 (R.sub.2)N--CSSH wherein R 1 and R 2 are each independently hydrocarbyl groups containing from 1 to about 20 carbon atoms, or (F) at least one metal salt of at least one mercapto benzothiazole, or (G) mixtures of (E) and (F).
Claim 115
Dependent Claim
27 words
An asphalt concrete comprising a major amount of at least one aggregate and a minor amount of asphalt cement containing a stabilized asphalt composition of claim 108.
Claim 116
Dependent Claim
12 words
The asphalt composition of claim 108 wherein the sulfurizing agent is sulfur.
Claim 117
Dependent Claim
22 words
The asphalt composition of claim 108 wherein the reaction is conducted at a temperature of from about 50° to about 350° C.
Claim 118
Dependent Claim
23 words
The asphalt composition of claim 108 wherein the olefin (C) is an aliphatic olefin containing from about 8 to about 36 carbon atoms.
Claim 119
Dependent Claim
29 words
The asphalt composition of claim 108 wherein the olefin (C) is at least one sulfurized Diels-Alder adduct of at least one dienophile with at least one aliphatic conjugated diene.
Claim 120
Dependent Claim
27 words
The asphalt composition of claim 113 wherein the dienophile comprises an alpha,beta-ethylenically unsaturated aliphatic carboxylic acid ester, carboxylic acid amide, halide, nitrile, aldehyde, ketone, or mixtures thereof.
Claim 121
Dependent Claim
86 words
The asphalt composition of claim 113 wherein the aliphatic conjugated diene corresponds to the formula ##STR8## wherein R through R 5 are each independently selected from the group consisting of hydrogen, alkyl, halo, alkoxy, alkenyl, alkenyloxy, carboxy, cyano, amino, alkylamino, dialkylamino, phenyl, and phenyl substituted with one to three substituents corresponding to R through R 5 , or R, R 2 , R 3 and R 5 are as described and R 1 and R 4 are alkylene groups joined together to form a cyclic diene.
Claim 122
Dependent Claim
32 words
The asphalt composition of claim 115 wherein R 2 and R 3 are hydrogen, and R, R 1 , R 4 and R 5 are each indepen-dently hydrogen, halo, or lower alkyl.
Claim 123
Dependent Claim
44 words
The asphalt composition of claim 108 wherein the dienophile is further characterized in that it contains at least one, but not more than two --C(O)OR 0 groups wherein R 0 is residue of a saturated aliphatic alcohol of up to about 40 carbon atoms.
Claim 124
Dependent Claim
19 words
The asphalt composition according to claim 113 wherein the diene is piperylene, isoprene, methylisoprene, chloroprene, 1,3-butadiene, or mixtures thereof.
Claim 125
Dependent Claim
12 words
The asphalt composition according to claim 118 wherein the diene is 1,3-butadiene.
Claim 126
Dependent Claim
19 words
The asphalt composition according to claim 117 wherein said dienophile is an ester of acrylic acid or methacrylic acid.
Claim 127
Dependent Claim
19 words
The asphalt composition of claim 108 wherein the catalyst is a Group II metal salt of the dithiocarbamic acid.
Claim 128
Dependent Claim
18 words
The asphalt composition of claim 108 wherein the catalyst is a Group II metal salt of a mercaptobenzothiazole.
Claim 129
Dependent Claim
22 words
The asphalt composition of claim 108 wherein the fatty acid (B) is tall oil or other fatty acid mixture containing oleic acid.
Claim 130
Dependent Claim
34 words
The asphalt composition of claim 108 wherein the amount of catalyst present is from about 0.0001 to about 5 parts by weight per 100 parts of the combined weight of (A), (B) and (C).
Claim 131
Dependent Claim
14 words
The asphalt composition of claim 108 wherein the olefin (C) is an aliphatic alpha-olefin.
Claim 132
Dependent Claim
15 words
The asphalt composition of claim 108 wherein the olefin (C) is an isomerized aliphatic alpha-olefin.
Claim 133
Dependent Claim
16 words
The asphalt composition of claim 108 wherein the olefin (C) is at least one terpene compound.
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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) | 1991-04-26 | 1991-10-26 | 1992-04-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-04-26 | 1995-10-26 | 1996-04-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-04-26 | 1999-10-26 | 2000-04-26 | $7700.00 | Window Closed / Lapsed |