US4963282A
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US
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Liquid compositions containing thiocarbamates
Assignee: Lubrizol Corp
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Filing: 1989-05-11
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Granted: 1990-10-16
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Expires: 2009-05-11
Abstract
Abstract A liquid composition is described which comprises (A) a major amount of at least one fluorine containing hydrocarbon containing one or two carbon atoms; and (B) a minor amount of at least one soluble organic lubricant comprising at least one organic thiocarbamate characterized by the formulae R.sub.1 R.sub.2 NC(X)SC(R.sub.3 R.sub.4)[C(H)(R.sub.5)].sub.a Z, or (I) [R.sub.1 R.sub.2 NC(X)SC(R.sub.3 R.sub.4)[C(H)(R.sub.5)].sub.a C(X)A].sub.2 Z' (II) wherein R 1 and R 2 are each independently lower alkyl, aryl, aralkyl or together form a heterocyclic group in which the ring is completed through the nitrogen; X is O or S; A is O, S or NR; R is H or a lower alkyl group; R 3 , R 4 and R 5 are each independently H, lower alkyl or aryl groups; a is 0 or 1; Z is --CN, --S(O)R 6 , --S(O)OR 6 , --S(O) 2 R 6 , --S(O) 2 OR 6 , or --C(O)Y; R 6 is H, alkyl or aralkyl; Y is H, --OH, --R 7 , --OR 7 , --OR 8 OH, or --NR 9 R 10 ; R 7 is an alkyl, aryl or aralkyl group; R 8 is an alkylene group of 1 to about 7 carbon atoms; R 9 and R 10 are each independently H, alkyl, hydroxyalkyl, cycloaliphatic, or together form cyclic group in which the ring is completed through the nitrogen atom; and Z' is --R 8 -- or --R 8 --A--R 8 --. Liquid compositions also are described wherein the fluorine-containing hydrocarbons also contain other halogen such as chlorine. The liquid compositions are useful particularly as refrigeration liquids in refrigerators and air-conditioners including auto, home and industrial air-conditioners.
Inventors
- 👤 Scott T. Jolley
- 👤 Betsy J. Butke
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 00:24
CPC Classifications
C; C07; C07G; C07G99/00; C07G99/002; C09; C09K; C09K5/00; C09K5/02; C09K5/04; C09K5/041; C09K5/044; C09K5/045; C10; C10M; C10M105/00; C10M105/72; C10M135/00; C10M135/12; C10M135/14; C10M135/18; C10M171/00; C10M171/008; C09K2205/00; C09K2205/24; C10M2219/00; C10M2219/06; C10M2219/062; C10M2219/066; C10N; C10N2040/00; C10N2040/30; C10N2040/32; C10N2040/34; C10N2040/36; C10N2040/38; C10N2040/40; C10N2040/42; C10N2040/44; C10N2040/50
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
230 words
A liquid composition comprising: (A) a major amount of at least one fluorine-containing hydrocarbon containing one or two carbon atoms; and (B) a minor amount of at least one soluble organic lubricant comprising at least one organic thiocarbamate characterized by the formulae R.sub.1 R.sub.2 NC(X)SC(R.sub.3 R.sub.4)[C(H)(R.sub.5)].sub.a.sup.Z,or (I) [R.sub.1 R.sub.2 NC(X)SC(R.sub.3 R.sub.4)[C(H)(R.sub.5)].sub.a C(X)A].sub.2.sup.Z' (II) wherein R 1 and R 2 are each independently lower alkyl, aryl, aralkyl or together form a heterocyclic group in which the ring is completed through the nitrogen; X is O or S; A is O, S or NR; R is H or a lower alkyl group; R 3 , R 4 and R 5 are each independently H, lower alkyl or aryl groups; a is 0 or 1; Z is --CN, --S(O)R 6 , --S(O)OR 6 , --S(O) 2 R 6 , --S(O) 2 OR 6 , or --C(O)Y; R 6 is H, alkyl or aralkyl; Y is H, --OH, --R 7 , --OR 7 , --OR 8 OH, or --NR 9 R 10 ; R 7 is an alkyl, aryl or aralkyl group; R 8 is an alkYlene group of 1 to about 7 carbon atoms; R 9 and R 10 are each independently H, alkyl, hydroxyalkyl, cycloaliphatic, or together form cyclic group in which the ring is completed through the nitrogen atom; and Z' is --R 8 -- or --R 8 --A--R 8 --.
Claim 2
Dependent Claim
230 words
A liquid composition comprising: (A) a major amount of at least one fluorine-containing hydrocarbon containing one or two carbon atoms; and (B) a minor amount of at least one soluble organic lubricant comprising at least one organic thiocarbamate characterized by the formulae R.sub.1 R.sub.2 NC(X)SC(R.sub.3 R.sub.4)[C(H)(R.sub.5)].sub.a.sup.Z,or (I) [R.sub.1 R.sub.2 NC(X)SC(R.sub.3 R.sub.4)[C(H)(R.sub.5)].sub.a C(X)A].sub.2.sup.Z' (II) wherein R 1 and R 2 are each independently lower alkyl, aryl, aralkyl or together form a heterocyclic group in which the ring is completed through the nitrogen; X is O or S; A is O, S or NR; R is H or a lower alkyl group; R 3 , R 4 and R 5 are each independently H, lower alkyl or aryl groups; a is 0 or 1; Z is --CN, --S(O)R 6 , --S(O)OR 6 , --S(O) 2 R 6 , --S(O) 2 OR 6 , or --C(O)Y; R 6 is H, alkyl or aralkyl; Y is H, --OH, --R 7 , --OR 7 , --OR 8 OH, or --NR 9 R 10 ; R 7 is an alkyl, aryl or aralkyl group; R 8 is an alkYlene group of 1 to about 7 carbon atoms; R 9 and R 10 are each independently H, alkyl, hydroxyalkyl, cycloaliphatic, or together form cyclic group in which the ring is completed through the nitrogen atom; and Z' is --R 8 -- or --R 8 --A--R 8 --.
Claim 3
Dependent Claim
17 words
The liquid composition of claim 1 wherein fluorine is the only halogen in the fluorine-containing hydrocarbon (A).
Claim 4
Dependent Claim
13 words
The liquid composition of claim 1 wherein the fluorine-containing hydrocarbon (A) is 1,1,1,2-tetrafluoroethane.
Claim 5
Dependent Claim
35 words
The liquid composition of claim 1 comprising from about 70% to about 99% by weight of the fluorine-containing hydrocarbon (A) and from about 0.1 to about 30% by weight of the soluble organic lubricant (B).
Claim 6
Dependent Claim
40 words
The liquid composition of claim 1 wherein Z in Formula I is --COOR 7 , wherein R 7 is an alkyl, or COOR 8 OH, wherein R 8 is an alkylene group containing from 1 to about 7 carbon atoms.
Claim 7
Dependent Claim
13 words
The liquid composition of claim 1 wherein X in Formula I is S.
Claim 8
Dependent Claim
26 words
The liquid composition of claim 1 wherein a is 1 and R 3 , R 4 and R 5 are hydrogen in Formulae I and II.
Claim 9
Dependent Claim
21 words
The liquid composition of claim 1 wherein, a is 0 and R 3 and R 4 are hydrogen in Formula I.
Claim 10
Dependent Claim
19 words
The liquid composition of claim 1 wherein R 1 and R 2 in Formula I are lower alkyl groups.
Claim 11
Dependent Claim
20 words
The liquid composition of claim 1 wherein the lubricant is characterized by Formula II, and Z' is --R 8 --.
Claim 12
Dependent Claim
25 words
The liquid composition of claim 1 wherein the lubricant is characterized by Formula II, and each X is S and Z' is --R 8 --.
Claim 13
Dependent Claim
169 words
The liquid composition comprising: (A) from about 70% to about 99% by weight of at least one fluorine-containing hydrocarbon containing or 1 or 2 carbon atoms; and (B) a minor amount of at least one soluble organic lubricant comprising at least one organic thiocarbamate characterized by the formula R.sub.1 R.sub.2 NC(X)SC(R.sub.3 R.sub.4)C(H)(R.sub.5)C(O)Y (IA) wherein R 1 and R 2 are each independently lower alkyl groups or together form a heterocyclic group in which the ring is completed through the nitrogen; X is O or S; R 3 , R 4 and R 5 are each independently H or lower alkyl groups; Y is H, --OH, --R 7 , --OR 7 , --OR 8 OH, or --NR 9 R 10 ; R 7 is a lower alkyl group; R 8 is an alkylene group of 1 to about 7 carbon atoms; and R 9 and R 10 are each independently H, alkyl, hydroxyalkyl, cycloaliphatic, Or together form a CyCliC group in which the ring is completed through the nitrogen atom.
Claim 14
Dependent Claim
169 words
The liquid composition comprising: (A) from about 70% to about 99% by weight of at least one fluorine-containing hydrocarbon containing or 1 or 2 carbon atoms; and (B) a minor amount of at least one soluble organic lubricant comprising at least one organic thiocarbamate characterized by the formula R.sub.1 R.sub.2 NC(X)SC(R.sub.3 R.sub.4)C(H)(R.sub.5)C(O)Y (IA) wherein R 1 and R 2 are each independently lower alkyl groups or together form a heterocyclic group in which the ring is completed through the nitrogen; X is O or S; R 3 , R 4 and R 5 are each independently H or lower alkyl groups; Y is H, --OH, --R 7 , --OR 7 , --OR 8 OH, or --NR 9 R 10 ; R 7 is a lower alkyl group; R 8 is an alkylene group of 1 to about 7 carbon atoms; and R 9 and R 10 are each independently H, alkyl, hydroxyalkyl, cycloaliphatic, Or together form a CyCliC group in which the ring is completed through the nitrogen atom.
Claim 15
Dependent Claim
17 words
The liquid composition of claim 12 wherein fluorine is the only halogen in the fluorine-containing hydrocarbon (A).
Claim 16
Dependent Claim
13 words
The liquid composition of claim 12 wherein the fluorine-containing hydrocarbon (A) is 1,1,1,2-tetrafluoroethane.
Claim 17
Dependent Claim
10 words
The liquid composition of claim 12 wherein X is sulfur.
Claim 18
Dependent Claim
19 words
The liquid composition of claim 12 wherein R 1 and R 2 in Formula IA are lower alkyl groups.
Claim 19
Dependent Claim
24 words
The liquid composition of claim 12 wherein R 3 and R 4 are hydrogen and R 5 is hydrogen or a lower alkyl group.
Claim 20
Dependent Claim
38 words
The liquid composition of claim 12 wherein Y is --OR 7 or --OR 8 OH wherein R 7 is a lower alkyl group and R 8 is an alkylene group containing from 1 to about 7 carbon atoms.
Claim 21
Dependent Claim
36 words
The liquid composition of claim 12 wherein R 1 and R 2 are lower alkyl groups, X is sulfur, R 3 and R 4 are hydrogen and R 5 is hydrogen or a lower alkyl group.
Claim 22
Dependent Claim
136 words
A liquid composition comprising: (A) from about 70% to about 99% by weight of at least one fluorine-containing hydrocarbon containing 1 or 2 carbon atoms and wherein fluorine is the only halogen present; and (B) from about 0.1% to about 30% by weight of at least one soluble organic lubricant comprising at least one organic dithiocarbamate characterized by the formula R.sub.1 R.sub.2 NC(S)SC(R.sub.3)(R.sub.4)C(H)(R.sub.5)C(O)Y (IB) wherein R 1 and R 2 are each independently lower alkyl groups; R 3 , R 4 and R 5 are each independently H or lower alkyl groups; Y is --OR 7 , --OR 8 OH, or --NR 9 R 10 ; R 7 , R 9 and R 10 are each independently lower alkyl or hydroxyalkyl groups; and R 8 is an alkylene group of 1 to about 7 carbon atoms.
Claim 23
Dependent Claim
136 words
A liquid composition comprising: (A) from about 70% to about 99% by weight of at least one fluorine-containing hydrocarbon containing 1 or 2 carbon atoms and wherein fluorine is the only halogen present; and (B) from about 0.1% to about 30% by weight of at least one soluble organic lubricant comprising at least one organic dithiocarbamate characterized by the formula R.sub.1 R.sub.2 NC(S)SC(R.sub.3)(R.sub.4)C(H)(R.sub.5)C(O)Y (IB) wherein R 1 and R 2 are each independently lower alkyl groups; R 3 , R 4 and R 5 are each independently H or lower alkyl groups; Y is --OR 7 , --OR 8 OH, or --NR 9 R 10 ; R 7 , R 9 and R 10 are each independently lower alkyl or hydroxyalkyl groups; and R 8 is an alkylene group of 1 to about 7 carbon atoms.
Claim 24
Dependent Claim
13 words
The liquid composition of claim 20 wherein the fluorine-containing hydrocarbon (A) is 1,1,1,2-tetrafluoroethane.
Claim 25
Dependent Claim
24 words
The liquid composition of claim 20 wherein R 3 and R 4 are hydrogen and R 5 is hydrogen or a lower alkyl group.
Claim 26
Dependent Claim
38 words
The liquid composition of claim 20 wherein Y is OR 7 or --OR 8 OH wherein R 7 is a lower alkyl group and R 8 is an alkylene group containing from 1 to about 7 carbon atoms.
Claim 27
Dependent Claim
301 words
A liquid composition comprising: (A) a major amount of at least one fluorine-containing hydrocarbon containing 1 or 2 carbon atoms; and (B) a minor amount of at least one soluble organic lubricant comprising at least one organic thiocarbamate derived from reactants which comprise (1) CS 2 , COS or a source material therefor; (2) an amine of the formula R.sub.1 R.sub.2 NH (III) wherein R 1 and R 2 are each independently lower alkyl, aryl, aralkyl or together form a heterocyclic group in which the ring is completed through the nitrogen; and (3) a reactant selected from reactants having the formulae R.sub.3 R.sub.4 C=C(R.sub.5)Z (IV) or R.sub.3 R.sub.4 C(X')Z (V) or [R.sub.3 R.sub.4 C=C(R.sub.5)C(X)A].sub.2 Z' (VI) or [R.sub.3 R.sub.4 C(X')C(X)A].sub.2 Z' (VII) wherein R 3 , R 4 and R 5 are each independently H or lower alkyl groups; X' is a halogen; X is O or S; A is O, S, or --NR; R is H or a lower alkyl; Z is --CN, --S(O)R 6 , --S(O)OR 6 , --S(O) 2 R 6 , --S(O) 2 OR 6 , or --C(O)Y; R 6 is H or a lower alkyl; Y is H, --OH, --R 7 , --OR 7 , --OR 8 OH, or R 7 is a lower alkyl group; R 8 is an alkylene group containing 1 to about 7 carbon atoms; R 9 and R 10 are each independently H, lower alkyl, lower hydroxyalkyl, cycloaliphatic, or together form a heterocyclic group in which the ring is completed through the nitrogen atom; Z' is --R 8 -- or --R 8 --A--R 8 --, and provided further that when reactant (3) is characterized by Formula V, the reaction is conducted in the presence of (4) a sufficient amount of at least one basic material to neutralize the HX' acid formed.
Claim 28
Dependent Claim
301 words
A liquid composition comprising: (A) a major amount of at least one fluorine-containing hydrocarbon containing 1 or 2 carbon atoms; and (B) a minor amount of at least one soluble organic lubricant comprising at least one organic thiocarbamate derived from reactants which comprise (1) CS 2 , COS or a source material therefor; (2) an amine of the formula R.sub.1 R.sub.2 NH (III) wherein R 1 and R 2 are each independently lower alkyl, aryl, aralkyl or together form a heterocyclic group in which the ring is completed through the nitrogen; and (3) a reactant selected from reactants having the formulae R.sub.3 R.sub.4 C=C(R.sub.5)Z (IV) or R.sub.3 R.sub.4 C(X')Z (V) or [R.sub.3 R.sub.4 C=C(R.sub.5)C(X)A].sub.2 Z' (VI) or [R.sub.3 R.sub.4 C(X')C(X)A].sub.2 Z' (VII) wherein R 3 , R 4 and R 5 are each independently H or lower alkyl groups; X' is a halogen; X is O or S; A is O, S, or --NR; R is H or a lower alkyl; Z is --CN, --S(O)R 6 , --S(O)OR 6 , --S(O) 2 R 6 , --S(O) 2 OR 6 , or --C(O)Y; R 6 is H or a lower alkyl; Y is H, --OH, --R 7 , --OR 7 , --OR 8 OH, or R 7 is a lower alkyl group; R 8 is an alkylene group containing 1 to about 7 carbon atoms; R 9 and R 10 are each independently H, lower alkyl, lower hydroxyalkyl, cycloaliphatic, or together form a heterocyclic group in which the ring is completed through the nitrogen atom; Z' is --R 8 -- or --R 8 --A--R 8 --, and provided further that when reactant (3) is characterized by Formula V, the reaction is conducted in the presence of (4) a sufficient amount of at least one basic material to neutralize the HX' acid formed.
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