Zero volatile organic compound compositions based upon organic solvents which are negligibly reactive with hydroxyl radical and do not contribute appreciably to the formation of ground based ozone

• US 6,048,471 A
• Filed: 02/12/1998
• Issued: 04/11/2000
• Est. Priority Date: 07/18/1997
• Status: Expired due to Fees

• Current Assignee: Polymer Solvents LLC
• Original Assignee: Richard G. Henry
• Inventors: Henry, Richard G.
• Primary Examiner(s): Kelly, C. H.
• Assistant Examiner(s): CROSS, LATOYA I
• Application Number:
  US09/022,779
• Time in Patent Office: 789 Days
• Field of Search: 252/364, 510/382, 106/236
• US Class Current: 252/364
• CPC Class Codes: C08G 18/0852 the solvents being organic
• CPC Class Codes: C08J 3/091 characterised by the chemical constitution of the organic liquid
• CPC Class Codes: C09D 11/033 characterised by the solvent
• CPC Class Codes: C09D 7/20 Diluents or solvents

Abstract

Environmentally-safer resin-solvent compositions are provided which are generally free of volatile organic compounds (VOCs). The solvent and resin-solvent compositions may replace high-VOC hydrocarbon solvents for use in inks, coatings, adhesives and the like. These novel compositions are negligibly reactive with hydroxyl radicals and therefore are able to reach higher into the atmosphere before decomposing.

Claims

1. A solvent-resin composition consisting essentially of a resin component and a solvent component, the solvent component being 5-95% by total volume of the solvent-resin composition, the solvent component being one or more zero-VOC, non-ground based ozone forming solvents selected from the group consisting of:

1) chlorobromomethane;

2) 1-bromopropane;

3) methyl acetate;

4) n-alkane (C12-C18);

5) t-butyl acetate;

6) perchloroethylene;

7) benzotrifluoride;

8) parachlorobenzotrifluoride;

9) acetone;

10) 1,2-dichloro-1,1,2-trifluoroethane

11) dimethoxymethane;

12) 1,1,1,2,2,3,3,4,4-nonafluoro-4-methoxy-butane;

13) 2-(difluoromethoxymethyl)-1,1,1,2,3,3,3-heptafluoropropane;

14) 1-ethoxy-1,1,2,2,3,3,4,4,4-nonafluorobutane;

15) 2-(ethoxydifluoromethyl)-1,1,1,2,3,3,3-heptafluoropropane;

16) methylene chloride; and

,

17) technical white oils (mineral oils).

2. The composition according to claim 1 wherein the solvent component is present in the amount 40-95% by total volume of the composition.

3. The composition according to claim 2 for use as an adhesive wherein the solvent component is present in the amount 30-80% by total volume of the composition.

4. The composition according to claim 2 for use as an ink wherein the solvent component is present in the amount 70-95% by total volume of the composition.

5. The composition according to claim 1 wherein the solvent component is present in the amount 10-90%, by total volume of the composition, and is a mixture of at least two solvents wherein at least one solvent is selected from the group consisting of:

chlorobromomethane;

1-bromopropane;

methyl acetate;

n-alkane (C12-C18);

t-butyl acetate;

perchloroethylene;

benzotrifluoride;

parachlorobenzotrifluoride;

acetone;

1,2-dichloro-1,1,2-trifluoroethane;

dimethoxymethane; and

methylene chloride.

6. The composition according to claim 1 wherein the solvent component is present in the amount 10-95% by total volume of the composition, the solvent component consisting essentially of methyl acetate and at least one additional solvent selected from the group consisting of:

chlorobromomethane;

1-bromopropane;

n-alkane (C12-C18);

t-butyl acetate;

perchloroethylene;

benzotrifluoride;

parachlorobenzotrifluoride;

acetone;

1,2-dichloro-1,1,2-trifluoroethane;

dimethoxymethane;

1,1,1,2,2,3,3,4,4,-nonafluoro-4-methoxy-butane;

2-(difluoromethoxymethyl)-1,1,1,2,3,3,3-heptafluoropropane;

1-ethoxy-1,1,2,2,3,3,4,4,4-nonafluorobutane; and

,

2-(ethoxydifluoromethyl)-1,1,1,2,3,3,3-heptafluoropropane.

7. The composition according to claim 1 wherein the solvent component, expressed in terms of % by total volume of the composition, is selected from the group consisting of:

1) 10-90% benzotrifluoride and 90-10% of one or more of the solvents;

a) 1,1,1,2,2,3,3,4,4-nonafluoro-4-methoxy-butane;

b) 2-(difluoromethoxymethyl)-1,1,1,2,3,3,3,-heptafluoropropane;

c) 1-ethoxy-1,1,2,2,3,3,4,4,4-nonafluorobutane;

d) 2-(ethoxydifluoromethyl)-1,1,1,2,3,3,3-heptafluoropropane;

e) perchloroethylene;

f) 1-bromopropane;

g) acetone;

h) n-alkane (C12-C16);

i) t-butyl acetate; and

,

j) parachlorobenzotrifluoride;

2) 5-20% benzotrifluoride and 95-80% 1-bromopropane;

3) 10-90% acetone and 10-90% n-alkane (C12-C18);

4) 10-90% 1-bromopropane and 90-10% of one or more of;

a) chlorobromomethane; and

,

b) n-alkane (C12-C18);

5) 10-90% parachlorobenzotrifluoride and 90-10% of one or more of;

a) 1-bromopropane;

b) chlorobromomethane;

c) t-butyl acetate; and

,

d) n-alkane (C12-C18); and

,

6) 10-90% 1,2-dichloro-1,1,1-trifluoroethane and 90-10% of one or more of;

a) 1,1,1,2,2,3,3,4,4-nonafluoro-4-methoxy-butane;

b) 2-(difluoromethoxymethyl)-1,1,1,2,3,3,3-heptafluoropropane;

c) 1-ethoxy-1,1,2,2,3,3,4,4,4-nonafluorobutane;

d) 2-(ethoxydifluoromethyl)-1,1,1,2,3,3,3-heptafluoropropane;

e) 1-bromopropane;

f) acetone;

g) benzotrifluoride; and

,

h) methyl acetate.

8. The composition according to claim 1 wherein the solvent component consists essentially of 10-90% methylene chloride and 10-90% of one or more of the solvents selected from the group consisting of:

chlorobromomethane;

1-bromopropane;

methyl acetate;

n-alkane (C12-C18);

t-butyl acetate;

perchloroethylene;

benzotrifluoride;

parachlorobenzotrifluoride;

acetone;

10. The composition according to claim 1 for use as a blowing agent wherein the solvent component consists essentially of:

99-99.98%, by total volume of the solvent component, 1,2-dichloro-1,1,1-trifluoroethane and

0.01-0.5%, by total volume of the solvent component, alpha-methyl styrene to inhibit polymerization.

11. The composition according to claim 1 wherein the solvent consists essentially of 50-90%, by volume, 1-bromopropane, and the resin consists essentially of 10-30% of one or more of resins selected from the group of acrylic, thermoplastic or thermosetting polymers and urethane polymers.

12. The composition of claim 10 wherein the resin is a thermoplastic or thermosetting acrylic polymer.

13. The composition according to claim 1 wherein the solvent consists essentially of 45-85%, by volume, of 1-bromopropane, and the resin consists essentially of 10-30% of acrylic polymer or urethane polymer, and 5-10%, by volume, acetone to improve solubility.

14. The composition according to claim 1, wherein the solvent consists essentially of 40-90%, by total volume of the composition, 1-bromopropane, and wherein the resin consists essentially of 5-35% of a hydrocarbon resin, and 5-25% of at least one of styrene-butadiene, polychloroprene, polyvinyl chloride, acrylic, epoxy, urethane, nitrocellulose, or styrene resins.

15. The composition according to claim 13, wherein the hydrocarbon resin is selected from the group of olefin, rosin ester, and terpene.

16. The composition according to claim 1 wherein the solvent consists essentially of:

70-90%, by volume, 1,2-dichloro-1,1,1-trifluoroethane;

9-29% dimethoxymethane; and

,

0.5% butylene oxide and 0.5% nitromethane to stabilize the composition.

17. The composition according to claim 15 wherein approximately 5-10% by volume acetone is added to the composition to improve solubility as necessary.

18. The composition according to claim 1 wherein the solvent component, expressed in terms of % by total volume of the composition, consists essentially of 1-20% technical white oil and 10-90% of one or more solvents selected from the group consisting of:

(1) n-alkane (C12-C18);

(2) methyl acetate;

(3) t-butyl acetate;

(4) benzotrifluoride;

(5) acetone;

(6) parachlorobenzotrifluoride;

(7) parachlorobenzotrifluoride;

(8) perchloroethylene; and

,

(9) methylene chloride; and

,

(10) a mixture of methylene chloride, acetone, t-butyl acetate, methyl acetate and perchloroethylene.

19. The composition according to claim 17 wherein the solvent component, expressed in terms of % by total volume of the composition, consists essentially of 1-20% technical white oil and 10-90% of one or more of:

methylene chloride;

acetone;

t-butyl acetate;

methyl acetate; and

, perchloroethylene.

9. 2-dichloro-1,1,2-trifluoroethane;

and,

dimethoxymethane.

20. A solvent-resin composition for use as an adhesive consisting essentially of a resin component and a zero-VOC solvent component, wherein the zero-VOC solvent component is 40-90% by total volume of the composition, and is 1-bromopropane.

22. The composition according to claim 20 wherein the zero-VOC solvent consists essentially of 70-95%, by total volume of the composition, 1-bromopropane, and the resin consists essentially of 5-30% of one or more of resins selected from the group of acrylic, epoxy, urethane, nitrocellulose, styrene, polyvinyl chloride, and polychloroprene resins.

24. The composition according to claim 22 wherein at least a portion of the hydrocarbon resin is selected from the group of olefin, rosin ester and terpene.

26. The composition according to claim 24 wherein:

the polyether triol is present in the amount 60-65%;

the one or more of toluene diisocyanate and toluene disocyanurate is present in the amount of 30-33%;

the water is present in the amount of 1-2%;

the catalyst is present in the amount of 0.09-2%;

the surfactant is present in the amount of 0.3-1.5%; and

,

the one or more of 1-bromopropane and chlorobromomethane is present in the amount of 2.4-6.1%.

29. The cleaning composition of claim 26 wherein the one or more solvents, expressed in terms of total volume of the composition, is selected from the group consisting of:

(1) 10-90% benzotrifluoride and 10-90% of one or more of the solvents;

(a) 1,1,1,2,2,3,3,4,4-nonafluoro-4-methoxy-butane;

(b) 2-(difluoromethoxymethyl)-1,1,1,2,3,3,3-heptafluoropropane;

(c) 1-ethoxy-1,1,2,2,3,3,4,4,4-nonafluorobutane;

(d) 2-(ethoxydifluoromethyl)-1,1,1,2,3,3,3-heptafluoropropane;

(e) perchloroethylene;

(f) 1-bromopropane;

(g) acetone;

(h) n-alkane (C12-C16);

(i) t-buytl acetate (C12-C16); and

,

(j) parachlorobenzotrifluoride;

(2) 5-20% benzotrifluoride and 80-95% 1-bromopropane;

(3) 10-90% acetone and 10-90% n-alkane(C12-C18);

(4) 10-90% 1-bromopropane and 10-90% of one or more of;

(a) chlorobromomethane; and

,

(b) n-alkane (C12-C18);

(5) 10-90% parachlorobenzotrifluoride and 10-90% of one or more of;

(a) 1-bromopropane;

(b) chlorobromomethane;

(c) t-butyl acetate; and

,

(d) n-alkane (C12-C18);

(6) 10-90% 1,2-dichloro-1,1,1-trifluoroethane and 10-90% of one or more of;

21. A solvent-resin composition consisting essentially of a resin component and a zero-VOC solvent component, wherein the zero-VOC solvent component is 40-95%, by total volume of the composition, 1-bromopropane, and the resin component is 5-60% of one or more resins selected from the group consisting of acrylic, epoxy, urethane, nitrocellulose, styrene, polyvinyl chloride, and polychloroprene resins.

23. A resin-solvent composition for use as an adhesive comprising:

40-90%, by total volume of the composition, of one or more of 1-bromopropane and benzotrifluoride,

5-35% of a hydrocarbon resin as a tackifier, and

5-25% of a resin, selected from one or more of styrene-butadiene, polychloroprene, polyvinyl chloride, acrylic, epoxy, uretharie, nitrocellulose, and styrene resins.

25. A composition for use as a blowing agent in the manufacture of resin foams, the composition comprising, by total weight of the composition:

50-70% polyether triol;

20-40% of one or more of toluene diisocyanate and toluene disocyanurate;

0-5% catalyst;

0-5% surfactant;

0-10% water; and

,

2-15% of one or more of;

1-bromopropane;

chlorobromomethane.

27. A cleaning composition consisting essentially of zero volatile organic compounds (VOCs), the composition consisting essentially of one or more of the zero-VOC solvents selected from the group consisting of:

chlorobromomethane;

1-bromopropane;

n-alkane (C12-C18);

t-butyl acetate;

perchloroethylene;

benzotrifluoride;

parachlorobenzotrifluoride;

acetone;

28. 2-dichloro-1,1,2-trifluoroethane;

dimethoxymethane;

1,1,1,2,2,3,3,4,4-nonafluoro-4-methoxy-butane;

2-(difluoromethoxymethyl)-1,1,1,2,3,3,3-heptafluoropropane;

1-ethoxy-1,1,2,2,3,3,4,4,4-nonafluorobutane; and

,

2-(ethoxydifluoromethyl)-1,1,1,2,3,3,3-heptafluoropropane.

32. The composition of claim 28 wherein the solvent is 1-bromopropane.

33. The composition of claim 28 wherein the solvent is t-butyl acetate.

34. The composition of claim 28 wherein the solvent is methyl acetate.

35. The composition of claim 28 wherein the solvent is benzotrifluoride.

36. The composition of claim 28 wherein the solvent is acetone.

37. The composition of claim 28 wherein the solvent is methylene chloride.

38. The composition of claim 28 wherein the solvent is technical white oil.

40. The composition of claim 36 wherein the styrene polymer is styrene butadiene rubber.

41. The composition of claim 36 further comprising a tackifier.

42. The composition of claim 37 further comprising tackifier.

30. 1,1,2,2,3,3,4,4-nonafluoro-4-methoxy-butane;

2-(difluoromethoxymethyl)-1,1,1,2,3,3,3-heptafluoropropane;

1-ethoxy-1,1,2,2,3,3,4,4,4-nonafluorobutane;

2-(ethoxydifluoromethyl)-1,1,1,2,3,3,3-heptafluoropropane;

1-bromopropane

acetone;

benzotrifluoride; and

,

methyl acetate.

31. A solvent-resin composition consisting essentially of a resin component and a solvent component wherein the solvent component comprises 5% to 95% by total volume of the solvent-resin composition, further wherein the solvent is one or more zero-VOC, non ground based ozone forming solvents selected from the group consisting of:

1) 1-bromopropane;

2) t-butylacetate;

3) methyl acetate;

4) benzotrifluoride;

5) acetone;

6) methylene chloride; and

,

7) technical white oils (mineral oils).

39. A solvent-resin composition comprising a resin component and a solvent component, wherein the solvent component comprises 5% to 95% by total volume of the solvent-resin composition, further wherein the solvent is 1-bromopropane and the resin is a styrene polymer.

43. A zero-VOC cleaning composition consisting essentially of the zero-VOC solvent, t-butyl acetate.