IP Library Granted Patent US 8,071,519
Granted Patent B2
US 8,071,519 · App. 10/572,994 · Granted Dec 6, 2011

Polybasic acid esters and their use in fibre optic cables

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Quick Facts
Patent No.
US 8,071,519
App. No.
10/572,994
Granted
Dec 6, 2011
Kind
B2
Abstract

A composition comprising a blend of first and second esters: the first ester comprising a reaction product of first reactants comprising trimer acid, first polyhydric alcohol and first monohydric alcohol; the first monohydric alcohol selected from the group of C8-18 monohydric alcohols; the second ester comprising a reaction product of second reactants comprising trimer acid, second polyhydric alcohol and second monohydric alcohol; the second monohydric alcohol selected from the group of C6-10 monohydric alcohols; the first and second monohydric alcohols being non-identical. This blend of esters, in combination with silica, is useful as a sealant composition, e.g., as a cable-protectant composition.

Claims (45)

1. A composition comprising a blend of first and second esters, the first ester comprising a reaction product of first reactants comprising trimer acid derived from tall oil fatty acids or reactive equivalent thereof, first polyhydric alcohol or reactive equivalent thereof, and first monohydric alcohol or reactive equivalent thereof; the first monohydric alcohol being selected from the group of C.sub.8-18 monohydric alcohols or reactive equivalents thereof; the second ester comprising a reaction product of second reactants comprising trimer acid derived from tall oil fatty acids or reactive equivalent thereof, second polyhydric alcohol or reactive equivalent thereof, and second monohydric alcohol or reactive equivalent thereof; the second monohydric alcohol being selected from the group of C.sub.6-10 monohydric alcohols or reactive equivalents thereof; the first and second monohydric alcohols being non-identical;

wherein the first reactants are heated to a temperature of about 200° C. to about 250° C. and maintained at that temperature from about 5½ hours to 13 hours under vacuum as required to maintain reflux, wherein thereafter the resulting first reaction mixture is optionally subjected to a vacuum of about 20-200 mm for removal of volatile materials, and wherein thereafter the temperature of the resulting first reaction mixture is lowered to about 130° C., and

wherein the second reactants are heated to a temperature of about 200° C. to about 250° C. and maintained at that temperature from about 5½ hours to 13 hours under vacuum as required to maintain reflux, wherein thereafter the resulting second reaction mixture is optionally subjected to vacuum of about 20-200 mm for removal of volatile materials, and wherein thereafter the temperature of the resulting second reaction mixture is lowered to about 130° C.,

wherein further the weight of a polypropylene sample increases less than about 5 wt. % through absorption of the composition following exposure of the polypropylene and the composition at a temperature of about 80° C. after a period of four weeks.

2. The composition of claim 1 wherein the first reactants and the second reactants each further comprise dimer acid.

3. The composition of claim 2 wherein the first reactants and the second reactants each comprise dimer acid and trimer acid, in a dimer acid:trimer acid weight ratio of 20:80 to 80:20, the weight ratio independently selected in each of the first and second reactants.

4. The composition of any of claim 1 , 2 or 3 wherein the trimer acid is hydrogenated trimer acid.

5. The composition of any of claim 1 , 2 , or 3 wherein the first monohydric alcohol is selected from C.sub.10-14 primary monohydric alcohols.

6. The composition of claim 5 wherein the first monohydric alcohol is iso-tridecyl alcohol.

7. The composition of any of claim 1 , 2 , or 3 wherein the first and second polyhydric alcohols are each selected from C.sub.3-15 polyhydric alcohols.

8. The composition of claim 7 wherein the first and second polyhydric alcohols are each independently selected from pentaerythritol, di-pentaerythritol, tri-pentaerythritol, trimethylolpropane, ethylene glycol and neopentyl glycol.

9. The composition of claim 7 wherein the first and second polyhydric alcohols are each neopentyl glycol.

10. The composition of any of claim 1 , 2 , or 3 , wherein the second monohydric alcohol is selected from 2-ethylhexanol, 2-octanol and cyclohexyl alcohol.

11. The composition of claim 10 wherein the second monohydric alcohol is 2-ethylhexanol.

12. The composition of any of claim 1 , 2 , or 3 wherein the first ester has a greater viscosity than the second ester.

13. The composition of claim 12 having a viscosity of 30-50 cSt at 100.degree. C.

14. The composition of claim 13 having a viscosity of about 40 cSt at 100.degree. C.

15. The composition of claim 1 wherein the first monohydric alcohol is selected from the group of C.sub.10-15 primary monohydric alcohols; the second monohydric alcohol is selected from the group consisting of C.sub.8 monohydric alcohols; the first and second polyhydric alcohols are selected from C.sub.3-15 polyhydric alcohols, and the viscosity of the composition is in the range of 30-50 cSt at 100.degree. C.

16. A method for preparing an ester composition having a viscosity in the range of 30-50 cSt at 100.degree. C., the method comprising the steps of: a) preparing a first ester, the first ester comprising a reaction product of first reactants comprising trimer acid derived from tall oil fatty acids, first polyhydric alcohol and first monohydric alcohol; the first monohydric alcohol selected from the group of C.sub.8-18 monohydric alcohols; b) preparing a second ester, the second ester comprising a reaction product of second reactants comprising trimer acid derived from tall oil fatty acids, second polyhydric alcohol and second monohydric alcohol; the second monohydric alcohol selected from the group of C.sub.6-10 monohydric alcohols; and c) blending the first and second esters together in a proportion to provide an ester composition having a viscosity in the range of 30-50 cSt at 100.degree. C.; with the proviso that the first and second monohydric alcohols are non-identical;

wherein the first reactants are heated to a temperature of about 200° C. to about 250° C. and maintained at that temperature from about 5½ hours to 13 hours under vacuum as required to maintain reflux, wherein thereafter the resulting first reaction mixture is optionally subjected to a vacuum of about 20-200 mm for removal of volatile materials, and wherein thereafter the temperature of the resulting first reaction mixture is lowered to about 130° C., and

wherein the second reactants are heated to a temperature of about 200° C. to about 250° C. and maintained at that temperature from about 5½ hours to 13 hours under vacuum as required to maintain reflux, wherein thereafter the resulting second reaction mixture is optionally subjected to vacuum of about 20-200 mm for removal of volatile materials, and wherein thereafter the temperature of the resulting second reaction mixture is lowered to about 130° C.,

wherein further the weight of a polypropylene sample increases less than about 5 wt. % through absorption of the composition following exposure of the polypropylene and the composition at a temperature of about 80° C. after a period of four weeks.

17. The method of claim 16 wherein the first reactants and the second reactants each further comprise dimer acid, in a dimer acid:trimer acid weight ratio of 20:80 to 80:20, the weight ratio independently selected in each of the first and second reactants.

18. The method of any of claim 16 or 17 wherein the trimer acid is hydrogenated trimer acid.

19. The method of any of claim 16 or 17 wherein the first monohydric alcohol is selected from C.sub.10-14 primary monohydric alcohols.

20. The method of any of claim 16 or 17 wherein the first and second polyhydric alcohols are each selected from C.sub.3-15 polyhydric alcohols.

21. The method of any of claim 16 or 17 wherein the second monohydric alcohol is selected from 2-ethylhexanol, 2-octanol and cyclohexyl alcohol.

22. The method of any of claim 16 or l 7 wherein the first ester has a greater viscosity than the second ester.

23. The method of claim 16 wherein the first monohydric alcohol is selected from the group of C.sub.10-15 primary monohydric alcohols; the second monohydric alcohol is selected from the group consisting of C.sub.8 monohydric alcohols; the first and second polyhydric alcohols are selected from C.sub.3-15 polyhydric alcohols; and the first ester has a greater viscosity than the second ester.

24. A composition prepared by the method of any of claims 16 or 17 .

25. A cable-filling composition comprising silica and a blend of first and second esters, the first ester comprising a reaction product of first reactants comprising trimer acid derived from tall oil fatty acids, first polyhydric alcohol and first monohydric alcohol; the first monohydric alcohol selected from the group of C.sub.8-18 monohydric alcohols; the second ester comprising a reaction product of second reactants comprising trimer acid derived from tall oil fatty acids, second polyhydric alcohol and second monohydric alcohol; the second monohydric alcohol selected from the group of C.sub.6-10 monohydric alcohols; the first and second monohydric alcohols being non-identical;

wherein the first reactants are heated to a temperature of about 200° C. to about 250° C. and maintained at that temperature from about 5½ hours to 13 hours under vacuum as required to maintain reflux, wherein thereafter the resulting first reaction mixture is optionally subjected to a vacuum of about 20-200 mm for removal of volatile materials, and wherein thereafter the temperature of the resulting first reaction mixture is lowered to about 130° C., and

wherein the second reactants are heated to a temperature of about 200° C. to about 250° C. and maintained at that temperature from about 5½ hours to 13 hours under vacuum as required to maintain reflux, wherein thereafter the resulting second reaction mixture is optionally subjected to vacuum of about 20-200 mm for removal of volatile materials, and wherein thereafter the temperature of the resulting second reaction mixture is lowered to about 130° C.,

wherein further the weight of a polypropylene sample increases less than about 5 wt. % through absorption of the composition following exposure of the polypropylene and the composition at a temperature of about 80° C. after a period of four weeks.

26. The composition of claim 25 wherein the first monohydric alcohol is selected from the group of C.sub.10-15 primary monohydric alcohols; the second monohydric alcohol is selected from the group consisting of C.sub.8 monohydric alcohols; the first and second polyhydric alcohols are selected from C.sub.3-15 polyhydric alcohols, and the viscosity of the blend is in the range of 30-50 cSt at 100.degree. C.

27. A method for insulating the contents of a cable, the method comprising a) preparing a cable-filling composition comprising silica and a blend of first and second esters; the first ester comprising a reaction product of first reactants comprising trimer acid derived from tall oil fatty acids, first polyhydric alcohol and first monohydric alcohol; the first monohydric alcohol selected from the group of C.sub.8-18 monohydric alcohols; the second ester comprising a reaction product of second reactants comprising trimer acid derived from tall oil fatty acids, second polyhydric alcohol and second monohydric alcohol; the second monohydric alcohol selected from the group of C.sub.6-10 monohydric alcohols; the first and second monohydric alcohols being non-identical; b) placing the cable-filling composition of step a) into a fiber optic cable;

wherein the first reactants are heated to a temperature of about 200° C. to about 250° C. and maintained at that temperature from about 5½ hours to 13 hours under vacuum as required to maintain reflux, wherein thereafter the resulting first reaction mixture is optionally subjected to a vacuum of about 20-200 mm for removal of volatile materials, and wherein thereafter the temperature of the resulting first reaction mixture is lowered to about 130° C., and

wherein the second reactants are heated to a temperature of about 200° C. to about 250° C. and maintained at that temperature from about 5½ hours to 13 hours under vacuum as required to maintain reflux, wherein thereafter the resulting second reaction mixture is optionally subjected to vacuum of about 20-200 mm for removal of volatile materials, and wherein thereafter the temperature of the resulting second reaction mixture is lowered to about 130° C.,

wherein further the weight of a polypropylene sample increases less than about 5 wt. % through absorption of the composition following exposure of the polypropylene and the composition at a temperature of about 80° C. after a period of four weeks.

28. The method of claim 27 wherein the cable is a fiber optic cable.

29. A cable comprising a cable-filling composition; the cable-filling composition comprising silica and a blend of first and second esters; the first ester comprising a reaction product of first reactants comprising trimer acid derived from tall oil fatty acids, first polyhydric alcohol and first monohydric alcohol; the first monohydric alcohol selected from the group of C.sub.8-18 monohydric alcohols; the second ester comprising a reaction product of second reactants comprising trimer acid derived from tall oil fatty acids, second polyhydric alcohol and second monohydric alcohol; the second monohydric alcohol selected from the group of C.sub.6-10 monohydric alcohols; wherein the first and second monohydric alcohols are non-identical;

wherein the first reactants are heated to a temperature of about 200° C. to about 250° C. and maintained at that temperature from about 5½ hours to 13 hours under vacuum as required to maintain reflux, wherein thereafter the resulting first reaction mixture is optionally subjected to a vacuum of about 20-200 mm for removal of volatile materials, and wherein thereafter the temperature of the resulting first reaction mixture is lowered to about 130° C., and

wherein the second reactants are heated to a temperature of about 200° C. to about 250° C. and maintained at that temperature from about 5½ hours to 13 hours under vacuum as required to maintain reflux, wherein thereafter the resulting second reaction mixture is optionally subjected to vacuum of about 20-200 mm for removal of volatile materials, and wherein thereafter the temperature of the resulting second reaction mixture is lowered to about 130° C.,

wherein further the weight of a polypropylene sample increases less than about 5 wt. % through absorption of the composition following exposure of the polypropylene and the composition at a temperature of about 80° C. after a period of four weeks.

30. The cable of claim 29 wherein the cable is a fiber optic cable.

Assignments (20)
CORRECTIVE ASSIGNMENT TO CORRECT THE PATENT NO. 8837224 TO PATENT NO. 7737224 PREVIOUSLY RECORDED AT REEL: 037448 FRAME: 0453. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 11, 2022
From: KRATON POLYMERS U.S. LLC; ARIZONA CHEMICAL COMPANY, LLC
To: BANK OF AMERICA, N.A.
Reel/Frame 060344/0919 →
RELEASE OF SECURITY INTEREST Recorded Mar 15, 2022
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
To: ARIZONA CHEMICAL COMPANY, LLC
Reel/Frame 059366/0727 →
PATENT SECURITY AGREEMENT Recorded Jan 7, 2016
From: ARIZONA CHEMICAL COMPANY, LLC
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
Reel/Frame 037457/0928 →
RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded Jan 6, 2016
From: ANTARES CAPITAL LP, AS SUCCESSOR TO GENERAL ELECTRIC CAPITAL CORPORATION
To: ARIZONA CHEMICAL COMPANY LLC
Reel/Frame 037451/0057 →
RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY COLLATERAL AT REEL/FRAME NO. 33146/0361 Recorded Jan 6, 2016
From: GOLDMAN SACHS BANK USA
To: ARIZONA CHEMICAL COMPANY LLC
Reel/Frame 037451/0169 →
CORRECTIVE ASSIGNMENT TO CORRECT THE PATENT NUMBER 8837224 TO PATENT NUMBER 7737224 PREVIOUSLY RECORDED AT REEL: 037448 FRAME: 0453. ASSIGNOR(S) HEREBY CONFIRMS THE SECURITY INTEREST. Recorded Jan 6, 2016
From: KRATON POLYMERS U.S. LLC; ARIZONA CHEMICAL COMPANY, LLC
To: BANK OF AMERICA, N.A.
Reel/Frame 037448/0453 →
ASSIGNMENT OF INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Oct 9, 2015
From: GENERAL ELECTRIC CAPITAL CORPORATION, AS RETIRING AGENT
To: ANTARES CAPITAL LP, AS SUCCESSOR AGENT
Reel/Frame 036827/0443 →
RELEASE OF SECURITY INTEREST Recorded Jun 12, 2014
From: GENERAL ELECTRIC CAPITAL CORPORATION, AS COLLATERAL AGENT
To: ARIZONA CHEMICAL COMPANY LLC
Reel/Frame 033146/0278 →
SECURITY INTEREST Recorded Jun 12, 2014
From: ARIZONA CHEMICAL COMPANY LLC
To: GENERAL ELECTRIC CAPITAL CORPORATION, AS FIRST LIEN COLLATERAL AGENT
Reel/Frame 033146/0333 →
SECURITY INTEREST Recorded Jun 12, 2014
From: ARIZONA CHEMICAL COMPANY LLC
To: GOLDMAN SACHS BANK USA, AS SECOND LIEN COLLATERAL AGENT
Reel/Frame 033146/0361 →
SECURITY AGREEMENT Recorded Jan 7, 2012
From: ARIZONA CHEMICAL COMPANY, LLC
To: GENERAL ELECTRIC CAPITAL CORPORATION, AS COLLATERAL AGENT
Reel/Frame 027497/0465 →
RELEASE OF SECURITY INTEREST Recorded Jan 6, 2012
From: GENERAL ELECTRIC CAPITAL CORPORATION
To: ARIZONA CHEMICAL COMPANY, LLC
Reel/Frame 027489/0030 →
SECURITY AGREEMENT Recorded Feb 2, 2011
From: ARIZONA CHEMICAL COMPANY, LLC
To: GENERAL ELECTRIC CAPITAL CORPORATION, AS COLLATERAL AGENT
Reel/Frame 025734/0383 →
RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY COLLATERAL (FIRST LIEN) Recorded Jan 31, 2011
From: GOLDMAN SACHS CREDIT PARTNERS, L.P.
To: ARIZONA CHEMICAL COMPANY
Reel/Frame 025719/0265 →
RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY COLLATERAL (SECOND LIEN) Recorded Jan 31, 2011
From: WILMINGTON TRUST FSB (SUCCESSOR TO CAPITALSOURCE FINANCE LLC)
To: ARIZONA CHEMICAL COMPANY
Reel/Frame 025720/0248 →
CHANGE OF NAME Recorded Nov 24, 2010
From: ARIZONA CHEMICAL COMPANY
To: ARIZONA CHEMICAL COMPANY, LLC
Reel/Frame 025406/0597 →
CHANGE OF NAME Recorded Aug 30, 2010
From: CAPITALSOURCE FINANCE LLC
To: WILMINGTON TRUST FSB
Reel/Frame 024944/0501 →
FIRST LIEN PATENT SECURITY AGREEMENT Recorded Mar 20, 2007
From: ARIZONA CHEMICAL COMPANY
To: GOLDMAN SACHS CREDIT PARTNERS, L.P.
Reel/Frame 019035/0392 →
SECOND LIEN PATENT SECURITY AGREEMENT Recorded Mar 20, 2007
From: ARIZONA CHEMICAL COMPANY
To: CAPITAL SOURCE FINANCE, LLC
Reel/Frame 019035/0423 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 29, 2006
From: NELSON, LLOYD A.; MOSBY, NANCY D.
To: ARIZONA CHEMICAL COMPANY
Reel/Frame 018560/0240 →