Plasticizer blends and use thereof

Patent metadata

Field	Value
Publication number	US-9534104-B2
Application number	US-201414319906-A
Country	US
Kind code	B2
Filing date	Jun 30, 2014
Priority date	Jan 28, 2013
Publication date	Jan 3, 2017
Grant date	Jan 3, 2017

Abstract

Provided are mixtures of 1) compounds of the formula:

wherein R 1 is a saturated or unsaturated cyclic hydrocarbon optionally substituted with an alkyl and/or an OXO-ester, and R 2 is a C 4 to C 14 hydrocarbyl; and 2) one or more second plasticizers selected from the group consisting of alkyl terephthalates, alkyl phthalates, alkyl benzoate esters, di-benzoate esters, esters of cyclohexane polycarboxylic acids, and dialkyl adipates. Also provided are plasticized polymer compositions containing said mixtures.

First claim

We claim:

1. A mixture comprising:
1)
(i) at least two first plasticizer compounds of the formula:

wherein each R 1 is, independently, a phenyl group where the phenyl is substituted with an alkyl and/or an OXO-ester at the ortho-, meta-, or para-position, and each R 2 is, independently, a C 4 to C 20 hydrocarbyl or
ii) at least one first plasticizer compound(s) represented by one or more of the formulae:

wherein R 2 is a C 4 to C 20 hydrocarbyl,
2) one or more second plasticizers comprising alkyl terephthalate, alkyl phthalate, alkyl benzoate ester, di-benzoate ester, ester of cyclohexane polycarboxylic acid, dialkyl adipate or a mixture thereof.

2. The mixture of claim 1 , wherein at least one R 1 is located at the ortho-, meta- or para-position.

3. The mixture of claim 1 , wherein at least one R 1 is phenyl located at the para-position.

4. The mixture of claim 1 , wherein at least one R 1 is tolyl.

5. The mixture of claim 1 , wherein at least one R 2 is not linear.

6. The mixture of claim 1 , wherein the first plasticizer compound is a mixture of at least two compounds represented by the formula:

wherein R 1 is a phenyl group where the phenyl is substituted with an alkyl at the ortho-, meta-, or para-position, and R 2 is a C 4 to C 20 hydrocarbyl, where R 2 is branched in the first first plasticizer and R 2 is linear in the second first plasticizer compound.

7. The mixture of claim 1 , wherein at least one R 1 is tolyl and at least one R 2 is a C 9 or C 10 hydrocarbyl.

8. The mixture of claim 1 , wherein the second plasticizer compound(s) comprises at least two compounds from the group consisting of alkyl terephthalates, alkyl phthalates, alkyl benzoate esters, di-benzoate esters, esters of cyclohexane polycarboxylic acids, and dialkyl adipates.

9. The mixture of claim 1 , wherein the second plasticizer compound(s) comprises C 4 to C 12 alkyl terephthalates, C 4 to C 14 alkyl phthalates, C 4 to C 14 alkyl isophthalates, C 7 to C 13 alkyl benzoate esters, C 4 to C 13 dialkyl adipates, or combinations thereof.

10. The mixture of claim 1 , wherein the second plasticizer compound(s) comprises one or more of di-n-butyl terephthalate, diisobutyl terephthalate, di-n-octyl terephthalate, diisooctyl terephthalate, di-2-ethylhexyl terephthalate, di-n-nonyl terephthalate, diisononyl terephthalate, di-n-decyl terephthalate, di-2-propyl heptyl terephthalate, diisodecyl terephthalate, di-n-nonyl phthalate, diisononyl phthalate, di-n-decyl phthalate, diisodecyl phthalate, di-2-propyl heptyl phthalate, di-n-undecyl phthalate, ditridecyl phthalate, diisotridecyl phthalate, di-n-propyl isophthalate, di-n-nonyl isophthalate, diisononyl isophthalate, di-n-decyl isophthalate, diisodecyl isophthalate, di-2-propyl heptyl isophthalate, di-n-undecyl isophthalate, diisotridecyl isophthalate, isononyl benzoate, nonyl benzoate, isodecyl benzoate, decyl benzoate, 2-propylheptyl benzoate, isoundecyl benzoate, isotridecyl benzoate, di-heptyl cyclohexanoate, di-2-ethylhexyl cyclohexanoate, di-n-nonyl cyclohexanoate, diisononyl cyclohexanoate, di-n-decyl cyclohexanoate, diisodecyl cyclohexanoate, di-2-propyl heptyl cyclohexanoate, diheptyl adipate, dioctyl adipate, diisononyl adipate, diisodecyl adipate, di 2-propylheptyl adipate, dipropylene glycol dibenzoate, diethylene glycol dibenzoate, triethylene glycol dibenzoate, or mixtures thereof.

11. The mixture of claim 1 , wherein the second plasticizer compound(s) comprises one or more alkyl 1,2-cyclohexanedicarboxylates, alkyl 1,3-cyclohexanedicarboxylates and/or alkyl 1,4-cyclohexanedicarboxylates, where the alkyl has 4 to 13 carbons in the side chain.

12. The mixture of claim 1 , wherein the second plasticizer compound(s) comprises one or more of di-(2-ethylhexyl) phthalate, diisononyl phthalate, diisonyl phthalate, diisodecyl phthalate, di-(2-propylheptyl) phthalate, heptylundecyl phthalate, nonylundecyl phthalate, diundecyl phthalate, diisoundecyl phthalate, diisotridecyl phthalate, diisonyl cyclohexanoate, bis(2-ethyl hexyl) cyclohexanoate, diisononyl cyclohexanoate, di-(2-ethylhexyl) adipate, diisononyl adipate, isononyl benzoate, isodecyl benzoate, and bis(2-ethylhexyl) terephthalate.

13. The mixture of claim 1 , wherein the second plasticizer compound(s) comprises one or more of diisononyl phthalate, diisononyl adipate, isodecyl monobenzoate, and the first plasticizer comprises one or more substituted or unsubstituted biphenyl carboxylates.

14. The mixture of claim 1 , wherein the first plasticizer(s) is present at 1 to 99 wt % and the second plasticizer(s) is present at 99 to 1 wt %, based upon the weight of the plasticizers.

15. A polymer composition comprising a thermoplastic polymer and 20 to 120 phr of the mixture of claim 1 .

16. A polymer composition comprising
1) a thermoplastic polymer;
2) (i) at least two first plasticizer compounds of the formula:

wherein each R 1 is, independently, a phenyl group where the phenyl is substituted with an alkyl and/or an OXO-ester at the ortho-, meta-, or para-position, and each R 2 is, independently, a C 4 to C 20 hydrocarbyl; or
ii) at least one first plasticizer compound(s) represented by one or more of the formulae:

wherein R 2 is a C 4 to C 20 hydrocarbyl;
3) a second plasticizer comprising alkyl terephthalate, alkyl phthalate, C 7 to C 13 alkyl benzoate ester, di-benzoate ester, ester of cyclohexane polycarboxylic acid, dialkyl adipate or a mixture thereof.

17. The polymer composition of claim 16 , wherein the thermoplastic polymer comprises vinyl chloride resins, polyesters, polyurethanes, ethylene-vinyl acetate copolymer, rubbers, poly(meth)acrylics and combinations thereof.

18. The polymer composition of claim 16 , wherein the thermoplastic polymer is polyvinyl chloride.

19. The polymer composition of claim 16 , wherein the thermoplastic polymer is present at 99 to 40 wt % and the plasticizers are present at 1 to 60 wt %.

20. A wire and cable coating formulation comprising: i) 100 parts by weight PVC; (ii) 20 to 80 parts of the compounds of the mixture of claim 1 ; (iii) a filler; and (iv) a stabilizer.

21. The wire and cable coating formulation of claim 20 , wherein the filler is present at from 1 to 100 parts by weight per 100 parts of the PVC and the stabilizer is present at from 5 to 15 parts by weight per 100 parts of the PVC.

22. A wire or cable coated with a composition of claim 20 .

23. A cable filling compound comprising: i) 100 parts by weight PVC; ii) 20 to 80 parts by weight per 100 parts of the PVC of the mixture of claim 1 ;
iii) 1 to 600 parts by weight per 100 parts of the PVC of filler; and iv) 5 to 15 parts by weight per 100 parts of the PVC of stabilizer.

24. The mixture of claim 16 , wherein the composition comprises the plasticizers in an amount of from 5 to 90 phr.

25. The polymer composition of claim 16

Assignees

• Exxonmobil Chemical Patents Inc

Inventors

• Naert Didier
• Leroy Bernard F
• Costello Christine A
• Zushma Stephen

Classifications

• C08K5/101 Primary

  of monocarboxylic acids · CPC title

• C08K5/12

  of cyclic polycarboxylic acids · CPC title

• C09D127/06

  Homopolymers or copolymers of vinyl chloride · CPC title

• Y10T428/2967

  Synthetic resin or polymer · CPC title

• H01B3/443

  from vinylhalogenides or other halogenoethylenic compounds · CPC title