CA1114834A - SAVONS ET ESTERS SAPONIFIES D'ACIDES A P.M. ELEVE, DERIVES D'.alpha.-OLEFINES - Google Patents

SAVONS ET ESTERS SAPONIFIES D'ACIDES A P.M. ELEVE, DERIVES D'.alpha.-OLEFINES

Info

Publication number: CA1114834A
Authority: CA; Canada
Prior art keywords: carbon atoms; weight; acids; soap; acid
Prior art date: 1976-09-13
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA280,433A

Other languages

English (en)

Inventor

Harold C. Foulks, Jr.

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Emery Oleochemicals LLC

Original Assignee

Emery Oleochemicals LLC

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-09-13

Filing date

1977-06-13

Publication date

1981-12-22

1977-06-13 Application filed by Emery Oleochemicals LLC filed Critical Emery Oleochemicals LLC

1981-12-22 Application granted granted Critical

1981-12-22 Publication of CA1114834A publication Critical patent/CA1114834A/fr

Status Expired legal-status Critical Current

Links

239000002253 acid Substances 0.000 title claims abstract description 219
239000000344 soap Substances 0.000 title claims abstract description 190
150000007513 acids Chemical class 0.000 title claims abstract description 148
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 178
150000001336 alkenes Chemical class 0.000 claims abstract description 125
-1 aliphatic mono-carboxylic acids Chemical class 0.000 claims abstract description 80
229920005989 resin Polymers 0.000 claims abstract description 52
239000011347 resin Substances 0.000 claims abstract description 52
150000003254 radicals Chemical class 0.000 claims abstract description 32
239000000314 lubricant Substances 0.000 claims abstract description 31
238000006385 ozonation reaction Methods 0.000 claims abstract description 26
238000007342 radical addition reaction Methods 0.000 claims abstract description 26
229910052751 metal Inorganic materials 0.000 claims description 81
239000002184 metal Substances 0.000 claims description 81
239000000203 mixture Substances 0.000 claims description 80
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 62
239000011575 calcium Substances 0.000 claims description 46
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 45
229910052791 calcium Inorganic materials 0.000 claims description 45
150000002763 monocarboxylic acids Chemical class 0.000 claims description 37
150000002739 metals Chemical class 0.000 claims description 31
235000019260 propionic acid Nutrition 0.000 claims description 31
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 31
125000001931 aliphatic group Chemical group 0.000 claims description 30
FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 27
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 25
229910052799 carbon Inorganic materials 0.000 claims description 25
150000001875 compounds Chemical class 0.000 claims description 25
229910001385 heavy metal Inorganic materials 0.000 claims description 25
229910052783 alkali metal Inorganic materials 0.000 claims description 24
150000001340 alkali metals Chemical class 0.000 claims description 24
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 22
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 22
150000001342 alkaline earth metals Chemical class 0.000 claims description 22
239000011135 tin Substances 0.000 claims description 22
229910052718 tin Inorganic materials 0.000 claims description 22
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 19
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 18
229910052788 barium Inorganic materials 0.000 claims description 18
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 18
229910052744 lithium Inorganic materials 0.000 claims description 18
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 17
239000011777 magnesium Substances 0.000 claims description 17
229910052749 magnesium Inorganic materials 0.000 claims description 17
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 16
230000007935 neutral effect Effects 0.000 claims description 16
229910052725 zinc Inorganic materials 0.000 claims description 16
239000011701 zinc Substances 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
229920005862 polyol Polymers 0.000 claims description 14
239000005643 Pelargonic acid Substances 0.000 claims description 13
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 12
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
239000011630 iodine Substances 0.000 claims description 12
229910052740 iodine Inorganic materials 0.000 claims description 12
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 11
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 10
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 10
229920005992 thermoplastic resin Polymers 0.000 claims description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 6
TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims description 6
PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 claims description 5
AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 claims description 5
239000005639 Lauric acid Substances 0.000 claims description 5
238000002844 melting Methods 0.000 claims description 5
230000008018 melting Effects 0.000 claims description 5
JYKSTGLAIMQDRA-UHFFFAOYSA-N tetraglycerol Chemical compound OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO JYKSTGLAIMQDRA-UHFFFAOYSA-N 0.000 claims description 5
229940005605 valeric acid Drugs 0.000 claims description 5
GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims description 3
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 3
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 3
239000011342 resin composition Substances 0.000 claims description 3
PGTXKIZLOWULDJ-UHFFFAOYSA-N [Mg].[Zn] Chemical compound [Mg].[Zn] PGTXKIZLOWULDJ-UHFFFAOYSA-N 0.000 claims 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 40
150000002762 monocarboxylic acid derivatives Chemical class 0.000 abstract description 33
238000005461 lubrication Methods 0.000 abstract description 15
238000002360 preparation method Methods 0.000 abstract description 14
229920001577 copolymer Polymers 0.000 abstract description 7
229920001519 homopolymer Polymers 0.000 abstract description 5
239000000047 product Substances 0.000 description 50
238000006243 chemical reaction Methods 0.000 description 35
238000000034 method Methods 0.000 description 27
239000004800 polyvinyl chloride Substances 0.000 description 26
229920000915 polyvinyl chloride Polymers 0.000 description 25
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 20
150000002148 esters Chemical class 0.000 description 20
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 17
239000001301 oxygen Substances 0.000 description 17
229910052760 oxygen Inorganic materials 0.000 description 17
230000003647 oxidation Effects 0.000 description 16
238000007254 oxidation reaction Methods 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
230000008569 process Effects 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
WURFKUQACINBSI-UHFFFAOYSA-M ozonide Chemical compound [O]O[O-] WURFKUQACINBSI-UHFFFAOYSA-M 0.000 description 13
239000003054 catalyst Substances 0.000 description 12
238000009472 formulation Methods 0.000 description 11
230000004927 fusion Effects 0.000 description 11
239000001993 wax Substances 0.000 description 11
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 10
150000002736 metal compounds Chemical class 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
238000010504 bond cleavage reaction Methods 0.000 description 9
230000007017 scission Effects 0.000 description 9
238000007792 addition Methods 0.000 description 8
235000019441 ethanol Nutrition 0.000 description 8
150000003077 polyols Chemical class 0.000 description 8
238000012545 processing Methods 0.000 description 8
238000000354 decomposition reaction Methods 0.000 description 7
239000007789 gas Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
239000006096 absorbing agent Substances 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 6
239000000920 calcium hydroxide Substances 0.000 description 6
229910001861 calcium hydroxide Inorganic materials 0.000 description 6
239000004615 ingredient Substances 0.000 description 6
239000000155 melt Substances 0.000 description 6
239000003381 stabilizer Substances 0.000 description 6
238000012360 testing method Methods 0.000 description 6
235000019437 butane-1,3-diol Nutrition 0.000 description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
239000005977 Ethylene Substances 0.000 description 4
239000004605 External Lubricant Substances 0.000 description 4
244000068988 Glycine max Species 0.000 description 4
235000010469 Glycine max Nutrition 0.000 description 4
239000004610 Internal Lubricant Substances 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 4
238000013019 agitation Methods 0.000 description 4
KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
238000001125 extrusion Methods 0.000 description 4
235000011187 glycerol Nutrition 0.000 description 4
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
239000003879 lubricant additive Substances 0.000 description 4
239000000463 material Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
230000000704 physical effect Effects 0.000 description 4
239000000376 reactant Substances 0.000 description 4
238000007127 saponification reaction Methods 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000010936 titanium Substances 0.000 description 4
239000004711 α-olefin Substances 0.000 description 4
229940058015 1,3-butylene glycol Drugs 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000006057 Non-nutritive feed additive Substances 0.000 description 3
229910052793 cadmium Inorganic materials 0.000 description 3
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
238000013329 compounding Methods 0.000 description 3
229910003460 diamond Inorganic materials 0.000 description 3
239000010432 diamond Substances 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
238000002845 discoloration Methods 0.000 description 3
238000009826 distribution Methods 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
239000011521 glass Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
230000004048 modification Effects 0.000 description 3
238000012986 modification Methods 0.000 description 3
239000012170 montan wax Substances 0.000 description 3
230000003472 neutralizing effect Effects 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
CBQYNPHHHJTCJS-UHFFFAOYSA-N Alline Chemical compound C1=CC=C2C3(O)CCN(C)C3NC2=C1 CBQYNPHHHJTCJS-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 2
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
239000004676 acrylonitrile butadiene styrene Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
239000012159 carrier gas Substances 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
230000001627 detrimental effect Effects 0.000 description 2
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 2
239000000539 dimer Substances 0.000 description 2
239000000975 dye Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000001307 helium Substances 0.000 description 2
229910052734 helium Inorganic materials 0.000 description 2
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
239000003999 initiator Substances 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical class CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
150000001451 organic peroxides Chemical class 0.000 description 2
229940059574 pentaerithrityl Drugs 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
229920002554 vinyl polymer Polymers 0.000 description 2
238000005406 washing Methods 0.000 description 2
GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 1
OQBLGYCUQGDOOR-UHFFFAOYSA-L 1,3,2$l^{2}-dioxastannolane-4,5-dione Chemical compound O=C1O[Sn]OC1=O OQBLGYCUQGDOOR-UHFFFAOYSA-L 0.000 description 1
XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
ZZQCGJSFWKIOBB-UHFFFAOYSA-N 2,3,3-trimethyldecan-2-ol Chemical compound CCCCCCCC(C)(C)C(C)(C)O ZZQCGJSFWKIOBB-UHFFFAOYSA-N 0.000 description 1
OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
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239000004801 Chlorinated PVC Substances 0.000 description 1
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239000004594 Masterbatch (MB) Substances 0.000 description 1
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239000004435 Oxo alcohol Substances 0.000 description 1
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239000003377 acid catalyst Substances 0.000 description 1
150000008043 acidic salts Chemical class 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
238000004380 ashing Methods 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
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230000008901 benefit Effects 0.000 description 1
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ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
229910052797 bismuth Inorganic materials 0.000 description 1
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
238000004061 bleaching Methods 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
229960000541 cetyl alcohol Drugs 0.000 description 1
230000008859 change Effects 0.000 description 1
229920000457 chlorinated polyvinyl chloride Polymers 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
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238000007906 compression Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
230000007547 defect Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000000593 degrading effect Effects 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
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239000003085 diluting agent Substances 0.000 description 1
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238000005886 esterification reaction Methods 0.000 description 1
MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
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239000012362 glacial acetic acid Substances 0.000 description 1
YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
238000010102 injection blow moulding Methods 0.000 description 1
238000001746 injection moulding Methods 0.000 description 1
238000004898 kneading Methods 0.000 description 1
239000003077 lignite Substances 0.000 description 1
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
229910052808 lithium carbonate Inorganic materials 0.000 description 1
239000002932 luster Substances 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
150000002696 manganese Chemical class 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
229940082328 manganese acetate tetrahydrate Drugs 0.000 description 1
CESXSDZNZGSWSP-UHFFFAOYSA-L manganese(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Mn+2].CC([O-])=O.CC([O-])=O CESXSDZNZGSWSP-UHFFFAOYSA-L 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
229940043348 myristyl alcohol Drugs 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
229910052754 neon Inorganic materials 0.000 description 1
GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
ZMHZSHHZIKJFIR-UHFFFAOYSA-N octyltin Chemical compound CCCCCCCC[Sn] ZMHZSHHZIKJFIR-UHFFFAOYSA-N 0.000 description 1
239000005416 organic matter Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
238000005949 ozonolysis reaction Methods 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
239000013618 particulate matter Substances 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000001739 pinus spp. Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920006122 polyamide resin Polymers 0.000 description 1
229920002857 polybutadiene Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920005990 polystyrene resin Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
238000007348 radical reaction Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920002379 silicone rubber Polymers 0.000 description 1
239000004945 silicone rubber Substances 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
229940012831 stearyl alcohol Drugs 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000011885 synergistic combination Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
229940087291 tridecyl alcohol Drugs 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
229940036248 turpentine Drugs 0.000 description 1
239000004246 zinc acetate Substances 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Lubricants (AREA)
Detergent Compositions (AREA)

CA280,433A 1976-09-13 1977-06-13 SAVONS ET ESTERS SAPONIFIES D'ACIDES A P.M. ELEVE, DERIVES D'.alpha.-OLEFINES Expired CA1114834A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US72299076A	1976-09-13	1976-09-13
US722,990		1976-09-13

Publications (1)

Publication Number	Publication Date
CA1114834A true CA1114834A (fr)	1981-12-22

Family

ID=24904334

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA280,433A Expired CA1114834A (fr)	1976-09-13	1977-06-13	SAVONS ET ESTERS SAPONIFIES D'ACIDES A P.M. ELEVE, DERIVES D'.alpha.-OLEFINES

Country Status (1)

Country	Link
CA (1)	CA1114834A (fr)

1977
- 1977-06-13 CA CA280,433A patent/CA1114834A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-12-22	MKEX	Expiry

Publication	Publication Date	Title
US4029682A (en)	1977-06-14	Soaps and ester-soaps of α-olefin derived high molecular weight acids
US4065418A (en)	1977-12-27	High molecular weight esters of α-alkyl branched monocarboxylic acids
EP0416822B1 (fr)	1996-03-13	Compositions de plastifiants résistantes aux taches et leur méthode de préparation
WO2004069911A1 (fr)	2004-08-19	Melanges d'esters a base d'alcools ramifies et/ou d'acides ramifies, et leur utilisation en tant qu'additifs polymeres
US4038297A (en)	1977-07-26	High molecular weight monocarboxylic acids and ozonization process for their preparation
US4012357A (en)	1977-03-15	Resinous compositions containing plasticizers comprising high molecular weight esters of C22+ alpha-olefin derived acids
US4283314A (en)	1981-08-11	Resin composition having improved internal and external lubricating properties employing branched chain high molecular weight ester derivatives of monocarboxylic acids
US4141866A (en)	1979-02-27	Soaps and ester-soaps of α-alkyl branched monocarboxylic acids
US3135785A (en)	1964-06-02	Di(pentaerythritol trimonocarboxylate) alkylene dicarboxylate
JPS6197248A (ja)	1986-05-15	新規のピロメリト酸エステル可塑剤および塩化ビニル組成物
CA1114834A (fr)	1981-12-22	SAVONS ET ESTERS SAPONIFIES D'ACIDES A P.M. ELEVE, DERIVES D'.alpha.-OLEFINES
US4283310A (en)	1981-08-11	P.V.C. Compositions for extrusion moulding
JP2642059B2 (ja)	1997-08-20	Ｐｖｃ加工用熱安定剤としての亜鉛メルカプト酸のポリオールエステル
GB1560766A (en)	1980-02-06	Soaps esters-soaps and resin compositions containing them
US3267062A (en)	1966-08-16	Ester lactones as plasticizers in polyvinyl chloride compositions
US4104232A (en)	1978-08-01	Halogen-containing resin composition
JP3463841B2 (ja)	2003-11-05	プロピレン重合体組成物
US20040102555A1 (en)	2004-05-27	Overbased metal carbonate/carboxylate microemulsions and halogen-containing polymers containing same
US5153342A (en)	1992-10-06	Stain-resistant plasticizer compositions and method of making same
CN100362047C (zh)	2008-01-16	高碱性金属碳酸盐/羧酸盐微乳液和包括它的含卤素聚合物
EP0002329A1 (fr)	1979-06-13	Compositions du chlorure de polyvinyl plastifié
US3069377A (en)	1962-12-18	Halogenated polyvinyl resin composition plasticized with a mixed ester of a polyhydric alcohol
JP3440584B2 (ja)	2003-08-25	塩化ビニル系樹脂用安定化助剤組成物
JPS614748A (ja)	1986-01-10	塩化ビニル樹脂組成物
EP0039878B1 (fr)	1983-12-28	Procédé de préparation d'esters mixtes de l'acide phtalique