WO2017215747A1 - 2-ocytlester as plasticizer - Google Patents
2-ocytlester as plasticizer Download PDFInfo
- Publication number
- WO2017215747A1 WO2017215747A1 PCT/EP2016/063741 EP2016063741W WO2017215747A1 WO 2017215747 A1 WO2017215747 A1 WO 2017215747A1 EP 2016063741 W EP2016063741 W EP 2016063741W WO 2017215747 A1 WO2017215747 A1 WO 2017215747A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition according
- acid
- octyl
- alcohol
- carboxylic acid
- Prior art date
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- 239000004014 plasticizer Substances 0.000 title claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 94
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 60
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 claims abstract description 54
- 150000002148 esters Chemical class 0.000 claims abstract description 49
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 46
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 16
- 229920001971 elastomer Polymers 0.000 claims description 20
- 239000005060 rubber Substances 0.000 claims description 20
- 239000004800 polyvinyl chloride Substances 0.000 claims description 13
- -1 2-octyl Chemical group 0.000 claims description 10
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 10
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 10
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 10
- 229920000459 Nitrile rubber Polymers 0.000 claims description 8
- 229920002367 Polyisobutene Polymers 0.000 claims description 8
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 8
- 229920001084 poly(chloroprene) Polymers 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 8
- 229920003051 synthetic elastomer Polymers 0.000 claims description 8
- 239000005061 synthetic rubber Substances 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 7
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 7
- FFMCDXKXXCDOTF-UHFFFAOYSA-N dioctan-2-yl butanedioate Chemical group CCCCCCC(C)OC(=O)CCC(=O)OC(C)CCCCCC FFMCDXKXXCDOTF-UHFFFAOYSA-N 0.000 claims description 7
- GCODXQZNEMRCBU-UHFFFAOYSA-N dioctan-2-yl decanedioate Chemical compound CCCCCCC(C)OC(=O)CCCCCCCCC(=O)OC(C)CCCCCC GCODXQZNEMRCBU-UHFFFAOYSA-N 0.000 claims description 7
- 239000000194 fatty acid Substances 0.000 claims description 7
- 229930195729 fatty acid Natural products 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- 150000004665 fatty acids Chemical class 0.000 claims description 6
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 6
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 5
- HUGXNORHVOECNM-UHFFFAOYSA-N 3-chloro-2-methylprop-1-ene;2-methylbuta-1,3-diene Chemical compound CC(=C)CCl.CC(=C)C=C HUGXNORHVOECNM-UHFFFAOYSA-N 0.000 claims description 4
- CHGJJXYCZVFOGE-UHFFFAOYSA-N Octan-2-yl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)CCCCCC CHGJJXYCZVFOGE-UHFFFAOYSA-N 0.000 claims description 4
- 239000005062 Polybutadiene Substances 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 4
- 229920005549 butyl rubber Polymers 0.000 claims description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 4
- 229920002681 hypalon Polymers 0.000 claims description 4
- OMJRVNYAQYMXFR-UHFFFAOYSA-N octan-2-yl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(C)CCCCCC OMJRVNYAQYMXFR-UHFFFAOYSA-N 0.000 claims description 4
- 229940049964 oleate Drugs 0.000 claims description 4
- 229920002857 polybutadiene Polymers 0.000 claims description 4
- 229920001195 polyisoprene Polymers 0.000 claims description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
- 239000005642 Oleic acid Substances 0.000 claims description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- RYIAYRWETMHJKM-UHFFFAOYSA-N dioctan-2-yl octanedioate Chemical compound C(CCCCCCC(=O)OC(C)CCCCCC)(=O)OC(C)CCCCCC RYIAYRWETMHJKM-UHFFFAOYSA-N 0.000 claims description 3
- NLRRFBDZLUBGSA-UHFFFAOYSA-N dioctan-2-yl pentanedioate Chemical compound CCCCCCC(C)OC(=O)CCCC(=O)OC(C)CCCCCC NLRRFBDZLUBGSA-UHFFFAOYSA-N 0.000 claims description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 3
- MIEBBHYETAOCSS-UHFFFAOYSA-N octan-2-yl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC(C)CCCCCC MIEBBHYETAOCSS-UHFFFAOYSA-N 0.000 claims description 3
- LKKNEKWLXFNDDM-UHFFFAOYSA-N octan-2-yl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC(C)CCCCCC LKKNEKWLXFNDDM-UHFFFAOYSA-N 0.000 claims description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 3
- 239000011347 resin Substances 0.000 claims description 3
- 229920005989 resin Polymers 0.000 claims description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 2
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 claims description 2
- 239000005639 Lauric acid Substances 0.000 claims description 2
- 235000021360 Myristic acid Nutrition 0.000 claims description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims description 2
- 235000021314 Palmitic acid Nutrition 0.000 claims description 2
- 235000021355 Stearic acid Nutrition 0.000 claims description 2
- 239000001361 adipic acid Substances 0.000 claims description 2
- 235000011037 adipic acid Nutrition 0.000 claims description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 2
- RTUMJAGKSDIHOW-UHFFFAOYSA-N dioctan-2-yl hexanedioate Chemical compound CCCCCCC(C)OC(=O)CCCCC(=O)OC(C)CCCCCC RTUMJAGKSDIHOW-UHFFFAOYSA-N 0.000 claims description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 2
- 235000021313 oleic acid Nutrition 0.000 claims description 2
- 239000008117 stearic acid Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 125000001931 aliphatic group Chemical group 0.000 description 13
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- SAOKZLXYCUGLFA-UHFFFAOYSA-N bis(2-ethylhexyl) adipate Chemical compound CCCCC(CC)COC(=O)CCCCC(=O)OCC(CC)CCCC SAOKZLXYCUGLFA-UHFFFAOYSA-N 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 3
- 125000002843 carboxylic acid group Chemical group 0.000 description 3
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-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
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 2
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 2
- 229960003656 ricinoleic acid Drugs 0.000 description 2
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000001384 succinic acid Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- WGTJPUQKXZQJTB-UHFFFAOYSA-N 2-ethyl-2-hexylhexanedioic acid Chemical compound CCCCCCC(CC)(C(O)=O)CCCC(O)=O WGTJPUQKXZQJTB-UHFFFAOYSA-N 0.000 description 1
- NPSJHQMIVNJLNN-UHFFFAOYSA-N 2-ethylhexyl 4-nitrobenzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=C([N+]([O-])=O)C=C1 NPSJHQMIVNJLNN-UHFFFAOYSA-N 0.000 description 1
- 239000004808 2-ethylhexylester Substances 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229910001651 emery Inorganic materials 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- BTFJIXJJCSYFAL-UHFFFAOYSA-N icosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0016—Plasticisers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
Definitions
- the present invention relates to a composition
- a composition comprising at least one ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol; and use of the at least one ester as plasticizer in thermoplastic polymer compositions.
- Plasticizers can be modified by the usage of plasticizers. Flexible, plastic masses can be obtained thereby.
- the amount of plasticizers can be so high that the PVC compositions can be processed as paste (Gachter/Muller,
- WO 2014/209644 Al discloses self-wetting adhesive compositions.
- JP 2012-020984 A discloses ester derivatives and cosmetic containing the ester derivatives, external preparation, coating material and ink composition.
- thermoplastic polymer composition with improved properties and additionally (ii) a plasticizer with improved properties used in thermoplastic polymer compositions.
- esters of 2-octanol which is obtainable from castor oil have excellent plasticizing properties. Additionally, the esters of 2- octanol have a surprisingly good compatibility with the polymers as defined herein. With said esters good plasticizing and low temperature properties of thermoplastic polymer compositions are obtained. Also exceptional is the stability of the esters to hydrolysis which is distinctly higher than that of plasticizer usually used in the state of the art.
- the present invention provides a composition comprising:
- At least one carboxylic acid ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol;
- thermoplastic polymer (b) at least one thermoplastic polymer.
- a further aspect of the invention relates to a use of at least one ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol, as plasticizer, preferably in a composition as defined herein.
- a further aspect of the invention relates to a use of at least one ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol, as viscosity reducing agent, preferably in a composition as defined herein.
- the at least one carboxylic acid comprises at least one, preferably at least two, preferably at least three, preferably at least four, preferably at least five, preferably at least six carboxylic acid groups, preferably 1 to 6 carboxylic acid groups, preferably 1 or 2 carboxylic acid groups.
- the at least one carboxylic acid is selected from the group consisting of a mono-, di-, tri-, tetra-, penta-, hexa- and polycarboxylic acid and any mixture thereof.
- the at least one carboxylic acid is a CI to C30 carboxylic acid, preferably a C2 to C20 carboxylic acid, preferably a C4 to C18 carboxylic acid, preferably a C4, C5, C6, C7, C8, C9, CIO, Cl l, C12, C13, C14, C15, C16, C17 or C18 carboxylic acid, preferably a C4, C5, C8, C9, CIO, C12, C14, C16, or C18 carboxylic acid.
- Cx carboxylic acid means that the carboxylic acid comprises x carbon atom(s), including the carbon atom(s) of the carboxyl group(s).
- a C4 carboxylic acid is preferably succinic acid (C 4 H 6 O 4 ).
- the at least one carboxylic acid is a saturated or unsaturated carboxylic acid.
- the at least one carboxylic acid is an aliphatic and/or aromatic carboxylic acid.
- the at least one carboxylic acid is a linear or branched carboxylic acid.
- the unsaturated carboxylic acid comprises at least one, preferably at least two, preferably at least three, preferably 1 to 6, preferably 1, 2, 3, 4, 5, or 6 double bounds.
- the at least one carboxylic acid comprises a saturated or unsaturated chain, by which the carboxyl groups are preferably linked.
- the at least one carboxylic acid comprises a linear or branched chain, by which the carboxyl groups are preferably linked.
- the at least one carboxylic acid comprises an aliphatic and/or aromatic chain, by which the carboxyl groups are preferably linked.
- the at least one carboxylic acid comprises a saturated or unsaturated, linear or branched aliphatic chain and/or ring.
- the at least one carboxylic acid comprises additionally or alternatively at least one aromatic ring.
- the carboxylic acid has an aliphatic or aromatic structure which is branched or unbranched and comprises from 1 to 30 carbon atoms, more preferably from 2 to 20 carbon atoms, particularly preferably from 4 to 18 carbon atoms, including the carbon atoms of the one or more carboxyl groups.
- the carbon atoms are bound directly to one another via single or double bonds in the aliphatic or aromatic structure.
- the aliphatic structure preferably has solely single bonds between the carbon atoms.
- the at least one carboxylic acid comprises an carbon chain, by which the carboxyl groups are preferably linked, wherein preferably at least one, preferably at least two, preferably at least three, preferably 1 to 6, preferably at most half of the carbon atoms, preferably 1, 2, 3, 4, 5 or 6 carbon atoms are substituted by the same or different hetero atoms, wherein the hetero atoms are preferably selected form nitrogen, sulfur and oxygen.
- the carbon chain is free of heteroatoms.
- the at least one carboxylic acid consists of at least one, preferably exactly one saturated or unsaturated, aliphatic and/or aromatic, linear or branched hydrocarbon chain and/or ring and at least one carboxylic acid group COOH.
- the present invention relates to a composition according to the present invention, wherein the at least one carboxylic acid is selected from the group consisting of monocarboxylic acids, dicarboxylic acids and any mixture thereof.
- the present invention relates to a composition according to the present invention, wherein the monocarboxylic acids are selected from the group consisting of fatty acids.
- the monocarboxylic acids preferably the fatty acids are obtainable from renewable materials.
- the at least one monocarboxylic acid is an unsaturated fatty acid, a saturated fatty acid or any mixture thereof.
- the saturated fatty acid is preferably a saturated C12 to C18 fatty acid.
- the unsaturated fatty acid is preferably an unsaturated C12 to C18 fatty acid with one, two, three, four, five or six double bonds, preferably with exactly one double bond.
- the at least one monocarboxylic acid is stearic acid, palmitic acid, oleic acid, lauric acid, myristic acid and any mixture thereof.
- the at least one dicarboxylic acid is an alkane dicarboxylic acid, an alkene dicarboxylic acid or any mixture thereof.
- the alkane dicarboxylic acid is preferably a C2 to CIO alkane dicarboxylic acid.
- the alkene dicarboxylic acid is preferably a C4 to CIO alkene dicarboxylic acid with one, two or three double bonds.
- the at least one dicarboxylic acid is an alkane dicarboxylic acid.
- the present invention relates to a composition according to the present invention, wherein the dicarboxylic acids are selected from the group consisting of succinic acid, azelaic acid, sebacic acid, glutaric acid, suberic acid, adipic acid and any mixture thereof.
- the dicarboxylic acids are selected from the group consisting of succinic acid, azelaic acid, sebacic acid, glutaric acid, suberic acid, adipic acid and any mixture thereof.
- succinic acid, azelaic acid and/or sebacic acid are produced from a renewable material.
- succinic acid is produced by fermentation of carbohydrates, preferably of starch.
- azelaic acid is produced by ozonolysis of oleic acid.
- sebacic acid is produced by pyrolysis of castor oil, preferably of ricinoleic acid or derivatives thereof.
- the at least one carboxylic acid ester is obtainable by reacting at least one carboxylic acid with 2-octanol and at least one further alcohol.
- the 2-octanol is reacted with the at least one carboxylic acid in form of a product, preferably obtained from a technical production process, which product comprises the 2-octanol in an amount of at least 50 % by weight, preferably at least 70 % by weight, preferably at least 80 % by weight, preferably at least 90% by weight, preferably at least 99 % by weight (based on the total weight of the product).
- the present invention relates to a composition according to the present invention, wherein at least 50 mol-%, preferably at least 70 mol-%, preferably at least 80 mol-%, preferably at least 90 mol-%, preferably at least 99 mol-%, preferably 100 mol-% of the at least one alcohol is 2-octanol (based on the total amount of alcohols reacted with the at least one carboxylic acid).
- the at least one further alcohol comprises at least one, preferably at least two, preferably at least three, preferably at least four, preferably at least five, preferably at least six hydroxyl groups, preferably 1 to 6 hydroxyl groups, preferably 1, 2, 3, 4, 5, or 6 hydroxyl groups, preferably exactly one hydroxyl group.
- the at least one further alcohol is a CI to C30 alcohol, preferably a C2 to C20 alcohol, preferably a C8 to C12 alcohol, preferably a C8, C9, CIO, Cl l or C12 alcohol, preferably a C8, CIO, or C12 alcohol.
- the at least one further alcohol is a saturated or unsaturated alcohol.
- the at least one further alcohol is an aliphatic and/or aromatic alcohol.
- the at least one further alcohol is a linear or branched alcohol.
- the unsaturated at least one further alcohol comprises at least one, preferably at least two, preferably at least three, preferably 1 to 6, preferably 1, 2, 3, 4, 5, or 6 double bounds.
- the at least one further alcohol comprises a saturated or unsaturated chain.
- the at least one further alcohol comprises a linear or branched chain.
- the at least one further alcohol comprises a saturated or unsaturated chain which is linear or branched.
- the at least one further alcohol comprises a saturated or unsaturated, linear or branched aliphatic chain and/or ring.
- the at least one further alcohol comprises additionally or alternatively at least one aromatic ring.
- the further alcohol has an aliphatic or aromatic structure which is branched or linear and comprises from 1 to 30 carbon atoms, more preferably from 8 to 12 carbon atoms.
- the carbon atoms are bound directly to one another via single or double bonds in the aliphatic or aromatic structure.
- the aliphatic structure preferably has solely single bonds between the carbon atoms.
- the at least one further alcohol comprises an carbon chain, wherein preferably at least one, preferably at least two, preferably at least three, preferably 1 to 6, preferably at most half of the carbon atoms, preferably 1, 2, 3, 4, 5 or 6 carbon atoms are substituted by the same or different hetero atoms, wherein the hetero atoms are preferably selected form nitrogen, sulfur and oxygen.
- the carbon chain is free of heteroatoms.
- the at least one further alcohol consists of at least one, preferably exactly one saturated or unsaturated, aliphatic and/or aromatic, linear or branched hydrocarbon chain and/or ring and at least one hydroxyl group OH.
- the at least one further alcohol is an alcohol produced from renewable materials.
- the at least one further alcohol is preferably an aliphatic, preferably an alkyl, alcohol, preferably with 8, 10 or 12 carbon atoms, preferably a C8, CIO or C12 alkyl monoalcohol, or any mixture thereof.
- the at least one carboxylic acid ester is obtainable by reacting a mono-, di-, tri-, tetra-, penta-, hexa- or polycarboxylic acid with one, two, three, four, five, six or more different alcohols, wherein the one or one of the two, three, four, five, six or more different alcohols is 2-octanol.
- the alcohol different from 2-octanol is preferably an aliphatic, preferably an alkyl, alcohol, preferably with 8, 10 or 12 carbon atoms, preferably a C8, CIO or C12 alkyl monoalcohol, or any mixture thereof.
- the alcohol different from 2-octanol is producible from renewable materials.
- the at least one carboxylic acid ester is obtainable by reacting at least one, preferably at least two, preferably at least three, preferably at least four, preferably at least five, preferably at least six, preferably (n - 3), preferably (n - 2), preferably (n - 1), preferably n carboxyl groups of the at least one carboxylic acid having n carboxyl groups.
- all carboxyl groups of the at least one carboxylic acid have been reacted, i.e. esterfied, with 2-octanol and optionally with at least one further alcohol.
- the at least one carboxylic acid ester is obtainable by reacting a monocarboxylic acid with an alcohol, wherein the alcohol is 2-octanol.
- the at least one carboxylic acid ester is preferably obtainable by reacting a dicarboxylic acid with two different alcohols, wherein one of the two different alcohols is 2-octanol.
- the at least one carboxylic acid ester is preferably obtainable by reacting a dicarboxylic acid with exactly one alcohol, wherein the alcohol is 2-octanol.
- the at least one ester consists of
- the composition comprises at least two, preferably at least three different esters according to the present invention. More preferably, the composition comprises exactly one or two, preferably exactly one ester according to the present invention.
- the present invention relates to a composition according to the present invention, wherein the at least one ester is selected from the group consisting of di-2-octyl succinate, di-2-octyl sebacate, di-2-octyl azelate, di-2-octyl glutarate, di-2-octyl suberate, di- 2-octyl adipate, 2-octyl stearate, 2-octyl palmitate, 2-octyl oleate, 2-octyl laurate, 2-octyl myristate and any mixture thereof.
- the at least one ester is selected from the group consisting of di-2-octyl succinate, di-2-octyl sebacate, di-2-octyl azelate, di-2-octyl glutarate, di-2-octyl suberate, di- 2-octyl adipate, 2-octy
- the at least one ester is selected from the group consisting of di-2-octyl succinate, di-2-octyl sebacate, di-2-octyl azelate, 2-octyl stearate, 2- octyl palmitate, 2-octyl oleate and any mixture thereof.
- the at least one ester is selected from the group consisting of di-2-octyl succinate, di-2-octyl sebacate, di-2-octyl azelate and any mixture thereof.
- these esters can exclusively be obtained from renewable materials.
- the present invention relates to a composition according to the present invention, wherein the at least one alcohol and optionally the at least one carboxylic acid have been obtained from a renewable source.
- the 2-octanol is produced by the pyrolysis of castor oil, preferably of ricinoleic acid or derivatives thereof. Castor oil is a renewable source for 2-octanol.
- the present invention relates to a composition according to the present invention, wherein the at least one ester has a high stability to hydrolysis.
- the at least one ester has a higher stability to hydrolysis than an ester comprising the same carboxylic acid component and a different alcohol component, wherein the alcohol component is preferably selected from a group consisting of 1-octanol and 2-ethylhexanol.
- the present invention relates to a composition according to the present invention, wherein the at least one thermoplastic polymer is selected from the group consisting of polyvinyl chloride (PVC), at least one rubber and any mixture thereof.
- the at least one thermoplastic polymer is polyvinyl chloride (PVC).
- the polyvinyl chloride (PVC) has a molecular weight (M w ) of 20.000 to 300.000 g/mol, preferably 100.000 to 200.000 g/mol.
- the present invention relates to a composition according to the present invention, wherein the at least one rubber is a synthetic rubber.
- the synthetic rubber has a molecular weight (M w ) of 50.000 to 500.000 g/mol, preferably 200.000 to 300.000 g/mol.
- the present invention relates to a composition according to the present invention, wherein the synthetic rubber is selected from the group consisting of acrylonitrile butadiene rubber (NBR), polybutadiene rubber (BR), chloro isobutylene isoprene rubber (CIIR), chlorosulfonated polyethylene (CSM), chloroprene rubber (CR), polyisobutylene rubber (PIB), polyisoprene rubber (IR), fluorinated rubber (FKM) and any mixture thereof.
- NBR acrylonitrile butadiene rubber
- BR polybutadiene rubber
- CIIR chloro isobutylene isoprene rubber
- CSM chlorosulfonated polyethylene
- CR chloroprene rubber
- PIB polyisobutylene rubber
- IR fluorinated rubber
- FKM fluorinated rubber
- the present invention relates to a composition according to the present invention, wherein the content of polymers of methacrylate and/or acrylate is less than 50 % by weight.
- the composition is preferably free of methacrylate and/or acrylate in monomer and/or polymer form.
- the composition comprises
- At least one carboxylic acid ester selected from the group consisting of di-2- octyl succinate, di-2-octyl sebacate, di-2-octyl azelate, di-2-octyl glutarate, di- 2-octyl suberate, 2-octyl stearate, 2-octyl palmitate, 2-octyl oleate, 2-octyl laurate, 2-octyl myristate and any mixture thereof; and
- thermoplastic polymer selected from the group consisting of polyvinyl chloride (PVC), at least one rubber and any mixture thereof
- the synthetic rubber is selected from the group consisting of acrylonitrile butadiene rubber (NBR), polybutadiene rubber (BR), chloro isobutylene isoprene rubber (CIIR), chlorosulfonated polyethylene (CSM), chloroprene rubber (CR), polyisobutylene rubber (PIB), polyisoprene rubber (IR), fluorinated rubber (FKM) and any mixture thereof.
- composition comprises
- the composition comprises at least two, preferably at least three different plasticizers.
- the composition comprises exactly two different plasticizers.
- the composition comprises the at least one ester and an epoxy plasticizer as plasticizers.
- the composition further comprises at least one fatty acid ester which is different from the at least one ester according to the present invention, preferably an epoxidized soybean oil.
- the composition further comprises a stabilizing agent, preferably a Sn stabilizer, and/or a lubricant.
- a stabilizing agent preferably a Sn stabilizer, and/or a lubricant.
- the composition is solid at a temperature of 22 °C.
- the composition is free of a cross-linked polymer, preferably a cross-linked thermoplastic polymer, or comprises a cross-linked polymer, preferably a cross-linked thermoplastic polymer, in an amount of 50 % by weight or less, preferably 40 % by weight or less, preferably 30 % by weight or less, preferably 10% by weight or less, preferably 5% by weight or less, preferably 1 % by weight or less (based on the total weight of polymers in the composition).
- the at least one rubber is cross-linked, preferably vulcanized.
- the PVC is not cross-linked.
- the present invention relates to a composition according to the present invention, wherein the at least one ester (a) is present in an amount of 0.1 to 60 % by weight (based on the total weight of the composition).
- the at least one ester (a) is present in an amount of 10 to 50 % by weight, preferably 20 to 40 % by weight (based on the total weight of the composition).
- the present invention relates to a composition according to the present invention, wherein the at least one polymer (b) is present in an amount of at least 40 % by weight (based on the total amount of the composition).
- the at least one polymer (b) is present in an amount of at least 50 % by weight, preferably at least 60 % by weight, preferably at least 80 % by weight (based on the total amount of the composition).
- the present invention relates to a composition according to the present invention, wherein the at least one ester (a) is present in an amount of 100 parts or less per 100 parts of resin.
- the at least one ester (a) is present in an amount of 80 parts or less, preferably 60 to 20 parts per 100 parts of resin.
- the present invention relates to a composition according to the present invention, wherein the at least one ester (a) is present in an amount of 100 parts or less per 100 parts of the thermoplastic polymer (b).
- the at least one ester (a) is present in an amount of 80 parts or less, preferably 60 to 20 parts per 100 parts of the thermoplastic polymer (b).
- the present invention relates to a use of at least one ester obtainable by reacting at least one carboxylic acid and at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol, as plasticizer, preferably in a composition as defined herein.
- the at least one ester is used for plasticizing at least one thermoplastic polymer, preferably polyvinyl chloride (PVC), at least one rubber and any mixture thereof, wherein the at least one rubber is preferably a synthetic rubber, wherein the synthetic rubber is preferably selected from the group consisting of acrylonitrile butadiene rubber (NBR), polybutadiene rubber (BR), chloro isobutylene isoprene rubber (CIIR), chlorosulfonated polyethylene (CSM), chloroprene rubber (CR), polyisobutylene rubber (PIB), polyisoprene rubber (IR), fluorinated rubber (FKM) and any mixture thereof.
- the at least one ester is used for plasticizing polyvinyl chloride (PVC).
- the present invention relates to a use of at least one ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol, as viscosity reducing agent, preferably in a composition as defined herein.
- any technical feature, either alone or in combination with one or more further technical features, disclosed in context with the composition according to the present invention or according to one or more preferred embodiments is also preferably a technical feature for specifying the uses according to the present invention and/or one or more of their preferred embodiments.
- any technical feature, either alone or in combination with one or more further technical features, disclosed in context with the composition according to the present invention or according to one or more preferred embodiments is also preferably a technical feature for specifying the uses according to the present invention and/or one or more of their preferred embodiments.
- the alcohol, the carboxylic acid (each in the amount as listed in table 1, below) and 0.3 g tin- (Il)-oxalate (Goldschmidt) were heated under nitrogen atmosphere.
- the ester reaction starts at about 170 °C with the production of water. After 3 hours the produced water was removed by applying vacuum and the vacuum was reduced within 4 hours up to about 15 mbar. The final reaction temperature was reached at about 230 °C. After having reached an acid number of less than 1, the excessive alcohol was distilled and the ester was cooled to a temperature of 90 °C, washed with 300 ml water for removing the catalyst, dried and filtered with 2 g bleaching earth (Tonsil, Sudchemie) being added.
- the produced esters have the following properties/characteristics as shown in table 2, below.
- Table 4 shows that by using the plasticizers of Examples 4 to 6, namely di-2-octyl succinate, di-2-octyl sebacate and di-2-octyl azelate, the same properties of PVC were obtained as by di-2-ethylhexyladipate (DOA), used an industrial standard.
- DOA di-2-ethylhexyladipate
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Abstract
The present invention relates to a composition comprising at least one ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol; and use of the at least one ester as plasticizer in thermoplastic polymer compositions.
Description
2-OCYTLESTER AS PLASTICIZER
The present invention relates to a composition comprising at least one ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol; and use of the at least one ester as plasticizer in thermoplastic polymer compositions.
BACKGROUND OF THE INVENTION
Material properties of plastics can be modified by the usage of plasticizers. Flexible, plastic masses can be obtained thereby. In PVC compositions the amount of plasticizers can be so high that the PVC compositions can be processed as paste (Gachter/Muller,
Kunststoffadditive, 2nd edition, publisher: Carl Hanser Verlag). Recently, many companies attach importance to the usage of additives based on renewable materials. Some companies offer "green plasticizers" partially or completely produced from renewable materials, e.g. GRINDSTED® SOFT-N-SAFE of Danisco (http://www.danisco.com/softnsafe/doc/ snsbrochure.pdf) or isosorbid esters as disclosed in DE69906708T2. In addition to monocarboxylic acids, dicarboxylic acids are sold, which can be produced from renewable materials, such as fatty acids, succinic acid, sebacic acid and azelaic acid. The selection of renewable alcohols is nowadays restricted to n-C8 to n-C18 fatty alcohols, ethanol, 1,2- propandiol and butanol.
WO 2014/209644 Al discloses self-wetting adhesive compositions.
JP 2012-020984 A discloses ester derivatives and cosmetic containing the ester derivatives, external preparation, coating material and ink composition.
It was an object to the present invention to solve the aforementioned problems and preferably to provide (i) a thermoplastic polymer composition with improved properties and additionally (ii) a plasticizer with improved properties used in thermoplastic polymer compositions.
SUMMARY OF THE INVENTION
It was an unexpected finding of the inventors that the esters of 2-octanol which is obtainable from castor oil have excellent plasticizing properties. Additionally, the esters of 2- octanol have a surprisingly good compatibility with the polymers as defined herein. With said esters good plasticizing and low temperature properties of thermoplastic polymer compositions are obtained. Also exceptional is the stability of the esters to hydrolysis which is distinctly higher than that of plasticizer usually used in the state of the art.
Thus, to solve the aforementioned problems, the present invention provides a composition comprising:
(a) at least one carboxylic acid ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol; and
(b) at least one thermoplastic polymer.
A further aspect of the invention relates to a use of at least one ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol, as plasticizer, preferably in a composition as defined herein.
A further aspect of the invention relates to a use of at least one ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol, as viscosity reducing agent, preferably in a composition as defined herein.
The technical problem has been, in particular, solved by the subject-matter of the independent claims. Preferred embodiments are the subject-matter of the dependent claims.
DETAILED DESCRIPTION OF THE INVENTION
Before the present invention is described in detail below, it is to be understood that this invention is not limited to the particular methodology, protocols and reagents described herein as these may vary. It is also to be understood that the terminology used herein is for the purpose of describing particular embodiments only, and is not intended to limit the scope of the present invention which will be limited only by the appended claims. Unless defined otherwise, all technical and scientific terms used herein have the same meanings as commonly understood by one of ordinary skill in the art.
In the following passages different aspects of the invention are defined in more detail. Each aspect so defined may be combined with any other aspect or aspects unless clearly indicated to the contrary. In particular, any feature indicated as being preferred or advantageous may be combined with any other feature or features indicated as being preferred or advantageous.
Some documents are cited throughout the text of this specification. Each of the documents cited herein (including all patents, patent applications, scientific publications, manufacturer's specifications, instructions, DIN norms etc.), whether supra or infra, are hereby incorporated by reference in their entirety. Nothing herein is to be construed as an admission that the invention is not entitled to antedate such disclosure by virtue of prior invention.
In the following definitions of some terms are provided. These terms will, in each instance of its use, in the remainder of the specification have the respectively defined meaning and preferred meanings.
With the term "and/or" all members of a corresponding group are connected to each other alternatively, partially or completely commutatively. For instance, the term "A, B and/or C" is understood as "A or B or C or (A and B) or (A and C) or (B and C) or (A and B and O".
Preferably, the at least one carboxylic acid comprises at least one, preferably at least two, preferably at least three, preferably at least four, preferably at least five, preferably at least six carboxylic acid groups, preferably 1 to 6 carboxylic acid groups, preferably 1 or 2
carboxylic acid groups. Preferably, the at least one carboxylic acid is selected from the group consisting of a mono-, di-, tri-, tetra-, penta-, hexa- and polycarboxylic acid and any mixture thereof.
Preferably, the at least one carboxylic acid is a CI to C30 carboxylic acid, preferably a C2 to C20 carboxylic acid, preferably a C4 to C18 carboxylic acid, preferably a C4, C5, C6, C7, C8, C9, CIO, Cl l, C12, C13, C14, C15, C16, C17 or C18 carboxylic acid, preferably a C4, C5, C8, C9, CIO, C12, C14, C16, or C18 carboxylic acid. In the context with the present invention the term "Cx carboxylic acid" means that the carboxylic acid comprises x carbon atom(s), including the carbon atom(s) of the carboxyl group(s). Accordingly, a C4 carboxylic acid is preferably succinic acid (C4H6O4).
Preferably, the at least one carboxylic acid is a saturated or unsaturated carboxylic acid. Preferably, the at least one carboxylic acid is an aliphatic and/or aromatic carboxylic acid. Preferably, the at least one carboxylic acid is a linear or branched carboxylic acid. Preferably, the unsaturated carboxylic acid comprises at least one, preferably at least two, preferably at least three, preferably 1 to 6, preferably 1, 2, 3, 4, 5, or 6 double bounds.
Preferably, the at least one carboxylic acid comprises a saturated or unsaturated chain, by which the carboxyl groups are preferably linked. Preferably, the at least one carboxylic acid comprises a linear or branched chain, by which the carboxyl groups are preferably linked. Preferably, the at least one carboxylic acid comprises an aliphatic and/or aromatic chain, by which the carboxyl groups are preferably linked.
Preferably, the at least one carboxylic acid comprises a saturated or unsaturated, linear or branched aliphatic chain and/or ring. Preferably, the at least one carboxylic acid comprises additionally or alternatively at least one aromatic ring.
In a preferred embodiment, the carboxylic acid has an aliphatic or aromatic structure which is branched or unbranched and comprises from 1 to 30 carbon atoms, more preferably from 2 to 20 carbon atoms, particularly preferably from 4 to 18 carbon atoms, including the carbon atoms of the one or more carboxyl groups. The carbon atoms are bound directly to one another via single or double bonds in the aliphatic or aromatic structure. The aliphatic structure preferably has solely single bonds between the carbon atoms.
Preferably, the at least one carboxylic acid comprises an carbon chain, by which the carboxyl groups are preferably linked, wherein preferably at least one, preferably at least two, preferably at least three, preferably 1 to 6, preferably at most half of the carbon atoms, preferably 1, 2, 3, 4, 5 or 6 carbon atoms are substituted by the same or different hetero atoms, wherein the hetero atoms are preferably selected form nitrogen, sulfur and oxygen. Preferably, the carbon chain is free of heteroatoms. Preferably, the at least one carboxylic acid consists of at least one, preferably exactly one saturated or unsaturated, aliphatic and/or aromatic, linear or branched hydrocarbon chain and/or ring and at least one carboxylic acid group COOH.
Preferably, the present invention relates to a composition according to the present invention, wherein the at least one carboxylic acid is selected from the group consisting of monocarboxylic acids, dicarboxylic acids and any mixture thereof.
Preferably, the present invention relates to a composition according to the present invention, wherein the monocarboxylic acids are selected from the group consisting of fatty acids. Preferably, the monocarboxylic acids, preferably the fatty acids are obtainable from renewable materials. Preferably, the at least one monocarboxylic acid is an unsaturated fatty acid, a saturated fatty acid or any mixture thereof. The saturated fatty acid is preferably a saturated C12 to C18 fatty acid. The unsaturated fatty acid is preferably an unsaturated C12 to C18 fatty acid with one, two, three, four, five or six double bonds, preferably with exactly one double bond. Preferably, the at least one monocarboxylic acid is stearic acid, palmitic acid, oleic acid, lauric acid, myristic acid and any mixture thereof.
Preferably, the at least one dicarboxylic acid is an alkane dicarboxylic acid, an alkene dicarboxylic acid or any mixture thereof. The alkane dicarboxylic acid is preferably a C2 to CIO alkane dicarboxylic acid. The alkene dicarboxylic acid is preferably a C4 to CIO alkene dicarboxylic acid with one, two or three double bonds. Preferably, the at least one dicarboxylic acid is an alkane dicarboxylic acid.
Preferably, the present invention relates to a composition according to the present invention, wherein the dicarboxylic acids are selected from the group consisting of succinic acid, azelaic acid, sebacic acid, glutaric acid, suberic acid, adipic acid and any mixture
thereof.
Preferably, succinic acid, azelaic acid and/or sebacic acid are produced from a renewable material. Preferably, succinic acid is produced by fermentation of carbohydrates, preferably of starch. Preferably, azelaic acid is produced by ozonolysis of oleic acid. Preferably, sebacic acid is produced by pyrolysis of castor oil, preferably of ricinoleic acid or derivatives thereof.
Preferably, the at least one carboxylic acid ester is obtainable by reacting at least one carboxylic acid with 2-octanol and at least one further alcohol.
Preferably, the 2-octanol is reacted with the at least one carboxylic acid in form of a product, preferably obtained from a technical production process, which product comprises the 2-octanol in an amount of at least 50 % by weight, preferably at least 70 % by weight, preferably at least 80 % by weight, preferably at least 90% by weight, preferably at least 99 % by weight (based on the total weight of the product).
Preferably, the present invention relates to a composition according to the present invention, wherein at least 50 mol-%, preferably at least 70 mol-%, preferably at least 80 mol-%, preferably at least 90 mol-%, preferably at least 99 mol-%, preferably 100 mol-% of the at least one alcohol is 2-octanol (based on the total amount of alcohols reacted with the at least one carboxylic acid).
Preferably, the at least one further alcohol comprises at least one, preferably at least two, preferably at least three, preferably at least four, preferably at least five, preferably at least six hydroxyl groups, preferably 1 to 6 hydroxyl groups, preferably 1, 2, 3, 4, 5, or 6 hydroxyl groups, preferably exactly one hydroxyl group.
Preferably, the at least one further alcohol is a CI to C30 alcohol, preferably a C2 to C20 alcohol, preferably a C8 to C12 alcohol, preferably a C8, C9, CIO, Cl l or C12 alcohol, preferably a C8, CIO, or C12 alcohol.
Preferably, the at least one further alcohol is a saturated or unsaturated alcohol. Preferably, the at least one further alcohol is an aliphatic and/or aromatic alcohol. Preferably,
the at least one further alcohol is a linear or branched alcohol. Preferably, the unsaturated at least one further alcohol comprises at least one, preferably at least two, preferably at least three, preferably 1 to 6, preferably 1, 2, 3, 4, 5, or 6 double bounds.
Preferably, the at least one further alcohol comprises a saturated or unsaturated chain. Preferably, the at least one further alcohol comprises a linear or branched chain. Preferably, the at least one further alcohol comprises a saturated or unsaturated chain which is linear or branched.
Preferably, the at least one further alcohol comprises a saturated or unsaturated, linear or branched aliphatic chain and/or ring. Preferably, the at least one further alcohol comprises additionally or alternatively at least one aromatic ring.
In a preferred embodiment, the further alcohol has an aliphatic or aromatic structure which is branched or linear and comprises from 1 to 30 carbon atoms, more preferably from 8 to 12 carbon atoms. The carbon atoms are bound directly to one another via single or double bonds in the aliphatic or aromatic structure. The aliphatic structure preferably has solely single bonds between the carbon atoms.
Preferably, the at least one further alcohol comprises an carbon chain, wherein preferably at least one, preferably at least two, preferably at least three, preferably 1 to 6, preferably at most half of the carbon atoms, preferably 1, 2, 3, 4, 5 or 6 carbon atoms are substituted by the same or different hetero atoms, wherein the hetero atoms are preferably selected form nitrogen, sulfur and oxygen. Preferably, the carbon chain is free of heteroatoms. Preferably, the at least one further alcohol consists of at least one, preferably exactly one saturated or unsaturated, aliphatic and/or aromatic, linear or branched hydrocarbon chain and/or ring and at least one hydroxyl group OH.
Preferably, the at least one further alcohol is an alcohol produced from renewable materials. The at least one further alcohol is preferably an aliphatic, preferably an alkyl, alcohol, preferably with 8, 10 or 12 carbon atoms, preferably a C8, CIO or C12 alkyl monoalcohol, or any mixture thereof.
Preferably, the at least one carboxylic acid ester is obtainable by reacting a mono-, di-,
tri-, tetra-, penta-, hexa- or polycarboxylic acid with one, two, three, four, five, six or more different alcohols, wherein the one or one of the two, three, four, five, six or more different alcohols is 2-octanol. Preferably, the alcohol different from 2-octanol is preferably an aliphatic, preferably an alkyl, alcohol, preferably with 8, 10 or 12 carbon atoms, preferably a C8, CIO or C12 alkyl monoalcohol, or any mixture thereof. Preferably, the alcohol different from 2-octanol is producible from renewable materials.
Preferably, the at least one carboxylic acid ester is obtainable by reacting at least one, preferably at least two, preferably at least three, preferably at least four, preferably at least five, preferably at least six, preferably (n - 3), preferably (n - 2), preferably (n - 1), preferably n carboxyl groups of the at least one carboxylic acid having n carboxyl groups. Preferably, all carboxyl groups of the at least one carboxylic acid have been reacted, i.e. esterfied, with 2-octanol and optionally with at least one further alcohol.
Preferably, the at least one carboxylic acid ester is obtainable by reacting a monocarboxylic acid with an alcohol, wherein the alcohol is 2-octanol. Alternatively, the at least one carboxylic acid ester is preferably obtainable by reacting a dicarboxylic acid with two different alcohols, wherein one of the two different alcohols is 2-octanol. Alternatively, the at least one carboxylic acid ester is preferably obtainable by reacting a dicarboxylic acid with exactly one alcohol, wherein the alcohol is 2-octanol.
Preferably, the at least one ester consists of
(i) a mono-, di-, tri-, tetra-, penta-, hexa- or polycarboxylic acid
component, and
(ii) 2-octanol as alcohol component.
Preferably, the composition comprises at least two, preferably at least three different esters according to the present invention. More preferably, the composition comprises exactly one or two, preferably exactly one ester according to the present invention.
Preferably, the present invention relates to a composition according to the present invention, wherein the at least one ester is selected from the group consisting of di-2-octyl succinate, di-2-octyl sebacate, di-2-octyl azelate, di-2-octyl glutarate, di-2-octyl suberate, di- 2-octyl adipate, 2-octyl stearate, 2-octyl palmitate, 2-octyl oleate, 2-octyl laurate, 2-octyl
myristate and any mixture thereof. Preferably, the at least one ester is selected from the group consisting of di-2-octyl succinate, di-2-octyl sebacate, di-2-octyl azelate, 2-octyl stearate, 2- octyl palmitate, 2-octyl oleate and any mixture thereof. Preferably, the at least one ester is selected from the group consisting of di-2-octyl succinate, di-2-octyl sebacate, di-2-octyl azelate and any mixture thereof. Preferably, these esters can exclusively be obtained from renewable materials.
Preferably, the present invention relates to a composition according to the present invention, wherein the at least one alcohol and optionally the at least one carboxylic acid have been obtained from a renewable source. Preferably, the 2-octanol is produced by the pyrolysis of castor oil, preferably of ricinoleic acid or derivatives thereof. Castor oil is a renewable source for 2-octanol.
Preferably, the present invention relates to a composition according to the present invention, wherein the at least one ester has a high stability to hydrolysis. Preferably, the at least one ester has a higher stability to hydrolysis than an ester comprising the same carboxylic acid component and a different alcohol component, wherein the alcohol component is preferably selected from a group consisting of 1-octanol and 2-ethylhexanol.
Preferably, the present invention relates to a composition according to the present invention, wherein the at least one thermoplastic polymer is selected from the group consisting of polyvinyl chloride (PVC), at least one rubber and any mixture thereof. Preferably, the at least one thermoplastic polymer is polyvinyl chloride (PVC).
Preferably, the polyvinyl chloride (PVC) has a molecular weight (Mw) of 20.000 to 300.000 g/mol, preferably 100.000 to 200.000 g/mol.
Preferably, the present invention relates to a composition according to the present invention, wherein the at least one rubber is a synthetic rubber.
Preferably, the synthetic rubber has a molecular weight (Mw) of 50.000 to 500.000 g/mol, preferably 200.000 to 300.000 g/mol.
Preferably, the present invention relates to a composition according to the present
invention, wherein the synthetic rubber is selected from the group consisting of acrylonitrile butadiene rubber (NBR), polybutadiene rubber (BR), chloro isobutylene isoprene rubber (CIIR), chlorosulfonated polyethylene (CSM), chloroprene rubber (CR), polyisobutylene rubber (PIB), polyisoprene rubber (IR), fluorinated rubber (FKM) and any mixture thereof.
Preferably, the present invention relates to a composition according to the present invention, wherein the content of polymers of methacrylate and/or acrylate is less than 50 % by weight. Alternatively, the composition is preferably free of methacrylate and/or acrylate in monomer and/or polymer form.
Preferably, the composition comprises
(a) at least one carboxylic acid ester selected from the group consisting of di-2- octyl succinate, di-2-octyl sebacate, di-2-octyl azelate, di-2-octyl glutarate, di- 2-octyl suberate, 2-octyl stearate, 2-octyl palmitate, 2-octyl oleate, 2-octyl laurate, 2-octyl myristate and any mixture thereof; and
(b) at least one thermoplastic polymer selected from the group consisting of polyvinyl chloride (PVC), at least one rubber and any mixture thereof, the synthetic rubber is selected from the group consisting of acrylonitrile butadiene rubber (NBR), polybutadiene rubber (BR), chloro isobutylene isoprene rubber (CIIR), chlorosulfonated polyethylene (CSM), chloroprene rubber (CR), polyisobutylene rubber (PIB), polyisoprene rubber (IR), fluorinated rubber (FKM) and any mixture thereof.
More preferably, the composition comprises
(a) at least one carboxylic acid ester selected from the group consisting of di-2- octyl succinate, di-2-octyl sebacate, di-2-octyl azelate and any mixture thereof; and
(b) polyvinyl chloride (PVC).
Preferably, the composition comprises at least two, preferably at least three different plasticizers. Preferably, the composition comprises exactly two different plasticizers.
Preferably, the composition comprises the at least one ester and an epoxy plasticizer as plasticizers.
Preferably, the composition further comprises at least one fatty acid ester which is different from the at least one ester according to the present invention, preferably an epoxidized soybean oil.
Preferably, the composition further comprises a stabilizing agent, preferably a Sn stabilizer, and/or a lubricant.
Preferably, the composition is solid at a temperature of 22 °C.
Preferably, the composition is free of a cross-linked polymer, preferably a cross-linked thermoplastic polymer, or comprises a cross-linked polymer, preferably a cross-linked thermoplastic polymer, in an amount of 50 % by weight or less, preferably 40 % by weight or less, preferably 30 % by weight or less, preferably 10% by weight or less, preferably 5% by weight or less, preferably 1 % by weight or less (based on the total weight of polymers in the composition).
Preferably, the at least one rubber is cross-linked, preferably vulcanized. Preferably, the PVC is not cross-linked.
Preferably, the present invention relates to a composition according to the present invention, wherein the at least one ester (a) is present in an amount of 0.1 to 60 % by weight (based on the total weight of the composition). Preferably, the at least one ester (a) is present in an amount of 10 to 50 % by weight, preferably 20 to 40 % by weight (based on the total weight of the composition).
Preferably, the present invention relates to a composition according to the present invention, wherein the at least one polymer (b) is present in an amount of at least 40 % by weight (based on the total amount of the composition). Preferably, the at least one polymer (b) is present in an amount of at least 50 % by weight, preferably at least 60 % by weight, preferably at least 80 % by weight (based on the total amount of the composition).
Preferably, the present invention relates to a composition according to the present invention, wherein the at least one ester (a) is present in an amount of 100 parts or less per 100 parts of resin. Preferably, the at least one ester (a) is present in an amount of 80 parts or less, preferably 60 to 20 parts per 100 parts of resin.
Preferably, the present invention relates to a composition according to the present invention, wherein the at least one ester (a) is present in an amount of 100 parts or less per 100 parts of the thermoplastic polymer (b). Preferably, the at least one ester (a) is present in an amount of 80 parts or less, preferably 60 to 20 parts per 100 parts of the thermoplastic polymer (b).
In a second aspect the present invention relates to a use of at least one ester obtainable by reacting at least one carboxylic acid and at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol, as plasticizer, preferably in a composition as defined herein.
Preferably, the at least one ester is used for plasticizing at least one thermoplastic polymer, preferably polyvinyl chloride (PVC), at least one rubber and any mixture thereof, wherein the at least one rubber is preferably a synthetic rubber, wherein the synthetic rubber is preferably selected from the group consisting of acrylonitrile butadiene rubber (NBR), polybutadiene rubber (BR), chloro isobutylene isoprene rubber (CIIR), chlorosulfonated polyethylene (CSM), chloroprene rubber (CR), polyisobutylene rubber (PIB), polyisoprene rubber (IR), fluorinated rubber (FKM) and any mixture thereof. Most preferred, the at least one ester is used for plasticizing polyvinyl chloride (PVC).
In a third aspect the present invention relates to a use of at least one ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol, as viscosity reducing agent, preferably in a composition as defined herein.
Preferably, any technical feature, either alone or in combination with one or more further technical features, disclosed in context with the composition according to the present invention or according to one or more preferred embodiments is also preferably a technical feature for specifying the uses according to the present invention and/or one or more of their preferred embodiments.
Various modifications and variations of the invention will be apparent to those skilled in the art without departing from the scope of the invention. Although the invention has been described in connection with specific preferred embodiments, it should be understood that the invention as claimed should not be unduly limited to such specific embodiments.
The following examples are merely illustrative of the present invention and should not be construed to limit the scope of the invention as indicated by the appended claims in any way.
EXAMPLES
I. Production of esters
The alcohol, the carboxylic acid (each in the amount as listed in table 1, below) and 0.3 g tin- (Il)-oxalate (Goldschmidt) were heated under nitrogen atmosphere. The ester reaction starts at about 170 °C with the production of water. After 3 hours the produced water was removed by applying vacuum and the vacuum was reduced within 4 hours up to about 15 mbar. The final reaction temperature was reached at about 230 °C. After having reached an acid number of less than 1, the excessive alcohol was distilled and the ester was cooled to a temperature of 90 °C, washed with 300 ml water for removing the catalyst, dried and filtered with 2 g bleaching earth (Tonsil, Sudchemie) being added.
Table 1
Table 2
The acid numbers were determined pursuant to DIN EN ISO 2114.
II. Production of PVC compositions
The components as listed in table 3, below, were mixed in the amount (each in parts per weight) as listed in table 3, below, and rolled in a rolling mill at a temperature of 185 °C for 5 minutes. Pressed plates with a thickness of 3mm were produced from the rolled sheets at a temperature of 150 °C in a hydraulic press (50 bar for 9 min; 300 bar for 1 min).
Table 3
di-2-octyl 40 - - - succinate
(Example 4)
di-2-octyl - 40 - - sebacate
(Example 5)
di-2-octyl azelate - - 40 -
(Example 6)
di-2- - - - 40
ethylhexyladipate
(abbreviated as
DOA; Plastomoll
DOA, BASF)
The transmission, the Shore hardness D and other properties of the pressed plates were measured (see table 4, below).
Table 4
Table 4 shows that by using the plasticizers of Examples 4 to 6, namely di-2-octyl succinate, di-2-octyl sebacate and di-2-octyl azelate, the same properties of PVC were obtained as by di-2-ethylhexyladipate (DOA), used an industrial standard.
III. Stability to hydrolysis of esters
In order to determining the stability to hydrolysis, 150 g ester and 15 g water were stored in closed containers at 90 °C. During the storage the esters hydrolyzed and free acid molecules were obtained. Accordingly, the acid numbers of each ester were tracked over days (see tables 5 and 6). As shown in tables 5 and 6 the 2-octyl esters have a higher stability to hydrolysis than the corresponding 1-octyl or 2-ethylhexyl ester.
i6
Table 5
n.d. = not determined
The acid numbers were determined pursuant to DIN EN ISO 2114.
Claims
1. Composition comprising:
(a) at least one carboxylic acid ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol; and
(b) at least one thermoplastic polymer.
2. Composition according to claim 1 , wherein the at least one alcohol and optionally the at least one carboxylic acid have been obtained from a renewable source.
3. Composition according to claims 1 or 2, wherein the at least one ester has a high stability to hydrolysis.
4. Composition according to any one of the preceding claims, wherein at least 50 mol-% of the at least one alcohol is 2-octanol (based on the total amount of alcohols reacted with the at least one carboxylic acid).
5. Composition according to any one of the preceding claims, wherein the at least one thermoplastic polymer is selected from the group consisting of polyvinyl chloride (PVC), at least one rubber and any mixture thereof.
6. Composition according claim 5, wherein the at least one rubber is a synthetic rubber.
7. Composition according to claim 6, wherein the synthetic rubber is selected from the group consisting of acrylonitrile butadiene rubber (NBR), polybutadiene rubber (BR), chloro isobutylene isoprene rubber (CIIR), chlorosulfonated polyethylene (CSM), chloroprene rubber (CR), polyisobutylene rubber (PIB), polyisoprene rubber (IR), fluorinated rubber (FKM) and any mixture thereof.
8. Composition according to any one of the preceding claims, wherein the content of polymers of methacrylate and/or acrylate is less than 50 % by weight.
i8
9. Composition according to any one of the preceding claims, wherein the at least one carboxylic acid is selected from the group consisting of monocarboxylic acids, dicarboxylic acids and any mixture thereof.
10. Composition according to any one of the preceding claims, wherein the
monocarboxylic acids are selected from the group consisting of fatty acids, preferably stearic acid, palmitic acid, oleic acid, lauric acid, myristic acid and any mixture thereof.
11. Composition according to any one of the preceding claims, wherein the dicarboxylic acids are selected from the group consisting of succinic acid, azelaic acid, sebacic acid, glutaric acid, suberic acid, adipic acid and any mixture thereof.
12. Composition according to any one of the preceding claims, wherein the at least one ester is selected from the group consisting of di-2-octyl succinate, di-2-octyl sebacate, di-2-octyl azelate, di-2-octyl glutarate, di-2-octyl suberate, di-2-octyl adipate, 2-octyl stearate, 2-octyl palmitate, 2-octyl oleate, 2-octyl laurate, 2-octyl myristate and any mixture thereof.
13. Composition according to any one of the preceding claims, wherein the at least one ester (a) is present in an amount of 0.1 to 60 % by weight (based on the total weight of the composition).
14. Composition according to any one of the preceding claims, wherein the at least one polymer (b) is present in an amount of at least 40 % by weight (based on the total amount of the composition).
15. Composition according to any one of the preceding claims, wherein the at least one ester (a) is present in an amount of 100 part or less per 100 part of resin.
16. Use of at least one ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol, as plasticizer, preferably in a composition according to any one of claims 1 to 15.
Use of at least one ester obtainable by reacting at least one carboxylic acid with at least one alcohol, wherein at least one of the at least one alcohol is 2-octanol, as viscosity reducing agent, preferably in a composition according to any one of claims 1 to 15.
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US10988605B2 (en) | 2017-11-14 | 2021-04-27 | Avery Dennison Corporation | PVC compositions, films, laminates and related methods |
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US10988605B2 (en) | 2017-11-14 | 2021-04-27 | Avery Dennison Corporation | PVC compositions, films, laminates and related methods |
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