CA2745255C - Plasticizer preparations with good gelling properties - Google Patents
Plasticizer preparations with good gelling properties Download PDFInfo
- Publication number
- CA2745255C CA2745255C CA2745255A CA2745255A CA2745255C CA 2745255 C CA2745255 C CA 2745255C CA 2745255 A CA2745255 A CA 2745255A CA 2745255 A CA2745255 A CA 2745255A CA 2745255 C CA2745255 C CA 2745255C
- Authority
- CA
- Canada
- Prior art keywords
- phthalate
- plasticizer
- weight
- preparations
- moiety
- Prior art date
- 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 - Fee Related
Links
- 239000004014 plasticizer Substances 0.000 title claims abstract description 65
- 238000002360 preparation method Methods 0.000 title claims abstract description 38
- -1 benzoic ester Chemical class 0.000 claims abstract description 36
- 229920003023 plastic Polymers 0.000 claims abstract description 19
- 239000004033 plastic Substances 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims description 21
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 9
- 229920001944 Plastisol Polymers 0.000 claims description 8
- 239000004999 plastisol Substances 0.000 claims description 8
- 239000000853 adhesive Substances 0.000 claims description 4
- 230000001070 adhesive effect Effects 0.000 claims description 4
- 239000000565 sealant Substances 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000000576 coating method Methods 0.000 claims description 3
- 125000002704 decyl 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])* 0.000 claims description 2
- 239000000976 ink Substances 0.000 claims description 2
- 239000003973 paint Substances 0.000 claims description 2
- 125000001400 nonyl group Chemical group [H]C([*])([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])[H] 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 abstract description 5
- 239000004800 polyvinyl chloride Substances 0.000 description 27
- 229920000915 polyvinyl chloride Polymers 0.000 description 26
- 239000007787 solid Substances 0.000 description 16
- IRIAEXORFWYRCZ-UHFFFAOYSA-N Butylbenzyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IRIAEXORFWYRCZ-UHFFFAOYSA-N 0.000 description 12
- 238000007614 solvation Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- UDKSLGIUCGAZTK-UHFFFAOYSA-N phenyl pentadecane-1-sulfonate Chemical compound CCCCCCCCCCCCCCCS(=O)(=O)OC1=CC=CC=C1 UDKSLGIUCGAZTK-UHFFFAOYSA-N 0.000 description 10
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 10
- MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 description 8
- 238000003860 storage Methods 0.000 description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 239000004803 Di-2ethylhexylphthalate Substances 0.000 description 4
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Chemical compound CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 4
- ZVFDTKUVRCTHQE-UHFFFAOYSA-N Diisodecyl phthalate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C ZVFDTKUVRCTHQE-UHFFFAOYSA-N 0.000 description 4
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 229920000747 poly(lactic acid) Polymers 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 229960002380 dibutyl phthalate Drugs 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000005498 phthalate group Chemical class 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 239000004709 Chlorinated polyethylene Substances 0.000 description 2
- 229920000181 Ethylene propylene rubber Polymers 0.000 description 2
- 229920000459 Nitrile rubber Polymers 0.000 description 2
- 239000006057 Non-nutritive feed additive Substances 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- DLAHAXOYRFRPFQ-UHFFFAOYSA-N dodecyl benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1 DLAHAXOYRFRPFQ-UHFFFAOYSA-N 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 229920005558 epichlorohydrin rubber Polymers 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229920006168 hydrated nitrile rubber Polymers 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- JQCXWCOOWVGKMT-UHFFFAOYSA-N phthalic acid diheptyl ester Natural products CCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC JQCXWCOOWVGKMT-UHFFFAOYSA-N 0.000 description 2
- 229920001084 poly(chloroprene) Polymers 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000005033 polyvinylidene chloride Substances 0.000 description 2
- 239000006077 pvc stabilizer Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 231100000615 substance of very high concern Toxicity 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- UADWUILHKRXHMM-UHFFFAOYSA-N 2-ethylhexyl benzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1 UADWUILHKRXHMM-UHFFFAOYSA-N 0.000 description 1
- BUWRPJINRQFQPN-UHFFFAOYSA-N 3,5,5-trimethylhexyl benzoate Chemical compound CC(C)(C)CC(C)CCOC(=O)C1=CC=CC=C1 BUWRPJINRQFQPN-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004609 Impact Modifier Substances 0.000 description 1
- 229920012485 Plasticized Polyvinyl chloride Polymers 0.000 description 1
- 241000223080 Sweet potato virus C Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000004600 biostabiliser Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical class OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
- CUSUFTNOPPMGBK-UHFFFAOYSA-N decyl benzoate Chemical class CCCCCCCCCCOC(=O)C1=CC=CC=C1 CUSUFTNOPPMGBK-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 229940106055 dodecyl benzoate Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- BAZQYVYVKYOAGO-UHFFFAOYSA-M loxoprofen sodium hydrate Chemical compound O.O.[Na+].C1=CC(C(C([O-])=O)C)=CC=C1CC1C(=O)CCC1 BAZQYVYVKYOAGO-UHFFFAOYSA-M 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- VUHMHACHBVTPMF-UHFFFAOYSA-N nonyl benzoate Chemical class CCCCCCCCCOC(=O)C1=CC=CC=C1 VUHMHACHBVTPMF-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000010094 polymer processing Methods 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
-
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/04—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08L27/06—Homopolymers or copolymers of vinyl chloride
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10168454A EP2404961A1 (de) | 2010-07-05 | 2010-07-05 | Weichmacherzubereitungen mit guten Geliereigenschaften |
| EP10168454.6 | 2010-07-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2745255A1 CA2745255A1 (en) | 2012-01-05 |
| CA2745255C true CA2745255C (en) | 2017-06-20 |
Family
ID=42813179
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2745255A Expired - Fee Related CA2745255C (en) | 2010-07-05 | 2011-07-05 | Plasticizer preparations with good gelling properties |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US8524817B2 (enExample) |
| EP (2) | EP2404961A1 (enExample) |
| JP (1) | JP5794842B2 (enExample) |
| CA (1) | CA2745255C (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101460399B1 (ko) * | 2012-04-09 | 2014-11-10 | (주)엘지하우시스 | 친환경 가소제를 함유하는 생분해성 수지 조성물 및 이를 이용한 생분해성 수지 제품 |
| PL3090023T3 (pl) | 2014-01-03 | 2023-01-16 | Tarkett Gdl | Dekoracyjne pokrycia powierzchniowe z ulepszonych bezftalanowych kompozycji plastizolu poli(chlorku winylu) |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH516608A (de) | 1968-12-14 | 1971-12-15 | Ciba Geigy Ag | Verformbare Mischungen und deren Verwendung zur Herstellung von Folien und Überzügen |
| GB9607686D0 (en) | 1996-04-12 | 1996-06-12 | Exxon Chemical Patents Inc | Plastisol compostions |
| DE10217186A1 (de) * | 2002-04-18 | 2003-11-13 | Oxeno Olefinchemie Gmbh | Benzoesäureisononylester und deren Verwendung |
| DE10249912A1 (de) * | 2002-10-26 | 2004-05-06 | Oxeno Olefinchemie Gmbh | Benzoesäureisodecyclestergemische, Herstellung und deren Verwendung |
| CN101107306B (zh) | 2005-01-18 | 2012-06-20 | 埃克森美孚化学专利公司 | 在增塑剂组合物中或涉及增塑剂组合物的改进 |
| EP1873198A1 (de) | 2006-06-30 | 2008-01-02 | Lanxess Deutschland GmbH | Mischungen aus Alkylester und Benzylester von Polycarbonsäuren |
| DE102007018992A1 (de) | 2007-04-21 | 2008-10-23 | Lanxess Deutschland Gmbh | Stoffgemische auf Basis von Alkylbenzylestern |
| DE102007044689A1 (de) | 2007-09-19 | 2009-04-02 | Lanxess Deutschland Gmbh | Schnell gelierende Weichmacherzubereitungen |
| CN101990560A (zh) | 2007-12-21 | 2011-03-23 | 埃克森美孚化学专利公司 | 助增塑剂体系 |
| DE102008033834A1 (de) * | 2008-07-19 | 2010-01-21 | Lanxess Deutschland Gmbh | Weichmacherzubereitungen |
-
2010
- 2010-07-05 EP EP10168454A patent/EP2404961A1/de not_active Withdrawn
-
2011
- 2011-06-22 EP EP11170929A patent/EP2404962B1/de not_active Not-in-force
- 2011-06-24 US US13/168,079 patent/US8524817B2/en not_active Expired - Fee Related
- 2011-07-04 JP JP2011148238A patent/JP5794842B2/ja not_active Expired - Fee Related
- 2011-07-05 CA CA2745255A patent/CA2745255C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP2404962B1 (de) | 2013-01-16 |
| US8524817B2 (en) | 2013-09-03 |
| CA2745255A1 (en) | 2012-01-05 |
| JP2012012603A (ja) | 2012-01-19 |
| JP5794842B2 (ja) | 2015-10-14 |
| US20120129991A1 (en) | 2012-05-24 |
| EP2404962A1 (de) | 2012-01-11 |
| EP2404961A1 (de) | 2012-01-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20150723 |
|
| MKLA | Lapsed |
Effective date: 20200831 |