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WO2013004265A1 - Revêtement de surface comprenant un plastifiant à base de citrates - Google Patents

Revêtement de surface comprenant un plastifiant à base de citrates Download PDF

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Publication number
WO2013004265A1
WO2013004265A1 PCT/EP2011/061108 EP2011061108W WO2013004265A1 WO 2013004265 A1 WO2013004265 A1 WO 2013004265A1 EP 2011061108 W EP2011061108 W EP 2011061108W WO 2013004265 A1 WO2013004265 A1 WO 2013004265A1
Authority
WO
WIPO (PCT)
Prior art keywords
layer
pvc
citrate
surface covering
composition according
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.)
Ceased
Application number
PCT/EP2011/061108
Other languages
English (en)
Inventor
Larisa ALEKSANDROVA
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.)
Tarkett GDL SA
Original Assignee
Tarkett GDL SA
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.)
Filing date
Publication date
Application filed by Tarkett GDL SA filed Critical Tarkett GDL SA
Priority to EP11729411.6A priority Critical patent/EP2726545A1/fr
Priority to RU2014102917/05A priority patent/RU2578146C2/ru
Priority to PCT/EP2011/061108 priority patent/WO2013004265A1/fr
Publication of WO2013004265A1 publication Critical patent/WO2013004265A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/11—Esters; Ether-esters of acyclic polycarboxylic acids
    • 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

Definitions

  • the present invention relates to a composition of a surface covering layer, the composition comprising a citrate- based plasticizer and also relates to a method to produce a surface covering comprising such a layer.
  • VOCs emissions are also due to other plasticizers such as dibenzoate plasticizers, thermal stabilizers, viscosity reducers and other additives, which are commonly used in surface covering layer compositions.
  • a barrier layer within the surface covering or a varnish layer generally a polyurethane (PU) layer, applied on the top surface of the surface covering.
  • PU polyurethane
  • the present invention aims to provide a composition for a surface covering layer, a surface covering comprising such a layer, and a method to produce such a surface covering that do not have the drawbacks of the prior art.
  • the invention aims to provide a surface covering layer and a surface covering with suitable level of stiffness and very low VOCs emission.
  • the present invention relates to a PVC-based composition of a surface covering layer, said composition comprising at least one PVC resin, at least one non phthalate- based plasticizer generating VOCs and/or at least one additive generating VOCs, said composition further comprises at least one citrate-based plasticizer.
  • the PVC-based composition may comprise one, or a combination, of any of the following characteristics:
  • the citrate-based plasticizer is selected from the group consisting in triethyl citrate (TEC) , tributyl citrate (TBC) , acetyl tributyl citrate (ATBC) , acetyl triethyl citrate (ATEC) and acetyl tri 2-ethyl-hexyl citrate (ATEHC) .
  • TEC triethyl citrate
  • TBC tributyl citrate
  • ATBC acetyl tributyl citrate
  • ATEC acetyl triethyl citrate
  • ATEHC acetyl tri 2-ethyl-hexyl citrate
  • citrate-based plasticizer represents between 8 and 72 phr
  • the non phthalate-based plasticizer represents between 0 and 36 phr
  • the additives represent between 0 and 15 phr
  • the non phthalate-based plasticizer is selected from the group consisting in adipates, benzoates, monobenzoates and dibenzoates, trimellitates, FAME (fatty acid methyl ester) terephthalates and cyclohexanoates ,
  • the additive is selected in the group consisting in liquid stabilizers, viscosity reducers, blowing agents, liquid kickers, antistatic agents and fire retardants,
  • the citrate-based plasticizer is acetyl tributyl citrate (ATBC)
  • the non phthalate-based plasticizer is diisononyl adipate (DINA) and isononyl benzoate (INB) .
  • the present invention relates to the use of the
  • PVC-based composition according to the invention to obtain a surface covering layer having a reduced VOCs emission.
  • the surface covering layer is a support layer, a wear layer, a saturation layer, a back foam or a top foam layer of a multiple layer surface covering .
  • the present invention relates to the use of the
  • PVC-based composition according to the invention to obtain a surface covering having a reduced VOCs emission.
  • the present invention relates to a method to produce a surface covering comprising the steps of providing a composition according to the invention, gelling the composition at a temperature comprised between 130°C and 200°C to form a film or a layer, assembling the layer to at least another layer to form a surface covering.
  • At least another layer has a composition according to the invention .
  • the present invention relates to a surface covering comprising at least one layer comprising the composition according to the invention.
  • the surface covering is a floor covering.
  • Figure 1 represents the surface covering according to the invention.
  • the surface covering according to the invention is a multilayer PVC-based surface covering comprising at least one layer having a PVC-based composition which comprises at least one PVC resin and at least one citrate-based plasticizer.
  • This composition presents the advantage of getting a layer, and thus a resilient surface covering, with sustainable reduced VOCs emission (according to ISO 19000-9) even if volatile plasticizers or volatile additives generating VOCs, such as liquid stabilizers or viscosity reducers, are used to get a layer with suitable properties, such as for example stiffness .
  • the composition of the layer according to the invention comprises at least one non phthalate-based plasticizer, preferably a plurality of non phthalate-based plasticizers.
  • These non phthalate-based plasticizers may, or not, be volatile, and may, or not, generate VOCs.
  • Non phthalate-based plasticizers should be understood as being plasticizers which are not ortho-phthalate esters .
  • the non phthalate-based plasticizers is selected from the group consisting in adipates, benzoates, monobenzoates and dibenzoates, cyclohexanoates , pyrrolidones , trimellitates , FAME (fatty acid methyl esters) terephthalates and cyclohexanoates and mixtures thereof.
  • the non phthalate-based plasticizers represent between 0 and 36 phr .
  • the adipate plasticizer may be diisononyl adipate
  • DINA dioctyl adipate
  • DOA di- (2-ethylhexyl) adipate
  • BOA benzyl octyl adipate
  • the benzoate plasticizer may be isononyl benzoate
  • the citrate-based plasticizer is a citrate ester of a primary alcohols comprising between two and eight carbon atoms .
  • the citrate-based plasticizer is selected from the group consisting in triethyl citrate (TEC) , tributyl citrate (TBC) , acetyl tributyl citrate (ATBC) , acetyl triethyl citrate (ATEC) and acetyl tri 2-ethyl-hexyl citrate (ATEHC) .
  • TEC triethyl citrate
  • TBC tributyl citrate
  • ATBC acetyl tributyl citrate
  • ATEC acetyl triethyl citrate
  • ATEHC acetyl tri 2-ethyl-hexyl citrate
  • the citrate-based plasticizer represents preferably between 8 and 72 phr .
  • the citrate-based plasticizer represents at least 20% wt of the total amount of plasticizers in the composition and the non phthalate-based plasticizer represents maximum 80% wt of the total amount of plasticizers in the composition.
  • the layer composition comprises between 20 and 30 phr of diisononyl adipate (DINA) and 20 to 30 phr of acetyl tributyl citrate (ATBC) .
  • DINA diisononyl adipate
  • ATBC acetyl tributyl citrate
  • the layer composition comprises between 13 and 17 phr of diisononyl adipate (DINA) , between 8 to 13 phr of acetyl tributyl citrate (ATBC) and between 13 and 17 phr of isononyl benzoate (INB) .
  • DINA diisononyl adipate
  • ATBC acetyl tributyl citrate
  • IOB isononyl benzoate
  • the composition may further comprise one or a plurality of additives, such as a liquid stabilizer, a viscosity reducer, a blowing agent, a liquid kicker, an antistatic agent, a fire retardant, or a mixture thereof.
  • additives may, or not, be volatile and may, or not, generate VOCs .
  • the additives may represent between 0 and 15 phr.
  • the liquid stabilizer may be for example a Ca/Zn stabilizer or a Ba/Zn stabilizer.
  • the viscosity reducer may be for example either a linear or branched paraffin or a fatty acid methyl ester.
  • the blowing agent may be for example an azodicarbonamide-based agent or baking soda.
  • the liquid kickers may be for example a mixed metal soaps, based for example on potassium or Zinc.
  • the antistatic agent may be based on polyethyleneglycolether, for example Markstat from Artek Surfin Chemicals .
  • the layer according to the invention is obtained from the composition according to the invention by gelling the composition at a temperature of between 130°C and 200°C using either gelling drums or an oven.
  • the layer according to the invention may be a film or a foam.
  • the viscosity increase thus obtained can be balanced by using an adipate-based plasticizer and a citrate-based plasticizer. By doing so, the blowing ratio and the cell structure are not affected in comparison to a layer comprising phthalate plasticizers .
  • the layer may be used as a support layer, a wear layer, a saturation layer, a back foam or a top foam layer of a multiple layer surface covering.
  • the VOCs emission is defined as the sum of VVOC (Very Volatile Organic Compound), TVOC (Total Volatile Organic Compound) and SVOC (Semi Volatile Organic Compound) . It is measured at 3 days according to a test method based on ISO 16000 using microchamber carried out in Eurofins or at 28 days according to ISO 16000-9 or ISO 16000-10.
  • the VOCs emission of the layer and of a surface covering comprising such a layer represents less then 10 yg/m 3 .
  • the use of the PVC-based composition comprising the citrate-based plasticizer allows getting a layer and a surface covering which complies with the main requirements of conventional PVC-based floor coverings comprising phthalate plasticizers, in terms of viscosity, PVC paste ageing, exudation, thermal stability, ageing ....
  • the surface covering according to the invention is either a mono-layer surface covering or a multiple layer surface covering ( Figure 1).
  • the surface covering may comprise one or a plurality of layers having a composition comprising citrate-based plasticizer with non phthalate-based plasticizers and/or additives which both may generate VOCs.
  • the plurality of layers may be assembled by calendering or by spread coating layer by layer .
  • Comparative examples are monolayer surface coverings having a composition comprising a phthalate plasticizer .
  • the PVC is Lacovyl PB 1704H from Arkema or
  • the filler is Omya BL 20 from Omya.
  • the phthalate-based plasticizer is DINP, for example Vestinol 9 from Evonik.
  • the benzoate-based plasticizer is Vestinol INB from Evonik or Benzoflex 9-88 from Eastman.
  • the viscosity reducer is fatty acid methyl ester, for example Byk-LP R 21151 from Byk-Chemie.
  • the stabilizer is Lankromark LZC 393 from Akcros .
  • composition of monolayer surface coverings examples according to the invention (SI to S3) are given in table 2.
  • the PVC is Lacovyl PB 1704H from Arkema or
  • the filler is Omya BL 20 from Omya.
  • the citrate-based plasticizer is ATBC, for example Pacizer 6412 from Patech.
  • the adipate plasticizer is DOA, for example Plastomoll DOA from BASF, or DINA, for example Plastomoll DNA from BASF.
  • the stabilizer is Lankromark LZC 393 from Akcros .
  • VOCs emissions of the comparative samples and the samples according to the invention are given in table 3.
  • the VOCs were measured at 3 days according to a test method based on ISO 16000 using microchamber carried out in Eurofins.
  • the samples S3 and S4 were tested according to ISO 16000-10.
  • the layers comprising phthalate plasticizer release a high amount of VOCs, particularly TVOCs and SVOCs.
  • the layers having a composition comprising a citrate-based plasticizer show a reduced VOCs emission.
  • Comparative example CE3 is a surface covering comprising a compact layer 1 above which is laid a back foam 2, above which is laid a saturation layer 3, above which is laid a top foam layer 4, above which is laid a wear layer 5.
  • the composition of each layers are given in table 4 in phr .
  • the characteristics of the CE3 are given in table 5.
  • Table 4 Composition of the different layers of CE3.
  • Table 5 Characteristics of a surface covering CE3.
  • Comparative example CE4 is a surface covering having the same structure and layers composition as CE3, except that the plasticizer used is a non phthalate plasticizer, i.e. castor oil plasticizer, and that the wear layer further comprises 12 phr INB, in replacement of DIBP.
  • the plasticizer used is a non phthalate plasticizer, i.e. castor oil plasticizer
  • the wear layer further comprises 12 phr INB, in replacement of DIBP.
  • the characteristics of the CE3 are given in table 6.
  • the multilayer surface covering according to the invention has the same structure as CE3 ( Figure 1) but with layers having the composition of table 7 and having the characteristics of table 8.
  • Table 7 Composition of the different layers of S5.
  • the PVC is either Pevikon P682 from Ineos, Vinnolit EP 6953 from Vinnolit, Solvin 266 SF from Solvin, Solvin 372 NA from Solvin, EP 6602 C from Vinnolit, Vinnolit E 80 TT or Vestolit B 7021 Ultra from Vestolit, Solvin 372 NA from Solvin, Vinnolit E 68 FO from Vinnolit, LG PB 1202 or a mixture thereof .
  • the phthalate-based plasticizer 1 is DOP, for example Eastman DOP from Eastman.
  • the phthalate-based plasticizer 2 is DINP for example Vestinol 9 from Evonik.
  • the phthalate-based plasticizer 3 is DIBP for example Palatinol IC from BASF.
  • the benzoate-based plasticizer is INB (isononyl monobenzoate) for example Vestinol INB from Evonik.
  • the citrate-based plasticizer is ATBC, for example Citrofol BII from Jungbunzlauer, or Pacizer 6412 from Patech.
  • the castor oil is Grindsted Soft-N-Safe from Danisco .
  • the filler is calcium carbonate Mikhart 40 from Provencale.
  • the viscosity reducer is Vegalon PB 0505 from Vega-him or Atepas 5316 from Byk-Chemie.
  • the blowing agent is an azodicarbonamide, for example Unifoam VI 40 from Hebron.
  • the stabilizer is Lankromark LZC 393 from Akcros.
  • ESBO is an Epoxidized SoyBean Oil, for example Drapex 39 from Chemtura.
  • S5 should have a VOCs emission in-between CE4 and CE3, or substantially equal to CE3 as S5 comprises a benzoate non-phtalate plasticizer which is volatile and might participate to VOCs emission.
  • S5 presents an important decrease of VOCs emission. This might be due to the structure of the layer obtained from the composition comprising the citrate-based plasticizer .

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Laminated Bodies (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Paints Or Removers (AREA)

Abstract

La présente invention concerne une composition de couche de revêtement de surface. Cette composition, qui est à base de PVC, comprend un plastifiant à base de citrates. L'invention concerne également, d'une part un revêtement de surface comprenant une telle couche, et d'autre part un procédé de production d'un tel revêtement de surface.
PCT/EP2011/061108 2011-07-01 2011-07-01 Revêtement de surface comprenant un plastifiant à base de citrates Ceased WO2013004265A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP11729411.6A EP2726545A1 (fr) 2011-07-01 2011-07-01 Revêtement de surface comprenant un plastifiant à base de citrates
RU2014102917/05A RU2578146C2 (ru) 2011-07-01 2011-07-01 Поверхностное покрытие, содержащее пластификатор на основе цитрата
PCT/EP2011/061108 WO2013004265A1 (fr) 2011-07-01 2011-07-01 Revêtement de surface comprenant un plastifiant à base de citrates

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2011/061108 WO2013004265A1 (fr) 2011-07-01 2011-07-01 Revêtement de surface comprenant un plastifiant à base de citrates

Publications (1)

Publication Number Publication Date
WO2013004265A1 true WO2013004265A1 (fr) 2013-01-10

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RU (1) RU2578146C2 (fr)
WO (1) WO2013004265A1 (fr)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015101569A1 (fr) 2014-01-03 2015-07-09 Tarkett Gdl Compositions améliorées à base de plastisol de poly(chlorure de vinyle) sans phtalate
CN106009415A (zh) * 2016-07-28 2016-10-12 无锡市凯达来塑胶有限公司 一种聚氯乙烯防静电地板
WO2017074056A1 (fr) * 2015-10-27 2017-05-04 주식회사 엘지화학 Composition de plastifiant, composition de résine et leurs procédés de préparation
WO2017183877A1 (fr) * 2016-04-22 2017-10-26 주식회사 엘지화학 Composition de plastifiant et composition de résine la comprenant
WO2017183876A1 (fr) * 2016-04-22 2017-10-26 주식회사 엘지화학 Composition de plastifiant et composition de résine la comprenant
CN107709429A (zh) * 2016-04-22 2018-02-16 株式会社Lg化学 增塑剂组合物和包含该增塑剂组合物的树脂组合物
EP3211029A4 (fr) * 2014-10-22 2018-05-23 Hanwha Chemical Corporation Composition de plastifiant comprenant du 1,4-dicarboxylate d'acide di(2-éthylhexyl)cyclonucléïque et un composé citrate, et composition de résine de chlorure de vinyle comprenant celle-ci
RU2669612C2 (ru) * 2014-04-18 2018-10-12 Таркетт Гдл Отверждаемое актиничным излучением полиуретановое покрытие для декоративных облицовочных покрытий
RU2678053C2 (ru) * 2014-04-18 2019-01-22 Таркетт Гдл Отверждаемое актиничным излучением полиуретановое покрытие для декоративных облицовочных покрытий
WO2019063130A1 (fr) 2017-09-27 2019-04-04 Proviron Holding N.V. Procédé de préparation de mélanges d'esters d'acides gras époxydés
WO2023281945A1 (fr) * 2021-07-06 2023-01-12 Dic株式会社 Composition de plastifiant pour résine de chlorure de vinyle, plastisol et revêtement à base de ceux-ci

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GB2569608B (en) 2017-12-21 2022-10-26 Altro Ltd Plasticiser composition
KR102710486B1 (ko) * 2018-11-22 2024-09-27 애경케미칼주식회사 가소제 조성물 및 이를 이용한 수지 조성물

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US20100298477A1 (en) * 2007-12-21 2010-11-25 Godwin Allen D Co-Plasticizer Systems
WO2010071717A1 (fr) * 2008-12-18 2010-06-24 Exxonmobil Chemical Patents Inc. Compositions de polymères comprenant des téréphtalates

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2014375294B2 (en) * 2014-01-03 2018-10-04 Tarkett Gdl Improved phtalate-free polyvinyl chloride plastisol compositions
CN105874005A (zh) * 2014-01-03 2016-08-17 塔吉特Gdl公司 改进的无邻苯二甲酸酯的聚氯乙烯增塑溶胶组合物
EP4056647A1 (fr) 2014-01-03 2022-09-14 Tarkett GDL Compositions améliorées de plastisol de chlorure de polyvinyle sans phtalate
EP3090023B1 (fr) 2014-01-03 2022-05-04 Tarkett GDL Revêtements de surface décoratifs de compositions améliorées à base de plastisol de poly(chlorure de vinyle) sans phtalate
WO2015101569A1 (fr) 2014-01-03 2015-07-09 Tarkett Gdl Compositions améliorées à base de plastisol de poly(chlorure de vinyle) sans phtalate
RU2675542C2 (ru) * 2014-01-03 2018-12-19 Таркетт Гдл Улучшенные безфталатные поливинилхлоридные пластизолевые композиции
US10030119B2 (en) 2014-01-03 2018-07-24 Tarkett Gdl Phtalate-free polyvinyl chloride plastisol compositions
RU2678053C2 (ru) * 2014-04-18 2019-01-22 Таркетт Гдл Отверждаемое актиничным излучением полиуретановое покрытие для декоративных облицовочных покрытий
RU2669612C2 (ru) * 2014-04-18 2018-10-12 Таркетт Гдл Отверждаемое актиничным излучением полиуретановое покрытие для декоративных облицовочных покрытий
EP3211029A4 (fr) * 2014-10-22 2018-05-23 Hanwha Chemical Corporation Composition de plastifiant comprenant du 1,4-dicarboxylate d'acide di(2-éthylhexyl)cyclonucléïque et un composé citrate, et composition de résine de chlorure de vinyle comprenant celle-ci
WO2017074056A1 (fr) * 2015-10-27 2017-05-04 주식회사 엘지화학 Composition de plastifiant, composition de résine et leurs procédés de préparation
US10590260B2 (en) 2015-10-27 2020-03-17 Lg Chem, Ltd. Plasticizer composition, resin composition, and methods for preparing same
CN107709429A (zh) * 2016-04-22 2018-02-16 株式会社Lg化学 增塑剂组合物和包含该增塑剂组合物的树脂组合物
WO2017183877A1 (fr) * 2016-04-22 2017-10-26 주식회사 엘지화학 Composition de plastifiant et composition de résine la comprenant
EP3293226A4 (fr) * 2016-04-22 2018-05-02 LG Chem, Ltd. Composition de plastifiant et composition de résine la comprenant
CN107849299A (zh) * 2016-04-22 2018-03-27 株式会社Lg化学 增塑剂组合物和包含该增塑剂组合物的树脂组合物
EP3293225A4 (fr) * 2016-04-22 2018-05-09 LG Chem, Ltd. Composition de plastifiant et composition de résine la comprenant
WO2017183876A1 (fr) * 2016-04-22 2017-10-26 주식회사 엘지화학 Composition de plastifiant et composition de résine la comprenant
US11407882B2 (en) 2016-04-22 2022-08-09 Lg Chem, Ltd. Plasticizer composition and resin composition including the same
US11186702B2 (en) 2016-04-22 2021-11-30 Lg Chem, Ltd. Plasticizer composition and resin composition including the same
CN106009415A (zh) * 2016-07-28 2016-10-12 无锡市凯达来塑胶有限公司 一种聚氯乙烯防静电地板
US10858611B2 (en) 2017-09-27 2020-12-08 Proviron Holding N.V. Process for preparing mixtures of epoxidized fatty acid esters
WO2019063130A1 (fr) 2017-09-27 2019-04-04 Proviron Holding N.V. Procédé de préparation de mélanges d'esters d'acides gras époxydés
WO2023281945A1 (fr) * 2021-07-06 2023-01-12 Dic株式会社 Composition de plastifiant pour résine de chlorure de vinyle, plastisol et revêtement à base de ceux-ci
JPWO2023281945A1 (fr) * 2021-07-06 2023-01-12
JP7384324B2 (ja) 2021-07-06 2023-11-21 Dic株式会社 塩化ビニル樹脂用可塑剤組成物、プラスチゾル及びその塗膜

Also Published As

Publication number Publication date
RU2014102917A (ru) 2015-08-10
EP2726545A1 (fr) 2014-05-07
RU2578146C2 (ru) 2016-03-20

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