WO2015005597A1 - Caoutchouc au nitrile et son procédé de production - Google Patents

Caoutchouc au nitrile et son procédé de production Download PDF

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Publication number
WO2015005597A1
WO2015005597A1 PCT/KR2014/005543 KR2014005543W WO2015005597A1 WO 2015005597 A1 WO2015005597 A1 WO 2015005597A1 KR 2014005543 W KR2014005543 W KR 2014005543W WO 2015005597 A1 WO2015005597 A1 WO 2015005597A1
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Prior art keywords
nitrile rubber
weight
polymerization
parts
acid
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PCT/KR2014/005543
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English (en)
Korean (ko)
Inventor
이세은
류동조
한선희
안정현
전희정
조정훈
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(주) 엘지화학
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Priority claimed from KR1020140071217A external-priority patent/KR101606988B1/ko
Application filed by (주) 엘지화학 filed Critical (주) 엘지화학
Priority to CN201480001961.2A priority Critical patent/CN104507989B/zh
Priority to US14/421,205 priority patent/US9809670B2/en
Publication of WO2015005597A1 publication Critical patent/WO2015005597A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
    • C08F236/12—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated with nitriles
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
    • C08L9/02—Copolymers with acrylonitrile

Definitions

  • the present invention relates to nitrile rubber and a method for producing the same, and more particularly, to a method for producing nitrile rubber and nitrile rubber, which contributes to an excellent polymerization rate and vulcanization rate, and has properties that are advantageous for workability during vulcanization.
  • nitrile rubber is a copolymer of acrylonitrile and butadiene, and the bonding amount of acrylonitrile is between 15 and 50%, and is randomly copolymerized in various ratios.
  • the greatest advantage of the nitrile rubber is that the oil resistance is very excellent because of the polarity of the nitrile group in the acrylonitrile, and its properties vary greatly depending on the amount of bound nitrile.
  • the oil resistance refers to the amount of bound nitrile and swelling, and the aniline point of oil (the lowest temperature at which hydrocarbons completely dissolve with the same volume of aniline, which can be measured to determine the composition of light mineral oil such as gasoline) and swelling.
  • the oil here refers to a mineral oil, that is, a petroleum hydrocarbon structure, and is generally used as lubrication or hydraulic oil.
  • nitrile rubber has excellent oil resistance and is most suitable for O-rings, V-packings, and oil seals in various fields such as industrial machinery, construction machinery, power generation equipment, automobile aircraft, etc. .
  • the usable temperature of nitrile rubber varies greatly depending on the formulation, at low temperatures of -50 to -120 ° C, especially for low temperature, the nitrile rubber is used in equipment for polar and cold regions, aircraft and the like.
  • the relatively high nitrile content is not only excellent in heat resistance and mechanical properties, but also excellent in permeability and can be used up to about 10 torr for vacuum use.
  • polymerization is carried out through low temperature emulsion polymerization, and is treated in a bale form by a coagulation process using a flocculant.
  • the demand for cold resistance of automobile parts becomes increasingly strict, the demand for low nitrile rubber increases, but the low nitrile content needs to be solved because of poor workability and slow vulcanization rate.
  • an object of the present invention is to solve the problems of the prior art, and to provide a nitrile rubber having a low nitrile content but contributing to an excellent polymerization rate and vulcanization rate, and having properties favorable to workability during vulcanization and a method of manufacturing the same. It is for.
  • the present invention comprises 18 to 32 parts by weight of at least one ⁇ , ⁇ -unsaturated nitrile monomer, and 82 to 68 parts by weight of at least one conjugated diene monomer based on 100 parts by weight of nitrile rubber,
  • a nitrile rubber characterized by having an ACN of 3 or less.
  • the present invention also encompasses emulsion polymerization of 18-32% by weight of one or more ⁇ , ⁇ -unsaturated nitrile monomers and 82-68% by weight of one or more conjugated diene monomers,
  • the present invention also provides a vulcanizable mixture containing the above-mentioned nitrile rubber and at least one crosslinking agent.
  • the present invention provides a method for producing a rubber base molding and a molding, wherein the above-mentioned nitrile rubber or vulcanizable mixture is vulcanized in a molding process to produce a molding.
  • the present invention comprises 18 to 32 parts by weight of one or more ⁇ , ⁇ -unsaturated nitrile monomers, and 82 to 68 parts by weight of one or more conjugated diene monomers based on 100 parts by weight of nitrile rubber, wherein ⁇ ACN is 3 or less It is characterized by.
  • the term “ ⁇ ACN” is used to determine the glass transition temperature and its starting and ending points using DSC according to ASTM E 1356-03 or DIN 11357-2, Based on the starting and ending points, by applying the Gordon-Taylor relationship, the ACN content for the starting and ending points can be calculated from the following equation and refers to the difference for the ACN distribution calculated from these values.
  • the ⁇ , ⁇ -unsaturated nitrile monomer may be, for example, at least one selected from acrylonitrile, methacrylonitrile, fumaronitrile, ⁇ -chloronitrile, and ⁇ -cyanoethyl acrylonitrile.
  • the ⁇ , ⁇ -unsaturated nitrile monomer may be, for example, 18 to 32 parts by weight, 18 to 29 parts by weight, 22 to 32 parts by weight, or 18 to 22 parts by weight of 100 parts by weight of the nitrile rubber.
  • the conjugated diene monomer may be, for example, one or more selected from 1,3-butadiene, 2,3-dimethyl-1,3-butadiene, 2-ethyl-1,3-butadiene, 1,3-pentadiene, and isoprene. .
  • the conjugated diene monomer may be, for example, 82 to 68 parts by weight, 82 to 71 parts by weight, 78 to 68 parts by weight, or 82 to 78 parts by weight of 100 parts by weight of the nitrile rubber.
  • the nitrile rubber may be, for example, a content change ( ⁇ AN) of ⁇ , ⁇ -unsaturated nitrile monomer during the polymerization of 3 or less, or 2 or less (see FIG. 1).
  • ⁇ AN content change
  • the nitrile rubber may have a content change ( ⁇ AN) of ⁇ , ⁇ -unsaturated nitrile monomer before the polymerization conversion of 40% or less and a change of content of ⁇ , ⁇ -unsaturated nitrile monomer after the polymerization conversion of 40% ( ⁇ AN). It may be two or less.
  • the nitrile rubber may include 0.5 to 5 parts by weight of fatty acid based on 100 parts by weight of nitrile rubber.
  • the fatty acid may be, for example, an aliphatic organic acid having 12 to 18 carbon atoms, or an aliphatic organic acid having 14 to 18 carbon atoms or 16 to 18 carbon atoms.
  • oleic acid rosin acid, lauric acid, myristic acid, palmitic acid, stearic acid, naphthalene sulfonic acid And eicosanoic acid may be used.
  • the fatty acid may include 0.5 to 5 parts by weight, or 1 to 3 parts by weight based on 100 parts by weight of nitrile rubber, and may effectively serve as an emulsifier within the above range.
  • the nitrile rubber may include 0.01 to 10 parts by weight of alkyl thiol based on 100 parts by weight of nitrile rubber.
  • the alkyl thiol contains, for example, 12 to 16 carbon atoms and at least 3 tertiary carbon atoms, and may be at least one type of sulfur bonded to one of the tertiary carbon atoms.
  • alkyl thiol examples include at least one selected from 2,2,4,6,6-pentamethylheptan-4-thiol and 2,2,4,6,6,8,8-heptamethylnonan-4-thiol. It may be.
  • the alkyl thiol may include 0.01 to 10 parts by weight, or 0.5 to 3 parts by weight based on 100 parts by weight of nitrile rubber, and may effectively serve as a molecular weight regulator within the above range.
  • the nitrile rubber may include 0.01 to 1 parts by weight of fat-soluble peroxide based on 100 parts by weight of nitrile rubber.
  • the fat-soluble peroxides are, for example, benzoyl peroxide, di-tributyl peroxide, azobisisobutyronitrile, tributyl hydroperoxide, dicumyl peroxide, t-butyl perbenzoate, cumene hydroperoxide, t-butyl At least one selected from peroctoate, methyl ethyl ketone peroxide, 2,5-dimethyl-2,5-di (t-butylperoxy) hexane and lauryl peroxide.
  • the fat-soluble peroxide may include 0.01 to 1 part by weight, or 0.01 to 0.5 part by weight based on 100 parts by weight of nitrile rubber, and may effectively serve as an initiator within the above range.
  • the present invention also encompasses emulsion polymerization of 18 to 32% by weight of one or more ⁇ , ⁇ -unsaturated nitrile monomers and 82 to 68% by weight of one or more conjugated diene monomers, and (i) the ⁇ , ⁇ -unsaturated nitrile.
  • the monomers are divided in the initial polymerization and during the polymerization, and the divided injection during the polymerization is carried out once or twice in 1.5 to 3.5 hr after the start of polymerization, and then once or twice in 4-6 hr, and (ii) fatty acid, It is a technical feature to carry out the emulsion polymerization in the presence of alkyl thiols and fat soluble peroxides.
  • the ⁇ , ⁇ -unsaturated nitrile monomer may be, for example, 40 to 85% by weight added at the beginning of the polymerization and the remainder 60 to 15% by weight may be added evenly divided during the polymerization.
  • the ⁇ , ⁇ -unsaturated nitrile monomer may be 40 to 60% by weight is added to the initial stage of polymerization and the remainder 60 to 40% by weight may be added evenly divided during the polymerization.
  • the emulsion polymerization may be performed so that the time required for reaching the polymerization conversion rate of 80% at a polymerization temperature of 5 to 25 ° C is 7 to 8 hours.
  • the emulsion polymerization may be coagulated and washed according to a conventional post-treatment procedure after terminating the polymerization at a polymerization conversion rate of 80%.
  • the coagulation may be coagulation at 50 to 100 ° C. using one or more sodium or potassium salts, and may be 5 wt% or less of calcium chloride based on the total amount of the total salt used for coagulation.
  • the sodium or potassium salt may be one or more halides, one or more nitrates or one or more sulfates of sodium or potassium.
  • the coagulation uses a mixture of two or more salts, wherein the salts are different salts of the same monovalent metal or various salts of various monovalent metals, and before or during the coagulation, Aging inhibitor may be added and washing may be performed at 50 to 90 ° C.
  • the nitrile rubber obtained according to the above-described method has a Mooney viscosity (ML (1 + 4 @ 100 ° C)) of 10 to 150 Mooney units and a Mooney stress relaxation rate (MSR) of 0.350 to In the range of 0.383, where the Mooney viscosity and Mooney stress relaxation rate are measured by a shear disc viscometer at 100 ° C. according to ISO 289-4: 2003E.
  • the nitrile rubber has a glass transition temperature (Tg) in the range of -70 ° C to + 10 ° C, where the glass transition temperature (Tg) is measured using a differential scanning calorimeter according to DIN 11357/2 or ASTM E1356-03. Can be.
  • the nitrile rubber has a T5 in vulcanization characteristic in the range of 2.1 to 2.3 min, and a vulcanization rate (Vmax) in vulcanization characteristic in the range of 62.5 to 64.3 kgf.cm, wherein the vulcanization characteristic is Monsanto MDF2000 Leo according to ASTM D5289-95. It may be what is measured on the meter.
  • a vulcanizable mixture characterized by containing the above-mentioned nitrile rubber and at least one crosslinking agent.
  • the mixture may comprise one or more additives selected from fillers, fillers, activators, ozone blockers, aging inhibitors, antioxidants, processing aids, extender oils, plasticizers, reinforcing materials and release agents.
  • the molding has a tensile strength in the range of 225 to 246 kgf / cm2, an elongation in the range of 377 to 387%, a 300% modulus in the range of 174 to 185, wherein the tensile strength, elongation, 300% modulus is DIN 53 According to 504 may be measured on a vulcanizate.
  • the moldings are for example seals, caps, hoses or diaphragms, O-ring seals, flat seals, corrugated seal rings, seal sleeves, seal caps, dust barrier caps, plug seals, insulation hoses, oil cooler hoses, intake hoses, servos (servo) may be a control hose or pump diaphragm.
  • a nitrile rubber which contributes to an excellent polymerization rate and a vulcanization rate and has properties that are advantageous for workability.
  • a nitrile rubber having a uniform monomer distribution and a lower long-chain branching ratio (see high MSR value), which not only promotes polymerization rate and processing speed but also has high vulcanization density and excellent mechanical properties.
  • the polymerization was terminated when the conversion value of the monomer was converted to the polymer by the total solid content measurement was 80%, the reaction time was a total of 8 hours. Acrylonitrile content by conversion is shown graphically in FIG. 1.
  • the coagulum was washed and dehydrated, chopped through a mixer (mixer), oven dried and sheeted in a roll to obtain a final rubber.
  • Examples 2-3 and Comparative Examples 1-7 were carried out in the same manner as in Example 1, except that the divided dose timing of acrylonitrile, the charged amount and the type and content of the molecular weight regulator were changed as shown in Table 1 below. And the same as in Example 1 above.
  • Example 1 12 parts by weight of acrylonitrile was initially added, and 4 parts of the remainder were added equally, except that 2.5 parts by weight were added at a time after 3.5 hours, 5 hours, and 6.5 hours respectively. And the same as in Example 1 above. At this time, the reaction time required until the polymerization conversion reached 80% was a total of 8 hours.
  • Example 12 parts by weight of acrylonitrile was initially added in Example 1, and the remainder was the same as in Example 1 except that 5 parts by weight were added in batches after 2.5 equal hours and 2 hours after polymerization. It was carried out. At this time, the reaction time required until the polymerization conversion reached 80% was a total of 7 hours.
  • Example 12 parts by weight of acrylonitrile was initially added in Example 1, and the same procedure as in Example 1 was carried out except that the remaining batch was added after 2.5 hr. At this time, the reaction time required until the polymerization conversion reached 80% was a total of 8 hours.
  • Example 12 parts by weight of acrylonitrile was initially added in Example 1, and the same procedure as in Example 1 was carried out except that the remaining portions were each added 5 parts by weight after 4 hours and 6 hours. In this case, the reaction time required for the polymerization conversion to reach 80% was 7.5 hours in total.
  • Example 1 acrylonitrile was initially added in 22 parts by weight, and the division was performed in the same manner as in Example 1 except that division was not performed. In this case, the reaction time required until the polymerization conversion reached 80% was a total of 7 hours.
  • Example 2 22 parts by weight of acrylonitrile was initially added in Example 1, and the separation was not performed, and the same procedure as in Example 1 was performed except that the alkyl thiol was replaced with 0.5 parts by weight of t-dodecyl mercaptan. . In this case, the reaction time required for the polymerization conversion to reach 80% was 8.3 hours in total.
  • Example 1 acrylonitrile was initially added in 22 parts by weight, and the division was not carried out, except that alkyl thiol was replaced with 0.55 parts by weight of n-octyl mercaptan. In this case, the reaction time required for the polymerization conversion to reach 80% was 7.8 hours in total.
  • Example 1 Except that the molecular weight regulator in Example 1 was replaced with 0.55 parts by weight of n-octyl mercaptan was carried out in the same manner as in Example 1. In this case, the reaction time required until the polymerization conversion reached 80% was 8.5 hours in total.
  • Example 1 Except for replacing oleic acid with rosin acid in Example 1 was carried out in the same manner as in Example 1. In this case, the reaction time required until the polymerization conversion reached 80% was 9 hours in total.
  • Mooney viscosity The Mooney viscosity of the raw polymer was measured according to DIN 53523/3 or ASTMD 1646.
  • MSR Mooney stress-relaxation rate
  • ⁇ ACN Determination of the glass transition temperature and its start and end points are determined using DSC according to ASTM E1356-03 or DIN 11357-2. Based on the measured starting and ending points, the Gordon-Taylor relationship can be applied to calculate the ACN content for the starting and ending points, and from these values the difference in the ACN distribution can be obtained.
  • Vulcanization Characteristics (MDR: Moving Die Rheometer): The vulcanization profile and its related analytical data were measured on a Monsanto MDR2000 rheometer according to ASTM D5289-95.
  • Vmax (vulcanization speed): It means the maximum torque required for 100% vulcanization.
  • Example 1 indicated by three circuits in FIG. 1), Example 3 (indicated by two circuits in FIG. 1), Comparative Example 2 (indicated by one circuit in FIG. 1), and Comparative Example 3 (indicated by batch in FIG. 1), Except that 32% by weight of acrylonitrile and 68% by weight of 1,3-butadiene were used, in particular, 27% by weight of acrylonitrile was used at the beginning of the polymerization, and 5% by weight of the acrylonitrile was replaced in equal parts. The same experiment as in Example 1, 3 and Comparative Example 2, 3 was repeated. The acrylonitrile content change with conversion during each polymerization was measured according to the N content analysis method using an element analyzer (EA) and then graphically shown in FIG. 1.
  • EA element analyzer
  • Example 1 An additional experimental example of Example 1 is shown in three times in FIG. 1, an additional experimental example of Example 3 is shown in two times in FIG. 1, an additional experimental example of Comparative Example 2 is shown in one time in FIG. Additional experimental examples of Example 3 are shown in batch in FIG. 1.

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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)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

La présente invention concerne un caoutchouc au nitrile et son procédé de production. La présente invention permet d'obtenir : du caoutchouc au nitrile qui participe à une incroyable vitesse de polymérisation et une incroyable vitesse de vulcanisation et qui possède des caractéristiques avantageuses en termes d'aptitude au traitement pendant la vulcanisation. L'invention concerne également un procédé de production dudit caoutchouc.
PCT/KR2014/005543 2013-07-09 2014-06-24 Caoutchouc au nitrile et son procédé de production WO2015005597A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN201480001961.2A CN104507989B (zh) 2013-07-09 2014-06-24 腈橡胶及其制备方法
US14/421,205 US9809670B2 (en) 2013-07-09 2014-06-24 Nitrile rubber and method of preparing the same

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KR20130080277 2013-07-09
KR10-2013-0080277 2013-07-09
KR10-2014-0071217 2014-06-12
KR1020140071217A KR101606988B1 (ko) 2013-07-09 2014-06-12 니트릴 고무 및 이의 제조방법

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116003711A (zh) * 2021-10-21 2023-04-25 中国石油化工股份有限公司 丁腈橡胶及其制备方法、氢化丁腈橡胶、丁腈橡胶组合物和丁腈橡胶硫化胶

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20050053768A (ko) * 2002-10-17 2005-06-08 바이엘 인크. 저분자량 니트릴 고무를 포함하는 폴리머 복합체
KR20100022076A (ko) * 2007-05-22 2010-02-26 란세스 도이치란트 게엠베하 니트릴 고무
KR101098683B1 (ko) * 2006-12-22 2011-12-23 주식회사 엘지화학 중합전환율이 높은 아크릴로 니트릴-부타디엔-스티렌계공중합 라텍스 분말의 제조방법
KR20120061946A (ko) * 2009-08-31 2012-06-13 란세스 도이치란트 게엠베하 저분자량의 임의로 수소화된 니트릴 고무를 포함하는 가황성 중합체 조성물
WO2013000890A1 (fr) * 2011-06-27 2013-01-03 Versalis S.P.A. Procédé de préparation de caoutchoucs de nitrile

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20050053768A (ko) * 2002-10-17 2005-06-08 바이엘 인크. 저분자량 니트릴 고무를 포함하는 폴리머 복합체
KR101098683B1 (ko) * 2006-12-22 2011-12-23 주식회사 엘지화학 중합전환율이 높은 아크릴로 니트릴-부타디엔-스티렌계공중합 라텍스 분말의 제조방법
KR20100022076A (ko) * 2007-05-22 2010-02-26 란세스 도이치란트 게엠베하 니트릴 고무
KR20120061946A (ko) * 2009-08-31 2012-06-13 란세스 도이치란트 게엠베하 저분자량의 임의로 수소화된 니트릴 고무를 포함하는 가황성 중합체 조성물
WO2013000890A1 (fr) * 2011-06-27 2013-01-03 Versalis S.P.A. Procédé de préparation de caoutchoucs de nitrile

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116003711A (zh) * 2021-10-21 2023-04-25 中国石油化工股份有限公司 丁腈橡胶及其制备方法、氢化丁腈橡胶、丁腈橡胶组合物和丁腈橡胶硫化胶
CN116003711B (zh) * 2021-10-21 2023-06-20 中国石油化工股份有限公司 丁腈橡胶及其制备方法、氢化丁腈橡胶、丁腈橡胶组合物和丁腈橡胶硫化胶

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