JP2010523754A - スチレン−ブタジエンコポリマー、その製造方法および高凝集接着組成物 - Google Patents
スチレン−ブタジエンコポリマー、その製造方法および高凝集接着組成物 Download PDFInfo
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- JP2010523754A JP2010523754A JP2010501611A JP2010501611A JP2010523754A JP 2010523754 A JP2010523754 A JP 2010523754A JP 2010501611 A JP2010501611 A JP 2010501611A JP 2010501611 A JP2010501611 A JP 2010501611A JP 2010523754 A JP2010523754 A JP 2010523754A
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- JP
- Japan
- Prior art keywords
- styrene
- sbr
- butadiene copolymer
- range
- copolymer
- 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.)
- Granted
Links
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- 238000000034 method Methods 0.000 title claims abstract description 32
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- 244000043261 Hevea brasiliensis Species 0.000 description 3
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- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 3
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- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
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- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
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- QZLAEIZEPJAELS-UHFFFAOYSA-N 2,4,4-trimethylpentane-2-thiol Chemical compound CC(C)(C)CC(C)(C)S QZLAEIZEPJAELS-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- ZJCZFAAXZODMQT-UHFFFAOYSA-N 2-methylpentadecane-2-thiol Chemical compound CCCCCCCCCCCCCC(C)(C)S ZJCZFAAXZODMQT-UHFFFAOYSA-N 0.000 description 1
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
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- 239000004593 Epoxy Substances 0.000 description 1
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- 241000018646 Pinus brutia Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
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- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical class [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
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- 239000001110 calcium chloride Substances 0.000 description 1
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- 125000004432 carbon atom Chemical group C* 0.000 description 1
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- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 1
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- 229960000878 docusate sodium Drugs 0.000 description 1
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- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
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- 239000007769 metal material Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- ODHYIQOBTIWVRZ-UHFFFAOYSA-N n-propan-2-ylhydroxylamine Chemical compound CC(C)NO ODHYIQOBTIWVRZ-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
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- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
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- 239000004014 plasticizer Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
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- 230000001737 promoting effect Effects 0.000 description 1
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- 239000012429 reaction media Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- 239000001632 sodium acetate Substances 0.000 description 1
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- 230000002195 synergetic effect Effects 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- GEKDEMKPCKTKEC-UHFFFAOYSA-N tetradecane-1-thiol Chemical compound CCCCCCCCCCCCCCS GEKDEMKPCKTKEC-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- IPBROXKVGHZHJV-UHFFFAOYSA-N tridecane-1-thiol Chemical compound CCCCCCCCCCCCCS IPBROXKVGHZHJV-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
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Abstract
Description
(a)全活性固形分の10重量%〜45重量%のレベルでスチレンと、
(b)全活性固形分の40重量%〜90重量%のレベルでブタジエンと、
(c)全活性固形分の0重量%〜20重量%のレベルで、アクリロニトリル、メチルメタクリレート、酢酸ビニル、イソプレンもしくはアルキルラジカル中に3〜8個の炭素原子を有するアルキルアクリレート、または任意のアクリルモノマーから選択される、他のモノマーと、
(d)全活性固形分の5重量%〜55重量%のレベルで合成接着エンハンサー樹脂またはロジン誘導体;ならびに1つ以上の乳化剤および重合開始剤を含有する水溶液の接着エンハンサー(d)の存在下に重合するモノマー(a)、(b)および任意選択的に(c)と
を含有する混合物の形成を含む変性ポリマーの安定な接着剤分散系の製造方法を記載している。
本コポリマーの製造のための重合反応は、乳化重合で典型的に用いられる温度および圧力で、シングル-ステッププロセス(single-step process)で実施される。使用される乳化剤は、アルキルフェノール、脂肪酸またはアルコールのエチレンオキシド誘導体、ラウリル硫酸ナトリウム、アラルキルフェノール、脂肪酸または脂肪族アルコールの硫酸化またはスルホン化エチレンオキシドまたはプロピレンオキシド誘導体などの、表面張力を低下させる任意の化合物であってもよいが、しかしながら、必ずしも、ロジン石鹸である必要はない。重合の最終生成物は、ラベルおよび接着テープ向けの一般用途の感圧接着剤(PSA)を形成するために使用することができる。英国特許第2,137,212号明細書に述べられている実施例によれば、平均してスチレンの百分率は12.5%、ブタジエンの百分率は37.5%、およびロジンエステル誘導体の百分率は50%の範囲にある。しかしながら、前記文献は、エラストマーまたは最終接着剤の粘度調整も、履物および家具工業での用途も取り上げていない。
1 反応器をガス窒素でパージして、反応の開始および展開のプロセスを阻害するであろう酸素を媒体から完全に除去する工程と、
2 40℃〜60℃の範囲の温度に予熱された乳化剤を加える工程と、
3 モノマー(スチレンおよびブタジエン)と連鎖移動剤とを加える工程と、
4 予め調製されたフリーラジカル開始剤溶液を加える工程と、
5 ムーニー粘度が85〜150の範囲内に調整され、そして全固形分が20〜40%の範囲に維持される、SBRコポリマーラテックスが形成されるまで40℃〜65℃の範囲の温度で重合させる工程と、
6 モノマーの60%〜80%転化後に、反応停止剤を加えることによって重合を停止させる工程と、
7 未反応のブタジエンおよびスチレンモノマーを除去する工程と、
8 任意選択的に、無機塩および酸の水溶液などの、凝固剤を凝固容器に加えることによってラテックスを凝固させる工程と、
9 酸形態で組み込まれた、界面活性剤である樹脂石鹸を含有する、前記SBRコポリマーを洗浄しそして乾燥させる工程と
を含むことを特徴とする。
[I−SBRコポリマーの製造]
この実験では、SBRコポリマーを、本発明の乳化重合技法を用いて合成した。減圧の(約600mmHg)の、20リットル容量反応器中へ、6,150gの水、7%で水中に乳化された2,950gの樹脂石鹸、3,150gのスチレン、1,850gのブタジエンおよび5gのn−ドデシルメルカプタンを加えた。反応混合物を約50℃の温度に加熱し、攪拌下に保った。加えられるさらなる原料は、550gの4%過硫酸カリウムの水溶液を含んでいた。重合反応を、21〜22%のラテックスの全固形分が得られるまで50℃の一定温度に約10時間保ち、次に580gの4%n−イソプロピルヒドロキシルアミンの水溶液を加えた。55%の総スチレンおよびムーニー粘度120を示す、ラテックスのサンプルを、従来技法を用いて凝固させ、前記の通り乾燥させた。
固体エラストマーを得るために、上の工程Iで得られたSBRラテックスを凝固させた。
[接着組成物A−本発明の対象のSBR ]
この組成物は、ホット重合され、55%の総スチレン、ムーニー粘度120およびポリマー中に組み込まれた5%の樹脂酸を有する、実施例1で得られたSBRの使用を含んでいた。
この実施例は、20〜30%の範囲の総スチレン含有率および45〜55の範囲の典型的なムーニー粘度を有するコポリマーの使用を開示している英国特許出願公開第2173212A号明細書に記載されている実施例に基づいて、調合物を再製造した。
この組成物は、ホット重合され、55%の総スチレン、ムーニー粘度120およびポリマーに組み込まれた5%の樹脂酸を有する、実施例1で得られたSBRを使用した。
この実施例は、20〜30%の範囲の総スチレン含有率および45〜55の範囲の典型的なムーニー粘度を有するコポリマーの使用を開示している英国特許出願公開第2173212A号明細書に記載されている実施例に基づいているが、本出願人の発明によって好ましい特有の接着エンハンサーの存在下に接着調合物を再製造した。
Claims (15)
- 高いスチレン濃度および高いムーニー粘度のスチレン−ブタジエンコポリマー(SBR)であって、その酸形態でコポリマー中に組み込まれたままである樹脂石鹸乳化剤の存在下での、高温乳化重合の反応の生成物を含み、85〜150のムーニー粘度および45〜75%のスチレン含有率を有することを特徴とするスチレン−ブタジエンコポリマー(SBR)。
- 重合温度が40℃〜65℃であることを特徴とする請求項1に記載のスチレン−ブタジエンコポリマー(SBR)。
- 重合温度が好ましくは45℃〜60℃であることを特徴とする請求項2に記載のスチレン−ブタジエンコポリマー(SBR)。
- ムーニー粘度が好ましくは100〜130であることを特徴とする請求項1または2に記載のスチレン−ブタジエンコポリマー(SBR)。
- ラテックス相にあるとき、全固形分が20〜40%の範囲にあることを特徴とする請求項1〜4のいずれか一項に記載のスチレン−ブタジエンコポリマー(SBR)。
- 全固形分が好ましくは22〜30%であることを特徴とする請求項5に記載のスチレン−ブタジエンコポリマー(SBR)。
- 総スチレン含有率が好ましくは45〜65%であることを特徴とする請求項1、2または5に記載のスチレン−ブタジエンコポリマー(SBR)。
- 総スチレン含有率がより好ましくは50〜60%であることを特徴とする請求項7に記載のスチレン−ブタジエンコポリマー(SBR)。
- PVC、熱可塑性ゴム(TR)、皮革、再構成皮革、木材、発泡体、発泡ポリスチレン、ロックウール、ガラスウール、亜鉛めっき基材およびコンクリートから選択される基材の接合に適用されることを特徴とする請求項1〜8のいずれか一項に記載のスチレン−ブタジエンコポリマー(SBR)。
- 請求項1〜8のいずれか一項に記載のスチレン−ブタジエンコポリマー(SBR)の製造方法であって、それらを得る方法が、高温での水性乳化重合、界面活性剤として樹脂石鹸の使用、および高レベルでのムーニー粘度およびスチレン含有率の維持を同時に含むことを特徴とする方法。
- 以下の工程:
− 反応器をガス窒素でパージして、反応の開始および展開のプロセスを阻害するであろう酸素を媒体から完全に除去する工程と、
− 40℃〜60℃の範囲の温度に予熱された乳化剤を加える工程と、
− モノマー(スチレンおよびブタジエン)と連鎖移動剤とを加える工程と、
− 予め調製されたフリーラジカル開始剤溶液を加える工程と、
− ムーニー粘度が85〜150の範囲内に調整され、そして全固形分が20〜40%の範囲に維持される、SBRコポリマーラテックスが形成されるまで40℃〜65℃の範囲の温度で重合させる工程と、
− モノマーの60%〜80%転化後に、反応停止剤を加えることによって重合を停止させる工程と、
− 未反応のブタジエンおよびスチレンモノマーを除去する工程と、
− 任意選択的に、無機塩および酸の水溶液などの、凝固剤を凝固容器に加えることによってラテックスを凝固させる工程と、
− 酸形態で組み込まれた、界面活性剤である樹脂石鹸を含有する、前記SBRコポリマーを洗浄しそして乾燥させる工程と
を含むことを特徴とする請求項10に記載の方法。 - ムーニー粘度が好ましくは100〜130の範囲に調整され、そして全固形分が好ましくは22〜30%の範囲に維持されるSBRコポリマーラテックスが形成されるまで、好ましくは45℃〜60℃の範囲の温度で重合が起こることを特徴とする請求項10に記載の方法。
- 8〜20%の請求項1〜8のいずれか一項に記載のスチレン−ブタジエンコポリマーと、8〜24%の粘着付与剤と、0.5〜1.5%の保護剤と、54〜84%の溶剤とを含むことを特徴とする接着組成物。
- 好ましくは、12〜16%の前記スチレン−ブタジエンコポリマーを含むことを特徴とする請求項13に記載の接着組成物。
- PVC、熱可塑性ゴム(TR)、皮革、再構成皮革、木材、発泡体、発泡ポリスチレン、ロックウール、ガラスウール、亜鉛めっき基材およびコンクリートから選択される基材の接合に適用されることを特徴とする請求項13または14に記載の接着組成物。
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JPH0326732A (ja) * | 1989-06-26 | 1991-02-05 | Japan Synthetic Rubber Co Ltd | ゴム組成物 |
JPH0477593A (ja) * | 1990-07-13 | 1992-03-11 | Japan Synthetic Rubber Co Ltd | 缶シーリング材用共重合体ラテックス |
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EP0050226A1 (de) * | 1980-10-18 | 1982-04-28 | BASF Aktiengesellschaft | Verfahren zur Herstellung von wässrigen Dispersionen von Butadien-Co-polymerisaten durch Emulsionspolymerisation unter Zusatz von Harzen |
JPH0326732A (ja) * | 1989-06-26 | 1991-02-05 | Japan Synthetic Rubber Co Ltd | ゴム組成物 |
JPH0477593A (ja) * | 1990-07-13 | 1992-03-11 | Japan Synthetic Rubber Co Ltd | 缶シーリング材用共重合体ラテックス |
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US20100324203A1 (en) | 2010-12-23 |
KR20120120430A (ko) | 2012-11-01 |
ES2637767T3 (es) | 2017-10-17 |
JP5705536B2 (ja) | 2015-04-22 |
EP2134758B1 (en) | 2017-07-05 |
CN101715462B (zh) | 2015-08-05 |
BRPI0701521A2 (pt) | 2008-11-18 |
JP2015098605A (ja) | 2015-05-28 |
US8623972B2 (en) | 2014-01-07 |
WO2008122872A1 (en) | 2008-10-16 |
KR20100054764A (ko) | 2010-05-25 |
CN101715462A (zh) | 2010-05-26 |
US20120129975A1 (en) | 2012-05-24 |
EP2134758A1 (en) | 2009-12-23 |
KR101207717B1 (ko) | 2012-12-03 |
HUE036652T2 (hu) | 2018-07-30 |
PL2134758T3 (pl) | 2018-02-28 |
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