JP2018119250A - 撥水剤組成物、撥水性繊維製品及び撥水性繊維製品の製造方法 - Google Patents
撥水剤組成物、撥水性繊維製品及び撥水性繊維製品の製造方法 Download PDFInfo
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- JP2018119250A JP2018119250A JP2017013521A JP2017013521A JP2018119250A JP 2018119250 A JP2018119250 A JP 2018119250A JP 2017013521 A JP2017013521 A JP 2017013521A JP 2017013521 A JP2017013521 A JP 2017013521A JP 2018119250 A JP2018119250 A JP 2018119250A
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- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
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- 239000010452 phosphate Substances 0.000 description 1
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- 125000003367 polycyclic group Chemical group 0.000 description 1
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- 229920001223 polyethylene glycol Chemical group 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
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- 239000004814 polyurethane Substances 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 238000011160 research Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
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- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 125000005628 tolylene group Chemical group 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- AMJYHMCHKZQLAY-UHFFFAOYSA-N tris(2-isocyanatophenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound O=C=NC1=CC=CC=C1OP(=S)(OC=1C(=CC=CC=1)N=C=O)OC1=CC=CC=C1N=C=O AMJYHMCHKZQLAY-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical group NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000012178 vegetable wax Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Landscapes
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
Abstract
Description
[式(I−1)中、R3は水素又はメチル基を表し、Xは炭素数1〜6の直鎖もしくは分岐のアルキレン基を表し、Y1は炭素数2〜4のアルキレンオキシ基を含む2価の基を表す。]
[式(II−1)中、R4は重合性不飽和基を有する炭素数13〜17の1価の不飽和炭化水素基を表し、Y2は炭素数2〜4のアルキレンオキシ基を含む2価の基を表す。]
[式(I−1)中、R3は水素又はメチル基を表し、Xは炭素数1〜6の直鎖もしくは分岐のアルキレン基を表し、Y1は炭素数2〜4のアルキレンオキシ基を含む2価の基を表す。]
[式(II−1)中、R4は重合性不飽和基を有する炭素数13〜17の1価の不飽和炭化水素基を表し、Y2は炭素数2〜4のアルキレンオキシ基を含む2価の基を表す。]
非フッ素系ポリマー(α)は、塩化ビニル及び塩化ビニリデンのうち少なくともいずれか1種の単量体(VC)(以下、「(VC)成分」ともいう。)に由来する構成単位を含有する非フッ素系ポリマーであって、該非フッ素系ポリマーを構成する単量体成分の全量を基準として単量体(VC)の含有割合が50質量%以上である。
非フッ素系ポリマー(β)は、上記一般式(A−1)で表される(メタ)アクリル酸エステル単量体(A)に由来する構成単位を含有する非フッ素系ポリマーであって、該非フッ素系ポリマーを構成する単量体成分の全量を基準として(メタ)アクリル酸エステル単量体(A)の含有割合が50質量%以上である。
本実施形態の非フッ素系ポリマー(α)又は(β)、特には、非フッ素系ポリマー(α)は、得られる繊維製品の撥水性、及び本実施形態の非フッ素系ポリマー(α)又は(β)、特には非フッ素系ポリマー(α)の乳化重合又は分散重合時及び重合後の組成物中での乳化安定性を向上できる点で、(VC)成分若しくは(A)成分、又は(VC)成分及び(A)成分に加えて、(B1)HLBが7〜18である下記一般式(I−1)で表される化合物、(B2)HLBが7〜18である下記一般式(II−1)で表される化合物、及び(B3)HLBが7〜18である、ヒドロキシル基及び重合性不飽和基を有する油脂に炭素数2〜4のアルキレンオキサイドを付加した化合物のうちから選ばれる少なくとも1種の反応性乳化剤(B)(以下、「(B)成分」ともいう)を単量体成分として含有していることが好ましい。
[式(I−2)中、R3は水素又はメチル基を表し、Xは炭素数1〜6の直鎖もしくは分岐のアルキレン基を表し、A1Oは炭素数2〜4のアルキレンオキシ基を表し、mは上記HLBの範囲内になるように適宜選択することができ、具体的には、1〜80の整数が好ましく、mが2以上のときm個のA1Oは同一であっても異なっていてもよい。]
[式(II−2)中、R4は重合性不飽和基を有する炭素数13〜17の1価の不飽和炭化水素基を表し、A2Oは炭素数2〜4のアルキレンオキシ基を表し、nは上記HLBの範囲内になるように適宜選択することができ、具体的には、1〜50の整数が好ましく、nが2以上のときn個のA2Oは同一であっても異なっていてもよい。]
[式(C−1)中、R5は水素又はメチル基を表し、R6はヒドロキシル基、アミノ基、カルボキシル基、エポキシ基、イソシアネート基及び(メタ)アクリロイルオキシ基からなる群より選ばれる少なくとも1種の官能基を有する炭素数1〜11の1価の鎖状炭化水素基を表す。ただし、分子内における(メタ)アクリロイルオキシ基の数は2以下である。]
[式(C−4)中、R10は水素又はメチル基を表し、pは2以上の整数を表し、Sは(p+1)価の有機基を表し、Tは重合性不飽和基を有する1価の有機基を表す。]
シリコーン樹脂としては、シリコーンレジン、シリコーンオイルを挙げることができる。シリコーンレジンとは、構成成分としてMQ、MDQ、MT、MTQ、MDT又はMDTQを含み、25℃にて固形状であり、三次元構造を有するオルガノポリシロキサンである。ここで、M、D、T及びQは、それぞれ(R’’)3SiO0.5単位、(R’’)2SiO単位、R’’SiO1.5単位及びSiO2単位を表す。R’’は、炭素数1〜10の1価の脂肪族炭化水素基、又は、炭素数6〜15の1価の芳香族炭化水素基を表す。
[式中、R21及びR22はそれぞれ独立に、炭素数1〜8の直鎖若しくは分岐鎖を有するアルキル基又は炭素数2〜8の直鎖若しくは分岐鎖を有するアルケニル基を表す。]
[式中、R23は、炭素数1〜8の直鎖若しくは分岐鎖を有するアルキル基又は炭素数2〜8の直鎖若しくは分岐鎖を有するアルケニル基を表す。]
HLB=(親水基×20)/分子量
表1及び2に示される組成(表中、数値は(g)を示す)を有する混合液を、以下に示す手順により重合して、ポリマー分散液を得た。
オートクレーブに、アクリル酸イソボルニル2g、ノイゲンXL−100(第一工業製薬株式会社製、ポリオキシアルキレン分岐デシルエーテル、HLB=14.7)0.2g、ノイゲンXL−60(第一工業製薬株式会社製、ポリオキシアルキレン分岐デシルエーテル、HLB=12.5)1.3g、ノイゲンXL−40(第一工業製薬株式会社製、ポリオキシアルキレン分岐デシルエーテル、HLB=10.5)0.5g,ステアリルトリメチルンモニウム硫酸塩1g、トリプロピレングリコール25g及び水144.7gを入れ、45℃にて混合攪拌し混合液とした。この混合液に超音波を照射して全単量体を乳化分散させた。次いで、アゾビス(イソブチルアミジン)二塩酸塩0.3gを混合液に添加し、窒素雰囲気下で、塩化ビニル25gをオートクレーブの内圧が0.3MPaを保つよう継続的に圧入しながら、60℃にて6時間ラジカル重合させて、非フッ素系ポリマー(α)を13.5質量%含む非フッ素系ポリマー(α)分散液を得た。
表1に記載の材料を用いた以外は、実施例1と同様に重合を行い、非フッ素系ポリマー(α)を13.5質量%含む非フッ素系ポリマー分散液をそれぞれ得た。
表2に記載の材料を用いた以外は、実施例1と同様に重合を行い、非フッ素系ポリマー(β)を26.7質量%含む非フッ素系ポリマー分散液をそれぞれ得た。
ノイゲンXL−100(14.7)(第一工業製薬株式会社製、ポリオキシアルキレン分岐デシルエーテル、HLB=14.7)
ノイゲンXL−60(12.5)(第一工業製薬株式会社製、ポリオキシアルキレン分岐デシルエーテル、HLB=12.5)
ノイゲンXL−40(10.5)(第一工業製薬株式会社製、ポリオキシアルキレン分岐デシルエーテル、HLB=10.5)
(調製例1)
シリコーン樹脂としてTSF−4709(アミノ変性シリコーンオイル、モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社製、商品名)20質量部と、グリコール酸0.3質量部と、炭素数12〜14の分岐アルコールのエチレンオキサイド5モル付加物4質量部と、ブチルジグリコール5質量部を混合した。次いで、得られた混合物に、水70.7質量部を少量ずつ混合しながら添加し、シリコーン樹脂を20質量%含む分散液を得た。
シリコーン樹脂として下記の樹脂を用いたこと以外は調製例1と同様にして、シリコーン樹脂を20質量%含むシリコーン樹脂分散液を得た。
(調製例2)BY 16−872(アミノシリコーン、東レ・ダウコーニング(株)製、商品名)
(調製例3)KF−9901(メチルハイドロジェンシリコーン、信越化学工業(株)製、商品名)
(調製例4)KF−96−3000cs(ジメチルシリコーン、信越化学工業(株)製、商品名)
(調製例5)SF 8416(アルキルシリコーン、東レ・ダウコーニング(株)製、商品名)
KF8005(アミノ変性シリコーン、信越化学工業(株)製、商品名)18.5質量部と、蟻酸0.15質量部と、炭素数12〜14の分岐アルコールのエチレンオキサイド5モル付加物0.5質量部とを混合した。次いで、得られた混合物に、水80.85質量部を少量ずつ混合しながら添加し、アミノ変性シリコーンを18.5質量%含む分散液を得た。
親水化剤と疎水化剤とにより改質されたシリカ(シリカ表面に親水性基と疎水性基とを有するシリカ)としてレオロシールHG−09(アミノ基とトリメチルシリル基を有するシリカ、(株)トクヤマ製)10質量部、酸成分として90%酢酸1質量部、及び水89質量部を混合した。次いで、超音波乳化機US−600E(株式会社日本精機製作所)を使用して60℃を維持しながら10分間分散した。その後冷却し、レオロシールHG−09を10質量%含む分散液を得た。
(実施例1〜29及び比較例1〜4)
表3〜7に示される比率(表中、数値は(質量部)を示す)で、非フッ素系ポリマー(α)分散液、非フッ素系ポリマー(β)分散液、シリコーン樹脂分散液を混合し、撥水剤組成物をそれぞれ得た。
上記で得られた撥水剤組成物について、下記の評価を行った。
JIS L 1092(2009)のスプレー法に準じてシャワー水温を20℃として試験をした。本試験においては、染色を行ったポリエステル100%布又はナイロン100%布を、実施例及び比較例の撥水剤組成物を非フッ素系ポリマー(α)、非フッ素系ポリマー(β)及びシリコーン樹脂の合計の含有量が3質量%となるように水で希釈した処理液に浸漬処理(ピックアップ率60質量%)した後、130℃で2分間乾燥し、更に170℃で30秒の条件で熱処理して、得られた布の撥水性を評価した。結果は目視にて下記の等級で評価した。なお、特性がわずかに良好な場合は等級に「+」をつけ、特性がわずかに劣る場合は等級に「−」をつけた。結果を表3〜7に示す。
撥水性:状態
5:表面に付着湿潤のないもの
4:表面にわずかに付着湿潤を示すもの
3:表面に部分的湿潤を示すもの
2:表面に湿潤を示すもの
1:表面全体に湿潤を示すもの
0:表裏両面が完全に湿潤を示すもの
風合は、染色を行ったポリエステル100%布を、実施例及び比較例の撥水剤組成物を非フッ素系ポリマー(α)、非フッ素系ポリマー(β)及びシリコーン樹脂の合計の含有量が3質量%となるように水で希釈した処理液に浸漬処理(ピックアップ率60質量%)した後、130℃で2分間乾燥し、更に170℃で30秒間熱処理したものを用いて評価した。結果はハンドリングにて下記に示す5段階で評価した。結果を表3〜7に示す。
1:硬い 〜 5:柔らかい
JIS L 1092(2009)のスプレー法に準じてシャワー水温を20℃として試験をした。本試験においては、染色を行ったポリエステル100%布を、非フッ素系ポリマー(α)、非フッ素系ポリマー(β)及びシリコーン樹脂の合計の含有量が3質量%、ブロックドイソシアネート系架橋剤としてNKアシストNY−50が1質量%、浸透剤としてテキスポートBG−290が1質量%、帯電防止剤としてナイスポールFE−26が0.5質量%となるように、実施例及び比較例の撥水剤組成物及び上記各薬剤を水で希釈した処理液に浸漬処理(ピックアップ率60質量%)した後、130℃で2分間乾燥し、更に170℃で60秒間熱処理して得られた布(L−0)、及びJIS L 0217(1995)の103法による洗濯を10回(L−10)行った後の布の撥水性を上記撥水性評価方法と同様に評価した。また、ナイロン100%布の場合も、熱処理温度を170℃から160℃に変えたこと以外は、ポリエステル100%布の場合と同様に評価した。結果を表3〜7に示す。
JIS K 6404−5(1999)に準拠して試験を行った。本試験においては、染色を行ったナイロン100%布を、実施例及び比較例の撥水剤組成物を非フッ素系ポリマー(α)、非フッ素系ポリマー(β)及びシリコーン樹脂の合計の含有量が3質量%となるように水で希釈した処理液に、浸漬処理(ピックアップ率60質量%)した後、130℃で2分間乾燥し、更に170℃で30秒熱処理して得られたものを基布とした。その得られた基布に、熱圧着装置を用いて、ホットメルト接着テープ(サン化成株式会社製「MELCOテープ」)を150℃で1分間熱接着させ、基布とシームテープとの層間の剥離強度をオートグラフ(AG−IS、島津製作所(株)製)にて測定した。掴み具の移動速度を100mm/minで引っ張り、応力の平均値を剥離強度[N/inch]とした。結果を表3〜7に示す。
Claims (8)
- 塩化ビニル及び塩化ビニリデンのうち少なくともいずれか1種の単量体(VC)に由来する構成単位を含有する非フッ素系ポリマーであって、該非フッ素系ポリマーを構成する単量体成分の全量を基準として前記単量体(VC)の含有割合が50質量%以上である非フッ素系ポリマー(α)と、
下記一般式(A−1)で表される(メタ)アクリル酸エステル単量体(A)に由来する構成単位を含有する非フッ素系ポリマーであって、該非フッ素系ポリマーを構成する単量体成分の全量を基準として前記(メタ)アクリル酸エステル単量体(A)の含有割合が50質量%以上である非フッ素系ポリマー(β)、及び/又は、シリコーン樹脂(γ)と、
を含む、撥水剤組成物。
[式(A−1)中、R1は水素又はメチル基を表し、R2は置換基を有していてもよい炭素数12〜30の1価の炭化水素基を表す。] - 前記非フッ素系ポリマー(α)が、(B1)HLBが7〜18である下記一般式(I−1)で表される化合物、(B2)HLBが7〜18である下記一般式(II−1)で表される化合物、及び(B3)HLBが7〜18である、ヒドロキシル基及び重合性不飽和基を有する油脂に炭素数2〜4のアルキレンオキサイドを付加した化合物からなる群より選択される少なくとも1種の反応性乳化剤(B)に由来する構成単位を更に含有する、請求項1に記載の撥水剤組成物。
[式(I−1)中、R3は水素又はメチル基を表し、Xは炭素数1〜6の直鎖もしくは分岐のアルキレン基を表し、Y1は炭素数2〜4のアルキレンオキシ基を含む2価の基を表す。]
[式(II−1)中、R4は重合性不飽和基を有する炭素数13〜17の1価の不飽和炭化水素基を表し、Y2は炭素数2〜4のアルキレンオキシ基を含む2価の基を表す。] - 前記撥水剤組成物が前記非フッ素系ポリマー(β)を含み、
前記非フッ素系ポリマー(β)が、(B1)HLBが7〜18である下記一般式(I−1)で表される化合物、(B2)HLBが7〜18である下記一般式(II−1)で表される化合物、及び(B3)HLBが7〜18である、ヒドロキシル基及び重合性不飽和基を有する油脂に炭素数2〜4のアルキレンオキサイドを付加した化合物からなる群より選択される少なくとも1種の反応性乳化剤(B)に由来する構成単位を更に含有する、請求項1又は2に記載の撥水剤組成物。
[式(I−1)中、R3は水素又はメチル基を表し、Xは炭素数1〜6の直鎖もしくは分岐のアルキレン基を表し、Y1は炭素数2〜4のアルキレンオキシ基を含む2価の基を表す。]
[式(II−1)中、R4は重合性不飽和基を有する炭素数13〜17の1価の不飽和炭化水素基を表し、Y2は炭素数2〜4のアルキレンオキシ基を含む2価の基を表す。] - 前記非フッ素系ポリマー(α)が、前記一般式(A−1)で表される(メタ)アクリル酸エステル単量体(A)に由来する構成単位を更に含有し、
前記非フッ素系ポリマー(α)における前記(メタ)アクリル酸エステル単量体(A)がアクリル酸エステル単量体(a1)とメタクリル酸エステル単量体(a2)とを含み、前記(メタ)アクリル酸エステル単量体(A)に含まれる前記アクリル酸エステル単量体(a1)の質量と前記メタクリル酸エステル単量体(a2)の質量との比(a1)/(a2)が30/70〜90/10である、請求項1〜3のいずれか一項に記載の撥水剤組成物。 - 前記撥水剤組成物が前記非フッ素系ポリマー(β)を含み、
前記非フッ素系ポリマー(β)における前記(メタ)アクリル酸エステル単量体(A)がアクリル酸エステル単量体(a1)とメタクリル酸エステル単量体(a2)とを含み、前記(メタ)アクリル酸エステル単量体(A)に含まれる前記アクリル酸エステル単量体(a1)の質量と前記メタクリル酸エステル単量体(a2)の質量との比(a1)/(a2)が30/70〜90/10である、請求項1〜4のいずれか一項に記載の撥水剤組成物。 - 前記撥水剤組成物が前記シリコーン樹脂(γ)を含み、
前記シリコーン樹脂(γ)が、アミノ変性シリコーン、シリコーンレジン、ジメチルシリコーン、メチルハイドロジェンシリコーン、及びアルキル変性シリコーンからなる群より選択される少なくとも1種である、請求項1〜5のいずれか一項に記載の撥水剤組成物。 - 請求項1〜6のいずれか一項に記載の撥水剤組成物における、前記非フッ素系ポリマー(α)と、前記非フッ素系ポリマー(β)及び/又は前記シリコーン樹脂(γ)とが付着した繊維製品からなる、撥水性繊維製品。
- 繊維製品を、請求項1〜6のいずれか一項に記載の撥水剤組成物が含まれる処理液で処理する工程、を備える、撥水性繊維製品の製造方法。
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