JP7469845B2 - 繊維用撥水剤組成物、撥水性繊維製品及び撥水性繊維製品の製造方法 - Google Patents
繊維用撥水剤組成物、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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- JP7469845B2 JP7469845B2 JP2018172938A JP2018172938A JP7469845B2 JP 7469845 B2 JP7469845 B2 JP 7469845B2 JP 2018172938 A JP2018172938 A JP 2018172938A JP 2018172938 A JP2018172938 A JP 2018172938A JP 7469845 B2 JP7469845 B2 JP 7469845B2
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- 239000004814 polyurethane Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- POSICDHOUBKJKP-UHFFFAOYSA-N prop-2-enoxybenzene Chemical compound C=CCOC1=CC=CC=C1 POSICDHOUBKJKP-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical class C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 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
- 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
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 238000001308 synthesis method Methods 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
- FBEIPJNQGITEBL-UHFFFAOYSA-J tetrachloroplatinum Chemical compound Cl[Pt](Cl)(Cl)Cl FBEIPJNQGITEBL-UHFFFAOYSA-J 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-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
- 238000012546 transfer Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- 125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 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
- ALVZGWPSQBCZLO-UHFFFAOYSA-L trimethyl(octadecyl)azanium;sulfate Chemical compound [O-]S([O-])(=O)=O.CCCCCCCCCCCCCCCCCC[N+](C)(C)C.CCCCCCCCCCCCCCCCCC[N+](C)(C)C ALVZGWPSQBCZLO-UHFFFAOYSA-L 0.000 description 1
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-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
- SUJUOAZFECLBOA-UHFFFAOYSA-N tritriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC SUJUOAZFECLBOA-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 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
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/02—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with hydrocarbons
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/10—Repellency against liquids
- D06M2200/12—Hydrophobic properties
-
- D—TEXTILES; PAPER
- D10—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
- D10B—INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES
- D10B2401/00—Physical properties
- D10B2401/02—Moisture-responsive characteristics
- D10B2401/021—Moisture-responsive characteristics hydrophobic
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Combustion & Propulsion (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
[式(I-1)中、dは1以上の整数を表し、eは2以上の整数を表し、(d+e)は3~6であり、R31は(d+e)価の有機基を表し、W1はエステル基、アミド基、ウレタン基又はウレア基である2価の基を表し、R32は炭素数8~24の直鎖又は分岐の1価の炭化水素基を表し、V1はヒドロキシ基、アミノ基又はカルボキシ基を表す。ただし、e個のV1のうちの2つ以上がヒドロキシ基及び/又はアミノ基である。]
[式(II-1)中、R33はf価の有機基を表し、fは2~7の整数を表す。]
[式(L-1)中、R220、R221及びR222はそれぞれ独立に、水素原子、メチル基、エチル基又は炭素数1~4のアルコキシ基を表し、R223は、芳香族環を有する炭素数8~40の炭化水素基、又は炭素数3~22のアルキル基を表し、R230、R231、R232、R233、R234及びR235はそれぞれ独立に、水素原子、メチル基、エチル基、炭素数1~4のアルコキシ基、芳香族環を有する炭素数8~40の炭化水素基、又は炭素数3~22のアルキル基を表し、a1は0以上の整数を表し、a2は1以上の整数を表し、(a1+a2)は10~200であり、a1が2以上の場合、複数存在するR220及びR221はそれぞれ同一であっても異なっていてもよく、a2が2以上の場合、複数存在するR222及びR223はそれぞれ同一であっても異なっていてもよい。]
[式(I-1)中、dは1以上の整数を表し、eは2以上の整数を表し、(d+e)は3~6であり、R31は(d+e)価の有機基を表し、W1はエステル基、アミド基、ウレタン基又はウレア基である2価の基を表し、R32は炭素数8~24の直鎖又は分岐の1価の炭化水素基を表し、V1はヒドロキシ基、アミノ基又はカルボキシ基を表す。ただし、e個のV1のうちの2つ以上がヒドロキシ基及び/又はアミノ基である。]
[式(II-1)中、R33はf価の有機基を表し、fは2~7の整数を表す。]
[式(L-1)中、R220、R221及びR222はそれぞれ独立に、水素原子、メチル基、エチル基又は炭素数1~4のアルコキシ基を表し、R223は、芳香族環を有する炭素数8~40の炭化水素基、又は炭素数3~22のアルキル基を表し、R230、R231、R232、R233、R234及びR235はそれぞれ独立に、水素原子、メチル基、エチル基、炭素数1~4のアルコキシ基、芳香族環を有する炭素数8~40の炭化水素基、又は炭素数3~22のアルキル基を表し、a1は0以上の整数を表し、a2は1以上の整数を表し、(a1+a2)は10~200であり、a1が2以上の場合、複数存在するR220及びR221はそれぞれ同一であっても異なっていてもよく、a2が2以上の場合、複数存在するR222及びR223はそれぞれ同一であっても異なっていてもよい。]
[式(b-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、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(b-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はヒドロキシ基、アミノ基、カルボキシ基、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。]
HLB=(親水基×20)/分子量 (H)
[式(I-2)中、gは0又は1の整数であり、hは2又は3の整数であり、iは1又は2の整数であり、(g+h+i)は4であり、R41は炭素数1~4の直鎖又は分岐の炭化水素基を表し、R42は炭素数1~2の2価のアルキレン基を表し、R43は炭素数1~4の2価のアルキレン基を表し、R44は炭素数8~24の直鎖又は分岐の1価の炭化水素基を表し、W2はエステル基、アミド基、ウレタン基又はウレア基である2価の基を表し、V2はヒドロキシ基、アミノ基又はカルボキシ基を表す。ただし、2つ以上のV2はヒドロキシ基及び/又はアミノ基である。]
[式(I-3)中、R51及びR52はそれぞれ独立に炭素数1~4の直鎖又は分岐の炭化水素基を表し、R54及びR55はそれぞれ独立に炭素数1~4の2価のアルキレン基を表し、R53、R56、R57及びR58はそれぞれ独立に下記一般式(4)又は下記一般式(5)で表される1価の基を示す。
-R59-V3 (4)
{R59は炭素数1~4の2価のアルキレン基を表し、V3はヒドロキシ基、アミノ基又はカルボキシ基を表す。}
-R60-W3-R61 (5)
{R60は炭素数1~4の2価のアルキレン基を表し、R61は炭素数8~24の直鎖又は分岐の1価の炭化水素基を表し、W3はエステル基、アミド基、ウレタン基又はウレア基である2価の基を表す。}、
ただし、R53、R56、R57及びR58のうち少なくとも2つは、V3がヒドロキシ基又はアミノ基である、上記一般式(4)で表される基である。]
[式(I-4)中、jは1~4の整数を表し、R71及びR73はそれぞれ独立に炭素数1~4の2価のアルキレン基を表し、R72及びR74はそれぞれ独立にヒドロキシ基、アミノ基又は下記一般式(6)で表される1価の基を表し、R75は水素、下記一般式(7)、下記一般式(8)又は下記一般式(9)で表される1価の基を表す。
-W4-R76 (6)
{式(6)中、W4はエステル基、アミド基、ウレタン基又はウレア基である2価の基を表し、R76は炭素数8~24の直鎖又は分岐の1価の炭化水素基を表す。}
-R77-OH (7)
{式(7)中、R77は炭素数2~3のアルキレン基を表す。}
-R78-W5-R79 (8)
{式(8)中、R78は炭素数2~3のアルキレン基を表し、R79は炭素数8~24の直鎖又は分岐の1価の炭化水素基を表し、W5はエステル基、アミド基、ウレタン基又はウレア基である2価の基を示す。}
-W6-R80 (9)
{式(9)中、W6はカルボニル基又はアミド基を表し、R80は炭素数8~24の直鎖又は分岐の1価の炭化水素基を表す。}、
ただし、R72、R74及びj個のR75のうち少なくとも2つはヒドロキシ基、アミノ基、水素、上記一般式(7)で表される1価の基であり、R72及びR74はヒドロキシ基又はアミノ基、R75は水素又は上記一般式(7)で表される1価の基である。]
[式(10)中、Bは、ブロック化剤に由来する基である。]
[式(L-2)中、R240は、炭素数2~6のアルキレン基を表し、R241は、単結合又は炭素数1~4のアルキレン基を表し、a3は0~3の整数を表す。a3が2又は3の場合、複数存在するR241は同一であっても異なっていてもよい。]
[式(L-3)中、R242は、炭素数2~6のアルキレン基を表し、R243は、単結合又は炭素数1~4のアルキレン基を表し、a4は0~3の整数を表す。a4が2又は3の場合、複数存在するR243は同一であっても異なっていてもよい。]
表1及び表2{表中、数値は(g)を示す}に示される材料を用いて、以下に示す手順により重合して、アクリル樹脂分散液を得た。
0.5Lオートクレーブにアクリル酸ステアリル15g、メタクリル酸ステアリル5g、Surfynol465(日信化学株式会社製、HLB=13)0.5g、Surfynol440(日信化学株式会社製、HLB=8)1g、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アンモニウム硫酸塩1g、トリプロピレングリコール15g及び水54.9g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0.15gを混合液に添加し、窒素雰囲気下でオートクレーブの内圧が0.3MPaを保つように塩化ビニル7gを継続的に圧入しながら、温度を61℃に保ち6時間反応させ、アクリル樹脂を27質量%含むアクリル樹脂分散液を得た。
表1及び表2に示される材料を用いたこと以外は、合成例1と同様にしてアクリル樹脂分散液を得た。
<ウレタン樹脂分散液の調整>
1000mlフラスコにジトリメチロールプロパン206.74g、ステアリン酸469.87g、p-トルエンスルホン酸3.4gを入れた。次いで、窒素雰囲気下で140℃まで昇温し、その後昇温速度約0.4℃/分、窒素気流下140~190℃で5時間脱水反応を行なった。窒素流量は、毎分5mlである。反応終了後、合成物の酸価を測定した。酸価は2.0mgKOH/gであった。
1000mlフラスコにトリメチロールプロパン255.88g、ステアリン酸542.51g、p-トルエンスルホン酸1.6gを入れた。次いで、窒素雰囲気下で140℃まで昇温し、その後昇温速度約0.4℃/分で窒素気流下140~190℃で5時間脱水反応を行なった。窒素流量は、毎分5mlである。反応終了後、合成物の酸価を測定した。酸価は2.0mgKOH/gであった。
(合成例16)
撹拌機、温度計、還流冷却機、窒素ガス導入管及び滴下ロートを備えた反応容器に、SiH基当量が63.2g/molであり、重合度が50であるメチルハイドロジェンシリコーン63.2gを入れ、窒素を流し、温度が65℃になるまで加熱しながら均一となるまで混合した。ヒドロシリル化触媒として、塩化白金(IV)のエチレングリコールモノブチルエーテル・トルエン混合溶液を、系内の反応物に対し白金濃度が5ppmとなるように添加した。反応物の温度が120℃となったところで、1モルの1-ドデセン168.3gを滴下し、120℃で6時間反応させた。付加反応完了の確認は、得られたオルガノ変性シリコーンのFT-IR分析を行い、メチルハイドロジェンシリコーンのSiH基由来の吸収スペクトルが消失したことを確認することで行った。こうして、上記一般式(L-1)におけるa1が0、a2が50、R222がメチル基、R223がドデシル基、R230、R231、R232、R233、R234及びR235がメチル基であるオルガノ変性シリコーンが得られた。さらに得られたオルガノ変性シリコーン20質量部に炭素数12~14の分岐高級アルコールのエチレンオキサイド9モル付加物3質量部を添加し、混合した。次いで、水77質量部を少量ずつ混合しながら添加し、水に乳化せしめて、オルガノ変性シリコーンを20質量%含むオルガノ変性シリコーン乳化物を得た。
1モルの1-ドデセン168.3gの代わりに、1モルの1-ヘキセン84.2gを用いたこと以外は合成例16と同様にしてオルガノ変性シリコーン及びオルガノ変性シリコーン乳化物を得た。なお、オルガノ変性シリコーンは、上記一般式(L-1)におけるa1が0、a2が50、R222がメチル基、R223がヘキシル基、R230、R231、R232、R233、R234及びR235がメチル基であるオルガノ変性シリコーンが得られた。
1モルの1-ドデセン168.3gの代わりに、1モルの1-オクタデセン252.5gを用いたこと以外は合成例16と同様にしてオルガノ変性シリコーン及びオルガノ変性シリコーン乳化物を得た。なお、オルガノ変性シリコーンは、上記一般式(L-1)のa1が0、a2が50、R222がメチル基、R223がオクタデシル基、R230、R231、R232、R233、R234及びR235がメチル基であるオルガノ変性シリコーンが得られた。
1モルの1-ドデセン168.3gの代わりに、0.5モルの1-ドデセン84.2g、及び、0.5モルの1-オクタデセン126.2gを用いたこと以外は合成例16と同様にしてオルガノ変性シリコーン及びオルガノ変性シリコーン乳化物を得た。なお、オルガノ変性シリコーンは、上記一般式(L-1)のa1が0、a2が50、R222がメチル基、R223がドデシル基又はオクタデシル基、R230、R231、R232、R233、R234及びR235がメチル基であるオルガノ変性シリコーンが得られた。
メチルハイドロジェンシリコーン63.2gの代わりに、ジメチルシロキサンとメチルハイドロジェンシロキサンとの共重合体140.5gを用いたこと、及び、1モルの1-ドデセン168.3gの代わりに、1モルの1-オクタデセン252.5gを用いたこと以外は合成例17と同様にしてオルガノ変性シリコーン及びオルガノ変性シリコーン乳化物を得た。ジメチルシロキサンとメチルハイドロジェンシロキサンとの共重合体のSiH基当量は140.5g/mol、重合度は50であった。なお、オルガノ変性シリコーンは、上記一般式(L-1)のa1が25、a2が25、R220及びR221がメチル基、R222がメチル基、R223がオクタデシル基、R230、R231、R232、R233、R234及びR235がメチル基であるオルガノ変性シリコーンが得られた。
(製造例1)
高圧反応容器にパラフィンワックス{融点69℃、針入度12(25℃)}150g、純水350g、ポリオキシエチレンステアリルエーテル(HLB=10.7)8.5g、ポリオキシアルキレン分岐デシルエーテル(HLB=14.7)6.5gを入れて密封した。次いで、容器内を攪拌しながら110~120℃まで昇温した。その後、容器内を高圧に保ちながら30分間高圧乳化し、パラフィンワックスの水性分散体を得た。更に純水でワックス分を30質量%に調整し、ワックス乳化物を得た。
パラフィンワックス{融点69℃、針入度12(25℃)}150gに代えて、パラフィンワックス{融点77℃、針入度4(25℃)}150gを用いたこと以外は、製造例1と同様にしてパラフィンワックスの水性分散体及びワックス乳化物を得た。
パラフィンワックス{融点69℃、針入度12(25℃)}に代えて、パラフィンワックス{融点 50℃、針入度22(25℃)}150gを用いたこと以外は、製造例1と同様にしてパラフィンワックスの水性分散体及びワックス乳化物を得た。
(実施例1)
合成例1で得たアクリル樹脂分散液、合成例18で得たオルガノ変性シリコーン乳化物、製造例2で得たワックス乳化物、媒体としてブチルジグリコール及び帯電防止剤としてナイスポールFE-26(日華化学(株)社製)を、表3に示される組成(質量部)となるように混合し、試験液を得た。なお、実施例1の試験液におけるアクリル樹脂、オルガノ変性シリコーン及びワックスの配合量はそれぞれ、20質量部×27質量%=5.4質量部、10質量部×20質量%=2質量部、及び10質量部×30質量%=3質量部で算出される。
・IE-7045(商品名、東レダウ・コーニング(株)製、ジメチルシリコーン)
・ナイスポールFE-26(商品名、日華化学(株)製)
表3~表6に示される材料を用いたこと以外は、実施例1と同様にして試験液を得た。
JIS L 1092(2009)のスプレー法と同様の方法でシャワー水温を20℃として試験をした。本試験においては、実施例、参考例及び比較例の組成で調製した試験液を、アクリル樹脂、その他アクリル樹脂、ウレタン樹脂、オルガノ変性シリコーン、ジメチルシリコーン、ワックス及びその他ワックスの総含有量が1質量%となるように水で希釈し、処理液を得た。次いで、染色を行ったポリエステル100%布又はナイロン100%布を得られた処理液に浸漬処理(ピックアップ率60質量%)した。次いで、浸漬処理を行った布を130℃で2分間乾燥し、更に170℃で1分間熱処理して、撥水性繊維製品を得た。撥水性繊維製品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。評価結果を表3~表6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
実施例、参考例及び比較例の組成で調製した試験液に、架橋剤としてNKアシスト NY-30(日華化学(株)製)を3g/Lとなるように加えた。次いで、アクリル樹脂、その他アクリル樹脂、ウレタン樹脂、オルガノ変性シリコーン、ジメチルシリコーン、ワックス、その他ワックス及び架橋剤の総含有量が1質量%となるように試験液を水で希釈し、処理液を調整した。染色を行ったポリエステル100%布又はナイロン100%布に対して処理液を用いて浸漬処理(ピックアップ率60質量%)した。次いで、浸漬処理をした布を130℃で2分間乾燥し、更に170℃で1分間熱処理して、撥水性繊維製品を得た。得られた撥水性繊維製品を、JIS L 0217(1995)の103法による洗濯を10回(L-10)行い、風乾後の撥水性を前述の撥水性評価方法と同様に評価した。評価結果を表3~表6に示す。
II.撥水性繊維製品の耐久撥水性評価と同様にして撥水性繊維製品を得た。得られた撥水性繊維製品にイオン交換水20μlを滴下し、形成される水滴の接触角を測定した。接触角の測定にはKRUSS製自動接触角計 DSA25を用いた。評価結果を表3~表6に示す。
II.撥水性繊維製品の耐久撥水性評価と同様にして撥水性繊維製品を得た。得られた撥水性繊維製品を、水平で平坦な場所に置き、200μlの水滴を3滴ずつ撥水性繊維製品上に滴下し室温にて放置した。10分、30分、60分、120分後に撥水性繊維製品上に接触角が90°以上の水滴状態で残っている液滴数を評価結果とした。評価結果を表3~表6に示す。
IIに記載のポリエステル100%の撥水性繊維製品について、ハンドリングにて下記に示す5段階で評価した。評価基準は、比較例1における撥水性繊維製品の風合いが2、比較例2における撥水性繊維製品の風合いが5となるように定めた。評価結果を表3~表6に示す。
1:硬い ~ 5:柔らかい
JIS K 6404-5(1999)に準拠して試験を行った。まず、実施例、参考例及び比較例の組成で調製した試験液に、架橋剤としてNKアシスト NY-30(日華化学(株)製)を3g/Lとなるように加えた。次いで、アクリル樹脂、その他アクリル樹脂、ウレタン樹脂、オルガノ変性シリコーン、ジメチルシリコーン、ワックス、その他ワックス及び架橋剤の総含有量が3質量%となるように試験液を水で希釈し、処理液を調整した。次いで、染色を行ったナイロン100%布に対して得られた処理液を用いて浸漬処理(ピックアップ率60質量%)した。次いで浸漬処理をした布を130℃で2分間乾燥し、更に160℃で30秒熱処理し、基布を得た。その得られた基布に、熱圧着装置を用いて、シームテープ(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~表6に示す。
Claims (4)
- 繊維用撥水剤組成物であって、
(α)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有するアクリル樹脂及び/又は下記一般式(I-1)で表される多官能化合物由来の構造単位と下記一般式(II-1)で表されるイソシアネート化合物由来の構造単位とを有するウレタン樹脂と、
(β)下記一般式(L-1)で表されるオルガノ変性シリコーンと、
(γ)ワックスと、
架橋剤と、
を含有し、
前記(α)成分が、前記アクリル樹脂を含み、
前記撥水剤組成物における、前記(α)成分の総質量と前記(β)成分の総質量との比((α):(β))は、95:5~50:50であり、
前記撥水剤組成物における、前記(α)成分の総質量と前記(γ)成分の総質量との比((α):(γ))は、90:10~40:60である、繊維用撥水剤組成物。
R31[-W1-R32]d[-V1]e (I-1)
[式(I-1)中、dは1以上の整数を表し、eは2以上の整数を表し、(d+e)は3~6であり、R31は(d+e)価の有機基を表し、W1はエステル基、アミド基、ウレタン基又はウレア基である2価の基を表し、R32は炭素数8~24の直鎖又は分岐の1価の炭化水素基を表し、V1はヒドロキシ基、アミノ基又はカルボキシ基を表す。ただし、e個のV1のうちの2つ以上がヒドロキシ基及び/又はアミノ基である。]
R33[-NCO]f (II-1)
[式(II-1)中、R33はf価の有機基を表し、fは2~7の整数を表す。]
- 前記アクリル樹脂が、塩化ビニル及び塩化ビニリデンのうち少なくとも1種の単量体(E)に由来する構成単位を更に有する、請求項1に記載の繊維用撥水剤組成物。
- 繊維基材と、前記繊維基材に付着した請求項1又は2に記載の繊維用撥水剤組成物と、を備える、撥水性繊維製品。
- 繊維基材に、請求項1又は2に記載の繊維用撥水剤組成物が含まれる処理液を接触させる工程を備える、撥水性繊維製品の製造方法。
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JP2017222827A (ja) | 2016-06-17 | 2017-12-21 | 日華化学株式会社 | 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 |
WO2018054712A1 (en) | 2016-09-23 | 2018-03-29 | Huntsman Textile Effects (Germany) Gmbh | Fluorine-free aqueous dispersions for the finishing of textile fabrics |
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