JPWO2018143155A1 - 紙用添加剤及びその製造方法、並びに紙用添加剤を含有する紙 - Google Patents
紙用添加剤及びその製造方法、並びに紙用添加剤を含有する紙 Download PDFInfo
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- JPWO2018143155A1 JPWO2018143155A1 JP2018565541A JP2018565541A JPWO2018143155A1 JP WO2018143155 A1 JPWO2018143155 A1 JP WO2018143155A1 JP 2018565541 A JP2018565541 A JP 2018565541A JP 2018565541 A JP2018565541 A JP 2018565541A JP WO2018143155 A1 JPWO2018143155 A1 JP WO2018143155A1
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- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
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- AQGNVWRYTKPRMR-UHFFFAOYSA-N n'-[2-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCNCCN AQGNVWRYTKPRMR-UHFFFAOYSA-N 0.000 description 1
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- RQFLGKYCYMMRMC-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O RQFLGKYCYMMRMC-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
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- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 230000005476 size effect Effects 0.000 description 1
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- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- JMHCCAYJTTWMCX-QWPJCUCISA-M sodium;(2s)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate;pentahydrate Chemical compound O.O.O.O.O.[Na+].IC1=CC(C[C@H](N)C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 JMHCCAYJTTWMCX-QWPJCUCISA-M 0.000 description 1
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- 239000002023 wood Substances 0.000 description 1
- DTOSIQBPPRVQHS-UHFFFAOYSA-N α-Linolenic acid Chemical compound CCC=CCC=CCC=CCCCCCCCC(O)=O DTOSIQBPPRVQHS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/48—Polymers modified by chemical after-treatment
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/54—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen
- D21H17/56—Polyamines; Polyimines; Polyester-imides
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
Abstract
Description
(1)1分子内に3個以上のアミノ基を有するポリアルキレンポリアミン(a)、炭素数8〜22の1価脂肪酸(b)、多価カルボン酸類(c)、尿素類(d)及びアルキル化剤(e)を反応させて得られる化合物(A)を含有することを特徴とする紙用添加剤、
(2)化合物(A)がカルボキシル基又はその塩を有することを特徴とする前記(1)に記載の紙用添加剤、
(3)尿素類(d)が尿素であり、かつ、アルキル化剤(e)がエピハロヒドリン類であることを特徴とする前記(1)に記載の紙用添加剤。
(4)化合物(A)が、(a)のアミノ基1当量に対して、(b)のカルボニル基が0.35〜0.65当量、(c)のカルボニル基が0.01〜0.20当量、(d)が0.01〜0.35当量、(e)が0.01〜0.40当量の割合で反応させて得られる化合物であることを特徴とする前記(1)〜(3)のいずれか一項に記載の紙用添加剤。
(5)前記(1)〜(4)のいずれか一項に記載の紙用添加剤を含有することを特徴とする紙。
(6)1分子内に3個以上のアミノ基を有するポリアルキレンポリアミン(a)、炭素数8〜22の1価脂肪酸(b)、多価カルボン酸類(c)、尿素類(d)及びアルキル化剤(e)を反応させて得られる化合物(A)を含有することを特徴とする紙用添加剤の製造方法。
(7)(a)のアミノ基1当量に対して、(b)のカルボニル基が0.35〜0.65当量、(c)のカルボニル基が0.01〜0.20当量、(d)が0.01〜0.35当量、(e)が0.01〜0.40当量の割合で反応させて得られる化合物(A)であることを特徴とする前記(6)に記載の紙用添加剤の製造方法。
温度計、冷却管、撹拌機を有するセパラブルフラスコに、ポリアルキレンポリアミン(a)としてジエチレントリアミン1mol、1価脂肪酸(b)としてステアリン酸さくら(日油株式会社製、ステアリン酸/パルミチン酸混合物)1.8mol((a)のアミノ基1当量に対する(b)のカルボニル基が0.60当量)を添加し、170℃まで昇温し、生成する水を除去しながら、170℃で4時間反応させた。次いで、尿素類(d)として尿素0.3mol((a)のアミノ基に対する(d)が0.10当量)を添加し、生成するアンモニアを除去しながら130℃で90分反応させ、多価カルボン酸類(c)として無水マレイン酸0.14mol((a)のアミノ基1当量に対する(c)のカルボニル基が0.09当量)を添加し130℃で30分反応させて化合物(A−1)を得た。その後、塩基として25質量%水酸化ナトリウム水溶液0.14mol、乳化剤としてニューコール2360(日本乳化剤株式会社製)を化合物(A−1)全量に対して3質量%添加し、次いで80℃の熱水を化合物(A−1)の濃度が21.5質量%となるように添加して水分散液とした。さらに80℃で、化合物(A−1)全量に対して5質量%のイソプロピルアルコールと、アルキル化剤(e)としてエピクロロヒドリン0.5mol((a)のアミノ基に対する(e)が0.17当量)を添加し、80℃で2時間反応させた後、冷却し、固形分20質量%となるようにイオン交換水を添加し、紙用添加剤1を得た。
(a)〜(e)及び塩基の種類や量を表1のように変えたほかは、合成例1と同様に行い、紙用添加剤2〜4、6〜9、11、12、及び比較用紙用添加剤1〜5を得た。
(a)〜(e)及び塩基の種類や量を表1のように変え、(c)のアジピン酸を1価脂肪酸(b)と同じタイミングで添加したほかは、合成例1と同様に行い、紙用添加剤5及び10を得た。
広葉樹晒クラフトパルプ(LBKP)をフリーネス400mlに叩解し、パルプスラリーを調整した。このパルプスラリーを攪拌しながら、パルプの固形分質量当たり、前記の紙用添加剤1を0.8固形分質量%、硫酸バンドを0.5固形分質量%、カチオン化澱粉を0.5固形分質量%、AKDサイズ剤を0.08固形分質量%、軽質炭酸カルシウムを16固形分質量%となるように添加して紙料を調整した。この紙料を使用して、角型シートマシンにて抄紙して、坪量80g/m2の手すき紙を得た。得られた手すき紙を23℃、RH50%の条件化に24時間調湿したあと、密度、サイズ度、比容積、比容積向上度を以下の方法により測定し、算出した。比容積向上度の値は紙厚向上効果の指標になる値であり、その値が高い程、紙厚向上効果が高い。比容積向上度とサイズ度の結果を表2に示す。
サイズ度…JIS P 8122 紙のステキヒトサイズ度試験方法
密度…JIS P 8118 紙及び板紙−厚さ及び密度の試験方法
比容積…密度の逆数
比容積向上度…「(比容積)/(紙用添加剤無添加の場合の比容積※)×100−100※表2における参考例1の比容積」
実施例1と同様に、紙用添加剤2〜12をそれぞれ添加して抄紙し、密度、サイズ度を測定した。
実施例1と同様に、比較用紙用添加剤1〜5をそれぞれ添加して抄紙し、密度を測定した。比容積向上度が満足できるレベル(7%以上を目安とした)に達しなかったので、サイズ度は測定しなかった。
紙用添加剤を添加しないことを除いて、実施例1と同様に抄紙し、密度、サイズ度を測定した。
TETA:トリエチレンテトラミン
TEPA:テトラエチレンペンタミン
ステアリン酸さくら:パルミチン酸/ステアリン酸(日油株式会社製)
PM500:オレイン酸(ミヨシ油脂株式会社製)
Emersol873:イソステアリン酸(コグニス社製)
COOH:カルボキシル基
COOX:カルボキシル基の塩
Claims (7)
- 1分子内に3個以上のアミノ基を有するポリアルキレンポリアミン(a)、
炭素数8〜22の1価脂肪酸(b)、
多価カルボン酸類(c)、
尿素類(d)
及びアルキル化剤(e)
を反応させて得られる化合物(A)を含有することを特徴とする紙用添加剤。 - 化合物(A)がカルボキシル基又はその塩を有することを特徴とする請求項1に記載の紙用添加剤。
- 尿素類(d)が尿素であり、かつ、アルキル化剤(e)がエピハロヒドリン類であることを特徴とする請求項1に記載の紙用添加剤。
- 化合物(A)が、
(a)のアミノ基1当量に対して、
(b)のカルボニル基が0.35〜0.65当量、
(c)のカルボニル基が0.01〜0.20当量、
(d)が0.01〜0.35当量
(e)が0.01〜0.40当量
の割合で反応させて得られる化合物であることを特徴とする請求項1〜3のいずれか一項に記載の紙用添加剤。 - 請求項1〜4のいずれか一項に記載の紙用添加剤を含有することを特徴とする紙。
- 1分子内に3個以上のアミノ基を有するポリアルキレンポリアミン(a)、
炭素数8〜22の1価脂肪酸(b)、
多価カルボン酸類(c)、
尿素類(d)
及びアルキル化剤(e)
を反応させて得られる化合物(A)を含有することを特徴とする紙用添加剤の製造方法。 - (a)のアミノ基1当量に対して、
(b)のカルボニル基が0.35〜0.65当量、
(c)のカルボニル基が0.01〜0.20当量、
(d)が0.01〜0.35当量
(e)が0.01〜0.40当量
の割合で反応させて得られる化合物(A)であることを特徴とする請求項6に記載の紙用添加剤の製造方法。
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